Articulo 2
Articulo 2
Review
The multiple nutrition properties of some exotic fruits: Biological activity and
active metabolites
Valery M. Dembitsky a, Sumitra Poovarodom b, Hanna Leontowicz c, Maria Leontowicz c, Suchada Vearasilp d,
Simon Trakhtenberg e, Shela Gorinstein a,⁎
a
The Institute for Drug Research, School of Pharmacy, The Hebrew University, Hadassah Medical School, Jerusalem 91120, Israel
b
Department of Soil Science, King Mongkut's Institute of Technology, Ladkrabang, Bangkok 10520, Thailand
c
Department of Physiological Sciences, Faculty of Veterinary Medicine, Warsaw University of Life Sciences (SGGW), Warsaw 02787, Poland
d
Department of Plant Science and Natural Resources, Faculty of Agriculture/Postharvest Technology Research Institute/Postharvest Technology Innovation Center, Chiang Mai University,
Chiang Mai 50200, Thailand
e
Kaplan Medical Center, Rehovot 76100, Israel
a r t i c l e i n f o a b s t r a c t
Article history: The main objective of this review was to describe the physicochemical and nutritional characteristics of
Received 26 November 2010 twenty selected exotic fruits and the influence of their physiologically active compounds on human health,
Accepted 1 March 2011 through scientifically proven information. The review presents the biologically active metabolites derived
from exotic fruits (polyphenols, flavonoids, flavanols, tannins, ascorbic acid, anthocyanins, volatile
Keywords:
compounds, minerals, and organic acids) and various analytical methods for their detection (elemental
Exotic fruits
Bioactive compounds
analysis, electrophoretic separation by SDS-polyacrylamide gel electrophoresis, and fast protein liquid and
Antioxidant potential ion-exchange chromatography; GC–MS, HPLC/diode array detection (DAD), circular dichroism (CD),
Rats differential scanning calorimetry (DSC), Fourier transform infrared (FT-IR), ultraviolet spectroscopy, two-
Cholesterol-containing diets and three-dimensional fluorimetry (2D-FL) and (3D-FL), and antioxidant radical scavenging assays (DPPH,
FRAP, CUPRAC, ABTS, and ORAC). The correlation between the polyphenols and other bioactive compounds,
and their antioxidant activities was reported for different fruit extracts. During the last two decades our
international scientific group investigated in vitro the physicochemical and nutritional characteristics of
avocado, dragon fruit, durian, kiwifruit, mango, mangosteen, persimmon and snake fruit, and in vivo their
influence on laboratory animals and humans. Supplementation of diets with exotic fruits positively affects
plasma lipid profile, antioxidant activity and histological examination of aorta in rats fed cholesterol-
containing diets.
The interaction between drugs and serum albumin plays an important role in the distribution and metabolism
of drugs. The properties of polyphenol methanol extracts of exotic fruits showed the ability to quench serum
albumin by forming the complexes similar with the ones between proteins and pure flavonoids. Our
experimental data and a wide range of other investigations are included in this review. In conclusion, it is
nessasary to promote a consumption of exotic fruits (a rich source of natural antioxidants) as a supplement to
everyday human diet.
© 2011 Elsevier Ltd. All rights reserved.
Contents
1. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1672
2. Selected tropical and exotic fruits, their bioactive and pharmacological properties . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1673
2.1. Açaí . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1673
2.2. Acerola . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1674
2.3. Avocado . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1675
2.4. Dragon fruit . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1676
2.5. Durian . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1677
2.6. Graviola . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1679
0963-9969/$ – see front matter © 2011 Elsevier Ltd. All rights reserved.
doi:10.1016/j.foodres.2011.03.003
1672 V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701
1. Introduction polyphenols (Gorinstein et al., 2010). Some studies have shown the
effect of various phenols such as gallic acid, myricetin, flavan-3-ols
The major source of biologically active substances, such as (1)-catechin and (2)-epicatechin, and others as antioxidants. Gallic
vitamins and secondary metabolites (polyphenols, carotenoids, acid occurs naturally in plants and has been found to be pharmaco-
sterols, glucosinolates, and saponins) is present in herbs, fruits and logically active as an antioxidant, antimutagenic, and anticarcinogenic
vegetables (Alothman, Bhat, & Karim, 2009; Cassileth, 2008; Xu et al., agent. It is an established fact that supplementation of diet with fruits
2004; Yang, Paulino, Janke-Stedronsky, & Abawi, 2007; Yuka, Yumiko, and vegetables prevents atherosclerosis and other diseases (Duttaroy
Miyo, & Takashi, 2003). The consumption of fruits and vegetables is & Jorgensen, 2004). It was shown that consumption of kiwifruit
globally insufficient and should be encouraged, and it may be useful to lowered blood triglyceride levels by 15% compared with control. The
enhance fruit concentrations of vitamins and secondary metabolites authors reported that consuming two or three kiwifruit per day for
by genetic and/or environmental approaches (Poiroux-Gonord et al., 28 days reduced platelet aggregation response to collagen (Duttaroy
2010). It has been shown that individuals who eat daily five servings & Jorgensen, 2004). It was demonstrated that consumption of certain
or more of fruits and vegetables have approximately half the risk of berries and fruits such as blueberries, mixed grape and kiwifruit, was
developing a wide variety of cancer types, particularly those of the associated with increased plasma hydrophilic (H-) or lipophilic (L-)
gastrointestinal tract (Gescher, Pastorino, Plummer, & Manson, 1998). antioxidant capacity (AOC) measured as Oxygen Radical Absorbance
The collected data (Burton-Freeman, 2010) suggest that consuming Capacity (ORAC). AOC in the postprandial state and consumption of an
phenolic-rich fruits increase the antioxidant capacity of the blood. energy source of macronutrients containing no antioxidants
When the fruits are consumed with high fat and carbohydrate pro- was associated with a decline in plasma AOC. Previous studies
oxidant and pro-inflammatory meals, they may counterbalance their (Chidambara, Kotamballi, Jayaprakasha, & Patil, 2010) have demon-
negative effects. It was reported that one of the important predis- strated that D-limonene inhibits cancer cells (pulmonary, colon and
posing mechanisms in the development of atherosclerosis is oxidation breast) based on cell culture and animal studies. D-Limonene, a major
of the cholesterol-rich LDL-C particles (Aviram, 1993; Steinberg, monoterpene found in citrus, represents for 40–90% of volatile
Parthasarathy, Carew, Khoo, & Witztum, 1989; Witztum & Steinberg, components (Chidambara et al., 2010). Fruit flavor is important for
1991). The oxidation of LDL-C enhances its atherogenicity and human health. Many fruits including citrus, berries, mangosteen,
facilitates penetration of lipids into the arterial wall, causing the pomegranate, have attracted much attention of their health benefits
occlusion of arteries in general and coronary arteries in particular. It is due to the wide range of bioactivities (Chen & Wang, 2008). The
now known that nutritional antioxidants in general, especially antioxidant, anti-inflammatory, anticancer and antimicrobial activi-
phenolic substances, can prevent lipid peroxidation. It was shown ties are connected with phytochemicals, such as anthocyanins,
that a low level of plasma antioxidants leads to a high mortality from flavonoids, polyphenolics, and vitamins. Similar biological activities
coronary atherosclerosis (Rankin et al., 1993). Therefore, some of the essential oils in fruit seeds, flesh and peels have not been paid
authors propose diets rich in vegetables and fruits, which are the enough attention compared with those of non-volatile chemicals. The
natural source of antioxidants (Lorgeril et al., 1994). There is evidence chemical compounds and metabolites of fruit flavors, as well as their
that fruits and vegetables are playing a beneficial role in prevention bioactivities and bioavailabilities in relation to their potential impact
and even treatment of different diseases (Kris-Etherton et al., 2002; on human health and diseases have to be studied. In recent years
Lim, Lim, & Tee, 2007; Luximon-Ramma, Bahorun, & Crozier, 2003; some pharmacological activities such as anti-tyrosinase, anti-glycated
Paganga, Miller, & Rice-Evans, 1999; Proteggente et al., 2002). Some and anticancer activities, and memory-enhancing effects of longan
studies have shown that dietary fiber and polyphenols of fruits aril, pericarp or seed extract have been found, implicating a significant
improve lipid metabolism and prevent the oxidation of low density contribution to human health (Yang, Jiang, Shi, Chen, & Ashraf, 2011-
lipoprotein cholesterol (LDL-C), which hinder the development this issue). The synergetic effect, which could exist between
of atherosclerosis (Gorinstein, Bartnikowska, Kulasek, Zemser, & individual bioactive compounds, means that the antioxidant capacity
Trakhtenberg, 1998; Gorinstein, Kulasek, et al., 1998; Gorinstein, may be higher than their sum (Poeggeler et al., 1995), and not only
Zemser, Haruenkit, et al., 1999; Gorinstein, Zemser, Vargas-Albores, individual bioactive compounds, but also the overall antioxidant
et al., 1999). Indeed, recent experiments on rats fed diets supple- capacity have to be determined in fruits. Some antioxidant assays give
mented with persimmon show that this fruit exercises a marked different antioxidant activity trends (Ou, Huang, Hampsch-Woodill,
antioxidant effect that is most likely due to a relatively high content of Flanagan, & Deemer, 2002). Total phenolics, flavonoids and flavanols
V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701 1673
& Hansen, 2000; Leontowicz, Leontowicz, Drzewiecki, Haruenkit, et al., Sample α-Tocopherol γ-Tocopherol δ-Tocopherol Total α-TEb
2006; Leontowicz, Leontowicz, Drzewiecki, Jastrzebski, et al., 2007; Lim tocopherol
et al., 2007; Shui & Leong, 2005; Yang et al., 2007; Zadernowski, Brazil nut 72.5 74.3 5.9 152.8 80.2
Czaplicki, & Naczk, 2009). Exotic fruits play exactly the same role in the Red açaí pulp 147.7 ND ND 147.7 147.7
prevention of atherosclerosis, therefore a detailed description has to Inajá pulp 114.8 50.9 ND 165.8 117.4
Buriti pulp 252.2 878.4 224.2 1129.8 346.7
be paid to this kind of fruits. Tropical fruit crops are common in the
Buriti nut NDc 616.9 378.8 995.7 73.3
geographical zone stretching from 30 south latitude with up to 30 Uxi pulp 167.2 337.5 ND 504.7 200.9
north latitude. Temperature conditions in this area differ (the average a
Values expressed as mean ± standard deviation (n = 9).
in year 25 °C, while the oscillations are observed from 16 to 36 °C). In b
α-TE = α-tocopherol equivalents.
the tropics, the maximum number of cultivated plant families: here c
ND = not detected.
are grown not only plants that are in the culture of temperate and
subtropical zones, but also endemic to many families. In tropical
countries, fruits play a major role in human life. Bananas, breadfruit mango (Mangifera indica L.) (Dutta, Kundu, & Ahmed, 2008; Masibo &
and papaya trees, nuts, coconut and fruit of date palms are among the He, 2008; Melo, Maciel, Galvao de Lima, & Rodrigues de Araujo, 2008;
basic food of the population in the tropics. A large number of exotic Robles-Sanchez et al., 2009; Wu & Ke, 2008) and avocado (Persea
fruits can be seen in Malaysia throughout the year (Alothman et al., americana) (Elez-Martinez, Soliva-Fortuny, Gorinstein, & Martín-
2009; Ikram et al., 2009). Among the variety of fruits that can be Belloso, 2005). It was shown that durian (Haruenkit et al., 2010),
distinguished are papaya, rambutan, guava, chiku, coconut, durian, mango (Masibo & He, 2008; Robles-Sanchez et al., 2007; Robles-
pineapple, mango, watermelon, dooku, mangosteen, bananas, pomelo, Sanchez et al., 2009) and avocado (Elez-Martinez et al., 2005) possesses
jumbo sweet flag and cannon. Lorenzi, Bacher, Lacerda, and Sartori high nutritional and bioactive properties. Kiwifruit (Actinidia deliciosa)
(2006) described 827 tropical fruits, including 389 species and 438 is rich in bioactive compounds especially in polyphenols (Park, Jung, &
cultivars in Brazil. Tropical and subtropical fruits, such as mango, Gorinstein, 2006; Park, Jung, Kang, Deldado-Licon, Katrich, et al., 2006;
guava, papaya, persimmon and many others, are well known in North Park, Jung, Kang, Drzewiecki, et al., 2006).
America and Europe, and the scientific basis for their consumption is This review describes the bioactivity of 20 exotic fruits, their
well founded (Dube et al., 2004; Garcia, Magpantay, & Escobin, 2005; properties and their influence on metabolism as supplementation to
Leontowicz et al., 2006). Tropical and subtropical fruits, such as red human diet. The volatile substances, fatty acids and other metabolites
and white guava, green and ripe mango, banana, passion fruit, star which are important for the human health are reviewed. Till now such
fruit, rose apple, papaya, lime, passiflora, kumquat, pineapple, review on exotic fruits was not published, because this review is based
carambola, feijoa, kiwano, cherimoya, sapodilla, mamey, lychee and not only on the literature data, but also on some of our experiments,
longan, are common ingredients of diets in North America and which are for the first time reported in the review. The collected data
nowadays in Europe as well (De Assis et al., 2009; Doyama, Rodrigues, are important from the point of the comparison of 20 exotic fruits in
Novelli, Cereda, & Vilegas, 2005; Dube et al., 2004; Kondo, Kittikorn, & their fresh form exactly as these fruits are mostly consumed in human
Kanlayanarat, 2005; Luximon-Ramma et al., 2003; Mahattanatawee, diet.
Manthey, Talcott, Goodner, & Baldwin, 2005; Murcia, Jimenez, &
Martinez-Tome, 2001; Nilsson et al., 2005; Proteggente et al., 2002; 2. Selected tropical and exotic fruits, their bioactive and
Talcott, Percival, Pittet-Moore, & Celoria, 2003; Wu et al., 2005; Yuka pharmacological properties
et al., 2003). The 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-
scavenging activities and polyphenol contents of some tropical dried 2.1. Açaí
fruits were evaluated and compared with fresh fruits. The qualities of
persimmon, hawthorn and apricot were close to those of the dry The homeland of açaí (Euterpe oleracea, acaizeiro) is northern
fruits and showed high DPPH radical-scavenging activity (Ishiwata, Brazil and the most abundant palm açaí grows in the Brazilian state of
Yamaguchi, Takamura, & Matoba, 2004; Park, Jung, Kang, Delgado-Licon, Pará. Açaí fruit has an unusual taste, which is reminiscent of the taste
Ayala, et al., 2006). The consumption of new exotic fruits has significantly of raspberries and blackberries with a touch of walnut, and especially
increased (Corral-Aguayo, Yahia, Carrillo-Lopez, & Gonzalez-Aguilar, rich in iron, vitamins B1 and E. The outside skin is of a similar texture
2008; Haruenkit, Poovarodom, Leontowicz, et al., 2007; Haruenkit, as a blueberry, smooth on the exterior to the touch, showing the same
Poovarodom, Vearasilp, et al., 2010; Luximon-Ramma et al., 2003). size, shape, and color. The inside of the açai berry is soft and is easily
Among these fruits durian (Durio zibethinus Murr.) is less known than formed into a pulp, which is one of the preferred forms of this fruit. It
Table 1
Phytosterol composition (mg per 100 g) of analyzed fruits and nuts.a
C in oranges (one cherry contains double the allowance intake of (green) fruit, such as Me Pr ketone, E or Z-hexenyl acetate and 1-
vitamin C). The fruit is used in jellies, jams, and can be frozen without octadecanol were identified in acerola fruit. Volatiles of acerola were
losing its vitamin C content. 100 g of acerola with a low percentage of characterized by GC/MS. 3-Methyl-3-buten-1-ol was identified as the
water (9.4%) has high calorie contents (332 kcal) due to 3.2 g lipids, major constituent. Organoleptic properties of its esters are also
16.94 g protein and 57.24 g carbohydrates in 100 g FW. Acerola contains documented (Schippa, George, & Fellous, 1993).
a high content of crude fiber (26.5%), ash (0.4%), ascorbic acid (66 mg/g
FW) and minerals (mg/100 g FW) such as iron (37), calcium (41), 2.3. Avocado
potassium (41), magnesium (22), zinc (0.09), manganese (0.7),
phosphorus (0.08) and copper (0.15 μg/100 g FW). Such nutritional Avocado, or Perseus American (P. americana Mill.) is a kind of
macro- and micro-component values make acerola one of the most evergreen fruit plants of the genus Perseus family, the type species of
important fruits for human consumption (Rufino et al., 2010). The this genus, and an important fruit crops. The pear-shaped, egg-shaped
reported results (Rufino et al., 2010; Sampaio et al., 2009) show the or spherical fruit is 7–20 cm long, with a weight from 100 to 1000 g
considerable antioxidant capacity by the DPPH, ABTS and FRAP methods and has a large central seed (5–6.4 cm long). The non-processed
found for acerola, vitamin C, anthocyanins, yellow flavonoids, total avocado does not have a specific taste. In the world there are about
carotenoids, and total extractable polyphenols. Its lipid fraction has the 500 varieties of avocados, which differ in the fruit shape and color.
following fatty acids: oleic (31.9%), linoleic (29.2%), palmitic (21.8%), Flavor selection is hardly affected, and, of course, avocados retain their
stearic (13.9%) and linolenic (1.3%) (Medeiros De Aguiar, Rodrigues, useful properties. The availability of the fruit is May–February
Ribeiro Dos Santos, & Sabaa-Srur, 2010). Two acerola genotypes which according to variety. In Mexico one of the most common and easy-
were harvested from a Brazilian plantation during the 2003 and 2004 care varieties of avocado Hass cultivar is harvested all year. The pulp
summer harvests presented the major carotenoids (μg/100 g FW): β- contains about 30% of fat, protein, calcium, iron, a large number of easily
carotene (265–1669), lutein (37–100), β-cryptoxanthin (16–56) and α- digestible fats, mineral salts, vitamins E, B1, B2, and D. Avocado has a
carotene (7.8–59). In both harvests, the β-carotene, β-cryptoxanthin positive influence on short-term memory and reduces the risk of car-
and α-carotene levels were higher in the Olivier genotype, whereas the diovascular disease. Avocado is rich in serotonin 5-hydroxytryptamine
lutein content was higher in the Waldy Cati 30 genotype (De Rosso & (5-HT) which is a monoamine neurotransmitter (Fig. 3). Other fruits
Mercadante, 2005). Anthocyanin aglycons and other phenolic com- and nuts have also a high concentration of serotonin (μg/g wt) such as
pounds were identified in acerola (M. punicifolia, L.). Anthocyanins, pineapple 17.0; banana 15.0; kiwifruit 5.8; plums 4.7; and tomatoes 3.2.
flavonoids, and phenolic acids were fractionated and characterized. The Urinary excretion of 5-hydroxyindoleacetic acid was measured in 129
total content of anthocyanin pigments was 37 mg/100 g of ripe acerola healthy subjects, 69 were on a free diet and 60 on a diet lacking the
skin. The identified phenolic pigments were pelargonidin, malvidin-3,5- above foods. The average excretion of serotonin was 3.49 mg/24 h for
diglycoside and cyanidin 3-glycoside (Fig. 2). Quercetin, kaempferol and control group, with a range of 1.10–7.92 mg/24 h, and the serotonin-
the phenolic acids (p-coumaric, ferulic, caffeic and chlorogenic) were also poor group was 1.67 mg/24 h, with a range of 0.72–3.12 mg/24 h.
identified (Vendramini & Trugo, 2000; Vendramini & Trugo, 2004). Five Ingestion of these fruits resulted in an increase in urinary 5-
different polyphenolic compounds were identified in the samples by HPLC hydroxyindoleacetic acid excretion with no change in platelet
and diode-array detection: chlorogenic acid, (−)-epigallocatechin gallate, serotonin concentration (Feldman & Lee, 1985). Tryptophan is an
(−)-epicatechin, procyanidin B1 and rutin, being the two last predom- essential amino acid and metabolic precursor of serotonin. Serotonin
inant. Three soluble polyphenolic fractions (phenolic acids, anthocyanins is both a classical neurotransmitter and a signaling molecule that
and flavonoids) were separated from the different sample extracts, and plays crucial roles in the development of neural circuits and plasticity
their respective antioxidant activities calculated. Among them, phenolic (Serfaty, Oliveira-Silva, Faria Melibeu, & Campello-Costa, 2008).
acids are the main contributors to the antioxidant activity (Mezadri, Twenty-four minerals were quantified by inductively coupled
Villaňo, Fernandez-Pachán, García-Parrilla, & Troncoso, 2008). The 31 plasma optical emission spectrometric analysis for avocado honey
compounds in the mature (red) fruits, such as acetyl Me carbinol, 2- samples. The elements Al, Ba, Ca, Co, Cr, Cu, Fe, K, Li, Mg, Mn, Na, Ni, P,
methylpropyl acetate, limonene, E or Z-octenal, Et hexanoate, isoprenyl Pb, S, Se, Si and Zn were detected in all samples (Terrab, Recamales,
butyrate and acetophenone; 23 — in the intermediate (yellow), such as, Gonzalez-Miret, & Heredia, 2005), seven elements were very
Me hexanoate, 3-octen-1-ol and hexyl butyrate, and 14 — in the immature abundant (Ca, K, Mg, Na, P, S and Si), five were not abundant (Al,
Cu, Fe, Li and Zn) and 12 were trace elements (As, Ba, Cd, Co, Cr, Mo,
Ni, Mo, Pb, Se, Sr and V). Avocado is a good source of bioactive
compounds such as monounsaturated fatty acids and sterols. The
OMe main fatty acid identified and quantified in avocado was oleic acid
(about 57% of total content), and linoleic, palmitoleic, cis-vaccenic,
OH
and γ-linolenic acids; β-sitosterol was found to be the major sterol
HO O
OMe
H
- N
OH O Cl
O O HO
O
HO
O OH
O HO
HO
OH H 2N
Malvidin-3,5-diglucoside Serotonin
Fig. 2. Diglycoside in acenole. Fig. 3. Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter.
This figure is adapted from Vendramini and Trugo (2004). This figure is adapted from Feldman and Lee (1985).
1676 V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701
(about 89% of total content), and as well as stigmasterol, and avocado are comparable with those indices in mango and durian. In
campesterol (Plaza, Sanchez-Moreno, de Pascual-Teresa, de Ancos, & order to obtain the best results, a combination of these fruits has to be
Cano, 2009). The chrysanthemaxanthin, as a major pigment in included in diets as was shown by Gorinstein et al. (2011-this issue)
avocado pulp, was confirmed by mass spectrometry and the identity and Poovarodom et al. (2010).
of neoxanthin similarly established. A carbonyl pigment was
identified as 3-hydroxysintaxanthin. Two new apocarotenoids 2.4. Dragon fruit
were isolated. The structure of 5,8-epoxy-5,8-dihydro-10′-apo-β-
caroten-3,10′-diol was assigned. The other carotenoid had an acid Dragon fruit (Hylocereus sp) or red pitaya (or pitahaya), is the fruit
labile pentaene chromophore, and structure was tentatively of the cactus species Hylocereus undatus. The plant is nicknamed
assigned on similar evidence. These substances were the first natural Queen of the Night, Moonflower and/or Lady of the Night, because the
allyic apocarotenols whose structures were established (Gross, large flowers only bloom at night time. The skin of the dragon fruit is a
Gabai, Lifshitz, & Sklarz, 1974). β-Caryophyllene (44%) and valen- thin rind and usually covered in scales, and the center of the fruit is
cene (16%) were the most abundant compounds in the oil. Other made up of a red or white, sweet tasting pulp which remembers
quantitatively significant constituents (Ogunbinu, Ogunwande, kiwifruit. The flesh is mildly sweet. Because of its exotic and
Flamini, & Cioni, 2007) were germacrene D (6%), α-humulene (5%) impressive appearance, this fruit enjoys growing popularity in Europe
and δ-cadinene (5%). and the United States. The fruit is also converted into juice or used to
Volatile components of two cultivars of avocado fruits (California flavor other beverages. The availability of the fruit is April–May and
and Haas) were isolated by simultaneous steam distillation and September–November, but year round according to variety. This
solvent extraction. Both cultivars had 227 and 289 μg/kg of total exotic fruit is native to Mexico and Central and South America and is
volatile compounds, respectively. Major components were (E)- also cultivated in Southeast Asian countries. H. undatus and Hylocereus
nerolidol, with lesser amounts of β-caryophyllene, β-pinene, trans- polyrhizus are two varieties of the commonly called pitaya fruits.
α-bergamotene and β-bisabolene (Pino, Rosado, & Aguero, 2000). Essential fatty acids, namely, linoleic acid and linolenic acid form a
Hydrocarbons (mainly sesquiterpenes) and alkanals were the significant percentage of the unsaturated fatty acids of the seed oil
predominant constituents present. In the immediate extraction of extract. Both pitaya varieties exhibit two oleic acid isomers. Both
the avocado mesocarp, β-caryophyllene (60%) was the main sesqui- pitaya varieties (Ariffin et al., 2009) contain about 50% essential fatty
terpene, followed by α-humulene (5.9%), caryophyllene oxide (4.8%), acids: oleic acid (C18:1, 21–24%), linoleic acid (C18:2, 48–50%) and
α-copaene (4.5%) and α-cubebene as the main hydrocarbons; linolenic acid (C18:3, 1.0–1.5%), and cis-vaccenic acid (C18:1, 2.8–3%).
alkanals were present, but only in low concentrations. The β- Fast protein liquid and ion-exchange chromatography, fluorescence,
caryophyllene (29%) was the main sesquiterpene, followed by α- Fourier transform IR (FT-IR) spectra, elemental and electrophoretic
copaene (11%), a cadinene isomer (8.5%), α- and β-cubebene (7.7%), analyses were described to characterize proteins from 7 species of
α-farnesene (5.3%) and octane (4.8%) as principal hydrocarbons; Cactaceae, which can be divided into 3 groups based on their chemical
decenal (6.3%) and heptenal (3.2%) were the main aldehydes and biochemical properties. Ammonium sulfate precipitation yielded
(Sinyinda & Gramshaw, 1998). The n-alkane composition of avocado complex of electrophoretic patterns with the major bands of 24 and
pulp oil (cv. Hass) was investigated during fruit ripening. Fourteen 32 kDa. The SDS-polyacrylamide gel electrophoretic (PAGE) patterns
compounds were detected ranging from n-C21 to n-C34; mainly n- did not differ by the year of sample collection (1986 and 1992). It was
C24, followed by n-C25 and then by n-C23. Quantities of n-C21, n-C22, disclosed that protein characterization of cactus juices may be useful
n-C23, n-C27 and n-C28 progressively increased during ripening, in cactus taxonomy at the family level. Differences in the emission
whereas n-C24, n-C25, n-C26, n-C29, n-C30 and n-C34 decreased from peak response and fluorescence intensity in fluorescence emission, as
the first harvest date to the third harvest date. While odd-numbered well as the changes in amide band content in FT-IR spectra were
carbon n-alkanes increased (52.38%, 52.85% and 53.06% for the three reported (Gorinstein, Zemser, Vargas-Albores, & Ochoa, 1995).
samples, respectively), even-numbered carbon n-alkanes decreased Characterization of three cactus proteins (native and denatured)
as the fruit ripened (47.62%, 47.15% and 46.94%). The total n-alkane from Machaerocereus gummosus (Pitahaya agria), Lophocereu schottii
content (Giuffre, 2005) decreased during ripening, from 25.20 mg/kg (Garambullo), and Cholla opuntia (Cholla), was based on electropho-
(first harvest date) to 17 mg/kg (third harvest date). As it was retic, fluorescence, CD, DSC (differential scanning calorimetry), and
described (Bezabih, Pellikaan, Tolera, & Hendriks, 2011) n-alkanes can FT-IR measurements. The stated results of intrinsic fluorescence, DSC,
be used as diet composition markers. The major bioactive compounds and CD were dissimilar for the three species of cactus, providing
and antioxidant potential of avocado were studied and compared evidence of differences in secondary and tertiary structures. It was
with durian and mango (Elez-Martinez et al., 2005; Gorinstein, verified by Gorinstein et al. (1995) that cactus proteins may be
Leontowicz, et al., 2011; Poovarodom et al., 2010). It was reported situated in the following order corresponding to their relative
that for this purpose HPLC, three-dimensional fluorescence (3D-FL), stability: M. gummosus (Pitahaya agria)N C. opuntia (Cholla)N L. schottii
several radical scavenging assays and multivariate factor analysis (Garambullo). Thermodynamic properties of `proteins and their
were used. In durian, mango and avocado the following major changes upon denaturation (temperature of denaturation, enthalpy,
nutritional components were observed: total fiber (g/100 g FW), and the number of ruptured hydrogen bonds) were correlated with
3.2 ± 0.3, 2.9 ± 0.2 and 6.2 ± 0.5; total proteins, 1.4 ± 0.1, 0.8 ± 0.06 the secondary structure of proteins and disappearance of α-helix
and 1.9 ± 0.2; total fats, 5.3 ± 0.4, 0.4 ± 0.03 and 21.2 ± 1.3; carbohy- (Gorinstein, Zemser, Vargas-Albores, et al., 1999). From the studies
drates, 27.1 ± 1.6, 28.2 ± 1.6 and 8.3 ± 0.6. It was reported that the shown below (Gorinstein, Zemser, Vargas-Albores, et al., 1999;
contents of total fiber, proteins and fats were significantly higher Gorinstein et al., 1995) the most useful from the Cactaceae family are
(p b 0.05) in avocado. The carbohydrates were significantly lower in Pitaya agria or Sour Pitaya (M. gummosus) and Pitaya Dulce (Stenocereus
avocado (p N 0.05) than in the two other fruits. It was found a thurberi). The fruit of Pitaya Agria is even sweeter than the fruit of Pitaya
similarity in acetone extracts between durian and mango in the Dulce. Pitaya is a perennial plant with triangular cactus genus, of which
contents of polyphenols (1.66 ± 0.08, 1.48 ± 0.05, mg GAE/g DW, fruit is rich in nutritive value and can be eaten directly, flowers can be
respectively), and in some antioxidant assays such as ABTS (11.98 ± used as vegetables, but the pitaya stems are not being used (Guo, Dai,
0.5, 12.24 ± 0.5, μm TE g− 1 DW, respectively) and DPPH (5.61 ± 0.3, Liang, & Li, 2010). H. undatus and H. polyrhizus are two varieties of the
5.22 ± 0.2, μm TE g− 1 DW, respectively). Durian and avocado were commonly called pitaya fruits. Dragon fruit (H. polyrhizus) is well known
similar in the contents of polyphenols, ABTS and DPPH values in water for the rich nutrient contents and it is available worldwide for improving
and in methanol extracts. The nutritional and bioactive properties of many health problems. Maximum antioxidant capacity, total phenolic
V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701 1677
and betalain contents were observed in the genotype ‘Lisa’ of 5 different raw material for wine production (Yan, Guo, Zhu, Yang, & Liang, 2008),
Costa Rican genotypes of purple pitaya (Hylocereus sp.) and of as well as the optimal enzymatic treatment for clarification of white
H. polyrhizus fruits. While non-betalainic phenolic compounds contrib- pitaya juice using Pentinex Ultra SP-L for commercialization was
uted only to a minor extent, betalains were responsible for the major investigated (Aliaa, Mazlina, Taip, & Abdullah, 2010).
antioxidant capacity of purple pitaya juices evaluated (Esquivel,
Stintzing, & Carle, 2007; Kugler, Stintzing, & Carle, 2007). The bioactive 2.5. Durian
compounds in red dragon fruit were the following: 86.10 mg GAE of
total polyphenolic compound in 0.50 g of dried dragon fruit; tannins of Durian (D. zibethinus Murray) is one of the most important seasonal
2.30 mg CE/g (catechin equivalents); DPPH showed that the effective fruits in tropical Asia. Durian cultivars are derived from D. zibethinus,
concentration (EC50) for dragon fruit was 2.90 mM vitamin C originating in the Malay Peninsula (Voon, Hamid, Rusul, Osman, & Quek,
equivalents/g dried extract (Rebecca, Boyce, & Chandran, 2010). Total 2007). This fruit of several trees is widely known and revered in
phenol (R2 = 0.97) and ascorbic acid (R2 = 0.79) concentrations Southeast Asia as the “king of fruits”. The durian is distinctive for its large
were correlated with the antioxidant capacity of four pitaya cactus size, unique odor, and formidable thorn-covered husk. The fruit can
(Stenocereus stellatus Riccobono) fruit types (red, cherry, yellow and grow as large as 30 cm long and 15 cm in diameter and it typically
white), but the contribution of ascorbic acid accounts only for 4–6% of weighs 1 to 3 kg. Its shape ranges from oblong to round, the color of its
antioxidant capacity. White and yellow types contained a higher husk is green to brown, and its flesh pale is yellow to red, depending on
amount of phenol compounds and ascorbic acid than the cherry and the species. The fruit is almost the size of a basketball, light green, and
red types. The antioxidant capacity displayed by the four pitaya types is very spiny, sweet with a custard like texture and with a strong odor. The
similar to those reported for some fruits of the Vaccinium genus, edible flesh emits a distinctive odor, strong and penetrating even when
regarded as the fruits having the highest antioxidant capacity. The the husk is intact. The availability of durian is from the middle of May to
consumption of pitaya fruits could provide the same protective effect the end of July. The importance of this fruit is mostly connected with its
against free radicals as berries of the Vaccinium genus, reducing risk of composition and antioxidant properties (Arancibia-Avila et al., 2008;
chronic diseases; thus pitaya fruits can be considered as potential Leontowicz et al., 2008; Toledo et al., 2008). It has been reported that
nutraceutical food (Beltran-Orozco, Oliva-Coba, Gallardo-Velazquez, & durian has additional valuable health properties: polysaccharide gel,
Osorio-Revilla, 2009). The total phenolic contents of red pitaya flesh extracted from the fruit hulls, reacts on immune responses and is
(42.4 ± 0.04 mg GAE/100 g flesh FW) and peel (39.7 ± 5.39 mg GAE/ responsible for cholesterol reduction (Chansiripornchai & Pongsamart,
100 g peel FW), flavonoid contents of flesh and peel did not vary much 2008). The glycemic index of durian was the lowest in comparison with
(7.21 ± 0.02 mg vs. 8.33 ± 0.11 mg CE/100 g of flesh and peel matters); papaya and pineapple. The health properties of durian are based not
betacyanins were 10.3 ± 0.22 and 13.8 ± 0.85 mg betanin equivalent only on the antioxidant properties, but also on its fatty acid composition.
per 100 g of fresh flesh and peel; the antioxidant activity, measured by Cholesterol hypothesis implied that reducing the intake of saturated fats
the DPPH• method at EC50, was 22.4 ± 0.29 and 118 ± 4.12 μmol vita- and cholesterol while increasing that of polyunsaturated oils is effective
min C equivalent/g of flesh and peel dried extract. The ABTS assay in lowering serum cholesterol, and thereby in reducing coronary heart
showed 28.3± 0.83 and 175 ± 15.7 μM TE/g of flesh and peel dried disease. The protective activity is linked with a high supply of n−3 fatty
extracts, respectively (Wu et al., 2005). The antiproliferative study on acids coming from fish and seafood, and high consumption of whole-
B16F10 melanoma cells revealed that the peel (EC50 25.0 μg of peel grain products, as well as fruits and vegetables (Siondalski & Lysiak-
matter) component was a stronger inhibitor of the growth of B16F10 Szydlowska, 2007). Durian is rich in n−3 fatty acids, compared to some
melanoma cancer cells than the flesh. The results indicated that the flesh other fruits (Phutdhawong, Kaewkong, & Buddhasukh, 2005). Volatile
and peel were both rich in polyphenols and were good sources of components of ‘Jinzhen’ durian inner-fruit and peel were studied by GC–
antioxidants. The red pitaya peel fulfilled its promise to inhibit the MS. Results showed that esters were rich, especially in durian peel
growth of melanoma cells (Wu et al., 2005). Several studies show the volatiles, in which propanoic acid, ethyl ester (47%) accounted for nearly
proximity value of red pitaya fruits but the nutrient composition of the half. Sulfo-compounds in durian volatiles were di-ethyl disulfide (8%),
stem has not been extensively studied. It was found (Ruzainah, Rahman, ethyl-propyl disulfide (0.06%), di-ethyl trisulfide (2.2%) and 3-ethyl-
Ridhwan, Che, & Nor Zaini Vasudevan, 2009) that it consists of 0.270 g of 2,4-dithiahexan-5-one (1%). It was suggested that smell and taste
protein; 0.552 g/L glucose and 132.95 mg/L ascorbic acid of dragon fruit components were different fruit flavors (substances), and several
stem and found higher than the fruit flesh of the dragon fruit. The investigations should be paid on the relationship between fruit olfactory
premature stem (Wanitchang, Terdwongworakul, Wanitchang, & quality and human health (Zhang, Zheng, Feng, Yu, & Zhang, 2008). The
Noypitak, 2010) had higher values than the mature stem of the dragon fruits of three varieties of Indonesian durian have been analyzed by
fruit which may be helpful in preventing the risk factors of certain GC–MS on sulfur-containing compounds. The S-ethyl thioacetate,
diseases. The organic components in the stems of pitaya were identified methyl ethyl disulfide, 1-hydroxy-2-methylthioethane, methyl 2-
by GC–MS and the contents of their mineral elements were determined methylthioacetate, dimethyl sulfone, diethyl disulfide, S-ethyl thio-
by ICP-MS. The results showed that it contained many kinds of mineral butyrate, ethyl 2-(methylthio)acetate, 2-isopropyl-4-methylthiazole,
elements which played an important role in our health. It contained S-isopropyl 3-(methylthio)-2-butenoate, benzothiazole, 3,4-dithia-2-
phytol, vitamin E, β-sitosterol, taraxasterol and other kinds of ethylthiohexane, S-methyl thiooctanoate, 3,5-dimethyltetrathiane,
phytosterols (Guo & Zhou, 2007). Valuable oil in the seeds of H. undatus 3,5-dimethyl-1,2,4-trithiolane, S-methyl thiohexanoate, and 5-methyl-
and H. polyrhizus pitaya varieties was extracted by different methods 4-mercapto-2-hexanone were identified. The volatile metabolites
(Ariffin et al., 2009; Rui, Zhang, Li, & Pan, 2009). Essential fatty acids are have an important effect on human health. Zhang et al. (2008)
important acids that are necessary substrates in animal metabolism and reported only the future task that it was suggested that smell and
cannot be synthesized in vivo: both pitaya varieties contain (Ariffin et al., taste components were quite different fruit flavors (substances), and
2009) about 50% essential fatty acids [C18:2 (48%) and C18:3 (1.5%)]. several investigations should be done on the relationship between
The phytosterol compounds identified in oils were cholesterol, fruit olfactory quality and human health. A strong correlation was
campesterol, stigmasterol, and β-sitosterol. Seven phenolic acid observed between sensory properties with flavor compounds and
compounds were identified, namely, gallic, vanillic, syringic, proto- physicochemical characteristics of the fruit (Voon, Hamid, Rusul,
catechuic, p-hydroxybenzoic, p-coumaric, and caffeic acids. This study et al., 2007; Voon, Hamid, Sheikh, et al., 2007). One of the three
reveals that pitaya seed oil has a high level of functional lipids and can be strongest durian odorants was identified, and odor description, as
used as a new source of essential oil (Lim, Tan, Karim, Ariffin, & Bakar, 3,5-dimethyl-1,2,4-trithiolane. Et 2-methylbutanoate were found to
2010). Red pitaya collected from Hepu in Guangxi province was used as have the highest odor impact among the non-sulfurous odorants in
1678 V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701
durian (Weenen, Koolhaas, & Apriyantono, 1996). Thirty-eight The correlation coefficients between the antioxidant capacity
volatile compounds were identified in the fresh durian flesh, of determined by FRAP and CUPRAC and for flavonoids (Fig. 4A and B)
which eleven were esters, ten alcohols, six carboxylic acids, six were lower than for total polyphenols (R2 is 0.865 and 0.711,
sulfurous and nitrogenous compounds, and five hydrocarbons. respectively). The bioactivity of ripe durian was high and the total
Processed durian fruit leather retained most of the aroma compo- polyphenols were the main contributors to the overall antioxidant
nents of fresh durian fruit. During storage, the relative proportion of capacity (Arancibia-Avila et al., 2008). The antiproliferation has to be
acids in the product increased. Esters, alcohols and aldehydes during mentioned (Haruenkit et al., 2010) among the important activities of
storage decreased, while hydrocarbons, phenolic, sulfurous and durian Mon Thong. The antiproliferative activities of methanol
nitrogenous compounds fluctuated (Jaswir, Man, Selamat, Ahmad, & extracts of Mon Thong durian at different stages of ripening on
Sugisawa, 2008). Among exotic fruits durian is less known, and the human cancer cell lines (Calu-6 for human pulmonary carcinoma and
differences between its cultivars are practically not studied (Ketsa & SNU-601 for human gastric carcinoma) were determined by MTT (3-
Daengkanit, 1999; Leontowicz et al., 2007; Mahattanatawee et al., (4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide)
2006). The content of bioactive compounds and the influence of assay. The antiproliferative activities of the methanol extracts of
cultivars in the experiments on laboratory animals and in investiga- immature, mature, ripe and overripe durian samples on two cell lines
tions of humans are significantly different (Gorinstein et al., 2000). It (Calu-6 for human pulmonary carcinoma and SNU-601 for human
was reported that cultivars of the same fruit grown in the similar gastric carcinoma) were reported (Fig. 5). The cell survival rate (%)
conditions differ significantly. Five durian cultivars (Mon Thong, for concentrations of 2000 μg/ml for mature durian was 86.8 ± 1.5,
Chani, Kan Yao, Pung Manee and Kradum) of the same stage of and 88.5 ± 2.5%, on Calu-6 and on SNU-601, respectively, showing
ripening grown in the similar conditions were compared in order to the highest antiproliferative activity in comparison with other
choose the best as a supplement to human diets. Total polyphenols samples. This investigation (Haruenkit et al., 2010) reported that
[mg gallic acid equivalent/100 g fresh weight (FW)] and flavonoids antioxidant activity of the studied samples was not always correlated
(mg catechin equivalent (CE)/100 g FW) in Mon Thong (361.49 ± with their antiproliferative activity. The effectiveness of durian as
23.2 and 93.99 ± 7.4) were significantly higher (P b 0.05) than in diet's supplement was investigated in vivo (Leontowicz et al., 2008).
Kradum (271.59 ± 11.2 and 69.29 ± 5.3) and Kan Yao (283.29 ± 16.5 Five groups of rats were fed diets supplemented with cholesterol and
and 72.19 ± 6.8). The free polyphenols and flavonoids showed lower different durian cultivars. Diets supplemented with durian cv. Mon
results than the hydrolyzed ones. Anthocyanins (mg cyanidin-3- Thong and to a lesser degree with Chani and Kan Yao significantly
glucoside equivalent/100 g FW) and flavanols (mg CE/100 g FW)
were significantly higher in Mon Thong (427.39 ± 23.8 and 171.49 ±
16.3) than in Kradum (320.29 ± 12.1 and 128.69 ± 9.7) and Kan Yao A 400 110
(335.39 ± 14.1 and 134.49 ± 11.7). UV spectroscopy and HPLC/diode 380
array detection (DAD) analyses showed that caffeic acid and 100
360
quercetin were the dominant bioactive substances in Mon Thong
mgGAE/100g FW
y = 2.8125x - 395.63 90
mgCE/100g FW
340
cultivar. The antioxidant activity (mM trolox equivalent/100 g FW) of
320
R2 = 0.972
Mon Thong cultivar (260.89 ± 20.2, 1075.69 ± 81.4 and 2352.79 ± 80
124.2) determined by ferric-reducing/antioxidant power (FRAP), 300
cupric reducing antioxidant capacity (CUPRAC) and 2, 2′-azinobis (3- 70
280
ethylbenzothiazoline-6-sulfonic acid) with Trolox equivalent antiox- 260 60
idant capacity (TEAC) assays was significantly higher (P b 0.05) than y = 0.6694x - 90.247
240
in Kradum (197.49 ± 8.9, 806.59 ± 31.2 and 1773.29 ± 102.5) and in R2 = 0.8652 50
220
Kan Yao (204.79 ± 9.7, 845.59 ± 48.6 and 1843.69 ± 107.5). The
correlation coefficients between polyphenols, flavonoids, flavanols 200 40
210 220 230 240 250 260 270 280
and FRAP, CUPRAC and TEAC capacities were between 0.89 and 0.98
μMTE/100g FW
(Apak, Guclu, Ozyurek, & Karademir, 2004; Toledo et al., 2008). In
extracted and separated by electrophoresis durian proteins, some
differences were found in the sodium dodecyl sulfate-protein bands
in the region of 16 and 68 kDa for Kradum, 45 kDa for Mon Thong and
B 400 110
three bands for Kan Yao. The bioactivity of durian cultivars Mon 380 y = 0.9014x - 684.03
R2 = 0.8906 100
Thong, Chani and Pung Manee was high and the total polyphenols 360
mgGAE/100g FW
340 90
was reported the results in vitro are comparable with other fruits 320 80
than widely used in human diets. Durian can be used as a supplement
300
for nutritional and health purposes, especially Durian Mon Thong, 70
280
Chani and Pung Manee (Toledo et al., 2008). The antioxidant
260 y = 0.1985x - 141.88 60
properties of durian at different stages of ripening showed that
total polyphenols, flavonoids, anthocyanins and flavanols in ripe 240 R2 = 0.7114
50
durian were significantly higher (p b 0.05) than in mature and 220
overripe fruits. Caffeic acid and quercetin were the dominant 200 40
950 1000 1050 1100 1150 1200 1250
antioxidant substances in ripe durian. Methanol extracts contained
a relatively high capacity of 74.9 ± 7.1% inhibition by β-carotene μMTE/100g FW
linoleic acid assay. Ferric-reducing/antioxidant power (FRAP) and
cupric-reducing antioxidant capacity (CUPRAC) assays supported Fig. 4. Correlation between measures of antioxidant capacities (AC) and total phenolics
this finding. The correlation coefficients between polyphenols and (TPOL). A, (♦) ACFRAP (μMTE/100 g FW, X) and TPOL (mgGAE/100 g, Y1), (■) ACFRAP
antioxidant capacities of durian samples with all applied assays were (μMTE/100 g, X) and TFLAV (mg CE/100 g FW, Y2). B, (⋄) ACCUPRAC (μMTE/100 g, X)
and TPOL (mgGAE/100 g, Y1), (□) ACCUPRAC (μMTE/100 g, X) and TFLAV (mg CE/
about 0.98. A very good correlation was observed between the 100 g, Y2). Abbreviations: FRAP, ferric-reducing/antioxidant power; CUPRAC, cupric
antioxidant capacities determined by FRAP and CUPRAC (Fig. 4A and reducing antioxidant capacity; TPOL, total polyphenols; TFLAV, total flavonoids.
B) and the total polyphenols (R2 is 0.972 and 0.891, respectively). This figure is adapted from Arancibia-Avila et al. (2008).
V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701 1679
Fig. 5. Cytotoxic effect of methanol extracts from durian samples on human cancer cell lines Calu-6 (for human pulmonary carcinoma) and SNU-601 (for human gastric carcinoma):
(A) DI, durian immature; (B) DM, durian mature; (C) DR, durian ripe; (D) ORD, overripe durian.
This figure is adapted from Haruenkit et al. (2010).
hindered the rise in the plasma lipids due to cholesterol containing core. The availability is the following: in Hawaii the early crop occurs
diet: the TC to 8.7%, 16.1% and 10.3% and the LDL-C to 20.1%, 31.3% from January to April; midseason crop is from June to August, with peak
and 23.5% respectively. And also significantly hindered the decrease in July; and there is a late crop in October or November. Graviola
in plasma antioxidant activity in all diet groups (P b 0.05). Nitrogen contains carbohydrates, proteins, folic acid, calcium, phosphorus, iron,
retention remained significantly higher in Chol/Mon Thong than in vitamin C, large amounts of vitamins B1 and B2. The fruit – a white,
other diet groups. Diet supplemented with Mon Thong affected the creamy and stringy – has a unique tart taste and fresh aroma,
composition of plasma fibrinogen in rats and showed intensive reminiscent of the smell of pineapple and a good thirst quencher.
protein bands around 47 kDa. No lesions were found in the examined A. muricata (soursop) and A. squamosa (sweetsop) are edible tropical
tissue of heart and brains. Mon Thong cv. is preferable for the fruits which are common, readily available and cheap in the producing
supplementation of the diet as positively influenced the lipid, country. The moisture content of fruits was N70%. The approximate
antioxidant, protein and metabolic status. It was reported that nutritional compositions of unripe soursop and sweetsop were (%): total
durian fruit till now was not investigated extensively, therefore carbohydrates 84.8, 86.5; proteins 7.34, 7.09; lipids 1.68, 0.99; ash 4.02,
based on the results of shown study (Leontowicz et al., 2007) durian 2.28; fiber 4.33, 10.81, respectively. Contents (g/L) in ripe soursop and
cultivars can be used as a relatively new source of antioxidants. sweetsop juices were as follows: carbohydrates 12.52, 10.56; glucose
6.14, 4.32; proteins 2.91, 0.22; lipids 3.25, 1.05; fiber 0.0; citrate 8.82,
2.6. Graviola 3.53, respectively. The pH of fruit juices was acidic and the epicarp,
mesocarp and juice of both fruits contained potassium, sodium, iron,
Graviola [(Annona muricata, guanábana (Spanish), graviola magnesium, calcium, chloride and bicarbonate. The juices also con-
(Portuguese), Brazilian pawpaw, corossolier, guanavana, toge-banreisi, tained phosphorus, zinc and copper (Enweani, Obroku, Enahoro, &
durian benggala, nangka blanda, and nangka londa)] has been one of the Omoifo, 2004). The plant produces a wide range of secondary chemicals,
first fruit trees. It was imported from America in the tropical regions of some already known to be toxic, but the discovery here of the imino
the Old World and widely distributed from southeastern China to sugars as a new group of chemicals, including the neurotoxin
Australia and the warm lowlands of eastern and western. Graviola is swainsonine, raises questions about the safety of consumption of this
popular in Cuba, Bahamas, Puerto Rico, Colombia and northeastern plant (Mohanty et al., 2008). A methylene chloride extract of the pulp of
Brazil (Lorenzi et al., 2006). Fruit is oval, sometimes having an irregular A. muricata L. was fractionated and Annonaceous acetogenins (type E)
curved shape, grows to 10–30 cm in length and up to 15 cm in width, have been isolated. Previously known C-35 and C-37 mono-epoxy
and thus has a weight of 4.5–6.8 kg. The fruit is covered with mesh, unsaturated compounds, epomuricenins-A and -B (8+ 9) and epomu-
tough looking, but soft to the touch and has inedible bitter shell with lots senins-A and B (10 + 11), were obtained (Fig. 6). Two new mono-epoxy
of soft spikes. In immature fruit hull has a dark green color, and when the saturated C-35 representatives, epomurinins-A and -B (12 + 13) were
fruit ripens, it becomes slightly yellow and is easily separated from the also isolated (Melot, Fall, Gleye, & Champy, 2009). The essential oil of the
set inside the white fibrous juicy segments surrounding a soft spongy exotic fresh fruit (pulp) A. muricata (Annonaceae) from Cameroon was
1680 V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701
investigated by GC/FID and GC/MS. Esters of aliphatic acids were suffering from rheumatism, arthritis and gout. Graviola is commonly
especially dominating (total amount 51%), with 2-hexenoic acid Me promoted as a cancer treatment (Cassileth, 2008). Matrix metallopro-
ester (23.9%), 2-hexenoic acid Et ester (8.6%), 2-octenoic acid Me ester teinases (MMP) may exert important roles in both physiologic and
(5.4%), and 2-butenoic acid Me ester (2.4%) as main compounds. pathologic extracellular matrix remodeling. They have been implicated
Additionally, mono- and sesquiterpenes such as β-caryophyllene in tumoral progression of many human malignancies interfering on
(12.7%), 1,8-cineole (9.9%), linalool (7.8%), α-terpineol (2.8%), linalyl angiogenic, invasive, and metastatic events. Specifically, the gelatinases
propionate (2.2%), and calarene (2.2%) were highly concentrated in the MMP-2 and MMP-9 have been intensively studied in connection with
essential oil of the fresh fruit of A. muricata (Jirovetz, Buchbauer, & tumor invasion and metastasis, and have been considered as promising
Ngassoum, 1998). GC/MS analysis of the leaf, peel and fruit pulp oils of targets for cancer treatment. The inhibition of the MMP-2 and MMP-9
A. muricata L. showed the presence of 68 compounds of which 59 were gelatinolytic activity was investigated in Aloe vera, black tea, and
identified. The main components of the leaf oil were β-caryophyllene A. muricata aqueous extracts (AE), diluted in activation buffer (AB, with
(31.4%) and other sesquiterpenes, while the fruit oil contained calcium). It was reported that the antitumoral effects verified for A. vera,
essentially aliphatic acids and esters, in particular, methyl(E)-2- A. muricata, and black tea AE may be partially explained by their
hexenoate — 39.8% (Pelissier et al., 1994). The plant is traditionally inhibitory activity on MMP (Ribeiro et al., 2010).
used for the treatment of epilepsy, dysentery, cardiac problems,
worm infestation, constipation, hemorrhage, antibacterial infection, 2.7. Guava
dysuria, fever, and ulcer. It also has antifertility, antitumor and abort-
ifacient properties. Ethanolic extracts of leaves and stem are reported to Guava (Psidium guajava L., also known as goiaba, goiabeira), locally
have an anticancerous activity. A. squamosa has as well phyto- known as Klom sali, is an important fruit, which originated in the
pharmacological properties (Saleem et al., 2009). Graviola has very tropics of America. Guava has a globular shape, with the texture crispy
broad medicinal claims and is also widely consumed as a food and in when served raw; with sweet and sour taste, composed of 200 to
drinks in the tropics. For therapeutic purposes graviola is used in 300 g/fruit. The fruit is available all year around, as fresh, and
diseases of the colon to maintain intestinal flora. Juice of the mature fruit processed as juice. Guava has a smooth surface, round or pear-shaped
is a good diuretic, promotes weight loss and is used to treat diseases of small size. Ripe fruit should be consumed with the skin to improve
the liver, to normalize the acidity of the stomach, having anti-rheumatic digestion and to stimulate the heart. Daily consumption of guava
and anti-inflammatory properties. Such juice is necessary for people normalizes blood pressure, so is vital for the human body. When the
fruit is ripe it becomes yellow and has a bitter-sweet taste. Depending
on the type of guava pulp may be white or pink color. The fruit
O O consists of water, contains proteins, fats, calcium, phosphorus, iron,
fruit sugar, vitamin A, and fiber. Guava contains vitamin C to 5 times
more than oranges (240 mg per 100 g). The sugar content of the fruit
is combined with sweet, sour-sweet fruit, as well as dairy products.
Epomuricenin A
19
O 15 For the first time Lima, Fernandes, and Lima (2010) reported that
O O Edessa scabriventris Stal on Eugenia uniflora (Brazilian-cherry) and on
P. guajava (guava) (Myrtaceae) fruit trees have an economic value.
Guava has high antioxidant effect (Isabelle et al., 2010; Kongkachuichai,
Charoensiri, & Sungpuag, 2010). The antioxidant capacity and
Epomuricenin B phenol content of 3 tropical fruits pulps, namely, honey pineapple,
17 O 13
banana and Thai seedless guava, were studied by Alothman et al.
O O (2009). The polyphenol of Thai seedless guava was 123 to 191 mg GAE/
100 g, that of pisang mas was 24.4 to 72.2 GAE/100 g, and that of honey
pineapple was 34.7 to 54.7 GAE/100 g. High phenol content was
Epomusenin A significantly correlated with high antioxidant capacity. Three solvent
systems were used (methanol, ethanol and acetone) at three different
O 17
O concentrations (50%, 70% and 90%) and with 100% distilled water. The
O
efficiency of the solvents used to extract phenols from the 3 fruits
varied considerably (Alothman et al., 2009). Natural products have
recently become the focus of increased research interest due to their
Epomusenin B potential pharmacological activities. The acetone extracts of guava
O 15 (P. guajava L.) branch (GBA) had cytotoxic effects on HT-29 cells.
O O The GBA showed highly cytotoxic effects via the MTT reduction
assay, LDH release assay, and colony formation assay. In particular, the
250 μg/ml of GBA showed 35.5% inhibition against growth of HT-29
cells (Lee & Park, 2010). The chemical constituents from the fruit of
Epomurinin A P. guajava were reported. Nine triterpenoids, ursolic acid, 1β, 3β-
O 15
dihydroxy-urs-12-en-28-oic acid, 2α,3β-dihydroxy-urs-12-en-28-oic
O O acid, 3β,19α-dihydroxy-urs-12-en-28-oic acid, 19α-hydroxy-urs-12-
en-28-oic acid-3-O-α-L-arabinopyranoside, 3β,23-dihydroxy-urs-12-
en-28-oic acid, 3β,19α,23β-trihydroxy-urs-12-en-28-oic acid,
2α,3β,19α,23β-tetrahydroxy-urs-12-en-28-oic acid, and 3α,19α,23,24-
O 13 Epomurinin B tetrahydroxy-urs-12-en-28-oic acid were isolated by means of chroma-
tography, and their structures were elucidated on the basis of MS, 1H
NMR and 13C NMR spectra (Shu, Yu, & Wang, 2009). The chemical
Fig. 6. Several biological active acetogenins were isolated from Annona fruits (Annona
composition of mature fruits isolated from six different cultivars of guava
muricata L.). (P. guajava L.) grown in Taiwan has been studied by headspace solid-
This figure is adapted from Melot et al. (2009). phase microextraction (HS-SPME) coupled with GC–MS. A total of 35
V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701 1681
compounds were identified, including 24 terpene hydrocarbons, 2 total fat, sucrose, D-glucose, D-fructose, neutral detergent fiber, quinic
terpene alcohols, and minor constituents including 1 alcohol, 2 acid, malic acid, citric acid, ash, Na, K, Ca, Mg, Fe, Cu, Zn, Mn, and
aldehydes, 3 esters, 1 terpene ester and 2 terpene oxides. Although phosphates were detected in kiwano fruit (C. metuliferus) samples.
the volatile constituents of the six cultivars were similar, with β- Citric acid was the main organic acid and K was the main mineral
caryophyllene (47.7–58.3%) and aromadendrene (7.1–14.6%) as the element (Romero-Rodriguez, Vazquez-Oderiz, Lopez-Hernandez, &
major constituents in all cultivars, quantitative differences in the Simal-Lorano, 1992). Total polyphenol content and antioxidant
composition of some constituents were observed P. guajava L. cv. Chan- activities of non-edible parts (seed and peel) of eight tropical fruits
Shan Bar contained higher percentages of 3-hexenyl acetate, 1,8-cineole, were analyzed and compared with those of their edible parts. Total
and allo-ocimene than other species (Chen, Sheu, Lin, & Wu, 2008). polyphenol content in seed, peel and pulp ranged from 0.2 to 153, 5.0
Characterization of the aromatic profile in commercial guava essence and to 124, and 1.0 to 12 mg/g DW, respectively. Kiwano and papaya peels
fresh fruit puree by GC–MS yielded a total of 51 components quantified. showed strong ferrous ion-chelating capacity, although they did not
Commercial essence was characterized to present a volatile profile rich in have high polyphenol content and DPPH and ABTS radical scavenging
components with low molecular weight, especially alcohols, esters, and activities (Matsusaka & Kawabata, 2010). Lutein ester formation in
aldehydes, whereas in the fresh fruit puree terpenic hydrocarbons and 3- kiwano was detected (Breithaupt, Wirt, & Bamedi, 2002). Kiwano
hydroxy-2-butanone were the most abundant components. New fruits have high levels of water, vitamin C and minerals (K, Mg, and P)
components were described as active aromatic constituents in pink and low levels of glycerides. Flavonoids, which were detected,
guava fruit (3-penten-2-ol and 2-butenyl acetate) as well as known revealed high levels of rutin and small amounts of myricetin and
compounds: 3-hydroxy-2-butanone, 3-methyl-1-butanol, 2,3-butane- quercetin. The presence of high levels of rutin with antioxidant, anti-
diol, 3-methylbutanoic acid, (Z)-3-hexen-1-ol, 6-methyl-5-hepten- inflammatory, spasmolytic, capillary protective, and blood platelet
2-one, limonene, octanol, ethyl octanoate, 3-phenylpropanol, cinna- aggregation inhibitory activities may be pharmacologically important
myl alcohol, and α-copaene (Jordán, Margaría, Shaw, & Goodner, 2003). (Ferrara, 2006). Lactic, ascorbic, benzoic, salicylic, citric, tartaric,
The chemical composition of the volatile oil of guava fruits from trees fumaric, glutaric, shikimic, oxalic, caffeic, hippuric, cinnamic, malic,
grown in Nigeria was investigated by GC–MS. A total of 25 compounds, and quinic organic acids were isolated (Fig. 7) from kiwano fruits
accounting for 80% of the oil, were identified. Free fatty acids (mainly (Pero, 2006).
lauric and myristic acids) were the most abundant group of constituents
(34%). Large amounts of β-caryophyllene and O-containing sesquiter- 2.9. Kiwifruit
penes (25%) also were typical for Nigerian guava (Ekundayo, Ajani,
Seppanen-Laakso, & Laakso, 1991). A total of 88 volatiles were identified Kiwifruit (A. deliciosa) is native to Southern China. Other species of
and detected. The data showed that hydrocarbons were more Actinidia are also found in India and Japan and north into southeastern
prominent in the white fleshed guava and oxygenated compounds Siberia. Cultivation spread from China in the early 20th century, when
were predominant in the pink fruit. Myrcene, cis- and trans-ocimene seeds were introduced to New Zealand. The kiwifruit is a large,
and β-caryophyllene were the most important hydrocarbons in guava woody, deciduous vine. Kiwifruit has an oval shape, typically the size
aroma. The carbonyl compounds were the main polar group in pink of a large hen's egg, and a fibrous, dull brown-green skin, and bright
guava. The alcohols were the main polar group in white guava. Hexanal green or golden flesh with rows of tiny, black, edible seeds, soft texture
was the major abundant constituent in both cultivars. C6-aldehydes, and a unique flavor. Usually the availability is November–April. The
alcohols and esters were important aroma compounds in guava (Askar, chemical constituents of volatile oil from caudexes of A. deliciosa were
El-Nemr, & Bassiouny, 1986). extracted by distillation with water vapor, and then were separated
and identified by GC–MS. Totally 19 compounds were identified
2.8. Kiwano accounting for 97.37% of all quantity. The principal chemical con-
stituents in volatile oil were tri-Bu phosphate, bis(2-methylpropyl)
The kiwano (Cucumis metuliferus) is a member of the Cucurbita- phthalate, 3,7-dimethyl-3-hydroxy-1,6-octadiene, 2,4-bis(1,1-
ceae and like the rest of its genus, is native to Africa (in particular, dimethylethyl) phenol and trans-2-dimethyl-5-(1-methylethenyl)
Nigeria). It became acclimatized in Australia several decades ago. The cyclohexanone (Ge et al., 2008). Volatiles of kiwifruit pulp were
fruits are ellipsoids, approximately 12 cm long by 8 cm in diameter, stripped with N2, trapped on activated charcoal, eluted with CS2, and
and of a green color which during ripening changed to orange. The separated and identified by GC–MS. Major components were 2-hexenal,
cortex is covered in conical protuberances, whose tips bear sharp ethyl (Et) butanoate, and Et hexanoate. Compounds identified in kiwifruit
prickles that can easily be removed when the fruit is ripe. Internally, were Et 3-methylbutanoate, di-Et carbonate, Et 2-butenoate, 1,5-
the fruit is composed of a juicy green mucilaginous mass containing heptadiene-3,4-diol, 2,2-diethyl-1-pentanol, 7-methyl-1-octene, (E)-4-
numerous smooth white seeds. The horned melon (C. metuliferus), hexen-1-ol, 2-methylcyclopentanol, and Et octanoate (Cossa, Trova, &
also called African horned cucumber or kiwano, is an annual vine in Gandolfo, 1988).
the cucumber and melon family. The fruit of this plant is edible, but it Glycosidically bound volatiles in kiwifruit have been isolated from
is used more for decoration as for food. It has a yellow-orange skin and kiwifruit juice by absorption onto a column of Amberlite XAD-2
a lime green jelly-like flesh in the ripe stage. The availability is about followed by washing with pentane and elution with methanol. Volatiles
three and a half months in two seasons (early spring and autumn).
The horned melon is native to Africa, and it is now grown in Australia,
California, Chile, and New Zealand as well (Hutchman, 2006). COOH
Correlations among the indices of fruit ripeness Brix, Brix/total HO
acidity, soluble sugars/total acidity and color, were studied for
different fruits (whortlberry, raspberry, red and black currant,
OH
elderberry, sour cherry, babaco, feijoa, kiwano, persimmon and HO
passion fruit). The correlation between Brix/total acidity and soluble O N COOH
H OH
sugars/total acidity was high for all the fruits studied (r = 0.985),
indicating therefore a linear equation, in order to find the fruit sugar
Hippuric acid Quinic acid
content with known values of Brix and total acidity (Rodriguez,
Oderiz, Hernandez, & Lozano, 1993). Weight, length, firmness, Fig. 7. Organic acids from kiwano fruits.
degrees Brix, color, pH, total acidity, vitamin C, moisture, proteins, This figure is adapted from Pero (2006).
1682 V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701
were released by enzymic hydrolysis with β-glucosidase. Major com- capacity of ethylene-treated and non-treated fruits were reported by
ponents found and identified by GC–MS were E-hex-2-enal and Park et al. (2009). It was reported that the contents of these bioactive
benzaldehyde. Compounds not previously identified in kiwifruit include compounds determined by UV spectroscopy and fluorometry were
octan-3-ol, camphor, 4-methylbenzaldehyde, 2-hydroxybenzaldehyde, higher in ethylene-treated kiwifruit than in the non treated ones.
neral, geranial, Me 2-hydroxybenzoate, nerol, geraniol and 2- Antioxidant capacity in total polyphenol extracts of treated kiwifruit
phenylethanol (Young & Peterson, 1995). Analyses of 8 flavan-3-ols measured by FRAP and TEAC assays was significantly higher than that
(catechin, catechin gallate, epicatechin, epicatechin gallate, epigalloca- of non-treated. Correlation coefficients between polyphenols and
techin, epigallocatechin gallate, gallocatechin, and gallocatechin gal- antioxidant activity were significantly higher than between antiox-
late), 6 anthocyanins (cyanidin, delphinidin, malvidin, pelargonidin, idant activity and ascorbic acid. FRAP produced the most consistent
peonidin, and petunidin), 2 flavanones (hesperetin and naringenin), 2 measurements for ethylene-treated kiwifruit. The content of total
flavones (apigenin and luteolin), and 2 flavonols (myricetin and polyphenols, and related total antioxidant capacities by Fe(III)-TP
quercetin) were identified in more than 60 fresh fruits (Harnly et al., and ABTS significantly increased in ethylene-treated (Fig. 8B) than in
2006). Flavonols of kiwifruits (Actinidia chinensis Planch.) cultivated in the air-treated (non-treated with ethylene) kiwifruit samples
Georgia were studied. Kaempferol-3-L-rhamnoside (afzelin), kaemp- (Fig. 8A) after the first half of the treatment, starting from the 5th
ferol-3-D-glucoside (astragalin), quercetin-3-L-rhamnoside (querci- day (Fig. 8, P b 0.05). The Fe (III)-TP and ABTS values for each extract
trin), quercetin-3-D-glucoside (isoquercitrin) and quercetin-3-D- were compared and correlated with the total phenolic contents. The
gluco-L-rhamnoside (rutin) were isolated and identified (Kalandiya, relationships between the values of total polyphenol concentrations
Vanidze, Papunidze, Chkhikvishvili, & Shalashvili, 2001). Phenolic of non-treated samples vs. antioxidant capacities for Fe (III)-TP and
compounds in kiwifruit pulp were separated and characterized. ABTS were 0.8845, 0.7229, respectively. For ethylene-treated
Strongly acidic compounds were identified as derivatives of coumaric samples, the calculations showed the following order between the
and caffeic acids, including chlorogenic acid, protocatechuic acid, and a polyphenols and the antioxidant capacities determined by the two
derivative of 3,4-dihydroxybenzoic acid. The weakly acidic fraction methods: 0.9321 and 0.7423, respectively. The results are rather
contained epicatechin, catechin, and procyanidins (B3, B2, or B4 and interesting, as there is an excellent linear response, especially for the
oligomers). Flavonols were present as the glycosides of quercetin ethylene-treated samples only for Fe (III)-TP (R2 = 0.93). The overall
(glucoside, rhamnoside, and rutinoside) and kaempferol (rhamnoside estimation of the presented data showed that after ethylene
and rutinoside). Phenolic compounds were present, at levels of b1– treatment, the correlation coefficients were higher than in the non-
7 mg/L, in clarified juice (Dawes & Keene, 1999). Kaempferol-3-O-
rutinoside, kaempferol-3-O-galactoside, kaempferol-3-O-rhamnoside,
quercetin-3-O-rhamnoside, and quercetin-3-O-glucoside were isolated
from kiwifruit and mombin plum (MP). Quercetin-3-O-rhamnoside was
as the major flavonoid in kiwifruit (1.0–2.8 mg/kg) and rutin in MP (25–
120 mg/kg) (Mareck, Galensa, & Herrmann, 1990). Kiwifruit is one of A 40
the most popular fruits in the USA and Europe. However, this fruit is not 35
RSC, μMTE/g
edible even at the maturation stage due to hard firmness and high 30
acidity (Haruenkit et al., 2007; Park, 2002; Park, Jung, & Gorinstein, 25
μ
2006; Park, Jung, Kang, Deldado-Licon, Katrich, et al., 2006; Park, Jung, 20
15
Kang, Drzewiecki, et al., 2006). There are different proposals to eliminate 10
the hard firmness and high acidity of the kiwifruit (Antunes & 5
Sfakiotakis, 2002; Park, 2002), and the ethylene treatment seems 0
NT1
15
decreased significantly in the early stage of ripening simultaneously 10
with significant increase in the contents of free sugars, soluble solids, 5
endogenous ethylene production, sensory value, 1-aminocyclopropane- 0
T1
T2
1-carboxylic acid (ACC) content, ACC synthase and ACC oxidase activities,
T3
T4
T5
T6
T8
T9
T10
higher than in untreated samples (Pb 0.05). Proteins were extracted ABTS
from kiwifruit and separated by modified sodium dodecyl sulfate Ethylene-treated samples, duration
Fe(III)-TP
polyacrylamide gel electrophoresis (SDS-PAGE). The separation was
resolved into 14 protein bands. Some minor quality changes were Fig. 8. Changes in radical scavenging capacity (RSC) of total polyphenol extracts of
reported only in the 32 kDa band, which was more pronounced in the kiwifruit during 10 days of ripening, using two antioxidant tests during different periods of
treated samples. Ethylene treatment of kiwifruits was reported to time: A, RSC (μMTE/g) by ABTS and Fe(III)-TP in NT kiwifruits; B, RSC (μMTE/g) by ABTS
have positive changes in most of the studied kiwifruit bioactive and Fe(III)-TP in T kiwifruits; Abbreviations: NT, air-treated samples; T, ethylene treated
samples; ABTS, 2, 2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid); Fe (III)-TP, ferric-
compounds and to an increase in the fruit antioxidant potential tripiridyltriazine; RSC, radical scavenging capacity, expressed as mMTE (Trolox equiva-
(Park, Jung, & Gorinstein, 2006; Park, Jung, et al., 2008). The content lent)/g DW.
of the polyphenols and ascorbic acid and the radical scavenging This figure is adapted from Park et al. (2009).
V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701 1683
treated kiwifruits (Fig. 8). The ascorbic acid showed lower correla- ethanol, 3-methyl-3-buten-1-ol, 3-methyl-2-buten-1-ol, 1-hexanol,
tion of about 0.76 in comparison with 0.93 of polyphenols. During (E)-2-hexen-1-ol, 2-ethyl-1-hexanol, 1-octen-3-ol, 1-octanol, Et
ethylene treatment the bioactivity of kiwifruit is increasing and acetate, p,α-dimethylstyrene and 3-tert-butyl-4-hydroxyanisole. Al-
reaches its maximum at the 6th day and therefore it is the optimum though the volatile composition and concentration varied between
time for kiwifruit consumption; total polyphenols were the main these cultivars, the components with the highest odor activity values
contributor to the overall antioxidant activity of kiwifruit; the most (OAVs) in most cultivars were still cis-rose oxide, trans-rose oxide, 1-
sensitive test for antioxidant activities determination is FRAP. The octen-3-ol, and geraniol. Sulfur compounds usually have low contents
investigated samples showed similar protein bands during the whole to detect by MS but are responsible for garlic character of litchi flavor
period of treatment. Main protein bands appeared in the range of 20– for their extremely low odor thresholds. Excitingly two sulfur
35 kDa. The radical scavenging capacity of the kiwifruit can be used volatiles, 2,4-dithiapentane and 2,3,5-trithiahexane, were observed
for the determination of the ripening. As was mentioned, the using GC–MS and noticeably they were only detected in Guangxi
ethylene treatment of kiwifruits seems preferable (Antunes & Huaizhi, none in Guangdong Huaizhi or other cultivars. One of the
Sfakiotakis, 2002). Latocha, Krupa, Wolosiak, Worobiej, and Wilczak sulfides, 2,4-dithiapentane, was reported to present cabbage notes
(2010) compared different cultivars with kiwifruit (cv. ‘Hayward’). (Mahattanatawee, Perez-Cacho, Davenport, & Rouseff, 2007), while
The comparison was based on the amount of bioactive compounds in the other one, 2,3,5-trithiahexane, has not been noted in previous
order to evaluate their compositional characteristics, especially as a reports about litchi volatiles(Wu, Pan, Qu, & Duan, 2009). Both free
possible “healthy fruit.” The highest concentrations of vitamin C and and glycosidically-bound fractions of lychee aroma were by GC–MS.
total phenolic content (TPC), were found for Actinidia kolomikta fruit Generally, the two fractions exhibited similar volatile profiles, except
(1008.3 and 634.1 mg/100 g fresh weight [FW], respectively). for some quantitative differences. These volatile compounds were
Among phenolic compounds, seven phenolic acids and three flavo- primarily identified by their Kovats indices, using C6–C25 n-alkanes.
noids were identified. The 2,5-dihydroxybenzoic acid prevailed in Totally, 25 compounds (24 peaks) were identified in both fractions,
A. kolomikta (425.54 mg/100 g FW), while tannic acid dominated in including one ester, 14 alcohols, two aldehydes, four acids, two
other species (4.63–100.43 mg/100 g FW). The largest amounts of ketones and two terpenes. The total amounts of volatile compounds
chlorophylls and carotenoids were identified as Actinidia macro- in lychee juice in the free and bound fractions were 2907 and 1576 mg/
sperma (4.02 and 2.09 mg/100 g FW, respectively). The antioxidant kg FW of pulp, respectively. The amount of volatile compounds in the
activity (AAC) of fruit extracts decreased in the order of A. kolomikta N bound fraction was half the amount of volatile compounds in the free
Actinidia purpurea N Actinidia melanandra N A. macrosperma N Actinidia fraction, indicating that the aroma would be enriched by 50% as the
arguta N A. deliciosa according to the DPPH assay. In very recent re- volatile compounds in the bound fraction were released by enzymatic
search (Park et al., 2011) four different cultivars of kiwifruit hydrolysis (Chyau, Ko, Chang, & Mau, 2003). A large number of
(‘Hayward’, ‘Daeheung’, ‘Haenam’ and ‘Bidan’) were compared in polysaccharides were present in the pericarp tissues of harvested litchi
order to find the best for human consumption. It was registered fruits. The purified product was a neutral polysaccharide, with a
significantly highest contents (P b 0.05) of polyphenols and ascorbic molecular weight of 14 kDa, comprised mainly of 65.6% mannose,
acids in ‘Bidan’ (25.85 ± 1.3 mg GAE/g and 151.70 ± 10.4 mg/g DW, 33.0% galactose, and 1.4% arabinose. Analysis by Smith degradation
respectively). The protocatechuic and vanillic acids were the highest indicated that there were 8.7% of (1 → 2)-glycosidic linkages, 83.3% of
in ‘Bidan’ cultivars. Also the level of antioxidant activity (μM TE/g (1 → 3)-glycosidic linkages and 8.0% of (1 → 6)-glycosidic linkages in
DW) was significantly higher (P b 0.05) in ‘Bidan’ (120.82 ± 5.8, the polysaccharide (Yang et al., 2006). Two purified polyphenol
109.28 ± 11.2, 102.40 ± 6.6 and 94.43 ± 4.7 for CUPRAC, ABTS, DPPH oxidase (PPO) substrates were identified as (−)-epicatechin and
and FRAP radical scavenging assays, respectively). Pattern recogni- procyanidin A2. The results showed that (−)-epicatechin exhibited
tion techniques (cluster analysis, principal component analysis, stronger antioxidant capability than procyanidin A2, in terms of
factor analysis, and canonical discriminant analysis) were used for reducing power and scavenging activities of DPPH radical, hydroxyl
comparison of the cultivars. High correlation was found between the radical and superoxide radical. Furthermore, (−)-epicatechin content
polyphenols (R2 = 0.988), ascorbic acid (R2 = 0.988) and the anti- in pericarp tissue tended to decrease with increasing skin browning
oxidant activity in the studied cultivars. The overall bioactivity of the index of litchi fruit during storage at 25 °C. Thus, these two compounds
cultivars was as follow: ‘Bidan’ N ‘Haenam’ N ‘Daeheung’ = ‘Hayward’. can be used as potential antioxidants in litchi waste and the fresh
‘Bidan’, relatively new cultivar, can be recommended for consump- pericarp tissue of litchi fruit exhibited a better utilization value (Sun,
tion (Park et al., 2011). Jiang, et al., 2010, Sun, Seeberger, et al., 2010).
Litchi (Litchi chinensis Sonn.) is also known as Hong Hua, lychee, Longan (Dragon Eye) — the fruit of an evergreen tree longan
originated in the Kwantung province in southern China with a shape (Euphoria longana, syn. Dimocarpus longan), is a member of the
of round or oval, up to 40 mm in diameter, with a single seed in the unusual and diverse Soapberry Family (Sapindaceae), widespread in
middle of the fruit, occupies up to half of the fruit and composed of China, Taiwan, Vietnam and Indonesia. The name comes from the
approximately 50 g/fruit. Red peel needs to be removed before eaten, Vietnamese province of Longan where this plant was cultivated until
and aril is edible part. The texture is juicy, translucent aril and the now. Juicy Longana has a sweet, very fragrant, similar to the lychee
taste is sweet and slightly sour. It can be used in processed form as flavor with a unique flavor. Color solid inedible outer shell of the fruit
canned lychee in syrup. The availability of litchi is June and July. varies from spotty-yellowish to reddish. As the Chinese lychee, fruit
Sodium orthovanadate suspended in a lychee black tea decoction Longana contains a solid dark red or black seed. The following
effectively regulates blood glucose levels in rats with insulin- varieties of longan exist: Biew Kieuw, Dagelman, Diamond River,
dependent, streptozotocin (STZ)-induced diabetes (Edel et al., Kohala and Sri Chompoo. The availability of this fruit is late July to
2006). Volatile components of nine litchi cultivars (10 samples) September, according to variety. Three phenolic compounds, namely
with high compositional value from Southern China were investigated gallic acid, corilagin and ellagic acid, were identified and quantified
by means of GC–MS combined with headspace solid phase micro- using HPLC method. Compared with conventional extraction and
extraction. A total of 96 volatiles were detected, of which 43 were ultrasonic extraction samples, high pressure extraction sample
identified. Seventeen common volatiles in all the samples included exhibited higher extraction efficiency in terms of extraction yield,
linalool, cis-rose oxide, α-terpineol, β-citronellol, geraniol, p-cymene, phenolic content and antioxidant activity (De Assis et al., 2009; Prasad
1684 V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701
et al., 2010). The high pressure extraction technology provided a 2007). From the pulp of E. longana (Longan Arillus), three cerebroside
better way of utilizing longan fruit pericarp as a readily accessible molecular species have been isolated (Fig. 9). Six known cerebrosides,
source of natural antioxidants in food and pharmaceutical industries. soyacerebrosides I and II, 1-O-beta-D-glucopyranosyl-(2 S,3R,4E,8E)-2-
The phenol contents and the antioxidant activities of 12 Chinese (2′-lignoceroylamino)-4,8-octadecadiene-1,3-diol (longan cerebroside
longan cultivars were studied (He et al., 2009). The polyphenols of I) and its 8Z isomer (longan cerebroside II), momor-cerebroside I, and
longan pericarp and seed demonstrated significantly higher antiox- phytolacca cerebroside, were identified as major components of these
idant capacities than did the pulp. The ferric reducing antioxidant cerebroside molecular species. All the cerebrosides were shown to be a
powers of longan fruits were closely correlated with the polyphenol mixture of geometrical isomers (8E and 8Z) of sphingosine-type or
contents. Gallic acid and ellagic acid were not the major contributors phytosphingosine-type glucocerebrosides possessing 2-hydroxy fatty
to the antioxidant activity of longan pericarp. Other 15 phenolic acids (Ryu, Kim, & Kang, 2003). Longan fruit contains significant
profiles in longan pericarp along with a number of unknown amounts of bioactive compounds such as corilagin, ellagic acid and its
structures were revealed. The rich array of phenolic compounds of conjugates, 4-O-methylgallic acid, flavone glycosides, glycosides of
several different types in longan pericarp extract might form a quercetin and kaempferol, ethyl gallate 1-β-O-galloyl-D-glucopyranose,
synergistic multilevel defense system against oxidation (He et al., grevifolin and 4-O-α-L-rhamnopyranosyl-ellagic acid (Yang et al.,
2009). Anthocyanidins found in certain flowers have been shown to 2011-this issue). Longan (D. longan Lour.) is used as a traditional edible
act as strong antioxidants in various systems, exhibiting multiple and medicinal material in China (Zhong, Wang, He, & He, 2010). The
biological actions. The antioxidative effects of water extract and effects of polysaccharides from longan pulp with ultrasonic extraction
ethanolic extract of longan (D. longan Lour.) flowers were evaluated (UELP) on the radicals scavenging, immunity-modulatory and anti-
by radical scavenging activity and compared to those of gallic acid, tumor activities in S180 tumor mice models were investigated. UELP
myricetin, and epigallocatechin gallate. Abundant levels of phenolic with medium-dose (200 mg/kg) and low-dose (100 mg/kg) had potent
compounds including flavonoids, condensed tannins, and proantho- immune-modulatory effects in S180 tumor mice model and exhibited
cyanidins were found in water or ethanolic extracts prepared from significant effect on delayed-type hypersensitivity (DTH) response,
dried longan flowers. The results suggested that longan flower crude macrophage phagocytosis and ConA-stimulated splenocyte prolifera-
extracts, especially ethanolic extract, have antioxidant and anti- tion as compared with model control treatment (pb 0.01). The results of
inflammatory effects, and the probable mechanism involves inhibi- this report showed that UELP had great antitumor effects, and
tion of inflammation by proanthocyanidins. Preliminary observations maximum inhibition rate was obtained at medium-dose and low-dose
suggest that longan flower extract, especially alcoholic extract, could (200 and 100 mg/kg). The petroleum ether, chloroform and ethyl acetate
be another potential source of natural dietary antioxidant and anti- fractions of ethanol extract of leaf and stem from the plant Nephelium
inflammatory agent (Ho, Hwang, Shen, & Lin, 2007). Longan fruits longan (Fam-Sapindaceae) were subjected (Ripa, Haque, & Bulbul, 2010)
contain a significant amount of polyphenols (Sun, Shi, Jiang, Xue, & to antioxidant, antibacterial and cytotoxic activities. All the fractions
Wei, 2007). Polyphenols were extracted from longan pericarp tissues. showed potent antioxidant activity, of which the ethyl acetate and
Two compounds were identified as 4-O-methylgallic acid and (−)- chloroform fraction of leaf demonstrated the strongest antioxidant
epicatechin, respectively. In terms of reaction with longan polyphenol activity. Both the stem and leaf of the experimental plant have
oxidase (PPO), (−)-epicatechin was further identified as the PPO considerable antibacterial, cytotoxic and antioxidant properties which
substrate that caused longan fruit to brown. The results of antioxidant indicates that the plant have potent bioactive principles.
activity showed that 4-O-methylgallic acid had higher reducing power
and DPPH-, hydroxyl radical-, and superoxide radical-scavenging
activities than (−)-epicatechin (Sun et al., 2007). The protective effects
of fruits and vegetables against chronic diseases have been attributed to
the antioxidant properties of some secondary metabolites present in O
these foods (Rangkadilok et al., 2007). Plant polyphenols have been
reported to exhibit bioactive properties, and in particular antioxidant OH
activities. Longan seeds are found to contain high levels of some
HN
m
beneficial polyphenolic compounds such as corilagin, gallic acid and O OH
ellagic acid. The present study examined the free radical scavenging HO O
activity of longan seed extract by using three different assay methods. HO 4 R
Longan extracts contained corilagin ranging from zero to 50.64 mg/g OH
DW, gallic acid from 9.18 to 23.04 mg/g DW, and ellagic acid from OH
8.13 to 12.65 mg/g DW depending on the cultivars. Dried longan
seed extracts of cultivar Edor contained high levels of gallic and
8
ellagic acids and also exhibited the highest radical scavenging
activities when comparing fresh seed and dried pulp extracts. For Soyacerebroside I, m = 11, R =
scavenging activity of DPPH and superoxide radicals, longan seed 6
extract was found to be as effective as Japanese green tea extract while
dried longan pulp and mulberry green tea extracts showed the least Soyacerebroside II, m = 11, R =
scavenging activities. In the ORAC assay, both fresh and dried 8
6
longan seed also had higher activity than dried pulp and whole
8
fruit. However, the results demonstrate that three polyphenolics
may not be the major contributors of the high antioxidant activity Longan cerebroside I, m = 19, R =
of longan water extracts but this high activity may be due to other 6
phenolic/flavonoid glycosides and ellagitannins present in longan
fruit. In addition, longan seed also showed tyrosinase inhibitory Longan cerebroside II, m = 19, R =
activity with IC50 values of 2.9–3.2 mg/ml. Therefore, the preliminary 8
6
observations suggest that longan seed extract could be another
potential source of potent natural dietary antioxidants and also in Fig. 9. Cerebrosides isolated from the pulp of Euphoria longana (Longan Arillus).
an application as a new natural skin-whitening agent (Rangkadilok et al., This figure is adapted from Ryu et al. (2003).
V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701 1685
OH
OH
O
O OH
HO OH
OH
HO O OH
O O
Mangiferin
O O
O Z O
Violaxanthin dibutyrate
absorption spectra, thin layer chromatography, and HPLC (Bunsiri, IC50 values ranging from 1.24 to 91.07 μM (Jiang et al., 2010). The crude
Ketsa, & Paull, 2003; Zadernowski et al., 2009). In vitro studies on the ethanol extract (CEM) of the fruit hull of G. mangostana L. contains
contents of polyphenols, antioxidant potentials and protein profiles in oxygenated and prenylated phenol derivatives, such as xanthones or
Mangosteen and then in vivo their influence on plasma lipids and xanthen-9H-ones, and is used by people in Southeast Asia as a
antioxidant activities in rats fed cholesterol supplemented diet traditional medicine for the treatment of abdominal pain, dysentery,
showed that this fruit has high antioxidant properties (Leontowicz wound infections, suppuration, and chronic ulcer. α-Mangostin, and γ-
et al., 2006; Leontowicz et al., 2007). The diets of the Chol/Durian, mangostin in each dose dependently demonstrated the ability to
Chol/Snake, and Chol/Mangosteen groups were supplemented with scavenge reactive oxygen species. CEM and mangostins possess potent
5% of these fruits, respectively (Haruenkit et al., 2007). It was found peripheral and central antinociceptive effects in mice and suggest that
that diets supplemented with durian, and to a lesser degree with xanthones may be developed as novel analgesics and anti-inflammatory
snake fruit and mangosteen, significantly hindered the rise in plasma drugs (Cui et al., 2010).
lipids and the decrease in antioxidant activity. The nutritional values
were comparably high. Five xanthones were isolated and identified
2.14. Passiflora
(Zhao et al., 2010) as isonormangostin, garcinone E, 7-0-methyl-
garcinone E, 1,6-dihydroxy-7-methoxy-8-(3-hydroxy-3-methylbutyl)-
6′, 6′-dimethyl-4′, 5′-dihydropyrano[2′,3′:3,2]xanthone(IV), 3- Passiflora (Passiflora edulis) is a Brazilian passion fruit or
isomangostin from the pericarp of G. mangostana (Fig. 11). Several granadilla, peyshn, passion fruit and ripe fruit is with greenish-
xanthone and benzophenone compounds such as epicatechin, 1,3,7- brown skin and juicy yellow-orange flesh, one of the most delicious
trihydroxyxanthone, egonol, α-mangostin, β-mangostin, γ-mangostin, varieties of passion fruit. Passion fruit is a yellow-orange or dark
neosmitilbin, and garcinone E were isolated from G. mangostana. These purple fruit, oval in shape and size of about 6–12 cm. The availability
isolates possess strong inhibitory activity of fatty acid synthase with the for passion fruit is spring through late summer (May to October). The
varieties are the following: Panama, Possum Purple, Sweet Sunrise
and Quadrangularis. The preferred fruits are with smooth shiny skin,
but are sweeter with a rough, chapped skin. Known names include
Granadilla (South America), Lilikoi (Hawaiian), Magrandera Shona
OH O OH (Zimbabwe), Maracuja (Brazil), Passion Fruit (UK and US), Passion-
O OH fruit (Australia and New Zealand), Pasiflora (Israel), Parchita
RO (Venezuela), and Lac tien, Chanh day or Chanh leo (Vietnamese). It
is cultivated commercially in frost-free areas for its fruit and is widely
O OH grown in Australia, Caribbean, California, Colombia, Brazil, Ecuador,
HO O OH
OH East Africa, Indonesia, India, Israel, Haiti, Hawaii, Florida, Mexico, New
Zealand, Peru, Sri Lanka, and South Africa. The volatile oil was extracted
α-Mangostin, R = Me
γ-Mangostin, R = H
from P. edulis. The main constituents were 2,4-dimethy-heptane
Gartanin (35.13%), trans-cinnamaldehyde (16.71%), trans-anethole (12.52%), α-
cubebene (11.45%). The results gave basis for total exploration of
P. edulis Sims seeds (He, Liu, Huang, Lin, & Sun, 2010). A comparison
O OH among different passion fruit species has been established in terms of
O O RO qualitative and semi-quantitative differences in volatile composition. By
MeO using the optimal extraction conditions and GC–MS it was possible to
tentatively identify seventy one different compounds in passiflora
HO O OH
species: 51 volatiles in P. edulis Sims (purple passion fruit), 24 in P. edulis
HO O OH
Sims f. flavicarpa (yellow passion fruit) and 21 compounds in Passiflora
1-Isomangostanin Garcinone E mollissima (banana passion fruit). It was found that the ethyl esters
comprise the largest class of the passion fruit volatiles, including 82.8%
Fig. 11. Several xanthones isolated from Garcinia mangostana. in P. edulis variety, 77.4% in P. edulis Sims f. flavicarpa variety and 39.9% in
This figure is adapted from Zhao et al. (2010). P. mollissima. Among the identified compounds, only 5 volatiles were
V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701 1687
OH cases). The methanol extracts of fresh and dried persimmon using the β-
carotene/linoleate model system have shown 91% and 88% of
OH antioxidant activity, respectively. The best correlation was found
between polyphenols, β-carotene, DPPH and nitric oxide values (R2
ranges between 0.95 and 0.99). The differences of dietary fibers,
O minerals and trace elements in fresh and dried persimmons are not
OH
significant; the contents of polyphenols and the level of the antioxidant
O potentials are higher in fresh persimmons than in dried fruits; however,
both variables are also high in dried persimmons; when fresh fruits are
not available, proper dried persimmons could be used as a valuable
HO substitute. Gorinstein, Bartnikowska, et al. (1998) investigated the effect
O of dietary persimmon (Pers, 7.0%) on lipid metabolism and antioxidant
activity in 40maleWistar rats adapted to cholesterol-free or 1%
cholesterol diets. The experiment lasted 4 wk In the Chol/Pers vs. Chol
HO O
group, the persimmon-supplemented diet significantly (P b 0.05)
OH OH lessened the rise in plasma lipids due to dietary cholesterol: total
cholesterol (TC) (3.88 vs. 4.88 mmol/L; 220%), LDL cholesterol (LDL-C)
(2.24 vs. 3.27 mmol/L; 231%), total triglycerides (TG) (0.72 vs.
0.89 mmol/L; 219%), lipid peroxides (LP) (2.20 vs. 3.25 mmol/L; 232%)
and TC in liver (32.8 vs. 49.9 mmol/g; 234%), (Pb 0.001). The Chol/Pers
diet significantly reduced the decrease in HDL phospholipids (HDL-PH)
due to dietary cholesterol (0.73 vs. 0.58 mmol/L; 225.8%, P b 0.001) and
OH decreased the level of total phospholipids (TPH) (1.32 vs. 1.73 mmol/L;
223%, P b 0.001). These results demonstrate that persimmon possesses
hypolipidemic and antioxidant properties that are evident when
Phenolic metabolite persimmon is added to the diet of rats fed cholesterol. These properties
Fig. 13. Novel phenolic compound 4,8-dihydroxy-6-methyl-1-naphthalenyl 6-O-β-D- are attributed to its water-soluble dietary fiber, carotenoids and
xylopyranosyl-β-D-glucopyranoside was isolated from Diospyros kaki. polyphenols (Gorinstein, Bartnikowska, et al., 1998). Another study
This figure is adapted from Gondo et al. (1999). compares the hypolipidemic and antioxidant effects of two diets in rats
fed cholesterol (Gorinstein et al., 2000) and shows that both diets
fortified with 7% of whole dry persimmon and with 7% of phenol-free
steam-distillated under reduced pressure before and after the removal dry persimmon improve lipid levels. But only diet supplemented with
of astringency. At least 9 out of 23 volatile compounds which were whole persimmon exerts an antioxidant effect. Therefore, the antiox-
isolated and identified including n-BuOH, 3-Me butanol, n-hexanol, (Z)- idant effect of this fruit is associated mainly with persimmon phenols
3-hexen-1-ol, 2-Me hexanol, acetoin, and AcOH were common to the 3 and not with the persimmon fiber. Another study in vivo compared two
cultivars. The degree of quality change in the volatile compounds during diets supplemented with 7% of dry persimmon peel and dry persimmon
treatment differed depending on the cultivar; it was the largest in pulp (Gorinstein, Kulasek, et al., 1998) in rats fed cholesterol. A diet
Yokono and the smallest in Hiratanenashi (Taira, Ooi, & Watanabe, fortified with dry persimmon peel is more efficient than the same diet
1996). Persimmon bioactivity was compared with some other fruits fortified with dry persimmon pulp. Therefore the persimmon peel
(Gorinstein, Zemser, Haruenkit, et al., 1999; Gorinstein et al., 1994; showing the effectiveness of its antioxidant activity can be used by
Gorinstein et al., 2001). Fluorometric analysis was used to compare the individual consumers and in industrial processing. The nutraceutic
contents of phenolics in two cultivars of persimmon: seedless ‘Triumph’ value of persimmon (D. kaki Thunb. cv. Triumph) and its influence on
and seed contain ‘Fuio’. It was reported that seedless Triumph possess some indices of atherosclerosis were studied in vitro (fibers, poly-
significantly higher amount of total phenolics and that the main phenols, and phenolic acids) and in experiment on rats fed cholesterol-
component was p-coumaric acid (Gorinstein et al., 1994). Fluorometry containing diet (Park, Jung, Kang, Delgado-Licon, Ayala, et al., 2006;
and atomic absorption spectrometry following microwave digestion Park, Leontowicz, et al., 2008). Addition of persimmon to the diets did
were reported for the determination of major phenolics and minerals not affect diet intake, its efficiency or body weight gains of rats. Diets
and show that total, soluble, and insoluble dietary fibers, total phenols, supplemented with whole fruit positively influenced some indices of
epicatechin, gallic and p-coumaric acids, and concentrations of Na, K, atherosclerosis in serum of rats fed a cholesterol-containing diet: it
Mg, Ca, Fe, and Mn in whole persimmons, their pulps, and peels were hindered the rise of lipid levels and the decrease in the antioxidant
significantly higher than in whole apples, pulps, and peels. Conversely, activity (Park, Jung, Kang, Delgado-Licon, Ayala, et al., 2006; Park,
the contents of Cu and Zn were higher in apples than in persimmons. In Leontowicz, et al., 2008). Other persimmon cultivars (‘Fuyu’ and ‘Jiro’)
persimmons and apples all of the above components were higher in were compared with cv. ‘Triumph’ in vitro and in vivo studies. ‘Fuyu’ was
their peels than in whole fruits and pulps. The relatively high contents of more effective than ‘Jiro’ in the contents of polyphenols, flavonoids,
dietary fibers, total and major phenolics, main minerals, and trace flavanols, tannins, carotenoids, ascorbic acid and antioxidant potentials.
elements make persimmon preferable for an antiatherosclerotic diet Supplementation with 5% of the lyophilized Fuyu and Jiro hindered the
(Gorinstein et al., 2001). Persimmon is not all year around fruit, increase in plasma lipids vs. the Chol group (total cholesterol 19.4% and
therefore it was suggested to use persimmon in dry form (Jung et al., 9.5%, low-density lipoprotein cholesterol 25.6% and 13.1%, respectively,
2005; Park, Jung, Kang, Delgado-Licon, Ayala, et al., 2006). Different P b 0.05) and hindered the decrease in plasma antioxidant activity vs. the
methods of persimmon drying were studied (Jung et al., 2005; Park, Chol group by 40.0% and 16.8% and by 39.6% and 11.3% for the ABTS and
Jung, Kang, Delgado-Licon, Ayala, et al., 2006), sun-drying during DPPH assays, respectively. The atherosclerotic lesions in the aortas of the
1 month and dehydration at 60 °C during 12 h. Total polyphenols in Chol/Fuyu and Chol/Jiro groups were significantly less than in the Chol
fresh persimmons were higher than in dried fruits (1.3 vs. 0.9 and group (Pb 0.05) during a period of 47 d (42 d of feeding and 5-d
0.8 mg/100 g FW, respectively). The percentages of inhibition were adaptation before the experiment). The histological investigation of
higher in fresh fruit than in dried one (70% vs. 59% and 55% and 58% vs. aortas showed that the Chol containing diet led to changes in the aorta.
53% and 46%, for DPPH and ABTS radicals, respectively) (Pb 0.05 in all The highest concentration of lesions was in the arch of aorta (Fig. 14I).
V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701 1689
The Chol diet group showed the greatest aortic changes compared with 2.16. Pineapple
the control diet and the groups supplemented with persimmon
(Fig. 14II). Electrophoresis of the proteins from rats' liver tissue reported Pineapple (Ananas comosus Merr.), known as Queen variety,
changes in 14-kDa bands after persimmon supplementation. A shift in Phuket, is native to South America and has now spread throughout
maximum wavelengths in three-dimensional fluorescence of serum the tropical world. It is a big fruit of about 1 to 2 kg/fruit, conical with a
protein fractions after persimmon supplementation was found in crown; texture is juicy and fibrous; and the taste is sweetened sour.
comparison with the control group and an increase in fluorescence The fruit is used as fresh and processed (canned juice or canned slices,
intensity compared with the Chol groups (Gorinstein, Leontowicz, et al., jam, and glaze) and available all year around. Pineapple cultivars are
2011). Primary metabolites (sugars, organic acids) and secondary divided into five groups. It was reported that two types of the fruit
metabolites (phenolics and carotenoids) were quantified by HPLC in were investigated: the smooth Cayenne, which is characterized by
fully ripe fruit of 11 kaki cultivars Amankaki, Cal Fuyu, Fuji, Hana Fuyu, pale yellow to yellow flesh, and the Queen, which is characterized by
Jiro, O'Gosho, Tenjin O'Gosho, Thiene, Tipo, Tone Wase and Triumph deep yellow flesh (Gorinstein, Zemser, Vargas-Albores, et al., 1999).
(Veberic, Jurhar, Mikulic-Petkovsek, Stampar, & Schmitzer, 2010). Tone The phenolic contents of the extracts as caffeic acid equivalents were
Wase stands out as the richest in sugars, particularly glucose, and found to be the highest in methanol (51.1%), followed by ethyl acetate
cultivars Tipo and Triumph contained the highest amounts of organic (13.8%) and water extract (2.6%). Antioxidant capacity of the extracts
acids. Cultivars O'Gosho, Cal Fuyu and Hana Fuyu contained the least as equivalent to ascorbic acid (μmol/g DW) was in the order of
sugars and cultivar ‘Jiro’ the least organic acids. Catechin and gallic acid methanol extract N ethyl acetate extract N water extract. In comparison
were present in the highest concentration. The predominant carotenoid with butylated hydroxyanisole (BHA), at 100 ppm of concentration,
in both skin and pulp of ripe persimmon fruit was β-carotene. The the antioxidant and free radical scavenging activities of the extracts
highest content was measured in skin of cultivar Hana Fuyu, which also assayed through β-carotene-linoleate and DPPH method were also
contained the highest level of total carotenoids. In persimmon pulp, found to be the highest with methanol extract followed by ethyl
much lower values for carotenoids were obtained in fruit of cultivar Cal acetate and water extracts. The results indicated that the extent of
Fuyu (Gondo et al., 1999; Taira et al., 1996). antioxidant activity of the extract is in accordance with the amount of
Fig. 14. (I) Aortic changes in the (A) control, (B) control/Fuyu, (C) control/Jiro, (D) Chol, (E) Chol/Fuyu, and (F) Chol/Jiro groups. The positions marked with arrows show the most
concentrated area and the percentages of lesions in the arch of the aorta from the total amount. (II) Changes in lesions in the total aorta (percentage of Chol). Chol, cholesterol.
This figure is adapted from Gorinstein, Leontowicz, et al. (2011).
1690 V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701
phenolics present in that extract and the pineapple fruit being rich in cardenolides and bufadienolides, flavonoids, tannins, anthraquinones
phenolics may provide a good source of antioxidant (Hossain & and cyanogenic glycosides. Findings of this experimental research
Rahman, 2011). The antioxidant content of fruit was compared as pre- showed that flavonoids, tannins, cardenolides, bufadienolides and
packed fresh-cut vs. whole fruit (Opara & Al-Ani, 2010). The obtained alkaloids were present in the exocarp of star apple (C. cainito). The
results of the contents of phenolic compounds in peel, core and pulp exocarp of papaya (C. papaya) contains saponins, tannins, cardenolides
of pineapple by HPLC showed that there were four phenolic and bufadienolides while the exocarp of pineapple (A. comosus)
compounds in the peel of pineapple: gallic acid, catechin, epicatechin has flavonoids, saponins, tannins, cardenolides and bufadienolides
and ferulic acid. While in pulp and core of pineapple, only low (Gundran et al., 2001). Bromelain, a pharmacologically active
concentrations of epicatechin and ferulic acid were detected (Yi, Wei, compound, is present in stems and fruits of pineapple (endowed
Teng, & Gao, 2006). Among the 187 isolated volatile components of with anti-inflammatory, anti-invasive and anti-metastatic properties).
Philippine pineapple were identified the following: 2,5-dimethyl-4- The antitumor-initiating effects of bromelain in mouse skin tumori-
methoxy-3(2H)-furanone, Me 3-(methylthio)propanoate, and γ- genesis model were reported (Bhui, Prasad, George, & Shukla, 2009).
hexalactone were accounting for approximately 55% of the total Pre-treatment of bromelain resulted in reduction in cumulative
volatiles. In addition, 11 sulfur-containing compounds were found in number of tumors per mouse. The basis of antitumor-initiating activity
the aroma extract, including 8 components newly identified such as of bromelain was revealed by its time dependent reduction in DNA
Me S–Me thiomalonate and Et 5-(methylthio)pentanote. The estima- nick formation and increase in percentage prevention. Modulation of
tion on the sensory relevance of volatiles by AEDA indicated 2,5- inappropriate cell signaling cascades driven by bromelain is a coherent
dimethyl-4-hydroxy-3(2H)-furanone, 2,5-dimethyl-4-methoxy-3 approach in achieving chemoprevention (Bhui et al., 2009).
(2H)-furanone, γ-octalactone, 3-(methylthio)propanal, and Me S–
Me thiomalonate as the major odor-active components of Philippine 2.17. Rambutan
pineapple aroma (Akioka, 2008). One hundred and eighteen volatile
compounds from fresh pineapple pulp were identified according to Rambutan (Nephelium lappaceum L.), known as Rongroen, is
their retention time on polar and apolar capillary columns and their native to Malaysia. Shaped as bright-red oval fruit is about the size of
mass spectra. These compounds were divided as follow: seven hydro- a small hen's egg with a seed, hairy peel with long, soft spines, aril is
carbons (3.3%), nine sulfur compounds (10.3%), 42 esters (44.9%), 10 edible part; with the texture of juicy, translucent aril and the taste —
lactones (11.5%), 11 carbonyl compounds (4.7%), 14 acids (7.3%), 11 sweet with a tasty acid pulp. The processed rambutan is canned
alcohols and phenols (3.8%), and 14 miscellaneous components in syrup. The availability is from June through August. Over 100
(14.3%). Four compounds were found at a level higher than 1 mg/ volatile compounds from the red-skinned cultivar of rambutan, Jitlee
kg, Me octanoate (1.49 ppm), Me 3-(methylthio) propanoate (N. lappaceum L.), a tropical fruit native to Southeast Asia, were
(1.14 ppm), Me hexanoate (1.1 ppm) and 3-methyl-2,5-furandione detected by GC/MS. Sixty compounds in the extracts had some odor
(1.07 ppm), three others were detected at a level between 0.5 ppm activity. The 20 most potent odorants included β-damascenone, (E)-
and 1 ppm, and 25 compounds at a level between 0.1 ppm and 4,5-epoxy-(E)-2-decenal, vanillin, (E)-2-nonenal, phenylacetic acid,
0.5 ppm. From the reported 118 compounds, 71 have already been cinnamic acid, Ethyl 2-methylbutyrate, and δ-decalactone. β-
described in the literature to be present in pineapple aroma (Teai, Damascenone, Et 2-methylbutyrate, 2,6-nonadienal, (E)-2-nonenal,
Claude-Lafontaine, Schippa, & Cozzolino, 2001). Sixty-seven free and nonanal were detected as the main compounds among the fruit
volatiles of pineapple var. perolera were identified with Me 2–Me aroma (Ong, Acree, & Lavin, 1998). The peel of N. lappaceum
butanoate, Me hexanoate, Me 4-acetoxy-hexanoate, Me 5-acetoxy- possesses antioxidant properties. Methanolic and aqueous extracts
hexanoate and Me 3-methyl-thiopropanoate as major components. of lyophilized rambutan peels and seeds were evaluated for phenolic
Total 2,5-dimethyl-4-hydroxy-3(2H) furanone (DMHF) (free and contents, antioxidant and antibacterial activities (Thitileadecha,
glycosidically bound) in pineapple were detected in the juice of Teerawutgulrag, & Rakariyatham, 2008). High amounts of phenolic
crushed pineapple with EtOAc after treatment with almond β- compounds were found in the peel extracts and the highest content
glucosidase (Wu et al., 1990). Glycosidically 17 bound aroma was in the methanolic fraction (542.2 mg/g dry extract). The peel
compounds (aglycons) were also identified. These aglycons mainly extracts exhibited higher antioxidant activity than the seed extracts
consisted of phenolic compounds, carboxylic acids and furanic in all methods determined. The methanolic fraction was found to be
compounds of which coniferyl alcohol, hexadecanoic acid, furaneol the most active antioxidant as shown by their 50% DPPH center dot
and 4-vinylguaiacol are the most representative (Sinuco, Morales, & inhibition concentration, 4.94 μg/ml. This fraction exhibited higher
Duque, 2004). Several sterols were detected in the juices of pineapple, DPPH center dot radical scavenging activity than BHT and ascorbic
passion fruit and the two citrus fruits, orange and grapefruit such as: acid (0.32 g dry extract/g BHT or ascorbic acid). All peel extracts
β-Sitosterol, Stigmasterol, Citrostadienol, Campesterol, Isofucosterol, exhibited antibacterial activity against five pathogenic bacteria. The
Stigmast-4-en-3-one, Valencene, Nootkatone and Ergostanol. Ergos- most sensitive strain, Staphylococcus epidermidis, was inhibited by
tanol and stigmastanol were found to be the sterol markers for the methanolic extract (MIC 2.0 mg/ml). Experiments on the
pineapple juice, while passion fruit juice was characterized by the isolation and identification of the active constituents were con-
presence of an unidentified but unique sterol referred to as compound ducted, and on their antioxidant activity using a lipid peroxidation
C. Juices of orange and grapefruit yielded very similar sterol profiles inhibition assay. The methanolic extract of N. lappaceum peels
(Ng & Hup, 1998). Tokitomo, Steinhaus, Buttner, and Schieberle exhibited strong antioxidant properties. The isolated compounds
(2005) showed that 12 selected odorants revealed the following (Fig. 15) were identified as ellagic acid (EA), corilagin, and geraniin.
compounds as key odorants in fresh pineapple flavor: 4-hydroxy-2,5- These compounds accounted for 69.3% of methanolic extract, with
dimethyl-3(2H)-furanone (HDF; sweet, pineapple-like, caramel-like), geraniin (56.8%) as the major component, and exhibited much
ethyl 2-methylpropanoate (fruity), ethyl 2-methylbutanoate (fruity) greater antioxidant activities than BHT in both lipid peroxidation
followed by methyl 2-methylbutanoate (fruity, apple-like) and 1- (77–186 fold) and DPPH (42–87 fold) assays. The results suggest that
(E,Z)-3,5-undecatriene (fresh, pineapple-like). The phytochemical the isolated ellagitannins, as the principal components of rambutan
screening was conducted in order to detection the biological active peels, could be further utilized as both a medicine and in the food
compounds present in the exocarp of papaya (Carica papaya), industry (Thitilertdecha, Teerawutgulrag, Kilburn, & Rakariyatham,
pineapple (A. comosus), and star apple (Chrysophyllum cainito). 2010). The rind of rambutan, which is normally discarded was found
These bioactive compounds which have shown remarkable impor- to contain extremely high antioxidant activity when assessed using
tance in the field of medicine are the following: alkaloids, saponins, several methods. Although having a yield of only 18%, the ethanolic
V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701 1691
HO OH HO OH
HO OH
O O
O
O O
O O
O O
OH Fig. 16. New cultivar of Snake fruit Sumalee.
The figure is taken by S. Gorinstein in 2009 in the house of one of the growers in orchard
O O (Muang district, Chantaburi province, Thailand).
O O
Salak (S. edulis), snakes on a fruit — a fruit tree plant palm family
O HO OH (Arecaceae, Palmae, and Palmaceae) (Fig. 16). The snake fruit in
Thailand — sala, rakum, in Malaysia and Indonesia — salak, with a
diameter of 3–4 cm, weight 50–100 g. The fruit is with an oval shape
HO OH OH (the ends are elongated). It has a size of a kiwifruit with a scaly brown
rind that is easily removed. The beige flesh consists of one or several
O segments. The fruit is distributed mainly in Southeast Asia. The season
Geraniin in Thailand and Malaysia is from June to August, in Indonesia — all
year round. It is popular in Indonesia and Malaysia, and the fruit is
Fig. 15. Geraniin is the major component isolated from rambutan (Nephelium rarely found in other countries. It is believed that the most delicious
lappaceum). fruits grow in Bali and around Yogyakarta in Java. The findings (Ikram
This figure is adapted from Thitilertdecha et al. (2010). et al., 2009) showed that fruits (58 underutilized fruits of 32 different
species from 21 genera) of Pometia, Averrhoa, Syzygium, Sallacca,
Phyllanthus, Garcinia, Sandoricum and Maipighia had higher antioxi-
rambutan rind extract had a total phenolic content of 762 ± 10 mg dant activity compared to other studied genera. Among the under-
GAE/g extract, which is comparable to that of a commercial prep- utilized fruits, Sandoricum and Phyllanthus contained the highest total
aration of grape seed extract. Comparing the extract's prooxidant phenolics (N2000 mg/100 g edible portion). The study indicated that
capabilities with vitamin C, α-tocopherol, grape seed and green tea, some of these underutilized fruits have the potential to be sources of
the rind had the lowest prooxidant capacity. In addition, the extract antioxidant components. Forty-six volatile constituents of the salak
at 100 μg/ml was seen to limit oxidant-induced cell death (DPPH at fruit (Wong & Tie, 1993) were identified by GC–MS and 1H NMR
50 μM) by apoptosis to an extent similar to that of grape seed. The which Me esters of branched-chain alkenoic and β-hydroxy acids
extracts were not cytotoxic to normal mouse fibroblast cells or predominated and terpenoids were completely absent. The most
splenocytes while the powderized rind was seen to have heavy metal abundant components were Me 3-hydroxy-3-methylpentanoate
contents far below the permissible levels for nutraceuticals. These (25.0%) and Me (E)-3-methylpent-2-enoate (23.4%). A total of 24
findings for the first time reveal the high phenolic content, low pro- odor-active compounds from three cultivars of snake fruits (Pondoh
oxidant capacity and strong antioxidant activity of the extract from Hitam, Pondoh Super, and Gading) were freshly extracted and
rind of N. lappaceum. This extract, either alone or in combination associated with the aroma of snake fruit. Me 3-methylpentanoate
with other active principles, can be used in cosmetic, nutraceutical was regarded as the character impact odorant of typical snake fruit
and pharmaceutical applications (Palanisamy et al., 2008). The aroma. 2-Methylbutanoic acid, 3-methylpentanoic acid, and an un-
ability of ethanolic N. lappaceum L. rind extract to act as anti- known odorant with very high intensity were found to be responsible
hyperglycemic agent was reported. Geraniin, an ellagitannin, was for the snake fruit's sweaty odor. Other odorants including Me 3-
identified as the major bioactive compound isolated from the etha- methyl-2-butenoate (overripe fruity, ethereal), Me 3-methyl-2-
nolic N. lappaceum L. rind extract. In addition to its extremely high pentenoate (ethereal, strong green, woody), and 2,5-dimethyl-4-
antioxidant activity and low prooxidant capability, geraniin pos- hydroxy-3(2H)-furanone (caramel, sweet, cotton candy-like) contribute
sesses in vitro hypoglycemic activity (alpha-glucosidase inhibition: to the overall aroma of snake fruit. The main differences between the
IC50 = 0.92 μg/ml and alpha-amylase inhibition: IC50 = 0.93 μg/ml), aroma of Pondoh and Gading cultivars could be attributed to the olfactory
aldol reductase inhibition activity (IC50 = 7 μg/ml) and has the ability attributes (metallic, chemical, rubbery, strong green, and woody), which
to prevent the formation of advanced glycation end-products (AGE). were perceived by most of the panelists in the Pondoh samples but were
Geraniin was observed to exhibit these properties at more significant not detected in the Gading samples (Wijaya, Ulrich, Lestari, Schippel, &
levels compared to the positive controls acarbose (carbohydrate Ebert, 2005). The compounds of 3β-hydroxy-sitosterol and 2-methy-
hydrolysis inhibitor), quercetin (aldol reductase inhibitor) and green lester-1-H-pyrrole-4-carboxylic acid were isolated from ethyl acetate
tea (AGE inhibitor). Geraniin (Fig. 15) has the potential to be extract of snake fruit (S. edulis Reinw) cv. Bongkok (Fig. 17). Inhibition of
developed into an anti-hyperglycemic agent. These findings also xanthine oxidase by the two compounds was evaluated against enzyme
strongly support the use of a geraniin-standardized N. lappaceum of xanthine oxidase. 3β-Hydroxy-sitosterol could be regarded as
extract in the management of hyperglycemia (Palanisam, Teng, inactive, while 2-methylester-1-H-pyrrole-4-carboxylic acid was found
Manaharan, & Appleton, 2011). to be active with IC50 value of 48.86 μg/ml (Priyatno, Sukandar, Ibrahim,
1692 V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701
Fig. 18. A, Box and dot plots of the frequency distribution of the snake fruit, and two kiwifruit samples: conventional ‘Hayward’ (CHE) and organic ‘Hayward’ ethylene treated;
B, Principal component analysis of FRAP parameters of snake fruit (S), kiwifruit OHE (Ko) and kiwifruit CHE (Kc) extracts (5–25 mg/ml).
This figure is adapted from Gorinstein et al. (2009).
V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701 1693
Fig. 18A show the frequency distribution of the snake fruit, and two additional tool for the characterization of the polyphenol extracts during
kiwifruit samples: conventional ‘Hayward’ ethylene treated (CHE) and different stages of ripening and different exotic fruits cultivars
organic ‘Hayward’ ethylene treated (OHE). The antioxidant activities correspond with the previous data (Gorinstein et al., 2011-this issue;
(μMTE/g DW) were determined according to FRAP assay in the wide- Gorinstein et al., 2010). The results revealed that polyphenol extracts
ranking interval of fruit extract concentrations from 5 to 25 mg/ml. FRAP caused the fluorescence quenching of BSA by the formation of
data vary widely and all box plots have approximately the same polyphenol–BSA complex.
variation (Gorinstein, Leontowicz, et al., 2011). There is a degree of
resemblance between these two kiwifruits (CHE and OHE), but the 2.19. Star fruit
largest similarities exist between snake and kiwifruits. It was shown
that 3D-FL spectrum provides the change in the conformation of The star fruit or carambola (Averrhoa carambola) is a tropical fruit
proteins (Fig. 19). The main peak (Fig. 19A) of bovine serum albumin that is gaining popularity in the United States. This fruit acquired its
(BSA) at λ em/ex = 340/280 was quenched in the presence of name from the five pointed star shape when cut across the middle of
methanol extracts of studied exotic fruits, (example of snake fruit), the fruit. It has a waxy, golden yellow to green color skin with a
as well as in the presence of pure catechin as a standard. Different complicated flavor combination that includes plums, pineapples, and
proportions of polyphenols and BSA were investigated. The strongest lemons. The following varieties of this fruit are Arkin, Fwang Tung,
intensity (Fig. 19D) was for BSA at extract:BSA (1:1) and the lowest Kari, and Sri Kembangan. The juicy fruits are yellow inside when ripe
(Fig. 19C) for extract:BSA (5:1). The decrease in the fluorescence and have a crisp texture and when cut in cross-section are star shaped.
intensity (Fig. 19E) showed the conformation of the BSA changes in The fruits have an oxalic acid odor, which varies between plants from
the presence of extracts. There are few publications on applications strong to mild, the taste also varies from very sour to mildly sweetish.
of 3D fluorescence spectra (Shi et al., 2010; Zhang, Chen, Zhou, & Wang, Each fruit may have up to twelve 6–12.5 mm long seeds, which are
2009), therefore the conclusions that 3-D fluorescence can be used as an flat, thin and brown. The flowers are often produced year round under
Fig. 19. The contour map (C, D) displayed a view of the corresponding three dimensional fluorescence (A, B) spectra (3-D FL). The 3-D FL were with emission from 270 to 750 nm and
the excitation wavelengths from 260 to 500 nm, scanning speed was 1000 nm/min, emission mode and fluorescence intensity till 1000. Abbreviations: A–D on axis X: Em.
Wavelength, emission wavelength; Y: excitation wavelength, all the fluorescence intensity values were from − 100 to 1000. 3D-FL spectra: A, snake fruit methanol extract:
BSA = 5:1; B, snake fruit methanol extract:BSA = 1:1; contour map spectra: C, snake fruit methanol extract:BSA = 5:1; D, snake fruit methanol extract:BSA = 1:1. E, Two dimensional
fluorescence spectra of the complex BSA-polyphenol: upper line, BSA with fluorescence intensity units (FIU) of 843; middle line, extract:BSA = 1:1 with FIU of 782; lower line,
estract:BSA = 5:1 with FIU of 705; bovine serum albumin, BSA. The main peak is at λem/ex = 340/280 nm.
1694 V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701
tropical conditions. The availability is August–March. Carambola (star juice drink processing, was found to contain much higher antioxidant
fruit) is a popular tropical fruit consumed fresh or as juice. Carambola activity than the extracted juice using several methods for assessing
is one of two species in the genus Averrhoa (family Oxalidaceae), the antioxidant activity. The residue accounted for around 70% of total
other species is Averrhoa bilimbi. A. carambola or star fruit is a juicy antioxidant activity (TAA) and total polyphenolic contents, however
tropical fruit grown in Thailand and throughout Southeast Asia (Shui only contributed 15% of the weight of whole fruit. Freeze-dried
& Leong, 2004a, 2004b). residue powder, which accounted for around 5% of total weight, had
The optimized extraction conditions for total phenolic contents total polyphenolic content of 33.2 ± 3.6 mg GAE/g sample and total
(TPC) of star fruit residues using response surface methodology (RSM) antioxidant activity of 5270 ± 468 and 5152 ± 706 mg TEAC/g sample
are with acetone (60%), during 180 min, at 40 °C. The highest TPC ABTS and DPPH scavenging assays, respectively. HPLC/MS shows that
values of star fruit residues were 2366.71, 2436.03, and 2510.95 mg major proanthocyanidins in star fruit were different from their
GAE/100 g DW, respectively. The results showed that the acetone isomers in pyconogenol. The high content of phenolics and strong
concentration was statistically the most significant factor (p b 0.01) antioxidant activity of residue extracts indicate that residue powder
and the optimal extraction conditions obtained were: acetone may impart health benefits, when used in functional food products.
concentration, 65.34%; extraction temperature, 43.18 °C; and extrac- The residue extracts should also be regarded as potential nutraceutical
tion time, 233.51 min. The experimental TPC was 965.65 ± 30.87 mg resources in future. It was found that among 96 detected volatile
GAE/100 g DW, which was well matched with the predicted value, components from the pericarp of star fruit, l-Phenyl dodecane and l-
965.52 mg GAE/100 g DW (Yap et al., 2009). Phenyl undecane were the major identified hydrocarbons (17% and
Phytochemical studies on the leaves and fruits of A. carambola 11% respectively). The oxygenated constituents were dominated by a
yielded anthraquinones, flavone C-glycosides, anthocyanins and mixture of aldehydes (14%), among which cyclohexyl octadecanal
dihydroabscisic alcohols. Recently, it was reported the isolation of (8%) was the major one. The crude protein content was 11% on DW
two new alkyl phenols, 2,5-dimethoxy-3-undecylphenol and 5- bases. The amounts of vitamin C and β-carotene reached 28 mg/100 g
methoxy-3-undecylphenol, together with two known benzoqui- and 623 μg/100 g, respectively, while α-tocopherol and vitamin D
nones, 5-O-methylembelin and 2-dehydroxy-5-O-methylembelin were not detected. The major minerals were potassium (222 mg/
(Araho et al., 2005; Xu et al., 2004; Chakthong, Chiraphan, Jundee, 100 g) and calcium (41 mg/100 g). The tannin content was 1.04% on
Chaowalit, & Voravuthikunchai, 2010). It was indicated that star fruit DW. The alcohol extract exhibited anti-inflammatory, antipyretic,
is a very good source of natural antioxidants, and it was reported the analgesic, anticonvulsant, antioxidant, hypolipidemic and hypoglyce-
identification of compounds that contribute to total antioxidant mic activities of variable potency as compared to referred drugs. In
activity in star fruit using HPLC and MS (Fig. 20). The major addition, both the alcohol extract and the volatile constituents exerted
antioxidants were initially attributed to singly-linked proanthocya- significant antimicrobial activities on selected bacteria and fungi (El
nidins that existed as dimers, trimers, tetramers and pentamers of Alfy, Tadros, Ibrahim, & Sleem, 2004). The fruit is a good source of
catechin or epicatechin (Shui & Leong, 2004a, 2004b). The toxic effect natural antioxidants (Pino, Marbot, & Aguero, 2000). The major
of star fruit juice at different storage conditions in Sprague Dawley antioxidants are phenolic compounds, such as gallic acid (in
(SD) rats (Khoo, Teh, Rao, & Chin, 2010; Chakthong et al., 2010) was gallotannins), catechin, or epicatechin. Folk medicine in India uses
evaluated. Increment of ALT levels (P b 0.05) was reported in those the ripe fruits to halt hemorrhages and dried fruits or juices to
rats treated with A. carambola juice stored for 3 h. It was concluded counteract fever; jams may mitigate liver problems, diarrhea, and
that A. carambola juice stored for 0 h and 1 h are safe to be consumed. hangover after excessive alcohol consumption. In Brazil, carambola is
However, juice stored for 3 h exerts toxic effect on rat liver at used as a diuretic and for treatment of eczema, but in patients on dialysis
hepatocellular level. Pre-treatment of mice with the fruit extract of the consumption of carambola fruits can lead to altered consciousness.
A. carambola significantly reduced serum levels of alkaline phosphates The constituents responsible for these effects remain uncertain, but
(ALP), aspartate aminotransferase (AST), and alkaline phosphates carambola contains large amounts of oxalate which can induce brain
(ALP), enzyme and significantly increased the liver reduced glutathi- functions depression and stroke. In addition some bioactive compounds,
one levels 24 h after the administration of carbon tetrachloride. A such as glycine, L-alanine, L-serine, L-aspartic acid, L-glutamic acid,
marked improvement in the enzyme activities and the liver reduced thiamin, niacin, L-valine, L-threonine, citric acid, riboflavin, tartaric,
glutathione level was observed in the pre-treated mice 4 days after succinic, fumaric, oxalic acids, proline, α-ketoglutaric, and malic acids.
the administration of carbon tetrachloride. Histopathological studies Volatile components of star fruit were isolated by simultaneous steam
provided supportive evidence for the biochemical analysis. The distn./solvent extn. Fifty-six components were identified (8.9 mg/kg), of
aqueous extract of the fruit of A. carambola has hepatoprotective which the major ones were butyl acetate, ethyl decanoate and
effect against carbon tetrachloride induced liver damage in mice hexadecanoic acid. Star fruit (A. carambola L.) is a very good source of
(Azeema, Mathew, Dilip, & Nair, 2010). It was reported (Shui & Leong, natural antioxidants. The major antioxidants were initially attributed to
2006) that the residue of star fruit, which is normally discarded during singly-linked proanthocyanidins that existed as dimers, trimers,
tetramers and pentamers of catechin or epicatechin (Ferrara, 2009).
evaluated. Wax apple fruit skin disks from different fruit development E
stages incubated with and without sucrose showed differential effects
on diameter, weight, soluble solids (SSs) and skin color. Diameter, OR
weight and chlorophyll content declined, while SSs and anthocyanin
concentrations increased in a sucrose medium. Both SS and
anthocyanin concentrations in the sucrose-added disks were higher
HO
than in the non-sucrose controls. Fruits from the rapid growth stage to R=H
red stage, i.e. from 4 to 8 weeks after anthesis, had greater
anthocyanin induction in the presence of sucrose. Temperature has
R = Me
pronounced effects on quality attributes of wax apple fruit disks. R = Et
Anthocyanin and total soluble solid (TSS) were the greatest in the R = CO(CH2)nCH3
20 °C treated disks under constant temperatures. In the slow-increase
and fast-increase treatments, quality attributes in disk were better in n = 14-24
treatments with a final temperature of 25 °C than of 30 °C.
Pigmentation of disks exposed to high temperature treatment was Z
worse than in uncultured controls. Both protein and FAA concentra- OR
tions decreased after culture. Among the 5 different day/night
temperature combinations, disks under 25/20 °C had the highest
anthocyanin and TSS concentrations, while those under 30/15 °C had
the worst (Pan & Shu, 2007). Changes in the quality of stored wax HO
apple were evaluated during storage at 100 °C and ambient
temperature. The wax apple fruits were packed using stretch film R=H
wrapping and low density polyethylene (LDPE) bag. Unwrapped R = CO(CH2)nCH3
fruits were treated as control. Changes in fruit quality were evaluated
at two days interval at both storage temperatures. Observation was n = 14-24
made on color, firmness, weight loss, moisture loss, disease infection,
pH, TTA, TSS, total sugars and vitamin C. However, the ethylene level Fig. 21. Unusual phenolic fatty acid esters of monolignols isolated from wax apple fruits.
at ambient storage increased which probably related to the early This figure is adapted from Whitaker et al. (2001).
yellow to deep-yellow color pulp had the highest carotenoid content. fiber (TDF), and pectin ranged from 7.5 to 188.8 mg/100 g, 0.9 to 7.2 g/
Durian, pomelo, guava and ripe banana were good sources of flavonoids, 100 g, and 0.20 to 1.04 g/100 g, respectively. The antioxidant activities,
pomelo (Thong dee and Tuptimsayam variety) showed the greatest TSP, TAA, TDF, and pectin were influenced by cultivar (papaya, guava,
total flavonoid content (13,994.21 and 15,094.99 μg/100 g edible por- and dragon fruit) and ripening stage (papaya and/or mango).
tion). Data in this study reported that Thai fruits are not only a good Antioxidant activity showed high correlations with levels of TSP
source of dietary fiber but also a good source of carotenoids and compounds (r = 0.96), but low correlations with levels of ascorbic
flavonoids (Kongkachuichai et al., 2010). The ethanol extracts from 24 acid (r= 0.35 and 0.23 for ORAC and DPPH data, respectively). The
samples plant species commonly found in Thailand were reported and antioxidant activities evaluated by both ORAC and DPPH showed
compared on their antioxidant activity by ABTS assay (Tachakittirungrod, similar trends where red guava and carambola exhibited the highest and
Okonogi, & Chowwanapoonpohn, 2007). The ethanol extract from the sapodilla and green papaya exhibited the lowest levels. Guava and mamey
leaves of guava (P. guajava) showed the highest antioxidant capacity with sapote exhibited the highest TDF and pectin levels (Mahattanatawee et al.,
the TEAC value of 4.908±0.050 mM/mg, followed by the fruit peels of 2006). The highest content of vitamin C between the 10 exotic fruits from
rambutan (N. lappaceum) and mangosteen (G. mangostana) with the Brazil (abiu, acerola, wax jambu, cashew, mamey sapote, carambola or
TEAC values of 3.074±0.003 and 3.001±0.016 mM/mg, respectively. star fruit, Surinam cherry, longan, sapodilla and jaboticaba) of 1525 mg/
The methanol fraction possessed the highest antioxidant activity, 100 g pulp occurred in acerola. The total phenol content was higher in
followed by the butanol and ethyl acetate fractions, respectively. The abiu, acerola, Surinam cherry and sapodilla. In relation to antioxidant
hexane fraction showed the lowest antioxidant activity. The results activity, acerola has showed the great values in all three different methods
demonstrated that the mechanism of antioxidant action of guava leaf tested. The sample concentration also influenced its antioxidant power
extracts was free radical scavenging and reducing of oxidized in- (De Assis et al., 2009).
termediates. The phenolic content in guava leaf fraction played a A total of 27 fruit pulps, obtained in the Singapore markets, were
significant role on the antioxidant activity via reducing mechanisms tested for their general antioxidant capacity based on their ability to
(Tachakittirungrod et al., 2007). The potential of fruit waste materials, scavenge 2,2′-azino-bis-(3-ethylbenzthiazoline-6-sulfonic acid)
from peels of eight kinds of fruits commonly consumed and grown in (ABTS) free radical. According to the ascorbic acid equivalent
Thailand, as sources of powerful natural antioxidants, was antioxidant capacity (AEAC) values of binary extract solution of fruits
reported (Okonogi, Duangrat, Anuchpreeda, Tachakittirungrod, & in the ABTS model, chiku shows the highest antioxidant capacity,
Chowwanapoonpohn, 2007). Results from ethanolic fruit peel extracts followed by strawberry, plum, star fruit, guava, seedless grape, salak,
of DPPH and ABTS radicals showed that the top three markedly high free mangosteen, avocado, orange, solo papaya, mango, kiwifruit, cempe-
radical-scavenging power was from the peel extracts of Punica granatum dak, pomelo, lemon, pineapple, apple, foot long papaya, rambutan,
(pomegranate), N. lappaceum (rambutan), and G. mangostana (mango- rambutan king, banana, coconut pulp, tomato, rockmelon, honeydew,
steen). The IC50 values to quench the DPPH free radicals of these three watermelon and coconut water. The ascorbic acid contribution to
extracts were 0.003, 0.006, and 0.023 mg/ml and the trolox equivalent AEAC of fruits varied greatly among species, from 0.06% in chiku to
antioxidant capacity (TEAC) values from ABTS assay were 4.066, 3.074, 70.2% in rambutan (Leong & Shui, 2002). Among the thirty-eight fruits
and 3.001 mM/mg, respectively. The extract of mangosteen peel commonly consumed in Singapore tested guava had the highest
showed moderate toxicity to Caco-2 cells and high toxicity to peripheral ascorbic acid (AA)/g FW, durian and mangosteen were high in
blood mononuclear cells (PBMC) with the IC50 values of 32.0 and 4.9 μg/ tocopherols and tocotrienols. As fruits are a rich source of diverse
ml, respectively. Peel extract of rambutan exhibited extremely high antioxidants, efforts to promote consumption of a variety of fruits
value of IC50 (N100 μg/ml) against both cell types indicating non-toxic should be continued for public health benefits (Isabelle et al., 2010).
activity to the cells. The peel of rambutan may be considered potentially The volatile composition of selected Brazilian exotic fruits (Brazilian
useful as a source of natural antioxidants for food or drug product cherry (E. uniflora), acerola (Malpighia glabra L., M. punicifolia
because of its high antioxidant activity and non-toxic property to L., Malpighia emarginata DC.), jackfruit (Artocarpus heterophyllus), star
normal cells (Okonogi et al., 2007). Chen et al. (2010) compared the fruit (A. carambola) and fruits from the genera Annona (cherimoya,
content of vitamin C in 7 kinds of southern fruit, included litchi, mango, soursop, and sugar apple) and fruits from the genera Spondias
pawpaw, actinidia, banana, musa, pitaya: actinidia was the highest, (S. purpurea, S. mombin and S. tuberosa)) was reviewed (Bicas et al.,
banana was the lowest (1.86 mg/100 g). Six (sub) tropical fruits (guava, 2011-this issue). The comparison of volatile compounds of different
red pitaya, white pitaya, green mango, ripe mango and immature Citrus exotic fruits is important for flavor industry, which uses different aroma
grandis Osbeck) and two leaves (C. grandis Osbeck and guava) from Jeju compounds for the formulation of fragrances and flavorings to be
Island of Korea were evaluated for antiproliferative activities (Cho, applied in foods, cosmetics and perfumes (Bicas et al., 2011-this issue).
2010). The total antioxidant capacity (TAC) of 32 fruits purchased from Major of the total 43 volatiles in longon (Lansium domesticum Corr. var
three local markets in Pingtung country was divided into four groups: Dongon) were 1,3,5 trioxane, (E)-2-hexenal, 3-carene, α-cubebene,
the first group, containing the highest antioxidant capacity isoledene, δ-selinene, and α-calacorene. Major volatiles mangosteen
(N10 mM TE/g), included Szjou persimmon, durian, strawberry, guava (G. mangostana L. var Native) were 2, 2-dimethyl-4-octanal, E-2-hexenal,
and pomegranate. The second group, (5–10 mM TE/g), included benzaldehyde, (Z)-3-hexen-1-ol, hexyl-n-valerate, 1,4-pentadiene, and
atemoya, sweet cherry, passion-fruit, delicious apple, granny smith 2-methyl-1, 3-buten-2-ol. Volatile compounds durian (D. zibethinus L. var
apple, carambola, kiwifruit, golden kiwifruit and Fuji apple. The third Mon Thong) consisted of a large number of sulfur-containing com-
group, (3–5 mM TE/g), included shaddock, sweet orange, nectarine, pounds, which included diethyltrisulfide, diethyldisulfide, dithiolane, di-
Indian jujube, ponkan, pitaya (red pulp), banana, tomato, wax apple, Me sulfide, and 3-methyl-thiozolidine. Nonsulfur compounds 2-Me
papaya and fuyu persimmon. The fourth group, (b3 mM TE/g), include butanoate, butanedioic acid, and propyl-2-ethylbutanoate were
pitaya (white pulp), melon, pineapple honeydew melon, grape, sand also abundant. Isocitonellol, 3-hydroxy-2-butanone, pentanal, and 4-
pear and watermelon (Lang & Ke, 2006). Fourteen tropical fruits from tridecyl valerate were most abundant in ‘Rong-rien’ rambutan
south Florida (red guava, white guava, carambola, red pitaya (red (Laohakunjit, Kerdchoechuen, Matta, Silva, & Holmes, 2007). The
dragon), white pitaya (white dragon), mamey sapote, sapodilla, lychee, volatile constituents in total, 48, 39, 61 and 44 constituents were
longan, green mango, ripe mango, green papaya, and ripe papaya) were identified in rambutan (N. lappaceum L.), pulasan (N. ramboutan-ake
evaluated for bioactive compounds. Total soluble phenolics (TSP), ORAC (Labill.) Leenh.), longan (D. longan Lour.) and mata kucing (D. longan
and DPPH radical scavenging activity assays ranged from 205.4 to ssp. malesianus Leenh.), respectively (Wong, Wong, Loi, & Lim, 1996).
2316.7 g GAE/g puree, b0.1 to 16.7 μmol TE/g puree, and 2.1 to 620.2 μg Among rambutan volatiles, aliphatic alcohols (49.0%), sesquiterpenoids
GAE/g puree, respectively. The total ascorbic acid (TAA), total dietary (20.5%) and carbonyl compounds (19.5%) predominated, 2-methylbut-
V.M. Dembitsky et al. / Food Research International 44 (2011) 1671–1701 1697
3-en-ol (21.9%) and β-caryophyllene (10.4%), constituting the major Aliaa, A. R. N., Mazlina, M. K. S., Taip, F. S., & Abdullah, A. G. L. (2010). Response surface
components. In contrast, pulasan fruit yielded mainly aliphatic optimization for clarification of white pitaya juice using a commercial enzyme.
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alcohols (19.4%). Esters (68.4%) and terpenoids (27.1%) were quantita- of selected tropical fruits from Malaysia, extracted with different solvents. Food
tively the most significant among longan volatiles, and ethyl acetate Chemistry, 115, 785−788.
Andreasen, M. F., Christensen, L. P., Meyer, A. S., & Hansen, A. (2000). Content of
(66.2%) and (E)-β-ocimene (26.7%) were clearly dominant. Mata kucing phenolic acids and ferulic acid dehydrodimers in 17 rye (Secale cereale L.) varieties.
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51± 1 mg gallic acid equivalents (GAE)/100 g in the mango-peach Antioxidant properties of durian fruit as influenced by ripening. LWT — Food Science
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antioxidants for food or drug products was discussed. Exotic fruits are Alkyl phenols from the wood of Averrhoa carambola. Chinese Chemical Letters, 21,
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a rich source of antioxidants, therefore efforts to promote consump-
Chang, Y. J., Chung, M. Y., Tseng, M. N., Chu, C. C., & Shü, Z. H. (2003). Developmental
tion of a variety of fruits should be continued for public health benefits stages affect characteristics of wax apple fruit skin discs cultured with sucrose—
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dogs using a film dressing of polysaccharide extracted from the hulls of durian (Durio
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The corresponding author (S. G.) is thankful to Prof. Anderson de Chen, H. C., Sheu, M. J., Lin, L. Y., & Wu, C. M. (2008). Volatile constituents of six cultivars of
Souza San't Ana for his support and initiative in writing this review. mature guava (Psidium guajava L.) fruits from Taiwan. Acta Horticulturae, 765, 273−277.
Chen, F., & Wang, X. (2008). Fruit flavors and their health benefits. Abstracts of
The authors are thankful to Dr. Elena Katrich (School of Pharmacy,
Papers, 236th ACS National Meeting, Philadelphia, PA, United States, August 17–21,
Hebrew University of Jerusalem) for her assistance in determination AGFD-065.
of antioxidant activity and 3D fluorescence. The authors are thankful Chidambara, M., Kotamballi, N., Jayaprakasha, G. K., & Patil, B. S. (2010). Citrus
to the Chantaburi Salacca Grower Association, Chantaburi, Thailand, monoterpenes and its metabolites inhibit human prostate cancer cells. Abstracts of
Papers, 239th ACS National Meeting, San Francisco, CA, United States, AGFD-38.
for the donation of fruit samples. Cho, S. K. (2010). Characterization of bioactive compounds of selected (sub)tropical fruits
and leaves grown in Jeju and their antiproliferative effects on human cancer cells
through apoptosis. Abstracts of Papers, 240th ACS National Meeting, Boston, MA,
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