Research Article

Received: 31 March 2014 Revised: 2 July 2014 Accepted article published: 10 September 2014 Published online in Wiley Online Library: 25 September 2014

(wileyonlinelibrary.com) DOI 10.1002/jsfa.6884

Influence of pH, concentration and light on

stability of allicin in garlic (Allium sativum L.)
aqueous extract as measured by UPLC
Haiping Wang,* Xixiang Li,* Xinyan Liu, Di Shen, Yang Qiu, Xiaohui Zhang
and Jiangping Song

Abstract
BACKGROUND: Garlic is one of the most important bulb vegetables and is mainly used as a spice or flavoring agent for foods. It
is also cultivated for its medicinal properties, attributable to sulfur compounds, of which allicin is the most important. However,
the stability of allicin in garlic extract is not well understood. In this study, using UPLC, the stability of allicin extracted in water
from garlic was evaluated in phosphate buffer at different temperatures under light and dark conditions.

RESULTS: At room temperature, allicin in aqueous extract was most stable at pH 5–6 but degraded quickly at lower or higher pH.
It began to degrade within 0.5 h and was not detectable after 2 h when the pH was higher than 11 or lower than 1.5. It degraded
quickly when the temperature was higher than 40 ∘ C and especially higher than 70 ∘ C. At room temperature, allicin in water
could be stored for 5 days without obvious degradation. Higher concentrations of allicin in solution were somewhat more stable
than low concentrations.

CONCLUSION: Allicin extract was sensitive to pH and temperature of storage but not to light. Higher-concentration allicin
solution was more stable.
© 2014 Society of Chemical Industry

Keywords: garlic; allicin; ultra-performance liquid chromatography; stability

INTRODUCTION a longer time because of the lower pH of vinegar. In some areas,

Garlic (Allium sativum L.) is one of the most important bulb veg- farmers use aqueous extract of garlic as an antiseptic by spraying
etables and is mainly used as a spice or flavoring agent for foods. it on forage to feed animals.22 However, these positive properties
It is also cultivated for its medicinal properties, attributable to sul- are reduced because of the unstable character of allicin. The sta-
fur compounds such as allicin.1,2 Allicin was discovered by Chester bility of allicin is affected by its environment. Once it is generated,
John Cavallito and John Hays Bailey in 19443 and then other allicin readily changes into other compounds when it is exposed to
scientists.4,5 Allicin is present throughout the garlic plant, with the adverse temperatures or solutions. Thus cooking, aging or other-
highest levels being found in extracts from whole green garlic, fol- wise processing garlic causes allicin to be decomposed into other
lowed by shoot and leaf extracts.6 However, the root bulb is consid- compounds.23,24 It will degrade when subjected to high temper-
ered to be the most important source of allicin. Crushing of garlic atures or high-pH solutions.25,26 Previous studies based on bio-
produces high but variable amounts of allicin ranging from 16.1 to logical and chemical assays demonstrated that allicin extracts are
130.3 g kg−1 dry weight.7 unstable and degrade quickly at high temperature.27,28 Although
Allicin has been found to have numerous antimicrobial prop- the stability of allicin in aqueous extract at different temperatures
erties. The inhibitory activity of old extract of garlic is similar to from −80 to 42 ∘ C has been studied,6,25,27 the half-life of pure allicin
that of pure allicin, and fresh extract of garlic inhibits pneumolysin and natural allicin in aqueous extract has not been reported con-
hemolytic activity at lower concentrations.8 Many previous stud- sistently. The half-life of allicin in water at 23 ∘ C reported by Fuji-
ies on animals, plants and humans have described the antifungal sawa et al.27 was four times shorter than that reported by Lawson
and antibacterial activities of allicin.9 – 15 Other research has shown and Gardner.26 Besides, the stability of allicin in aqueous extract
that allicin from garlic might be effective in some areas of clinical at higher temperatures has not been well studied. Moreover, the
practice.16 – 18
In recent years a number of reports have appeared showing
bacteriostatic activity of garlic aqueous extracts.19 – 21 Aqueous ∗ Correspondence to: Haiping Wang; Xixiang Li, Institute of Vegetables and
extracts of garlic are widely used in daily life, especially in China. For Flowers, Chinese Academy of Agricultural Sciences, Beijing 100081, China.
e-mails:wanghaiping@caas.cn and lixixiang@caas.cn
example, aqueous extract of garlic is used in flour for dumplings, a
very popular food in China. Some people like to make kimchi using Institute of Vegetables and Flowers, Chinese Academy of Agricultural Sciences,
1838

garlic with vinegar, which is thought to retain the allicin in garlic for Beijing 100081, China

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Stability of allicin in garlic aqueous extract www.soci.org

stability of allicin is affected strongly by the pH of the solution.29 will degrade very quickly within a few minutes and thus typical
Owing to its instability in the acid environment (pH 1.2–2) of gas- HPLC will be unsuitable. In this study, using the UPLC method, the
tric fluid, allicin might degrade when passing through the stomach stability of allicin in aqueous extract at different concentrations,
before it reaches blood and other tissues, so it is doubtful whether temperatures, pH values and light conditions was investigated.
it contributes to any antithrombotic or blood-thinning actions in
the body.30 Thus it is of scientific interest to understand which
pH is most suitable for allicin. Whether other factors such as con-
centration and light will affect the stability of allicin has not been MATERIALS AND METHODS
reported yet. Reagents
To quantify allicin by typical high-performance liquid chro- Allicin standard solution (1100 mg L−1 ) was purchased from Chro-
matography (HPLC), it takes a run time of about 12 min.6 In madex (Irvine, CA, USA). Acetonitrile, methanol (HPLC grade) and
previous work we developed a stable, quick ultra-performance other reagents were obtained from Merck (Darmstadt, Germany),
liquid chromatography (UPLC) method that can detect allicin except for formic acid, which was purchased from DIMA Technol-
efficiently in a much shorter time of about 3 min.2 This could ogy (San Dimas, CA, USA). Monosodium phosphate and disodium
help us to understand the stability of allicin in aqueous extracts phosphate were purchased from Fisher Scientific (Fair Lawn, NJ,
under extreme environments, i.e. at high temperatures (>70 ∘ C) USA). Water was purified through a Milli-Q water purification sys-
or in highly acid (pH >10) or alkaline (pH <2) solutions, where it tem (Bedford, MA, USA).

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Figure 1. Chromatograms of (a) allicin standard and (b) sample. Peaks are at 0.95 min retention time.

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 www.soci.org H Wang et al.

Preparation of garlic aqueous extract (a)

The garlic variety ‘De Zhou Hong Pi’ (National Germplasm Repos- 120 Original pH1 pH2 pH3

Residul ratio of Allicin in solution (%)

pH4 pH5 pH6 pH7
itory for Vegetatively Propagated Vegetables, Beijing, China) was pH8 pH9 pH10 pH11

used in all experiments. Allicin was extracted from lyophilized gar- 100
lic cloves according to the method of Wang et al.2 Garlic cloves
were peeled to remove the dry protective layers, kept at −20 ∘ C 80
for 3–4 h and chopped into small slices. The garlic slices were
arranged in a thin layer, held at −80 ∘ C for 3–7 h until frozen 60
to dryness, ground to powder and passed through a 400-mesh
sieve. Two replicates of 400 mg of garlic powder were accurately 40
weighed into individual 50 mL centrifuge tubes, and 15 mL of cold
water was pipetted into each tube. The tubes were immediately 20
capped and shaken vigorously for 15 s, then another 15 mL of cold
water was added to each tube and mixed for 30 s. The tubes were 0
centrifuged at 8000 × g for 10 min at 4 ∘ C. Each supernatant was fil- 0 0.5 1 3 5 7 9 120 360 480 720
tered through a 0.45 μm Millipore filter into a vial before injection. Time (h)
The original mix extracts of the two tubes were used for the fol- (b)
lowing experiments. Firstly, the allicin concentration of the original 120 Original pH1 pH2 pH3

Residul ratio of Allicin in solution (%)

pH4 pH5 pH6 pH7
mix extracts was evaluated by the UPLC method described below. pH8 pH9 pH10 pH11
Secondly, the original mix extracts were diluted with purified 100
water to concentrations of 9.03, 6.02 and 3.01 mg L−1 to assess the
effects of temperature and light on the stability of allicin. Thirdly, 80
the original mix extracts were diluted with monosodium phos-
phate and disodium phosphate to concentrations of 9.03, 6.02 and 60
3.01 mg L−1 to assess the effects of pH on the stability of allicin.
40

Quantitative analysis of allicin

20
The content of allicin was determined by UPLC as described
by Wang et al.2 UPLC analysis was performed with a Waters
0
Acquity UPLC system controlled by Waters Empower soft- 0 0.5 1 3 5 7 9 120 360 480 720
ware. Samples were evaluated on a UPLC BEH C18 column Time (h)
(2.1 mm × 50 mm, 1.7 μm particle size) with a mobile phase con-
(c)
sisting of methanol/water (50:50 v/v) at a constant flow rate of 120 Original pH1 pH2 pH3 pH4
Residul ratio of Allicin in solution (%)

pH5 pH6 pH7 pH8 pH9

0.2 mL min−1 . The run time was set to 3 min. The column was kept pH10 pH11 pH12
at 28 ∘ C and the sample chamber at 4 ∘ C. Allicin was detected at a 100
UV wavelength of 254 nm.
A stock solution of standard allicin was diluted with 1 mL L−1 80
formic acid to obtain a series of concentrations (510, 255, 170,
127.5, 51, 10.2 and 20.4 mg L−1 ). A linear equation was constructed 60
between peak areas and allicin concentrations. Concentrations of
allicin in aqueous extracts were calculated from this equation. 40

pH effects on allicin stability 20

A series of phosphate buffers with pH ranging from 1.5 to 11 was
prepared with monosodium phosphate and disodium phosphate. 0
0 0.5 1 3 5 7 9 120 360 480 720
As mentioned above, the original aqueous extracts were diluted
Time (h)
to concentrations of 9.03, 6.02 and 3.01 mg L−1 . Samples (three
replicates for each treatment) were kept at a temperature of 25 ∘ C Figure 2. Stability of allicin in aqueous extract as a function of pH at
and the stability of allicin was evaluated at 0, 0.5, 1, 3, 5, 7, 9, 120, (a) high (9.03 mg L−1 ), (b) medium (6.02 mg L−1 ) and (c) low (3.01 mg L−1 )
concentrations. Data are mean of three replicates. Error bars denote ± SE.
360, 480 and 720 h. The stability of allicin was assessed using UPLC
and quantitatively determined as described above. The residual
ratio of allicin in solution was calculated as follows: Temperature effects on allicin stability
The stability of allicin at various storage temperatures was evalu-
residual ratio (%) = [(initial concentration ated at concentrations 9.03, 6.02 and 3.01 mg L−1 . Samples (three
– detected concentration ) replicates for each treatment) were stored in the dark at −20, 4, 25,
] 40, 55, 70 and 80 ∘ C and the stability of allicin in aqueous extracts
∕initial concentration × 100 was evaluated after 0.5, 1, 1.5, 2, 3, 5, 7, 9, 120, 360, 480 and
720 h. For −20 ∘ C, replicate samples were aliquoted and stored
The allicin degradation fitted curve and half-life were calculated in injection tubes, which were allowed to thaw for 20 min before
1840

in R software.27 evaluation. For 4 and 25 ∘ C, samples were placed in incubators.

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Table 1. Half-life of allicin as a function of pH, temperature (T, ∘ C), concentration and exposure to light

Treatment Conc. Half-life (h) Treatment Conc. Half-life (h)

pH original L 266.80 ± 6.29 pH 2 L 20.18 ± 0.95

M 382.86 ± 18.12 M 28.90 ± 1.33
H 400.75 ± 9.21 H 35.07 ± 0.23
pH 11 L 0.46 ± 0.02 pH 1.5 L 0.13 ± 0.00
M 0.50 ± 0.02 M 0.13 ± 0.01
H 0 .57 ± 0.01 H 0.14 ± 0.00
pH 10 L 1.76 ± 0.04 T −20 L 4711.01 ± 27.69
M 1.85 ± 0.05 M 7593.98 ± 100.73
H 2.05 ± 0.03 H 8111.29 ± 3.02
pH 9 L 54.15 ± 2.43 T4 L 1278.01 ± 51.37
M 61.12 ± 5.12 M 1689.81 ± 11.42
H 71.65 ± 3.58 H 1981.55 ± 83.63
pH 8 L 98.33 ± 2.00 T 25 L 266.80 ± 6.29
M 105.35 ± 4.75 M 382.86 ± 18.12
H 159.77 ± 7.41 H 400.75 ± 9.21
pH 7 L 101.70 ± 5.24 T 40 L 1.72 ± 0.11
M 134.99 ± 4.47 M 2.08 ± 0.12
H 147.32 ± 9.00 H 2.45 ± 0.17
pH 6 L 357.07 ± 6.42 T 55 L 0.73 ± 0.06
M 374.31 ± 10.76 M 0.90 ± 0.06
H 402.75 ± 12.86 H 1.08 ± 0.09
pH 5 L 350.28 ± 2.28 T 70 L 0.44 ± 0.03
M 380.22 ± 15.66 M 0.52 ± 0.05
H 400.22 ± 7.17 H 0.58 ± 0.02
pH 4 L 235.37 ± 8.74 T 80 L 0.16 ± 0.00
M 281.23 ± 11.08 M 0.20 ± 0.03
H 339.73 ± 3.39 H 0.25 ± 0.01
pH 3 L 39.61 ± 1.86 Light H 394.15 ± 10.73
M 45.51 ± 1.43 Dark H 399.93 ± 8.40
H 55.42 ± 1.02

Data are mean ± standard error (SE) of three replicates. H, high concentration (9.03 mg L−1 ); M, medium concentration (6.02 mg L−1 ); L, low
concentration (3.01 mg L−1 ).

For 40, 55, 70 and 80 ∘ C, samples were kept in water baths. Allicin Allicin stability in acid and alkaline solutions
residual ratio, degradation fitted curve and half-life calculations The decrease in allicin stability varied with storage time, concentra-
were made as above. tion and pH (Fig. 2). The stability of allicin in different pH solutions
showed a consistent trend at all three concentrations of 9.03, 6.02
and 3.01 mg L−1 . Allicin stability in aqueous extract was highest
Light effects on allicin stability in solutions of pH 5–6, with no obvious degradation for 5 days,
but decreased sharply in solutions above pH 11 or below pH 1.5,
At 25 ∘ C storage temperature and high allicin concentration
where complete degradation was observed within 2 h. The stabil-
(9.03 mg L−1 ), three replicate samples were kept in an incubator
ity of allicin in the original aqueous extract was similar with that
and the stability of allicin in aqueous extract to light was evaluated
in solutions of pH 5–6. The half-life of allicin ranged from 235 to
after 0, 0.5, 1.5, 2, 3, 5, 7, 9, 120, 360, 480 and 720 h. Allicin residual
400 h (from 10 to 17 days) at optimal pH 5–6 (Table 1). The rate
ratio, degradation fitted curve and half-life calculations were made
of degradation of allicin varied slightly with concentration. The
as above.
data in Table 1 show that the half-lives of allicin at a concentra-
tion of 9.03 mg L−1 were longer than those at 6.02 mg L−1 , which
in turn were longer than those at 3.01 mg L−1 . This indicated that
the half-life of allicin at higher concentration was longer than that
RESULTS at lower concentration.
Quantity of allicin in aqueous extract
Following the UPLC method,2 the retention time of allicin was
around 0.95 min (Fig. 1). The linear equation y = 874.47x − 408.95 Allicin stability to storage temperature
(R2 = 0.9991) was constructed and the concentration of allicin in As observed in previous studies, allicin was sensitive to stor-
samples was calculated from this equation. The concentration age temperature. At room temperature (25 ∘ C), allicin was stable
of allicin in the original aqueous extract was determined to be with no obvious degradation for 5 days (Table 1 and Fig. 3), and
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30.11 mg L−1 . The pH of the unbuffered aqueous extract was 5.6. its half-life was about 400 h (17 days). However, allicin degraded

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 www.soci.org H Wang et al.

(a) 20 days at 4 ∘ C and 40 days at −20 ∘ C with no obvious degra-

120 T=-20°C T=4°C T=25°C T=40°C dation. Allicin degraded completely after 120 h (5 days) when
T=55°C T=70°C T=80°C the storage temperature was higher than 40 ∘ C. The longest
Residul ratio of Allicin in solution (%)

100 half-life of about 8100 h (337 days) was observed at −20 ∘ C in the
high-concentration solution (9.03 mg L−1 ). The shortest half-life of
only 0.16 h occurred at 80 ∘ C in the lowest concentration solution
80 (3.01 mg L−1 ).The half-life of allicin at room temperature (25 ∘ C)
was around 15 days.
60
Allicin stability to light
40
Allicin stability in the original garlic extract remained largely
unchanged during storage at 25 ∘ C in either darkness or light
(903 μmol m−2 s−1 ). The half-life under light was slightly shorter
20 than that in dark storage (Table 1 and Fig. 4).

0
0 0.5 1 1.5 2 3 5 7 9 120 360 480 720 DISCUSSION
Time (h) Allicin, as a principal compound from garlic, has been considered
(b) to be a very short-lived substance.27 According to the results
120 T=-20°C T=4°C T=25°C T=40°C of previous studies, the stability of allicin in aqueous extracts is
affected mostly by ambient temperature, pH, solvent and possibly
Residul ratio of Allicin in solution (%)

T=55°C T=70°C T=80°C

100 light. In the present study, allicin stability in aqueous extracts was
investigated in more detail at different temperatures, pH values,
concentrations and light conditions.
80 This study is the first to evaluate the effects of pH on allicin
stability in aqueous extracts. Allicin was very sensitive to pH. Its
60 high sensitivity to low pH confirmed an earlier suggestion that it
is difficult for allicin to remain intact in the stomach where the pH
is around 2.31 The stability of allicin in the original aqueous extract
40
was similar to that in solutions with pH 5–6. The half-life of allicin
ranged from 10 to 17 days at optimal pH 5–6. It was very unstable
20 in solutions of pH above 11 or below 1.5.
The thermostability measurements obtained over a wide tem-
0 perature range from −20 to 80 ∘ C in this study suggest that a
0 0.5 1 1.5 2 3 5 7 9 120 360 480 720 temperature as low as possible is desirable to preserve allicin in
Time (h) aqueous extracts. The results confirmed previous reports that
(c) allicin was unstable at high temperature.27,32 The half-life of allicin
120 in water was estimated to be 11–16 days at room temperature,
T=-20°C T=4°C T=25°C T=40°C
which was somewhat longer than the <11.5 days reported by Fuji-
Residul ratio of Allicin in solution (%)

T=55°C T=70°C T=80°C

sawa et al.33 but shorter than the 30–40 days reported by Lawson
100
and Gardner.26 Arzanlou and Bohlooli6 reported that allicin-free
garlic extract was completely degraded to undetectable levels
80 of allicin at room temperature up to 90 days. The inconsistency
in half-lives reported by different authors may arise from differ-
ences in the concentration of allicin in the extracts or in the room
60
temperature used in the studies.
This study also indicated that the concentration of allicin in
40 solution affects its stability, so that the higher its concentration, the
more stable allicin will be. Fujisawa et al.33 suggested that a higher
concentration of aqueous extract of garlic would make allicin more
20
unstable. However, in the present study the higher concentration
had a longer half-life in both buffer solution and the original
0 aqueous extract. Previous studies have shown a wide genetic
0 0.5 1 1.5 2 3 5 7 9 120 360 480 720
variation in the allicin content of garlic, indicating that the allicin
Time (h)
contents of different varieties of garlic will be very different.7,34 – 37
Figure 3. Stability of allicin in aqueous extract as a function of temperature Thus garlic varieties with high allicin content would be suggested
at (a) high (9.03 mg L−1 ), (b) medium (6.02 mg L−1 ) and (c) low (3.01 mg L−1 ) to prepare allicin aqueous extracts.
concentrations. Data are mean of three replicates. Error bars denote ± SE. Allicin is typically stored in low light and is thought by some to
be very sensitive to light. However, we found that allicin in aqueous
quickly when the temperature was above 40 ∘ C, with much more extract was not very sensitive to light, although light exposure did
1842

rapid degradation above 70 ∘ C. Allicin was stable for at least reduce its stability to a small extent. The results reported here were

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Figure 4. Stability of allicin in aqueous extract under light and dark conditions. Data are mean of three replicates. Error bars denote ± SE.

obtained with light of moderate intensity (903 μmol m−2 s−1 ). Fur- 3 Cavallito CJ, Buck JS and Suter CM, Allicin, the antibacterial principle
ther experiments with stronger light intensity may show greater of Allium sativum. II. Determination of the chemical structure. J Am
Chem Soc 66:1952–1954 (1944).
effects. 4 Kim SM, Wu CM, Kobayashi A, Kubota K and Okumura J, Volatile
compounds in stir-fried garlic. J Agric Food Chem 43:2951–2955
(1995).
CONCLUSIONS 5 Rybak ME, Calvey EM and Harnly JM, Quantitative determination of
allicin in garlic: supercritical fluid extraction and standard addition
The results obtained in this study indicated that allicin in aqueous of alliin. J Agric Food Chem 52:682–687 (2004).
extract was sensitive to pH. It was most stable at pH 5–6 but very 6 Arzanlou M and Bohlooli S, Introducing of green garlic plant as a new
unstable at pH higher than 11 or lower than 1.5. Allicin in aqueous source of allicin. Food Chem 120:179–183 (2010).
extract was strongly affected by storage temperature but not to by 7 Baghalian K, Ziai SA, Naghavi MR, Badi HN and Khalichi A, Evaluation
light. It degraded quickly when the temperature was higher than of allicin content and botanical traits in Iranian garlic (Allium sativum
L.) ecotypes. Sci Hort 103:155–166 (2005).
40 ∘ C and especially higher than 70 ∘ C. A higher concentration of
8 Arzanlou M, Bohlooli S, Jannati E and Mirzanejad-Asl H, Allicin from
allicin in solution was more stable. Hence a solution pH of 5–6, garlic neutralizes the hemolytic activity of intra- and extra-cellular
a low storage temperature of −20 ∘ C and a dark environment are pneumolysin O in vitro. Toxicon 57:540–545 (2011).
suggested to retain allicin longer in aqueous extract of garlic. 9 Ilic DP, Nikolic VD, Nikolic LB, Stankovic MZ and Stanojevic LP, Ther-
mal degradation, antioxidant and antimicrobial activity of the syn-
thesized allicin and allicin incorporated in gel. Hemijska Industrija
64:85–91 (2010).
ACKNOWLEDGEMENTS 10 Khodavandi A, Alizadeh F, Aala F, Sekawi Z and Chong PP, In vitro inves-
This research was supported by the National Science Founda- tigation of antifungal activity of allicin alone and in combination
tion for Young Scientists of China (31000910), the China National with azoles against Candida species. Mycopathologia 169:287–295
R&D Special Fund for Public Welfare Industry (200903018-03), the (2010).
11 Nya EJ, Dawood Z and Austin B, The garlic component, allicin, pre-
National Key Technology R&D Program from the Ministry of Sci- vents disease caused by Aeromonas hydrophila in rainbow trout,
ence and Technology of China (2013BAD01B04-8) and the Key Lab- Oncorhynchus mykiss (Walbaum). J Fish Dis 33:293–300 (2010).
oratory of Horticultural Crops Genetic Improvement, Ministry of 12 Guo N, Wu XP, Yu L, Liu JB, Meng RZ, Jin J, et al., In vitro and in vivo
Agriculture. The authors also very much appreciate the assistance interactions between fluconazole and allicin against clinical isolates
from Prof. Philipp W Simon and all members of the USDA-ARS Veg- of fluconazole-resistant Candida albicans determined by alternative
methods. FEMS Immunol Med Microbiol 58:193–201 (2010).
etable Crops Research Unit and Department of Horticulture, Uni-
13 Aala F, Yusuf UK, Khodavandi A and Jamal F, In vitro antifungal activity
versity of Wisconsin, USA. of allicin alone and in combination with two medications against six
dermatophytic fungi. Afr J Microbiol Res 4:380–385 (2010).
14 Luo DQ, Guo JH, Wang FJ, Jin ZX, Cheng XL, Zhu JC, et al., Anti-fungal
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