MODULE 2: PHARMACOGNOSY

Pharmacognosy:  described the study of Medicinal

 an applied science that deals with the plants and their properties
biological, biochemical and economic  Fluckiger proposed the most
features of drugs or biological origin and comprehensive definition of
their constituents pharmacognosy
 a respected discipline that has no  “Simultaneous application of
counterpart in other professions various scientific disciplines with
 knowledge of drugs & pharmaceuticals the objective of acquiring drugs
 a science that deals with plants and from every point of view”
animal constituent  Biologic - botanical source,
 this knowledge is based on the history, distribution, collection,
incantations of voodoo tribes that is etc.
passed on from one generation to  Biochemical - how the drugs
another are formed
 Economic - how they are
BRIEF HISTORY produced

 PELLETIER & CAVENTOU

BABYLONIANS
 Quinine
 Mesopotamia
 made clay models of man, they are fully  FRIEDRICH SETURNER
aware of the drugs that can affect the
 compounded morphine
human body
 Law of Hammurabi (772 BC): how
plants are being used TERMS
 medicinal plants of 250 plants
 mages and physicians CRUDE DRUGS
 wheat and barley  “Plant Exudates”
 natural (vegetable/animal) substances
EGYPTIANS 1550 BC that has undergone only the processes
 very apt in the practice of embalming of collection & drying
 vast knowledge on the medicinal uses of
plants and animals as written in the NATURAL SUBSTANCES
Papyrus ebers (George Ebers)  found in nature
 human anatomy and use of plants  whole plant and their parts; animals and
 Priest doctors their excised organs
 “no molecular modification” had been
AYURVEDA 2500-600 BC made
 from India
 “Science of Life” DERIVATIVES or EXTRACTIVES
 mother of all healing arts!  chief principles or constituents of crude
 Charaka - text on internal medicine drugs that are separated and used in a
 Sushrvta - 184 chapters, 1120 specific manner
illnesses; portion by portion of human  Solvent / Menstruum - liquid or liquid
body ; aka Book of Symptoms mixture used to extract active principles
 Marc - the undissolved portion of the
GREEKS drug that remain after the extraction
 Dioscorides wrote De Materia Medica process is completed
or the Medicinal Material (78 AD)
 where 600 plants are listed to INDIGENOUS PLANTS
have medicinal value, used by  plants growing in their native countries
physicians to treat disease
 aloe, belladonna, colchicum, NATURALIZED PLANTS
ergot and opium  plants that grow in foreign land other
 Claudius Galen described methods of than their native homes
preparing formulae containing plants *Rinorea niccolifera – metal eating plant
and animal drugs (131-200 AD)
 father of pharmaceutical METHODS OF EXTRACTION
compounding
 “galenicals
Infusion – hot water (ex. Tea); 3-5 minutes only
Maceration – soaked in solvent for long periods
GERMANS
of time
 C.A. Seydler (1815) coined the term Percolation – filtering of fluids through porous
pharmacognosy (pharmakon = drugs,
materials
gnosis = knowledge) in Analecta o
Digestion – <35-40 C; not boiling (low heat)
Pharmacognistica Decoction – boiling water
 J.A. Schmidt first used the term Liquid-Liquid Extraction – portioning
pharmacognosy in Lehbuch de Materia Distillation – purifying liquid by heating and
Medica cooling

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 PREPARATION OF CRUDE DRUGS CHEMICAL EVALUATION
 assay of active constituents using
chemicals
COLLECTION  Titration is the best method for
 ensuring the true natural source of the determining official potency
drug
 improper collection results to partial or PHYSICAL EVALUATION
complete substitution; collection time;  determination of various physical
highest content characteristic or parameters with the
 Flower - best to harvest at dawn use if physico-chemical techniques
 Bark - spring and summer  ex. specific rotation of camphor,
 Root crops - when upper ground synthetic camphor is racemic; natural
portion is about to wither camphor is dextrorotatory

HARVESTING
 specific or proper season PREPARATION OF CRUDE DRUGS
 manual labor vs. mechanical devices

DRYING MORPHOLOGY
 remove moisture to prevent bacterial,  forms; plant part used
fungal growth and enzymatic  convenient but no chemical correlation
degradation
 fixes constituents, facilitates grinding TAXONOMIC
and milling  Phylogeny - natural relationship that
 converts plants to convenient form occurs among plants and animals
(phyllum) ex. Solanaceae family contain
 Curing - special drying process that
solanaceous alkaloids
enhances the properties of the plant’s
active ingredients  Evolutionary development but no
orrelation on chemical and biologic
GARBLING actuality
 final step in the preparation of crude  Class – Subclass – Order –
drugs Family – Subfamily – Genus -
Species
 removal of extraneous matter
PHARMACOLOGIC
PACKAGING, STORAGE & PRESERVATION
 based on the therapeutic effect on the
 protection and marketability
body (ex. Cathartic - cascara sagrada,
 to avoid insect attacks:
senna)
1. simplest method: expose drug
to 65°C
CHEMICAL
2. fumigation with methyl bromide
 based on the active constituents that are
3. add a drop of chloroform or
present
carbon tetrachloride
 preferred method of classification
 Phytochemical studies but ambiquous
EVALUATION OF CRUDE DRUGS at times

• Determine its quality (inherent/descriptive in CONSTITUENTS & ACTIVE CONSTITUENTS

nature) and purity
• Qualitative and Quantitative Assays
• Quality - intrinsic property of drug; amount Constituent - mixture of substance
of medicinal principle or active constituent Active Constituent
present in a drug sample (ex. Alcohol USP)  “secondary metabolites”
• Quantity – amount  the process of producing these
secondary metabolites used as
ORGANOLEPTIC EVALUATION drug is also known as drug
 uses the organs of sense biosynthesis or biogenesis
 evaluate macroscopic appearance of  isolated constituent that is either
drug pharmacologically active or
pharmaceutically active
MICROSCOPIC EVALUATION
 identity and purity of the drug substance BIOGENESIS is influenced by:
1. Ontogeny or Stage of Development
 adulterant can also be detected
microscopically  Not absolute: concentration of
 cellular level (ex. Carbohydrates) drug increases with the age of
the plant
PHARMACOLOGIC EVALUATION  identity of the constituent also
 Preclinical or Bioassay - assay that varies according to the stage of
uses living animals or excised organs to development
evaluate the effects of drugs (ex.  ex. Cannabis sativa
Pigeons - Digoxin ; Cat - Atropine ; (cannabidiol to cannabinol
Chickens - Oxytovin) once the plant matures)

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 2. Heredity HEXOSE
 ex. Japanese peppermint –  most important monosaccharide
produces 40% menthol; 50x
more menthol than peppermint 1. Glucose
(Mentha peperita/Peppermint)  Aldohexose
 aldehyde group is present in C1
3. Environment  reducing sugar as determined by
 Chichirica or Periwinkle Benedict’s Test
 source of Vinca Alkaloids  occurs as linear and cyclic
 wild and domesticated  Linear configuration: Fischer
projection
CARBOHYDRATES  L-glucose : less active
 D-glucose : more active
 B-D-glucose : most abundant form
 polyhydric aldehyde or ketone alcohols
 Cyclic configuration: Haworth
that contain C, H & O
projection looks like a pyran:
 the H & O has the same ratio as that of glucopyranose
water, thus they are named as
 D-glucose or dextrose
Carbo + Hydrates
 blood sugar or grape sugar(high content
 first products of photosynthesis
sugar) or physiologic sugar
 Xylem - H2O (liquid)
 U: Parenteral - rigorously purified D5W,
 Pholem – nutrient (food) D5NSS, D5LR (nutrient)
 Function: energy source and storage;  U: Pharmaceutic Necessity - less
structure of plants and animals rigorous purification
 Liquid glucose - syrupy liquid,
MONOSACCHARIDE
almost colorless, tastes sweet,
 simple sugars sweetening agent
 (CHO) sugars that cannot be hydrolyzed  Dextrose excipient –
further crystalline sweetening agent;
 characterized by the number of carbon Oral Glucose Tolerance Test
atom in the molecule (75g)
 (+) Benedict’s and Barfoed’s Test (brick  Other glucose derivative
red ppt)  Ca gluconate
 Ca gluceptate
 Ca levulinate
# of C Name Examples  Fe gluconate
2 Diose Hydroxyacetyldehyde
2. Fructose
Hihydroxyacetone,  alpha-ketohexose
3 Triose
Glyceraldehyde  ketone group is present in C2
 reducing sugar
4 Tetraose Erythrose
 obtained from inversion of aqueous
Arabinose, Xylose, sucrose solution
5 Pentose  high fructose sweeteners =
Ribose
isomerization of glucose isomer from
Glucose, Fructose, Streptomyces sp.
6 Hexose
Galactose  fruit sugar, sweet fruits and honey
7 Heptose Sedoheptose  also known as levulose, the sweetest
monosaccharide
8 Octulose D-mannuctulose  Uses:
 food for diabetic patient
 ingredient in infant feeding
PENTOSE formula
 ingredient in fructose injection,
Aldehyde Ketone nutrient
Xylose Xylulose  bitter aftertaste
Ribose Ribulose  Mango : highest fructose
 (+) Seliwanoff’s Test: pink/red (Ketone)

1. Xylose 3. Galactose
 wood sugar  “brain sugar”
 polymer: Xylan  Aldohexose
 obtained from boiling corn cobs, straw  C4 epimer of Glucose (C2 naman is
and similar material with dilute acids to Mannose)
hydrolyze the sylan polymer  milk: lactose :: neuronal fibers:
 diagnostic aid in intestinal malabsorption galactoside
 absorbed but not metabolize  Gaucher’s Disease
 Inability to metabolize galactose
 (+) Mucic acid and Phenylhydrazine:
crystal formation

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 PRODUCT OF OXIDATIVE METABOLISM
DISACCHARIDE
 composed of 2 monosaccharide unit 1. Cherry Juice or Succus
formed via dehydration synthesis  ripe fruit of Prunus cerasus (Rosaceae)
 glycosidic bond (C-O-C)  contains pectin, the main cause of
*incomp* especially when added to
1. Sucrose (Glucose + Fructose) prepared cont. alc.
 “table sugar”  remedy: add 0.1% benzoic acid & leave
 obtained from: for 1 week
 Sugar cane Saccharum  constituent: malic acid (>1%)
officinarum (Poaceae)  use: preparation of cherry syrup which is
 Sugar beet Beta vulgaris used to mask the taste of salty drugs
(Chenopodiaceae)
 Cossettes – “Cut Limb 2. Plant Acid
Silvers”  uses: acidulant in effervescent
 Sugar maple Acer saccharum formulation; component in buffer system
(Aceraceae) a. Citric Acid - isolated by Scheele
 Non-reducing sugar from Lemon juice in 1784
 a 1,2 bond b. Lactic Acid - acidulant in infant
 Uses: feeding formula
 Demulcent c. Tartaric Acid - by-product of wine
 sweetening agent industry
d. Ferrous fumarate – hematinic
 coating agent
 Denige’s Test – differentiation test for
 preservative
citric and tartaric
 production of syrup
 Tartaric: emerald green
 retards oxidation
 Lactic: crimson red
 85% preservative concentration
 Sucrose + Lime =ppt Albumin
 Molasses - residual dark colored syrup Citric: TCA (tricarboxylic acid
after complete crystallization of sucrose > Tartaric: DCA (dicarboxylic acid)
(food + ethanol industry); only TAWI2
disaccharide in FREE STATE TA – Tartaric
WI – wine
2. Maltose (Glucose + Glucose) 2
 “malt sugar” – DCA
 a 1, 4 bond
 produced during the germination of
barley 3. Alcohol or Ethanol
 major degradation product of starch  95% Ethanol by volume at 15.56°C
 reducing sugar
 product of fermentation
 undergo the process of distillation to
3. Lactose (Glucose + Galactose)
concentrate the alcohol to 40-55%
 “milk sugar”
 Brandy – wine
 B-1, 4 bond
 Whiskey - malted grain
 obtained from Cow’s milk
 Rum – molasses
 reducing sugar
 in low concentration - CNS stimulant
 in high concentration - CNS depresant
 Glu + Glu + Glu = Maltotriose
 diluted alcohol: 48.4-49.5% at 15.56°C
 Oligosaccharide – 3 to 10 C

4. Lactulose PRODUCT OF REDUCTIVE METABOLISM

 alkaline rearrangement of lactose
 B-1, 4 bond 1. Mannitol
 converted to lactic acid and acetic acid  from manna, Franxinus ornus
which causes irritation of the intestines (Oleaceae)
in subsequent catharsis  osmotic diuretic & osmotic laxative
 decrease serum ammonia (effective on the descending loop of
concentration in partial systemic Henle - renals), GFR evaluation
encephalopathy
 most abused drug in the hospital 2. Sorbitol
 from the berries of mountain ash,
Sorbus auouparia (Rosaceae)
 aka D-glucitol
 tastes half as sweet as sucrose
 not absorbed on oral ingestion, that is
why it is used in the manufacture of
toothpaste and chewing gums
 sweetener
 increase spreadability

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 POLYSACCHARIDES 2. Inulin
 Fructosan
A. Homoglycans  Polyfructan of fructofuranose
 polysaccharides that yield one type of  Chirory root – Chicorium intybur
monosaccharide unit upon hydrolysis! (Asteraceae)
 use: ingredient in culture media; used in
1. Starch the evaluation of renal function;
 temporary storage form of improves digestion
photosynthetic products!
 from: 3. Dextran
 corn: Zea mays (Poaceae)  glucosan
 wheat: Triticum aestivum  Leuconostoc mesenteroides release the
(Poaceae) enzyme dextran sucrase which is
 potato: Solanum tuberosum responsible for converting sucrose to
(Solanaceae) dextran
 rice: Oryza sative (Poaceae)  plasma expander because it has the
 arrowroot: Maranta arundinacea same osmolarity and viscosity as
(Marantanaceae) plasma
 Dextrin – brown in bread

4. Cellulose
STARCH CONSTITUENTS
 Most abundant organic matter
Bases of  Structural polysaccharides in plants
Amylose Amylopectin from the hair of Gossipium hirsitum
Difference
(cotton)
Branched
Linear
1000 or more a. Purified / Absorbent cotton!
250-300
glucose unit linked  from the hair of the seeds of
D-glucopyranose
Structure by a-1,4- & a-1,6- Gossypium hirsutum
units linked by
glycosidic bonds (Malvaceae)
a-1,4-glucosidic
bonds
every 25-30  uses: mechanical protection
glucose unit against bacteria; surgical
dressing
Solubility  absorb mucus, pus and blood
Soluble Insoluble
in water
b. Soluble Guncotton/Pyroxylin
Iodine Test dark/deep blue blue-violet/purple
 formed by the action of nitric
Ratio 25% 75% acid and H2SO4 on cotton
 Other ingredient: Castor oil
(flexibility) & Camphor
 Enzymes that break down starches (waterproof)
 Alpha-amylase - present in
 use: topical protectant
pancreatic juice and saliva
(humans) c. Other cellulose derivatives
 Beta-amylase – hydrolyzes  Cellulose Acetate Phthalate
starch to nearly pure maltose (CAP) - coating agent
(fruits)
 Methylcellulose &
Ethylcellulose – artificial tears
Metabolizes / breakdown of carbohydrates
starts in the mouth 5. Glycogen
 Storage polysaccharide in animals
 Uses of starch: tablet filler, binder,  More branched than starch (ever 10)
disintegrant. Antidote for iodine  Red color with Iodine
poisoning  Found in liver and skeletal muscle (8-12
 Starch Preparations: hrs)
 Pregelatinized Starch – starch
that is chemically or 6. Chitin
mechanically processed to  Structural polysaccharide in animals
rupture all or part of the  Exoskeleton: mullusks and arthropods
granules; tablet binder  Homoglycan of N-acetylglucosamine
 Chitosan – deactivation of chitin, H2O
 Sodium Starch Glycolate - purification
disintegrating agent  Glucosamide – acid deacetylation and
hydrolysis of chitin
 Hetastarch - plasma expander
(6%) – low blood volume; B. Heteroglycans
Hydroxyethylstarch  polysaccharides that yield more
than one type of
 Glutens – tacky proteins; impedes flow monosaccharide unit upon
of starch; meat substitute hydrolysis

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 GUMS AND MUCILAGES
 Indian or Ghatti Gum
• natural plant hydrocolloids that may be  Anogeisus latifolia
classified as anionic or non-ionic  alternative for Acacia
polysaccharide
• produced by plants as a protective after 2. Seed Gums
injury
• upon hydrolysis they yield arabinose,  Plantago / Psyllium / Plantain seed
galactose, glucose, mannose, xylose  seed coat of Plantago psyllium
and other uronic acid derivative (Spanish psyllium) and Plantago
• Pb Acetate and Alcohol ovata (blonde or indian psyllium)
 bulk laxative, should be taken
1. Plant Exudate with water
 Metamucil/C-lium
 Acacia or Gum Arabic
 Acacia senegal (Fabaceae)  Cyclonium or Quince Seed
 constituent: Arabin (K, Ca, Mg,  ripe seed of Cydonia vulgaris
Arabic acid)  Thixotropic agent of lotion
 12% H2O content
 incompatible in preparation  Guar gum or Guaran
containing more than 60%  endosperm of Cyamopsis
alcohol tetragondobus
 only 5-6% swells in water
 Mucilage; emulsifier;  Locust Bean Gum / Carob pulp or St.
suspending agent(33-35%) John Bread
 GuMuP – soluble slime gel  endosperm of Ceratonia siliqua
 flour of the carob resembles
LINEAR BRANCHED chocolate
 used by John the Baptist
Solubility Less More
Stability Less More 3. Microbial Gum
 Xanthan Gum
Use
Viscosity
Gelating agent  action of Xanthomenas
enhancer campestris on carbohydrate
 has a pseudoplastic activity
(shear thinning)
GUMS MUCILAGE  enable toothpaste and ointment
to spread readily
Pathologic Physiologic
Production
(injury) (natural) 4. Plant Extract
Solubility  Pectin
in H2O
Readily soluble Slimy mass  purified carbohydrate product
obtained from the dilute acid
*Pectin – Gel (Sol in water) extract of the inner portion of the
rind of citrus fruit and apple
 Tragacanth pomace
 Astragalus gummifer  antidiarrheal agent
(Fabaceae)  intracellular cementing material
 constituent:  partially methoxylated
 Bassorin - gelling galacturonic acid (reason of
component (swells 2/3) swelling)
 Tragacantharin -  extract of the inner rind of citrus
non-gelling component fruits and apple pomace
(dissolves 1/3)  Koapectate – Kaolin + pectin =
 Types: anti-diarrheal
 Vermiform – worm
5. Marin Gums
 Tragacanth sorts –
tears Gum Source Constituents
 Ribbon/Flakes – non- Algae(green)
transverse; preferred Agar/ Gelidium
grade Agaros
Japanese cartilagineum
 35-36% swells in water; best Isinglas Gracilaria
Agaropectin
mucilage; most resistant to acid confervoides
hydrolysis
 5-6% suspending agent Algin
Brown seaweeds Mannuronic
Macrocystis pyrifera acid
 Karaya or Sterculia Gum Kappa –
 Sterculia urens (Fabaceae) Red algae gelling
 constituent: D-galacturenic acid Carageenan /
Chrondus crispus Iota – gelling
and Dglucoronic acid Irish Moss
Gigantina mamillosa Lambda – non
 fetid odor gelling
 galactomannan – bulk laxative
Danish Agar Furcelaria fastigiata Kappa

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 GLYCOSIDE
Kaopectate + pectin = antidiarrheal prep 3. Aloe
 dried latex/juice from Aloe barbadensis
 compounds that yields one or more sugar or Aloe vera (Curacao Aloe)
upon hydrolysis  hybrids of Aloe ferox with Aloe
 Heteroglycans – “Sugar Ethers” Africana and Aloe spicata (Cape Aloe)
 composed of 2 moieties: sugar portion  constituent: barbaloin & aloe emodin
(glycone) and non-sugar (aglycone)  use: pharmaceutic component of
 (Sugar-O-R) compound benzoin tincture; moisturizer
 the sugar moiety of a glycoside can be  Aloe vera Gel - treatment of burns and
joined to the aglycone in various ways, the employed as emollient (2%)
most common, being via an O-atom
(Oglycoside) C-atom (C-glycoside) N-atom 4. Rhubarb
(Nglycoside) or S-atom (S-glycoside)  Glucorhein
 beta forms occurs in plant
 regulatory, protective, sanitary compounds  Rheum or Chinese Rhubarb
 Rheum officinale
Glycone vs Aglycone(genin)  Rheum palmtum
Vehicle Classification  medicinal
Inactive Active  Indian Rhubarb or Himalayan
Rhubarb
ANTHRAQUINONE GLYCOSIDE  Rheum emodin
 form the largest group of naturally  Rheum webbeianum
occurring quinine segment  constituent: rhein anthrones
 occurs in plants usually as hydroxylated,  ornamental
methylated or carboxylated derivative of
anthraquinone, anthrone, anthral or 6. Senna
dianthrone  dried leaflet of Cassia acutifolia
 occurs as O and/or C-glycoside or as (Alexandria – broken leaflet used in
their aglycone prep) or Cassia angustifolia (Tinnevely –
 Aglycones are anthracene derivative full leaflet)
colored substance which are the active  cultivated in wetlands resembling rice
components of laxatives and purgatives paddies
 increases peristaltic movement  constituent: sennoside A, B, C & D
 short term use causes constipation; (blue green)
while frequent or long term use causes
intestinal tumor as side effect 7. Chrysarobin
 drastic cathartic  from Goa powder Andria araroba
 orange (red-orange) color derivative  only anthraquinone that is not used as a
cathartic because it is very irritating
 Borntrager’s Test
used as a keratolytic
 hot benzene is used to extract this
substance

CARDIAC GLYCOSIDE
 unsaturated steroidal aglycone test
 Libermann-Burchard (blue/gree;
yellow for saturated)
 Salkowski (red/violet)
 2-deoxy sugar glycine test
 Keller-Killiani Test (reddish
brown)

Cardenolides Bufadienolides
common rare (Bufo sp.)
1. Cascara sagrada - sacred bark
 Rhamnus purshianus C-23 a & B unsaturated C-24 doubly unsaturated
 constituents: 9-membered lactone ring 6-membered lactone
 O-glycoside: based on emodin ring
 C-glycoside: based on aloin
 Cascaroside A&B: optical
isomer of barbaloin
 Cascaroside C&D: optical
isomer of chrysaloin
 Lane’s Pill – casanthol, purified mixture
of anthranol glycoside

2. Frangula or Buckthorn Bark

 Rhamnus frangula
 present in Movicol: Karaya(laxative) +
Frangula(cathartic)

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  Cardenolide 2. Dioscorea or Yam
 Digitalis  Dioscorea spiculiflora – contains
 Digoxin – H2O soluble diosopenin which is a glucocorticoid
 Digitoxin – lipid soluble precursor
 Desllanatoside  Dioscorea floribunda - best source of
 Convallaria – Convallaria steroid (Mexican yam)
mahalis  Diosgenin – anti-inflammatory property
 Lily of the valley
 Convalatoxin 3. Ginseng
 Apocynum  Panax ginseng (Asian ginseng)
 Dogbane  Panax guingefolia (American ginseng)
 Cymarine – inotrope  Uses:
 Adonii  Aphrodisiac
 Pheasant’s Eye  Adaptogen (stress)
(emerald green)  Tonic (increase value of health)
 Adonitoxin  constituent: panaxoside, ginsenoside
 Black Hellebore (helleborous & chikusestsusaponin
niger)  Ginseng of Europe: Chamomile – dried
 Christmas rose petals of Matricaria chamomile
 Hellebrin (+) inotrope
 Strophantus CYANOPHORIC / CYANOGENIC GLYCOSIDE
 / K – strophantin  liberates HCN upon hydrolysis
 X G – strophantin –  biosynthetically derived from, L-amino
oaubain(toxic) acid (eg. Amygdalin from L-
phenylalannine)
 Bufadienolides
 B-glycosidic derivative of 2-
 Squill
hydroxynitrite (cyanohydrile)
 Red squill – poison
 fairly unstable & stabilized by
 White squill –
glycosylation
scillarenin; expectorant
 used as flavoring agent
SAPONIN GLYCOSIDE  10mg of HCN/kg of plant is the content
needed before a plant is considered
 possesses a soap-like behaviour in
cyanogenic
water and produces foam upon shaking
 lethal dose: 0.5-3.5mg/kg BW (single d)
 bitter, acrid taste
 sternutatory – induces sneezing
1. Amygdalin
 destroys RBC’s of cold blooded animals
 Amygdalase + Puranase are collectively
– fish poison
known as Emulsin
 froth, hemolysis, capillary
 Rosaceae
 upon hydrolysis, an aglycone is
 (+) Guignard’s Test: Brick-red coloration
produced which is sapogenin
 substances containing amygdalin:
 toxic aglycone: sapotoxin
 Bitter Almond Prunus
 steroidal in nature
amygdalus!
 Wild Cherry Prunus serotina –
 2 Types of Sapogenin:
flavored vehicle expectorant and
 Steroidal saponin - used in sedative
commercial production of sex
 Apricot Prunus ameniaca bitter
hormone
almond is a source of Laetrile
or Vit B17 - a controversial
 Triterpinoid saponin - treatment for sickle cell anemia
aglycone is triterpene. used as
fish poison causing paralysis of ISOTHIOCYANATE GLYCOSIDE
the gill. It exerts a powerful
 isothiocyanate aglycone
hemolytic action on RBCs and
 Aglycone may be aliphatic or aromatic
are highly toxic when in the
derivative
bloodstream
 Rapeseed (Brasica napus): Gluconapin
1. Glycyrrhiza / Licorice  Watercress (Naltrurtium officinale):
 dried roots of Glycyrrhiza glabra Gluconasturtiin
 increases the foaminess of beer
1. Black Mustard or Sinapis nigra
 constituent: glycyrrhizin which is 50%
 Brasica nigra
as sweet as sugar (masks bitter taste of
Quinine) * Yerba santa as well  contains sinigrin (myrosin) – allyl
isothiocyanate (mustard oil)
 Glycyrrhetic acid - anti-inflammatory
 Steroidal
2. White Mustard or Sinapis alba
 used in the treatment of Addison’s
 Brasica alba
disease
 sinalbin (myrosin) - acrinyl
 contraindicated for patients with
isothiocyanate (mustard oil)
HTN/Congestive heart failure – induces
 uses of mustard oil:
salt and water retention
 local irritant and emetic
 rubefacient, vesicant
 condiment

2017
8
 ALDEHYDE GLYCOSIDE
1. Vanilla
Sinigrin A↑↑y↑  cured fruit of Vanilla plantifolia
myrosinase
 Mexican/ Vera Cruz/Bourbon
Sinalbin Acriny↑  constituent: Vanillin-4-hydroxy, 3-
methoxybenzaldehyde
GLY ENZ V.O.
 uses: flavoring agent
 Ethylvanillin: substitute for natural
vanillin
FLAVONOL GLYCOSIDE PHENOL GLYCOSIDE
 flavonoids of bioflavonoids from citrus 1. Uva Ursi
fruits and soya  “bear berry”
 derivative of 1,3-diphenylpropane  dried leaf of Arctostaphylos uva ursi
 large group of natural product  constituent: arbutin (hydroxyquinone +
 yellow compound and contributes to sugar)
yellow color of the flower or fruit  use: astringent & diuretic
 potent anti-oxidant compound  cosmetic: whitening agent
 possesses anti-inflammatory,
antihepatotoxic, antitumor, antimicrobial 2. Poison Ivy & Poison Oak
and antiviral properties  Rhus radicans (Ivy)
 Rhus toxicodendron (Oak)
1. Rutin & Hesperidin  Uroshiol – delayed contact dermatitis
 Vitamin P or permeability factors (type 4, T-cell mediated)
 uses: treatment of capillary bleeding
secondary to capillary fragility LACTIONE GLYCOSIDE
 treatment of symptom of common cold 1. Coumarin
 from Tonka beans, Dipteryx odorata
2. Hesperitin, Diosmin, and Naringen  constituents: dicumarol,
(Echinacea) st
bihydroxycoumarin (1 oral
 treatment of symptoms of common cold anticoagulant)
 anticoagulant: Warfarin
3. Yellow Pigment  Test for unsaturated lactone: Kedde’s
 Rutin & Quercetin (blue-violet)
Milk Thistle 2. Cantharides
 Silubum marianum  from the dired insect of Cantharis
 Constituents: Silibinin, Silymarin vesicatoria
 Hepatoprotective  Blistering fly/Russian fly/Spanish fly
 constituent: cantharidin-irritant, vesicant
Gingko and
 Gingko biloba  rubefacient
 Constituents: Gingkolides, Bilolobides  causes priapism – sustained erection
 Memory enhancer
3. Psoralens
ALCOHOLIC GLYCOSIDE  Ammi majus
1. Salicin - Salix & Populus sp.  Bishop’s flower
 Salix purpurea (Willow bark) & Salix  should not expose to UV rays when usin
fragilis psoralens = skin cancer
 have anti-rheumatic and anti-  Methoxsalen (repigmentation in
inflammatory property vitiligo); trioxsalen
 aglycone: saligenin  photosensitizing fluorocoumarin
 closely related to salicylic acid a. Methoxsalen - repigmentation in
 Fehling’s (brick red) Vitiligo
 Nessler’s (gray) b. Trioxsalens
 Tollen’s (silver mirror)
 Schiff’s (recolorization)

*Vesicant – blistering agent

2017
9
 TANNINS
 heterogenous group of natural product TRUE TANNINS PSEUDOTANNINS
 widely distributed in the plant kingdom
 provides plants with protection against Polyhydroxyphenol
Phenolic compounds
microbial attack compounds which can
of plant origin that do
 polyphenolic compounds convert animal hide to
not convert animal
 they form insoluble & indigestible leathers by
hide into leather but do
compounds with protein (astringent) and precipitating proteins
give positive Gold
this is the basis of their extensive use in and give positive Gold
beater’s skin test
the leather industry and for the beatear’s skin test
treatment of diarrhoea, bleeding gums MW: 1000-5000 MW: < true tannins
and skin injury
 complex substances or polypeptide that
are difficult to separate because they do
1. Hamammelis Leaf
not crystallize (noncrystallizable
phenols)  Witch Hazel Leaf
 attacks alkaloids by neutralization  dried leaf of Hamammelis virgiana
 constituent: hammamelitanin
Characteristics of Tannins:  preparation: hamammelis water or
 Acidic Distilled Witch Hazel Extract
 Sharp puckering taste  use: hemorrhoids (enlargement of blood
 Causes precipitation of alkaloids vessels in anus); astringent (insect
bites)
 Can precipitate protein: used in tanning
industry – leather, ink, dye
2. Nutgall
 Astringents (GI or Skin)
 excrescence obtained from the young
 Treatment of burns
twig of Quercus infectoria (Fagaceae)
 when a hymenopterus insect, Cynips
Two Chemical Classes:
tinctoria, bores a hole to deposit its ova
causing enlargement
HYDROLYZA
NON-  constituent: Tannic acid
HYDROLYZA  uses: used in the tanning industry,
BLE
BLE astringent properties and the
Condensed manufacture of ink
Other name - tannins;  “best source of tannic acid”
Phlobatannins
Tannic acid
Results from  Use: astringent; component of universal
the antidote
condensation  Universal antidote = tannic acid
of catechin and (astringent, protein/alkaloid
Readily
leucocyanidin pptant) + MgO (redox) +
hydrolyzed to
Characterist activated charcoal
yield phenolic
ics When treated (adsorbption)
acids and
with hydrolytic  Composite acids that make up tannic
sugar
agents, they acid:
tend to
 Gallic acid
polymerize into
 Ellagic acid
▼
Phlobaphene 3. Chinese/Japanese Gall
Pyrogallol
(red-colored  Rhus chinensis
Hydrolytic
product phenolic acid
products,  Apis sp
and sugar
insoluble  Gallic acid
polymer)
Leather Bloom Tanner’s Red
FeCl3 Test Blue-black Gree-black
Br2 Test (-) (+)

2017
10
 LIPIDS
 may be classified as fixed oil, fat, waxes TESTS:
 Cocoa butter - only solid plant lipid 1. Saponification Value
 Cod Liver oil - only liquid animal lipid  number of KOH in mg required to
neutralize the free fatty acids and
saponify the esters found in 1g of the
FIXED OILS FATS WAXES
lipid
long chain  S = E + A (SEA)
fatty acid +
high
molecular 2. Acid Value
long chain long chain
weight  number of KOH in mg required to
fatty acids + fatty acids +
alcohol such neutralize the free fatty acids found in
glycerol glycerol
as cetyl 1g of the lipid
alcohol &
stearyl 3. Ester Value
alcohol!  number of KOH in mg required to
saponify the ester found in 1g of the lipid
From both
from from animals  not official identification test for
plants and
vegetable lipids
animals
Semisolid at 4. Iodine Value
liquid at room solid at room
room  number of iodine in grams absorbed by
temperature temperature
temperature 100g of the lipid
 measures the degree of unsaturation
Solid fixed oils Liquid fat –
Liquid was –
– theobroma, cod liver oil Extraction
jojoba
myristica (fish oil)
 Expression – for fixed oils only
 Cold-pressed oil: no heat; e.g
virgin oil
SATURATED FATTY ACID  Hot-pressed oil: heated;
common in the market
No. of Carbon atom Name  Rendering – fats
6 Caproic  Increase pressure with or
without steam (aq & fatty layer)
8 Caprylic  Fatty layer = clarify + ozone =
10 Capric rendered fat
 Solvent Extraction
12 Lauric  Hexane: best solvent extract for
14 Myristic fats

16 Palmitic Classification
 Ability to absorb oxygen
18 Stearic
 Oxygen saturates double bonds forming
20 Arachidic oxides that polymerize that form films
(hard film)
 Paint industry
UNSATURATED FATTY ACID
No. of Carbon atom Name According to ability to absorb O2:
Iodine Value Example
18 with 1 double bond Oleic
Range
18 with 2 db(C9, C12) Linoleic
Linseed Oil,
Drying oil > 120
18 with 3 db(C9, C12, Cod liver oil
Linolenic
C15)
Cottonseed oil,
Semi-drying oil 100-120
Sesame oil
Uses:
 Emollient Olive oil,
Non-drying oil <100
 Vehicles for IM injection (COCOPESE) Almond oil
 Corn, Cottonseed oil, Peanut oil,
Sesame oil
1. NOA – Noah’s Ark = great flood(wet) = nondrying
 Cathartic – castor oil
2. SeCoSe – Secosana = semi(not too cheap nor
 Soap production – lipid + strong base
expensive = semi drying
(NaOH-hard / KOH-soft)
3. LiCod – likod = dapat dry = drying
 Increase caloric value – TPN for
patients who cannot tolerate enteral/oral
administration Reaction of Lipids (based on Temperature)
 Extemporaneous TPN: prepared  Hydrogenation
in the laminar flow hood  Liquid oil to semi-solid fat
 Commercial TPN:  Passing of H with Pd/Ni in 160-
carbohydrates + amino acid + o
200 C
lipids (sourece:soya)  Shortening and cooking fat

2017
11
  Sulfation 7. Corn Oil
 Reaction with sulfuric acid  Zea mays
 Temperature at chilling  IM injection
 Sulfates adds to double bonds,  Germ oil cake
produce surfactants
8. Safflower Oil
FIXED OIL  Carthamus tinctoria
 long chain fatty acids + glycerol  Antilipemic agents
 from vegetable  High good cholesterol (HDL)
 liquid at room temperature
 concentrated at the seeds 9. Sunflower Oil
 Helianthus annus
Seed Oils  Antilipemic agents
1. Cottonseed Oil  High good cholesterol (HDL)
 Gossypium hirsutum  Heliotropism: tracking of the sun
 Cotton/bulak
 IM injection 10. Ethiodized Oil / Hemp Seed oil
 Halphen-Bevan Test: official  iodine addition of production of the ethyl
identification test ester of fatty acid of poppy seed
 Toxic principle: gossypol (0.6%) causes  Cannabis sativa
male sterility  diagnostic aid

2. Sesame Oil Hydrogenated Vegetable moil = (+) Serger’s Test

 Sesamum indicum
 Teel oil or Benne oil, Linga
 Baudouin Test: official Pericarp Oil
 Use: condiment 1. Olive Oil
 Constituent: sesamol (phenol) – confers  Olea europea
stability of sesame oils; preservative  Oil of Europe
(self-preserving principle)  Millon’s Test
 Sesamol + ligan = sesamolin  Grades:
(adjust for pyrethrin – for  First Grade Virgin Olive Oil –
insecticide, Licealiz) extracted with less pressure
 Second Grade Virgin Olive Oil
3. Coconut Oil - pulp in the above-mentioned
 Cocus nucifera grade is extracted with more
 IM injection pressure
 Serger’s Test: hydrogenated v.o.  Technical Oil - extracted with
 Constituents: Lauric, Myristic, hot water
triglycerides  Sulfur Grade - extracted with
Carbon Disulfide; inferior quality
4. Castor Oil  Tournant Oil - fallen and
 Ricinus communis decomposing fruit
 Tangan-tangan
 Constituents: FATS
 Tricinolein – good  long chain fatty acids + glycerol
 Ricinoleic acid – good, irritant,  from animals
cathartic, restores vaginal  solid at room temperature
acidity
 Ricin – toxic 1. Theobroma Oil
 Abrin – Jequirty  Theobroma cacao
bean/crab’s eye/rosary  food for the gods
beads  uses: cocoa syrup for beverage;
cocoa butter is used as suppository
5. Peanut Oil base because it melts at 30-35°C
 Arachis hypogeae  NIBS: brocken cacao kernels
 arachis oil  Prepared cacao/Breakfast cacao:
 IM injection, edible powder
 Peanut butter: 50% grounded peanut, o Aztecs and Americans were the
margarine first to use cacao for celebratory
 Nagaraya: 1batch recalled from the purposes
market due to aflatoxin content(fungi)
wich is only seen in nuts due to 2. Lanolin
improper handling and drying  purified fat-like substance from the wool
of sheep Ovis aries (bovidae)
6. Soybean Oil  contains 25% Water; hydrous woolfat
 Glycine soya  Anhydrous lanolin: Woolfat (contains
 lecithin and stigmasterol only 0.25% water, best water
 Lecithin – regulator of cholesterol absorbable base)
 use: water absorbable ointment base;
emollient

2017
12
 3. Cod Liver Oil
 from Gadus morrhua
 sclerosing agent to obliterate varicose
veins
 best source of Vitamin A & D (Scott’s
Emulsion) [Vit. A – most toxic vitamin]
4. Undecylenic Acid
 pyrolysis of ricinoleic acid from castor oil
 has antifungal property

5. Azaleic Acid
 ozonolysis of castor oil (R. commuris)
 anti-acne; component of lipstick

WAXES
 long chain fatty acid + high molecular
weight alcohol such as cetyl alcohol &
stearyl alcohol

1. Spermaceti
 head of sperm whale Physeter
macrocephalus
 synthetic spermaceti: cetyl ester wax
 first white candle from spermaceti –
“Sperma”

2. Jojoba Oil
 seed of Simmondsia chinensis
(Buxaceae)
 hydrogenated form resembles
spermaceti
 eicosenoic acids: eicosenol and
docosenol
 Jojoba and beeswax ae used in
shampoo, conditioner, etc.

Si Jojoba chinensis si Simon

3. Beeswax or Yellow Wax

 honeycomb of bees Apis mellifera
 stiffening agent in plaster and cerate
 White wax - bleached yellow wax
 Yellow wax - original unbleached form
o Myricyl palmatate – chief wax
principle

4. Carnauba Wax
 leaved of Copernicia punifera
 more economical, environmental and
ethical
 Myricyl cerotate: chief wax component

2017
13
 VOLATILE OILS
3. Expression - best method used for citrus
 ETHEREAL OILS, ESSENTIAL OILS, volatile oil whose aroma is injuriously affected by
ESSENCES heat; Rutaceae (resigenous and lysigenous
 Most viable is the colorless than dark-
colored oils; placed/stored in transparent  Ecuelle A Piquer – Citrus oil glands are
containers ( as alternative to amber bottles) punctured/pierced by rolling a fruit rind
for sampling to see which is most viable in a trough lined with sharp tiny
 Colorless and photosensitive projections enough to puncture the rind
 Undergoes auto-oxidation and resinification and not the fruit eg. Lemon oil, orange
 Light resistant tight containers oil.
 present in
 glandular hars - Labiatae (Lamiaceae)  Enfleurage - suitable in obtaining small
 modified parenchyma cells – amount of volatile oil in plant parts like
Piperaceae flower petal. Sample impregnated on a
layer of bland fat until fat is saturated
 Oil Tubes – Vittae or Apiaceae
with fragrance.
(Umbiliferae)
 lysigenous & schizogenous passage -
Components of Volatile Oil
Pinaceae or Rutaceae

Physical Characteristics: STEREOTERPENE ELEOPTENES

 possesses characteristic odor Solid oxidized Liquid hydrocarbon
 high refractive index (ability to bend light) hydrocarbon portion portion
 Refractometry –official ID test Methylsalicylate,
 optically active (ability to rotate polarized Menthol, Anethol,
Eucalyptol, Eugenol
light) Thymol (MATS)
(MEE)
 immiscible in water but they can be
sufficiently soluble to impart their odor in
4. Extraction - use of the Soxhlet apparatus
water (Aromatic Water)
and volatile solvent system eg. benzene, ether.
 can be distilled from their natural sources
 advantages: fast way, quality is
 no permanent grease on spot test
preserved (controlled temperature at
 they do not become rancid, they resinify 50°C)
 disadvantage: expensive
vs Fixed Oils
 can be distilled from natural sources 5. Destructive Distillation - eg. tar. means to
 V.O = distillation – oxidized to Resin
obtain oils with empyreumatic or “smoke-like”
 F.O. = saponification – products cannot
odor. heating without access of air
be used
 No permanent grease on spot test Medicinal & Commercial Use
 They do not become rancid. They rsinify
instead 1. Fabrication of Perfume
 Top Note - most volatile product, they
Method of Obtaining Volatile Oil leave the skin immediately.
1. Distillation - use of the Clavenger Apparatus o Lemon – most commercially
used
 Water Distillation - eg Turpentine. o Lavander – aromatherapy
Applied to dried plant not injured by o Anise oils (LAL)
boiling  Middle Note - intermediate tenacity &
volatility. (herbs and spicies)
 Water & Steam Distillation - eg Clove o Thyme
& cinnamon. water applied to dried & o Neroli
fresh material that may be injured by o Rose oils (RNT)
heat. Steam is passed through acerated  Base Note - low votality & high tenacity.
material (indirect) Aka fixative, staying power

 Direct Steam Distillation - eg 2. Musk - dried secretion from the preputial

Peppermint & Spearmint. applied to follicle of the male musk deer of asia (Maschu
fresh material (own moisture) no spp.); “phenomes” (used by some animals in
aceration needed; steam forced through mating
the fresh herb, carries oil droplet
through vapor pipe 3. Civet - a glandular secretion of appearing in
an outwardly discharging pocket of Civet cats
 Destructive Distillation - e.g. (Paradoxoros hermaphroditus)
Pinaceae, Cupressiaceae;
empyreumatic oils (burned organic 4. Ambergus - most valuable material; most
matter); heat without access of air expensive and luxurious perfume. Pathologic
(Incineration) product formed in the stomach of sperm whale.
when it feeds on squid or cattle fish. Ambrein
2. Enzymatic Hydrolysis - used for glycosidic
volatile oil. eg. Sinigrin - Myrosin – allyl
isothiocyanate

2017
14
 Constituent of Volatile Oil 2. Lemon oil
 rind of the fruit Citrus limon
Terpene - natural product whose structures are  Lemon oil
made up of isoprene units C5H8  constituent: Limonene
 uses: flavorant, stimulant, & carminative
Acetate – mevalonate pathways  Terpeneless oils: terpenes in
lemon oil results to a
Aromatic Compounds – Shikimate Pathways terebithenate odor. 95%
terpenes is removed by
Monoterpene 2 isoprene units distillation (more expensive)
Sesquiterpine 3 isoprene units 3. Citronella oil
Diterpene 4 isoprene units  leaves of Cymbopogon winterianus
 Lemongrass, Tanglad
Triterpene 6 isoprene units
 Constituent: Citronellal
 Herb for chicken and fish
 Concoction for insect repellant lotion.
HYDROCARBON VOLATILE OILS Teas
1. Turpentine Oil / Spirit of Turpentine o Lansones rind as incense ia an
 Pinus palustris insect repellent
 Preparations: o Mouthwas as insect repellant
 Rectified Turpentine Oil - during hiking (as spray) =
turpentine oil rectified by menthol
distillation from an aqueous
solution of NaOH 4. Hamamelis oil
 Turpentine Hydrate / Terpinol  Hamamelis virguniana
- HNO3 and rectified turpentine  Witch hazel
oil. Expectorant  Constituent: 2-hexanal
 Constituents: a-pinene, B-pinene  Hemorrhoidal preparations

ALCOHOL VOLATILE OIL KETONE VOLATILE OIL

1. Peppermint Oil
 Mentha piperita (Labiateae) 1. Camphor
 uses: flavorant, carminative, stimulant,  Cinnamomum camphora (Lauraceae)
counterirritant  camphor: kaafur-arabic name of Chalk
 constituent: menthol (antipruritic)  specific rotation of natural camphor: +41
 Japanese Peppermint Oil  specific rotation of synthetic camphor:
 Mentha arvensis var +43
piperascens  synthetic camphor is racemic
 high menthol concentration than  uses: antipruritic, rubefacient, anti-
M. piperita but it has inferior infective
flavor  crystal; eutectic mixture with menthol
2. Coriander Oil 2. Spearmint
 Coriandrum sativum  Mentha spicata (Lamiaceae)
 Chinese Parsley, Cilantro  use: flavorant, carminative
 Constituents: Linalool  constituent: (-) carvone
 (+) carvone has the same odor as that
3. Cardamom Oil of Caraway
 Eletaria cardamomum
 Constituents: cineole 3. Buchu oil
 Berosma betulina
4. Rose Oil
 Constituent: diosphenol
 Rosa gallica
 Uses: menstrual problems, carminative,
 Constituent: geraniol, nerol anti-rheumatic
5. Nerdli Oil PHENOL VOLATILE OIL
 Citus aurantium (orange) 1. Clove Oil
 Constituent: linalool  Eugenia caryophyllus (Myrtaceae)
 Eugenol
6. Pine Oil
 toothache drops; dental analgesic
 Pinus palustris
 Costituent: a-terpineol 2. Thyme
 Thymus vulgaris
ALDEHYDE VOLATILE OIL
 Thymol
1. Cinnamon oil
 use: antifungal and antibacterial agent;
 CInnamomum laureirii (Lauraceae) also used in cooking
 aka cassia oil
 constituent: Cinnamaldehyde
 uses: flavorant, carminative & antiseptic

2017
15
 3. Creosote oil
 Fagus grandiflorus
 Creosole, guaiacol
 Disinfectant

4. Juniper tar
 Juniperus oxyflorus
 Cadinene
 Anti-eczema in Polytar,; throat and
skin irritation, superficial wounds

PHENOLIC-ETHER VOLATILE OIL

1. Nutmeg or Myristic Oil
 Myristic fregrans
 flavorant and carminative;
HALLUCINOGEN
 constituents: safrole & myristicin

DATE-RAPE DRUGS

1. Flunitrazepam (Rohypnol) – roofless

2. Chloral Hydrate – KO drops
3. Liquid Ecstasy/GHB (Gamma
Hydroxybutyric acid)
4. Special K/Ketamine

2. Anise
 Pimpinella arisum
 Constituent: anisaldehyde, trans-
amethole

3. Fennel
 Foeniculum vulgare
 Constituent: fenchone, trans-anethole

4. Chinese Star Anise

 Bixa orellana
 Source of colorant; pigment – Bixin

OXIDE-VOLATILE OIL
1. Eucalyptus / Cineol
 Eucalyptus globulus (Myrtaceae)
 constituent: cineole (Cajuptol +
eucalyptol)
 Cajuput oil
 use: flavorant, antiseptic, diaphertic,
expectorant
 Vicks

ETHER VOLATILE OIL

1. Gaultheria Oil / Wintergreen / Betula /
Sweet Birch Oil
 Gaultheria precumbens
 Betula lenta
 main constituent: methylsalicylate
(efficascent oil)
 uses: flavorant, local irritant, antiseptic,
antirheumatic properties
 principal adulterant: synthetic
methylsalicylate
 most frangant among volatile oil

2017
16
 RESINS Podophyllin – caustic agent for worts

 amorphous product with complex chemical Podophyllum

nature
 firmed in schizogenous or in  Peltatin
schizolysogenous duct or cavities  Podophyllotoxin – Ethopuside and
 hard, transparent or translucent & when Tenoposide (anti-cancer)
heated they soften and melt
 complex mixture of: Jalap and Purganol – drastic purgative
 resin acid
 resin alcohol Mastic – mastian and mastichicacid
 resinotamnol
 ester Kava
 Resenes (w/o): B-complex neutral
substances devoid of characteristics  Styrylpyrone
 Endpoint of Volatile Oils o Yangonin
o Kawaiin
Resin Combinations o Methysticin – smooth muscle
1. Oleoresin - Resin + Volatile Oil relaxant, tranquillizer
2. Oleo-gum-Resin - Resin + Volatile oil + Gum
3. Balsam - mixture that contains cinnamic acid,
benzoic acid or both or ester of these acids
4. Resin Acids – oxyacids (-COOH and phenol)
5. Glycoresin – resin + carbohydrate

RESIN
1. Rosin / Colophony
 solid resin of Pinus palustris (Pine Tree)
 Pinaceae
 uses: stiffening agent in plaster, ceral

2. Podophyllum
 dried rhizome and roots of Podophyllum
peltatum (Berberidceae)
 aka Mayapple or Mandrake
 use: drastic purgative antimitotic
(papilomas) OLEORESIN
 constituent: podophylin 1. Turpentine / Gum Turpentine
 oleoresin from Pinus palustris
3. Eriodictyon / Yerba Santa (Pinaceae)
 dried leaf of Eriodictyon californicum  use: counterirritant
 use: flavorant; expectorant
 used to disguise the bitterness of 2. Capsicum / Cayenne pepper
quinine  dried ripe fruit of Capsicum frutescene
o paralysis of the taste buds (Solanaceae)
 C. Anuu var longum (Lusiana long
4. Jalap pepper)
 root of Exogonium jalap  African chilles
(Convulvulaceae)  use: irritant & carminative; vesicant
 use: cathartic & hydragogue  rubefacient and condiment

5. Mastic / Mastiche / Mastich 3. Ginger

 exudate of Pistacia lenticus  rhizome of Zingiber officinale
(Anacardiaceae) (Zingiberaceae)
 use: dental varnish to seal cavities  constituent: zingebol & bisabolene
 flavorant, condiment, stimulant,
6. Kava / Kava-Kava carminative, stomatitis, antibacterial
 root of Piper methysticum (Piperaceae)
 use: centrally acting skeletal muscle 4. White Pine
relaxant  bark of Pinus strolous
 use: expectorant
7. Cannabis / Indian Hemp / Marijuana / Pot
 tops of Cannabis sativa (Moraceae) 5. Balsam of Copaiba
 resin: Hashish  from Copaifera spp.
 Duquenois Test: violet on chloroform  use: genitourinary disinfectant, diuretic,
layer expectorant, laxative
 constituents:  not true balsam
 THC - tetrahydrocannabinol –
euphoric agent
 Cannabidiol (CBD) -
manufacture of rope
 Dequenois Test: Violet on
chloroform layer
 Nabilone

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 OLEO-GUM-RESIN 4. Benzoin Styrax
1. Myrrh / Gum Myrrhy  Sumatra(Indonesia)
 resin from Commiphora molmol  Siam (Thailand)
 ingredient of the embalming material of  use: antiseptic
Egyptians  closely related to benzoic acid
 use: astringent (preservative, antifungal, present in
 ingredient of astring-o-sol Whitfields Ointment)
 Al for CBT
2. Asafetida
 Ferula asafetida STEROID
 Devil’s dung  Compound with CPPP (3-(2-
 Most fetid odor Chlorophenyl)-1-phenyl-propenonein)
 Metabolites of melvalonic pathways
BALSAM  Sterols
 Wound healing property o Cholesterols – animals
 Perfumery o Ergosterol – fungi
o Phystosterol – plants
1. Storax or Styrax
 trunk of Liquidambar orientalis 1. Bile acids
 Levant’s Storax – a & B (50/50)  Primary
 use: pharmaceutic necessity for o Directly from cholesterol (liver)
compound benzoin tincture (tropical o Cholic acid, chenodexycholic
protectant) acid
o Benzoin  Secondary
o Storax o Permentation of primary bile
o Tolu Balsam acids by intestinal flora
o Aloe o Desoxycholic acid, Litocjolic
o Ethanol acid

2. Peru Balsam 2. Steroid Hormones

 Meroxylon pereirae  Glucocorticoids
 discoved by Jonathan Pereira o Carbohydrate metabolism
 use: local protectant & rubefacient o Anti-inflammatory
 parasiticide in certain skin disease o Cortisone, Cortisol
 Mineralocorticoid
3. Tolu Balsam o Electrolyte and water balance
 Meroxylon balsamum o Aldosterone
 use: pharmaceutic aid for compound  Sex Hormone
benzoin tincture; flavorant; expectorant o Male: Androgen, testosterone
o Female: Estrogen,
Progesterone

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 ALKALOIDS
2. Areca / Areca Nut / Betel Nut
 bitter, basic nitrogenous compounds  dried ripe seed of Areca catechu
 physiologically active  Nga-nga
 most of them end in “-ine”  anthelmintic – taenicide (Arecoline)
 they can be:  constituent: arecoline most abundant
 Primary amine: RNH2  tannin content causes esophageal CA
 Secondary amine: R2NH (Catechutannin)
 Tertiary amine: R3N
 insoluble or sparingly soluble in water 3. Lobelia
 remedy: convert them to salt (salt form  indian tobacco
is soluble in water)  Lobelia inflata (Lobeliaceae)
 eg. H2SO4 + Quinine = Quinine sulfate  substitute for tobacco
 Free Alkaloid - soluble in ether,  main constituent: Lobeline - has a
chloroform and other non-polar solvent similar, but weaker pharmacologic effect
(isolation of alkaloid) to that of nicotine (smoking
 Alkaloid reagent: form double salt with deterrant/CNS Stimulant) - Bantron
compound of mercury, gold, platinum
and other heavy metals TROPANE ALKALOIDS
 Valser’s Rgt – mercuric iodide  Solonaceous alkaloids
(white)
 Bouchdart’s Rgt – iodine in KI, 1. Alkaloids
most sensitive  Hyoscyamus or Henbane
 Marme’s Rgt – K Cd Iodide o leaves of Hyoscyamus miger,
 Sonhencheim’s Rgt – 0.04%
phosphomolybdic acid o Hot + bean  toxic to swine
 Scheibler’s Rgt –
phosphotungstic acid  Egyptian hyoscyamus or Egyptian
 Hager’s rgt – picric acid Henbane
 Gold compounds o Hyoscyamus muticus, 1.5%
 Tannic acid
 Wagners reagent - iodine in KI (red-  Daboisa
brown) o Duboisia myoporoides
 Mayer’s reagent - potassium mercuric o Commercial sources of Atropine
iodide (cream)
 Dragendorff’s reagent - potassium  Withania
bismuth iodide (orange) o Withania somnifera

2. Atropine
WIKI – Wagner’s – Iodine – KI  “deadly nightshade”
 obtained from Atropa belladonna
MaMeKI – Mayer’s – Mercuric – Iodide  uses:
 antidote for cholinesterase
Dra. KBIo – Dragendorff’s – Potassium Bistmuth Iodide inhibitor intoxication
(anticholinergic)
 antispasmodic
 antisialagogue
All are solid except: “CANS”  treatment of diarrhea together
 Coniine with opium alkaloid
 Coniium mculatum  pre-op to control secretion
 Poison hemlock – Socrates  counteract increase vagal
 Arecoline activity
 Nicotine  mydriatic & cyclopegic
 Sparteine  (+) inotropic agent
 Anti-arrythmic  (–) hyoscyamine (NatOccng)  Atropine
 Lupin – Lupinus mutabilis
 Scotchbroom – Cysticus caparius 3. Scopolamine or Hyoscine
 abundant in Datura fastuosa var. alba
 salt form: scopolamine & hyoscine Hbr
Sonhencheim’s Rgt – phosphomolybdic acid (Son in PMA)  uses:
Scheibler’s Rgt – phosphotungstic acid (Sch in PTA)  CNS depressant
(anticholinergic)
 calming delirium
PYRIDINE-PIPERIDINE ALKALOIDS  treatment of motion sickness
 Parent Compound: Ornithine (transdermal scopolamine) –
Trans-scopolamine/Transderm
1. Nicotine
 leaves of Nicotiana tabacum 4. Cocaine
 use: smoking deterrent; CNS stimulant  Huanuco coca – Erythroxylon coca
 Nicorete/Nicoderm   Truxillo coca – E. truxillense
 “crack / coke”
 Psychomotor stimulant, local anesthetic
 Brompton’s cocktail

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 QUINOLINE ALKALOIDS  “Store of Immortality”
1. Cinchona  Marquis test: Opioids (purple)
 Red cinchona bark – Cinchona
succiruba 5. Codeine
 Yellow cinchona bark – C. calisaya  most widely used opium alkaloid
 “Cinchonism” – temporary lost of obtained from the methylation of
hearing: Tinnitus first (ringing in ear) morphine or of thebaine
 Quinine  Methylmorphine
 Quinidine  use: narcotic analgesic, antitussive and
 Thalleioquin Test: fine blue fluorescence sedative, especially in allaying cough.
then green ppt less toxic and less habit forming than
morphine
2. Cuprea
 Cuprecaceae 6. Diacetylmorphine or Heroin
 Remijia purdieana  formed by acetylation of morphine
 Commercial source of quinidine  action is more pronounced than
morphine
ISOQUINOLINE ALKALOIDS  increase danger of habit forming, very
1. Ipecac potent
 dried rhizome & root of Cephaelius
ipecacuanha (Rubiaceae) 7. Apomorphine
 constituent: Emetine or  Morphine + HCl
methylcephaeline (used before as anti-  use: emetic
ameobacide), psychotrine, cephaeline
 use: syrup of ipecac (emetic) 8. Noscapine - Narcotine
 ipecac fluidextract is 14 times more  has no narcotic property, thus
potent sometimes called “Anarcotine”
 Ipecac + Opium = Dover’s powder  anti-tussive
(diaphoretic)
 Emetine - has antiamoebic property 9. Opiates
when administered orally  natural
 Paregoric (Camphor – Oral tincture)
 Laundanum a. Morphine
 Most important
2. Sanguinaria or Bloodroot  Most abundant
 dried rhizome of Sanguinaria  Narcotic analgesic
canadensis (Papaveraceae)  Discovered by Friedrich Wilhelm
 “Sanguinaria” means bloody, pertaining Adam Sertürner
to the color of the juice
 constituents: sanguinarine b. Codeine
 use: stimulating expectorant and emetic  Most widely used opium alkaloid
 Obtained from methylation of
3. Tubocurarine Chloride morphine
 aka Curare or South American arrow  Methylmophine (antitussive)
poison  P. Robuiquet
 dried extract of Strychnos casternaei
 Curare: woorari or urari which is an c. Noscapine
Indian word for poison  Non-narcotic opium alkaloid
 Standardization of Tubocurarine:  Antitussive
 Skeletal muscle relaxant  Anarcotin/Narcotine
 head drop assay in rabbits -
least amount of drug capable of d. Papeverine
producing muscle relaxation so  Smooth muscle relaxant
that the head of the animal  Antitussive
drops in a characteristic manner
 injected in neck e. Thebane
 Types
 Pot – clay 10. Opioids
 Tube – bamboo  Semi-synthetic morphine like
 Calabash – gourd compounds that have the same narcotic
and pain relieving property as that of
4. Opium or Gum Opium morphine but they are not habit-forming
 air dried milky exudates obtained by
incising the unriped poppy seed capsule a. Diacetylmorphine or Heroin
of Papaver somniferum (Papaveraceae)  Acetylation or morphine
 “Somniferum” - to produce sleep  Increase in danger of habit
 uses: formation – very potent
 stimulates then depresses nerve
responses b. Hydromorphone
 analgesic & hypnotic  more potent analgesic
 corrects excessive peristalsis  less frequents SE
 Only legal source is India

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 c. Apomorphin STEROIDAL ALKALOID
 Condensation of morphine + 1. Green hellebore / Veratum Viride
HCl  roots of Veratum viride
 Used as emetic  use: cardiac depressant
 side effect: hypotension and sedative
d. Hydrocodone
 antitussive 2. Black Hellebanore
 cardiac stimulant
INDOLE ALKALOIDS  more of a glycoside than an alkaloid
 Tryptophan
3. White hellebore / Europe Hellebore
1. Rauwolfia serpentina  roots of Veratum album
 dried root of Rauwolfia serpentine  hypotensive agent
 constituent: reserpine
 used in the treatment of snake bites to 4. Jervine
insanity  similar to cyclopamine
 hypotensive effect
 sedative and tranquilizing property B – C: (+) inotrope (more of a cardiac glycoside)
2. Catharanthus / Vinca – Christmas rose
 “Chichirika/Periwinkle
 dried whole plant from Catharanthus G – A: (–) inotrope (American)
roseus (Apocynaceae)
 constituent: Vincristine & Vinblastine W – E: insecticide (European)
 Lymph & Hodgkins

3. Nux Vomica ALKALOID AMINE

1. Ephedra or Ma Huang
 dried ripe seed of Strychnos nux vomica
 overground portion of Ephedra sinica
 constituent:
(Gnetaceae)
o Strychnine - toxic central
stimuilant  constituent: ephedrine a
 Mandelin’s Test: violet sympathomimetic
o Brucine - alcohol denaturant  uses: nasal decongestant;
o Strichnos ignatii - St. Ignatius bronchodilator
Bean (commercial source)
4. Physostigmine or Eserine 2. Colchicine
 from Physostigna venenosum  seed of Colchicum autumnale (liliaceea)
 Calabar, Ordeal or Esere bean  used inplant genetics because it can
 acetylcholinesterase inhibitor double the chromosome
 used in the treatment of glaucoma  gout suppresant: acute
 chronic gout: allopurinol + colchicine
5. Ergot
 dried sclerotium of Clavicep purpurea on
rye Secale cereole Allopurinol Colchicine
 constituent: ergonine & ergotamine
 Ergotamine - used with caffeine in the
treatment of migraine headache
o Constituents: A C
o Ergonovine – contraction of
uterus Acute Chronic
 Ergometrine
 Methylsergide –
prophylaxis of migraine
3. Abyssinian Tea / Khat
o Ergotamine
 fresh leaves of Catha edulis
 Methylergonamine maleate - oxtoxic
 constituents: Cathinone has mimics
agent
properties of amphetamine
 Methylsergid - prophylaxis of vascular
headache
4. Peyote / Mescal Button
 Dihydroergotamine mesylate - for
 “Shrooms”
migraine headache
 dried tops of Lophophora williamsii
 Lysergic acid diethylamide - most
 hallucinogenic and euphoric agent
active and specific psychomimetic drug
(LSD) – experimental psychosis  causes unusual & bizarre color
perception
IMIDAZOLE ALKALOID  constituents: Mescaline
1. Pilocarpine  Psilocybe – gane of peyote
 leaflet of Pilocarpus jaborandi o Psilocybine
 treatment of glaucoma

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 PURINE ALKALOID or METHYLXANTHINE
 purine base
 phosphodiesterase inhibitor
 Diuresis
 increases gastric secretion
 inhibit uterine contraction
 weak chronotropic & inotropic effect
 only grou of alkaloid that can’t be
precipitated by alkaloidal reagents

1. Caffeine
 Kola/Cola/Kolantus - dried cotyledon of
Cola nitida
 Coffee bean - dried seed of
Coffea Arabica
 Amaic acid test: red-brown/transient
purple

2. Theophylline
 leaf buds of Camellia sinensis
(Theaceae)
 treatment of bronchial asthma C. robusta, C. liberica
 tocolytic agent
 Aminophylline Chlorogenic acid + caffeine
o semi-synthetic theophylline + caffeole = volatile oil (smell)
derivative
o not used in pediatric patients Decaffeinated coffee = 0.08% caffeine
because of narrow therapeutic
index (use Theophylline instead) Brewed fresh – Green (China, Japan)
o for bronchial asthma
Fermented – Black (India, Sri Lanka – Ceylon)
3. Theobromine
 seed of Theobroma cacao Brewed Tea – can cause esophageal
 diuretic in cardiac & pulmonary edema
contraction
(tx: add milk)

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