PHARMACOGNOSY

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PHARMACOGNOSY CRUDE DRUGS

 Applied science -> biological, biochemical and economic – vegetable or animal drugs consists of natural substances that
features of drugs of biological origin and their constituents had undergone only the processes of collection and drying; plant
 Medicinal products in their crude or unprepared form exudates

HISTORY OF PHARMACOGNOSY Natural Substances – formed in nature; whole plants or parts;

animals or organs; no molecular modifications had been made
Bablylonians
Derivatives of Extractives – chief principle or constituents of
 Laws of Hammurabi (172 BC); clay models of human body;
crude drugs that are separated and used in a specific manner
medicinal effects of 250 plants; mages and physician; wheat
 Menstruum – solvent; liquid/liquid mixture used to extract
and barley
active principle
 Marc – undissolved portion of the drug that remarks after
Ayurveta (2500 BC)
extraction process is completed
 Traditional medicine; “Science of life”; Mother of all healing
arts
Methods of Extraction
 Charaka – text on internal medicine
 Infusion – hot water (ex. tea); short contact of action
 Sushruta – 184 chapters; 1120 illness
 Maceration – soaked in solvent for long period of time
 Percolation – passage through percolate (ex. Simple Syrup
Egyptians (Ebers papyrus – 1150 BC)
USP)
 Embalming; George Ebers; priest and doctors; human anatomy
 Digestion - <35-40oC
and use of plants
 Decoction – boiling water
Greeks  Liquid-Liquid Extraction Partitioning  Distillation
 Dioscorides – wrote “De Materia Medica” or The Medicinal
Indigenous Plants – plants growing in their native countries (ex.
material; aloe, belladonna, colchicum, ergot, opium; 600
Rinorea niccolifera – metal eating plant; more on nickel)
plants
Naturalized Plants – plants that grow in foreign land other than
 Claudius Galen – described methods and processes of
their native homes
preparing formulas containing plant and animal drug; FATHER
OF PHARMACEUTICAL COMPOUNDING
Preparation of Crude Drugs
1. Collection – ensuring the true natural source of the drug:
Germans
improper collection, collection time, highest content
 CA Seydler (1815) – coined the term, “pharmacognosy” from
 Harvesting – specific or proper season; manual labor vs
“pharmakon” and “gnosis” in Analecta Pharmacognistica
mechanical devices
 JA Schidt (1811) – used the word, “pharmacognosy”; Lehrbuck
2. Drying – remove moisture to prevent bacterial and fungal
de Materia Medica; described study of medicinal plants and
growth with enzymatic degradation; fixed constituents,
their properties
facilitates grinding and milling; converts plants to convenient
 Fluckiger – simultaneous application of various scientific
form
 disciplines with the object of acquiring drugs from every point
3. Curing – special drying process that enhances properties of
of view
plants’ active ingredients
 Pellitier and Caventou – Quinine 4. Garbling – final step in preparation of crude drugs; removal of
 Freidrich Serturner - Morphine extraneous matter
*Last Packaging, Storage, Preservation – protection and
marketability; maintain high degree of quality of drug
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Evaluation of Crude Drugs – determine quality and purity;
qualitative (intrinsic value of drug; type of medicinal prinnciples)
and quantitative (amount)
 Organoleptic Evaluation – organs of senses; evaluates
macroscopic appearance of drug
 Microscopic – evaluate in a cellular level
 Pharmacologic Evaluation
o Bioassays – assays using living animals or excised organs to
evaluate effects of drugs
 Chemical Evaluation – assay of active constituents using
chemicals (titration); best determination of official potency
CLASSIFICATION OF DRUGS
1. Morphology – forms; plant part used; convenient but no
chemical correlation
2. Taxonomic (Lireus) – evolutionary development; no
correlation on chemical and biological activity
 Phylogeny – natural relationship that occurs among plants
and animals
3. Pharmacologic – based on therapeutic effect on body
4. Chemical – preferred method of classification – based-active
constituents that are present; phytochemical studies but
ambiguous at times
Active Constituents – considered secondary metabolites;
through drug biosynthesis or biogenesis
BIOGENESIS
 Ontogemy or Stage of Development
Ex. Cannabis sativa (cannabidiol – plant is young; cannabinol
– mature plant)
 Heredity – same but not the same
 Environment
I. CARBOHYDRATES
 Polyhydric aldehyde or ketone alcohols that contain C, H, and
O
 H and O has same ratio as that of water, thus named CARBO +
HYDRATES Photo
 First product of synthesis [C•H2O]n
 Xylem – H2O
 Phloem – nutrients – food (∆ source; ∆ storage; structure)
Most abundant organic molecule in nature
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A. CLASSIFICATION OF CARBOHYDRATES
I. MONOSACCHARIDES – simplest carbohydrate unit; cannot be
hydrolyzed; identification test: Benedicts and Barfoed’s =
brick red ppt.; *neuramonic – aka sialic
PENTOSES
 Xylose – “wood sugar”; obtained from boiling corn cobs, straw;
diagnostic aid for intestinal malabsorption; absorbed but not
metabolized
o Xylan -> Xylose (aldehyde) -> xylulose (ketoses)
HEXOSES – most important monosaccharide
 Glucose – aldohexose; aldehyde group is present in C1;
reducing sugar as determined by Benedict’s Test; occurs as
linear and cylic;
o β-D-Glucose – most abundant
o D-Glucose – aka Dextrose, Blood Sugar, Grape Sugar,
Physiologic Sugar
o Uses:
 Parenteral – rigorously purified; as nutrient
 Pharmaceutic necessity – less rigorous purification; Liquid
Glucose – syrupy liquid; incomplete acid hydrolysis of
starch; almost colorless and taste sweet; Dextrose
excipient – crystalline sweetening agent (Oral Glucose
Tolerance Test – 75g)
 Fructose – ketohexose = (+)Seliwanoff’s Test: pink/red; ketone
group is present in C2; reducing sugar; fruit sugar; sweet fruits
and honey; aka Levulose (sweetest monosaccharide); obtained
from inversion of aq. sucrose solution; honey (mostly sucrose)
o High Fructose Sweeteners – isomerization of glucose
isomers from Streptomyces sp.
o Uses:
 Food for diabetic
 Ingredient in infant feeding formula
 Ingredient in Fructose injection nutruient
 Galactose – aldohexose; “Brain Sugar”; C4 epimer of glucose
(C2 – mannose); milk:lactose::neuronal fibers:galactosides;
Gaucher’s Disease; (+) Mucic acid and Phenylhydralazine =
crystal formation (osazone crystals)
II. DISACCHARIDES – composed of two monosaccharide units;
formed via dehydration synthesis; glycosidic bond
 Sucrose – “table sugar”; obtained from:
o Saccharum officianarum (sugar cane) – (+) lime = decreased
albumin; use SO2  clear = clarification
o Beta vulgaris (sugar beets) – cossettes (“cut limps livers” –
chop finely)
o Acer saccharum (sugar maple)
- non-reducing sugar: (-)Benedict’s Test
- glucose + fructose, α-1,2 bond
- uses: demulcent, sweetening agent to mask taste, coating
agent, preservative (85%), production of syrups, retards
oxidations
© MANOR REVIEW CENTER NOTES (K.L)
 - Molasses – residual dark colored syrup after complete III. POLYSACCHARIDES
crystallization of sucrose; only disaccharide in free state;  Homoglycans – polysaccharides that yield one type of
food and ethanol industry monosaccharide unit upon hydrolysis
 Maltose – malt sugar; produced-germination of barley; o Starch – temporary storage form of photosynthetic products
glucose + glucose, α-1,4 bond; major degradation product of from:
starch; reducing sugar (beer, ovaltine, cereal drinks); glu + glu  Zea mays – corn
+ glu = maltotriose (oligosaccharide – 3-10C)  Triticum aestivum – wheat
 Lactose – milk sugar (cow’s milk); glucose + galactose, β-1,4  Solanum tuberosum – potato
bond; reducing sugar; milk products:  Oryza sativa – rice
1. Whole milk –(sit)-> butter  Maranta arundinacea – arrowroot
2. Butter milk –(churn)-> cream  Constituents:
3. Skimmed milk -> whey Bases of Amylose Amylopectin
(rennin – young calf)  coagulum –(tx)-> cheese Differences
Structure Linear/Helical Branched
* Kamyss – fermented spoiled milk
250-300 units (every 25-30 mins)
* Condensed Milk – partial condense autoclave, evapo α-1,4 1000 or more
 Lactulose – fructose + galactose, β-1,4 bond; alkaline α-1,4 and α-1,6
rearrangement of lactose; converted by lactose to lactic and Solubility Insoluble Soluble
acetic acid, which causes irritation of the intestines and in water
subsequent cathartics – ideally used with MI and stroke Iodine test Deep/Dark blue Blue violet/purple
Enzymes that breaks down starches:
1. Alpha amylase – present in pancreatic juice and saliva;
PRODUCTS OF OXIDATIVE METABOLISM
*metabolism/breakdown of carbohydrates starts in
 Cherry Juice – ripe fruit of Prunus cerasus (Rosaceae); contains
mouth
pectin and 1% malic acid; cherry syrup
2. Beta amylase – hydrolyses starch to nearly pure
 Plant Acids – uses: acidulants in effervescent formulations;
maltose
component of buffer systems
Uses: tablet filler, binder and disintegrant; antidote for
o Citric Acid – Scheele – lemon juice (1784); citric –
iodine poisoning
Tricarboxylic acid (TCA) –(Deniges Test)-> tartaric (by
Starch Preparations:
product, dicarboxylic) = wine
1. Pregelatinized starch – chemically or mechanically
o Lactic Acid – acidulant – infant feeding formula, feminine
processed to rupture all or part of granules; tablet
wash (0.2% chlohexidine – vaginal; 0.6% - mouth) – (INSERT)
binder
 Alcohol/Ethanol – 95% ethanol by volume 15.56oC; product of
2. Sodium starch glycollate – disintegrating agent
fermentation; undergo process of distillation to concentration
3. Hetastarch - >90-99% amylopectin; plasma expander;
the alcohol content to 40-55%; low conc. – CNS stimulant; high
hydroxyethylstarch; Voluben®
conc. – CNS depressant
4. Glutens – tacky proteins that impedes flow of starch
o Brandy - wine
o Glycogen – storage polysaccharide in animals; more
o Whiskey – malted grain
branched than starch (every 10); red color with iodine
o Rhum - molasses
o Inulin – polyfructan of fructofuranose; Chicorium intybus
o Diluted Alcohol – 48.4-49.5% ethanol at 15.56% oC
(Asteraceae) – chicory root; improve digestion; Uses:
ingredient in culture media; evaluation of renal function
PRODUCTS OF REDUCTIVE METABOLISM
o Dextran – glucosan; Leuconostoc mesenteroides; plasma
 Mannitol – from manna, dried exudate of Franxinus ornus;
expander
osmotic diuretic and osmotic laxative, GFR; used in people
o Cellulose – structural polysaccharide in plants (from the hair
with neurological trauma
of seeds of Gossypium hirsutum)
 Sorbitol – from berries of mountain ash, Sorbus aucuparia; aka
 Purified/Absorbent Cotton – surgical dressing
D-glucitol; tastes ½ sweet as sugar; used in manufacture of
 Soluble Guncotton/Pyroxylin – formed by action of nitric
toothpaste and chewing gum  xylitol as alternative
and sulfuric acid on cotton; Other ingredients: castor oil
(flexibility); camphor (water-proof); Use: topical
protectant
 Other Cellulose Derivatives – cellulose acetatephthalate
(CAP) – coating agent; methylcellulose and ethycellulose –
artificial tears

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 o Chitin – structural polysaccharides in animals; exoskeleton:  SEED GUMS
mollusks and arthropods; homoglycan of N- GUM SOURCE
acetylglucosamine Psyllium Seed coat of:
 Chitosan – deacetylation of chitin; water purification Plantago psyllium – Spanish
Plantago ovata – Blonde
 Glucosamine – acid deacetylation and hydrolysis of chitin
Cydonium/Quince Seed Ripe seed of Cydonia vulgaris
 Heteroglycans – polysaccharides that yield more than one Guar Gum or Guaran Endosperm of Cyamopsis
types of monosaccharide units upon hydrolysis tetragonolobus
Locust Bean Gum/Carob Pulp Endosperm of the seed of
or St. John’s Bread Ceratonia siliqua Chocolate substitute
B. GUMS AND MUCILAGES  MICROBIAL GUM
 natural plant hydrocolloids that may be classified as anionic or GUM SOURCE NOTES
non-ionic polysaccharides Xanthan Action of Has a pseudoplastic activity
 produced by plants as a protective after injury; upon Gum Xanthomonas enable toothpastes and
hydrolysis, they yield arabinose, galactose, glucose, mannose, campestris on ointments to spread easily
carbohydrates
xylose and other uronic acid derivatives
 Pb acetate and alcohol
LINEAR BRANCHED C. PLANT EXTRACTIVES
Solubility Less More  Pectin – intracellular cementing materials; partially
Stability Less More methoxylated galacturonic acid (swelling); extract of inner
Use Viscosity enhancers Gelating agents
portion of rind of citrus fruits (pomelo, grapefruit, orange,
ponkan, lemon, calamansi, dalanghita, apple) and apple
GUMS MUCILAGES
Production Pathologic (injury) Physiologic pomace; antidiarrheal agent;
(natural) o Kaopectate – Kaolin + Pectin -> antidiarrheal preparation
Solubility in water Readily soluble Slimy mass o Protopectin – unripe
o Pectin (sol) – just ripe
PLANT EXUDATES BOTANICAL SOURCE o Pectic acid – overripe
Acacia - Gum Arabic -> arabin -> K, Ca, Acacia Senegal
Mg, Arabic acid; mucilage; emulsifier;
suspending agent (33-35%); 12% H2O D. GLYCOSIDES
content; <60% alcohol  Heteroglycans; “sugar ethers”; BETA form occur in plants; N-,
S-, C-, O, alpha or beta; regulatory, protective and sanitary
Tragacanth Astragalus gummifer
Types: vermiform (worm); taragacanth
compounds
sorts (tear)  Components: glycone (acts as vehicle; inactive) and aglycone
Constituents: Bassorin (swells: 2/3); (genin; basis for classification; active)
traganthin (dissolves: 1/3)  CARDIAC GLYCOSIDES
SA: 5-6%
o Unsaturated steroidal aglycone tests
K: galactomannan -> bulk laxative
Karaya – most fetid gum Sterculia gum Sterculia urens  Libermann-Burchard = blue/green; yellow for saturated
Indian – Ghatti; alternative fro acacia Anogeissus latifolia  Salkowski = red/violet
 MARINE GUMS o 2-deoxy sugar glycone test
GUM SOURCE CONSTITUENTS  Keller-Killanii test = reddish brown)
Agar or Algae o CARDENOLIDES vs BUFADIENOLIDES (C235-B246)
Japanese Gelidium cartilagineum Agarose CARDENOLIDES BUFADIENOLIDES
Isinglas Gracilaria confervoides Agaropectin - Common (active) - Rare (Bufo sp); (inactive)
Algin Brown Seaweeds Mannuronic acid - C-23 α and β unsaturated 5- - C-24 doubly unsaturated 6-
Macrocystis pyrifera membered lactone ring membered lactone ring
Carageenan Red Algae Kappa-gelling o Digoxin – H2O; Digitoxin – lipid; Desllanatoside –
or Irish Moss Chondrus crispus component
digitalization = rapid
Gigartina mamillosa Iota-gelling
component o Convallaria – Convallatoxin – Lily of the Valley
Lambda – non-gelling o Apocynum – Dogbane – cymarine
component o Adonis – Pheasant’s Eye – adonitoxin
Danish Agar Furcellaria fastigiata Kappa o Black Hellebore – Xmas Rose – hellebrin
o Strophantus – K strophantin (good) G strophantin (bad) –
(toxic)- Oubain
o Sqiuill – Scillarenin -> expectorant (bufadienolides)
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 ANTHRAQUINONE GLYCOSIDES
o Aglycone: Anthracene
o Use: cathartic <drastic>
o Derivative color: orange
o Identification Test: Borntranger’s Test
o Cascara Sagrada – Rhamnus purshianus
i. Constituents:
Cascarosides A and B – optical isomers of barbaloin
Cascarosides C and D – optical isomers of chrysaloin
ii. LANE’s Pill – casanthol, purifiesd mix of anthranol
glycosides
iii. Cured in MgO for 1 year
o Frangula or Buckthorn Bark – Rhamnus frangula
i. Present in Movicol® – Karaya (laxative) + Frangula
(cathartics); for constipation
o Aloe – dried latex or juice of Aloe barbadensis or Aloe vera
<Curacao aloe>; hybrids of Aloe ferox with Aloe Africana and
Aloe spicata <Cape aloe>; (cathartics and BURNS)
i. Constituents: barbaloins and aloe emodin
o Rhubarb – glucohein
Rheum or Chinese Rhubarb Indian Rhubarb or Himalayan
(Therapeutic) Rhubarb (Ornamental)
Rheum officinale Rheum emodi
Rheum palmatum Rheum webbianum
o Senna – dried leaflet of Cassia acutifolia <Alexandria>;
Cassia angustifolia <Tinnevelly>; cultivated in wat lands
resembling rice paddies; derivative color: blue green
 Constituents: Sennosides A, B, C, and D
o Chrysarobin – from Goa powder, Andira araroba; only
anthraquinone glycoside that is NOT used as cathartic
because it is very irritating; used as keratolytic; hot benzene
is used to extract this substance
 SAPONINS – foam upon shakin (froth test); bitter, acrid taste;
sternutatory (may irritate mucous membrane = sneezing);
destroy RBCs of cold blooded animals -> fish poisons; froth,
hemolysis, capillary
o Glycyrrhiza or Licorice – dried roots of Glycyrrhiza glabra;
increase foaminess of beer
 Constituents: glycrrrhizia, glycyrrhziac acid
o Dioscorea or Yam
 Dioscorea spiculiflora – contains diosgenin which is a
glucocorticoid precursor;
 Dioscorea floribunda – best source of steroids;
 Diosgenin – anti-inflammatory
o Ginseng – Panax ginseng (Asia); Panax quinquefolius
(American); aphrodisiac and an adaptogen
 Constituents: panaxosides, ginsenosides,
chikusetsusaponins
 CYANOPHOIC OR CYANOGENIC GLYCOSIDES
o Amygdalin (H2O and amygdalase)  mandelonitrile glucose
(H2O and prunase)  mandelonitrile + glucose 
benzaldehyde +HCN
o Rosaceae
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o Emulsin – amygdalase and prunase (collectively)
o APE = A+P+E
o Guingard’s Test = brick red/red coloration
 Bitter almond – Prunus amygdalus; source of Laetrile (Vit
B17) – controversial treatment for sickle cell anemia
 Wild cherry – Prunus serotina; flavored vehicle,
expectorant and sedative
 Apricots – Prunus armeniaca
 ISOTHIOCYANATE GLYCOSIDES
o Rapeseed – Brassicca napus; gluconapin
o Watercress – Nastutium officinale; gluconasturtiin
o Odor test  mustard smell (volatile); garlic (allicin)
o Ferric chloride test  blood red (non-volatile)
o Black Mustart or Sinapis Nigra – Brassica nigra – sinigrin
Sinigrin/sinalbin –(myrosinase)-> allyl/acrinyl
o White Mustard – Brassica alba – sinalbin
 FLAVONOL GLYCOSIDES – flavonoids or bioflavonoids from
citrus fruits and soya
o Rutin and Hesperidin – vitamin P or permeability factors;
treatment of capillary bleeding secondary to capillary
fragility
o Hesperitin, Diosmin, and Naringen – treatment of
symptoms of common colds
o Yellow Pigment – rutin and quercetin
o Milk Thistle – Silybum marianum; silibinin, silymarin,
hepatoprotective
o Gingko – Ginggko biloba; gingkolides, bilolabides; memory
enhancement
 ALCOHOL GLYCOSIDES – Salicin – salix and populous
o Salix purpurea and Salix fragilis
o Aglycone: saligenin
o Anti-inflammatory; anti-rheumatic
o Tests:
 Fehling’s – brick red
 Nessler’s – gray
 Tollen’s – silver mirror
 Schiff’s – recolorization
 ALDEHYDE GLYCOSIDES
o Vanilla – cured fruit of Vanilla planifolia (orchidaceae) –
Mexican, Vera Cruz, Bourbon
 Constituent: vanillin
 Use: flavoring agents
 PHENOL GLYCOSIDES
o Urva ursi – dried leaf of Arctostaphylos urva ursi
 Constituents: arbutin (hydroquinone + sugar)
 Use: astringent and diuretic
o Poison Ivy (Rhus radicans) and Poison Oak (Rhus
toxicondendron); uroshiol – delayed contact dermatitis (type
IV)
© MANOR REVIEW CENTER NOTES (K.L)
 LACTONE GLYCOSIDES deposit ova); constituent: tannic acid (Gallic + Ellagic = Tannic
o Coumarin – from Tonka beans, Dipteryx odorata; [GET])  astringent
constitutents: dicoumarol bishydroxycoumarin   Chinese/Japanese Gall – Rhus chinensis; Aphis sp. – gallic acid
anticoagulant, Warfarin; Test for unsaturated lactone: (Bismuth subgallate – protectant; deodorizer for flatulence)
Kedde’s = blue-violet
o Cantharides – from dried insect, Cantharis vesicatoria; III. LIPIDS
Russian/Spanish fly; Blistering fly FIXED OILS FATS WAXES
 Constituents: cantharidin-irritant, vesicant and  Long chain fatty  Long chain fatty  Long chain fatty
rubefacient acids + glycerol acids + glycerol acids + high
 Causes priaprism – sustained erection  From vegetables  From animals molecular weight
o Psoralens – photosensitizing furocoumarins; from Bishop’s  Liquid at room  Sold at room temp alcohol (cetyl
flower, Ammi majus temp  EXCEPTIONS: alcohol, stearyl
 EXCEPTIONS: Liquid F: Cod liver alcohol)
 Methoxsalen – repigmentation in vitiligo Solid FO – oil  EXCEPTIONS:
 Trioxsalen Theobroma, Liquid W: Jojoba
Myristica oil
USE: storage USE: storage USE: protectant
II. TANNINS
 Complex substances or polypeptides that are difficult to
 Fatty Acids
separate because they do not crystallize
o Saturated – capric, lauric, myristic, palmitic, stearic,
 Phenolic in nature; non-crystallizable polyphenols; protein
arachidic
precipitant (astringent); found in barks and leaves
o Unsaturated (=) – palmitoleic, oleic, linoleic, linolenic,
 Local sources: arachodonic
o Guava – Psidium guajava
 Uses: emollients; vehicles for IM injection (COCOPESE);
o Kamachile – Pithecolobium dulce
cathartic (castor oil); soap production; increase caloric value
o Duhat – Syzigium cumini
(TPN)
 Characteristics:
 USP Tests:
o Acidic
o Acid value or Acid number – mg of KOH needed to neutralize
o Sharp puckering taste
free FAs
o Causes precipitation of alkaloids
o Saponification value – mg of KOH needed to saponify the
o Industrial – leather and ink
esters
o Clinical – astringents – GI or skin, treatment of burns
o Iodine value – g of iodine absorbed in 100g of sample
 Chemical classes: (True tannins vs Pseudo tannins –
 Expression – cold-pressed oil; hot-pressed oil; only from fixed
chlorogenic acid and catechins)
oils
A. True Tannins – animal skin  leather; (+) Gold Beater’s Skin
 Rendering – fats
Test
 Solvent extraction – fats; hexane – best solvent for extracting
i. Hydrolyzable – readily hydrolyzed to yield phenolic acids
fats
and sugars
 Types of oils – ability to absorb oxygen; oxygen saturates
 Pyrogallol
double bonds forming oxides that polymerize to form films;
 Leather: bloom
paint industry
 FeCl3 = blue-black; Br2 test = (-)
IODINE VALUE RANGE EXAMPLES
ii. Non-hydrolyzable (aka Condensed Tannins/
Non-drying <100 Olive; Almond
Phlobatannins) – results from condensation of catechin Semi-drying 100-120 Cottonseed; Sesame
and leucocyanidin Drying >120 Linseed; Cod liver oil
 tend to polymerize  phlobaphenes (red colored  Reactions of Lipids
product) o Hydrogenation – liquid oil to semi-solid fat; passing of H
 Leather: tanners red with Pd/Ni in 160-200oC; shortening and cooking fat
 FeCl3 = green-black; Br2 test = (+) o Sulfation – reaction with sulfuric acid; temp at chilling;
B. Pseudo Tannin sulfates adds to double bonds, surfactants
 Hamamelis Leaf – Witch Hazel Leaf, dried leaf of Hamamelis
viriniana; constituent: hamamelitanin; used for hemorrhoids
 Nutgall – excrescence obtained from young twigs of Quercus
infectoria, Fagacea (when Cynips tinctoria bores a hole to

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IV. FIXED OILS  Cod Liver Oil – from Gadus morrhua; sclerosing agent to
obliterate varicose veins; source of vitamin A and D (Scott’s
 SEED OILS
FIXED OIL BOTANICAL SOURCE
emulsion)
Cottonseed Oil – IM injection; not Gossypium hirsutum  Undecylenic Acid – pyrolysis of ricinoleic acid from castor oil;
edible; constituent: gossypol –x-> male has antifungal property
sterility; ID test: Halphen/Bevan  Azelaic Acid – onolysis of Castor oil; anti-acne
Sesame Seed Oil – Benne/Teel Oil; Sesmum indicum
uses: IM injection, edible; constituent:
sesamol (phenol) – self-preserving + VI. WAXES
lignin  sesamolin & pyrethrin   Spremaceti – head of spermwhale, Physeter macrocephalus;
insecticides; ID test: Bauduoin
synthetic spermaceti – cetyl ester wax
Coconut Oil – constituents: lauric, Cocos nucifera
myristic, triclycerides  Jojoba Oil – seeds of Simmondsia chinensis, Buxaceae;
Castor Oil – tangan-tangan; ricinoleic Ricinus communis hydrogenated form resembles spermaceti; eicosenoic acids:
(good) - cathartic eicosenol and docosenol
trcinoleic (good)  Beeswas or Yellow Wax – honeycomb of bees, Apis mellifera;
ricin (toxic) = abrin (jequirity bean)
stiffening agent in plasters and cerates; White Wax – bleached
Peanut Oil – peanut oil cake; peanut Arachis hypogaea
butter; afflotoxin  aspergillus (due to yellow wax; myricyl pamitate
improper storage and drying)  Carnuba Wax – leaves of Copernicia prunifera; myricyl
Soybean Oil – stigmasterol - steroid; Glycine soja cerotate
lecithin – regulate cholesterol;
antilipemic agents
Corn Oil – germ oil cake – IM injection; Zea mays VII. VOLATILE OILS
antilipemic agents; Hydrogenated  Odorous principle in carious plants
volatile oils = sergers  Colorless and photosensitive; light resistant tight container in
Safflower Oil – antilipemic agents Carthamus tinctoria
a cool and dry place
Sunflower Oil – antilipemic agents Helianthus anuus
Ethiodized Oil Injection Iodine addition  Undergoes auto-oxidation and resinification
product of ethyl ester  Plant families:
of fatty acid of Poppy o Glandular hairs or trichomes (lamiaceae  labiatae)
seed o Modified parenchymal cells  piperaceae
 PERICARP OILS o Oil tubes or vittae  apiacea (umbelliferae)
FIXED OIL BOTANICAL NOTES o Lysigenous and schizogenous passages  pinaceae and
SOURCE
rutaceae
Olive Oil – Olea Grades:
ID test: europaea 1. First Grade Virgin Olive Oil –  Physical characteristics:
Milon’s extracted with less pressure o Possess characteristic odors, high refractive index, optically
2. Second Grade Virgin Olive Oil – active, immiscible in H2O but can be sufficiently be soluble
pulp in #1 is extracted with more to impart odor in water  aromatic water
pressure
VOLATILE OILS FIXED OILS
3. Technical Oil – extracted with
hot water Distillation Saponification
4. Sulfur Grade – extracted with Resinification Rancidity
(-) Grease Spot (+) Grease Spot
Carbon disulfide; inferior quality
5. Tournant Oil – fallen and Methods of Obtaining Volatile Oils
decomposing fruits  Distillation
o Water Distillation – dry sample; turpentine oil
V. FATS AND RELATED COMPOUNDS o Water and Steam Distillation – dry sample; clove and
cinnamon oil
 Theobroma Oil – Theobroma cocao; food for the gods
o Steam Distillation - peppermint and spearmint
o Uses: cocoa syrup – beverage; cocoa butter – suppository
o Destructive Distillation – empyreumatic oils (heat without
base (melts at 30-35oC)
access of air); pinaceae and cuppressiaceae – only family to
o Nibs  prepared cacao/breakfast cacao
use destructive distillation (“char”)
 Lanolin – purified fatlike substance from wool of sheep Ovis
 Enzymatic Actions – mustards
aries, Boviidae; contains 25% water; Uses: water absorbable
ointment base; emollient  Expressions
o Anhydrous lanolin – woolfat (contains 0.25% water) o Ecuellle and Piquer – rolling a fruit in a trough line with
sharp tiny projections enough to puncture the rind – citrus
fruit
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 o Enfleurage – flower petals (or small plant part) on a fatty 1. Camphor – Cinnamomum camphora; natural
pomade followed by EtOH extraction camphor: (+); synthetic camphor: racemic (-); anti
Components of Volatile Oil pruritic, rubefacient, anti-infective
STEREOPTENE ELEOPLENESES 2. Spearmint – Mentha spicata; carvone (-); (+) carvone
- Solid oxidized hydrocarbon portion - Liquid hydrocarbon portion – same odor as caraway (Carum carvi)
- Menthol - Methysalicylate 3. Buchu Oil – Berosma betulina; diosphenol; menstrual
- Amenthol - Encalyptol
- Thymol - Eugenol problem, carminative, anti-rheumatic
4. Wormwood/Quinghaosu – Artemia annua; Artemisia
 Medicinal and commercial use: fabrication of perfumes ketone and camphor; anti-malarial  artemisinin,
o Top Notes – (smell – minute to hour); most volatile product; artenether, artesunate
leave skin readily – lemon (limonene – most used flavorant), Phenol Volatile Oil
lavender, anise oil 1. Clove Oil – Engenia caryophyllus; eugenol; toothache
o Middle Notes – (3-6 hours); intermediate tenacity and drops, dental analgesic
volatility – thyme, neroli and rose oil 2. Thyme – Thymus vulgaris; thymol  antifungal and
o Base Notes – (long hours); low volatility and high tenacity; antibacterial
aka Fixatives = staying power 3. Creosole Oil – Fagus grandiflorus; creosole 
 Musk – dried secretion from the preputial follicles of the disinfectant, guiacol
male musk deer of Asia, Moschus spp – muskane 4. Jupiter Tar – Juniperus oxycedrus; cadinene; anti-
 Civet – glandular secretion appearing in an outwardly exzema  Polytar®
discharging pockets of civet cat, Paracloxutus hermaphrodites Phenolic Ether Volatile Oil
 Amber gris – most valuable material; pathologic product 1. Nutmeg/Myristica Oil – Myristica fragrans;
formed in stomach of spermwhale when if feeds on squid or constitentuents: safrole and myristicin; halloahogen
cattlefish (ambrein) 2. Anise Pimpenella – Pimpenella anisum –
 Constituents of Volatile Oils: anisaldehyde, transanethol
o Terpenes – natural products whose structure are made up 3. Fennel – Freniculum vulgare; fendiole, transanethole
of isoprene units:
 Monoterpene – 2  Sesquiterpene - 3
Hydrocarbon Volatile Oils  Diterpene - 4
1. Turpentine Oil – Pinus palustris; rectified tuperntine;  Triterpene - 6
terpinhydrate/terpinol – expectorant; α and β   Tetraterpene – 8
pinene o Acetate-Mevalonate Pathways
** turpentine oil + NaOH = rectified turpentine o Shikimic Pathway – aromatic compound
** RT + HNO3 = terpinhydrate/terpinol
2. Peppermint Oil – Mentha piperita; menthol VIII. RESIN AND RESIN COMBINATION
(antipruritic)  (+) synthetic, (-) natural; Japanese RESINS – amorphous products with complex chemical nature;
Peppermint Oil – Mentha arvensis; increase menthol hard transparent or translucent and when heated they soften
concentration; flavorant, carminative, stimulant and melt; complex mixtures of:
counter – irritant *****INSERT HERE*********  Resin acids
Aldehyde Volatile Oil  Resin alcohols
1. Cinnamon Oil – Cinnamomum loureiril; Cinnamomum  Resinotannols
zeylanicum; Cinnamomum cassia (aka cassia oil);  Esters
constituent: cinnamaldehyde; uses: flavoring,  Resenes – B-complex neutral substances devoid of
carminative, antiseptic characteristics
2. Lemon Peel Oil – rind of the fruit Citrus limon; lemon RESIN SOURCE CONSTITUENTS/NOTES
oil; citral and limonene Rosin/Colophony Pinus palustris
3. Citronella Oil – leaves of Cymbopogon winterianus – Podophyllum Podophyllum Podophyllin – caustic agent
tanglad; citronellal; insect repellant peltatum for warts
4. Hamamelis Oil – Hamamelis virginiana; 2-hexanal; Peltatin – purgative
Podophyllotoxin –
hemorrhodal preparation etoposide, tenoposide
Ketone Volatile Oil Eriodictyon/Yerba Eriodictyon
Santa californicum

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 Jalap Exogonium Jalapin and purganol – o Secondary – fermentation of primary bile acids by intestinal
purge drastic purgative flora; desoxycholic acid, litocholic acid
Mastic Pistacia Masticin and mastichic acid
 Steroid Hormones
lentiscus
Kava/Kava-kava Piper Styrylpyrones – yangonin, o Glucocorticoids – carbohydrate metabolism; anti-
methysticum kawaiin, methysticin inflamatory; cortisone, cortisol
Cannabis/Indian Tops of Resin: Hashish o Mineralocorticoids – electrolyte and water balance;
Hemp/ Cannabis Constituets: THC, aldosterone
Marijuana/Pot sativa Cannabidiol, nabilone o Sex Hormones – Males: androgens, testosterone; Females:
Duquenois Test: violet on
chloroform layer
estrogen, progestin
RESIN COMBINATIONS:
 Oleoresins – volatile oils + resin X. ALKALOIDS
OLEORESINS SOURCE CONSTITUENTS  Bitter, basic nitrogenous compounds; physiologically active;
Turpentine/ Pinus palustris most of them ends in –ine;
Gum Turpentine
 Nitrogen can be: Primary amine – RNH2; Secondary amine –
Capsicum/ Capsicum frutescence Capsaicin –
Cayenne Pepper C. annum var longum vesicant; irritant R2NH; Tertiary amine – R3N
– African chilles (Louisiana long pepper)  All are solids except for: [CANS]
Ginger Zingiber officinale Zingebol and o Coniine – Coniium maculatum; poison hemlock (Socrates)
bisabolene – o Arecoline – scotchbroom (Cysticus coparius), lupin – Lupinus
stomachic;
mutabilis – anti-arrhythmic
antibacterial
White Pine Pinus strobus o Nicotine
Balsam of Copaifera spp. o Sparteine
Comaiba  Alkaloidal Reagents – form double salts with compounds of
 Oleo-Gum-Resin – volatile oil + gum + resin mercury, gold, platinum, and other heavy metals
o Myrrh/Gum Myrrh – Commipholra molmol; use: astringent o Wagnner’s Reagent – iodine in KI (red-brown)
(Astring-o-sol®) o Mayer’s Reagent – potassium mercuric iodide (cream)
o Asafetida – Devil’s dung; Ferula asafetida o Valser’s Reagent – mercuric iodide (white)
 Balsams – mixtures that contain cinnamic acid, benzoinc acid o Dragendorff’s Reagent – potassium bismuth iodide (orange)
or both or esters of these acids o Bouchdart’s Reagent – iodine in KI, most sensitive
BALSAM SOURCE o Marme’s Reagent – K cadmium iodide
Storax/Styrax – wound healing; Liquidambar o Sonnencheims’s Reagent – phosphotungstic acid
perfumery; storesin (α and β – Levant’s orientalis
o Hager’s Reagent – picric acid
storax 50:50); pharmaceutic and
compound benzoic tincture (benzoin, o Gold compounds
storax, tolu balsam, aloe, ethyl alcohol) o Tannic acid
Peru Balsam – parasiticide Myroxylon pereirae
Tolu Balsam – flavorant, expectorant; Myroxylon balsamum
compound benzoic tincture (benzoin,
A. PYRIDINE-PIPERIDINE ALKALOIDS
storax, tolu balsam, aloe, ethyl alcohol)  Nicotine – leaves of Nicotiana tabacum; use: CNS stimulant;
Benzoin – Sumatra; Siam  topical Styrax benzoin smoking deterrent (Nicoret®)
compound benzoin tincture  Areca, Areca Nut or Betel Nut – dried ripe seed of Areca
 Resin Acids – oxyacids (-COOH and phenik) catechu; arecoline – anthelminthic-taenicid; tannin content
 Glycoresin – resin + carbohydrate causes oropharengeal cancer; catechutannin  cancer
causing
IX. STEROIDS  Lobella – Indian tobacco; Lobella inflata; Lobeline – CNS
 Compounds with CPPP; metabolites of mevalonic pathways stimulant and smoking deterrent (Bantron®)
 Sterols
o Cholesterol – animals B. TROPANE ALKALOIDS (Solaneous alkaloids)
o Ergosterol – fungi  Belladona – Atropa belladonna; anticholinergic, mydriatic; (-)
o Phytosterol – plants hyoscyamine  atropine]
 Bile Acids  Hyocyamus or Henbane – leaves of Hyscyamus niger, 0.04%;
o Primary – directly from cholesterol (liver); cholic acid, hog +bean  toxic to swine
chenodeoxycholic acid  Egyptian Hyoscyamus or Egyptian Henbane – hyoscyamus
muticus, 1.5%
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 Duboisia – Duboisia myoporoides
 Withania – Withania somnifera; commercial sources of
atropine3
 Stramonium or Jimson Weed/Jamestown Weed – Datura
stramonium Solanaceae; Talumpunay; used for asthma and
COPD  burned then vapors are obtained
 Mandragora or European Mandrake/Satan’s Apple – roots of
Mandragora officinarum; mandragorine; potent poison
 Cocaine – Huanuco coca – Erythroxylon coca; Truxillo coca – E.
truxillense; crack/coke; psychomotor stimulant, local
anesthetic; Brompton’s cocktail
 Atropine – antispasmodic; antisialogogue; mydriatic and
cycloplegic; antidote for cholinesterase inhibitors; (+) inotropic
agent
 Scopolamine or Hyoscine – treatment form motion sickness;
Trans-scop® or Transderm®
C. QUINOLINE ALKALOIDS
 Cinchona – Red cinchona bark – Cinchona succirubra; Yellow
cinchona bark – C. calisaya; “cinchonism”; Quinine, Quinidine
– antimalarial; Thalleioquin test = fine blue fluorescence then
green ppt
 Cuprea – Remijia purdieana, Cupreaceae; commercial source
of quinidine
D. ISOQUINOLINE ALKALOIDS
 Ipecac – dried rhizome and rood of Cephaelis ipecacuanha;
constituent: emetine or methylcephaeline; use: ipecac syrup –
emetic
o Ipecac fluidextract is 14 times more potent
o Ipecac + Opium = Dover’s Powder (diaphoretic)
o Paregoric – camphorated opium tincture
o Laudanum – deodorized opium tincture
 Sanguinaria or Bloodrood – Sanguinaria Canadensis;
constituents: saguinarine; use: stimulating expectorant and
emetic
 Tubocurarine Chloride – aka curare or south American arrow
poison; Strychnos castelnaei; constituent: tubocurarine –
skeletal muscle relaxant
o Pot – clay
o Tube – bamboo
o Calabash – gourd
o Standardization of Tubocurarine – Head Drop Assay in
Rabbits – least amount of drug capable of producing muscle
relaxation so that head of animal drops in a characteristic
manner
 Opium or Gum Opium – unripe poppy seed capsules of
Papaver somniferum; only legal source is India; stone of
immortality; Marquis Test: opiods (purple); synthetic
o Diacetlymorphine – Heroin; acetylation of morphin;
increase danger of habit formation (very potent)
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o Hydromorphone – more potent analgesic; less frequent SE
o Apomorphine – condensation of morphine + HCl; use:
emetic
o Hydrocodone - antitussive
o Opiates – natural source
 Morphine – Serturner; most important, most abundant,
narcotig analgesic
 Codeine – P. Robiquet; most widely used opium alkaloid;
obtained from methylation of morphine; methymorphine
– antitussive
 Noscapine – non-narcotic opium alkaloid; antitussive;
anarcotin/narcotine
 Papeverine – smooth muscle relaxant, antitussive
 Thebane
E. INDOLE ALKALOIDS (Tryptophan)
 Rawolfia Serpentina – dried root of Raubolfia serpentina;
constituent: reserpine – treatment of snake bites to insanity,
hypotensive effects, sedative and tranquilizong properties
 Chichirica/Catharanthus/Vinca – Cantharanthus roseus;
constituents: vinscristine and vinblastine; lymph, hodgkins;
aka Periwinkle
 Nux Vomica – dried ripe seed Strychnos nux vomica; Strychnos
Ignatii (St. Ignatius Bean) – commercial source of strychnine;
constituents: strychnine (toxic central stimulant) 
Mandelin’s Test = violet; Brucine (alcohol denaturant)
 Physostigmine/Eserine – local sources: calabar, ordeal, or
Esere Bean; from Physostigma venenosum; treatment of
Glaucoma
 Ergot – dried sclerotium of Claviceps purpurea on rye, secale
cereal; constituents: ergonovine (ergometrine & metylsergide
– prophylaxis for migraine) – oxytoxic agent, ergotamine
o Lysergic Acid Diethylacmide – most active and most specific
psychomimetic drugs
F. IMIDIZOLE ALKALOIDS
 Pilocarpine – leaflets of Pilocarpus jaborandi; treatment of
glaucoma
G. STEROIDAL ALKALOIDS
 Green Hellebore/Veratum viride – roots of Veratrum viride;
use: cardiac depressant; (-) inotrope
 Black Hellebore – cardiac stimulant; (+) inotrope
 White Hellebore/European Hellebore – roots of Veratum
album; insectesies
© MANOR REVIEW CENTER NOTES (K.L)
H. ALKALOIDAL AMIDES
 Ephedra/Ma Huang – ephedrine; overground portion of
Ephedra sinica; nasal decongestant; bronchodilator
 Colchicine – Colchicum autumnale, Liliaceae; used in plant
genetics because it can double the chromosomes
 Khat/Abyssynian Tea – fresh leaces of Catha edulis;
constituents: cathinone  amphetiamine like effects
 Peyote/Mescal Buttons – aka “shrooms”dried tops of
Lophophora williamsii; hallucinogenic and euphoric agent;
constituent: mescaline (psilycybe  psilocybine)

I. PURINE ALKALOIDS/METHYLXANTHNES
 Cannot be precipitated by any alkaloidal reagents
 Caffeine – 1,3,7-trimethylxanthine *INSERT STRUCTURES*
o Kola, Cola or Kolanuts – dried cotyledon of Cola nitida
o Coffee Bean – dried seeds of Coffea Arabica
o Amaic Acid Test: Red-brown/transient purple
o C. robusta; C. liberica
 Chlorogenic acid + caffeine (+ caffeole) –(∆)
 Decaffenieted coffee – 0.08%
o Phosphodiesterase Inhibitors – diuresis; increase gastric
secretions; inhibit uterine contraction; weak (+)
chronotropic and inotropic effects
 Theophylline – 1,3-dimethylxanthine; leaf buds of Camellia
sinensis; treatment of bronchial asthma; tocolytic agent
o Aminophylline – semi-synthetic theophylline derivative –
treatment of bronchial asthma
 Green Tea (Fresh) – China and Japan
 Black Tea (Fermented) – India and Sri Lanka (Ceylon)
 Theobromine – 3,7-dimethylxanthine; seeds of Theobroma
cacao; diuretic in cardiac and pulmonary edema

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