MODULE 2 │ PHARMBIOSCI 4

PHARMACOGNOSY
PHARMACOGNOSY • Marc
• Undissolved portion of the drug that remarks after extraction
• Applied science that deals with the biological, biochemical, process is completed
and economic features of drugs of biological origin and their
constituents METHODS OF EXTRACTION
• Medicinal products in their crude or unprepared form
1. Infusion
HISTORY OF PHARMACOGNOSY • Hot water (ex. tea); short contact of action

Babylonians 2. Maceration
• Laws of Hammurabi (772 BC) • Soaked in solvent for long period of time
• clay models of human body
• medicinal effects of 250 plants 3. Percolation
• mages and physician • Passage through percolator (ex. Simple Syrup USP)
• wheat and barley
4. Digestion
Ayurveda (2500 BC) • < 35-40°C
• Traditional medicine
• “Science of life” 5. Decoction
• Mother of all healing arts • Boiling water
• Charaka samhita
• text on internal medicine 6. Liquid-Liquid Extraction - Partitioning
• Etiology, symptoms, and therapeutics
• Sushruta sambita 7. Distillation
• 184 chapters; 1120 illness
• Surgeries and instruments Indigenous Plants
• Plants growing in their native countries (ex. Rinorea
Egyptians (Ebers papyrus – 1150 BC) niccolifera – metal eating plant; more on nickel)
• Embalming
• George Ebers Naturalized Plants
• priest and doctors • Plants grow in foreign land other than their native homes
• human anatomy and use of plants
PREPARATION OF CRUDE DRUGS
Greeks
• Dioscorides (78 AD) 1. Collection
• wrote “De Materia Medica” or The Medicinal material; • Small scale
• aloe, belladonna, colchicum, ergot, opium; 600 • Ensuring the true natural source of the drug: improper
plants collection, collection time
• Claudius Galen (131-200 AD) I. highest content
• described methods and processes of preparing
formulas containing plant and animal drug 2. Harvesting
• FATHER OF PHARMACEUTICAL COMPOUNDING • Specific or proper season
• manual labor vs. mechanical devices
Germans
• C.A. Seydler (1815) 3. Drying
• coined the term, “pharmacognosy” from “pharmakon” • Remove moisture to prevent bacterial and fungal growth with
and “gnosis” in Analecta Pharmacognistica enzymatic degradation
• JA Schmidt (1811) • fixed constituents, facilitates grinding and milling, converts
• used the word, “pharmacognosy”; Lehr Buch de Materia plants to convenient form
Medica; described study of medicinal plants and their • Natural or Artificial
properties
• Friedrich August Fluckiger 4. Curing
• simultaneous application of various scientific • Special drying process that enhances properties of plant’s
• disciplines with the object of acquiring drugs from every active ingredients
point of view • Ex. Cascara in MgO or Vanilla under the “sweating” process
• Pelletier and Caventou
• Quinine 5. Garbling
• Friedrich Serturner • Final step in preparation of crude drugs
• Morphine • removal of extraneous matter

Crude Drugs Last Packaging, Storage, Preservation

• Vegetable or animal drugs consists of natural substances • Protection and marketability
that had undergone only the processes of collection and • maintain high degree of quality of drug
drying
• Plant exudates EVALUATION OF CRUDE DRUGS

Natural Substances • Determine quality and purity; qualitative (intrinsic value of

• Formed in nature drug; type of medicinal principles) and quantitative (amount)
• Whole plants or parts; Animals or organs
• No molecular modifications had been made Organoleptic Evaluation
• Organ of senses
Derivatives or extracts • evaluates macroscopic appearance of drug
• Chief principle or constituents of crudes drugs that are
separated and used in a specific manner
• Menstruum
• Solvent; liquid/ liquid, mixture used to extract active principle

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Microscopic Environment
• Allows a more detailed examination of a drug and it can be • Soil
used to identify organized drugs by their known histological • Climates
characters • Associated flora
• adulterants • Methods of cultivation
• Evaluate in a cellular level
I. CARBOHYDRATES
Physical Evaluation
• Determination of various physical characteristics/ parameters • Polyhydric aldehyde or ketone alcohols that contain C, H,
• Solubility, sp. gv., viscosity of drugs, optical rotation, and O
congealing point, melting point, boiling point, etc. • H and O has same ratio as that of water, thus named
CARBO + HYDRATES
Chemical Evaluation • First product of synthesis [Cn (H2O) n]
• Assay of active constituents using chemicals (titration) • Xylem – H2O
• Best determination of official potency • Phloem – nutrients – food (∆ source; ∆ storage; structure)

Pharmacologic Evaluation A. CLASSIFICATION OF CARBOHYDRATES

• Bioassays
• Assays using animals or excised organs to evaluate I. MONOSACCHARIDES
effects of drugs • simplest carbohydrate unit
• cannot be hydrolyzed
CLASSIFICATION OF DRUGS • (+) Benedicts and Barfoed’s = brick red ppt.
• Classified according to:
1. Alphabetical • # Of carbon atoms in its backbone
• Arranged in alphabetical order based on Latin or English • Functional groups
name or even vernacular names • Neuraminic – aka sialic
# of Carbon NAME EXAMPLE
2. Morphological Atoms
• Forms 2 Diose hydroxyacetaldehyde
• Grouped according to plant part used 3 Triose dihydroxyacetone and
• Convenient but no chemical correlation glyceraldehyde
4 Tetrose erythrose
5 Pentose arabinose, xylose and ribose
3. Taxonomic (Lireus)
6 Hexoses glucose, fructose galactose
• evolutionary development; no correlation on chemical and 7 Peptose dedoheptose
biological activity 8 Octulose D-glycerol-Dmannoctulose
• Phylogeny 9 Nonose Neuraminic acid
• natural relationship that occurs among plants and
animals PENTOSES
4. Therapeutic/ Pharmacologic Xylose
• based on drugs effect on body • “Wood sugar”
• obtained from boiling corn cobs, straw
5. Chemical • diagnostic aid for intestinal malabsorption
• Based-active constituents that are present • absorbed but not metabolized
• Preferred method of classification • Xylan → Xylose (aldehyde) → xylulose (ketoses)
• Phytochemical studies but ambiguous at times
HEXOSES
ACTIVE CONSTITUENTS • most important monosaccharide
• considered secondary metabolites Glucose
• through drug biosynthesis or biogenesis • Aldohexose
• Classes: • aka Dextrose, Blood Sugar, Grape Sugar, Physiologic Sugar
• Pharmacologically active • aldehyde group is present in C1
• Pharmaceutically active • reducing sugar as determined by Benedict’s Test
• occurs as linear and cyclic
BIOSYNTHETIC PATHWAY • β-D-Glucose – most abundant and important
• 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
• aka Levulose, Fruit sugar (sweetest monosaccharide)
• (+) Seliwanoff’s Test: pink/red
BIOGENESIS • ketone group is present in C2
• reducing sugar
Ontogeny or Stage of Development • fruit sugar; sweet fruits and honey
• Ex. Cannabis sativa • obtained from inversion of aq. sucrose solution
• cannabidiol – plant is young • honey (mostly sucrose)
• cannabinol – mature plant • High Fructose Sweeteners – isomerization of glucose
isomers from Streptomyces sp.
Heredity or Genetic • Uses:
• Japanese Peppermint and Peppermint • Food for diabetic
• Qualitative and Quantitative changes • Ingredient in infant feeding formula
• Ingredient in Fructose injection nutrient

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Galactose • Scheele – lemon juice (1784)
• Aldohexose • citric – Tricarboxylic acid (TCA) – (Deniges Test)->
• “Brain Sugar” tartaric (by product, dicarboxylic) = wine
• C4 epimer of glucose (C2– mannose) • Lactic Acid
• milk: lactose: neuronal fibers: galactosidase • acidulant – infant feeding formula, feminine wash
• Galactosemia (0.2% chlorhexidine – vaginal 0.6% - mouth) –
• Gaucher’s Disease (B-Glucocerebrosidase) (INSERT)
• (+) Mucic acid and Phenyl hydralazine = crystal
formation (osazone crystals) Alcohol/Ethanol
• 95% ethanol by volume 15.56°C
II. DISACCHARIDES • product of fermentation
• composed of two monosaccharide units • undergo process of distillation to concentration the alcohol
• formed via dehydration synthesis; glycosidic bond content to 40-55%
• low conc. – CNS stimulant
Sucrose • high conc. – CNS depressant
• “Table sugar” • Brandy – wine
• obtained from: • Whiskey – malted grain
• Saccharum officianarum (sugar cane) • Rhum – molasses
• (+) lime = decreased albumin • Diluted Alcohol – 48.4-49.5% ethanol at 15.56%°C
• use SO2 → clear = clarification
• Beta vulgaris (sugar beets) PRODUCTS OF REDUCTIVE METABOLISM
• cossettes (“cut limps livers” – chop finely)
• Acer saccharum (sugar maple) Mannitol
• non-reducing sugar: (-) Benedict’s Test • from manna, dried exudate of Franxinus ornus
• glucose + fructose, α-1,2 bond • osmotic diuretic and osmotic laxative, GFR
• uses: demulcent, sweetening agent to mask taste, • used in people with neurological trauma
coating agent, preservative (85%), production of syrups,
retards oxidations Sorbitol
• Uses: • from berries of mountain ash, Sorbus aucuparia
• Demulcent • aka D-glucitol; tastes ½ sweet as sugar
• Sweetening agent; masks taste • used in manufacture of toothpaste and chewing gum →
• Coating agent xylitol as alternative
• Preservative, syrups
III. POLYSACCHARIDES
Molasses
• residual dark colored syrup after complete crystallization of Homoglycans
sucrose • polysaccharides that yield one type of monosaccharide unit
• only disaccharide in free state upon hydrolysis
• food and ethanol industry • Starch – temporary storage form of photosynthetic products
from:
Maltose • Zea mays – corn
• malt sugar • Triticum aestivum – wheat
• produced-germination of barley • Solanum tuberosum – potato
• glucose + glucose, α-1,4 bond • Oryza sativa – rice
• major degradation product of starch • Maranta arundinacea – arrowroot
• reducing sugar (beer, Ovaltine, cereal drinks) • Constituents:
• glu + glu + glu = maltotriose (oligosaccharide – 3-10C) Bases of Amylose Amylopectin
Differences
Lactose
Structure Linear/Helical 250-300 Branched
• milk sugar (cow’s milk)
units α-1,4 (Every 25-30 mins) 1000
• glucose + galactose, β-1,4 bond or more α-1,4 and α-1,6
• reducing sugar
• milk products:
1. Whole milk –(sit)→ butter
Solubility in Insoluble Soluble
2. Butter milk –(churn)→ cream water
3. Skimmed milk→ whey
• (Rennin – young calf) → coagulum –(tx)→ cheese Iodine test Deep/Dark blue Blue violet/purple
• Kamyss – fermented spoiled milk
• Condensed Milk – partial condense autoclave, Enzymes that break down starches:
evapo
Alpha amylase
Lactulose
• present in pancreatic juice and saliva
• fructose + galactose, β-1,4 bond
• *metabolism/breakdown of carbohydrates starts in mouth
• alkaline rearrangement of lactose
• converted by lactose to lactic and acetic acid, which causes
Beta amylase
irritation of the intestines and subsequent catharsis – ideally
• hydrolyses starch to nearly pure maltose
used with MI and stroke
Uses: tablet filler, binder and disintegrant; antidote for
PRODUCTS OF OXIDATIVE METABOLISM
iodine poisoning
Cherry Juice
Starch Preparations:
• ripe fruit of Prunus cerasus (Rosaceae)
• contains pectin and 1% malic acid
• cherry syrup 1. Pregelatinized starch
• chemically or mechanically processed to rupture all or part of
granules; tablet binder
Plant Acids
• uses: acidulants in effervescent formulations 2. Sodium starch glycollate
• component of buffer systems • disintegrating agent
• Citric Acid

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3. Hetastarch PLANT EXUDATES BOTANICAL SOURCE
• >90-99% amylopectin; plasma expander Acacia Gum Arabic → arabin → K, Ca, Mg, Acacia Senegal
• Hydroxyethyl starch Arabic acid
• Voluben® Mucilage
Emulsifier
4. Glutens Suspending agent (33-35%)
12% H2O content
• tacky proteins that impede flow of starch
<60% alcohol
Tragacanth Astragalus gummifer
Glycogen Types:
• storage polysaccharide in animals vermiform (worm)
• more branched than starch (every 10) tragacanth sorts (tear)
• red color with iodine Constituents:
Inulin Bassorin (swells: 2/3);
• polyfructan of fructofuranose traganthin (dissolves: 1/3)
SA: 5-6%
• Chicorium intybus (Asteraceae) – chicory root K: galactomannan → bulk laxative
• improve digestion Karaya – most fetid gum Sterculia gum Sterculia urens
• Uses: ingredient in culture media
• evaluation of renal function Indian – Ghatti; alternative from acacia Anogeissus latifolia

Dextran MARINE GUMS

• glucosan GUM SOURCE CONSTITUENTS
• Leuconostoc mesenteroides
Agar or Algae
• plasma expander Japanese Gelidium cartilagineum Agarose
Isinglass Gracilaria confervoides Agaropectin
Cellulose
• structural polysaccharide in plants (from the hair of seeds of Algin Brown Seaweeds Mannuronic acid
Gossypium hirsutum) Macrocystis pyrifera
• Purified/Absorbent Cotton Carrageenan Red Algae Kappa-gelling
• surgical dressing or Irish Moss Chondrus crispus component
• Soluble Guncotton/Pyroxylin Gigartina mamillosa Iota-gelling component
Lambda – non-gelling
• formed by action of nitric and sulfuric acid on
component
cotton
• Other ingredients: castor oil (flexibility) Danish Agar Furcellaria fastigiata Kappa
• camphor (water-proof)
• Use: topical protectant
• Other Cellulose Derivatives SEED GUMS
• cellulose acetate phthalate (CAP) – coating GUM SOURCE
agent Psyllium Seed coat of:
• methylcellulose and methylcellulose – artificial Plantago psyllium – Spanish
tears Plantago ovata – Blonde

Chitin Cydonium/Quince Seed Ripe seed of Cydonia vulgaris

• structural polysaccharides in animals Guar Gum or Guaran Endosperm of Cyamopsis
• exoskeleton: mollusks and arthropods tetragonolobus
• homoglycan of N-acetylglucosamine
• Chitosan Locust Bean Gum/Carob Pulp Endosperm of the seed of
or St. John’s Bread Ceratonia siliqua
• deacetylation of chitin
• water purification
• Glucosamine MICROBIAL GUM
• acid deacetylation and hydrolysis of chitin GUM SOURCE NOTES
Xanthan Action of Has a pseudoplastic activity
Heteroglycans
Gum Xanthomonas enable toothpastes and
• polysaccharides that yield more than one types of campestris on ointments to spread easily
monosaccharide units upon hydrolysis carbohydrates

B. GUMS AND MUCILAGES

C. PLANT EXTRACTIVES
• natural plant hydrocolloids that may be classified as anionic
or non-ionic polysaccharides Pectin
• produced by plants as a protective after injury; upon • intracellular cementing materials; partially methoxylated
• hydrolysis, they yield arabinose, galactose, glucose, galacturonic acid (swelling); extract of inner portion of rind of
mannose, xylose and other uronic acid derivatives citrus fruits (pomelo, grapefruit, orange, ponkan, lemon,
• Pb acetate and alcohol calamansi, dalanghita, apple) and apple pomace;
antidiarrheal agent;
LINEAR BRANCHED • Kaopectate – Kaolin + Pectin -> antidiarrheal
preparation
Solubility Less More
• Protopectin – unripe
Stability Less More • Pectin (sol) – just ripe
Use Viscosity enhancers Gelating agents • Pectic acid – overripe

D. GLYCOSIDES
GUMS MUCILAGES
Production Pathologic (injury) Physiologic (natural) • Heteroglycans; “sugar ethers”; BETA form occurs in plants;
Solubility in Readily soluble Slimy mass N-, S-, C-, O, alpha or beta; regulatory, protective and
water sanitary compounds
• Components:
• glycone (acts as vehicle; inactive)
• aglycone (genin; basis for classification; active)

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 CARDIAC GLYCOSIDES Dioscorea or Yam
• Dioscorea spiculiflora – contains diosgenin which is a
• Unsaturated steroidal aglycone tests glucocorticoid precursor
• Libermann-Burchard = blue/green; yellow for saturated • Dioscorea floribunda – best source of steroids
• Salkowski = red/violet • Diosgenin – anti-inflammatory
• 2-deoxy sugar glycone test
• Keller-Killanii test = reddish brown) Ginseng
CARDENOLIDES BUFADIENOLIDES • Panax ginseng (Asia)
Common (active) Rare (Bufo sp); (inactive) • Panax quinquefolius (American)
C-23 α and β unsaturated C-24 doubly unsaturated • aphrodisiac and an adaptogen
5membered lactone ring 6membered lactone ring • Constituents: panaxosides, ginsenosides, chikusetsusaponin

CYANOPHOIC OR CYANOGENIC GLYCOSIDES

• Digoxin – H2O
• Digitoxin – lipid • Amygdalin (H2O and amygdalase) → mandelonitrile glucose
• Desllanatoside – digitalization = rapid (H2O and prunase) → mandelonitrile + glucose →
• Convallaria – Convallatoxin – Lily of the Valley benzaldehyde + HCN
• Apocynum – Dogbane – cymarine • Rosaceae
• Adonis – Pheasant’s Eye – adonitoxin • Emulsin – amygdalase and prunase (collectively)
• Black Hellebore – Xmas Rose – hellebrin • APE = A+P+E
• Strophantus – K strophantin (good) G strophantin (bad) – • Grignard’s Test = brick red/red coloration
(toxic)- Oubain
• Sqiuill – Scillarenin -→ expectorant (bufadienolides) Bitter almond
• Prunus amygdalus
ANTHRAQUINONE GLYCOSIDES • source of Laetrile (Vit B17) – controversial treatment for
sickle cell anemia
• Aglycone: Anthracene
• Use: cathartic (drastic) Wild cherry
• Derivative color: orange • Prunus serotina
• Identification Test: Borntranger’s Test • flavored vehicle, expectorant and sedative

Cascara Sagrada – Rhamnus purshianus Apricots

• Constituents: • Prunus armeniaca
• Cascarosides A and B – optical isomers of barbaloin
• Cascarosides C and D – optical isomers of chrysaloin ISOTHIOCYANATE GLYCOSIDES
• LANE’s Pill – casanthol, purified mix of anthranol glycosides
• Cured in MgO for 1 year Rapeseed
• Brassicca napus
Frangula or Buckthorn Bark – Rhamnus frangula • gluconapin
• Present in Movicol® – Karaya (laxative) + Frangula
(cathartics); for constipation Watercress
• Nastutium officinale
Aloe • Gluconasturtiin
• dried latex or juice of Aloe barbadensis or Aloe vera • Odor test → mustard smell (volatile); garlic (allicin)
(Curacao aloe); hybrids of Aloe ferox with Aloe Africana and • Ferric chloride test → blood red (non-volatile)
Aloe spicata (Cape aloe); (cathartics and burns)
• Constituents: barbaloins and aloe emodin Black Mustart or Sinapis Nigra
• Brassica nigra – sinigrin
Rhubarb – glucohein • Sinigrin/sinalbin –(myrosinase) → allyl/acrinyl
Rheum or Chinese Rhubarb Indian Rhubarb or Himalayan
(Therapeutic) Rhubarb (Ornamental) White Mustard
• Brassica alba – sinalbin
Rheum officinale Rheum emodi
Rheum palmatum Rheum webbianum FLAVONOL GLYCOSIDES

Senna • flavonoids or bioflavonoids from citrus fruits and soya

• dried leaflet of Cassia acutifolia (Alexandria), Cassia
angustifolia (Tinnevelly) Rutin and Hesperidin
• cultivated in wat lands resembling rice paddies • vitamin P or permeability factors
• Derivative color: blue green • treatment of capillary bleeding secondary to capillary fragility
• Constituents: Sennosides A, B, C, and D
Hesperitin, Diosmin, and Naringen
Chrysarobin • treatment of symptoms of common colds
• from Goa powder, Andira araroba
• only anthraquinone glycoside that is NOT used as cathartic Yellow Pigment
because it is very irritating • rutin and quercetin
• used as keratolytic; hot benzene is used to extract this
substance Milk Thistle
• Silybum marianum
SAPONINS • silibinin, silymarin, hepatoprotective

• foam upon shaken (froth test) Gingko

• bitter, acrid taste • Ginggko biloba
• sternutatory (may irritate mucous membrane = sneezing) • gingkolides, bilolabides
• destroy RBCs of cold • memory enhancement

Glycyrrhiza or Licorice
• dried roots of Glycyrrhiza glabra
• increase foaminess of beer
• Constituents: glycyrrhiza, glycyrrhiziac acid

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 ALCOHOL GLYCOSIDES i. Hydrolysable
• Readily hydrolyzed to yield phenolic acids and sugars
• Salicin – salix and populous • Pyrogallol
• Leather: bloom
Salix purpurea and Salix fragilis • FeCl3 = blue-black
• Aglycone: saligenin • Br2 test = (-)
• Anti-inflammatory; anti-rheumatic
• Tests: ii. Non-hydrolysable
• Fehling’s – brick red • (aka Condensed Tannins/ Phlobatannins) – results from
• Nessler’s – gray condensation of catechin and leucocyanidin
• Tollen’s – silver mirror • tend to polymerize → phlobaphene (red colored product)
• Schiff’s – decolorization • Leather: tanners red
• FeCl3 = green-black
ALDEHYDE GLYCOSIDES • Br2 test = (+)

Vanilla B. PSEUDO TANNIN

• cured fruit of Vanilla planifolia (orchidaceae) – Mexican, Vera
Cruz, Bourbon Hamamelis Leaf
• Constituent: vanillin • Witch Hazel Leaf, dried leaf of Hamamelis viriniana
• Use: flavoring agents • constituent: hamamelitanin
• used for hemorrhoids
PHENOL GLYCOSIDES
Nutgall
Urva ursi • excrescence obtained from young twigs of Quercus
• dried leaf of Arctostaphylos urva ursi infectoria, Fagacea (when Cynips tinctoria bores a hole to
• Constituents: arbutin (hydroquinone + sugar) deposit ova)
• Use: astringent and diuretic • constituent: tannic acid (Gallic + Ellagic = Tannic [GET]) →
astringent
Poison Ivy (Rhus radicans) and Poison Oak (Rhus
toxicondendron) Chinese/Japanese Gall
• uroshiol – delayed contact dermatitis (type IV) • Rhus chinensis
• Aphis sp. – gallic acid (Bismuth subgallate – protectant;
LACTONE GLYCOSIDES deodorizer for flatulence)

Coumarin III. LIPIDS

• from Tonka beans, Dipteryx odorata
• constituents: dicoumarol bishydroxycoumarin → FIXED OILS FATS WAXES
anticoagulant, Warfarin Long chain fatty acids + Long chain fatty acids Long chain fatty acids
• Test for unsaturated lactone: Kedde’s = blue-violet glycerol + glycerol + high molecular
weight alcohol (cetyl
Cantharides From vegetables From animals alcohol, stearyl
• from dried insect, Cantharis vesicatoria; Russian/Spanish fly; Liquid at room temp Sold at room temp alcohol)
EXCEPTIONS: Liquid
Blistering fly
EXCEPTIONS: EXCEPTIONS: Liquid W: Jojoba
• Constituents: cantharidin-irritant, vesicant and rubefacient Solid FO – Theobroma, F: Cod liver oil
• Causes priaprism – sustained erection Myristica oil

Psoralens USE: storage USE: storage USE: protectant

• photosensitizing furocoumarins
• from Bishop’s flower, Ammi majus Fatty Acids
• Methoxsalen – repigmentation in vitiligo • Saturated – capric, lauric, myristic, palmitic, stearic,
• Trioxsalen arachidic
• Unsaturated (=) – palmitoleic, oleic, linoleic, linolenic,
II. TANNINS arachidonic
• Complex substances or polypeptides that are difficult to USP Tests:
separate because they do not crystallize • Acid value or Acid number
• Phenolic in nature • mg of KOH needed to neutralize free FAs
• non-crystallizable polyphenols • Saponification value
• protein precipitant (astringent) • mg of KOH needed to saponify the esters
• found in barks and leaves • Iodine value
• Local sources: • g of iodine absorbed in 100g of sample
• Guava – Psidium guajava
• Kamachile – Pithecolobium dulce Expression
• Duhat – Syzigium cumini • cold-pressed oil
• Characteristics: • hot-pressed oil
• Acidic • only from fixed oils
• Sharp puckering taste
• Causes precipitation of alkaloids Rendering
• Industrial – leather and ink • fats
• Clinical – astringents – GI or skin, treatment of burns
• Chemical classes: (True tannins vs Pseudo tannins – Solvent extraction
chlorogenic acid and catechins) • fats
• hexane – best solvent for extracting fats
A. TRUE TANNIN
Types of oils
• animal skin → leather • ability to absorb oxygen
• (+) Gold Beater’s Skin Test • oxygen saturates double bonds forming oxides that
polymerize to form films
• paint industry

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 IODINE VALUE RANGE EXAMPLES V. FATS AND RELATED COMPOUNDS
Non-drying <100 Olive
Almond Theobroma Oil
Semi-drying 100-120 Cottonseed • Theobroma cocao
Sesame • food for the gods
Drying >120 Linseed
• Uses:
Cod liver oil
• cocoa syrup – beverage
• cocoa butter – suppository base (melts at 30-35°C)
Reactions of Lipids
• Nibs → prepared cacao/breakfast cacao
Hydrogenation Lanolin
• liquid oil to semi-solid fat • purified fatlike substance from wool of sheep Ovis aries,
• passing of H with Pd/Ni in 160-200°C Boviidae
• shortening and cooking fat • contains 25% water;
• Uses:
Sulfation • water absorbable ointment base
• reaction with sulfuric acid • emollient
• temp at chilling • Anhydrous lanolin – wool fat (contains 0.25% water)
• sulfates add to double bonds, surfactants
Cod Liver Oil
IV. FIXED OILS • from Gadus morrhua
• sclerosing agent to obliterate varicose veins
Seed Oils • source of vitamin A and D (Scott’s emulsion)
FIXED OIL BOTANICAL SOURCE
Cottonseed Oil Gossypium hirsutum Undecylenic Acid
- IM injection • pyrolysis of ricinoleic acid from castor oil
- not edible • has antifungal property
- constituent: gossypol –x-> male
sterility
- ID test: Halphen/Bevan Azelaic Acid
Sesame Seed Oil Sesmum indicum • onolysis of Castor oil
- Benne/Teel Oil • anti-acne
- uses: IM injection, edible
- constituent: sesamol (phenol) – self- VI. WAXES
preserving + lignin sesamolin &
pyrethrin insecticides Spremaceti
- ID test: Baudouin
• head of spermwhale, Physeter macrocephalus
Coconut Oil Cocos nucifera
- constituents: lauric, myristic,
• synthetic spermaceti – cetyl ester wax
triglycerides
Castor Oil Ricinus communis Jojoba Oil
- tangan-tangan • seeds of Simmondsia chinensis, Buxaceae
- ricinoleic (good) - cathartic trcinoleic • hydrogenated form resembles spermaceti
(good) ricin (toxic) = abrin (jequirity • eicosenoic acids: eicosenol and docosenol
bean)
Peanut Oil Arachis hypogaea Beeswas or Yellow Wax
- peanut oil cake, peanut butter • honeycomb of bees, Apis mellifera
- aflatoxin aspergillus (due to • stiffening agent in plasters and cerates
improper storage and drying) • White Wax – bleached yellow wax; myricyl pamitate
Soybean Oil Glycine soja
- stigmasterol – steroid Carnuba Wax
- lecithin – regulate cholesterol
- antilipemic agents
• leaves of Copernicia prunifera
• myricyl cerotate
Corn Oil Zea mays
- germ oil cake – IM injection
- antilipemic agents VII. VOLATILE OILS
- Hydrogenated volatile oils = sergers
Safflower Oil Carthamus tinctoria • Odorous principle in carious plants
- antilipemic agents • Colorless and photosensitive; light resistant tight container in
Sunflower Oil Helianthus anuus a cool and dry place
- antilipemic agents • Undergoes auto-oxidation and resinification
Ethiodized Oil Injection Iodine addition product • Plant families:
of ethyl ester of fatty • Glandular hairs or trichomes (lamiaceae → labiatae)
acid of Poppy seed
• Modified parenchymal cells → piperaceae
• Oil tubes or vittae → apiaceae (umbelliferae)
• Lysigenous and schizogenous passages → pinaceae
and rutaceae
Pericarp Oils • Physical characteristics:
FIXED OIL BOTANICAL NOTES • Possess characteristic odors, high refractive index,
SOURCE
optically active, immiscible in H2O but can be sufficiently
Olive Oil Olea Grades:
- ID test: europaea First Grade Virgin Olive Oil
be soluble to impart odor in water → aromatic water
Milon’s – extracted with less pressure VOLATILE OILS FIXED OILS
Second Grade Virgin Olive Oil – Distillation Saponification Rancidity
pulp in #1 is extracted with more Resinification (+) Grease Spot
pressure (-) Grease Spot
Technical Oil
– extracted with hot water
Sulfur Grade Methods of Obtaining Volatile Oils
– extracted with Carbon disulfide
inferior quality
Distillation
Tournant Oil
– fallen and decomposing fruits • Water Distillation – dry sample; turpentine oil
• Water and Steam Distillation – dry sample; clove and
cinnamon oil
• Steam Distillation - peppermint and spearmint
Module 2 – Pharmacognosy Page 7 of 11 RJAV 2022
 • Destructive Distillation – empyreumatic oils (heat without 4. Hamamelis Oil
access of air); pinaceae and cuppressiaceae – only family to • Hamamelis virginiana
use destructive distillation (“char”) • 2-hexanal
• hemorrhodal preparation
Enzymatic Actions – mustards
• Ketone Volatile Oil
Expressions 1. Camphor
• Ecuellle and Piquer – rolling a fruit in a trough line with • Cinnamomum camphora
sharp tiny projections enough to puncture the rind – citrus • natural camphor: (+)
fruit • synthetic camphor: racemic (-)
• Enfleurage – flower petals (or small plant part) on a fatty • anti pruritic, rubefacient, anti-infective
pomade followed by EtOH extraction 2. Spearmint
• Mentha spicata; carvone (-)
Components of Volatile Oil • (+) carvone – same odor as caraway (Carum
carvi)
STEREOPTENE ELEOPLENESES 3. Buchu Oil
Solid oxidized hydrocarbon portion Liquid hydrocarbon portion
• Berosma betulina
Menthol Methysalicylate • Diosphenol
Amenthol Encalyptol • menstrual problem, carminative, anti-rheumatic
Thymol Eugenol 4. Wormwood/ Quinghaosu
• Artemia annu
Medicinal and commercial use: fabrication of perfumes • Artemisia ketone and camphor
• Top Notes – (smell – minute to hour) • anti-malarial → artemisinin, artemether, artesunate
• most volatile product
• leave skin readily – lemon (limonene – most used • Phenol Volatile Oil
flavorant), lavender, anise oil 1. Clove Oil
• Middle Notes – (3-6 hours) • Engenia caryophyllus
• intermediate tenacity and volatility – thyme, neroli and • Eugenol
rose oil • toothache drops, dental analgesic
• Base Notes – (long hours) 2. Thyme
• low volatility and high tenacity • Thymus vulgaris
• aka Fixatives = staying power • thymol → antifungal and antibacterial
3. Creosol Oil
Musk - dried secretion from the preputial follicles of the male musk • Fagus grandifloras
deer of Asia, Moschus spp – muskane • creosole → disinfectant, guiacol
4. Jupiter Tar
Civet - glandular secretion appearing in an outwardly discharging • Juniperus oxycedrus
pockets of civet cat, Paracloxutus hermaphrodites • Cadinene
• Anti-eczema → Polytar®
Amber gris - most valuable material; pathologic product formed in
stomach of sperm whale when if feeds on squid or cuttlefish • Phenolic Ether Volatile Oil
(ambrein) 1. Nutmeg/ Myristica Oil
• Myristica fragrans
Constituents of Volatile Oils: • constituents: safrole and myristicin
• halloahogen
Terpenes 2. Anise Pimpenella
• natural products whose structure are made up of isoprene • Pimpenella anisum –anisaldehyde, trans anethol
units: 3. Fennel
• Freniculum vulgare
Monoterpene – 2 • fendiole, trans anethole

• Hydrocarbon Volatile Oils • Sesquiterpene - 3

1. Turpentine Oil • Diterpene - 4
• Pinus palustris • Triterpene - 6
• rectified turpentine • Tetraterpene – 8
• terpinhydrate/ terpinol – expectorant • Acetate-Mevalonate Pathways
• α and β → pinene • Shikimic Pathway – aromatic compound
• ** turpentine oil + NaOH = rectified turpentine
• ** RT + HNO3 = terpinhydrate/ terpinol VIII. RESIN AND RESIN COMBINATION
2. Peppermint Oil
• Mentha piperita Resins
• menthol (antipruritic) → (+) synthetic, (-) natural • amorphous products with complex chemical nature; hard
• Japanese Peppermint Oil – Mentha arvensis transparent or translucent and when heated they soften and
• increase menthol concentration melt; complex mixtures of:
• flavorant, carminative, stimulant counter – irritant • Resin acids
• Resin alcohols
• Aldehyde Volatile Oil • Resinotannols
1. Cinnamon Oil • Esters
• Cinnamomum loureiril, Cinnamomum zeylanicum, • Resenes – B-complex neutral substances devoid of
Cinnamomum cassia (aka cassia oil) characteristics
• constituent: cinnamaldehyde RESIN SOURCE CONSTITUENTS/NOTES
• uses: flavoring, carminative, antiseptic Rosin/Colophony Pinus palustris
2. Lemon Peel Oil
Podophyllum Podophyllum Podophyllin
• rind of the fruit Citrus limon peltatum –caustic agent for warts
• lemon oil Peltatin
• citral and limonene – purgative
3. Citronella Oil Podophyllotoxin
• leaves of Cymbopogon winterianus – tanglad – etoposide, tenoposide
• citronellal
• insect repellant

Module 2 – Pharmacognosy Page 8 of 11 RJAV 2022

 Eriodictyon/Yerba Eriodictyon Bile Acids
Santa californicum • Primary
• directly from cholesterol (liver)
Jalap Exogonium Jalapin and purganol
purge – drastic purgative • cholic acid, chenodeoxycholic acid
• Secondary
Mastic Pistacia lentiscus Masticin and mastichic acid • fermentation of primary bile acids by intestinal flora
• deoxycholic acid, lithocholic acid
Kava/Kava-kava Piper Styrylpyrones
methysticum – yangonin, kawaiin, Steroid Hormones
methysticin • Glucocorticoids
Cannabis/Indian Tops of Resin: Hashish • carbohydrate metabolism
Hemp/ Cannabis sativa Constituets: THC, • anti-inflammatory; cortisone, cortisol
Marijuana/Pot Cannabidiol, nabilone • Mineralocorticoids
Duquenois Test: violet on • electrolyte and water balance
chloroform layer
• aldosterone
• Sex Hormones
• Males: androgens, testosterone
Resin Combinations • Females: estrogen, progestin

Oleoresins – volatile oils + resin X. ALKALOIDS

OLEORESINS SOURCE CONSTITUENTS
Turpentine/ Pinus palustris • Bitter, basic nitrogenous compounds; physiologically active;
Gum Turpentine most of them ends in –ine
• Nitrogen can be:
Capsicum/ Capsicum frutescence Capsaicin
Cayenne Pepper C. annum var longum – vesicant;
• Primary amine – RNH2
– African chilles (Louisiana long pepper) irritant • Secondary amine –R2NH
• Tertiary amine – R3N
Ginger Zingiber officinale Zingebol and • All are solids except for: [CANS]
bisabolene • Coniine – Coniium maculatum; poison hemlock
– stomachic; (Socrates)
antibacterial • Arecoline – scotchbroom (Cysticus coparius), lupin –
Lupinus mutabilis – anti-arrhythmic
White Pine Pinus strobus
• Nicotine
Balsam of Comaiba Copaifera spp. • Sparteine

Alkaloidal Reagents – form double salts with compounds of

Oleo-Gum-Resin – volatile oil + gum + resin mercury, gold, platinum, and other heavy metals
• Myrrh/ Gum Myrrh
• Commipholra molmol • Wagnner’s Reagent – iodine in KI (red-brown)
• use: astringent (Astring-o-sol®) • Mayer’s Reagent – potassium mercuric iodide (cream)
• Asafetida • Valser’s Reagent – mercuric iodide (white)
• Devil’s dung • Dragendorff’s Reagent – potassium bismuth iodide (orange)
• Ferula asafetida • Bouchdart’s Reagent – iodine in KI, most sensitive
• Marme’s Reagent – K cadmium iodide
Balsams – mixtures that contain cinnamic acid, benzoic acid • Sonnencheims’s Reagent – phosphotungstic acid
or both or esters of these acids • Hager’s Reagent – picric acid
• Gold compounds
BALSAM SOURCE
• Tannic acid
Storax/Styrax Liquidambar
- wound healing orientalis A. PYRIDINE-PIPERIDINE ALKALOIDS
- perfumery
- storesin (α and β – Levant’s storax Nicotine
50:50) • leaves of Nicotiana tabacum
- pharmaceutic and compound • use: CNS stimulant, smoking deterrent (Nicoret®)
benzoic tincture (benzoin, storax,
tolu balsam, aloe, ethyl alcohol) Areca, Areca Nut or Betel Nut
Peru Balsam Myroxylon • dried ripe seed of Areca catechu
- parasiticide pereirae • arecoline – anthelminthic-taenicid
Tolu Balsam Myroxylon • tannin content causes oropharengeal cancer
- flavorant, expectorant balsamum • catechutannin → cancer causing
- compound benzoic tincture
(benzoin, storax, tolu balsam, Lobella
aloe, ethyl alcohol) • Indian tobacco
Benzoin Styrax benzoin • Lobella inflata
- Sumatra • Lobeline – CNS stimulant and smoking deterrent (Bantron®)
- Siam → topical compound benzoin
tincture B. TROPANE ALKALOIDS (Solaneous alkaloids)

Resin Acids – oxyacids (-COOH and phenik) Belladona

Glycoresin – resin + carbohydrate • Atropa belladonna
• Anticholinergic, mydriatic
IX. STEROIDS • (-) hyoscyamine → atropine

• Compounds with CPPP; metabolites of mevalonate Hyocyamus or Henbane

pathways • leaves of Hyscyamus niger, 0.04%
• hog +bean → toxic to swine
Sterols
• Cholesterol – animals Egyptian Hyoscyamus or Egyptian Henbane
• Ergosterol – fungi • Hyoscyamus muticus, 1.5%
• Phytosterol – plants

Module 2 – Pharmacognosy Page 9 of 11 RJAV 2022

Duboisia • Heroin
• Duboisia myoporoides • acetylation of morphine
• increase danger of habit formation (very potent)
Withania • Hydromorphone
• Withania somnifera • more potent analgesic
• commercial sources of atropine • less frequent SE
• Apomorphine
Stramonium or Jimson Weed/ Jamestown Weed • condensation of morphine + HCl
• Datura stramonium Solanaceae • use: emetic
• Talumpunay • Hydrocodone
• used for asthma and COPD → burned then vapors are • antitussive
obtained • Opiates
• natural source
Mandragora or European Mandrake/Satan’s Apple • Morphine
• roots of Mandragora officinarum • Serturner
• mandragorine; potent poison • most important, most abundant, narcotic analgesic
• Codeine
Cocaine • P. Robiquet
• Huanuco coca – Erythroxylon coca • most widely used opium alkaloid
• Truxillo coca – E. truxillense • obtained from methylation of morphine
• crack/coke • methylmorphine – antitussive
• psychomotor stimulant, local anesthetic • Noscapine
• Brompton’s cocktail • non-narcotic opium alkaloid
Atropine • antitussive, narcotic/ nicotine
• Antispasmodic, antisialogogue, mydriatic and cycloplegic • Papaverine
• antidote for cholinesterase inhibitors • smooth muscle relaxant, antitussive
• (+) inotropic agent • Thebaine

Scopolamine or Hyoscine E. INDOLE ALKALOIDS (Tryptophan)

• treatment form motion sickness
• Trans-scop® or Transderm® Rauwolfia Serpentina
• dried root of Raubolfia serpentina
C. QUINOLINE ALKALOIDS • constituent: reserpine – treatment of snake bites to insanity,
hypotensive effects, sedative and tranquilizing properties
Cinchona
• Red cinchona bark – Cinchona succirubra Chichi Rica/ Catharanthus/ Vinca
• Yellow cinchona bark – C. calisaya • Cantharanthus roseus
• “cinchonism” • constituents: vinscristine and vinblastine
• Quinine, Quinidine – antimalarial • lymph, hodgkins; aka Periwinkle
• Thalleioquin test = fine blue fluorescence then green ppt
Nux Vomica
Cuprea • dried ripe seed Strychnos nux vomica
• Remijia purdieana, Cupreaceae • Strychnos Ignatii (St. Ignatius Bean) – commercial source of
• commercial source of quinidine strychnine
• Constituents: strychnine (toxic central stimulant) →
D. ISOQUINOLINE ALKALOIDS Mandelin’s Test = violet; Brucine (alcohol denaturant)

Ipecac Physostigmine/Eserine
• dried rhizome and rood of Cephaelis ipecacuanha • local sources: Calabar, ordeal, or Esere Bean
• constituent: emetine or methylcephaeline • from Physostigma venenosum
• use: ipecac syrup –emetic • treatment of Glaucoma
• Ipecac fluidextract is 14 times more potent
• Ipecac + Opium = Dover’s Powder (diaphoretic) Ergot
• Paregoric – camphorated opium tincture • dried sclerotium of Claviceps purpurea on rye, secale cereal
• Laudanum – deodorized opium tincture • constituents: ergonovine (ergometrine & metylsergide –
prophylaxis for migraine) – oxytoxic agent, ergotamine
Sanguinaria or Bloodrood • Lysergic Acid Diethylamide – most active and most
• Sanguinaria Canadensis specific psychomimetic drugs
• constituents: saguinarine
• use: stimulating expectorant and emetic F. IMIDIZOLE ALKALOIDS

Tubocurarine Chloride Pilocarpine

• aka curare or south American arrow poison • leaflets of Pilocarpus jaborandi
• Strychnos castelnaei • treatment of glaucoma
• constituent: tubocurarine –skeletal muscle relaxant
• Pot – clay G. STEROIDAL ALKALOIDS
• Tube – bamboo
• Calabash – gourd Green Hellebore/ Veratrum viride
• Standardization of Tubocurarine – Head Drop Assay in • roots of Veratrum viride
Rabbits – least amount of drug capable of producing muscle • use: cardiac depressant; (-) inotrope
relaxation so that head of animal drops in a characteristic
manner Black Hellebore
• cardiac stimulant
Opium or Gum Opium • (+) inotrope
• unripe poppy seed capsules of Papaver somniferum
• only legal source is India White Hellebore/ European Hellebore
• stone of immortality • roots of Veratrum album
• Marquis Test: opioids (purple) • insecticides
• Synthetic
• Diacetylmorphine

Module 2 – Pharmacognosy Page 10 of 11 RJAV 2022

 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 leaves of Catha edulis
• constituents: cathinone → amphetamine like effects

Peyote/ Mescal Buttons

• aka “shrooms” dried tops of Lophophora williamsii
• hallucinogenic and euphoric agent
• constituent: mescaline (psilycybe → psilocybin)

I. PURINE ALKALOIDS/ METHYLXANTHNES

• Cannot be precipitated by any alkaloidal reagents

Caffeine

• 1,3,7-trimethylxanthine
• Kola, Cola or Kolanuts – dried cotyledon of Cola nitida
• Coffee Bean – dried seeds of Coffea Arabica
• Amaic Acid Test: Red-brown/ transient purple
• C. robusta; C. liberica
• Chlorogenic acid + caffeine (+ caffeole) – (∆) →
• Decaffeinated coffee – 0.08%
• 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
• Tannic acid test: White heavy precipitate
• 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
• Ferrous sulfate test: blue color

SAMPUNG HALAMANG GAMOT

HALAMAN SCIENTIFIC NAME USE

Bayabas Psidium guajava Antibacterial,
Astringent
Alkapulko Cassia alata Antifungal
Bawang Allium sativum Lowers
cholesterol,
↓ Risk of HTN
Yerba Buena Mentha cordifolia Analgesic,
Carminative
Pansit-pansitan Peperomia ↓ Uric acid in
pellucida gouty arthritis
Lagundi Vitex negundo For cough and
asthma
Ampalaya Momordica Hypoglycemic
charantia for DM
Niyug-niyugan Quisqualis indica Anthelminthic
for ringworms
Tsaang Gubat Carmona retusa Antidiarrheal
Sambong Blumea Diuretic
balsamifera

Module 2 – Pharmacognosy Page 11 of 11 RJAV 2022