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PHARMACOGNOSY PHARMACOGNOSY Applied science -> biological, biochemical and economic features of drugs of biological origin and their constituents  Medicinal products in their crude or unprepared formHISTORY OF PHARMACOGNOSYBablylonians  Laws of Hammurabi (172 BC); clay models of human body...

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PHARMACOGNOSY ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------

PHARMACOGNOSY

CRUDE DRUGS

 Applied science -> biological, biochemical and economic features of drugs of biological origin and their constituents  Medicinal products in their crude or unprepared form

– vegetable or animal drugs consists of natural substances that had ; plant exudates

HISTORY OF PHARMACOGNOSY

Natural Substances – formed ; whole plants or parts; animals or organs; had been made Derivatives of Extractives – that are separated and used in a specific manner  Menstruum – solvent; liquid/liquid mixture

Bablylonians  Laws of Hammurabi (172 BC); ; medicinal effects of 250 plants; mages and physician; wheat and barley Ayurveta (2500 BC)  Traditional medicine; “Science of life”; Mother of all healing arts  Charaka – text on internal medicine  Sushruta – 184 chapters; 1120 illness Egyptians (Ebers papyrus – 1150 BC)  ; ; priest and doctors; human anatomy and use of plants Greeks  Dioscorides – wrote “De Materia Medica” or The Medicinal material; aloe, belladonna, colchicum, ergot, opium;  Claudius Galen – described methods and processes of ;

Germans  CA Seydler (1815) – coined the term, “pharmacognosy” from “ ” and “ ” in Analecta Pharmacognistica  JA Schidt (1811) – used the word, “pharmacognosy”; ; described study of medicinal plants and their properties  Fluckiger –   Pellitier and Caventou –  Freidrich Serturner -

 Marc – extraction process is completed

that remarks after

Methods of Extraction  Infusion – (ex. tea); short contact of action  Maceration – of time  Percolation – (ex. Simple Syrup USP)  Digestion  Decoction –  Liquid-Liquid Extraction Partitioning  Distillation Indigenous Plants – plants Rinorea niccolifera – metal eating plant; more on nickel) Naturalized Plants – plants that

(ex.

Preparation of Crude Drugs 1. Collection – ensuring the true natural source of the drug: improper collection, collection time, highest content  Harvesting – specific or proper season; manual labor vs mechanical devices 2. Drying – ; fixed constituents, facilitates grinding and milling; converts plants to convenient form 3. Curing – special drying process that enhances properties of plants’ active ingredients 4. Garbling – final step in preparation of crude drugs; removal of 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     

that contain C, H, and O H and O has same ratio as that of water, thus named CARBO + HYDRATES Photo [C•H2O]n Xylem – H2O Phloem – nutrients – food (∆ source; ∆ storage; structure) Most abundant organic molecule in nature

A. CLASSIFICATION OF CARBOHYDRATES I.

– carbohydrate unit; ; identification test: Benedicts and Barfoed’s = brick red ppt.; *neuramonic – aka sialic PENTOSES  Xylose – “wood sugar”; obtained from boiling corn cobs, straw; ; absorbed but not metabolized o Xylan -> Xylose (aldehyde) -> xylulose (ketoses) HEXOSES –  Glucose – e; is present in C1; reducing sugar as determined by Benedict’s Test; occurs as linear and cylic; o β-D-Glucose – o D-Glucose – aka o Uses:  Parenteral – rigorously purified; as  Pharmaceutic necessity – less rigorous purification; Liquid Glucose – ; ; almost colorless and taste sweet; Dextrose excipient – crystalline sweetening agent (Oral Glucose Tolerance Test – 75g)  Fructose – tohexose = (+)Seliwanoff’s Test: pink/red; ketone group is present in C2; reducing sugar; fruit sugar; sweet fruits and honey; aka (sweetest monosaccharide); obtained from ; honey (mostly sucrose) o High Fructose Sweeteners – isomerization of glucose isomers from Streptomyces sp. o Uses:     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

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- Molasses – residual dark colored syrup after complete crystallization of sucrose; only disaccharide in free state; food and ethanol industry  Maltose – malt sugar; produced-germination of barley; glucose + glucose, α-1,4 bond; major degradation product of starch; reducing sugar (beer, ovaltine, cereal drinks); glu + glu + glu = maltotriose (oligosaccharide – 3-10C)  Lactose – milk sugar (cow’s milk); glucose + galactose, β-1,4 bond; reducing sugar; milk products: 1. Whole milk –(sit)-> butter 2. Butter milk –(churn)-> cream 3. Skimmed milk -> whey (rennin – young calf)  coagulum –(tx)-> cheese * Kamyss – fermented spoiled milk * Condensed Milk – partial condense autoclave, evapo  Lactulose – fructose + galactose, β-1,4 bond; alkaline rearrangement of lactose; converted by lactose to lactic and acetic acid, which causes irritation of the intestines and subsequent cathartics – ideally used with MI and stroke PRODUCTS OF OXIDATIVE METABOLISM  Cherry Juice – ripe fruit of Prunus cerasus (Rosaceae); contains pectin and 1% malic acid; cherry syrup  Plant Acids – uses: acidulants in effervescent formulations; component of buffer systems o Citric Acid – Scheele – lemon juice (1784); citric – Tricarboxylic acid (TCA) –(Deniges Test)-> tartaric (by product, dicarboxylic) = wine o Lactic Acid – acidulant – infant feeding formula, feminine wash (0.2% chlohexidine – vaginal; 0.6% - mouth) – (INSERT)  Alcohol/Ethanol – 95% ethanol by volume 15.56oC; product of fermentation; undergo process of distillation to concentration the alcohol content to 40-55%; low conc. – CNS stimulant; high conc. – CNS depressant o Brandy - wine o Whiskey – malted grain o Rhum - molasses o Diluted Alcohol – 48.4-49.5% ethanol at 15.56% oC PRODUCTS OF REDUCTIVE METABOLISM  Mannitol – from manna, dried exudate of Franxinus ornus; osmotic diuretic and osmotic laxative, GFR; used in people with neurological trauma  Sorbitol – from berries of mountain ash, Sorbus aucuparia; aka D-glucitol; tastes ½ sweet as sugar; used in manufacture of toothpaste and chewing gum  xylitol as alternative

III. POLYSACCHARIDES  Homoglycans – polysaccharides that yield one type of monosaccharide unit upon hydrolysis o Starch – temporary storage form of photosynthetic products from:  Zea mays – corn  Triticum aestivum – wheat  Solanum tuberosum – potato  Oryza sativa – rice  Maranta arundinacea – arrowroot  Constituents: Bases of Differences Structure

Solubility in water Iodine test

Amylose Linear/Helical 250-300 units α-1,4

Amylopectin

Insoluble

Branched (every 25-30 mins) 1000 or more α-1,4 and α-1,6 Soluble

Deep/Dark blue

Blue violet/purple

Enzymes that breaks down starches: 1. Alpha amylase – present in pancreatic juice and saliva; *metabolism/breakdown of carbohydrates starts in mouth 2. Beta amylase – hydrolyses starch to nearly pure maltose Uses: tablet filler, binder and disintegrant; antidote for iodine poisoning Starch Preparations: 1. Pregelatinized starch – chemically or mechanically processed to rupture all or part of granules; tablet binder 2. Sodium starch glycollate – disintegrating agent 3. Hetastarch - >90-99% amylopectin; plasma expander; hydroxyethylstarch; Voluben® 4. Glutens – tacky proteins that impedes flow of starch o Glycogen – storage polysaccharide in animals; more branched than starch (every 10); red color with iodine o Inulin – polyfructan of fructofuranose; Chicorium intybus (Asteraceae) – chicory root; improve digestion; Uses: ingredient in culture media; evaluation of renal function o Dextran – glucosan; Leuconostoc mesenteroides; plasma expander o Cellulose – structural polysaccharide in plants (from the hair of seeds of Gossypium hirsutum)  Purified/Absorbent Cotton – surgical dressing  Soluble Guncotton/Pyroxylin – formed by action of nitric 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: mollusks and arthropods; homoglycan of Nacetylglucosamine  Chitosan – deacetylation of chitin; water purification  Glucosamine – acid deacetylation and hydrolysis of chitin  Heteroglycans – polysaccharides that yield more than one types of monosaccharide units upon hydrolysis

 produced by plants as a ; upon hydrolysis, they yield arabinose, galactose, glucose, mannose, xylose and other uronic acid derivatives  Pb acetate and alcohol LINEAR Less Less Viscosity enhancers

Production

GUMS Pathologic (injury)

Solubility in water

Readily soluble

BRANCHED More More Gelating agents MUCILAGES Physiologic (natural) Slimy mass

PLANT EXUDATES Acacia - Gum Arabic -> arabin -> K, Ca, Mg, Arabic acid; mucilage; emulsifier; suspending agent (33-35%); 12% H2O content; bulk laxative Karaya – most fetid gum Sterculia gum Indian – Ghatti; alternative fro acacia

Astragalus gummifer

Carageenan or Irish Moss

Danish Agar

SOURCE Algae Gelidium cartilagineum Gracilaria confervoides Brown Seaweeds Macrocystis pyrifera Red Algae Chondrus crispus Gigartina mamillosa

Furcellaria fastigiata

Cydonium/Quince Seed Guar Gum or Guaran

GUM Xanthan Gum

SOURCE Action of Xanthomonas campestris on carbohydrates

NOTES Has a pseudoplastic activity enable toothpastes and ointments to spread easily

C. PLANT EXTRACTIVES  Pectin – intracellular cementing materials; partially methoxylated galacturonic acid (swelling); extract of inner portion of rind of citrus fruits (pomelo, grapefruit, orange, ponkan, lemon, calamansi, dalanghita, apple) and apple pomace; antidiarrheal agent; o Kaopectate – Kaolin + Pectin -> antidiarrheal preparation o Protopectin – unripe o Pectin (sol) – just ripe o Pectic acid – overripe

D. GLYCOSIDES

Sterculia urens Anogeissus latifolia

 MARINE GUMS GUM Agar or Japanese Isinglas Algin

SOURCE Seed coat of: Plantago psyllium – Spanish Plantago ovata – Blonde Ripe seed of Cydonia vulgaris Endosperm of Cyamopsis tetragonolobus Endosperm of the seed of Ceratonia siliqua Chocolate substitute

 MICROBIAL GUM

hat may be classified as

Solubility Stability Use

GUM Psyllium

Locust Bean Gum/Carob Pulp or St. John’s Bread

B. GUMS AND MUCILAGES 

 SEED GUMS

CONSTITUENTS

 Heteroglycans; “sugar ethers”; BETA form occur in plants; N-, S-, C-, O, alpha or beta; regulatory, protective and sanitary compounds  Components: glycone (acts as vehicle; inactive) and aglycone (genin; basis for classification; active)  CARDIAC GLYCOSIDES o Unsaturated steroidal aglycone tests  Libermann-Burchard = blue/green; yellow for saturated  Salkowski = red/violet o 2-deoxy sugar glycone test  Keller-Killanii test = reddish brown) o CARDENOLIDES vs BUFADIENOLIDES (C235-B246)

Agarose Agaropectin Mannuronic acid

CARDENOLIDES - Common (active) - C-23 α and β unsaturated 5membered lactone ring

Kappa-gelling component Iota-gelling component Lambda – non-gelling component Kappa

BUFADIENOLIDES - Rare (Bufo sp); (inactive) - C-24 doubly unsaturated 6membered lactone ring

o Digoxin – H2O; Digitoxin – lipid; Desllanatoside – digitalization = rapid o Convallaria – Convallatoxin – Lily of the Valley o Apocynum – Dogbane – cymarine o Adonis – Pheasant’s Eye – adonitoxin 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 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 ; hybrids of Aloe ferox with Aloe Africana and Aloe spicata ; (cathartics and BURNS) i. Constituents: barbaloins and aloe emodin o Rhubarb – glucohein Rheum or Chinese Rhubarb (Therapeutic) Rheum officinale Rheum palmatum

Indian Rhubarb or Himalayan Rhubarb (Ornamental) Rheum emodi Rheum webbianum

o Senna – dried leaflet of Cassia acutifolia ; Cassia angustifolia ; 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

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)

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 LACTONE GLYCOSIDES o Coumarin – from Tonka beans, Dipteryx odorata; constitutents: dicoumarol bishydroxycoumarin  anticoagulant, Warfarin; Test for unsaturated lactone: Kedde’s = blue-violet o Cantharides – from dried insect, Cantharis vesicatoria; Russian/Spanish fly; Blistering fly  Constituents: cantharidin-irritant, vesicant and rubefacient  Causes priaprism – sustained erection o Psoralens – photosensitizing furocoumarins; from Bishop’s flower, Ammi majus  Methoxsalen – repigmentation in vitiligo  Trioxsalen

II. TANNINS  Complex substances or polypeptides that are difficult to separate because they do not crystallize  Phenolic in nature; non-crystallizable polyphenols; protein precipitant (astringent); found in barks and leaves  Local sources: o Guava – Psidium guajava o Kamachile – Pithecolobium dulce o Duhat – Syzigium cumini  Characteristics: o Acidic o Sharp puckering taste o Causes precipitation of alkaloids o Industrial – leather and ink o Clinical – astringents – GI or skin, treatment of burns  Chemical classes: (True tannins vs Pseudo tannins – chlorogenic acid and catechins) A. True Tannins – animal skin  leather; (+) Gold Beater’s Skin Test i. Hydrolyzable – readily hydrolyzed to yield phenolic acids and sugars  Pyrogallol  Leather: bloom  FeCl3 = blue-black; Br2 test = (-) ii. Non-hydrolyzable (aka Condensed Tannins/ Phlobatannins) – results from condensation of catechin and leucocyanidin  tend to polymerize  phlobaphenes (red colored product)  Leather: tanners red  FeCl3 = green-black; Br2 test = (+) B. Pseudo Tannin  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

deposit ova); constituent: tan...