Pharmacognosy Module 2 PDF

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Module 2 – Pharmacognosy Page 1 of 12 RJAV 2022  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 Module 2 – Pharmacognosy Page 2 of 12 RJAV 2022 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 Module 2 – Pharmacognosy Page 3 of 12 RJAV 2022 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 Module 2 – Pharmacognosy Page 4 of 12 RJAV 2022 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 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) Module 2 – Pharmacognosy Page 5 of 12 RJAV 2022  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 Module 2 – Pharmacognosy Page 6 of 12 RJAV 2022  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 Module 2 – Pharmacognosy Page 7 of 12 RJAV 2022  IODINE VALUE RANGE EXAMPLES V. FATS AND RELATED COMPOUNDS Non-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 8 of 12 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 9 of 12 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 10 of 12 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 11 of 12 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 12 of 12 RJAV 2022