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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 undergone only the processes of collection and drying; plant exudates

HISTORY OF PHARMACOGNOSY

Natural Substances – formed in nature; whole plants or parts; animals or organs; no molecular modifications had been made Derivatives of Extractives – chief principle or constituents of crude drugs that are separated and used in a specific manner  Menstruum – solvent; liquid/liquid mixture used to extract active principle  Marc – undissolved portion of the drug that remarks after extraction process is completed

Bablylonians  Laws of Hammurabi (172 BC); clay models of human body; 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)  Embalming; George Ebers; priest and doctors; human anatomy and use of plants Greeks  Dioscorides – wrote “De Materia Medica” or The Medicinal material; aloe, belladonna, colchicum, ergot, opium; 600 plants  Claudius Galen – described methods and processes of preparing formulas containing plant and animal drug; FATHER OF PHARMACEUTICAL COMPOUNDING Germans  CA Seydler (1815) – coined the term, “pharmacognosy” from “pharmakon” and “gnosis” in Analecta Pharmacognistica  JA Schidt (1811) – used the word, “pharmacognosy”; Lehrbuck de Materia Medica; described study of medicinal plants and their properties  Fluckiger – simultaneous application of various scientific  disciplines with the object of acquiring drugs from every point of view  Pellitier and Caventou – Quinine  Freidrich Serturner - Morphine

Methods of Extraction  Infusion – hot water (ex. tea); short contact of action  Maceration – soaked in solvent for long period of time  Percolation – passage through percolate (ex. Simple Syrup USP)  Digestion - <35-40oC  Decoction – boiling water  Liquid-Liquid Extraction Partitioning  Distillation Indigenous Plants – plants growing in their native countries (ex. Rinorea niccolifera – metal eating plant; more on nickel) Naturalized Plants – plants that grow in foreign land other than their native homes 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 – remove moisture to prevent bacterial and fungal growth with enzymatic degradation; 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  Polyhydric aldehyde or ketone alcohols that contain C, H, and O  H and O has same ratio as that of water, thus named CARBO + HYDRATES Photo  First product of synthesis [C•H2O]n  Xylem – H2O  Phloem – nutrients – food (∆ source; ∆ storage; structure) Most abundant organic molecule in nature

A. CLASSIFICATION OF CARBOHYDRATES I. MONOSACCHARIDES – simplest carbohydrate unit; cannot be hydrolyzed; identification test: Benedicts and Barfoed’s = brick red ppt.; *neuramonic – aka sialic PENTOSES  Xylose – “wood sugar”; obtained from boiling corn cobs, straw; diagnostic aid for intestinal malabsorption; absorbed but not metabolized o Xylan -> Xylose (aldehyde) -> xylulose (ketoses) HEXOSES – most important monosaccharide  Glucose – aldohexose; aldehyde group is present in C1; reducing sugar as determined by Benedict’s Test; occurs as linear and cylic; o β-D-Glucose – most abundant o D-Glucose – aka Dextrose, Blood Sugar, Grape Sugar, Physiologic Sugar o Uses:  Parenteral – rigorously purified; as nutrient  Pharmaceutic necessity – less rigorous purification; Liquid Glucose – syrupy liquid; incomplete acid hydrolysis of starch; almost colorless and taste sweet; Dextrose excipient – crystalline sweetening agent (Oral Glucose Tolerance Test – 75g)  Fructose – ketohexose = (+)Seliwanoff’s Test: pink/red; ketone group is present in C2; reducing sugar; fruit sugar; sweet fruits and honey; aka Levulose (sweetest monosaccharide); obtained from inversion of aq. sucrose solution; honey (mostly sucrose) o High Fructose Sweeteners – isomerization of glucose isomers from Streptomyces sp. o Uses:  Food for diabetic  Ingredient in infant feeding formula  Ingredient in Fructose injection nutruient  Galactose – aldohexose; “Brain Sugar”; C4 epimer of glucose (C2 – mannose); milk:lactose::neuronal fibers:galactosides; Gaucher’s Disease; (+) Mucic acid and Phenylhydralazine = crystal formation (osazone crystals) II. DISACCHARIDES – composed of two monosaccharide units; formed via dehydration synthesis; glycosidic bond  Sucrose – “table sugar”; obtained from: o Saccharum officianarum (sugar cane) – (+) lime = decreased albumin; use SO2  clear = clarification o Beta vulgaris (sugar beets) – cossettes (“cut limps livers” – chop finely) o Acer saccharum (sugar maple) - non-reducing sugar: (-)Benedict’s Test - glucose + fructose, α-1,2 bond - uses: demulcent, sweetening agent to mask taste, coating agent, preservative (85%), production of syrups, retards oxidations

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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

 natural plant hydrocolloids that may be classified as anionic or non-ionic polysaccharides  produced by plants as a protective after injury; upon hydrolysis, they yield arabinose, galactose, glucose, mannose, xylose and other uronic acid derivatives  Pb acetate and alcohol Solubility Stability Use

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; <60% alcohol

BOTANICAL SOURCE Acacia Senegal

Tragacanth Types: vermiform (worm); taragacanth sorts (tear) Constituents: Bassorin (swells: 2/3); traganthin (dissolves: 1/3) SA: 5-6% K: galactomannan -> 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

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 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

GUM Psyllium

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

B. GUMS AND MUCILAGES

LINEAR Less Less Viscosity enhancers

 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 <Tinnevelly>; cultivated in wat lands resembling rice paddies; derivative color: blue green  Constituents: Sennosides A, B, C, and D o Chrysarobin – from Goa powder, Andira araroba; only anthraquinone glycoside that is NOT used as cathartic because it is very irritating; used as keratolytic; hot benzene is used to extract this substance  SAPONINS – foam upon shakin (froth test); bitter, acrid taste; sternutatory (may irritate mucous membrane = sneezing); destroy RBCs of cold blooded animals -> fish poisons; froth, hemolysis, capillary o Glycyrrhiza or Licorice – dried roots of Glycyrrhiza glabra; increase foaminess of beer  Constituents: glycrrrhizia, glycyrrhziac acid o Dioscorea or Yam  Dioscorea spiculiflora – contains diosgenin which is a glucocorticoid precursor;  Dioscorea floribunda – best source of steroids;  Diosgenin – anti-inflammatory o Ginseng – Panax ginseng (Asia); Panax quinquefolius (American); aphrodisiac and an adaptogen  Constituents: panaxosides, ginsenosides, chikusetsusaponins  CYANOPHOIC OR CYANOGENIC GLYCOSIDES o Amygdalin (H2O and amygdalase)  mandelonitrile glucose (H2O and prunase)  mandelonitrile + glucose  benzaldehyde +HCN o Rosaceae

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: tannic acid (Gallic + Ellagic = Tannic [GET])  astringent  Chinese/Japanese Gall – Rhus chinensis; Aphis sp. – gallic acid (Bismuth subgallate – protectant; deodorizer for flatulence)

III. LIPIDS FIXED OILS  Long chain fatty acids + glycerol  From vegetables  Liquid at room temp  EXCEPTIONS: Solid FO – Theobroma, Myristica USE: storage

FATS  Long chain fatty acids + glycerol  From animals  Sold at room temp  EXCEPTIONS: Liquid F: Cod liver oil

USE: storage

WAXES  Long chain fatty acids + high molecular weight alcohol (cetyl alcohol, stearyl alcohol)  EXCEPTIONS: Liquid W: Jojoba oil USE: protectant

 Fatty Acids o Saturated – capric, lauric, myristic, palmitic, stearic, arachidic o Unsaturated (=) – palmitoleic, oleic, linoleic, linolenic, arachodonic  Uses: emollients; vehicles for IM injection (COCOPESE); cathartic (castor oil); soap production; increase caloric value (TPN)  USP Tests: o Acid value or Acid number – mg of KOH needed to neutralize free FAs o Saponification value – mg of KOH needed to saponify the esters o Iodine value – g of iodine absorbed in 100g of sample  Expression – cold-pressed oil; hot-pressed oil; only from fixed oils  Rendering – fats  Solvent extraction – fats; hexane – best solvent for extracting fats  Types of oils – ability to absorb oxygen; oxygen saturates double bonds forming oxides that polymerize to form films; paint industry Non-drying Semi-drying Drying

IODINE VALUE RANGE <100 100-120 >120

EXAMPLES Olive; Almond Cottonseed; Sesame Linseed; Cod liver oil

 Reactions of Lipids o Hydrogenation – liquid oil to semi-solid fat; passing of H with Pd/Ni in 160-200oC; shortening and cooking fat o Sulfation – reaction with sulfuric acid; temp at chilling; sulfates adds to double bonds, surfactants

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IV. FIXED OILS  SEED OILS FIXED OIL Cottonseed Oil – IM injection; not edible; constituent: gossypol –x-> male sterility; ID test: Halphen/Bevan Sesame Seed Oil – Benne/Teel Oil; uses: IM injection, edible; constituent: sesamol (phenol) – self-preserving + lignin  sesamolin & pyrethrin  insecticides; ID test: Bauduoin Coconut Oil – constituents: lauric, myristic, triclycerides Castor Oil – tangan-tangan; ricinoleic (good) - cathartic trcinoleic (good) ricin (toxic) = abrin (jequirity bean) Peanut Oil – peanut oil cake; peanut butter; afflotoxin  aspergillus (due to improper storage and drying) Soybean Oil – stigmasterol - steroid; lecithin – regulate cholesterol; antilipemic agents Corn Oil – germ oil cake – IM injection; antilipemic agents; Hydrogenated volatile oils = sergers Safflower Oil – antilipemic agents Sunflower Oil – antilipemic agents Ethiodized Oil Injection

BOTANICAL SOURCE Gossypium hirsutum

Sesmum indicum

VI. WAXES

Glycine soja

 Spremaceti – head of spermwhale, Physeter macrocephalus; synthetic spermaceti – cetyl ester wax  Jojoba Oil – seeds of Simmondsia chinensis, Buxaceae; hydrogenated form resembles spermaceti; eicosenoic acids: eicosenol and docosenol  Beeswas or Yellow Wax – honeycomb of bees, Apis mellifera; stiffening agent in plasters and cerates; White Wax – bleached yellow wax; myricyl pamitate  Carnuba Wax – leaves of Copernicia prunifera; myricyl cerotate

Zea mays

VII. VOLATILE OILS

Cocos nucifera Ricinus communis

Arachis hypogaea

Carthamus tinctoria Helianthus anuus Iodine addition product of ethyl ester of fatty acid of Poppy seed

 PERICARP OILS FIXED OIL Olive Oil – ID test: Milon’s

BOTANICAL SOURCE Olea europaea

 Cod Liver Oil – from Gadus morrhua; sclerosing agent to obliterate varicose veins; source of vitamin A and D (Scott’s emulsion)  Undecylenic Acid – pyrolysis of ricinoleic acid from castor oil; has antifungal property  Azelaic Acid – onolysis of Castor oil; anti-acne

NOTES Grades: 1. First Grade Virgin Olive Oil – extracted with less pressure 2. Second Grade Virgin Olive Oil – pulp in #1 is extracted with more pressure 3. Technical Oil – extracted with hot water 4. Sulfur Grade – extracted with Carbon disulfide; inferior quality 5. Tournant Oil – fallen and decomposing fruits

V. FATS AND RELATED COMPOUNDS  Theobroma Oil – Theobroma cocao; food for the gods o Uses: cocoa syrup – beverage; cocoa butter – suppository base (melts at 30-35oC) o Nibs  prepared cacao/breakfast cacao  Lanolin – purified fatlike substance from wool of sheep Ovis aries, Boviidae; contains 25% water; Uses: water absorbable ointment base; emollient o Anhydrous lanolin – woolfat (contains 0.25% water)

 Odorous principle in carious plants  Colorless and photosensitive; light resistant tight container in a cool and dry place  Undergoes auto-oxidation and resinification  Plant families: o Glandular hairs or trichomes (lamiaceae  labiatae) o Modified parenchymal cells  piperaceae o Oil tubes or vittae  apiacea (umbelliferae) o Lysigenous and schizogenous passages  pinaceae and rutaceae  Physical characteristics: o Possess characteristic odors, high refractive index, optically active, immiscible in H2O but can be sufficiently be soluble to impart odor in water  aromatic water VOLATILE OILS Distillation Resinification (-) Grease Spot

FIXED OILS Saponification Rancidity (+) Grease Spot

Methods of Obtaining Volatile Oils  Distillation o Water Distillation – dry sample; turpentine oil o Water and Steam Distillation – dry sample; clove and cinnamon oil o Steam Distillation - peppermint and spearmint o Destructive Distillation – empyreumatic oils (heat without access of air); pinaceae and cuppressiaceae – only family to use destructive distillation (“char”)  Enzymatic Actions – mustards  Expressions o Ecuellle and Piquer – rolling a fruit in a trough line with sharp tiny projections enough to puncture the rind – citrus fruit

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© MANOR REVIEW CENTER NOTES (K.L)

o Enfleurage – flower petals (or small plant part) on a fatty pomade followed by EtOH extraction Components of Volatile Oil STEREOPTENE - Solid oxidized hydrocarbon portion - Menthol - Amenthol - Thymol

1. Camphor – Cinnamomum camphora; natural camphor: (+); synthetic camphor: racemic (-); anti pruritic, rubefacient, anti-infective 2. Spearmint – Mentha spicata; carvone (-); (+) carvone – same odor as caraway (Carum carvi) 3. Buchu Oil – Berosma betulina; diosphenol; menstrual problem, carminative, anti-rheumatic 4. Wormwood/Quinghaosu – Artemia annua; Artemisia ketone and camphor; anti-malarial  artemisinin, artenether, artesunate Phenol Volatile Oil 1. Clove Oil – Engenia caryophyllus; eugenol; toothache drops, dental analgesic 2. Thyme – Thymus vulgaris; thymol  antifungal and antibacterial 3. Creosole Oil – Fagus grandiflorus; creosole  disinfectant, guiacol 4. Jupiter Tar – Juniperus oxycedrus; cadinene; antiexzema  Polytar® Phenolic Ether Volatile Oil 1. Nutmeg/Myristica Oil – Myristica fragrans; constitentuents: safrole and myristicin; halloahogen 2. Anise Pimpenella – Pimpenella anisum – anisaldehyde, transanethol 3. Fennel – Freniculum vulgare; fendiole, transanethole

ELEOPLENESES - Liquid hydrocarbon portion - Methysalicylate - Encalyptol - Eugenol

 Medicinal and commercial use: fabrication of perfumes o Top Notes – (smell – minute to hour); most volatile product; leave skin readily – lemon (limonene – most used flavorant), lavender, anise oil o Middle Notes – (3-6 hours); intermediate tenacity and volatility – thyme, neroli and rose oil o Base Notes – (long hours); low volatility and high tenacity; aka Fixatives = staying power  Musk – dried secretion from the preputial follicles of the male musk deer of Asia, Moschus spp – muskane  Civet – glandular secretion appearing in an outwardly discharging pockets of civet cat, Paracloxutus hermaphrodites  Amber gris – most valuable material; pathologic product formed in stomach of spermwhale when if feeds on squid or cattlefish (ambrein)  Constituents of Volatile Oils: o Terpenes – natural products whose structure are made up of isoprene units:  Monoterpene – 2 Hydrocarbon Volatile Oils 1. Turpentine Oil – Pinus palustris; rectified tuperntine; terpinhydrate/terpinol – expectorant; α and β  pinene ** turpentine oil + NaOH = rectified turpentine ** RT + HNO3 = terpinhydrate/terpinol 2. Peppermint Oil – Mentha piperita; menthol (antipruritic)  (+) synthetic, (-) natural; Japanese Peppermint Oil – Mentha arvensis; increase menthol concentration; flavorant, carminative, stimulant counter – irritant *****INSERT HERE********* Aldehyde Volatile Oil 1. Cinnamon Oil – Cinnamomum loureiril; Cinnamomum zeylanicum; Cinnamomum cassia (aka cassia oil); constituent: cinnamaldehyde; uses: flavoring, carminative, antiseptic 2. Lemon Peel Oil – rind of the fruit Citrus limon; lemon oil; citral and limonene 3. Citronella Oil – leaves of Cymbopogon winterianus – tanglad; citronellal; insect repellant 4. Hamamelis Oil – Hamamelis virginiana; 2-hexanal; hemorrhodal preparation Ketone Volatile Oil

   

Sesquiterpene - 3 Diterpene - 4 Triterpene - 6 Tetraterpene – 8 o Acetate-Mevalonate Pathways o Shikimic Pathway – aromatic compound

VIII. RESIN AND RESIN COMBINATION RESINS – amorphous products with complex chemical nature; hard transparent or translucent and when heated they soften and melt; complex mixtures of:  Resin acids  Resin alcohols  Resinotannols  Esters  Resenes – B-complex neutral substances devoid of characteristics RESIN Rosin/Colophony Podophyllum

SOURCE Pinus palustris Podophyllum peltatum

Eriodictyon/Yerba Santa

Eriodictyon californicum

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CONSTITUENTS/NOTES Podophyllin – caustic agent for warts Peltatin – purgative Podophyllotoxin – etoposide, tenoposide

© MANOR REVIEW CENTER NOTES (K.L)

Jalap

Exogonium purge Pistacia lentiscus Piper methysticum Tops of Cannabis sativa

Mastic Kava/Kava-kava Cannabis/Indian Hemp/ Marijuana/Pot

Jalapin and purganol – drastic purgative Masticin and mastichic acid Styrylpyrones – yangonin, kawaiin, methysticin Resin: Hashish Constituets: THC, Cannabidiol, nabilone Duquenois Test: violet on chloroform layer

RESIN COMBINATIONS:  Oleoresins – volatile oils + resin

X. ALKALOIDS

OLEORESINS Turpentine/ Gum Turpentine Capsicum/ Cayenne Pepper – African chilles Ginger

SOURCE Pinus palustris

CONSTITUENTS

Capsicum frutescence C. annum var longum (Louisiana long pepper) Zingiber officinale

Capsaicin – vesicant; irritant

White Pine Balsam Comaiba

Pinus strobus Copaifera spp.

of

Zingebol and bisabolene – stomachic; antibacterial

 Oleo-Gum-Resin – volatile oil + gum + resin o Myrrh/Gum Myrrh – Commipholra molmol; use: astringent (Astring-o-sol®) o Asafetida – Devil’s dung; Ferula asafetida  Balsams – mixtures that contain cinnamic acid, benzoinc acid or both or esters of these acids BALSAM Storax/Styrax – wound healing; perfumery; storesin (α and β – Levant’s storax 50:50); pharmaceutic and compound benzoic tincture (benzoin, storax, tolu balsam, aloe, ethyl alcohol) Peru Balsam – parasiticide Tolu Balsam – flavorant, expectorant; compound benzoic tincture (benzoin, storax, tolu balsam, aloe, ethyl alcohol) Benzoin – Sumatra; Siam  topical compound benzoin tincture

o Secondary – fermentation of primary bile acids by intestinal flora; desoxycholic acid, litocholic acid  Steroid Hormones o Glucocorticoids – carbohydrate metabolism; antiinflamatory; cortisone, cortisol o Mineralocorticoids – electrolyte and water balance; aldosterone o Sex Hormones – Males: androgens, testosterone; Females: estrogen, progestin

SOURCE Liquidambar orientalis

Myroxylon pereirae Myroxylon balsamum

Styrax benzoin

 Resin Acids – oxyacids (-COOH and phenik)  Glycoresin – resin + carbohydrate

IX. STEROIDS  Compounds with CPPP; metabolites of mevalonic pathways  Sterols o Cholesterol – animals o Ergosterol – fungi o Phytosterol – plants  Bile Acids o Primary – directly from cholesterol (liver); cholic acid, chenodeoxycholic acid

 Bitter, basic nitrogenous compounds; physiologically active; most of them ends in –ine;  Nitrogen can be: Primary amine – RNH2; Secondary amine – R2NH; Tertiary amine – R3N  All are solids except for: [CANS] o Coniine – Coniium maculatum; poison hemlock (Socrates) o Arecoline – scotchbroom (Cysticus coparius), lupin – Lupinus mutabilis – anti-arrhythmic o Nicotine o Sparteine  Alkaloidal Reagents – form double salts with compounds of mercury, gold, platinum, and other heavy metals o Wagnner’s Reagent – iodine in KI (red-brown) o Mayer’s Reagent – potassium mercuric iodide (cream) o Valser’s Reagent – mercuric iodide (white) o Dragendorff’s Reagent – potassium bismuth iodide (orange) o Bouchdart’s Reagent – iodine in KI, most sensitive o Marme’s Reagent – K cadmium iodide o Sonnencheims’s Reagent – phosphotungstic acid o Hager’s Reagent – picric acid o Gold compounds o Tannic acid

A. PYRIDINE-PIPERIDINE ALKALOIDS  Nicotine – leaves of Nicotiana tabacum; use: CNS stimulant; smoking deterrent (Nicoret®)  Areca, Areca Nut or Betel Nut – dried ripe seed of Areca catechu; arecoline – anthelminthic-taenicid; tannin content causes oropharengeal cancer; catechutannin  cancer causing  Lobella – Indian tobacco; Lobella inflata; Lobeline – CNS stimulant and smoking deterrent (Bantron®)

B. TROPANE ALKALOIDS (Solaneous alkaloids)  Belladona – Atropa belladonna; anticholinergic, mydriatic; (-) hyoscyamine  atropine]  Hyocyamus or Henbane – leaves of Hyscyamus niger, 0.04%; hog +bean  toxic to swine  Egyptian Hyoscyamus or Egyptian Henbane – hyoscyamus muticus, 1.5%

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© MANOR REVIEW CENTER NOTES (K.L)

 Duboisia – Duboisia myoporoides  Withania – Withania somnifera; commercial sources of atropine3  Stramonium or Jimson Weed/Jamestown Weed – Datura stramonium Solanaceae; Talumpunay; used for asthma and COPD  burned then vapors are obtained  Mandragora or European Mandrake/Satan’s Apple – roots of Mandragora officinarum; mandragorine; potent poison  Cocaine – Huanuco coca – Erythroxylon coca; Truxillo coca – E. truxillense; crack/coke; psychomotor stimulant, local anesthetic; Brompton’s cocktail  Atropine – antispasmodic; antisialogogue; mydriatic and cycloplegic; antidote for cholinesterase inhibitors; (+) inotropic agent  Scopolamine or Hyoscine – treatment form motion sickness; Trans-scop® or Transderm®

C. QUINOLINE ALKALOIDS  Cinchona – Red cinchona bark – Cinchona succirubra; Yellow cinchona bark – C. calisaya; “cinchonism”; Quinine, Quinidine – antimalarial; Thalleioquin test = fine blue fluorescence then green ppt  Cuprea – Remijia purdieana, Cupreaceae; commercial source of quinidine

D. ISOQUINOLINE ALKALOIDS  Ipecac – dried rhizome and rood of Cephaelis ipecacuanha; constituent: emetine or methylcephaeline; use: ipecac syrup – emetic o Ipecac fluidextract is 14 times more potent o Ipecac + Opium = Dover’s Powder (diaphoretic) o Paregoric – camphorated opium tincture o Laudanum – deodorized opium tincture  Sanguinaria or Bloodrood – Sanguinaria Canadensis; constituents: saguinarine; use: stimulating expectorant and emetic  Tubocurarine Chloride – aka curare or south American arrow poison; Strychnos castelnaei; constituent: tubocurarine – skeletal muscle relaxant o Pot – clay o Tube – bamboo o Calabash – gourd o Standardization of Tubocurarine – Head Drop Assay in Rabbits – least amount of drug capable of producing muscle relaxation so that head of animal drops in a characteristic manner  Opium or Gum Opium – unripe poppy seed capsules of Papaver somniferum; only legal source is India; stone of immortality; Marquis Test: opiods (purple); synthetic o Diacetlymorphine – Heroin; acetylation of morphin; increase danger of habit formation (very potent)

o Hydromorphone – more potent analgesic; less frequent SE o Apomorphine – condensation of morphine + HCl; use: emetic o Hydrocodone - antitussive o Opiates – natural source  Morphine – Serturner; most important, most abundant, narcotig analgesic  Codeine – P. Robiquet; most widely used opium alkaloid; obtained from methylation of morphine; methymorphine – antitussive  Noscapine – non-narcotic opium alkaloid; antitussive; anarcotin/narcotine  Papeverine – smooth muscle relaxant, antitussive  Thebane

E. INDOLE ALKALOIDS (Tryptophan)  Rawolfia Serpentina – dried root of Raubolfia serpentina; constituent: reserpine – treatment of snake bites to insanity, hypotensive effects, sedative and tranquilizong properties  Chichirica/Catharanthus/Vinca – Cantharanthus roseus; constituents: vinscristine and vinblastine; lymph, hodgkins; aka Periwinkle  Nux Vomica – dried ripe seed Strychnos nux vomica; Strychnos Ignatii (St. Ignatius Bean) – commercial source of strychnine; constituents: strychnine (toxic central stimulant)  Mandelin’s Test = violet; Brucine (alcohol denaturant)  Physostigmine/Eserine – local sources: calabar, ordeal, or Esere Bean; from Physostigma venenosum; treatment of Glaucoma  Ergot – dried sclerotium of Claviceps purpurea on rye, secale cereal; constituents: ergonovine (ergometrine & metylsergide – prophylaxis for migraine) – oxytoxic agent, ergotamine o Lysergic Acid Diethylacmide – most active and most specific psychomimetic drugs

F. IMIDIZOLE ALKALOIDS  Pilocarpine – leaflets of Pilocarpus jaborandi; treatment of glaucoma

G. STEROIDAL ALKALOIDS  Green Hellebore/Veratum viride – roots of Veratrum viride; use: cardiac depressant; (-) inotrope  Black Hellebore – cardiac stimulant; (+) inotrope  White Hellebore/European Hellebore – roots of Veratum album; insectesies

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© MANOR REVIEW CENTER NOTES (K.L)

H. ALKALOIDAL AMIDES  Ephedra/Ma Huang – ephedrine; overground portion of Ephedra sinica; nasal decongestant; bronchodilator  Colchicine – Colchicum autumnale, Liliaceae; used in plant genetics because it can double the chromosomes  Khat/Abyssynian Tea – fresh leaces of Catha edulis; constituents: cathinone  amphetiamine like effects  Peyote/Mescal Buttons – aka “shrooms”dried tops of Lophophora williamsii; hallucinogenic and euphoric agent; constituent: mescaline (psilycybe  psilocybine)

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

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© MANOR REVIEW CENTER NOTES (K.L)

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