Pharmacognosy PDF

Pharmacognosy ▪ Harvesting Knowledge on drugs ✓ Timing: Quality / Quantity Pharmakon = drug Gnosis =knowledge ✓ Natural drugs...

Pharmacognosy ▪ Harvesting Knowledge on drugs ✓ Timing: Quality / Quantity Pharmakon = drug Gnosis =knowledge ✓ Natural drugs ▪ Drying – ⊖ moisture / H2O Biological ✓ to protect the sample from microbial damage Biochemical ✓ ↓ enzyme activity Economic features Fluckiger: Scope of pharmacognosy features ▪ Curing – specialized method of drying ✓ Various scientific disciplines ✓ Fresh samples: Toxic, Irritating Simultaneous application ↓ Toxicity, ↑ Yield ▪ Garbling – final step of crude drug preparation Crude Drugs ✓ Separation of extraneous matter Undesired Plant parts Vegetable or animal drugs that consist of natural Dirt substances that have undergone only the process Soil of (1) Collection (2) Drying Terms ▪ Packaging, Storage and Preservation – (optional) ✓ Natural substance – Substances that are found ✓ Packaging: Physical protection in nature Single ↑ marketability ✓ Extractives / Derivatives – Active ingredient Mixture ✓ Extraction: ✓ Storage: protection from animal invasion (insects, rodents) Marc – Residue left after extraction Menstruum – solvent for extraction ✓ Preservation: ▪ Fats – Hexane (non-polar substance or 1. Heating - 65 °C solvent 2. Fumigant: Methyl Bromide ▪ Resins – Hard transparent / 3. Chloroform / CCI4 Translucent, Alcohol (good for extraction resins) ▪ Chlorophyll – Acetone (extraction of Drug evaluations green pigments)  Organoleptic – “sense organ” ▪ Chrysarobin – Keratolytic agent, Hot? ✓ Evaluation using the Benzene (extraction) ✓ Macroscopic evaluation Naturalized Plants – Foreign Country  Microscopic Indigenous Plants – Native Country ✓ Use of a microscope – anatomical examination Crude Drug Preparation  Biologic CHAD CurGa Pa ✓ Use of animals – Bioassay (for ▪ Collection C – Collection pharmacologic profile of drug) ✓ from wild plants Ha – Harvesting D – Drying ✓ ensuring the true  Chemical – chemical treatment Cur – Curing natural source of the Ga – Garbling ✓ Best method drug. Pa - Packaging ✓ Qualitative testing: e.g. Iodine test, Fehling test ✓ Quantitative testing: e.g. Titration   Physical Glucose + Glucose → 2 sugar units, 1 type of sugar ✓ Physical constants: o Specific gravity O O = = o Melting point/boiling point Monosaccharides → R C – H RC–R o Refractive index NAME ALDOSE KETOSE o Optical activity = polarimeter DIOSE = 2C Hydroxy ✗ acetaldehyde TRIOSE = Glyceraldehyde Dihydroxyacetone Drug classification 3C ⇆ ◼ Morphologic: plant part used (e.g. seed, leaves, TETROSE = Erythrose threose Erythrulose etc) 4C PENTOSE = Ribose Ribulose 5C Arabinose ◼ Taxonomic: plants / animal → botanic/ zoologic Xylose ✓ Phylogeny: evolutionary relationship, natural “HEXOSE”= Mannose relationship between plants and animals 6C “Glucose” – most Fructose – (old MOST important, and name: Levulose IMPORTANT most abundant “left”) ◼ Pharmacologic / therapeutic Galactose → Medicinal use Atropine anti cholinergic Ach -Tautomerization [isomerization] Bethanechol Parasympathetic drugs Pilocarpine Aldose(-oso) ⇆ ketose (-ulose) ◼ Chemical Important monosaccharides → Constituents ◼ Xylose → most preferred ✓ Aka wood sugar ✓ Acid hydrolysis Carbohydrates → hydrates of carbon, “CHO” / ✓ Obtained from corn cob “C2H2O” ✓ Diagnostic aid (Malabsorption ◼ Building Blocks: “Monosaccharides”, (bond: Syndrome) Glycosidic Bond) → “Ether bond / linkage” Functional Groups: Alcohols, Aldehyde, Ketones → “Polyhydroxy aldehyde / Polyhydroxy ketone” Cob + “Acid” → Xylose ◼ Reactions ✓ Synthesis: “Dehydration” (to form glycosidic bonds, ⊖ H2O) ◼ D-Glucose +/- ✓ Degradation: “Hydrolysis” (to break bonds ✓ Optical activity ⊕ = dextrose “from complex to simpler”, ⊕ H2O) ✓ Physiologic sugar, blood sugar, grape Classes of Carbohydrates sugar, corn sugar ✓ Use: nutrient, flavorant UNITS TYPE ✓ Note: glucose can be given PO, SC, IV Monosaccharides Always 1 Always 1 or enema Disaccharides Always 2 Up to 2 Oligosaccharides 2 - 10 1 or more (≠ ◼ Liquid glucose 11) Aka Glucose syrup Polysaccharides >10 1 or more - Aka Glycans Obtained via partially hydrolyzing starch Homoglycans > 10 Always 1 Starch → liquid glucose Heteroglycans > 10 >1  ◼ Maltose – Glucose + Glucose (α – 1,4) ◼ Dextrose excipient ✓ Aka Malt sugar, maltobiose Aka Dextrose ✓ Bond: α – 1,4 monohydrate ✓ Obtained from germination of barley Used to promote adhesion (binders, fillers) ◼ Lactose ✓ Aka: Milk sugar Related Compounds ✓ Fresh cow’s milk Bos taurus ◼ Calcium gluconate → Fam: Bovidae ◼ Ferrous gluconate → used for Iron deficiency ✓ Lactose = Galactose + Glucose anemia (IDA) Bond: β 1,4 Important monosaccharides cont. churned ◼ D-Fructose Fat globules (cream) Butter ✓ Latin word: Fructus = fruit; -OSE for Removal of cream Skimmed Liquid: butter milk carbohydrate milk Coagulum → cheese ✓ Aka Levulose = Levorotatory Addition + of rennin Whey → Lactose + ✓ Obtained from fruits and honey, inorganic salts hydrolysis of insulin Isolation of Lactose ✓ Sweetest monosaccharides ✓ Use: food for diabetics  When milk is allowed to stand a few hours, the fat globules (cream) rise to the Glycemic Index Sugars GI value top. What is Glycemic index?  When churned, the fat globules unite to Maltose 105 Ranks carbs from 0 to 100 Glucose 100 form butter, leaving a liquid known as according to how much Rice syrup 98 buttermilk they cause the blood sugar Sucrose / 65  The milk left after separation of cream is to rise after they’re eaten Table known as skimmed milk, which if treated sugar with rennin, forms a coagulum. Upon Lactose 46 proper treatment, this coagulum is made Fructose 23 into cheese. The liquid separated from coagulum is known as whey and contains Disaccharides lactose and inorganic salts. ◼ Sucrose – aka “table sugar” ✓ Products: Glucose + Fructose Disaccharides continuation (Bond: α – 1,2) → non-reducing sugar ◼ Lactulose = Galactose + Fructose (β 1,4) ✓ Sources ✓ A semi-synthetic sugar prepared by Sugar cane Saccharum officinarum alkaline rearrangement of lactose Sugar beet Beta vulgaris ✓ Hydrolytic product galactose + fructose Sugar maple Acer saccharum ✓ Uses: Addition of lime (neutralize 1. Laxative (Osmotic) Iron roller plant acids) 2. Portal systemic encephalitis (↑ NH3) After heating sucrose → Invert Fermentation sugar + lime = coagulum → anaerobes removed (SCUM) Lactulose Acetic acid + Lactic acid Neutralizes plant acid Filtered using decolorizer (laxative) Crystallization (Sulfur dioxide) green to clear color Dark colored substance (molasses) Fermented molasses = rum Oligosaccharides ◼ Cellulose ✓ Component of plant cell wall ◼ Trisaccharides ✓ Source: cotton plant ✓ Maltotriose = Gluc + Gluc+ Gluc (S.N. Gossipium hirsutum) ✓ Raffinose = Gal + Gluc + Fruc ✓ Related compounds ✓ Gentianose = Gluc + Gluc + Fruc 1. Methylcellulose ◼ Tetrasaccharides binder 2. Ethyl cellulose ✓ Stachyose = Gal + Gal + Gluc + Fruc 3. CAP cellulose acetate …. → enteric coating / tablet coating Polysaccharides ◼ Inulin ◼ Homoglycans ✓ Aka Dahlia starch ✓ Glucosans (or Glucans) → purely → diagnostic test → kidney function glucose test ✓ Fructosans (or Fructans) → fructose (Glomerular filtration rate) ◼ Heteroglycan Heteroglycan ✓ Gums and mucilages ◼ Sugar units: number of sugar ✓ GAGs = glycosaminoglycans ◼ Sugar types: ✓ Di -heteroglycan: Algin, carrageenan Homoglycans ✓ Tri – heteroglycan: xanthan ◼ Starch → technically a glucosan ✓ Tetra – heteroglycan: gum Arabic, ✓ Aka plant starch psyllium seed gum ✓ Souces: ✓ Penta – heteroglycan: tragacanth, ghatti Corn (Zea mays) gum Potato (Solanum tuberosum) GUMS Wheat (Triticum aestivuum) ◼ Gums Tapioca (Monihot asculenta) ✓ Natural plant hydrocolloids AMYLOSE AMYLOPECTIN  Emulsifiers STRUCTURE Linear Branched  Suspending agent BONDS α-1,4 α-1,4 ; α-1,6 PERCENTAGE 20-25% 75 – 80% Shrub and tree exudates IODINE TEST Deep blue Blue violet/ ◼ Tragacanth purple ◼ S.N. Astragalus gummifer ◼ Forms Related compounds ✓ Vermiform: worm like appearance, ◼ PGS = Pregelatinized starch natural ✓ Use: tablet binder/filler ✓ Tragacanth sorts: tear-like, natural ◼ Sodium starch glycolate ✓ Ribbon/flake gum: longitudinal striations, ✓ Use: disintegrant (↑ breakup) man made ◼ Hetastarch ◼ Components ✓ Use: 6% plasma expander 1. Bassorin = Tragacanthic acid → water insoluble but swellable Homoglycans continuation. 2. Tragacanthin → water soluble ◼ Glycogen ◼ pH requirements glycogenesis Glucose Glycogen ✓ Aka animal starch ✓ More complex than starch ✓ Iodine test: wine red / mahogany red Shrub and tree exudates SEED GUMS ◼ Psyllium seed ◼ Acacia / Gum Arabic Obtained from: ✓ Source: Acacia Senegal 1. Blond psyllium or Indian plantago (S.N. ✓ Constituent: Arabin Plantago ovata) ✓ Use: suspending agent (35%) 2. Black psyllium or French plantago (S.N. ↓ Settling suspensions Plantago indica) ◼ Ghatti gum / Indian gum Use: husk (seedcoat): Laxative (bulk ✓ S.N. Anogeissus latifolia laxative) ✓ Use: acacia substitute ◼ Guar gum ◼ Karaya gum / Sterculia gum o aka Guara ✓ S.N. Sterculia urens o Obtained from Cyamopsis tetragonolobus ✓ Uses: o Bulk laxative o Emulsifier ◼ Locust Bean o Dental adhesive o Aka St. John’s bread, Carob pulp Marine Gums o Obtained from Ceratonia siliqua o Use: chocolate substitute ◼ Algin = Alginic acid ✓ From a brown algae, Giant Kelp [largest algae] (S.N. Macrocystis pyrifera Microbial gums ✓ Uses: Xanthan gum - Thicker, gelling agent ✓ Related compound: Na alginate →  Prepared by the fermentation of glucose and Gaviscon sucrose with the action of Xanthomonas Cytoprotectant campestris ◼ Agar  Has pseudoplastic property ✓ From a red algae, Japanese isinglass  Use stabilizing agent(emulsion): viscosity ▪ S.N. Gelidium cartilagineum enhancer(thickener) ▪ S.N. Gracilaria confervoides  Glucose →Heteroglycan ✓ Agar is a mixture of 1. Agarose (↓ SO4) Dextran gum 2. Agaropectin (↑ SO4) ◼ Carrageenan KIL? Prepared by the fermentation of sucrose with the ✓ Obtained from a red algae, Irish moss action of Leuconostoc mesenteroides o S.N. Chondrus crispus Use hetastarch plasma expander o S.N. Gigartina mamillosa → false irish moss (but still a source of carrageenan) Other heteroglycans ✓ Pectin ◼ Furcellaran ✓ Aka Danish agar, black carrageenan Purified carbohydrate on inner portion of rind of ✓ Obtained from a red seeweed, clawed citrus fruits fork weed Uses ✓ S.N. Furcellaria lumbricalis (formerly Furcellaria fastigiate) Gelling agent Suspending agent Nucleus = Steroid nucleus – Test = Legas’s Antidiarrheal Cyclopentanoperhydrophenanthrene Test (red/pink Pectin in [CPPP] Use: Cardiotonic Test for Unripe fruits protectin [Cardiac Stimulant] digitoxose (a Ripe fruits soluble pectin ✓ ↑ Inotropy deoxysugar ) = ✓ Congestive Heart Failure keller-kiliani Overripe fruits pectic acid (CHF) test Other carbohydrate related compounds reductive metabolism Mannitol Digitalis purpurea Digitalis lanata (Lanoxin) 1. Digitoxin 1. Digoxin Reduction of mannose 2. Gitoxin 2. Lanatoside A to E Source of manna (s.N. Fraxinus arnus) 3. Gitaloxin Osmotic diuretic / laxative Na+ Sorbitol Na+ / Ca +2 ↑ Aka d- glucitol Inotropy ↑ Reduction of glucose Source: ripe berries (s.n. Sorbus aucuporia) Lily of the valley Convallaria majalis Convallatoxin = strophantin + rhamnose Osmotic laxative Christmas rose Helleborus niger Helleborin, Helleborein, Hellebrin Carbohydrates = sugar + sugar Glycosides bond = glycosidic Squill Urginea maritima Scillaren A/B ◼ Aka: Sugar “Ether” → Glycosidic bond, Glycone (Sugar portion) and Aglycone (non- Apocynum, Apocynum Cymarin cannabinum sugar portion)(genin) components Dogbane, Black Indian hemp ◼ Components: Oleander Nerium oleander Oleandrin = oleandrigenin + I- oleandrose Glycone Genin Adonis / Pheasant’s Adonis vernalis Cymarin eye Strophanthus Strophanthus kombe K - strophantoside Glycosidic bond Salicin Cardiac Glycosides Anthraquinone Glycosides Nucleus: Test: Borntrageis Test (Red / Pink Foxglove = Grecian foxglove = color) Antharacene  2. American ginseng (S.N. Panax quinquefolius) 3. Japanese ginseng ( S.N. Panax japonicum) Dammarane - Ginsenosides (Japan) Use: saponins Panaxosides (Russia) Acid hydrolysis yields panaxadiol or ✓ Stimulant Laxative panaxatriol Except: Chysarobin [keratolytic “tissue Glycans Panaxans destruction” Acetylenic Panaxynol compound Panaxydol Sesquiterpene Panacene Japanese Ginseng variety that contains Rhamnus purshianus Cascara sagrada ginseng chikusetsusaponins? Cassia acutifolia Senna Andira aroroba Goa powder Aloe barbadensis Aloe Ginseng uses Rheum officinale Rhubarb 1. Tonic Rhamnys frangula Frangula = Buckthorn ↑ physical performance bark 2. ↑ Sexual performance 3. Agent for Iron defeciency anemia 4. Adaptogen = anti-stress Aka slimming tea Senna Not a cathartic, only keratolytic Chrysarobin Cyanogenic Glycosides Used to reduce the bitter taste of MgO cascara sagrada ◼ Enzyme: Emulsin = ( Amygdalase + Prunase) Used to increase the % yield of Hot ◼ Wildcherry Emulsin extracted chrysarobin benzene ✓ Amygdalin Prunasin Cascarosides A and B optical isomers of Barbatoin Partial hydrolysis Carcarosides C and D optical isomers of Chrysoloin ◼ Amygdalin ✓ Modified form = Laetrile – similar to Vit B17 Saponin glycosides – dangerous at too much amount ✓ Has anti – caner claims (unproven) ◼ Apricots [hemolyis] ✓ Prunus armeniaca ✓ Laetrile ◼ Glyxyrrhiza Emulsin Emulsin ✓ S.N. Glyxyrrhiza glabra ✓ Constituent: glycyrrhizin ( 50x sweeter than Amygdalase Prunase sucrose) amygdalin Prunasin (Where RR’ = gentiobiose) (Where R = glucose) ✓ Use: sweetening agent ( bitter taste of quinine preparation) Question: What is produced after partial hydrolysis of ✓ CI: Na = Hypertension amygdalin? Prunasin K = hypokalemia ◼ Cassava Dioscorea ✓ S.N. Mannihot esculenta ✓ S.N. Dioscorea loribunda ✓ Toxic component: Maninotoxin; Linamarin Precurses for glucocorticoid synthesis ◼ Flaxseed Ginseng ✓ Toxic component: Linamarin ✓ Obtained from 1. Asian ginseng (S.N. Panax ginseng) Isothiocyanate glycosides – sulfur containing (thio) ◼ Enzyme: Myrosin ◼ Black mustard ✓ Brassica nigra Myrosin ✓ Constituent: Sinigrin → allyl Isothiocyanate ◼ Cantharides aka spanish fly, russian fly , blister ◼ White mustard fly [vesicant] ✓ Brassica alba Myrosin ✓ Constituent ✓ Constituent: Sinalbin → acrinyl ✓ Use: irritant; vesicating agent Isothiocyanate ◼ Garlic ✓ Allium sativum Uncrushed (o) Crushed Constituent: Alliin Constituent: Allicin ✓ Use: Hypolipidimic agent (only in Raw ◼ Bishop’s weed garlics) ✓ Ammi majus ✓ (allicin) Same as statins [MOA: inhibit the ✓ RE-pigmentation HMG – CoA reductase enzyme] ✓ Used in people with vitiligo Alcohol glycosides ◼ Willow Bark ✓ Source: Salix purpurea Emulsion Salicin Saligenin (salicyl alcohol + D - Glucose Aldehyde glycosides Flavonol glycosides ◼ Vanilla bean ◼ Rue/ Herb-of-grace ✓ Source: Vanilla planifolia ✓ Obtained from Ruta graveolens ✓ Use: Flavorant → Vanillin ✓ Rutin = Vitamin P (permeability factors) o Quercetin (antioxidants) + rutinose ◼ Buckweed ✓ Obtained from Fagopyrum tataricum ✓ Quercitrin Phenol Aldehyde o “quercetin + rhamnose” ◼ Bearberry Lipids ✓ Aka Uva – ursi = grape of the bear ◼ Properties ✓ Source: Arctostaphylos uva – ursi 1. Non-polar ✓ Content: ArbutinDiuretic Astringent 2. Hydrophobic Anti-inflammatory 3. Lipophilic Lactone glycosides Cyclic ester ◼ Tonka bean Fixed Oils [only solid fixed oil is theobroma oil] ✓ Dipteryx adorata ◼ Coconut oil ✓ Coumarin → Flavorant Obtained from Cocus nuficera  ◼ Palm oil ✓ Nutritive component: Sesamol Obtained from Elaeis guineersis Saturated fatty acids ◼ Almond oil ◼ Palm kernell oil “Lauric acid” ✓ Obtained from Prunus amygdalus Obtained from Elaeis guineensis ◼ Apricot kernel oil ✓ Obtained from Prunus armeniaca ◼ Corn oil ✓ Obtained from Zea mays ◼ Safflower oil ✓ Obtained from Carthamus tinctorius -ic acid [saturated]; -eic, enic, onid [unsaturated] ◼ Sunflower oil ◼ Castor oil ✓ Obtained from Helianthus annuus S.N. Ricinus communis ◼ Linseed (Flaxseed) oil → used in paint industry 1. Ricin – TOXIC ✓ Obtained from Linum usitatissimum (o) 2. Ricinolein Ricinoleic acid [Laxative] ✓ Drying oil (Iodine value (IV) > 120%) 3. Undecylenic acid – Anti-fungal 4. Azelaic acid – Anti-acne Which is not used as “IM for injection”?  Used: Sesame, Cottonseed, Corn, Arachis/ Peanut  Not used: Coconut ◼ Olive oil: S.N. Olea europaea [sweet oil] 1. Virgin = application of gentle pressure, without heat; cold press. Fats → Solids except “cod liver oil” 2. Technical = Hot press; added hot water ◼ Lanolin (Hydrous woolfat) → 25-30% 3. Tournant = Olive fruit → fermentative ✓ Anhydrous lanolin: 0.25% 4. Sulfur olive = CS2 (menstruum) ✓ Obtained from Sheep [S.N. Ovis aries] Disadvantage: Expensive ✓ Use: Ointment base → absorption ointment Oleic acid [18:1] bases ◼ Cod liver oil ✓ Obtained from Gadus morrhua ✓ Rich in Vitamins A and “D” → management of rickets/ anti-rickets ✓ Obliterates varicose veins ◼ Peanut oil ✓ Obtained from Arachis hypogaea AnimalWaxes - ↑MW alcohol, ↑MW fatty acid ✓ Source of Vit. B1 = thiamine ◼ Spermaceti ✓ Obtained from Sperm whale o S.N. Physeter macrocephalus ✓ Synthetic form: Cetyl ester wax Euricic acid: 0.2 – 2% ✓ Ambergris → Useful in perfumery → fixative bleached Lea – R [low euricic acid ◼ Beeswax “aka Yellow wax” White ◼ Rapeseed oil or Canola oil →- rapeseed wax ✓ Obtained from Brassica campestris ✓ Obtained from Honey bee; S.N. Apis mellifera ✓ Contains Euricic acid (50%) ✓ Constituent: Myricyl palmitate ◼ Soybean oil ✓ Hydrocarbon/oleaginous ointment base ✓ Obtained from Glycine soja ✓ Sterol content: Stigmasterol; Lecithin → Plant Waxes “surfactant” ◼ Carnauba wax ◼ Sesame oil S.N. Sesamum indicum ✓ Obtained from co-mauba ✓ Aka Teel oil, Benne oil o S.N. Copernicia prunifera  ✓ Constituent: Mynicyl cerotate ✓ Ecuelle a piquer ◼ Jojoba oil ✓ Obtained from simmondsia chinensis ( family:buxaceae ✓ Use: Emollient ✓ Enfleurage – pomade; wax substance to obtain volatile oil in e.g. rose petals Tannins ◼ Extraction → menstruum / solvent Hydrolyzable Non-Hydrolyzable ✓ NON-POLAR solvents FeCl3 Blue ( bluish Green (greenish ◼ Enzymatic hydrolysis black) black) ✓ Myrosin Br2 No precipitate Has precipitate Myrosin ✓ Sinalbin Isothiocyanade Heat yield Pyrogallol Catechol Myrosin ✓ Sinigrin Isothiocyanade Boiled Gallic acid Phlobaphenes (ins. ◼ Distillation with HCl red compound) Type of Bloom Tameris red ✓ Water = Dried samples; sensitive to heat tannin (Turpentine oil) produced ✓ Water & Steam = Dried or fresh samples; has application of boiling (cinnamon; clove Tannins oil) ✓ Direct steam = fresh samples (spearmint; ◼ Witch Hazel peppermint) ✓ Obtained from Hamamelis virginiana ✓ Destructive = no vehicle/solvent/menstruum; ✓ Constituent: Hamamelitannin Empyreumatic oil = smoke-like; burnt-like ◼ Nutgall odor ✓ Plant: Quircus infectoria ✓ Insect: Cyvies tinctoria Hydrocarbon volatile oils o Tannic acid – most important ◼ Turpentine oil → α -pinene- present in vick’s o Elagic acid vaporub o Gallic acid ✓ Aka pine tree oil/ spirit of turpentine Volatile oils ✓ Obtained from Pinus palustris ✓ Rectified Turpentine oil (RTO) = Turpentine Aka General use oil + NaOH → stimulant expectorant. 1. Essential oils 1. Anti-septic / ✓ Terpin hydrate = RTO + HNO2. Aka 2. Ethereal oils disinfectant 2. Carminative “Terpinol” → stimulant expectorant Physical states Properties Alcohol volatile oils – ( -ol) 1. Solid = Stearoptene 1. Odoriferous (solid state of volatile 2. High refractive index Rosa gallica [rose] Geraniol oils) 3. Optically active Mentha piperita 1. Japanese PO = 2. Liquid = Oleoptene 4. Can be distilled [peppermint] Mentha Arvansis 5. Can’t be saponified 2. Contains – menthol Methods of obtaining volatile oils 3. Component of listarine ◼ Expression 4. antiseptic ✓ Sponge Coriandrum sativum S - linalool [coriander] Citrus aurantium Geraniol ; Linalool Juniperus communis Borneol Pinus palustris Torpeneol  ◼ Eucalyptus ✓ Obtained from Eucalyptus globulus Aldehyde volatile oils [-al] Ester volatile oils ◼ Lemon oil ✓ Obtained from citrus limon Gaultheria Lavender Pine needle ✓ Constituent of Citral –(o)→Teribenthianale 1. Wintergreen → Linalyl odor (do not dispense) oil acetate ◼ Cinnamon oil 2. Betula 3. Teabery ✓ Obtained from Cinnamomum cassia 4. Checkerberry ✓ Constituent: Cinnamic aldehyde Methanol + ◼ Lemongrass oil salicylic acid = ✓ Obtained from: Cymbopogon citratus methyl salicylate ✓ Constituent: Citronellal → insect repellent 5C ◼ Witch hazel oil Terpenoids -> precursor: isoprane units ✓ Obtained from Hamemelis virginiana ✓ Constituent 2-hexanal ◼ Sweet orange oil ◼ Monoterpenes (10 C) ✓ Obtained from Citrus sinensis ◼ Diterpenes (20 C) ✓ Constituent: decanal ◼ Triterpenes (30 C) ◼ Sesquiterpenes (15C) Ketone Volatile oils Monoterpenes = 2 Isoprene units Mentha spicata [spearmint] Carvone Geraniol Rose Carum carvi [Caraway] Carvone Linalool Lavender Barosma betulina [Buchu] Diosphenol Limonen Lemon Artemisia obsinthum [Wormwod] Thujone α-pinene Turpentine Cinnamomum camphora Camphor R-carvone Spearmint [Camphor] S-carvone Caraway Thuja accidentalis [Cedar leaf] Thujone Thujone Absinthe oil Thymol Thyme Nerol Orange flower Phenol Volatile oils Citronellal Lemongrass Camphor Camphor tree Thymus vulgaris [Thyme] Thymol = antifungal Eucalyptol Eucalyptus Eugenia caryophillus [Clove] Eugenol = dental analgesic Diterpenes – 4 Isoprene units Pimenta racemosa [Myecia] Juniperus oxycedrus [Cade] Creosol ✓ Taxanes Fagus grandifolia [Creosate] Guiacol ✓ Ginkolides ✓ Retinol Phenolic ether volatile oils Triterpenes – 6 Isoprene units Pimpinela anisum = Trans- methol ◼ Lanosterol Anise Ilicium verum = chinese Trans- methol star anise Tetraterpenes = 8 Isoprene units Mysristica fragans Myristicin →hallucinogen nutmeg ✓ Aka carotenaids Foeniculum vulgare Trans-methol ✓ Lycopene fennel ✓ Beta-carotene Sesquiterpens – 3 Isoprene units Oxidative volatile oil ✓ Farnesene → Green apple  ✓ Artemisinin → Kinghaosu anticancer ✓ Bisabolene → Ginger Eriodictyon Yerba Eviodictyol ✓ Zingiberene → Ginger californicum santa ✓ Prochamazulene → Chamomile Pistacia Mastic Masticnic acid lentiscus ✓ Parthenolid → Feverfew Pinus Rosin/ Abietic acid → stiffening agent Terpenoids palustris colophony ◼ Questions: ✓ Aka provitamin A = B-carotene Marijuana ✓ Aka Vitamin A = Retinol ◼ Constituent ✓ Use in the treatment of cystic acne vulgaris – o DELTA9-TCH – tetrahydrocannabinol Isotretinoin → teratogenic o CBD – cannabidiol → Therapeutic Artemisia annua 1.Artemisinin – malaria component (anti -epilepsy – infantile Qinghaosu 2.Ether: Arthemether epilepsy) 3.Esther: Artesunate o CBG cannabigerol → Analgesic Taxus brevifolia 1.Baclitaxel o CBC cannabichromeme → potency Pacific yew tree 2.MOA: Inhibit M-phase (cell enhancer division / mitosi) o Dronabinol Antiemetic; appetite stimulant Maticaria recutita 1. Labelled as Ginseng of Chamomile europe Oleoresins 2. PRochamerulene Valeriana Sleep aid Capsicum Capsacin – thermogenic officinale frutescens substance; inhibit substance P = Coleus forskohli Forskolin low pain Azadirachta indica 1. Azaderactin Zingiber Pungency (fresh):Gingerol Neem tree 2. Insect-anti-feedan officinale Pungency(cooked) Ginko biloba Menthol performance Gingerol + Baryta water(boiled) = zingerone (dementia???) Intermittent claudication Water removal from gingerol = shogaol Tanacetum Feverfew Aroma due to parthenium Bisabolene Vitamin A Betacarotene = precurser Zingiberene Isotretinoin = acne vulgaris Pinus palustris Gum thus Copaifera spp Copaiba → not true balsam Resins – Hard, Transparent, Translucent substances True balsam a. Tolu –(heat)→ soften, melt; Oxidation product of terpenes b. Peru c. Storax Oleoresins = Volatile oil Oleogumresins = Volatile d. Copaiba + Resins oil + Gum + Resins e. Benzoin Balsam = Benzoic acid Resene = Neutral and/or Cinnamic acid substances; devoid of chemical characteristics OLEO-GUM-RESINS Resinols = Resin alcohols Resinotannols = complex ◼ Myrrh resin alcohols o S.N. Commiphora molmol o Use: embalming agent; component of Resin Astring -o-sol Exogonium Jalap Jalapin (catharthic) ◼ Devil’s dung purga ; Ipurganol (purgative) o S.N. Ferula assafoetida Piper Kava-kava Methysticin (skeletal muscle o Antispasmodic methysticum relaxant) Balsams – Benzoic acid / cinnamic acid Podophyllum Mayapple/ 1. Podophyllin → antiwarts peltatum American 2. Peltatin → purgative Storax = Peru Tolu Benzoin mandrake 3. Etoposide/teniposide =Styrax Liquidambar Myroxylon M. Styrx orientalis pereirae Balsammum benzoin Expectorant parasiticide Alkaloids → basic nitrogenous compounds w/ physiologic characteristics Natural amides (R-NH2; R2-NH; R3-N) Mercuric KI Mayer’s Reagent Mercuric iodide Valser’s reagent I2 in KI Wugner’s reagent ◼ Groups Kl + BiI3 Dragendorff’s reagent o Hyoscyamine (atropine = racemate) and KI + CdI2 Marme’s reagent hyosine →scopolamine Picric acid Hager’s Reagent o Cocaine = tertiary amines = lipophilic can Phosphotungistic acid Scheibler’s Reagent enter BBB Phosphomolybdic acid Sonnenscheins reagent o Callistegine A3(no pharmacologic application Anticholinergic, reverse of dumbbells Properties DOC for physostigmine, ◼ Color white, except berberine(goldensteel) Organophosphate →yellow; sanguinrine (bloodroot) → red ◼ Solubility o Alkaloidal base: nonpolar o Alkaloidal salt: Aqueous solvent (H2O) ◼ Phase o Solid exept Scopolamine ▪ Coniine Anticholinergic ▪ Nicotine Anti motion sickness ▪ Sparteine ◼ Suffix: -ine Pyridine-piperidine Drug of abuse ◼ Betel nut / nga-nga Low NE reuptake = up NE o Obtained from Areca catechu o Rich in tannin (↑ esophageal cancer o Contains arrecoline (CNS stimulant) ◼ Tobacco o Obtained from Nicotiana tabacum o Contains Nicotine (CNS stimulant); smoking deterent? ◼ Indian tobacco Tropane Alkaloids o Obtained from Lobelia inflata Atropa belladonna Belladonna o Contains Lobeline( smoking deterrent) Withania somnifera Withania Tropane alkaloids Duboisia myopoproides Duboisa Duboisa hopwodii Pituri - Tropane ring Mandragora officinarum European Mandrake Erythroxylum coca Coca Datura stramomium Jamestown *Talumpunay = D. metel Hyoscyamus niger Henbane / Hyocyamus  ◼ Ipecac o Obtained from Cephaelis ipecacuanha Quinoline alkaloids o Constituents ▪ Cephaeline ▪ Emetine (methylated Quinoline rings cephaeline) ▪ “ipecac serum” was used in poisoning but not recommended Due to protoplasmic ◼ Cinchona bark poison o Obtained from Cinchona succirubra ◼ Curare o Constituents o Southamerican arrowhead poison ▪ Cinchonine– anti-malaria o Obtained from Stychnos castelnaei ▪ Cinchonidine– anti-malaria o Constituent Tubocurarine ▪ Quinine– anti-malaria ▪ Skeletal muscle relaxant ▪ Quinitine – anti-malaria & anti- ▪ Non – depolarizing arrythmia ▪ Decreased nAchR = Decreased o Toxicity – Cinchonism (C.M. Tinnitus) Ach activity ◼ Cuprea ◼ Goldenseal o Obtained from Remijia pedupiculato o Obtained from Hydrastis canadensis o Constituent same as cinchona o Constituents: Berberine (yellow) ▪ Antiarryhtmia (class III) Isoquinoline alkaloids ◼ Bloodroot o Obtained from Sanguinaria canadensis isoquinoline rings o Constituent: Sanguinarine (red) ▪ Cardiotoxic ▪ Possible anti cancer (unproven FDA opposed; non approved) Indole Alkaloids – indole rings ◼ Opium poppy o Obtained from Papaver somniferum o Paracelsus: stone of immortality o Morphine – pain management R1 R2 Rauvolfia serpentina Resorpine ◼ Morphine = OH OH Hypotensive -CH3 OH Psychotropic agent ◼ Codeine = Antitussive ◼ Thebaine = -CH3 -CH3 Catharanthus roseus Vincristine Periwinkle = chichirica Vinblastine ◼ Heroin = Vinorelbine - lowest neurotox All anticancer Blocks m-phase of cell Physostigma venenosum Physostigmine Calabar bean Anti glaucoma (2nd line) DOC for Atropine tox Strychnos nux-vomica Stychnine – poison with St. Ignatius bean similar action with Aka nux-vomica tetanospasmin (spastic  paralysis) ◼ Claviceps purpurea (parasitic source) – ergot fungi ◼ Claviceps paspali (Saprophytic) - rye plant o Clavine-type ▪ Ergometrine ▪ Ergotamine ▪ Ergotoxine o Lycergic acid type ▪ LSD most potent hallucinogen Imidazole alkaloid ◼ Pilocarpus jaborandi o Pilocarpine → Glaucoma; Siogren syndrome (decreased secretion)