Pharmacognosy 2 PDF

2 PHARMACOGNOSY INTRODUCTION Pharmacognosy Etymology: o Pharmakon → drugs o Gnosis → knowledge Deals with the biological, biochemical and economic features of drugs of biological origin and their constituents o Plants – Morphine...

2 PHARMACOGNOSY INTRODUCTION Pharmacognosy Etymology: o Pharmakon → drugs o Gnosis → knowledge Deals with the biological, biochemical and economic features of drugs of biological origin and their constituents o Plants – Morphine (from Papaver somniferum) o Animals – Insulin (from pancreas of pig (porcine), cow (bovine) o Microbes – Penicillin (from Penicillum notatum (old), Penicillum chrysogenum (new)) HISTORY NOTABLE PEOPLE DESCRIPTION BABYLONIANS Clay models of the human body Preliminary studies of plants → awareness of the medicinal effects of a number of plants EGYPTIANS Embalming & mummification Myrrh (oleogum resin) – mask odor of dead body George Ebers → discovered Ebers Papyrus / Papyrus Ebers in 1550 Contains: human anatomy and use of plants Made from the plant Cyperus papyrus from the Nile River HINDUS Ayurveda → Science of Life / Mother of all healing arts Ayuh - life/vital power Vedah - knowledge GREEKS Pedanios Dioscorides - “De Materia Medica” (The Medicinal Material in 5 Volumes) Describes 600+ plants Aloe, Belladonna, Colchicum, Digitalis, Ergot, Opium (ABCDEO) Claudius Galen - “Galenical Pharmacy” Father of Pharmaceutical Compounding Galenicals: Cold Cream (Galen’s cerate), Rose Water, Lanolin GERMANS Christianus Aenotheus Seydler (C.A. Seydler) – 1815 in Haale – Saale, Germany Coined “pharmacognosy” → “Analectica Pharmacognostica” Johann Adam Schmidt (J.A. Schmidt) – 1811 in Vienna First to use pharmacognosy → “Lehrbuch der Materia Medica” Friedrich August Fluckiger (F.A. Fluckiger) Most comprehensive definition of pharmacognosy Simultaneous application of various scientific disciplines with the objective of acquiring drugs from every point of view OTHERS Pierre Robiquet Codeine RobiCo Joseph Caventou & Quinine CaPeQui Pierre Joseph Pelletier (isolated) Friedrich Serturner Morphine MorSe Rudolf Brandes Hyoscyamine & Noscapine BraHyoNo Rudolf Brandes & Philipp Geiger Atropine BraGeiAt Johaness Buchner Salicin & Nicotine BuSaNi Carl Koller Cocaine KoCo Albert Hoffman Lysergic acid diethylamide (LSD) Most potent hallucinogen DEFINITION OF TERMS TERM DESCRIPTION NATURAL SUBSTANCE DIRECTLY OBTAINED from plants and animals in nature SYNTHETIC SUBSTANCE Total Synthesis → TOTALLY MADE in the LAB Semi Synthesis → STARTING MATERIALS come from NATURE INDIGENOUS PLANTS Plants growing in their NATIVE COUNTRY NATURALIZED PLANTS Plants growing in a FOREIGN LAND or LOCALITY other than their native source CRUDE DRUGS Vegetable or animal drugs that have undergone only the process of Collection and Drying EXTRACTIVES / CHIEF PRINCIPLES of crude drugs that are separated (ex. through extraction) and used DERIVATIVES in a specific manner [product of extraction] MENSTRUUM Technical term for solvent used in extraction MARC Undissolved portion of the sample APPROPRIATE SOLVENTS / MENSTRUUM CHIEF PRINCIPLE SOLVENT USED FAT Hexane RESINS & INULIN Alcohol CHLOROPHYLL Acetone CHRYSAROBIN Hot Benzene PECTIN Dilute acid SOLANINE Acetic acid 2 PHARMACOGNOSY METHODS OF EXTRACTION METHODS DESCRIPTION MACERATION / Solid ingredients are placed in a prescribed solvent for at least 3 days with frequent soaking agitation. “macerare” → to soften DIGESTION Maceration with gentle heat. PERCOLATION Use of percolator. “percolare” → to strain through Process P the rate of flow which is described as percolate slowly - 1-3 L/min comminuted drug is extracted by a slow passage of a suitable solute through a column of the drug DECOCTION Boiling in water for 15 minutes. INFUSION Maceration in cold or hot water. boiling water is added to the mixture of crude drug with water, the proportion is about 90% and then cooled PREPARATION OF CRUDE DRUGS PACKAGING, COLLECTION HARVESTING DRYING CURING GARBLING STORAGE & PRESERVATION PREPARATION DESCRIPTION COLLECTION Initial selection of the species to Pectin Small-scale cultivate unripe = protopectin Amount of constituent varies relative to ripe = pectin the season / time collected overripe = pectic acid Marijuana Best time to collect is when the Young leaves = cannabidiol constituent is at its highest content Mature leaves = cannabinol Root crops: when the ○ more addicting - THC overground parts are withering (tetrahydrocannabinol) Flowers: morning, when the Solanaceous Alkaloids (Atropine) flower just bloomed must be collected when the Bark: between summer and fruits begin to form spring HARVESTING Manual / Hand-labor Mechanical Large-scale needs skillful selection of use of machine – less labor plant parts (potent drugs) costs DRYING Reasons: Most important step 1. to fix the constituent 2. ensure good qualities 3. Removes moisture content to prevent microbial growth and enzymatic degradation CURING Enhances the property of active component Special drying process Cascara sagrada (emodin glycosides/cathartics) ○ reduced form (irritating) ○ added with MgO (alkaline earth) → oxidized form (less irritating) Vanilla splits & cuts ○ Sweating process → enhances the aroma and flavor ○ Initially dried under the sun covered in black cloth till 11 AM, retrieved and stored in a chamber, repeat the process for straight 7 days ○ Inactive constituent → Glucovanillic Alcohol ○ Active constituent → Vanillin - gives flavor and odor GARBLING Removal of extraneous materials (other plant parts, dirt, added adulterants) FINAL step PACKAGING, STORAGE, & Packaging – offer ample protection against heat and moisture PRESERVATION Storage and Preservation – to maintain high degree of quality and to prevent insect protection & marketability attacks (optional) Three ways to protect drug 1. Simplest - expose drug to 65° Celsius (insect dies) 2. Fumigation with CH3Br (methyl bromide) 3. Add a drop of CHCl3 (chloroform) or CCl4 (carbon tetrachloride) EVALUATION OF CRUDE DRUGS EVALUATION DESCRIPTION ORGANOLEPTIC / MACROSCOPIC Organs of sense (sight, smell, taste) MICROSCOPIC Micro evaluation (microscope to determine purity and identity of drug BIOLOGIC Pharmacologic activity (bioassay) CHEMICAL Determine potency (amount of chemical constituents) PHYSICAL Physical constants (optical activity: polarimeter) 2 PHARMACOGNOSY BIOASSAY DRUG ANIMAL USED MNEMONIC GLUCAGON CAT gluCATgon ATROPINE CAT CATropine OXYTOCIN CHICKEN (female, domesticated) MANOKcytosin PARATHYROID HORMONE DOGS PTHbull DIGOXIN, DIGITALIS PIGEON PIGEOxin TUBOCURARINE RABBIT & RAT 2R tubocuRaRine INSULIN RABBIT RABBINsulin HEPARIN SHEEP SHEEParin CLASSIFICATION OF CRUDE DRUGS CLASSIFICATION DESCRIPTION MORPHOLOGIC Plant part or animal part used TAXONOMIC CLASSIFICATION Natural relationship or phylogeny, history of evolution of species PHARMACOLOGIC / THERAPEUTIC Therapeutic effect CHEMICAL Preferred method, based on chemical constituents ADULTERATION OF CRUDE DRUGS Adulteration substitution of a crude drug, in whole or in part, with similarly looking substance which has lesser or no therapeutic property Sophistication Intentional addition of other components Admixture Unintentional addition of other components Substitution Entire replacement of a component Deterioration Destruction by extremes in the processing of the drug Spoilage Deterioration due to bacterial or fungal growth Inferiority Active constituent is below the minimum standard PLANT HORMONES / PHYTOHORMONES PLANT HORMONES DESCRIPTION First growth hormone discovered, from human urine Auxin Found in growing stems and roots and promotes flowering in plants Found in plant parts that are actively growing (seed embryo, stem, Major auxin in plants: young leaves) (indole-3-acetic acid) Distribution from top to bottom [IAA] Phototropism (tendency of plants to grow toward light) There are 100 kinds of this hormone. Lengthens the stem of sugarcane, hastens maturity period in group Plant Growth conifers, and promotes early seed production. Regulators Gibberellin Promotes stem/cell elongation between nodes on the stem Growth effect arises by cell elongation in the SUBAPICAL meristem where young internodes are developing Exists in areas where rapid cell division (MITOSIS) takes place and delays leaf senescence (deterioration of age), leaf enlargement Cytokinin / Kinetin Cytokinin is anti-aging component of plants. Produced in their root APICAL meristems and travel upward through water uptake via stem xylem Induces dormancy in seeds and helps seeds withstand unfavorable growth factors Abscisic acid Natural growth inhibitor that affects bud opening and seed germination Plant Growth Stomata closure Inhibitors Hastens fruit ripening and increases root growth and root hair formation, thereby, increasing their absorption surface area Ethylene Opening of flowers, ABSCISSION (shedding of leaves) Involved in rotting process 2 PHARMACOGNOSY DOH 10 HALAMANG GAMOT BABY PLANTS SCIENTIFIC NAME ACTIVE CONSTITUENT USE Bayabas Psidium guajava Tannins, Benzophene, Glycosides Astringent and antibacterial Ampalaya Momordica charantia Momordicoside Hypoglycemic agent Bawang Allium sativum Alliin, Allicin Cholesterol lowering agent Anti-dyslipidemia Yerba Buena Mentha cordifolia Putegone, Menthol, Menthene Analgesic Clinopodium douglasii Pansit-Pansitan / Peperomia pellucida Secolignans Lowers uric acid (gout) Ulasimang bato Lagundi Vitex negundo Sabinene, Nishindine Asthma and cough (Ascof, Plemex) Akapulko Cassia alata Alatinone, Chrysophanic acid, Antifungal Flavonol glycosides Niyug-niyogan Quisqalis indica Quisqualic acid Anthelmintic Tsaang-gubat Carmona retusa Epigallocatechin gallate, Antidiarrheal Ehretia microphylla Microphyllone Sambong Blumea balsamifera Limonene, Camphor, Borneol Diuretic (Re-lead Forte), Anti-urolithiasis OTHER NOTABLE PLANTS Avocado Persea americana Mangoosteen Garcinia mangostana Banaba (anti-diabetic) Lagerstroemia speciosa Moras Vetiveria zizanoides Basil Ocimum basilicum Noni berry Morinda citrifolia Damong maria Artemisia vulgaris Pandan mabango Pandanus odoratissimus Dita Alstonia scholaris Papaya Carica papaya Ipil-ipil Leucaena leucocephala Pinya Ananas comosus Kamoteng kahoy Mannihot esculenta Takip-kuhol Centella asiatica Kamyas Averrhoa bilimbi Talumpunay Datura metel Kinchay Apium graveolens Tanglad Cymbopogon citratus Wheat Triticum aestivum Tawa-tawa (dengue) Euphorbia hirta Grammatophyllum scriptium NEW FAMILY NAMES MNEMONIC OLD NEW EXAMPLES COMP-AS COMPositae ASteraceae Sunflower, Chamomile CRU-BRA CRUciferaceae BRAssicaceae Cabbage, Mustard GRA-PO GRAminae POaceae Grasses GUTT-CLUS GUTTiferae CLUSiaceae St. John’s Wort UM-API UMbilliferae APIaceae Carrot, Dill, Parsley LA-LA LAbiatae LAmiaceae Mint PAL-ARE PALmea AREcaceae Palms FAMILY NAMES MORACEAE Marijuana BUXACEAE Jojoba oil - Simmondsia chinensis (seeds) RANUNCULACEAE Goldenseal / Hydrastis ORCHIDACEAE Vanilla 2 PHARMACOGNOSY CARBOHYDRATES Hydrates of Carbon (C, H, O) General chemical formula: CnH2nOn Polyhydroxy compounds (multiple OH groups) with aldehyde or ketone functional groups o POLYHYDROXYALDEHYDES or POLYHYDROXYKETONES Most abundant organic molecules in nature 1st products of photosynthesis Functions: o Provide significant amount of energy (glucose) o Storage form of energy in the body (starch in plants, glycogen in animals) o Cell components (glycoproteins) o Structural components (chitin) CLASSIFICATION OF CARBOHYDRATES MONOsaccharide Basic sugar unit (1), simplest Crystalline/ Solids Sucrose, Fructose, Lactose Not hydrolyzed Sweet DIsaccharide 2 monosaccharides OLIGOsaccharide 3 – 10 monosaccharides Fibrous/Amorphous Starch, Cellulose POLYsaccharide > 10 monosaccharides Tasteless GENERAL PROPERTIES Physical Properties Chemical Properties Monosaccharide & Disaccharide Reducing Power White crystalline substances All mono & di contains free aldehyde or ketone group Sweet sugars Reducing sugars: o All monosaccharides Standard Sucrose/Table sugar o 2 disaccharides (ML) → Maltose, Lactose Sweetest Fructose Mutarotation Least Lactose All monosaccharides have ability to convert to dextro-levo-racemic sweet Isomerism Same molecular formula, but different structure/ arrangement Oligosaccharide & Polysaccharide Enantiomer Mirror image Non-superimposable Tasteless sugars Diastereomer Non-mirror image Epimers Same in all except 1 Carbon Starches fluffy, light amorphous Rapid interconversion of molecule due to action of alkali on powder sugars Cellulose most complex, fibrous Tautomers Tautomerization Keto-Enol Isomerism Lobry de Bryune Reaction CARBOHYDRATE PROJECTIONS To differentiate carbohydrates having same molecular formula FISCHER’S PROJECTION HAWORTH PROJECTION Vertical/horizontal representation of sugars Cyclic/ring projection of sugars Fishbone-like PYRANOSE → 6 Carbon ring FURANOSE → 5 Carbon ring CHAIR CONFORMATION Boat CONFORMATION most stable conformation of CYCLOHEXANE resembling a boat 2 PHARMACOGNOSY MONOSACCHARIDES Only 1 sugar unit, simplest and most basic, building blocks of carbohydrate Not hydrolyzed to simpler sugar CLASSIFICATION OF MONOSACCHARIDES According to Functional groups According to Number of Carbons Aldose Ketose #C Name Aldose (-ose) Ketose (-ulose) Carbonyl Carbon Carbonyl Carbon at 2 Diose Hydroxyacetaldehyde Hydroxyacetone at Position 1 Position 2 (RCOR) 3 Triose Glyceraldehyde Dihydroxyacetone (RCOH) 4 Tetrose Erythrose, Threose Erythrulose 5 Pentose Ribose, Arabinose, Xylose, Ribulose Lyxose 6 Hexose Glucose, Galactose, Fructose, Sorbose, Mannose, Allose, Altrose, Psicose, Tagatose Talose, Idose 7 Heptose Sedoheptose Sedoheptulose 8 Octose D-glycero-D- mannoctulose 9 Nonose/Sialic acid/Neuraminic acid Carbonyl Carbons (C=0) (N/O sub derivatives) Diose → smallest, simplest monosaccharide Hexose → most important monosaccharides ALDOHEXOSE (6C) GLUCOSE GALACTOSE MANNOSE Other names: C4-epimer of glucose C2-epimer of glucose Blood, Physiologic, Grape, Corn Brain sugar (Galactocerebroside) Sugar, Dextrose, for development and function of Osmotic diuretic D-glucopyranose infants for hydrocephalus Most important sugar Found in: (fluid in brain) Found in blood (60 to 90 mg/100 milk as lactose mL blood) neuronal fibers as galactosides MOST REACTIVE to Increase in diabetic patients Most rapidly absorbed from the small Ozasone/Kowarsky Test GLYCOLYSIS intestine. major metabolic pathway If not metabolized, it accumulates: Forms of Glucose: Galactosemia (brain: mental 𝛼-D-glucose retardation) for storAge polysaccharide like Cataract (eye) starch (plants) & glycogen (animals) nutrient given PO, SC, IV, & enema 𝛽-D-glucose most abundant form in nature most important for structural (Body) polysaccharide like cellulose ALDOPENTOSE (5C) KETOHEXOSE (6C) XYLOSE FRUCTOSE Wood sugar Laevulose, Fruit sugar Simplest sugar found in plants, but not in free form (Xylan Sweetest monosaccharide with bitter polymer) aftertaste Can be obtained from hydrolysis of xylan in corn cobs and Obtained from sucrose inversion straw with dilute acid. Nutrient form for DM patients (does Diagnostic aid for intestinal malabsorption and cystic not affect Blood sugar) fibrosis Ingredient in infant feeding formula RIBOSE Important sugar for genetics Product of gum hydrolysis 2 PHARMACOGNOSY DISACCHARIDES Composed of 2 monosaccharide units linked by a glycosidic bond DISACCHARIDE MONO UNITS BOND NOTES Table sugar Official sources: 1. Sugar cane → Saccharum officinarum 2. Sugar beet → Beta vulgaris 3. Sugar maple → Acer saccharum SUCROSE GLU + FRU Alpha 1, 2 Uses: Demulcent → Simple syrup NF: 85% w/v, Nutrient Preservative → Bacteriostatic at 85°C (self-preserving) Sweetening agent → masks disagreeable taste Only disaccharide that occurs free in nature TREHALOSE Alpha 1, 1 From Ergot and Yeast Malt sugar (Malted grain: from germination of barley) MALTOSE Alpha 1, 4 Beer sugar (sugar found in energy drink) GLU + GLU Product of COMPLETE or MAJOR hydrolysis of starch SOPHOROSE Beta 1, 2 CELLOBIOSE Beta 1, 4 Plants Milk sugar (Cow’s milk: Bos taurus), Tautomers LACTOSE GAL + GLU Beta 1, 4 Used as tablet diluent and infant feeding Alkaline lactose, Heated milk Tautomers (product of alkaline rearrangement of lactose) o Glucose of lactose is converted to Fructose Use: Stimulant laxative (Duphalac, Lilac ®) o To reduce straining of defecation for MI patients o MOA: Accumulation of Acetic acid & Lactic acid LACTULOSE GAL + FRU Beta 1, 4 increases peristalsis/contraction due to GI irritation o Acids are metabolized by bacterial colon Treatment of hyperammonemia o Hepatic encephalopathy (altered brain sensorium) o Lactulose will be fermented by gut bacteria to liberate H+ ion. Then, Ammonia + H+ → NH4+ (readily excreted from the body via stool) GLYCOSIDIC BOND bond that connects 1 monosaccharide to another forming DI-, OLIGO-, and POLY-saccharide o Alpha → DOWN Oxygen o Beta → UP Oxygen MILK PRODUCTS DESCRIPTION CREAM Formed when milk is allowed to stand for a few hours, then the fat globules rise to the top. BUTTER Formed when FAT GLOBULES UNITE BUTTER MILK Liquid LEFT after fat globules unite. SKIMMED MILK Milk left AFTER SEPARATION OF CREAM. COAGULUM Formed when skimmed milk is treated with RENNIN. CHEESE TREATED COAGULUM WHEY Liquid SEPARATED from the coagulum, contains lactose and inorganic salts CONDENSED MILK Formed by partial evaporation of milk in a vacuum with consequent sterilization in hermetically-sealed container by autoclaving. MALTED MILK Evaporation of milk with MALT EXTRACT. KUMYSS FERMENTED milk. 2 PHARMACOGNOSY OLIGOSACCHARIDES 3-10 monosaccharide units TRISACCHARIDES DESCRIPTION DEXTRIN Several repeating glucose units, responsible for browning of bread MALTOTRIOSE Glu + Glu + Glu INTERMEDIATE product of starch hydrolysis. GENTIANOSE Glu + Glu + Fru 2 Glu is to Fraste (Gents) MELIZITOSE Glu + Fru + Glu Si Melai may 2 sweet girls with FRancisco PLANTEOSE Glu + Fru + Gal GirLU be Frugal sa plants RAFFINOSE Gal + Glu + Fru Galanteng Glutton Friend TETRASACCHARIDE STACHYOSE 2 Gal + Glu + Fru PRODUCTS OF STARCH HYDROLYSIS LIQUID GLUCOSE INCOMPLETE product of starch hydrolysis. DEXTRIN PARTIAL product of starch hydrolysis. MALTOTRIOSE INTERMEDIATE product of starch hydrolysis. MALTOSE COMPLETE or MAJOR product of starch hydrolysis. POLYSACCHARIDES > 10 monosaccharides (up to thousands) (large MW, bioMACROmolecules) HOMOGLYCAN HETEROGLYCAN Only 1 type of monosaccharide (Homopolysaccharide) 2 or more components (Heteropolysaccharide) Same type of sugar units Different types of sugar units Glucan/Glucosan Fructan/Fructosan Ex. Glucose + Fructose + Arabinose = (mixed) 1. Starch 5. Inulin 1. Gums 2. Glycogen 6. Chitin 2. Mucilage 3. Dextran 7. Pectin Glycosaminoglycans/Mucopolysaccharides (GAGs) 4. Cellulose GLUCAN/GLUCOSAN Yields glucose upon hydrolysis STARCH Energy-storage polysaccharide in plants Uses: (primary reserve CHO in plants) Tablet filler, binder and disintegrant Temporary storage form of Antidote for iodine poisoning (starch suspension) photosynthetic products (glucose) in Permanent reserve food material in plants plants Two components of starch: Most widely distributed organic Note: Iodine test → identification test for starch compound in plants AMYLOSE (25%) AMYLOPECTIN (75%) Official sources: Linear (spiral/helix) Linear Branched (every 25-30 1. Corn (Zea mays) 𝛼 1,4 𝛼 1,4 units) 2. Potato (Solanum tuberosum) 𝛼 1,6 3. Wheat (Triticum aestivum) Water Soluble Water Insoluble (less soluble) 4. Rice (Oryza sativa) 250 – 300 units > 1000 units Alternative source: Dark/Deep blue complex in Purple/Violet/Red-brown in Iodine Arrowroot (Maranta arundinaceae) Iodine Enzymes that breakdown starch: B – amylase → pancreatic juice and saliva (both, CHO digestion – mouth) A – amylase → hydrolyzes it to maltose (only in pancreas, biomarker) Starch products of metabolism: STARCH PASTE Dispersed starch in cold water. Used as a binder in solution (5-10% starch) ○ Acetaminophen tablet PREGELATINIZED STARCH All the granules have been ruptured in the presence of water SODIUM STARCH GLYCOLATE Semi-synthetic sodium salt of carboxymethyl ether of starch used as a disintegrant 6% w/v HETASTARCH (VOLUVEN) / Water-soluble starch with > 90% amylopectin HYDROXYETHYL STARCH Plasma expander in shock patients. GLYCOGEN 𝜶 1,4, 𝜶 1,6 Animal starch Major form of stored carbohydrate in animals Storage polysaccharide in animals Stored in liver and skeletal muscles More branched than starch (every 8 – 10/12 - 15 units) 2 PHARMACOGNOSY DEXTRAN α-1,3, α-1,6 10% Plasma expander in shock patients. Obtained through the action of dextran sucrase from Leuconostoc mesenteroides Sucrose –dextran sucrase→ Dextran CELLULOSE β-1,4 Main structural component in plant cell wall Chief constituent in plant cell walls Made up of cellobiose (beta-1,4) Source: Seed of Cotton (Gossypium hirsutum) Cellulose Products: PURIFIED COTTON From the hair of the seeds of Gossypium hirsutum. Used as surgical dressing. POWDERED CELLULOSE Mechanically disintegrated alpha cellulose Purity → solubility in sulfuric acid ○ Insoluble 𝛼 cellulose ↑ quantity of 𝛼 cellulose, ↑ quality MICROCRYSTALLINE CELLULOSE Purified, partially depolymerized alpha cellulose, disintegrant PURIFIED RAYON Bleached, regenerated cellulose with NMT 1.25% of titanium dioxide Cellulose Derivatives: METHYLCELLULOSE Used in ophthalmic solutions as thickener. (M - MATA) ETHYLCELLULOSE Tablet binder, film coating (E-BIND) HYDROXYETHYLCELLULOSE Thickener, ingredient in artificial tears HYDROXYPROPYL METHYLCELLULOSE Free-flowing powder commonly used to provide hydrophilic matrix (HPMC) for extended-release (ER) tablets. PYROXYLIN / Made by the action of nitric and sulfuric acid on cellulose. CELLULOSE TRINITRATE / SOLUBLE A pharmaceutic aid used in the preparation of collodion and flexible GUNCOTTON / NITROCELLULOSE collodion. (COLLODION/FLEXI COLLODION) ○ Collodion - 1% alcohol + 3% ether ○ Flexible collodion 1% alcohol + 3% ether + 3% castor oil → flexibility + 2% camphor → waterproof Exceedingly flammable. CELLULOSE ACETATE PHTHALATE (CAP) Present in both Enteric and Film coating of tablets. (CAPEF) SODIUM CARBOXYMETHYL CELLULOSE Suspending agent (S-SODIUM-SUSPENDING) Bulk laxative FRUCTAN/FRUCTOSAN Yields fructose upon hydrolysis INULIN Obtained from the cell sap of the underground organs (tubers) of the plants in the family Compositae (𝜷-2,1 bonds) Source: Chicory root (Chicorium intybus) Uses: 1. improves digestion; 2. ingredient in culture media; 3. measure glomerular filtration rate (GFR) for kidney function (not secreted nor reabsorbed) CHITIN Exoskeleton of mollusks, arthropods, crustaceans and fungi. Homoglycan of N-acetylglucosamine Hydrolytic product: Acetylglucosamine Galactoronic acid is found in Chitin but not in Cellulose (structural polysaccharide) PECTIN General term for a group of polysaccharide present in the cell wall Intercellular cementing material Obtained from the dilute acid extract of the inner portion of the rind of CITRUS fruits or pomace More stable in COLD ACID SOLUTION Contains a partially methoxylated galacturonic acid (responsible for its swelling property) Kaopectate (Kaolin + Pectin) (Bismuth subsalicylate) – vs. diarrhea & upset stomach 2 PHARMACOGNOSY PRODUCTS OF OXIDATIVE METABOLISM OF CARBOHYDRATES PRODUCTS IUPAC NAME DESCRIPTION From the fresh ripe cherry fruits (Prunus cerasus). 2-hydroxybutanedioc CHERRY MALIC Contains > 1% malic acid acid JUICE ACID Used to prepare cherry syrup. (2HBdioc) Indirect permanganate oxidation method Tricarboxylic acid discovered from lemon juice (Citrus limon) by Carl Wilhelm Scheele. 2-hydroxypropane-1,2,3- CITRIC Antidote for NaOH poisoning tricarboxylic acid ACID Efflorescent, component of effervescent granules (2HPtricarbo) (acidulant) If given alone = sticky PLANT Byproduct of wine industry. ACIDS TARTARIC 2,3-dihydroxybutanedioc Dicarboxylic acid ACID (23DHBdioc) Acidulant in effervescent salts and refrigerant drinks If given alone = crumble easily/loose granules From lactic fermentation of sugars LACTIC 2-hydroxypropanoic acid Acidulant in infant feeding formula ACID (2HPropa) Acid responsible for formation of dental carries produced during vigorous exercise (lactate) 95% ethanol by volume at 15.56°C Product of fermentation or distillation ALCOHOL / Beer → fermentation of WINE BRANDY, WHISKEY, RUM ETHANOL Brandy → distillation of WINE Whiskey → distillation of MALTED GRAIN Rum → distillation of FERMENTED MOLASSES PRODUCTS OF REDUCTIVE METABOLISM OF CARBOHYDRATES PRODUCTS DESCRIPTION MANNITOL Source: Manna (Fraxinus ornus), dried saccharine exudate (Mannose → Mannitol) IV - osmotic diuretic PO – laxative Diluent in chewable tablets Used to treat increase ICP (intracranial pressure) SORBITOL / D-GLUCITOL Source: Berries of Mountain ash (Sorbus aucuparia) (Glucose → D-glucitol) Plasticizer in soft gelatin capsule Accumulates in the body (lenses of eyes) → cataract Approximately HALF AS SWEET as sucrose/sugar Humectant → attracts and hold onto H2O to keep things moist Ingredient in toothpaste, cream, chewing gum, dietetic product TESTS FOR CARBOHYDRATES 2 PHARMACOGNOSY GUMS, MUCILAGE, AND PLANT EXTRACTIVES GUMS MUCILAGES Readily soluble in H2O Forms slimy masses with H2O Pathologic product - human intervention Physiologic product - natural injuries Use: Laxative Use: Suspending agent GUMS AND MUCILAGES Natural Plant Hydrocolloids that yield sugar upon hydrolysis (Arabinose, Galactose, Glucose) Maybe classified as ○ Anionic or non - ionic ○ Salts of polysaccharide (Linear or branched) Linear - less soluble, less stable, viscosity enhancer Branched - more soluble, more stable, gelating/gelling agent Appears as translucent and amorphous substances produced by plants post-injury Precipitate with lead acetate and alcohol Can be classified as: 1. PLANT (SHRUB OR TREE) EXUDATES (KATI) 2. MARINE GUMS (ACAD) 3. SEED GUMS 4. MICROBIAL GUMS (XD) 1. SHRUB OR TREE EXUDATES PLANT SCIENTIFIC ACTIVE CONSTITUENT DESCRIPTION NAME Has fetid odor (amoy tae) Karaya / D-galacturonic acid D- Suspending agent 1 Sterculia urens Sterculia Gum glucuronic acid Present in laxative (Movicol®) ○ Karaya + Frangula 35 - 38% used as a dispersion or suspending agent in water Acacia / Stable below 60% alcohol, contains 12-15% 2 Gum Arabic / Acacia senegal Arabin water Egyptian Gum Insoluble and immiscible True emulsifier 5 – 6% used as a dispersion or suspending 66% BASSORIN agent in water (swelling) Astragalus Best used as tablet binder when dry as it 3 Tragacanth gummifer forms heavy mucilage in water (Best 34% TRAGACANTHIN mucilage) (thickener) Resistant to hydrolysis Ghatti / Indian Anogiessus Substitute for Acacia 4 Gum latifolia FORMS OF TRAGACANTH TYPE SOURCE SHAPE COLOR VERMIFORM Natural injuries Worm-like, Twisted into coils Yellow-brown TRAGACANTH SORTS Natural injuries Irregular, Tear shaped Yellow-brown Man-made transverse RIBBON & FLAKES Ribbon, Flakes Clear → preferred / BEST grade incision 2. MARINE GUMS PLANT SCIENTIFIC NAME ACTIVE DESCRIPTION CONSTITUENT Purified carbohydrate extracted from BROWN SEAWEEDS using dilute alkali Algin / Fucoidan – from brown algae; 1 Macrocystis pyrifera D-mannuronic acid Sodium alginate treatment of herpes simplex virus Suspending agent Tablet binder Carrageenan / Kappa → stable helix, Brittle gelling Chondrus crispus Demulcent 2 Chondrus / Iota → stable helix, Elastic gelling Gigartina mamillosa Bulk laxative Irish Moss Lambda → not stable, non-gel, Thickener Laxative Agar / Gelidium cartilagineum Agarose (no SO4) 3 Tablet diluent and disintegrant Japanese isinglass Gracilaria confervoides Agaropectin (w/ SO4) Solidifying agent in culture media Danish agar / 4 Furcellaria fastigiata Similar to carrageenan Suspending agent (red algae) Furcellaran 2 PHARMACOGNOSY 3. SEED GUMS PLANT SCIENTIFIC NAME ACTIVE CON. DESCRIPTION Plantago / Plantain seed / SPANISH: Plantago psyllium Ripe seed coat is used as bulk 1 Psyllium INDIAN: Plantago ovata forming laxative L-arabinose Thixotropic (texture changing; easy 2 Cydonium / Quince seed Cydonia vulgaris Aldobiuronic acid application) hydrocolloid in lotions. Bulk laxative Cyamopsis 3 Guar guam / Guaran Galactomannan Thickener tetragonolobus Disintegrant Locust bean gum / Used as CHOCOLATE substitute 4 Caro-b pulp / Ceratonia siliqua Galactomannan Thickener St. John’s bread Stabilizer 4. MICROBIAL GUMS PLANT SCIENTIFIC NAME DESCRIPTION PSEUDOPLASTIC / SHEAR THINNING FLOW allows toothpastes and ointments to hold shape and spread 1 Xanthan Gum Xanthomonas campestris easily. High MW gum from the action of X. campestris on a suitable carbohydrate 2 Dextran Gum Leuconostoc mesenteroides PLASMA EXPANDER TERMS TO REMEMBER EUDISTAMINES B-carboline derivatives isolated from sponges (Subphylum Tunicata). Sulfated polysaccharide compound extracted from brown algae Laminaria spp. active FUCOIDAN against Herpes Simplex Virus. ALGIN Purified carbohydrate extracted from brown seaweed by treatment of dilute alkali. A polysaccharide obtained from red seaweed used in preparation of toothpaste as CARRAGEENAN emulsifying agent. PLANT EXTRACTIVES Pectin Intercellular cementing material General term for a group of polysaccharide present in the cell wall Obtained from the dilute acid extract of the inner portion of the rind of CITRUS fruits or pomace More stable in COLD ACID SOLUTION Contains a partially methoxylated galacturonic acid (for swelling) Constituents present: ○ Unripe = Protopectin ; Ripe = Pectin ; Overripe = Pectic Acid Kaopectate (Kaolin + Pectin) (Bismuth subsalicylate) – vs. diarrhea PLANT SCIENTIFIC NAME POMELO Citrus GRANDIS (GRAND = MAHAL ANG POMELO) ORANGE Citrus SINENSIS DALANGHITA Citrus NOBILIS (MABILIS ANG MATA NG LALAKI KAPAG MAY DALANG HITA) PONKAN Citrus RETICULATA KALAMANSI Citrus MICROCARPA (micro=small=kalamansi) GRAPEFRUIT Citrus PARADISI (LIFE IS A PARADISE KAPAG MAY GRAPES) LEMON Citrus LIMON APPLE POMACE MALUS DOMESTICA (APPLE IS A DOMESTIC WORKER) GLYCOSAMINOGLYCANS (GAGS) / MUCOPOLYSACCHARIDE Vitreous (eye) humor, synovial fluids Spreading factor (makes skin tensile and more elastic) HYALURONIC ACID Anionic NONsulfated glycosaminoglycan Distributed widely via connective, epithelial (MOST PREDOMINANT), & neural tissues component of the group A streptococcal extracellular capsule Cartilage, tendons, & ligaments SULFATED GLYCOSAMINOGLYCAN composed of a chain of alternating sugars (N- CHONDROITIN acetylGALactosamine and GLUCoronic acid) SULFATE structural component of CARTILAGE, provides resistance to compression Treatment of OA (Osteoarthritis) DERMATAN SULFATE Skin Nails, Cornea (most predominant) KERATAN SULFATE Does not contain uronic acid Found in connective tissue (bones), epithelial tissue (skin) HEPARAN SULFATE Basement membrane of cells HEPARIN Mast cells, liver, lung, skin Generalization: All GAGs are sulfated except for hyaluronic acid. All GAGS contain uronic acid except for keratan sulfate 2 PHARMACOGNOSY GLYCOSIDES Yield one or more sugar among the products of hydrolysis Acetals in which the OH group of the sugar portion is condensed with the OH group of the non-sugar portion Linked by a Sugar-Ether bond Both alpha and beta glycosides are possible, but only BETA forms occur in plants / most common Parts Component Test (+) Result GLYCONE Sugar, inactive 2-deoxy sugar group Liebermann-Burchard Test Blue-green complex Test for lipids Salkowski Test Red color at the junction AGLYCONE / Non-sugar, Unsaturated steroidal Keller-Killiani Test Reddish brown GENIN Active nucleus (CPPP) Aglycone Cardenolide Bufadienolide More common Less common, from toad skin (Bufo spp.) C23, 5-membered lactone ring C24, 6-membered lactone ring Optimum activity Less activity Classes of Glycosides: 1. Cardiac Glycosides 2. Anthraquinone Glycosides 3. Saponin Glycosides 4. Cyanophore Glycosides 5. Isothiocyanate Glycosides 6. Flavonol Glycosides 7. Alcohol Glycosides 8. Aldehyde Glycosides 9. Phenol Glycosides 10. Lactone Glycosides CARDIAC GLYCOSIDES Exert action on cardiac muscle MOA: Inhibits Na/K/ATPase pump o Increased intracellular Na+ (3 units) o Decreased intracellular K+ (2 units) o Reduction of Ca2+ expulsion (increased intracellular Ca2+) ▪ (+) inotropic = Inc. cardiac contractility ▪ (-) chronotropic = Dec. heart rate PLANT ORIGIN ACTIVE CONSTITUENT 1 Grecian Foxglove Digitalis lanata Digoxin (H2O soluble), less toxic 2 Foxglove Digitalis purpurea Digitoxin (lipid soluble), more toxic 3 Convallaria / Lily of the Valley Convallaria majalis Convallatoxin 4 Adonis / Pheasant’s Eye Adonis vernalis Adonitoxin 5 K-strophantin Strophantus Strophanthus kombe G-strophanthin (ouabain) → toxic 6 Apocynum / Dogbane / Black Indian Hemp Apocynum cannabinum Cymarin 7 Oleander / Adelfa / Rose Bay Nerium oleander Oleander 8 Scillarenin → the only bufadienofide Squill / Mediterranean / White Squill Urginea maritima Should not have red moiety (very toxic) 9 Cactus grandifloras / Night Blooming Selenicereus Cactus grandiflorus 10 Black hellebore Helleborus niger Hellebrin → cardiac stimulant 2 PHARMACOGNOSY ANTHRAQUINONE GLYCOSIDES Aglycone portion: ANTHRACENE RINGS Commonly employed as Drastic Cathartics ○ EXCEPT: Chrysarobin (dissolve in HOT benzene) Color of anthraquinone derivatives: Orange Identification test: BORNTRAGER’S TEST PLANT ORIGIN ACTIVE CONSTITUENT Cascaroides AB: optical isomer of Barbaloin CD: optical isomer of Chrysaloin Bark aged for 1 year Cascara Sagrada / 1 Rhamnus purshianus treated with MgO to mask bitter Sacred Bark taste Lane’s Pill contains Casanthrol (purified mixture of anthranol glycosides) Frangula / Buckthorn Frangulin (Karaya + Frnagula) → Movicol® 2 Rhamnus frangula Bark Barbaloin CURACAO: CAPE: Management of burn wounds, Dried Latex Juice of 3 Aloe barbadensis Aloe spicata moisturizer Leaves Aloe vera Aloe ferox Component of CBT (Compound Benzoin Ticture) CHINESE: INDIAN: Rhein anthrones (dried rhizome or root) 4 Rhubarb Rheum officinale R. emodi Rheum palmatum R. webbianum Sennosides A and B Cultivated in wet-lands resembling TINNEVELLY: ALEXANDRIA: rice-paddies 5 Senna Cassia angustifolia Cassia acutifolia More potent than Cascara sagrada (full leaves) (broken leaves) Best grade: Blue-Green / Emerald Green Worst grade: Yellow green Chrysarobin → Keratolytic (psoriasis) Very irritating to mucous Goa / Araroba / Bahia 6 Andira araroba (Goa powder) membranes powder Extracted using hot benzene Replaced by Anthralene SAPONIN GLYCOSIDES Bitter acrid taste Soap-like (form colloidal solutions that foams upon shaking) Steroidal in nature (CPPP nucleus) Sternutatory (irritating to mucous membrane) Aglycone portion: SAPOGENIN Toxic aglycone: SAPOTOXIN ○ Destroy RBC of cold-blooded animals (fish-poison) → CAPILLARY TUBE TEST ○ (+) B-hemolytic test (complete hemolysis) → HEMOLYSIS TEST Types of Saponins ○ Neutral Saponins: with SPIROKETAL side chains (Diosgenin) ○ Acid Saponins: with TRITERPENOID structures (Ginsenoside) TESTS FOR SAPONIN GLYCOSIDES TEST POSITIVE RESULT FROTH TEST Persist for 10 minutes KELLER KILLIANI TEST Reddish brown (test for glycone portion) LIEBERMANN-BURCHARD Blue-green PLANT ORIGIN ACTIVE CONSTITUENT Glycyrrhizin / Glycyrrhic acid 50x as sweet as sugar Mask Quinine’s bitterness Increase foaminess of beer Imparts bitter taste to root beer Expectorant, Demulcent (relieves mucosal inflammation & Licorice Root / 1 Glycyrrhiza glabra irritation) Glycyrrhiza Treatment of Addison’s disease and PUD (Peptic Ulcer Disease) Glycyrrhetinic acid Hydrolytic product of glycyrrhizic acid Contraindicated: CHF, HTN (Na/H2O retention) 2 PHARMACOGNOSY Dioscorea / Dioscorea floribunda Diosgenin & Botogenin 2 Mexican Yam Dioscorea spiculifora Best source / Major precuror for steroid synthesis (glucocorticoids) Panaxosides, Ginsenosides, Chikusetsusaponins AMERICAN: Favorite remedy in Chinese medicine Panax quinquefolius ○ Aphrodisiac (increase sexual drive/libido) 3 Ginseng ASIAN: ○ Adaptogen (anti-stress) Panax ginseng ○ Tonic Increase risk of bleeding if taken with Aspirin (anti-platelet) Smilaginin 4 Sarsaparilla Smilax spp. Steroid sapogenin CYANOGENIC GLYCOSIDES Cyanogenic: produces CYANIDE upon hydrolysis (hydrocyanic acid: HCN) ○ MOA: inhibits cytochrome oxidase (complex IV in the Electron Transport Chain) Found in ROSACEAE plants Identification test: GUIGNARD TEST / PRUSSIC ACID TEST ○ (+) various shades of RED Cyanide-containing compounds: ○ LAETRILE / VIT. B17 → was used for the treatment of sickle cell anemia (banned by US FDA) ○ PRUNASIN ○ AMYGDALIN (most common source) Enzymes: Amygdalase + Prunase = Emulsin PLANT ORIGIN ACTIVE CONSTITUENT 1 Bitter Almond Prunus amygdalus Amygdalin 2 Apricot Prunus armeniaca 3 Wild Cherry Prunus serofina Prunasin 4 Peach Prunus persica 5 Cassava Mannihot esculenta Manihotoxin 6 Flax Linum usitatissimum Linamarin ISOTHIOCYANATE GLYCOSIDES AKA: GLUCOSINOLATES or MUSTARD GLYCOSIDES Found in cruciferous plants Uses: local irritant, emetic, rubefacient, vesicant, condiment BLACK MUSTARD WHITE MUSTARD RAPESEED OTHER NAME Sinapis nigra Sinapis alba SCIENTIFIC NAME Brassica nigra Brassica alba Brassica napus ACTIVE CONSTITUENT Sinigrin Sinalbin Gluconapin FLAVONOL GLYCOSIDES Aglycone portion: FLAVONOIDS Polyphenolic compounds (↑ Phenol = ↑ H2O solubility / polarity) PLANT SCIENTIFIC NAME ACTIVE CONSTITUENT USE 1 Vitamin P Permeability factor Rutin + Hisperidine To treat capillary fragility & bleeding Buckwheat Fagopyrum Rutin Yellow pigment 2 plant esculentum 3 Elm Ulmus spp. Quercetin Yellow pigmnent 4 Milk thistle Silybium marinum Silymarin Hepatoprotective (liver) 5 Ginkgo Ginkgo biloba Gingkolides & bilobides Memory enhancement Hesperitin, Diosmin, Treatment of common cold 6 - Naringen symptom 2 PHARMACOGNOSY ALCOHOL GLYCOSIDES SOURCES ORIGIN ACTIVE USE 1 Poplar bark Populus spp. Populin 2 Willow bark Salix purpurea Salicin Anti-rheumatic, anti-inflammatory Salix fragilis same as SALICYLIC ACID (o-hydroxybenzoic acid) Hydrolyzed to SALIGENIN (Salicyl alcohol) and D-glucose by emulsin. ALDEHYDE GLYCOSIDES SOURCES ORIGIN ACTIVE CONSTITUENT USE Flavorant Semi-synthesized from: Vanillin VANILLA Vanilla planifolia Coniferin (4-hydoxy-3-methoxybenzaldehyde) Eugenol Lignin Preparation of Vanilla Pods (BEQ) 1. The plant is usually propagated by means of cuttings. After 2 or 3 years, it reaches the flowering stage and continues to bear fruit for 30 to 40 years. 2. Ripe yellow fruits are collected. 3. The pods are cured by dipping in warm water and repeated sweating between woolen blankets under the sun during the day and packing in wool-covered boxes at night. 4. The pods are then graded, tied into bundles of about 50 – 75, and sealed in tin containers for shipment. TYPE OF VANILLA DESCRIPTION Mexican / Vera Cruz Vanilla Best-grade vanilla Bourbon Vanilla Blacker with coumarin odor Tahiti & Hawaii Vanilla Red-brown with unpleasant odor Green Vanilla Inactive Form PHENOL GLYCOSIDES SOURCES ORIGIN ACTIVE USE Uva-ursi / Arctostaphylos uva-ursi Arbutin / Ursin Mild diuretic (present in teas) 1 Bearberry Causes contact dermatitis (TYPE B ADR) - TYPE IV Hypersensitivity “T-cell Poison ivy Rhus radicans 2 Uroshiol mediated / Delayed” Poison oak Rhus toxicodendron - After 3 to 5 days 2 PHARMACOGNOSY LACTONE GLYCOSIDES SOURCES ORIGIN ACTIVE CONSTITUENT USE 1 Tonka beans Dipteryx odorata Anticoagulant (DUGO!!!) Sweet vernal Anthoxanthum Coumarin 2 (Bishydroxycoumarin / grass odoratum Precursor of Warfarin Mellitus albus Dicumarol) “Winconsin Alumni Research 3 Sweet clover Mellilotus officinalis Foundation” Sweet-scented 4 Galium triflorum bedstraw 5 Red clover Trifolium pratense Use: Irritant Vesicant Catharidin Aphrodisiac (from mature insect with Wart-removal green metallic luster) If taken internally, 6 Cantharides Cantharis vesicatoria it is excreted by the kidney, Russian / Spanish / irritates the urinary tract, Blister fly resulting to PRIAPISM. Insects are killed with fumes of: Hot vinegar NH3 Chloroform Photosensitizing furocoumarins Psoralens When applied to skin & exposed to sunlight, ↑ risk of sunburn Derivative of Psoralen Ammi majus Repigmentation of VITILIGO 7 Bishop’s flower Methoxsalen Xanthotoxin (8-methoxylsoralen) Trioxsalen Synthetic furocoumarin 8 Wormseed Artemisia cina Santonin Anthelmentics 9 Blackhaw Viburnum prunifolium Scopoletin Antispasmodics 2 PHARMACOGNOSY TANNINS Group of complex phenolic compounds capable of combining with proteins Has acidic, puckering taste (mouth feels rough/dry) Difficult to separate but they do not crystallize. Precipitate alkaloids, proteins, and glycosides. Found in universal antidote: 211 ATM (2 activated charcoal, 1 tannic acid, 1 MgO) Medicinal use: ○ Astringent → decrease pore in face ○ Treatment of burns ○ Antidote for alkaloidal poisoning Industrial use: ○ Manufacture of leather from animal hides TEST PSEUDOTANNINS TRUE TANNINS POSITIVE RESULT GELATIN TEST   Precipitation of proteins GOLDBEATER TEST   Brown or black protein precipitate PHENAZONE TEST Bulky colored protein precipitate CLASSES OF TANNINS SOURCES HYDROLYZABLE NON-HYDROLYZABLE Heating Gallic acid → Pyrogallol Catechol Properties Pyrogallotannins Condensed / Proanthocyanidins / Phlobotannins Easily hydrolyzed X hydrolyzed + Sugar moiety X sugar moiety Hydrolyzation Boil with HCl Phenolic acid w/ sugar Phlobaphenes (red, insoluble polymerization product) Ferric Chloride (FeCl3) Test Bluish-black ppt Greenish-black ppt (Tannin, Flavonol Glycoside) Buff-colored ppt Bromine Water No ppt (-) Precipitate Lead Acetate Soluble Insoluble (-) Leather Type Bloom Tanner’s red Potassium Permangate Decolorizes Does not decolorize SOURCES OF TANNINS PLANT ORIGIN ACTIVE USE CONSTITUENT Quercus infectoria Tannic acid / Astringent Young twigs, hardened excrescence by Gallotannic acid Most important source of 1 Nutgall hymenopterous insect Cynips tinctoria tannins which bores holes to deposit its ova Ellagic acid + Gallic acid = Tannic acid Hammamelis Leaf Hamamelis virginiana Hamamelitannin Astringent 2 / Witch Hazel Antihemorrhoidal prep. Chewing Betel Areca catechu Pseudotannins Carcinogenic potential 3 Nut (oral/esophageal cancer) 4 Tea without Milk Camelia sinensis 2 PHARMACOGNOSY LIPIDS Esters of long-chain fatty acids & alcohols (Lipoids/Lipins) General uses: ○ Emollients (soften the skin) ○ Lubricant laxatives as emulsions ○ Solvents for IM injections (PeCotSeCorn) ○ Manufacture of soaps (Saponification/Alkali-catalyzed esterification of FA = FA + KOH/NaOH) ○ Parenteral nutrient in TPN (highest caloric value = 9 kcal/g) CLASSIFICATION OF LIPIDS FIXED OILS FATS WAXES DESCRIPTION Esters of FA + Glycerol Esters of FA + High MW alcohol Aka. Triglycerides (Cetyl alcoholol, Stearyl Alcohol) PHYSICAL Liquid at Room Temp. except Solid at Room Temp. except Solid or semi-solid except STATE Myristica Cod liver oil Jojoba oil Theobroma oil COMPOSITION Mainly UNSATURATED FA Mainly SATURATED FA BOTH saturated & unsaturated (pi-bonds) (sigma bonds) SOURCE Plants Animals Plants & Animals FUNCTION Energy source Protection REACTION WITH LIPIDS 1. HYDROGENATION: ○ Liquid oil → Solid fats ○ Addition of Water → breaks down to ALCOHOL + FATTY ACID ○ By passing H gas in presence of Nickel / Palladium through the oil heated @ 160-200C 2. HEATING ○ Continuous heating of oil forms ACROLEIN/PROPENAL (presence of glycerol, formation of propenal) ○ Distinct odor of acrolein ○ Black markings in filter paper → confirm presence of acrolein 3. SULFATION: ○ Sulfated / Sulfurated oils ○ Used as surfactants wherein temperature is kept down by chilling 4. OXIDATION: ○ Addition of Oxygen → Rancidity (fats become rancid/panis) 5. SAPONIFICATION → formation of soap ○ Fatty acid + Strong alkali NaOH, Ca(OH)2 → hard soap KOH → soft soap USP QUANTITATIVE TESTS FOR LIPIDS Acid value / number no. of mg of KOH to NEUTRALIZE the free acids and to HYDROLYZE THE ESTERS in 1 g of the substance Ester value mg of KOH needed to SAPONIFY 1g of FA DIFFERENCE between SV and AV (saponification value- acid value) Ester Value Formula: EV = SV - AV Saponification value no. of mg of KOH needed to NEUTRALIZE the FREE ACIDS and SAPONIFY THE ESTERS in 1 g Koettsdorfer number of the substance. Saponification Value Formula: SV = AV + EV Iodine value g of iodine absorbed under prescribed conditions by 100 g of sample Measures the DEGREE OF UNSATURATION of the oil (↑ unsaturation, ↑ drying)  High iodine value are those which partially resinify on exposure to air IODINE VALUE EXAMPLES Non-drying < 100 OPA Olive oil, Peanut oil, Almond oil Hazelnut oil, Cocoa butter, Palm oil, Fish oil, Tree oil Semi-drying 100 - 120 CotSeCorn Cottonseed oil, Sesame oil, Corn oil Soybean oil, Sunflower oil, Safflower oil, Mustard oil Drying (painting) > 120 LiCod Linseed / Flaxseed oil, Cod liver oil Acetyl value no. of mg of KOH required to NEUTRALIZE the ACETIC ACID freed by the hydrolysis of ACETYLATED fat or other substances Peroxide value no. of mg of ACTIVE OXYGEN per kilogram of a substance 2 PHARMACOGNOSY FATTY ACIDS SATURATED FATTY ACIDS MONOCARBOXYLIC FA # of C Trivial Name Systematic Name Notes 1 Formic Methanoic 2 Acetic Ethanoic 3 Propionic Propanoic 4 Butyric Butanoic 5 Valeric Pentanoic 6 CaprOic Hexanoic O 7 Enenthic Heptanoic 8 CaprYlic Octanoic Y 9 Pelargonic Nonanoic 10 CarprIc Decanoic I (CaLaMyPaStAr) 12 Lauric Dodecanoic 14 Myristic Tetradecanoic 16 Palmitic Hexadecanoic (Most abundant FA) 18 Stearic Octadecanoic 20 Arachidic Eicosanoic 22 Behenic Docosanoic Be 24 Lignoceric Tetracosanoic Li 26 Cerotic Hexacosanoic Ce UNSATURATED FATTY ACIDS LIPID COMMENTS OMEGA # # OF C / # OF = Δ DOUBLE BOND POSITION Palmitoleic 7 16:1 9 Oleic Cis – Oleic acid ; Trans – Elaidic acid 9 18:1 9 Linoleic Dietary precursor of PG (Vitamin F) 6 18:2 9, 12 (Omega 6) Linolenic 18:3 𝛼-9, 12, 15 (Omega 3) 𝛾-6, 9, 12 (Omega 6) Arachidonic Immediate precursor of PG 6 20:4 5, 8, 11, 14 (Omega 6) Timnodonic EPA (eicosapentanoic acid) 3 20:5 5, 8, 11, 14, 17 Cervonic DHA (docusahexaenoic acid) 3 22:6 4, 7, 10, 13, 16, 19 - for infant growth and development Linolenic Alpha : ↓ risk of heart disease, maintain normal heart rhythm and pumping Gamma: stimulate skin and hair growth, maintain bone health, regulate metabolism, and reproductive system FATTY ACIDS SOURCE USE 1 Sodium morrhuate (morrhuic acid) Atlantic cod, Gadus morhua Sclerosing agent (varicose) 2 Azelaic acid Ozonolysis of castor oil (Ricinus communis) Anti-Acne 3 Undecyclinic acid Pyrolysis of ricinoleic acid from castor oil Anti-Fungal FIXED OILS SOURCE ORIGIN ACTIVE CONSTITUENT Triricinolein – converted to ricinoleic acid Tangan-tangan Recinoleic acid - stimulant cathartic (laxative) 1 Castor oil Ricinus communis Ricin - toxic principle Recinine - alkaloid Oleic acid – pharmaceutic aid First grade virgin Less Pressure Oil of Europe / Sweet Second gv More Pressure 2 Olea europea oil Technical grade Hot Water Sulfur grade CS2 (Carbon Disulfide), Inferior Quality Tournant oil Fallen, decomposing fruits, High FA (stronger flavor, darker oil) Peanut oil / Arachis 75% Oleic acid, 25% Linoleic acid 3 Arachis hypogea oil Sesame / Teel / 4 Linga Sesamum indicum Oleic acid, Linoleic acid Solvent for IM injection Benne oil 5 Corn oil Zea mays Oleic acid, Linoleic acid 6 Cottonseed oil Gossypium hirsutum 0.6% Gossypol - Male Sterility Lecithin - control deranged lipid metabolism 7 Soybean oil Glycine soja Stigmasterol - precursor of steroid synthesis 8 Almond oil Prunus amygdalus Polyunsaturated fixed oil Apricot In temp. climate (solid vegetable oil) 9 Persic oil (Prunus armeniaca) 80 – 85% Lauric & Myristic acid 10 Coconut oil Cocos nucifera Edible oil, Nutritive, Liquid in tropic region (Philippines) WeCobee supp. Bases (solid vegetable oil) 2 PHARMACOGNOSY 11 Palm Kernel oil Elaeis guineensis 12 Rapeseed oil Brassica napus Canola oil 13 Safflower oil Carthamus tinctorius Believed to be anti-lipemic (fake news/false claim) 14 Sunflower oil Helianthus annuus Alternative to corn oil/safflower oil Linseed oil / Member of genus Linum which is food and fiber-crop cultivated 15 Linum usitatissimum Flaxseed oil “FLAX” in cooler regions Radiopaque diagnostic aid Ethiodized oil / 16 Papaver somniferum Iodine addition product of the ethyl esters of FA from poppy Injection seed oil FIXED OILS TESTS NOTES OLIVE OIL Millon’s Test May be contaminated with Tea tree oil or Camellia oil SESAME OIL Baudouin’s Test (+) Pink color with fuming HCl and Furfural COTTONSEED OIL Halphen or Bevan Test CORN OIL or any Serger Test (+) Yellow-blue hydrogenated vegetable oil FATS SOURCE USE Food, beverage, pharmaceutic aid, suppository base (Cacao seed: Cocoa butter) Polymorphs of Theobroma Oil Theobroma oil Theobroma cacao 1 Alpha – 17 - 18°C “Food for the Gods” (Oleopalmitostearin) Beta – 26 - 28°C Gamma – 22 - 23°C Beta stable – 34.5°C (BEST) 2 Lanolin / Hydrous Wool Fat Ovis aries (25 - 30% H2O) Ointment base 3 Anhydrous Lanolin / Wool Fat Purified fat-like sub. (sheep wool) (0.25% H2O) Ointment base, emollient Only liquid animal fat 4 Cod Liver Oil Gadus morhua Rich source of Vit. A and D (cAD liver oil) Sodium morrhuate (Sclerosing agent) 5 Butter fat Bos taurus Beef tallow → Bos taurus 6 Suet Bos taurus, Ovis aries Mutton tallow → Ovis aries 7 Lard Sus scrofa WAXES SOURCE ACTIVE CON. USE Emollient, stiffening agent in creams & Physeter 1 Spermaceti Cetyl esters wax ointments macrocephalus Physiologic product of sperm whale head Oin