PHARMACOGNOSY (MODULE 2) – Carbohydrates, Lipids, Glycosides, and Alkaloids (Overview)

Vocabulary flashcards covering key terms in carbohydrates, lipids, glycosides, and alkaloids from the lecture notes.

Xylose

Aka wood sugar; obtained by hydrolysis of xylan from corn cobs/straw; diagnostic agent for intestinal malabsorption.

Glucose

Aka dextrose, blood sugar, grape sugar; used as purified parenteral nutrient source and as a pharmaceutical sweetener.

Fructose

Aka fruit sugar; sweetest monosaccharide with a bitter aftertaste; obtained by inversion of sucrose or isomerization of glucose.

Galactose

Aka brain sugar; C4 epimer of glucose.

Mannose

C2 epimer of glucose.

Sucrose

Aka table sugar; disaccharide of glucose and fructose (α-1 to β-2 linkage); source: sugar cane/beet/maple; used as a sweetener and coating agent.

Maltose

Aka malt sugar; disaccharide of two glucose units (α-1,4); produced by diastatic starch fermentation; used in beer.

Lactose

Aka milk sugar; disaccharide of galactose and glucose (β-1,4); source: cow’s milk.

Lactulose

Product of alkaline rearrangement of lactose; disaccharide of galactose and fructose; used as a stimulant laxative.

Cellobiose

Disaccharide of glucose (β-1,4); produced from cellulose.

Ethanol

Alcohol produced by glucose fermentation; used as disinfectant/vehicle; various beverage types (brandy, whiskey, rum, gin, vodka, tequila).

Mannitol

Sugar alcohol derived from manna; used as an osmotic diuretic.

Sorbitol

Also called D-glucitol; sugar alcohol from sorbose; used as a sweetener (found in toothpastes and gums).

Starch

Plant storage polysaccharide composed of amylose and amylopectin; paste-forming due to amylopectin; pregelatinized starch is a tablet binder; sodium starch glycolate is a superdisintegrant.

Cellulose

Plant structural polysaccharide; glucose polymer; purified cellulose used in dressings; cellulose acetate phthalate for coating; hypromellose as artificial tears.

Glycogen

Animal storage polysaccharide; highly branched glucose polymer; iodine test turns red-violet like amylopectin.

Dextran

Glucan with α-1,3 and α-1,6 linkages; used as a plasma expander (10% solution).

Inulin

Fructan from chicory root; evaluated for renal function but largely replaced by GFR due to cost.

Chitin

Polymer of N-acetylglucosamine found in exoskeletons of insects and crustaceans; molting occurs as size increases.

Pectin

Heteropolysaccharide from galacturonic acid with various pentoses; forms protopectin (unripe), pectin (ripe), pectinic acid (overripe).

Gums and Mucilages (Plant exudates)

Natural polymers like acacia (gum arabic), tragacanth, karaya; used as suspending agents; marine gums include agar, algin, carrageenan; Danish agar.

Xanthan

Microbial gum produced by Xanthomonas campestris; has pseudoplastic (shear-thinning) properties; used in toothpaste and ointments.

Psyllium

Seed gum from Plantago ovata; bulk-forming laxative.

Quince

Seed gum from Cydonia vulgaris; used as a thickener/suspending agent.

Guar

Guar gum from Cyamopsis tetragonolobus; thickener/suspending agent.

Locust bean gum

Locust bean gum from carob pod (St. John’s Bread/Carob pulp/Locust bean); used as thickener; chocolate substitute in some contexts.

Xyg text: Xanthan

Duplicate card not needed.

Pectinic acid

Overripe pectin; a degraded form of pectin.

Pectin (Kaopectate)

Pectin is an ingredient in Kaopectate; pectin with kaolin forms an antidiarrheal combo.

Agar (Japanese Isinglass)

Gelling agent from red algae; used as culture medium.

Algin

Sodium alginate from brown algae; raft-forming antacid; component of Gaviscon.

Carrageenan (Irish Moss)

Gelling agent from red algae; forms kappa, iota, and lambda gels.

Danish Agar

Agar variant with gel-forming properties similar to kappa carrageenan.

Starch derivatives and related notes

References to pregelatinized starch, sodium starch glycolate, Hetastarch; table 5 pg 69 notes details.

Pectin, Gums, and Polysaccharides summary

Overview of polysaccharides used as excipients (thickeners, suspending agents, disintegrants, etc.).

Sorbitol (summary)

Sugar alcohol used as sweetener; half as sweet as sucrose.

Linseed oil

Also called flaxseed oil; used in paints and varnishes; highly unsaturated.

Cod liver oil

Rich in omega-3 fatty acids and vitamins A and D; marine oil used in health products such as Scott’s Emulsion.

Cottonseed oil

Contraceptive history; later linked to male sterility due to gossypol; Halphen-Bevan test used.

Corn oil

Oil from corn; highly unsaturated; used in pharmaceuticals.

Peanut oil

Arachis oil; also called groundnut oil.

Sesame oil

Aka benne oil; contains sesamolin (a synergist).

Coconut oil

High in short- to medium-chain fatty acids; low iodine value; more saturated.

Olive oil

Aka sweet oil; graded by pressing; Millon’s test positive; grades include virgin, second, technical, sulfur, tournant.

Almond oil

Emollient in cosmetics.

Castor oil

Ricinoleic acid is the main laxative component; pyrolysis yields undecylenic and ozonolysis yields azelaic acid.

Ethiodized oil

Ethyl esters of opium alkaloids; radiopaque agent used in gynecologic procedures.

Evening primrose oil

Rich in gamma-linolenic acid (omega-6).

Hydrogenated vegetable oil

Hydrogenated fats; tested by Sierger’s test (likely iodine or iodine value related).

Canola oil

Low erucic acid (<2%); heart-healthy; related to rapeseed oil which has higher erucic acid.

Palm kernel oil

Oil from palm kernels; high in saturated fats.

Sunflower oil

Oil from sunflower seeds.

Safflower oil

Kasubha; Philippine saffron; claimed anti-lipemic activity.

Soybean oil

Glycine soja oil; source of phytosterols like stigmasterol; contains lecithin (phosphatidylcholine) that helps regulate lipid levels.

Theobroma cacao oil

Cocoa butter; fixed oil from cacao.

Lanolin

From sheep wool; used as a moisturizer and ointment base; contains water content.

Suet

Fat from beef tallow and mutton tallow.

Lard

Fat from pig.

Spermaceti

Wax from the head of sperm whale; cetyl esters of fatty acids; used as ointment base.

Jojoba oil

Liquid wax; emollient; unique among waxes for being liquid.

Carnauba wax

Hard natural wax; used for candles, cosmetics, furniture polishes; composed of myricyl cerotate.

Beeswax

Wax from honeybees; composed mainly of myricyl palmitate; used as stiffener.

Podophyllotoxin

Precursor to antineoplastic drugs etoposide and teniposide; isolated from Mayapple (Podophyllum peltatum).

Ginseng constituents

Panaxosides and ginsenosides; adaptogenic and aphrodisiac properties.

Kava-kava

Piper methysticum; contains kawain, yangonin, methysticin; sedating; used as a tranquilizer.

Cannabis sativa

Marijuana; contains cannabinoids; young plants have cannabidiol; mature plants contain cannabinol (THC); resin called hashish.

Duquenois test

Qualitative test for cannabis resin.

Podophyllum peltatum

American mandrake; source of podophyllotoxin.

Podophyllotoxin

Precursor to antineoplastic drugs; inhibits topoisomerase II.

Senna (Alexandria and Tinnevelly)

Laxative; contains sennosides.

St. John’s Wort

Hypericum perforatum; contains hypericin and hyperforin; antidepressant; induces CYP enzymes.

Hypericin and hyperforin

Active constituents in St. John’s Wort; modulate mood; interact with other drugs via CYP induction.

Sennosides

Laxative constituents from senna; more potent in some species.

Glycyrrhizin

Sweet-tasting glycyrrhizin from licorice; many uses including masking quinine bitterness; can affect taste and steroid balance.

Colchicine

Gout medication; anti-mitotic alkaloid from Colchicum autumnale.

Ephedrine

Mixed adrenergic agonist; nasal decongestant; precursor to methamphetamine.

Colchicine

Anti-gout alkaloid from Colchicum autumnale; anti-mitotic.

Quinine

Antimalarial alkaloid from Cinchona; can cause cinchonism (tinnitus); quinidine is a related antiarrhythmic.

Quinidine

Type 1A antiarrhythmic alkaloid from Cinchona.

Morphine

Opiate analgesic from opium poppy; highly addictive.

Codeine

Opium-derived antitussive.

Papaverine

Opium poppy alkaloid; smooth muscle relaxant.

Naloxone

Opioid antagonist used to treat opioid overdose; precursor of thebaine derivatives.

Cannabinoids (general)

Class of compounds in cannabis; include cannabidiol and cannabinol; THC is the psychoactive constituent.

Pilocarpine

Alkaloid from jaborandi; used to treat glaucoma.

Theophylline

1,3-dimethylxanthine; a methylxanthine alkaloid found in tea; bronchodilator.

Theobromine

3,7-dimethylxanthine; found in cacao; mild diuretic.

Caffeine

1,3,7-trimethylxanthine; central nervous system stimulant.

Veratrum (Green/White hellebore)

Cardiac depressant alkaloids; contain veratramine/Veratrum alkaloids; toxic plants.

Cinchona

Genus producing quinine/quinidine (antimalarial and antiarrhythmic).

Strychnine

Indole alkaloid from Strychnos nux vomica; CNS stimulant; convulsant; assayed by Mandelin test.

Physostigmine

Acetylcholinesterase inhibitor from Physostigma venenosum; used for glaucoma.

Strychnos nux vomica

Source of strychnine; toxic CNS stimulant; inhibits glycine receptors.

Ergot alkaloids

From Claviceps purpurea; includes ergotamine, ergonovine, ergometrine; causes ergotism; used in migraine and obstetrics.

Lysergic acid diethylamide (LSD)

Psychoactive ergoline alkaloid derived from ergot; powerful hallucinogen.

Aloe barbadensis

Aloe; contains barbaloin and emodin; uses include moisturizer and skin creams.

Salicin

Alcohol from willow bark; precursor to salicylic acid; first aspirin-related discovery.

Arbutin

Hydroquinone glycoside from Uva-ursi; used for whitening; diuretic and astringent effects.

Urushiol

Oleoresin from poison ivy; causes contact dermatitis (type IV hypersensitivity).

Vanillin

Aldehyde from vanilla planifolia; glucovanillin precursor; curing yields vanilla flavor.