PCOG LEC AND LAB Notes - AFGFHGHfsbgfg afgshshs sdhshgn sdhsgghs hshhsdghtths gsdghsdh PDF

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PCOG LEC REVIEWERINTRODUCTION TO PHARMACOGNOSYHISTORY OF PHARMACOGNOSYMESOPOTAMIABabylon ➢ The earliest known record of practice of the art of the apothecary – art of making medicines. ➢ Diseases were thought to be produced by “evil forces.” ➢ Religious persons or magicians were found to be associat...

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PCOG LEC REVIEWER INTRODUCTION TO PHARMACOGNOSY HISTORY OF PHARMACOGNOSY MESOPOTAMIA Babylon ➢ The earliest known record of practice of the art of the apothecary – art of making medicines. ➢ Diseases were thought to be produced by “evil forces.” ➢ Religious persons or magicians were found to be associated with the treatment of patients. Sumerians and Akkadians ➢ Developed the first pictographic writing system, which after a few hundred years developed into the writing style. ➢ Cuneiform – clay tablets Other Practices ➢ During the earlier times, practice of pharmacy & medicine were indistinguishable. ➢ Prehistoric men sometimes swallowed plants (bark, roots, leaves) to relieve indigestion or applied leaf or mud to protect & soothe bruised skin. HISTORY OF NATURAL PRODUCTS Egypt ➢ Ebers Papyrus – George Ebers o 60 feet long scroll which contains 811 prescriptions and mentions 700 drugs. o Currently in the University of Leipzig in Germany China ➢ Shang Hang Lun o Manual of traditional Chinese medicine by Chang Chung-ching. ➢ Pen Tsao Ching o An herbal compendium named after Emperor Shen Nung Pen Ts’ao which contains list of 200 herbs and instructions for 52 preparations. Greece ➢ Apollo o God of healing ➢ Asclepius (god of medicine) and his Daughters

o Hygieia – goddess of hygiene o Laso – goddess of recuperation o Aceso – goddess of healing & curing o Aglaea – goddess of good health o Panacea – goddess of remedy ➢ Hippocrates ➢ Theophrastus – father of botany ➢ Aristotle – father of zoology India ➢ Charaka Samhita o Oldest and most important authoritative writing on Ayurveda. ➢ Ayurveda o “Ayur” meaning life and “veda” meaning study of. It is the traditional medicine of ancient India Galen ➢ Greatest physician of Ancient Rome. ➢ Known for his Theriac and Galen’s cerate. o Theriac – herbal jam with 64 ingredients and was known as a universal remedy o Galen’s cerate – cold cream ➢ Associated with class of pharmaceuticals compound mechanically. o Galenicals – manually prepared solutions and creams Dioscorides ➢ Father of Pharmacology ➢ “De Materia Medica” which contains more than 600 plants, 35 animal products and 90 minerals Ibn Al Tabari ➢ Physican and Psychologist who produced one of the first encyclopedia of medicine ➢ Pedia Avicenna ➢ Aka Prince of Physicians of Persian Galen ➢ Known for his o Kitab al-Shifa – Book of Healing o al-Qanun fi al-Tibb – Canon of Medicine Ibn Al Baitar ➢ Notable botanist and Pharmacist. ➢ Known for his: o Compendium of Simples – 200 species

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Kitab al-Jami fi al-Adwiya alMufrada – botanical compilation “Hindiba” – herbal textbook for cancer

o Rhazes ➢ Aka Ibn-Zakariya. ➢ Greatest Arab Physician known for his Liber Continens ➢ “If you can help with foods, then do not prescribe medicaments; if simples are effective, then do not prescribe compounded remedies.”

DIFFERENT ERAS OF PHARMACOGNOSY 16TH & 17TH CENTURY: EUROPEAN EXPLORATON ➢ Sometimes known as Age of Exploration or Age of Discovery. ➢ New Route for the spice and silk. ➢ Sir Walter Raleigh and the legendary lost city of Gold – El dorado ➢ Columbus – exchange of goods 18TH CENTURY: SYSTEM OF CLASSIFICATION ➢ Johann Adam Schmidt and his Lehrbuch Der Materia Medica. ➢ Carolus Linnaeus and Taxonomy o Scientific names with linnae END OF THE 18TH CENTURY: ERA OF PURE COMPOUNDS ➢ Morphine – potent analgesic o Papaver somniferum (Opium Poppy) ➢ Strychnine and brucine o Strychnos nux-vomica ➢ Quinine (antimalaria) and Cinchonine o Cinchona calisaya o Cinchona succirubra (red bark) ➢ Caffeine – stimulant o Coffea arabica ➢ Nicotine – stimulant o Nicotiana tabacum ➢ Atropine – anti-cholinergic o Atropa belladonna (beautiful lady) ➢ Cocaine – hallucinating o Erythroxylum coca 19TH CENTURY: STUCTURE ELUCIDATION ➢ Structure Elucidation – organic medicinals

➢ Structures of compounds from various sources were determined. o Pharmacologic o Properties (Physical/Chemical) o ADRS (adverse drug reactions) 20TH CENTURY: ANIMAL SOURCES ➢ Discovery of important drugs from the animal kingdom such as vitamins and hormones BREAKTHROUGH OF ANTIBIOTICS: MICROBIOLOGICAL SOURCES ➢ Penicillin o Discovered by Alexander Fleming o Originally derived from moulds ➢ Vancomycin o Streptomyces orientalis ➢ Cephalosporins o Cephalosporium acremonium

PHARMACOGNOSY AS A DISCIPLINE Pharmacognosy is the oldest of all pharmacy sciences. ➢ The name “Pharmacognosy“ derived from the Greek words “Pharmakon”, meaning “a drug”, and “gignosco”, to acquire knowledge (the entire meaning of drugs) ➢ Definition: It is the science of biogenic or nature-derived pharmaceuticals and poisons ➢ Pharmacognosy is related to both botany and plant chemistry “Phytochemistry“, and its history entitles it to be regarded as parent of both. Pharmacognostical scheme:

1. Biological and Geographical Source o Botanical source (species, genus, etc.) 2. Cultivation, collection, and preparation o quality 3. Morphological and microscopical characters o Color, odor, taste 4. Chemical constituents 5. Uses o Pharmaceutical (how to make drugs)

o Pharmacological (effect/biological use) 6. Substituents o Substitute to drugs 7. Adulterants o Fake (no activity) 8. Chemical tests

FUTURE OF PHARMACOGNOSY 1. Safer Alternatives o For the treatment and cure of complex diseases like Cancer and AIDS. 2. Modern Analytical Techniques o To screen numerous complex and rare natural products 3. Drug Substitutes o For the semi-synthesis of many potent drugs. 4. Going back to Nature o Exploring the vast arsenal of natural resources for wonder drug.

Belong to a group of complex biomolecules commonly regarded as the “staff of life.” – carbohydrate is a source of sugar and sugar like glucose which is converted into an energy (ATP – main energy currency of the cell) needed in the body o They are the most abundant organic compounds in nature and are among the four major classes of biomolecules (CHO (most abundant in nature but least abundant in the body), CHON, Lipids, Nucleic acid). o They are aldehyde or ketone derivatives (applicable to monosaccharides)of the higher polyhydric alcohols (many OH groups) o During photosynthesis (endothermic reaction – absorbs heat), carbohydrates are produced from the reaction of carbon dioxide with water. Reaction of photosynthesis: o

Low molecular weight carbohydrates are crystalline, soluble in water and sweet in taste. o High molecular weight carbohydrates are amorphous (counterpart of crystalline), tasteless, and relatively less soluble in water. Ex. rice o Carbohydrates have chiral center(four different attachment) in its structure. Glucose molecule chiral centers: C2, C3, C4, C5 = 4 chiral centers o

CARBOHYDRATES CARBOHYDRATES (CHO) CHON – protein

DESCRIPTION AND PROPERTIES o

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General Formula – Cn(H2O)n for monosaccharides only – N/A to deoxysugars and amino sugars Also known as Hydrate of Carbon Group of compounds composed of carbon, hydrogen, and oxygen in which the latter two elements are in the same proportion as in water.

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Carbohydrates, simple sugars,can have different isomeric forms (molecules with same molecular formula but different arrangement of atoms or structure)

OLIGOSACCHARIDES o Class of carbohydrates possessing 2-10 monosaccharide units. o The monosaccharide units maybe linked via Oglycosidic or N-glycosidic bonds(amino sugars).

Enantiomers – left-handed (D-dextrorotatory) and righthanded molecules (L-levorotatory) Epimer - have the same molecular formula but differ in the Carbon

POLYSACCHARIDES o Aka complex sugars o On hydrolysis they give an indefinite number of monosaccharides. o Homoglycan (1 type of monosaccharides) vs heteroglycan (more than 1 type of monosaccharides) o Pentosan vs Hexosan o Glucosan vs Fructosan CLASSIFICATION OF MONOSACCHARIDES

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Carbohydrates may exist as straight chain (linear) or cyclic molecules (ring structure). Two types of ring in monosaccharides – furan (five-membered ring) & pyran (six-membered ring)

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Galactose – Brain sugar Glucose – Blood sugar Fructose – Fruit sugar

CLASSIFICATION OF OLIGOSACCHARIDES

Sucrose → Glucose + Fructose – connected by alpha 1 and beta 2 CLASSIFICATION OF CARBOHYDRATES Made of glucose o Maltose → Glucose + Glucose – connected by o in terms of no. of sugar units but they differ in alpha 1-4 the attachment o Cellobiose – beta 1-4 of the bond MONOSACCHARIDES o Trehalose – alpha 1-1 Anomer o Composed of only 1 sugar unit o Lactose→Glucose + Galactose – connected by o Simplest form Alpha and beta refers to the location of the OH. o Can have aldehyde or ketone functional group. ↑ – OH – beta o Can be further classified into number of Carbon ↓ – OH – alpha atoms. o

Raffinose→Glucose + Fructose + Galactose Gentianose → 2 Glucose + Fructose Stachyose → 2 Galactose + Glucose + Fructose CLASSIFICATION OF POLYSACCHARIDES

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• Common; generates carbohydrates Dark reaction •

Electromagnetic energy is converted to a chemical potential, to be used by the plant (used in synthesis of other molecules)

* This is how carbohydrates from the photosynthesis are being converted into different forms of carbohydrates Glycosides o Closely related to carbohydrates o Disaccharides are being used to form glycosides

BIOSYNTHESIS OF CARBOHYDRATES How carbohydrates are being produced in living things such as plants Carbohydrates o Commonly found in plants o Product of photosynthesis o

CALVIN’S CYCLE CO₂ is utilized + H₂O + Sunlight + enzymes + chlorophyll = photosynth esis + O₂

*Sucrose is one of the first of the carbohydrates that are being synthesized or formed through photosynthesis in plants Polysaccharides o Group of carbohydrates commonly found in plants o Starch, cellulose o Formed from disaccharides (ex. sucrose)

SUGARS AND CARBOHYDRATE-RELATED PLANTS

2 Types of Reactions o Light reaction •

Light energy (energy coming from the sun) is being converted to sugar, along with CO₂

1. SUCROSE – table sugar Sources: o Sugar Cane (Saccharum officinarum, Poaceae) • Graminae – old name of Poaceea • Juice is boiled with lime – to neutralize acids • Adds sulfur dioxide – decolorant o Sugar maple (Acer saccharum, Aceraceae) o Sugar beet (Beta vulgaris, Chenopodiaceae) Description: o Molasses – is the residual syrup during the production.

o Uses: o o o

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Cosettes – smaller pieces of sugar beets Pharmaceutic necessity for syrups • USP: 85% sucrose (w/v) Masking agent in other preparations • Mask bitter or undesirable taste Demulcent • Sore throat (lozenges) • Soothing properties Nutrient

2. DEXTROSE Synonyms: o D-glucose, grape sugar (blood sugar) Source: o Enzymatic hydrolysis of Starch • Hydrolytic product is glucose • Glucosan Uses: o Nutrient o Dextrates - Pharmaceutic aid (sweetening agent, tablet binder and coating agent). • 93% dextrose 3. LIQUID GLUCOSE Synonym: o Starch Syrup or Corn Syrup Source: o Incomplete hydrolysis of starch chiefly composed of dextrose, dextrins, maltose and water. Uses: o Manufacture of candy, carbonated beverages, ice cream, bakery products, canning industry *Complete hydrolysis = glucose Incomplete hydrolysis = various 4. CALCIUM SALTS (gluconate, gluceptate and levulinate) Source: o Calcium gluconate is the calcium salt of gluconic acid • Gluconic acid – by product of oxidation of glucose

Uses: o

Electrolyte replenisher primarily for Calcium ions • Calcium ions – extracellular (outside the cell) cation; ▪ important in blood clotting; ▪ needed for muscle contraction; ▪ nerve impulses

5. FERROUS GLUCONATE Source: o Iron salt of gluconic acid Uses: o Hematinic → increase hemoglobin levels o Supplement for IDA (Iron-Deficiency Anemia) Examples: o Ferrous gluconate – 12% • Will not result in gastric irritation o Ferrous sulfate – 20% o Ferrous fumarate – 33% 6. FRUCTOSE Synonym: Levulose and Fruit sugar Source: o Inversion of aqueous solutions of sucrose and subsequent separation of fructose from glucose o Inulin Hydrolysis Uses: o Nutrient for diabetic people, infant feeding formulas • Diabetic – high sucrose level; fructose is supplemented to prevent high blood sugar levels o Ingredient in fructose injection 7. LACTOSE Synonym: o Milk sugar Source: o Bos taurus, bovidae Uses: o Pharmaceutic aid (Tablet diluent) o Nutrient for infants *Milk Products o Butter – fat globules o Buttermilk – liquid layer

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Skimmed milk – milk left after separation of the cream (milk with buttermilk) Coagulum – milk + renin (ezyme for milk curdling) = cheese (solid form) Whey – milk + renin = liquid form Malted milk – evaporated milk with malt extract Condensed milk – concentrated milk with sugar;

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Uses: o o o

8. LACTULOSE Synonym: o Duphalac Source: o Semisynthetic sugar – arranged from alkaline rearrangement of lactose. Uses: o Laxative • Lactose → Colon (bacteria) → lactic acid & acetic acid • Acts as acidifier o Decrease blood ammonia in the management of Hepatic encephalopathy • High levels of ammonia • Lactic acid & acetic acid – causes shift in ammonia levels that leads to decrease of ammonia levels 9. XYLOSE Synonym: o Wood sugar Source: o Boiling corn cobs, straw or similar materials with dilute acid to hydrolyze the xylan polymer. Uses: o Diagnostic agent for intestinal malabsorption. • Easy to absorb • Urine detection – if xylose is detected in urine, intestinal malabsoption is confirmed 10. MANNA Synonym: o Manna ash Source: o Fraxinus ornus, Oleaceae Forms: o Dried saccharine exudates

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Mannitol – hexahydric alcohol from the reduction of mannose (composed of 6 –OH groups) Laxative Osmotic diuretic • Induces urination Diagnostic aid • Similar to xylose – needs to be absorbed in the intestine Management of ICP • Intracranial pressure – high pressure in the brain caused by trauma or hemorrhage

11. SORBITOL Synonym: o D-glucitol, Sionin (Europe) Source: o Sorbus aucuparia, Rosaceae Uses: o Humectant • Retains moisture • Property in creams and ointments o Osmotic laxative o Urologic irrigation together with Mannitol • Cleanses urinary tract o Ingredient in toothpaste and chewing gums. 12. CASSIA FISTULA Source: o Cassia fistula, Fabaceae 13. TAMARIND Source: o Tamarindus indica, fabaceae 14. PRUNE Source: o Prunus domestica, Rosaceae 15. CHERRY Source: o Prunus cerasus, Rosaceae

Flavorant Laxatives Nutrients

16. PURIFIED HONEY Source: o Apis mellifera, Apidae Use: o Cough mixtures • Demulcent – soothing properties

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o 17. FIG Source: o Ficus carica, Moraceae Use: o Laxative preparation 18. FUCUS Source: o Fucus vesiculosus, Fucus serratus (FN: Fucacaea) Constituents: o alginic acid, iodine, polyphenols Uses: o Iodine therapy, slimming agent (plants used as this are laxatives), bulk laxative 19. CETRARIA OR ISLAND MOSS Source: o Cetraria islandica (FN: Parmeliaceae) Constituents: o Lichenin (soluble in hot water), solichenin (soluble in cold water), depsidone (bitter principles), usnic acid (can be a source of antibiotic) Uses: o Demulcent, bitter tonic, masking agent for nausea medicines (though bitter)

POLYSACCHARIDES A. STARCH o Major carbohydrate reserve in higher plants, over 85% of the dry weight o Glucosan (composed of only glucose), hexosan (glucose is a hexose), o Homoglycan (only yield one sugar) Components: o Amylose – linear, Alpha 1-4 glycosidic bond, more soluble, reaction with Iodine produces intense blue black, percentage: 20%

Amylopectin – branched, Alpha 1-4 and Alpha 16 glycosidic bond, less soluble, no reaction w/ iodine, percentage: 80% Found as granules (ovoid or spherical in shape) in the chloroplasts of plant leaves or amyloplasts of storage organs such as seeds and tubers Sources: Corn, wheat, potato and rice

20. CORN STARCH (Zea mays, Poaceae) 21. WHEAT STARCH (Triticum aestivum, Poaceae) 22. POTATO STARCH (Solanum tuberosum, Solanaceae) 23. RICE STARCH (Oryza sativa, Poaceae) 24. ARROWROOT STARCH (Maranta arundinacea, Marantaceae) 25. CASSAVA STARCH (Mannihot esculenta, Euphorbiaceae) Uses: o Antidote for iodine poisoning o Pharmaceutic aid (dusting agent, tablet filler, binder, disintegrant) o Plasma Expander (Hetastarch– adjunct therapy for shock [for those who have burns, hemorrhage and for those who undergo surgery. Decreased blood pressure due to decreased blood volume]) B. INULIN – fructosan Sources: o Occurs in cell sap and by immersing the rhizome or root in alcohol for some time, the inulin crystallizes in sphaerite aggregates. Uses: o Fermentative identifying agent o Evaluation of renal function *GFR – glomerular filtration rate o Reveals main function of your kidneys. Is there an allowable filtration rate? Inulin is easily excreted when there is no renal malfunction. If insulin is not present, then there may be a renal malfunction) *Food high in inulin: wheat bread, shallots and red onions, Jerusalem artichokes, chicory root, Rye, leeks (the bulb)

C. DEXTRAN Sources: o Polyglucan formed from sucrose by the action of transglucosylase enzyme (dextran sucrase) system in Leuconostoc mesenteroides (will release enzyme which will catalyze sucrose. Sour taste in kimchi, pickels. Bacteria is nonpathogenic [will not cause any disease]) Uses: o Plasma volume expander D. CELLULOSE Sources: o Primary polysaccharide in plant cell wall. Forms: o Purified cotton, Gossypium hirsutum, Malvaceae • Uses: Surgical dressing, textile industries, manufacture of explosives. o Pyroxylin – nitrocellulose, starting material for explosives • Product obtained by the action of HNO3 and H2SO4 on cotton; consists of cellulose tetranitrate • Uses: Preparation of collodion (pyroxylin+alcohol+ether) and flexible collodion (pyroxylin+2% camphor+3% castor oil) and topical protectant. Uses: o Tablet enteric coating – releases drug in small intestine (cellulose acetate phthalate) o Artificial tears (methylcellulose – used as lubricant – for contact lenses) o Tablet excipient (microcyrtalline cellulose) E. GUMS AND MUCILAGES o Gums are extracellular formations and due to pathological process caused by bacterial transformation of cellulose and starch. o Mucilages are intracellular formations and due to physiologic process of the plants; beneficial for the plant 26. ACACIA OR GUM ARABIC Source: o Acacia senegal, Fabaceae

Description: o It has low viscosity and good stability. It is differentiated from other constituents using ferric chloride and iodine test. o most commonly used, no compatibility issues o differentiated using ferric chloride (no bluish black vs. tannins) and iodine test (no bluish black vs. starch ; no color) Constituents: o Arabin and Arabic acid Uses: o Demulcent (soothing properties) o Emulsifying and thickening agent o Binder and adhesive o Microencapsulation (together with gelatin) 27. GHATTI OR INDIAN GUM Source: o Anogeissus latifolia, Combretaceae Description: o It produces more viscous dispersions than acacia but less than sterculia gum. Uses: o Substitute for acacia (for emulsions like creams, ointments, and lotions, and suspensions) 28. STERCULIA OR KARAYA GUM Source: o Sterculia urens, Sterculiaceae Description: o Consists of acetylated, branched heteropolysaccharide with a high component of galacturonic acid and glucoronic acid. o One of the least soluble exudates, very viscous b/c least soluble exudates Uses: o Bulk laxative o Adhesive for dental fixtures o Demulcent o Emulsifier, thickener and stabilizer. 29. TRAGACANTH/GOAT’S THORN/GUM DRAGON Source: o Astragalus gummifer, Fabaceae Description: o The gums are graded into ribbon or flakes. Ribbon - the lower the grade #, the better

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o Uses: o o o o o

(ribbon #1 and #2 are usually used for drug products, 3, 4, 5, are for food); flakes • Shapes can be vermiform (worm-like) or tragacanth sorts (tears/ irregular shape; yellowish - brownish color)...