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Module 2 Pharmacognosy Plant Chemistry, Biochemistry Kathreen Mae D. Cascabel BSPharmacy
INTRODUCTION TO PHARMACOGNOSY Pharmacognosy – knowledge of drugs and pharmaceuticals | Greek: pharmakon (drugs) and gnosis (knowledge) BRIEF HISTORY Babylonians – made clay models of man Egyptians – very apt in the practice of embalming Greeks Pedanios Dioscorides – De materia medica libre cinque (five volumes), 600 plants (Rome) Galen – described the method of preparing formulas containing plant and animal drugs and the term ”Galenical pharmacy” originated (Cold cream – Galen’s cerate) Germans C.A. Seydler – coined the term pharmacognosy in his dissertation in 1815 (title: Anaclectica pharmacognosthica) Fluckiger –most comprehensive definition of pharmacognosy : “simultaneous application of various scientific disciplines with the object of acquiring knowledge of drugs from every point of view” J.A. Schmidt – Lerbuch der Materia medica Pharmacognosy – “an applied science that deals with the biologic, biochemical and economic features of natural drugs and their constituents that originate in the plant and animal kingdom” General Process of Extraction Removes substances that can be dissolved by the solvent/menstruum The undissolved portion of the drug is known as the marc Product of extraction process: Percolate/Extractive Crude Drugs Natural Substances Derivatives/ Extractives Geographic source & Habitat Indigenous Naturalized
Appropriate Solvents: 1. Fats 2. Resins 3. Chlorophyll 4. Chrysarobin
- Hexane - Alcohol - Acetone - Hot benzene
– undergone only collection and drying – have not had changes made in their molecular structure as found in nature – chief constituents obtained by extraction – region in which the plant or animal yielding the drug grows – growing in their native countries – growing in foreign land
PREPARATION OF DRUGS FOR THE COMMERCIAL MARKET 1. Collection – (small scale) collection time: part of the plant that constitutes the drug is highest in its content of AI 2.
Harvesting – (large scale) Mechanical devices : pickers, mowers, binders, swath, steel Manual – for potent constituents
3.
Drying (Air Drying and Artificial Air Drying) • remove moisture • fixes the constituents • prevent molding • facilitate grinding and milling • prevent action of bacteria • prevent environmental hydrolysis
Collection time Pectin – citrus fruits Unripe fruits - protopectin Just ripe - pectin Overripe - pectic acid
Marijuana Young leaves - cannabidiol Mature leaves - cannabinol (THC)
4.
Garbling – final stage; removal of extraneous matter (other parts of the plant, dirt, added adulterants)
5.
Packaging, Storage and Preservation To avoid insect attacks: a. SIMPLEST METHOD: Expose the drug to 65°C b. Fumigation with methyl bromide c. Add adrop of chloroform or carbon tetrachloride
Examples of Plants in De Materia Medica Aloe Belladonna (beautiful lady) Tamoxifen Colchicum Allopurinol Ergot (“fingers” Claviceps purpurea) Opium (stone of immortality) Premarin Digoxin (Digitalis lanata) Digitoxin (Digitalis purpurea)
Emollient, tx for burns Atropine – mydriatic (SE: cycloplegia) For breast CA (SE: endometrial CA) Acute gout Chronic gout (Xanthine Oxidase inhibitor) Ergotamine (migraine), Ergonovine (oxytocic), LSD (hallucinogen) Estrogen derivative from MARE
Bioassay Digoxin - pigeon Atropine - cats Glucagon - cats Oxytocin - chicken (F) Head drop test - rabbits/rats PTH - dogs Heparin - sheep plasma Insulin - rabbit
Lipid soluble, Long half life
Street names of illegal drugs 1. Shabu Ice, Meth 2. Ecstacy Sky 3. Marijuana Hashish, MJ/Maryjane, Pot, Grass, Weed, Cannabis, Indian hemp EVALUATION OF DRUGS (determine the quality (intrinsic property) and purity (absence of adulterants) of drugs) 1. Organoleptic - by means of the organs of sense; macroscopic appearance 2. Microscopic - essential in the study of adulterant in powdered plants (identity and purity) 3. Biologic - pharmacologic activity of certain drugs has been applied to their evaluation or standardization 4. Chemical - assay of AC using chemicals (titration); best method of determining official potency 5. Physical - physical constants (solubility, spec grav, optical rotation, congealing point, refractive index, MP) CLASSIFICATION OF DRUGS Morphology Taxonomy Pharmacologic or Therapeutic Chemical classification
– forms – phylogeny (natural relationship or among plants and animals) – based on effect on the body – based on active constituents; Preferred Method of Classification
CHEMISTRY OF NATURAL DRUG PRODUCTS 1. Pharmaceutically active – cause chemical changes in the preparation 2. Pharmacologically active – responsible for the therapeutic activity 3. Inert constituents – no definite pharmacologic activity 4. Secondary plant substance – extracted, crystallized and purified; presence of inert matter which may modify or prevent absorbability or potency of AC Drug biosynthesis/Biogenesis – study of the biochemical pathways leading to formation of secondary constituents (drugs) Primary metabolites
to
Secondary metabolites
Carbohydrates Proteins Fats
Glycosides BIOGENESIS OR DRUG BIOSYNTHESIS
Tannins Volatile oils or Fixed oils
3 Principal factors that influenced the secondary constituents of drug plants 1. heredity (genetic composition) 2. ontogeny (stage of development) 3. environment (soil, climate, associated flora and method of cultivation)
CARBOHYDRATES AND RELATED COMPOUNDS
polyhydroxyaldehydes or polyhydroxyketones containing C, H and O; same ratio as in H2O (2:1) 1st products of photosynthesis (glucose) General formula: CnH2nOn | Cn(H2O)n | (CH2O)n
CHO 4 cal/g CHON 4 cal/g Fats 9 cal/g
MONOSACCHARIDES Cannot be hydrolyzed to simple sugar substances that is ketonic or aldehydic substitution product of a polydroxy alcohol C 2 3 4 5 6 7 8
Name Diose Triose Tetrose Pentose Hexose Heptose Octulose
Aldose Hydroxyacetaldehyde Glyceraldehyde Erythrose Arabinose, Xylose, Ribose Glucose, Galactose Sedoheptose D-glycero-D-mannoctulose
Ketose Dihydroxyacetone Erythrulose Ribulose Fructose
HEXOSES (most important monosaccharides found in plants) Glucose (aldohexose)
Fructose (ketohexose)
Other names D-glucose Dextrose Blood sugar Grape sugar Physiologic sugar Fruit sugar Levulose (sweetest monosaccharide)
Uses Nutrient (parenteral), Excipient Ca gluconate/gluceptate/levulinate – Ca replenisher Ferrous gluconate – hematinic
Identification Test Moore’s Test (caramel)
Food for diabetics Ingredient in infant feeding formula Ingredient in fructose injection, nutrient
Seliwanoff’s Test
PENTOSES Xylose (D-xylose, Wood Sugar) obtained by boiling corn cobs, straw or similar materials with dilute acid to hydrolyze the xylan polymer diagnostic aid in intestinal malabsorption
OLIGOSACCHARIDES DISACCHARIDES Sucrose Glu + Fru (non-reducing)
Maltose Glu + Glu Lactose Glu + Gal (reducing)
Other N Saccharum Cane sugar Beet sugar Table sugar Malt sugar
Origin Saccharum officinarum (cane) Beta vulgaris (beets) Acer saccharum (maple)
Milk sugar
Cow’s milk (Bos Taurus)
Uses Demulcent, Sweetening, Coating, Preservative, Production of syrups, Retards oxidation
From germination of barley
Lactulose (Alkaline lactose) lactic & acetic acid (irritation, catharsis) Dec serum NH3 in encephalopathy
Isolation of Lactose Butter – cream, united fat globules Buttermilk – liquid separating from butter Skimmed milk – left after cream separates Cheese – coagulum, skimmed m. + rennin Whey – liquid separated from coagulum
POLYSACCHARIDES
Polysaccharides are polymers of monosaccharides (sugar) linked together through glycosidic(ether) linkages Temporary storage form of photosynthetic products systematic nomenclature are given the ending “an”, glycan is another word
Amylose Linear 250-300 glucose units 25% α-1,4 glucosidic bonds Soluble Blue
Amylopectin Branched 1000 or more glucose units 75-80% α -1,4 and α-1,6 (every 25 glucose) Insoluble (paste forming) Blue-violet or purple
HOMOGLYCANS Starch (Glucosan) Zea mays (corn) Triticum aestivum (wheat) Solanum tuberosum (potato)
Use Tablet filler, binder, and disintegrant Antidote for iodine poisoning Permanent reserve food material in plants
Enzymes that break down starches: β amylase – pancreatic juice and saliva α amylase – hydrolyzes it to maltose Starch
Gluten Pregelatinized Starch Na Starch Glycolate Hetastarch
– tachy proteins – binder – disintegrant – plasma expander
Soluble starch Dextrin Maltose
Inulin (Fructosan) Dextran (Glucosan) - plasma expander Cellulose
2 glucose Ingredient in culture media Used in evaluation of renal function dextran sucrase (from Leuconostoc mesenteroides) Sucrose Dextran Purified/Absorbent Cotton – from the hair of the seeds of Gossypium hirsutum Use: mechanical protection against bacteria; absorb mucus, pus, and blood Soluble guncotton/Pyroxylin – formed by action of nitric acid & sulfuric acid on cotton Other ingredients: Castor oil (flexibility) | Camphor (proof) Use: topical protectant Other derivatives: Cellulose Acetate Pthalate (CAP) – film coating, Methyl/Ethylcellulose
HETEROGLYCANS (yield more than one type of monosaccharide units upon hydrolysis) Gums and Mucilages Natural plant hydrocolloids that may be classified as anionic or non-ionic polysaccharides Produced by plants as a protective after injury Upon hydrolysis, they yield arabinose, galactose, glucose, mannose, xylose, and other uronic acid derivatives USES: suspending agents, dental adhesives, laxatives
PLANT EXUDATES Tragacanth
Astragalus gummifer
Bassorin (swells) Tragacanthin (thickener)
Arabin
Best mucilage (resistant to acid hydrolysis)
Acacia
Gum arabic
Acacia senegal
Ghatti
Indian Gum
Anogeissus latifolia
Karaya
Sterculia Gum
Sterculia urens
D-galacturonic acid D-glucoronic acid
(fetid odor)
Suspending agent, Emulsifier, Adhesive, Demulcent, Emollient 5-6% dispersion in H2O Incompatible with OH 35-36% dispersion Acacia substitute Laxative, Suspending agent, Adhesive
MARINE GUMS Agar Algin
Japanese Gelidium cartilagineum Insinglas/Gelatin (Red algae) Macrocystis pyrifera
Agarose Agaropectin Sodium alginate
(brown seaweed)
Carageenan
Irish Moss, Chrondus
Chondrus crispus Gigartina mamillosa
Danish agar
Furcerallan
Furcellaria fastigiata
Kappa- & Iotacarageenan (swelling) Lambda-carageenan (nonswelling) k-carrageenan
Laxative, tablet diluents/disintegrant Suspending agent, tablet binder, thickener Demulcent, bulk laxative
Suspending agent
SEED GUMS Plantago Cydonium
Psyllium, Plantain Seed Quince seed
Plantago psyllium (Spanish) P. ovate (Blonde/Indian) Cydonia vulgaris
Guar Gum
Guaran
Cymopsis tetragonolobus
Locust Bean Gum
Carob pulp St. John’s bread
Ceratonia siliqua
Bulk laxative
1,4 linked Dmannopyranosyl
Laxative, thickener, binder Chocolate substitute
MICROBIAL GUM Xanthan Gum
Xanthomonas campestris
Peudoplastic activity which enables toothpaste and ointment both to hold shape and spread readily
PECTIN – purified carbohydrate product obtained from the dilute acid extract of inner portion of the rind of citrus fruits or from apple pomace Active Constituent : linear 1,4 linked D-galacturonan Uses : protectant, s.a., ingredient in many antidiarrheal formulations
[O] PLANT ACIDS a. Cherry Juice or Succus cerasi Ripe fruit of Prunus cerasus Contains pectin (incompatible with OH) Constituent: Malic acid (present in cherry, apple, pear) Use: preparation of cherry syrup b. Plant Acids Uses: Acidulants in effervescent formulations, Component of buffer systems a. Citric acid - (2-hydroxy 1,2,3, propane trioic acid) isolated by Scheele from lemon juice in 1784 b. Lactic acid - (alpha-hydroxy propionic acid) acidulant in infant feeding formula c. Tartaric acid - (1,2,3, dihydroxy butane dioic acid) by product of wine industry d. Fe fumarate - hematinic c. Alcohol or Ethanol 95% ethanol by volume @15.56°C Product of fermentation Undergo the process of distillation to concentrate the alcohol content to 40-55% brandy - distilled wine whiskey - malted grain rum - molasses wine - mild stimulant and tonic
[H] SUGAR ALCOHOLS
Mannitol (D-mannitol) From Manna, Fraxinus ornus Osmotic diuretic and Osmotic laxative
Sorbitol (D-glucitol) From the ripe berries of mountain ash, Sorbus aucuparia half as sweet as sucrose has humectant properties (ingredient in toothpaste, chewing gums and various dietetic products) not absorbed on oral ingestion that is why it is used in the manufacture of chewing gums
TESTS FOR CARBOHYDRATES Molisch’s Fehling’s Benedict’s Barfoed’s Tollen’s Picric acid Nylander’s Osazone/Kowarsky Seliwanoff’s Keller-Killiani Test Moore’s Mucic acid Test Bial’s
Test for General for carbohydrates Reducing sugars Reducing sugars Reducing sugars; Monosaccharides Reducing sugars (Aldehydes) Reducing sugars Reducing sugars Mannose Ketohexose (Fructose) Deoxysugars (cardiac glycosides) Reducing sugars (Glucose) Galactose Pentoses
Composition α-naphthol A – CuSO4 B – K Na tartrate NaOH + CuSO4 Cupric acetate + acetic acid Silver + Ammonia Picric acid Na K tartrate + K/NaOH + Bi Phenylhydrazine Resorcinol Acetic acid, Fe chloride, Sulfuric acid Heat with alkali Nitric acid Resorcinol + Fe
Positive result Purple/Red Brick red ppt Brick red ppt Brick red ppt Silver mirror Mahogany red Brown Yellow ppt (ozone) Red Reddish brown Caramel Insoluble ppt Blue green
GLYCOSIDES
Heteroglycans (yield one ore more sugars among the products of hydrolysis); simple glycosides: sugar ethers The most frequently occurring sugar is Beta-D-glucose (plants) Aglycone or genin – nonsugar component, Glycone – sugar component
CARDIOACTIVE OR CARDIAC GLYCOSIDES MOA: inhibits Na/K/ATPase pump increased influx of Ca2+ ions (+) inotropy 2 types of steroidal aglycones or genin: Cardenolides - most prevalent in nature Bufadienolides - are homologs of the cardenolides and an unsaturated 6-membered lactone ring DOC: control rapid ventricular rate in px with atrial fibrillation/atrial flutter Keller-Killiani Test - Detects presence of 2-deoxysugars Other Names Grecian Foxglove Foxglove Convallaria Adonis Strophanthus Apocynum Oleander/Adelfa Squill Cactus Grandiflorus Black Hellebore
Origin Digitalis lanata Digitalis purpurea Convallaria majalis Adonis vernalis Strophanthus kombe Apocynum cannabinum
Active Constituent Digoxin Digitoxin (lipid soluble, long t½) Convallatoxin Adonitoxin k-strophanthoside/Strophanthidin Cymarin Oleandrin Scillaren A
Night blooming cereus
Nerium oleander Urginea maritime Selenicereus grandiflorus
Christmas rose
Hellebborus niger
hellebrin
Lily-of-the-Valley Pheasant’s eye Black Indian Hemp Dog bane, Canadian Hemp Rose bay
ANTHRAQUINONE GLYCOSIDES Cathartics (except chrysarobin) Aglycone: Anthracene ID test: Borntrager’s test
Cascara Sagrada
Sacred bark
Origin Rhamnus purchianus
Active Constituent D glycosides – based on emodin C glycosides – based on aloin Cascarosides A&B – barbaloin isomers Cascarosides C&D – chrysaloin isomers Casanthranol – purified mixture of anthranol glycosides from cascara sagrada
Frangula Aloe
Buckthorn bark
Rhubarb
Rheum/Chinese Rhubarb
Senna
Cultivated on wet lands resembling rice paddies
Chrysarobin
Rhamnus frangula Aloe barbadensis/Aloe vera (Curacao) A. ferox + africana + spicata (Cape) Rheum officinale (Chinese) R. emodi, R. webbianum (Indian/Himalayan) Cassia angustifolia (Tinnevelly) Cassia acutifolia (Alexandria) Andira araroba (Goa powder; hot benzene)
Frangulin A & B Barbaloin Aloe-emodin Rhein anthrones Sennosides A, B, C, and D *More potent than cascara Keratolytic agent
SAPONIN GLYCOSIDES β-hemolytic substances – destroys RBC by hemolysis and are toxic to cold blooded animals (used as fish poison) Soap-like (foam upon shaking) o Steroidal in nature (cyclopentanoperhydrophenanthrene/CPPP nucleus) o Sapotoxin – toxic aglycone o Sapogenin – aglycone portion, 2 types: Steroid (neutral saponin) and Triterpenoid (acid saponin) Identification tests: 1. Froth test - (+) honeycomb froth that persists for 10 mins 2. Capillary test 3. BAM (Blood Agar Media) Test or Hemolysis Test α hemolysis – partial hemolysis β hemolysis – complete hemolysis γ hemolysis – no hemolysis
Glycirrhiza Licorice root
Ginseng • fave remedy in Chinese medicine
Dioscorea Mexican Yam
Origin Glycyrrhiza glabra
Panax quinquefolius (American) Panax ginseng (Asian/Korean) D. floribunda – best source of steroid D. spiculiflora – contains diosgenin
Active Constituent Glycyrrhizin/glycyrrhic acid (50x as sweet as sugar)
Use Peptic ulcer and Addison’s Increases foaminess of beer.
Glycyrrhetic acid (anti-inflam) Ginsenosides Panaxosides Chikusetsusaponins Botogenin Diosgenin
CI: cardiac problems & HTN – ↑ Na retention and ↓K Aphrodisiac Adaptogen (antistress) Cortisone precursor
CYANOPHORE OR CYANOGENIC GLYCOSIDES (Bound Poisons) yeilds hydrocyanic acid as one of the products found in Rosaceae plants amygdalin is the most widely distributed derivatives of mandelonitrile (benzaldehyde-cyanohydrin) Cyanide-containing compounds: Prunasin, Laetrile/Vitamin B17, Amygdalin Amygdalin Amygdalase Mandelonitrile glucose Prunase Mandelonitrile + Glucose
*Amygdalase + Prunase = EMULSIN
Benzaldehyde + HCN
Bitter Almonds Wild Cherry prunus virginiana, wild black cherry tree Apricot Pits Cassava
Origin Amygdalus communis Prunus serotina
Active Constituent Amygdalin Prunasin
Prunus armeniaca, Rosaseae Manihot esculenta
Laetrile/Vit. B17 Mannihotoxin
Use sedative expectorant
controversial treatment for sickle cell anemia (antiCA)
GLUCOSINATES/ISOTHIOCYANATES (From family Cruciferae/Brassicaceae) Black Mustard White mustard Sinapis nigra Sinapis alba Brassica nigra Brassica alba Sinigrin Sinalbin myrosin myrosin Allyl isothiocyanate Acrinyl isothiocyanate Local irritant and emetic, Rubefacient, vesicant, and condiment
Synonym Origin Active Constituent Uses
FLAVONOL
Rutin &Hisperidin Hesperitin & Naringen
(Vitamin P or Permeability Factors)
Tx of capillary bleeding secondary to capillary fragility Tx of symptoms of common colds
ALCOHOL
Salicin (Salix and Populus)
Salix purpurea Salix fragilis
Saligenin (salicyl alcohol) - antirheumatic (closely resembles salicylic acid)
ALDEHYDE
Vanilla
Vanilla plantifolia
Vanillin (4-hydroxy-3- methoxy benzaldehyde or methylprocatechuic aldehyde)
Other sources of Vanillin: Coniferin - glycoside present in cambium sap of pine trees Eugenol - phenol present in clove oil Lignin - by product of the pulp industry Gluco-vanillin (avenein) and glucovanillic alcohol hydrolyzed into glucose and vanillin and glucovanillic alcohol which is oxidized to vanillic aldehyde
PHENOL
Uva Ursi (Bearberry)
Arctotaphylos uvaursi
Arbutin – antiseptic and astringent
LACTONE GLYCOSIDES Coumarin
Cantharides
Psoralens (photosensitizing furocoumarins)
Origin Dicumarol, Dipteryx odorata Bishydroxycoumarin (tonka beans) Spanish flies, Russian flies, Blistering flies
Cantharis vesicatoria
Ammi majus
Use Anticoagulant
AC : Cantharidin Effects: Blisters – irritant, vesicant, rubefacient Priapism (used as aphrodisiac) Methoxsalen – repigmentation in vitiligo Trioxsalen
TANNINS
A group of complex phenolic compounds capable of combining with proteins Polypeptides that are difficult to separate because they do not crystallize Precipitates proteins from solutions and can combine with proteins, rendering resistant to proteolytic enzymes Medicinal use : astringent Industrial use : manufacture of leather tannin Skin and Hides Leather Tanning of leather CHEMICAL CLASSES OF TANNINS Hydrolyzable
Heating
Gallic acid Pyrogallol
Hydrolyzation Boil with HCl FeCl3 Test Br Water Lead Acetate Leather Type
Phenolic acids and Sugar Bluish black precipitate No precipitate Soluble Bloom
Tests for presence of Tannins: 1. Goldbeater test 2. Gelatin test Characteristics of Tannins 1. Acidic 2. Sharp puckering taste 3. Precipitates alkaloids 4. Precipitates proteins (tanning industry) 5. Astringents – GI and skin 6. Treatment of burns
Hamemelis Leaf Hazel leaves
Nutgall
Origin Hammemelis virginiana
Nonhydrolyzable/Condensed/Proanthocyan idin (from condensation of catechin and leucocyanidin) Catechol
Polymerization Plobaphenes (insoluble, red colored products) Greenish black precipitate Precipitate Tanner’s red
Tannins can precipitate: Proteins Alkaloids Glycosides Tannic acid – antidote for alkaloidal poisoning Universal antidote : Tannic acid - precipitant Activated charcoal - adsorbent Magnesium Oxide - cathartic
Active Constituent Hamamelitannin
Excrescence from the young twigs Tannic acid/Gallotannic acid of Quercus infectoria, Fagaceae Insect: Cynips tinctoria
Use Astringent Incorporated in hemorrhoidal preparations Tx: insect bites and stings Used in tanning industry Astringent Manufacture of inks
LIPIDS ester of long chain of fatty acids and alcohols Uses: SATURATED FATTY ACIDS emollients 10C Capric vehicles for IM injection – Corn Cottonseed Peanut Sesame 12C Lauric cathartic – castor oil 14C Myristic soap production 16C Palmitic (most abundant FA) increase caloric value – TPN 18C Stearic 20C Arachidic CLASSES OF LIPIDS 1. Fixed Oils - Long chain fatty acids + Glycerol o From vegetables o Liquid at room temperature (except theobroma) 2. Fats - Long chain fatty acids + Glycerol o From animals o Solid at room temperature (except cod liver oil)
UNSATURATED FATTY ACIDS 18:1 Oleic 18:2 Linoleic 18:3 Linolenic (dietary precursor of PGE) 18:4 Arachidonic (precursor of PGE) Vitamin F (essential FAs): Oleic, Linoleic, Linolenic
3. Waxes – long chain fatty acids + High MW alcohol such as cetyl or stearylalcohol 4. Sterols – alcohols containing cyclopentanophenanthrene nucleus (cholesterol) 5. Phospholipids (Phosphatides) – Ester consisting of glycerol in combination with fatty acids, phosphoric acid and nitrogenous compounds (Lecithin) 6. Glycolipids (Cerebrosides) – Substances isolated from the brain and various sources which on hydrolysis yield fatty acids, galactose and nitrogenous compounds (Phrenosin and kerasin)
Tests or constants based on the chemical constitution of the fatty acids: 1. Acid value or acid number # of mg. of KOH required to neutralize the free fatty acids in 1 g of substance Indicates the presence of free fatty acids 2. Saponification value , saponification number or Koettsdorfer number # of mg. of KOH required to neutralize the free acids and saponify the ester contained in 1 g. of substance serves to detect the presence of the glycerides of acids 3. Iodine number # of grams of iodine absorbed by 100g of the substance indicates the degree of unsaturation of the fatty acids Classification of Fixed oils base on Iodine Value 1 drying oils >120 Linseed, cod liver oil 2 semidrying 100-120 Cottonseed, sesame 3 nondrying oils < 100 Olive, almond
FIXED OILS Origin
Active Constituent
Use
Coconut Oil
Cocos nucifera
Lauric & Myristic acid
Solvent for IM injection
Palm Oil
Elaeis guincenss
Shortening, frying, soap & candle manu
Castor Oil
Ricinus communis
Ricin (toxic) Ricinine (alkaloid) Azeleic acid (anti-acne)
Stimulant cathartic (ricinoleic acid) from Tricinolein hydrolysis by lipase (duodenum) CI: Pregnancy Olive oil grades (extracted with): 1. First Grade Virgin – less pressure 2. Second Grade Virgin – more P 3. Technical Oil – hot water 4. Sulfur Grade – CS2; low quality 5. Tournant Oil – fallen, decomp fruits
Olive Oil Sweet oil
Olea europaea
Oleic acid
Peanut Oil Arachis Oil
Arachis hypogaea
Oleic acid, Linoleic acid
Solvent for IM injection
Rapeseed Oil Canola Oil
Brassica campestris Brassica napus
Erucic acid
Salad oil Shortening
Soybean Oil
Glycine soja
Linolenic Acid
Lecithin – useful in controlling deranged lipid and cholesterol metabolism. Stigmasterol – from lipid fraction of soybean; steroid hormone precursor
Cottonseed Oil
Gossypium hirsutum
Linoleic, Oleic, Palmitic Myristic, Arachidonic
Make substitues for lard, soap
Sesame Oil Teel oil, Benne oil
Sesamum indicum
Oleic acid Linoleic acid
Sesamol – phenolic constituent which owes the excellent stability of the oil produced by the hydrolysis of sesamolin
Prunus amygdalus
Oleic, Linoleic Palmitic, Stearic
Emollient
Almond Oil Persic Oil Apricot/Peach kernel oil
Prunus armeniaca Prunus persica
Corn Oil
Zea mays embryo
Safflower Oil
Carthamus tinctoria
Sunflower Oil
Helianthus annus
Linseed Oil Flaxseed oil
Linum usitatissimum
Theobroma Oil Food for the Gods
Theobroma cacao
Cocoa syrup, Beverage Cocoa butter – supp base
Ethiodized Oil Injection
Iodine addition product of ethyl ester of the fatty acids of poppy seed
Diagnostic aid
Solvent for IM injection Linoleic acid
Dietary supp (False claim: ↓ cholesterol) Alternative to corn oil and safflower oil
Linileic acid – inedible (drying oil in paint & varnish)
Linum means thread; usitatissimum means most useful
FATS Lanolin
Origin Wool of Ovis Aries
Cod Liver Oil - liquid animal fat
Gadus morrhua (fresh livers)
Undecylenic Acid
Pyrolysis of Ricinoleic acid from castor oil
Active Constituent Hydrous Lanolin: 25% water Anhydrous lanolin/wool fat: 0.25% water Myristic acid Palmitic acid
Use H2O absorbable ointment base Emollient Sodium morrhuate - sclerosing agent (varicose) Source of Vit. A and D Antifungal
WAXES – stiffening agents Spermaceti Jojoba Oil Beeswax Yellow wax Carnauba wax
Origin head of sperm whale, Physeter macrocephalus Simmondsia chinensis Honeycomb of Apis mellifera Copernicia prunifera
Active Constituent Synthetic Spermaceti (Cetyl Ester Wax)
Use Emollient, Cold cream
Eicosenoic acid Myricyl palmitate
Emollient Stiffening agent
Myricyl cerotate
Candles, wax varnishes
Prostaglandins – class of natural products with potent and diverse biological activities Lipid metabolites formed in the body from essential, unsaturated fatty acids from the diet. Linoleic – most important dietary precursor of the prostaglandins – converted by elongation and desaturation in the liver to arachidonic acid
Prostanoic acid – parent compound of all natural prostaglandins Elcosonoids – arachidonic acids and most of the metabolites contain 20 carbon atoms 3 Main Classes of Major Prostaglandins 1 Prostaglandin A 2 Prostaglandin E 3 Prostaglandin F
VOLATILE OILS (Ethereal oils/Essences) Physical Characteristics Possess characterisctic odor Evaporate when exposed to air High refractive index Optically active Immiscible in water but they can be sufficiently soluble to impart their odor in water May act as insect repellants or insect attractants May occur in specialized secretory structures: glandular hairs modified parenchymal cells oil tubes called vittae lysigenous or schizogenous passages Formed by:
– Labiatae Lamiaceae – Piperaceae – Umbelliferae Apiaceae – Pinaceae, Rutaceae
Decomposition of resigenous layer of cell wall Hydrolysis of certain glycosides
2 classes: Terpene derivatives Aromatic compounds
- via acetate-mevalonic acid pathway - via schikimic acid-phenylpropanoid route
Medicinal Uses: Carminative, Antiseptic , Antipruritic (camphor), Counterirritant (methyl salicylate) Fixed Oil Ester of Glycerol + Fatty Acid Can be saponified Permanent spot on brown paper Cannot be isolated by distillation Become rancid
METHODS OF OBTAINING VOLATILE OILS 1. Distillation a. Water distillation b. Water and steam distillation c. Steam distillation d. Destructive distillation
Volatile Oil Made up of terpenes Cannot be saponified No permanent spot on brown paper Can be distilled from natural source Resinify on long standing
- for those not injured by boiling (turpentine oil) - for those injured by boiling (clove oil, cinnamon oil) - for fresh plant drugs (peppermint, spearmint) - empyreumatic oils (heat without the access of air)
2. Enzymatic Actions – mustard oil 3. Expression a. Ecuelle b. Enfleurage
- rolling the fruit over a trough lined with sharp projections (citrus oils) - expression with the use of cold fat (perfume)
4. Extraction – using solvent systems based on volatile solvents (petroleum ether/benzene)
MEDICINAL AND COMMERCIAL USES 1. Fabrication of Perfumes
Top Notes Middle Notes Base Notes aka Fixatives
Definition Most volatile products Leave the skin readily Intermediate tenacity and volatility Low volatility and high tenacity
Examples Lemon oil, Lavender oil, Anise oil Thyme oil, Neroli oil, Rose oil Musk
Dried secretion from the preputial follicles of the male musk deer of Asia (Moschus spp)
Civet
A glandular secretion appearing in an outwardly discharging pockets of Civet cats (Paradoxurus hermaphroditus) Ambergris Most valuable material Pathologic product formed in the stomach of spermwhale when it feeds on squid or cattlefish Volatile oils generally consist of: Eloptene – hydrocarbon portion, liquid Stearoptenes – oxidized hydrocarbon portions, solid (generally obtained by freezing the oil)
CONSTITUENTS OF VOLATILE OILS Terpenes – natural products whose structures may be divided into isoprene units C5H8 Monoterpenes – most abundant in nature Sesquiterpenes Diterpenes Triterpenes
2 isoprene units 3 isoprene units 4 isoprene units 6 isoprene units
C10H16 C15H24 C20H32 C20H48
Phenylpropanoids – contain C6 phenyl ring with an attached C3 propane side chain – those in volatile oils are phenol or phenol ethers
BIOSYNTHESIS OF VOLATILE OIL CONSTITUENTS Isoprene units – building blocks for terpenes Synthetically active isoprene units: isopentyl pyrophosphate dimethylallyl pyrophosphate Geranyl pyrophosphate – C-10 precursor of terpenes Principal precursors of phenylpropanoid compounds: cinnamic acid p-hydroxycinnamic acid (p-coumaric acid) These compounds arise from phenylalanine and thyrosine, which in turn synthesized via shikimic acid pathway.
HYDROCARBON 1. Turpentine Oil (Spirit of Turpentine) BO : Pinus palustris and from other species of Pinnus Linne Use : Disinfectant, Deodorant, Counterirritant in Vicks Vaporub Rectified turpentine oil - rectified by distillation from an aqueous solution of NaOH Terpin hydrate/Terpinol/cis-p-menthane-1,8-diol hydrate - formed by action of nitric acid on rectified turpentine oil in the presence of alcohol - expectorant
ALCOHOL Peppermint Oil
Mentha piperita
Menthol
Japanese Peppermint Oil Cardamom Oil
Mentha arvensis Elettaria cardamomum
High menthol concentration than M. piperita but it has an inferior flavor Flavor, carminative
Coriander Oil
Coriandum sativum
Flavor, carminative
Rose Oil Otto of Rose Orange Flower Oil Neroli Oil Juniper Oil
Rosa gallica, R. damascena, R. alba, R. centifolia Citrus aurantium
Perfume
Juniperus communis
Flavor, diuretic in the OTC drug, Odrinil®
Cinnamomum loureirii
Flavoring, carminative, pungent aromatic. Antiseptic
Perfume, flavor
ALDEHYDE Cinnamon Oil Cassia Oil
Cinnamaldehyde Natural: cassia oil Synthetic: benzaldehyde + acetaldehyde (action of NaOH) Lemon Peel
Citrus limon
Limonene & Citral (neral & geranial)
Lemon Balm
Melissa officinalis
Citral
Orange Oil
Citrus sinensis
Limonene
Citronella Oil
Cymbopogon winterianus, C. nardus
Perfume, insect repellant
Hamamelis Water
Hamamelis virginia
Astringent in the OTC hemorrhoid preparations
KETONE Camphor
Cinnamomun camphora Carvone
Antipruritic
Synthetic: racemic Natural: dextrorotatory (+)Carvone has the same odor as that of caraway
Flavor, carminative Gums, toothpaste, mouthwash
Spearmint
Mentha spicata
Caraway Oil
Carum carvi
(+)Carvone
Flavor, carminative
Buchu
Barosma betulina, B. Crenulata B. Serratifolia
*Diosphenol
Diuretic in OTC drugs for menstrual problems, Fluidex, Odrinil
Wormwood Oil Absinthe Oil
Artemisia absinthium
Thujone
Counterirritant in Absorbine Jr.
Cedar Leaf Oil
Thuja accidantalis
Thujone, Fenchone
Counterirritant in Vicks Vaporub
Clove Oil
Eugenia caryophyllus
Dental analgesic
Thymol
Thymus vulgaris
CREOSOTE Beachwood creosote
Fagus grandiflora
Eugenol (4-allyl-2methoxyphenol) Thymol - synthetically from m-cresol or p-cymene Gualacol, Creosol
JUNIPER TAR Cade oil
Pinus palustris
Myrcia oil
Pimenta racemosa
PHENOL VOLATILE OILS Antifungal Antibacterial disinfectant in Dewitt’s Toothache drops, expectorant in Creomulsin Antieczematic and anti-psoriasis (Packer’s Pine Tar, Polytar), Expectorant
PHENOLIC-ETHER VOLATILE OILS Biosynthesis of Phenolic Ethers – takes place from phenylalanine (schikimic acid-phenylpropanoid pathway) Methionine – methyl donor for methoxylation reaction Nutmeg Myristica Oil Fennel Oil
Myristica fragrans
Anise Oil
Pimpinella anisum (anise or aniseed), Illicium varum (chinese anise or star anise)
Foeniculum vulgare
Safrole Myristicin Anethole
Flavoring, Carminative
Anethole
Flavoring, Carminative
OXIDE VOLATILE OILS 1. Eucalyptus Oil/Cineole BO : Eucalyptus globulus AC : Cineole/Eucalyptol/Cajuputol Use : flavor, antiseptic, diaphoretic, expectorant 2. Ascaridol
Flavoring, Carminative
ESTER VOLATILE OILS Biosynthesis of Esters - terpene esters are generally formed from the respective alcohols by reaction with aliphatic acid moieties (commonly acetic acid) Gaultheria Oil Wintergreen/Betula/ Sweet birch
Gaultheria procumbens Betula lenta
Lavender Oil
Lavandula angustifolia
Perfume
Pine Needle Oil Dwarf pine needle oil
Pinus mugo
Perfume
Mustard Oil
Brassica nigra
SESQUITERPENES 1. Chamomile 2. Artemisinin Quinghaosu 3. Valerian 4. Feverfew DITERPENES 1. Taxol 2. Ginkgo
Methylsalicylate
Allyl isothiocyanate Acrinyl isothiocyanate
Flavor (aromatic cascara sagrada fluidextract local irritant, antiseptic, antirheumatic
Rubefacient in Musterolew
Matricaria chamomila Artemisia annua
Carminative, spasmolytic Antimalarial
Valeriana officinalis Tanasetum parthenium
Sedative and anxiolytic Antipyretic, migraine tx
Taxus brevifolia Ginkgo biloba
Antineoplastic Increases blood fluidity
TRITERPENES Quassinoids – pediculocide 1. Neem Tree Azadirachta indica
Antifeedant properties (mosquito repellant)
RESIN AND RESIN COMBINATIONS
Amorphous products with complex chemical nature Hard transparent or translucent and when heated they soften and melt
Resin Combinations: 1. Oleoresins 2. Oleo-gum-resins 3. Balsams 4. Glucoresins or glycoresins
– resins + volatile oils – resins + volatile oils + gum – contain cinnamic acid, benzoic acid, or both – glycosidal combinations (ex. jalap and podophyllum)
Resin Acids (abietic acid, copaivic & oxycopaivic acid, commiphoric acid) • contain large proportion of oxyacids, usually combining the properties of carboxylic acids and phenols • resinates – metallic salts of resin acids (some are used in soaps and varnishes) Resin Alcohols (benzoresinol, storesinol) • do not give a tannin reaction with iron salts • occur in free state and as esters in combination with simple aromatic acids Resinotannols (aloeresinotannol, peruresinotannol, siaresinotannol and sumaresinotannol, and toluresinotannol) • gives a tannin reaction with iron salts Resenes – B-complex natural substances devoid of characteristic chemical properties Glycoresins – yields sugars and complex resin acids on hydrolysis Pharmaceutic Resins are usually obtained by: - extracting with alcohol & precipitating the resins in water (jalap & podophyllum) - separating the oil from oleoresin by distillation (copaivic resin) - collecting the natural product throught natural or artificial punctures (mastic)
RESINS Other Name
Origin
Rosin
Colophony
Podophyllum
Mayapple Mandrake
Eriodictyon
Yerba santa
Jalap
Jalap root
Exogonium purga
Mastic
Mastiche, Mastich
Pistacia lentiscus
Kava
Kava-kava
Piper methysticum
Cannabis
Indian hemp Marihuana, Pot
Cannabis sativa
Constituent
Pinus Palustris Podophyllum peltatum Indian Podophyllum – rhizome of P. emodi Eriodictyon californicum
Use Stiffening agent
Podophyllin
Drastic purgative Antimitotic (papilomas) Disguise Quinine bitterness Stimulating expectorant (1g)
Jalap resin
Hydragogue cathartic Dental varnish to seal cavities
Hashish
Centrally acting muscle relaxant Antipyretic, local anaesthetic THC – euphoric agent Cannabidiol – manuf of rope
OLEORESINS Turpentine
Other Name Gum turpentine Gum thus
Origin
Constituent
Pinus palustris
Counterirritant
Capsicum
Cayenne pepper
Capsicum frutescens
Ginger
Zingiber
Zingiber officinale
White Pine Copaiba
Pinus srobus Balsam of Copaiba
Copaifera spp.
Use
Capsaicin
Coniferin
Irritant, carminative, Rubefacient, Stimulant, Condiment Flavor, condiment, stimulant, carminative, ginger ale Expectorant Genitourinary disinfectant, Diuretic, Expectorant, Laxative
OLEO-GUM-RESINS 1. Myrrh/Gum myrrh 2. Asafetida/Devil’s Dung
Commiphora molmol
Astringent, Embalming
BALSAMS Storax Liquid Storax Styrax Peru Balsam Tolu Balsam
Origin Liquidambar orientalis
Use Pharmaceutic aid for compound benzoin tincture Stimulant, Expectorant, Antiseptic
Myroxylon pereirae Myroxylon balsamum
Local protectant and rubefacient, Antiseptic Pharmaceutic aid in compound benzoin tincture Expectorant, Flavoring in syrups, confectionery, chewing gum, perfumery Antiseptic Compound Benzoin Tincture (benzoin, aloe, storax, tolu) Benzoic acid (synthetic product; first obtained by sublimation from Sumatra benzoin; antifungal)
occurs as plastic solid that gradually hardens
Benzoin
Styrax benzoin
ALKALOIDS
Bitter, basic nitrogenous compounds, sparingly soluble in water Most of them end in –ine All are solids except: o Coniine o Nicotine o Sparteine Form double salts with compounds of mercury, gold, platinum, and other heavy metals
Alkaloidal reagents/precipitants: 1. Mayer’s Mercuric potassium iodide 2. Marmers Potassium-cadmium iodide 3. Dragendorff’s Potassium-bismuth iodide 4. Wagner’s Iodine TS 5. Scheibler’s Phosphotungstic acid 6. AuCl 7. Valser’s KI and mercuric iodide 8. Tannic acid 9. Hager’s Picric acid 10. Sonnenscheins Phosphomolybdic acid
White or slightly yellow ppt. White ppt. Orange Reddish brown or red brown ppt.
White ppt. Yellow
CHARACTERISTICS OF ALKALOIDS 1. 2. 3. 4. 5. 6. 7. 8.
Free alkaloids - sparingly soluble in H2O + acids --> salts + salts of heavy metals --> highly insoluble precipitates nitrogenous, physiologically active alkaloidal salt + Na2CO3 --> free base Solid alkaloid - white, soluble or slightly soluble in H2O, soluble in organic solvents Pure alkaloids - insoluble in water, soluble in organic solvents alkaloids + acids = alkaloidal salts (soluble in water)
Alkaloid yielding plants: 1. Leguminosae 2. Solanaceae 3. Rubiaceae 4. Ranunculaceae 5. Papaveraceae 6. Berberidaceae
Pharmacologic Action of Alkaloids 1. Analgesic and narcotics 2. Central stimulant 3. Mydriatics 4. Miotics 5. Cause a rise in B.P 6. Excessive hypertension
-morphine, codeine - strychnine, brucine - atropine - physostigmine, pilocarpine - ephedrine - reserpine
The names of the alkaloids are obtained in various ways: 1. generic name (Hydrastine, Atropine) 2. specific name (Coccaine, Belladona) 3. common name (Ergotamine) 4. physiologic activity (Emetine, morphine) 5. discoverer (Pelletietine) FUNCTIONS OF ALKALOIDS IN PLANTS 1. poisonous agents – protect plants againts insects & herbivores 2. end products of detox representing metabolic locking up of compounds otherwise harmful to the plant 3. Regulatory growth factor 4. Reserve substance capable of supplying nitrogen or others
PYRIDINE-PIPERIDINE Origin Nicotine
Use
Nicotiana tabacum
Nicotine (smoking deterent)
Areca
Betel nut
Areca Catechu
Arecoline Anthelminthic Tannin content causes esophageal CA
Lobelia
Indian tobacco
Lobelia inflata
Lobeline (smoking deterent)
Origin Atropa belladonna Atropos – fate that cuts the thread of life
Use Parasympathetic depressant Adjunct in tx of peptic ulcer
TROPANE/SOLANACEOUS
Belladonna
Deadly nightshade
Hyoscyamus
Henbane
Hyoscyamus niger
Hog + Bean toxic to swine
Stramonium
Jimson Weed Jamestown Weed
Datura stramonium D. metel (Talumpunay/Thorn apple)
Treatment of asthma (vapor)
Mandragora
European mandrake
Mandragora officinarum
Has folkloric uses
Cocaine
Coca
Erythroxylum coca
Psychomotor stimulant with a strong abuse potential, vasoconstrictor
Principal Solanaceous Alkaloids: 1. Atropine o Antispasmodic o Antisialogogue – decrease production of secretion o Mydriatic and cycloplegic o Antidote for cholinesterase inhibitors 2. Scopolamine or Hyoscine o Hyoscyamus niger o Treatment of motion sickness o Trans-scoop or transderm Scop – 4 hours before anti-emetic effect
QUINOLINE Cuprea o Remijia purdieana Cinchona or Peruvian bark o Cinchona succirubra (Red cinchona) Cinchona calisaya (Yellow cinchona) o Quinidine - anti-arrthythmic Quinine - antimalarial o Identification of the quinine /quinidine by Thalleioquin test
ISOQUINOLINE – emerald green color of thalleioquin (Joseph Caventou with Pelltier) Other Name Ipecac
Origin
Constituent
Cephalis ipecacuanha
Emetine
Use Ipecac syrup – emetic Fluidextract – 14x more potent Ipecac + Opium - diaphoretic
Sanguinaria
Bloodroot
Sanguinaria canadensis
Sanguinarine
Expectorant & emetic
Tubocurarine
Curare
Strychnus toxifera
Tubocurarine
Skeletal muscle relaxant
Hydrastis
Golden seal
Hydrastis canadensis
Hydrastine
Astringents in inflammation of the mucous membrane
Opium
Stone of immortality
Papaver somniferum
Alkaloids of Opium 1. morphine 2. codeine methyl morphine 3. heroin diacetylmorphine 4. Papaverine 5. Hydromorphine 6. Hydrocodone 7. Apomorphine 8. Narcotine/Noscapine 9. Paregoric 10. Dover’s powder
Stimulate and depresses CNS
- most abundant, most important - most widely used; antitussive - hallucinogen - relief of ischemia & arrhythmias
- emetic - ANARCOTINE, antitussive - camphorated opium tincture - Ipecac + opium
IMIDAZOLE Pilocarpine (Pilocarpus, Jaborandi) BO : Pilocarpus jaborandi Use : Cholinergic drug used in the Tx of glaucoma; miotic
STEROIDAL Veratum Viride (American or Green hellebore) BO : Veratrum viride Uses : hypotension, cardiac depressant, Black hellebore – cardiac stimulant White Hellebore (European hellebore) BO : Veratrum album Use : Hypotensive, Insecticide (crude drug)
INDOLE Other Name Rauwolfia serpentina
Catharanthus
Vinca Chichirica
Nux Vomixa
Constituent Reserpine
Catharanthus roseus
Rescinnamine Deserpidine (II desmethoxyreserpine) Yohimbine - TX: impotence (Serpasil) Vincristine and Vinblastine antineoplastic/oncolytic Strychnine – toxic central stimulant Brucine – alcohol denaturant Physostigmine/Eserine - Tx glaucoma, miotic
Strychnos nux-vomica
Physostigmine Ergot
Origin Rauvolfia serpentina
Calabar bean Ordeal bean Rye ergot Secale cornutum
Physostigma venenosum Claviceps purpurea
Use Snake bites Insanity (Psychotherapy) Hypotensive Sedative, Tranquilizing
Ergonovine – oxytocic Ergotamine – migrane Lysergic acid Diethylamide (LSD) most specific and most active hallucinogen discovered by A. Hoffman in 1943
ALKALOIDAL AMINES Constituent Ephedrine
Ephedra, Mahuang
Colchicine
Use
Ephedra sinica
Sympathomimetic
Colchicum autumnale
Plant genetics: doubles the chromosomes Gout suppressant: Acute
Khat
Abyssinian tea
Catha edulsis
Cathinone - alleviate sensation of hunger and fatigue
Peyote
Mescal buttons
Lophophora williamsii
Mescaline (3,4,5 trimethoxy-ẞ-phenylethylamine) Hallucinogen and euphoric
PURINE OR METHYLXANTHINES 1. Caffeine 1,3,7 trimethylxanthine o Does not react with or ppt with alkaloidal reagnents o Kola (dried cotyledon of Cola nitida) o Cofee bean (dried seeds of Coffea arabica) o Guarana (Paullinia cupana) o Mate/Paraguay tea (Ilex paraguariensis)
Caffeine is detected by means of a Murexide test purple color
2. Theophylline 1,3 dimethylxanthine o Camella sinensis o Treatment of bronchial asthma, Tocolytic agent o Aminophylline – semisynthetic theophylline derivative 3. Theobromine 3,7 dimethyl xanthine o Theobroma cacao o Diuretic in cardiac & pulmonary edema (preferred over caffeine - little action on the CNS)
BIOLOGICS
Any product derived from a living plant or animal source Any virus, therapeutic serum, toxin, antitoxin or analogous product Not chemotherapeutic nor an antibiotic Uses of biologics: o Prophylactic or Preventive Therapy o Therapeutic or Curative Measures
1. 2.
Types of Immunity Natural (Innate) Immunity Acquired Immunity Active Immunity a. Naturally Acquired Active b. Artificially Acquired Active Passive Immunity a. Naturally Acquired Passive b. Artificially Acquired Passive
2 GENERAL CATEGORIES Antigen provokes the immune response Chemically: Antigens are usually protein Biologically: causes formation of antibodies when introduced to tissue Physically: H molecular weight (more than 10,000 daltons) 2 properties: Immunogenicity – capacity to induce Ab formation Specificity
Antibody predominant in the serum fraction of the blood 4 fractions obtained when serum proteins are separated by electrophoresis: 1. serum albumin 2. alpha globulin 3. beta globulin 4. gamma globulin Immunoglobulins/Antibodies/Serum Globulin Ab that occur predominately in the gamma globulin fraction Attacks antigens 5 subclasses of Ig: IgA External secretions (tears, saliva, respiratory, GI) IgD Found in surface of B lymphocytes (no fxn yet) IgE Allergy IgG Smallest (passes through placenta) IgM Largest First Ig to be formed during infection (newborn)
Epitope simplest form of antigenic determinant present on a complex antigenic molecule Haptens compounds with m.w lower than 10,000 daltons partial antigens lack immunogenicity but can attach to host proteins to form a complete antigen
4 subsets of T cells
Cell-mediated immunity: TC cells – cytotoxic, attack cell membranes bearing their specific antigen TD cells – delayed hypersensitivity cells – releases lymphokines, which recruit & activate macrophages Immunoregulatory: TH (helper) cells – interaction with B cells is essential for optimal humoral immunity TS (supressor) cells – diminish activity of B cells
Macrophages and Lymphocytes B cells T cells
Major cellular components of immune system
originate in bone marrow but depend on thymus gland for differentiation cellular immunity, delayed hypersensitivity sentinels of immune surveilance against cancer and mediators of graft rejection
B memory cells
some progeny of the selected clones that remain as circulating B cells serve as immune system’s memory
Plasma cells
other member of selected B-cell clones grow larger, stop reproduction, & continuously secrete large quantities of Ab
Orgin of serum antibodies (humoral immunity)
VACCINES
AE: fever, malaise, soreness at injection site rubella vaccine: arthralgia and arthritis pertussis vaccine: convulsions “swine flu”, 1976: Guillain-Barre syndrome
living, attenuated, or killed viruses, killed rickettsiae, or attenuated or killed bacteria must be induced prior to infection (prophylactic) – exception: rabies vaccination Nonliving vaccines provide protection for a limited time: typhoid fever, cholera, plague, typhus With living agents (single vaccination): measles, rubella, or mumps vaccine Multiple immunizations: polio CI: immunosupressed patients
VIRAL VACCINES
• cultures: chick embryo, monkey kidney, or human diploid cells Description Grown on Smallpox Vaccine (Dr. Edward Jenner) Living virus of vaccinia (cowpox) Skin of a vaccinated bovine calf Rabies Vaccine Sterile lyophilized preparation of: Human diploid embryo lung tissue Human Diploid Cell Rabies Vaccine (whole virion) Whole virion (Wistar rabies (HDCV) Human diploid cell cultures (subvirion) virus) ® ® (Imovax , WYVAC ) Subvirion rabies virus (Pasteur- *Brain tissue – formerly used for preparing the vaccine; myelin Pasteur was able to “fix” rabies derived Pitman-Moore virus) (“paralytic factor”) virus Yellow Fever Vaccine Attenuated strain of living yellow Living embryo of domestic fowl (YF-VAX®) fever virus (Vector: Aedes mosq) (Gallus domesticus) Influenza Virus Vaccine Sterile, aqueous solution of Extra-embryonic fluid of influenza (Fluzone®, Fluogen®) suitably inactivated influenza virus virus-infected chick embryo types A and B high strain specificity and genetic instability (reevaluated regularly) Poliovirus Vaccine Inactivated Sterile suspension of inactivated Rhesus monkey kidney tissues IPV, Salk poliomyelitis virus types 1, 2 and 3 Type 1 (Brunhilde) poliovirus – responsible for major epidemics Type 2 (Lansing) poliovirus – sporadic Type 3 (Leon) poliovirus – less frequent epidemics Improved strains: Type 1 Mahoney strain Type 2 MEF-1 strain Type 3 Saukett strain
Poliovirus Vaccine Live Oral (Orimune®) Trivalent Oral Polio Vaccine (TOPV)
Landsteiner and Popper – first transmitted poliovirus John F. Enders – originated a method of cultivating poliovirus Jonas Salk – perfected the roller-tissue method, as well as the detoxified form of vaccine
Preparation of one or a combination of the 3 types of live, attenuated polioviruses
Monkey kidney tissue
Measles virus vaccine live Rubeola vaccine (Attenuvax®) Rubella virus vaccine live (Meruvax II®) - For German measles, CI:Pregnancy
Attenuated viruses derived from the original Edmonston B strain Wistar Institute RA 27/3 strain
Chick embryo tissue
Mumps Virus Vaccine Live (Mumpsvax®) Hepatitis B Vaccine (Heptavax-B®)
B-level Jeryl Lynn strain chemically inactivated hepatitis B surface antigens (HbsAg) particles
Chicken embryo tissue plasma of healthy chronic HbsAg carriers by plasmaphresis
Albert Sabin, Harold Cox, Hilary Koprowski – developed procedures for manufacturing the vaccine (separately)
Human diploid cell tissue
Combination Virus Vaccines o Live measles and rubella (M-R-Vax II), Live rubella and mumps (Biavax II), Live measles, mumps, and rubella (M-M-R II)
RICKETTSIAL VACCINES G : chick embryos or monkey kidney tissue cultures Use : murine typhus, tsutsugamushi fever, rickettsial diseases, epidemic typhus
BACTERIAL VACCINES
suspensions of attenuated, more commonly, killed pathogenic bacteria in isotonic NaCl soln “S”/smooth strains are more antigenic than “R”/rough strains
Typhoid Vaccine (Enteric vaccine)
Killed Salmonella typhi (Type 2)
Cholera Vaccine
Killed Vibrio cholerae (Inaba & Ogawa strains)
Plague Vaccine
Killed Yersinia pestis (Reservoir: rats | Vector: fleas)
Pertussis Vaccine
Killed Bordetella pertussis Adsorbed Pertussis Vaccine – pertussis vaccine + of AlOH3 or Al2(PO4)3
Tuberculosis Vaccine (BCG Vaccine)
Dried, living M. Tuberculosis(Calmette-Guerin strain)
Meningitis Vaccine
Capsular polyssacharides for Neisseria meningitidis (A, C, Y, and W-135)
Pneumococcal Vaccine Polyvalent
Polysaccharide antigens from Streptococcus pneumoniae
Haemophilus b Polysaccharide Vaccine
Capsular polyvalent polysaccharide of Haemophilus influenzae type b (Hib)
TOXINS AND TOXOIDS o o o o o
Toxins – (exotoxins) bacterial waste products that are considered poisonous to the animal body Toxoid – toxin whose toxicity has been inactivated or suppressed either by chemical (formalin) or heat Act as antigens because they stimulate certain cells of the body to produce antitoxins Culture medium: beef broth medium Clostridium botulinum – source of the most poisonous poison Fluid Toxoids - formaldehyde (reduces or eliminates toxic properties w/o affecting antigenicity) - induces artificial active immunity Adsorbed Toxoid - precipitated or adsorbed with alum, aluminum hydroxide, or aluminum phosphate - slower release of antigen, subsequent production of higher & more prolonged Ab titers - more prone to produce local reactions at the injection site
ANTITOXINS (From blood of toxin-immunized animals, usually horses) o o
Standardized in terms of “antitoxin units” Admin: prepare a syringe containing epinephrine injection and torniquet to counter anaphylactic reactions
Diphtheria Antitoxin Tetanus Antitoxin Botulism Antitoxin type A, B, E strains
Use Passive immunity, curative Treatment & prophylaxis of tetanus if Tetanus Ig is not available (passive immunity) (multivalent) treat all cases of toxemia caused by types of botulinus bacteria used
VENOMS AND ANTIVENINS (From blood of venom-immunized animals, usually horses) o o
Venoms – poisonous excretions produced by animals; equivalent to exotoxins in bacteria Snake venins or venoms – obtained by holding a poisonous snake over a conical glass container covered with a sheet of thin rubber
Antivenin (Crotalidae) Polyvalent Antivenin Spider-Bite Antivenin
Synonym North and South American antisnakebite serum
North American coral snake antivenin Antivenin (Latrodectus mactans) Black widow spider antivenin
Against venom of Crotalus atrox (Western diamondback) C. adamanteus (Florida diamondback) C. durissis terrificus (S. American rattlesnake) Bothrops atrox (S. Amarican fer-de-lance) Micrurus fulvius (eastern coral snake) M. fulvius tenere (Texas coral snake) Latrodectus mactans (black widow spider)
ANTISERUMS (From blood of bacteria/virus-immunized animals, usually horses) Antirabies Serum (more effective if administered with rabies vaccine) D : sterile, nonpyrogenic solution containing antiviral substances From : blood serum or plasma of a healthy horse immunized against rabies by vaccination
IMMUNE GLOBULINS (From immune humans (survived an attack or immunized) Immune Globulin Immune serum globulin Immune globulin intramuscular Gamma globulin
Use Prophylactic in chickenpox, hepatitis A, and other diseases Immune Globulin Intravenous/IGIV provides immediate Ab levels tx of immunodeficiency syndrome
Pertussis Immune Globulin
Prophylaxis and treatment of pertussis
Tetanus Immune Globulin
Passive immunization against tetanus in individuals with wounds that may have been contaminated
Rabies Immune Globulin
Used with rabies vaccine (best postexposure prophylaxis)
Hepatitis B Immune Globulin Varicella-Zoster Immune Globulin
Restricted to immunodeficient individuals
RH0 (D) Immune Globulin
For unsensitized Rh-negative women who give birth to RH0 (D)- or Dupositive infant
Lymphocyte Immune Globulin
Lymphocyte selective immunosuppresant
DIAGNOSTIC ANTIGENS
positive response: localized, well-defined wheal accompanied by erythema From Human or bovine strains of tubercle bacillus
Tuberculin Old Tuberculin Purified Protein Derivative of Tuberculin Histoplasmin Coccidioidin Diphtheria Toxin Mumps Skin Test Antigen
Positive Response redness or inflammation
M. tuberculosis
inflammation and palpable induration or edema (5 mm)
M. tuberculosis (free from protein)
palpable induration (10 mm or more)
Histoplasma capsulatum (mycelial phase) Fungus Coccidioides immitis Corynebacterium diphtheriae (nlt 400 MLD/min lethal doses) Formaldehyde-inactivated mumps virus grown on extra-embryonic fluids of the mumps virus-infected chicken embryo
circumscribed area of redness (≥1 cm) erythema (at least 1.5 cm)
BIOLOGICS RELATED TO HUMAN BLOOD Whole Blood (human) Red Blood Cells Plasma Protein Fraction (human) Thrombin
From donor (+ citrate/heparin as anticoagulant) Whole blood minus plasma Selected proteins derived by fractionating material (source blood plasma, or serum) Sterile protein from prothrombin (bovine) + thromboplastin in the presence of calcium
Blood replenisher Blood replenisher in anemia Blood volume restoration (in shock) Hemostatic
Antihemophilic Derivatives – control of 2 types of hemophilia Antihemophilic factor
Antihemophilic factor IX complex Albumin Human
sterile, freeze-dried concentrate of human antihemophilic factor (prepared from the factor VIII-rich cryoprotein fraction of human venous plasma) dried plasma fraction comprising coagulation factors IX, II, VII, X sterile, nonpyrogenic preparation of serum albumin obtained by fractionating material (source blood plasma, serum, or placentas) from healthy human donors
Hemophilia A (classic hemophilia) Prevent dangerous bleeding or to perform surgery blood-volume supporter
Radio-Iodinated Serum Albumins contains serum albumin iodinated using mild conditions with either 125I or 131I sterile, buffered, isotonic solutions prepared to contain nlt 10 mg of radio-iodinated normal human albumin per ml & adjusted to provide nmt 1 millicurie of radioactivity per ml Iodinated 125I albumin injection and Iodinated 131I albumin injection Iodinated 131I aggregated injection
diagnostic aid to determine blood volume and cardiac output diagnostic aid for determination of pulmonary clearance
HERBS AND “HEALTH” FOODS
Natural – identifies only a source, not necessarily degree of superiority or inferiority Organic – the produce was grown under conditions utilizing only natural fertilizers, no pesticides
Alfalfa Aloe Angelica Apricot Pits Arnica Asafetida Aveloz Black Cohosh Blessed Thistle Blue Vervain Boneset Borage Bran Broom Buchu Burdock Butcher’s-Broom Calamus Canaigre Catnip Chamomile Chaparral Chicory Cholecystokinin Cocillana Collinsonia Coltsfoot Comfrey Cucurbita Seed Damiana Devil’s Claw Echinacea Eleuthero Evening Primrose Eyebright Fenugreek Feverfew Fo-ti-tieng Garlic Onion Gentian ( Ginseng Glucomannan Glycyrrhiza Goldenseal Gotu Kola
lucerne
gum asafetida, devil’s dung killwart
wild hyssop common borage Scotch broom lappa box holly sweet flag wild red American ginseng
creosote bush CCK stoneroot farfara
Cone/purple cone flower Siberian ginseng
Vitamin X
gentian root Konjac mannan licorice Hydrocotyle, Indian pennywort
Medicago sativa A. barbadensis(Aloe vera) or Curacao, A. spicata (Cape aloe) Angelica archangelica Prunus armeniaca Arnica montana Ferula assafoetida, F. rubricaulis, F. Foetida Euphorbia heterodoxa Cimicifuga racemosa Cnicus benedictus Verbena hastata Eupatorium perfoliatum Borago officinalis Triticum aestivum Cytisus scoparius Barosma betulina, B. crenulata, B. Serratifolia Arctium lappa Ruscus aculeatus Acorus calamus Rumex hymenosepalus Nepeta cataria Matricaria chamomilla (German), Anthemis nobilis (Roman) Larrea tridentata Cichorium intybus secreted by the duodenal mucosa Guarea rusbyi Collinsonia canadensis Tussilago farfara Symphytum officinale Cucurbita pepo, C. maxima, C. moschata Turnera diffusa Harpagophytum procumbens Echinacea angustifolia Acanthopanax senticosus/Eleutherococcus s. Oenothera biennis Euphasia officinalis Trigonella foenumgraecum Chrysanthemum parthenium Centella asiatica, Gillena trifoliata (meadowsweet), C. nitida Allium sativum Allium cepa Gentiana lutea Panax quinquefolius, P. Pseudoginseng Amorphophallus rivieri Hydrastis canadensis Centella asiatica
Hawthorn Hedge Hyssop Hibiscus Honey Hops Horehound Horse Chestnut Horsetail Hydrangea Hyssop Kelp Lecithin Life Root Linden Flowers Lovage Marigold Mistletoe Mormon Tea Muira Puama Oregano Pangamic Acid Parsley Passiflora Pau d’ Arco Pennyroyal Poke Root Pollen Propolis Red Bush Tea Rose Hips Royal Jelly Sarsaparilla Sassafras Schisandra Senega Snakeroot Senna Spirulina Super Oxide Dismutase Tamarind Tarragon Tienchi Tonka Beans L-Tryptophan Turmeric Valerian Wild Lettuce Wormwood Yarrow Yohimbe Yucca
Sudanese tea mel homulus
golden ragwort
American or European mistletoe Mexican/teamster/squaw tea, popotillo potency wood wild marjoram Ca pangamate, pangamic acid, vit B15
taheebo, ipe roxo
bee glue rooibos tea
sassafras bark schizandra senna leaves SOD
titnchi-ginseng, sanchi
midfoil
Crataegus monogyna Gratiola officinalis Hibiscus sabdariffa Apis mellifera Humulus lupulus Marrubium vulgare Aesculus hippocastanum Equisetium arvense Hydrangea arborescens Hyssopus officinale Macrosystis, Nereocystis, and Laminaria spp. Phosphatide mixture that yield α- or β-glycerophosphoric acid, fatty acids, and choline on hydrolysis Senecio aureus Tilia species Levisticum officinale Calendula officinalis Phoradendron tomentosum, P. serotinum, flavescens Ephedra nevadensis Ptychopetalum olacoides, P. uncinatum Origanum vulgare blood abnormalites, asthma, emphysema, alcoholism Petroselinum crispum Passiflora incarnata Tabebuia impetiginosa Phytolacca americana microspores of seed-bearing plants natural antibiotic Aspalathus linearis Rosa canina secretion from the paired salivary glands of Apis mellifera Smilax aristolochiaefolia, S. regelii, S. Febrifuga Sassafras albidum Schisandra chinensis Polygala senega Cassia spp. Leaflets Spirulina maxima metal lipoprotein from the liver or RBC of ox, Bos taurus Tamarindus indica Artemisia dranunculus Panax notoginseng Dipteryx odorata sleep-onset insomnia Curcuma longa Valeriana officinalis Lactuca virosa Artemisia absinthium Achillea millefolium Pausinystalia yohimbe Yucca spp.
BIOCHEMISTRY/MOLECULAR BIOLOGY Parts of a Cell basic functional and structural unit of life 1. CELL MEMBRANE 1. Phospholipds 2. Glycoproteins and Glycolipids 3. Cholesterol 4. Arachidonic Acid
CELL WALL Plants Cellulose Bacteria Peptidoglycan Fungi Chitin
2. ORGANELLES 1. Mitochondrion - powerhouse of the cell; produces ATP (energy)
2. Ribosomes
- protein synthesis Prokaryote: 30s, 50s = 70s Eukaryote: 40s, 60s = 80s
3. Lysosomes
- suicide bag of the cell - has enzymes and free radicals (when released, will cause APOPTOSIS) Red blood cells – 120 days *Hemolytic anemia – <120
4. Endoplasmic Reticulum (ER) o Smooth ER - lipid synthesis o Rough ER - protein synthesis 5. Golgi Apparatus - packaging and storage of substances in the cell
3. NUCLEUS – control center of the cell 1. Chromosomes - tightly coiled DNA strands (46 chromosomes) 2. Nucleolus - site of ribosome assembly 3. Nuclear Membrane
Trisomy 21 (Down Syndrome) Fetal Hydantoin Syndrome - Caused by phenytoin
CARBOHYDRATES o o o o
Polyhydroxyaldehydes and polyhydroxyketones Aldehyde or ketone alcohols that contain C, H, O The H and O has the same ratio as that of water, thus they are named as carbohydrates First products of photosynthesis
MONOSACCHARIDES Sugars that cannot be hydrolyzed further Characterized by the number of C atoms in the molecules Hexoses – most important 1. Glucose Aldohexose Dextrose, Blood sugar, Grape sugar, Physiologic sugar
Sucrose is a nonreducing sugar Glucose and Fructose are invert sugars. Enzyme: invertase
Tests for Hexoses
2. Fructose Ketohexose Reducing sugar Fruit sugar; sweet fruits and honey aka Levulose, the sweetest monosaccharide
1. 2. 3. 4.
Glucose Fructose Galactose Mannose
Moore’s Seliwanoff’s Mucic Acid Osazone Test
3. Galactose – readily absorbed in the intestines; biosynthesized in mammary glands 4. Mannose Pentoses 1. Arabinose 2. Ribose 3. Deoxyribose
DISACCHARIDES 1. Sucrose 2. Maltose 3. Cellybiose 4. Lactose
- found in Gum Arabic/Acacia - found in RNA - found in DNA
- Glu + Fru - Glu + Glu (α-1,4) - Glu + Glu (β-1,4) - Glu + Gal
OLIGOSACCHARIDES 1. Dextrin - product of starch degradation POLYSACCHARIDES/GLYCANS Homopolysaccharides Starch α-1,4 / α-1,6 Glycogen α-1,4 and α-1,6 Cellulose β-1,4 Chitin NAG
Heteropolysaccharides Hyaluronic acid Dermatan (skin) Keratan (nails) Agarose (seeweeds) Peptidoglycan (bacterial cell wall)
Schweitzer’s Reagent: only reagent that can dissolve cellulose
Epimers (isomers that differ in only 1 C) Epimers of Glucose: C2 – mannose C4 – galactose
CARBOHYDRATE METABOLISM The sum total of all chemical reactions needed to maintain life
Anabolism - building up Catabolism - breaking down Amphibolism- combination [ex. Krebs cycle]
energy consuming <endergonic> energy producing <exergonic>
Adenosine Triphosphate (ATP) o Energy currency of the cell o Links anabolic and catabolic reactions o Composed of ADP + P + Energy Oxidation and Reduction Oxidation + O2 -H (dehydrogenation) - e-
Reduction - O2 +H (hydrogenation) + eIn ETC,
Co-enzymes 1 mol NAD = 3 1. NAD (Nicotinamide Adenine Dinucleotide) - Nicotinamide/Niacin/Vitamin B3 ATP 1 mol FAD = 2 ATP 2. FAD (Flavin Adenosine Dinucleotide) - Riboflavin/Vitamin B2 3. Coenzyme A - precursor: Pantothenic acid/Vitamin B5 Fates of Glucose 1. ATP production 2. Amino acid and triglyceride synthesis 3. Glycogen synthesis SUBSTRATE LEVEL PHOSPHORYLATION Entails the formation of 1 unit of ATP per unit of metabolite transformed Ex. Succinyl CoA → succinate Phosphoenol pyruvate → pyruvate Does not need O2 OXIDATIVE PHOSPHORYLATION Entails the formation of 2 or 3 units of ATP per unit of metabolite transformed Uses co-enzymes: FAD and NAD Substrate + NAD+ Substrate + NADH
Summary of oxidation of 1 mole of glucose Glycolysis Intermediate step Krebs Cycle
Glucose → pyruvate Pyruvate → Acetyl CoA Acetyl CoA →CO2 + ATP
Number of units 1 2 2
Number of ATP 6-8 6 24
GLUCOSE CATABOLISM 1. 2. 3. 4.
Glycolysis Formation of Acetyl CoA; Intermediate Reaction Kreb’s Cycle Electron Transport Chain
Glycolysis/Embden-Meyerhof Pathway o o o
Aerobic (mitochondria) Anaerobic (cytoplasm) End product: 2 pyruvic acid Summary: 1 Glu 2 pyruvic acid 6-8 ATP
Intermediate Reaction: Formation of Acetyl CoA o o o
In anaerobic reactions, pyruvic acid is converted to lactic acid In aerobic reactions, pyruvic acid is converted to Acetyl CoA, which enters the Kreb’s cycle Removal of carbon dioxide: Decarboxylation
Kreb’s Cycle/Citric Acid Cycle/ Tricarboxylic Acid Cycle (mitochondria, aerobic cellular respiration)
Electron Transport Chain o o o o
O2 – final electron acceptor Complete O2 reduction H2O Partial O2 reduction superoxide anions (O2-), hydroxyl radicals (OH-) and peroxides (H2O2) Products: ATP + H2O
GLUCOSE ANABOLISM 1. Glycogenesis o Glucose Glycogen o Hormone responsible: Insulin 2. Glycogenolysis o Occurs in emergency situations o Glycogen Glucose o Hormone responsible: Epinephrine or Adrenaline o Glycogen – glucose supply for 12-14 hours o Stored in the liver, kidneys, and intestinal epithelium
Pancreatic Hormones α – Glucagon β – Insulin
3. Gluconeogenesis o Glucose is synthesized from noncarbohydrate materials (lactate, glycerol, amino acids), proteins, fats, and other sources
Pentose phosphate pathway/Phosphogluconate pathway/Hexose monophosphate shunt o
o
Occurs in the CYTOSOL o To produce ribose – 5 – PO4 for nucleotide/DNA synthesis o To produce NADPH from NADP+ for FA and steroid synthesis, maintaining reduced Glutathione inside RBCs o To interconvert pentoses and hexoses ENZYME: Glucose – 6 – PO4 Dehydrogenase o G6PD Deficiency stops PPP o production of NADPH failure to maintain glutathione in the reduced state (maintains RBC integrity) o results to hemolytic anemia upon taking oxidizing drugs (e.g. primaquine, sulfonamides, INH)
GLYCOGEN STORAGE DISEASES 0 Glycogen synthase I Von Gierke Glucose-6-phosphatase II Pompe Acid maltase/α-1,4-glucosidase III Forbes-Cori Debranching enzyme IV Andersen Branching enzyme V McArdle Muscle phosphorylase VI Hers Glycogen phosphorylase VII Tarui Muscle phosphofructokinase VIII Liver phosphorylase kinase
TESTS FOR CARBOHYDRATES Molisch’s Fehling’s
Test for General for carbohydrates Reducing sugars
Benedict’s Barfoed’s Tollen’s Picric acid Nylander’s Osazone/Kowarsky Seliwanoff’s Keller-Killiani Test Moore’s Mucic acid Test Bial’s
Reducing sugars Reducing sugars; Monosaccharides Reducing sugars (Aldehydes) Reducing sugars Reducing sugars Mannose Ketohexose (Fructose) Deoxysugars (cardiac glycosides) Reducing sugars (Glucose) Galactose Pentoses
Composition α-naphthol A – CuSO4 B – K Na tartrate NaOH + CuSO4 Cupric acetate + acetic acid Silver + Ammonia Picric acid Na K tartrate + K/NaOH + Bi Phenylhydrazine Resorcinol Acetic acid, Fe chloride, Sulfuric acid Heat with alkali Nitric acid Resorcinol + Fe
Positive result Purple/Red Brick red ppt Brick red ppt Brick red ppt Silver mirror Mahogany red Brown Yellow ppt (ozone) Red Reddish brown Caramel Insoluble ppt Blue green
LIPIDS o o
Fewer covalent bonds due to decrease in oxygen concentration Hydrophobic: they are not soluble in plasma, thus, are covered with proteins (LIPOPROTEINS)
GROUPS OF LIPIDS 1. LIPOPROTEINS – carrying lipids in the body Chylomicrons VLDL HDL/Good cholesterol - Carries cholesterol from vessels to liver where it is metabolized LDL/Bad cholesterol - Deposits cholesterol to other parts of the body 2. TRIGLYCERIDES Energy storage Excess triglycerides are deposited in adipose tissues Functions: Protection (visceral organs), Insulation, Source of energy (9 cal/g) Components: Glycerol + Fatty acids 3. PHOSPHOLIPIDS/PHOSPHOGLYCERIDES Membrane lipids Glycerol + Fatty acid + Phosphoric acid + Organic molecule/Polar head group Hydrogen : Phosphatidic acid (parent compound of all phosphoglycerides Choline : Phosphatidylcholine (aka Lecithin) ID Test for choline: Ethanolamine : Phosphatidylethanolamine (aka Cephalin) Rosenheim Test Glycerol : Phosphatidylglycerol (aka Cardiolipin) 4. SPHINGOLIPIDS/GLYCOLIPIDS/GLYCOSPHINGOLIPDS Component of cell membrane, Component of myelin sheath Skeleton: Ceramide (Sphingosine + Fatty acid) + Phosphoric acid + Organic molecule/Polar head group Monosacch : Cerebrosides – component of myelin sheath Disacch : Globoside Charged group : Gangliosides Phosphocholine/Phosphoethanolamine: Sphingomyelin 5. STEROIDS – Cyclopentanoperhydrophenanthrene (CPPP) nucleus STEROLS
A. Cholesterol – precursor of other steroids B. Bile salts Produced by liver, Stored in gallbladder Function: emulsification of fats
Animal Plant Fungi Soybean
Cholesterol Phytosterol or β-sitosterol Ergosterol Stigmasterol
C. Vitamin D – Sunshine vitamin, needed for calcium absorption - Precursors: 1. 7-dehydrocholesterol Cholecalciferol or Vit. D3 2. Ergosterol Ergocalciferol or Vit. D2 D. Sex Hormones Estrogen, Progesterone Testosterone
- woman’s secondary characteristics - man
E. Adrenocortical Hormones Vasopressin – regulates hormone & electrolyte imbalance (deficiency Diabetes insipidus)
LIPID METABOLISM
Waste products of β oxidation:
Lipase Lipids
Glycerol
+ Fatty Acids (LIPOLYSIS)
Acetyl CoA (β-oxidation pathway) GLyceraldehyde-3-phosphate
Cholecystokinin (contracts gallbladder to release bile) Cholelith (medical term for gallstones)
SATURATED FATTY ACIDS 10C Capric 12C Lauric 14C Myristic 16C Palmitic (most abundant FA) 18C Stearic 20C Arachidic UNSATURATED FATTY ACIDS 18:1 Oleic 18:2 Linoleic 18:3 Linolenic (dietary precursor of PGE) 18:4 Arachidonic (precursor of PGE) Vitamin F (essential FAs): Oleic, Linoleic, Linolenic
1. 2. 3.
Acetoacetic acid β-hydroxybutyric acid Acetone
* The three are Ketone Bodies (acidic) DKA – Diabetic ketoacidosis Manifestation: acetone breath
Rosenheim Test—used to detect the presence of choline Liebermann-Burchard Test—most sensitive, presence of cholesterol Saklowski – double bond Acrolein – glycerol
Acid value Ester value SV/Koettsdorfer Hydroxyl value Iodine value
# of mg of KOH required to Neutralize the free acids in 1g Saponify the esters on 1 g Neutralize free fatty acids and saponify esters # of KOH equivalent to OH content of 1 g subs # of mg of Iodine absorbed by 100 g substance Measures degree of unsaturation Drying >120 (linseed, fish) Semidrying 100-120 (cottonseed, sesame) Nondrying <120 (olive, almond)
Most abundant biomolecule (70% of the body)
PROTEINS C, H, O, N (S,P) Amino Acids Building blocks of proteins Amphoteric; At physiologic pH (isoelectric point, pH 7.4), exists as zwitterions Peptide bond – the bond that joins each amino acid Uses of Amino Acids Tryptophan 5-hydroxytryptamine (5-HT)/Serotonin Glycin Heme (hemoglobin) Tyrosine Catecholamine (Dopamine, NE, E) Histidine Histamine Alcohol Serine Threonine
Essential Amino Acids Valine Methionine Histidine Threonine Phenylalanine Isoleucine Leucine Lycine Arginine Tryp
Basic (R+) Histidine Arginine Lysine
Aliphatic or BCAAs (Branched Chain) Leucin Isoleucin Valine
Acidic (R-) Glutamate Aspartate
Alkyl Group Leucin Isoleucin Valine Proline Alanine
*When in urine, MSUD – Maple syrup urine disease
Amide Glutamine Aspargine
Nonpolar Glycine Alanine Valine Isoleucine Phenulalanine Tryptophan Methionine Proline
Uncharged Polar Serine Threonine Tyrosine Asparagine Cysteine Glutamine
Proline (Pro, P) – only amino acid without an amino group; It has an imino group (Imino acid) Glycine (Gly, G) – simplest amino acid (R group is Hydrogen); only amino acid that is not optically active Identification Tests Ninhydrin (General) Biuret Hopkins-Cole Bromine water Nitroprusside
Group responsible α-amino (except Pro) Peptide bond Indole
Schiff’s Xanthoproteic
Amino Aromatic
Millon-Nase Sakaguchi Pauly-Diazo Basic Lead Test
Phenol
Sulfhydryl
Example
Tryptophan Tryptophan Cysteine (thiol) Met (thioether) Lysine Phen (benzyl) Tyr (phenol) Tryp (indole) Tyrosine Arginine Histidine, Tyrosine Cysteine
Positive Result Blue/Lavender Violet Violet ring Violet layer Purple Pink-violet Lemon yellow
Red Intense red Red Black ppt
Levels of Structural Organization of Proteins Level Primary Secondary Tertiary
Determines Sequence of AA Twisting and folding Function 3D structure
Bonds
Quaternary
Specificity Arrangement of polypeptide chains
Peptide H-bond Disulfide H-bond, Ionic Hydrophobic interaction
Phe-Gly-Try-Tyr-Val-Gly N terminal – Phenylalanine C terminal - Glycine
Example α helix, β pleated sheet Fibrous Globular
CLASSIFICATION OF PROTEINS A. According to Composition SIMPLE PROTEINS
H2O
Salt sol’n
Δ
Albumins
✓
✓
✓
Globulins
✖
✓
✓
Glutelins
✖
✖
Dil. acid
✓
Dil. base
Other
NH3
EXAMPLES Ovalbumin - egg white Lactoalbumin - milk Serum albumin - blood Ovoglobulin - egg white Serum globulin - blood Lactoglobulin - milk Glutenin (wheat)
✓ 80% alcohol
Prolamines Albuminoids Histones
✓
Protamines
✓
CONJUGATED PROTEIN nonprotein substances + AA Phosphoproteins Nucleoproteins Glycoproteins Chromoproteins Lipoproteins Metalloproteins
PRIMARY DERIVED PROTEIN Denatured Proteins Proteans Metaproteins Coagulated Proteins
✖ ✓
✓
Only by boiling in strong acids basic in reaction strongly basic in reaction
PROSTHETHIC GROUP Phosphoric acid Nucleic acid Carbohydrate group Colred prostethic group Lipids metals
EXAMPLES Casein (milk), Ovovitellin (egg yolk) Nuclein (cell nuclei) Mucins (Vitreous humor and saliva) Hemoglobin (blood), Flavoproteins Fatty acid, Sterol, Lecithin Enzymes (tyrosinase, arginase, XO)
CHARACTERISTICS
EXAMPLES
Acted upon by H2O/enzymes/acid Acted upon by acid or alkali Acted upon by alcohol or heat
SECONDARY DERIVED PROTEIN formed from progressive hydrolysis of protein Proteoses Peptones Peptides
Zein (corn) Gliadin (wheat) Keratin (hair and horny tissue) Elastin (Tendons and arteries) Collagen (Skin and tendons) Thymus histone Hemoglobin Salmine - salmon Sturine - sperms of fish Scombrine - mackerel
Fibrin, Myosan Acid or alkali albuminates Coagulated albumin, Cooked meat
CHARACTERISTICS Highest MW group Intermediate MW Lowest MW group
B. According to Conformation a. FIBROUS Polypeptide chain arranged in tightly parallel fibers and sheets Make up the structural framework of the body 1. Collagen 2. Elastin 3. Keratin b. GLOBULAR Polypeptide chains are arranged in compact, spherical forms; insoluble in water 1. Antibodies 2. Hormones 3. Albumin
C. According to Biological Roles a. STRUCTURAL PROTEINS 1. Collagen - skin and cartilage 2. Elastin - vessels, dermis, tendon 3. Keratin - hair and nails 4. Glycoproteins - cell membrane b. CONTRACTILE OR MOTILE PROTEINS 1. Actin - thin & moving filament 2. Myosin - thick & stationary c. NUTRIENT OR STORAGE PROTEINS 1. Ovalbumin - egg white 2. Casein - milk d. HORMONES Chemical messengers 1. Insulin 2. Growth hormone/Somatropin e. PROTECTIVE PROTEINS 1. Immunoglobulins/Antibodies/Serum globulin o IgA - secretions o IgG - smallest o IgD - no function yet o IgE - allergy o IgM - largest ; first Ig produced during infection f.
STORAGE AND TRANSPORT 1. Myoglobin/Hgb 2. Transferrin 3. Ferritin
- oxygen carriers - transport form of Fe - storage form of Fe
ENZYMES Common properties: o Colloids that are soluble in water o Work best at temperatures between 35-40°C (optimal: 37°C) o Activity is dependent on pH of the medium o Highly selective (follows the principle of Lock and Key) Co-enzymes Zymogens or Proenzymes Apoenzymes Cofactor Holoenzyme
– vitamin cofactors – inactive form of an enzyme – protein part of an enzyme – nonprotein part of an enzyme – catalytically active enzyme (P+NP) PROTEIN Apoenzyme
Oxidoreductases
Transferases Hydrolases
+
NONPROTEIN Cofactor
• Oxidation-reduction metabolism • Ex. Dehydrogenases, oxidases, peroxidases
• Transfer of groups, such as phosphate & amino • Ex. kinases • Hydrolyze substrates • Proteolytic enzymes, amylases, esterases
Lyases
•Removal of functional groups by means other than hydrolysis •Ex. Decarboxylases, deaminases
Ligases
•Catalyze the coupling of 2 molecules •Ex. DNA ligase
Isomerases
•Catalyze various isomerizations, such as the change from D- to L- form
Carbohydrates o Amylase and Diastase (Ptyalin) o Amylopsin o Invertase o Zymase o Emulsin o Myrosin
– found in salivary glands – pancreas – converts CHO to OH and CO2 – breaks down cyanogenic glycosides – breaks down isothiocyanate glycosides
Esterases o Lipase – breaks down lipids into glycerol + fatty acids (Lipolysis) o Urease – Urea (waste product of breakdown of proteins) ammonia
Uric acid – waste product of breakdown of PURINES
Proeolytic Enzymes Pepsin (stomach) Proteins
Trypsin (intestine) Proteases & Peptones
Polypeptides & AA
HCl
Others
Found in
Use
Rennin
stomach of young animals
Curdles the soluble casein in milk
Pepsin
stomach of Sus scrofa
Assist in gastric digestion
Pancreatin (amylase, lipase, protease)
pancreas of Sus scrofa or Bos Taurus
Digestive aids
Papain
latex of Carica papaya
Bromelains
juice of Ananas comosus
Streptokinase
group C β-hemolytic streptococci
Embolism and thrombosis
Urokinase
urine or from kidney cells
Embolism and thrombosis
Sutilains
Bacillus subtilis
Wound debribement
Collagenase
Clostridium histolytica
Topically to debride dermal ulcers and burns
L-asparaginase
E. coli
Antitumor
Relieve symptoms of episiotomy, Cleaning solutions of soft contact lenses, Beef tenderizer Reduce inflammation and edema Accelerate tissue repair after episiotomy
NUCLEIC ACIDS AND PROTEIN SYNTHESIS Nucleic Acids Made up of chains of nucleotides Nucleotides consist of: 1. Nitrogen-containing heterocyclic base 2. Phosphate 3. Pentose sugar Two types of nucleic acids in cells 1. Deoxyribonucleic acid (DNA) 2. Ribonucleic acid (RNA)
Glycosidic bond – links sugar and base Phosphodiester bond – links sugar and phosphate
DNA vs RNA Sugar Purine Bases Pyrimidine Bases
DNA 2-deoxyribose Double stranded Guanine, Adenine Cytosine, Thymine
RNA Ribose Single stranded Guanine, Adenine Cytosine, Uracil
2 Types of Nitrogen Bases 1. Purine (2 rings): Guanine, Adenine 2. Pyrimidine (1 ring) a. Cytosine b. Thymine- only found in DNA c. Uracil - only found in RNA
Nucleoside vs Nucleotide Nucleoside Base (N) Sugar
Nucleotide Base (N) Sugar Phosphate
Nucleosides Adenosine Guanidine Cytidine Uridine Thymidine
Adenine Guanine Cytosine Uracil Tymine DNA
Nucleotides cAMP * cGMP *
* secondary messengers
Double helix – Watson and Crick Coiled strands containing the genetic code
Structural Organization A. Primary - unique sequence of nucleotide - base or nucleotide sequence B. Secondary - DNA double helix - H bonds Properties: 1. Complementarity Pur Pyr A
T
2 H bonds
C
G
3 H bonds
1. Helicases unwind the DNA double helix. 2. Primase creates a temporary RNA primer. 3. DNA polymerase at the replication fork synthesizes DNA in a 5’→ 3’ direction. ≡ Leading strand (continuous) ≡ Lagging strand (discontinuous) 4. DNA polymerase then removes the RNA primer and fills the gaps between the Okazaki fragments (short stretches of discontinuous DNA) 5. DNA ligase then joins DNA fragments of the lagging strand, creating a single DNA molecule. 6. Further modified by topoisomerase
2. Antiparallelism The structure should be arranged in a 3’ 5’ fashion C1 – base C5 – phosphate C. Tertiary
- supercoiling chromosomes - DNA gyrase/topoisomerase II facilitates supercoiling
Information Transmission Information stored in DNA is transferred to RNA and then expressed in the structure of proteins Two steps in process: Transcription, Translation
Types of RNA o mRNA - messenger; “template” for transcription o tRNA - transfer; carrying amino acids to sites of protein synthesis o rRNA - ribosomal RNA
Translation (Protein Synthesis) Information in mRNA translated into primary sequence of a protein in 4 steps: o Activation of tRNA o Initiation - small ribosomal subunit attaches mRNA at the initiation codon site and the first tRNA attaches o Elongation - Transfer RNA (tRNA) translates the mRNA into the amino acid sequence o Termination - Elongation continues until a stop codon is encountered Start codon: AUG (methionine) Stop codons: UAA, UAG, UGA
MUTATION A change in shape, structure, and nucleotide sequence Point Mutation Transitional Mutation Transversional Mutation Results of Point Mutation Silent Mutation - Codon containing the changed base may code for the same amino acid - Example: UCA (serine) UCU (serine)
Missense Mutation - Codon containing the changed base codes for a different amino acids - Causes disease - Example: UCA (serine) CCA (proline)
Nonsense Mutation - Codon containing the changed base may become a stop codon - Example: UCA (serine) UAA (stop codon)
Frameshift Mutation Insertion Mutation Deletion Mutation
VITAMINS AND VITAMIN-CONTAINING DRUGS Vitamins o Organic substances, not synthesized within the body, that are essential in small amounts for the maintenance of normal metabolic functions o Do not furnish energy and are not utilized as building units for cellular structure o Term was derived in 1911 – vital amine o Used as special dietary supplements or as drugs Vit. B2, B3, B5 – coenzymes Vit. B12, B9 – biosynthetic transfer of 1-C units Vit. C – biosynthesis of hydroxyproline Vit. B1, B6 – metabolism of carbohydrates and amino acids Biotin – metabolic carboxylation Vit. D, E – influence membrane transport
FAT-SOLUBLE VITAMINS (A, D, E and K)
Absorption from the intestinal tract is associated with that of lipids and a deficiency state may be caused by conditions that impair fat absorption
Vitamin A (β-ionine, Retinol) - Most toxic vitamin - Most stable vitamin
Function Vision, growth, tissue differentiation
Vitamin D (Sunshine vitamin)
Ca and PO4 absorption
Vitamin E (α-tocopherol) Test: Further-Meyer Synergistic with Se Vitamin K (2-methyl-1,4naphthoquinone)
Antioxidant
Prothrombin formation
Tretinoin or all-trans retinoic acid (Retin-A) Highly teratogenic Treat acne vulgaris Isotretinoin or 13-cis retinoic acid (Accutane) For cystic acne CI: Pregnancy B-carotene (Solatene) Precursor (converted in small intestine) Ergocalciferol/D2 - from ergosterol Cholecalciferol/D3 - 7-dehydrocholesterol Calcifediol and Calcitriol - hypocalcemia Dihydrotachysterol - tetany, hypoPTH
Vitamin K1 (phytonadione) Vitamin K2 (prenylmenaquinone-7) Vitamin K3 (menadione, menaquinone) – most active form Vitamin K4 (menadiol)
Source Fish liver oils
Deficiency Nyctalopia Xeropthalmia Hyperkeratosis
Fish liver oils
Rickets Osteomalacia
green veggies, whole grains, yolk, meat
Neurologic dysfunctions (rare)
Leafy veggies Dairy
Hemorrhage and Capillary fragility
WATER SOLUBLE VITAMINS Function B1
Thiamine
Decarboxylation (CHO, AA)
B2
Riboflavin
Redox coenzyme, FAD
B3
Niacin/Nicotinic acid/Niacinamide/ Nicotinamide
Redox coenzyme, NAD
B5
Pantothenic acid “chick antidermatitis factor”
Acetyl CoA Secretion of hormones (cortisone)
Pyridoxine
Transamination, Decarboxylation (CHO, AA), RBC metabolism
B6
Pyridoxol – plants Pyridoxal and pyridoxamine – animals
B9
Folic acid Pteroylglutamic acid
B12
Cobalamin Cyanocobalamin – most active Hydroxocobalamin – for CN toxicity associated with Na nitroprusside
B17
Laetrile
B15
Pangamic Acid
Pyridoxine antagonists: chloramphenicol, cycloserine, hydralazine, isoniazid and oral contraceptives Folate FH2 Tetrahydrofolic acid (liver & plasma)
Deficiency Beriberi Wernicke-Korsakoff Stomatitis Chelitis Glossitis SE: yellow urine Pellagra Dementia Dermatitis Diarrhea Paresthesias of the extremities or “burning foot” syndrome Peripheral neuropathy RBC fragility Hypochromatic microcytic anemia Megaloblastic anemia Macrocytic anemia Pernicious anemia
RBC synthesis Metabolism of Folic Acid
Rapidly dividing cells of the hematopoietic system and irreversible neurologic damage
Impaired fat and CHO metabolism, Dermatitis H
C
D-biotin
Cevitamic acid
Carboxylation (gluconeogenesis and FA synthesis)
Hydroxylation of pro and lysine (collagen synthesis) Anti-oxidant Enhances Fe absorption
* Biotin deficiency is usually caused by avidin Scurvy (impaired wound healing, loss of dental cement, SQ hemorrahge)
VITAMIN-RELATED FACTORS Para-aminobenzoic Acid (PABA) Precursor of folic acid Added as an accessory food factor Used for rheumatic fever and other conditions benefiting from salicylate therapy; UV sunscreen in topical preparations Interferes with the antibacterial action of sulfonamides Choline (B-hydroxyethyltrimethylammonium hydroxide) Occur in egg yolk, animal organs, fish, milk, cereal grains, fruits and root vegetables Essential nutrient in certain higher animals USE: lipotropic agent in conditions such as liver cirrhosis, Huntington’s chorea, presenile dementia and tardive dyskinesia Inositol (meso-inositol, myoinositol or cis-1,2,3,5-trans-4,6-cyclohexanehexol) Dietary sources: legumes, cereal grains, nuts and animal organs Implicated in membrane transport of amino acids and K and Na ions Large doses may cause moderate diarrhea MULTIVITAMIN THERAPY Inadequate vitamin intake can result not only from a poor diet but also from alcoholism, increased needs during pregnancy and lactation, prolonged broad-spectrum antibiotic therapy and the course of parenteral nutrition.
Filipino/Tagalog Name
English Name
Scientific Name
Singkamas
Mexican turnip
Pachyrhizus erosus
Talong
Eggplant
Solanum melongena
Sigarilyas
Winged beans
Psophocarpus tetragonolobus
Mani
Peanuts
Arachis hypogaea
Sitaw
String beans
Phaseolus vulgaris
Bataw
Hyacinth bean
Lablab purpureus
Patani
Lima beans
Phaseolus lunatus
Kundol
Winter melon
Benincasa hispida
Patola
Sponge/vegetable gourd
Cucunis acutangulus
Upo
Bottle gourd
Lagenaria siceraria
Kalabasa
Squash
Cucurbita maxima
Labanos
White radish
Raphanus sativus
Mustasa
Mustard
Brassica integrifolia
Sibuyas
Onion
Allium cepa
Kamatis
Tomato
Solanum lycopersicum
Bawang
Garlic
Allium sativum
Luya
Ginger
Zingiber officinale
Linga
Sesame
Sesamum indicum
Halamang Gamot
Scientific Name
Lagundi
Vitex negundo
Yerba Buena
Clinopodium douglasii
Sambong
Blumea balsamifera
Tsaang-gubat
Ehretia microphylla Lam.
Niyog-niyogan
Quisqualis indica
Bayabas
Psidium guajava
Ulasimang bato
Peperonia pellucida
Akapulko
Cassia alata
Bawang
Allium sativum
Ampalaya
Momordica charantia
Common Name
Scientific Name
Common Name
Scientific Name
Santan
Ixora chinensis
Avocado
Persea americana
Duranta
Duranta repens
Grapes
Vitis vinifera
Gabi-gabi
Monochoria hastata
Pears
Pyrus communis
Talisay
Terminalia catappa
Olive
Olea europaea
Pechay
Brassica pekinensis
Peanuts
Arachis hypogaea
Achuete
Bixa orellana
Strawberry
Fragaria ananassa
Anis
Foeniculum vulgare
Pineapple
Ananas comosus
Balanoy
Ocimum basilicum
Apple
Pyrus mallus
Balatong (soy)
Glycine soja
Rice
Oryza sativa
Balimbing
Averrhoa carambola
Mango
Mangifera indica
Chico
Achras zapota
Coconut
Cocos nucifera
Dalandan
Citrus sinensis
Durian
Durio zibethinus
Dalanghita
Citrus nobilis
Carrots
Daucus carota
Damong maria
Artemisia vulgaris
Banana
Musa acuminata
Duhat
Syzygium cumini
Gumamela
Hibiscus rosa-sinensis
Gugo
Entada phaseoloides
Daisy
Bellis perennis
Ikmo
Piper betle
White orchid
Dendrobium afinne
Ipil-ipil
Leucaena leucocephala
Corn
Zea mays
Kalamansi
Citrus microcarpa
Bougainvillea
Bougainvillea glabra
Kamias
Averrhoa bilimbi
Jackfruit
Artocarpus heterophyllus
Kasoy
Anacardium occidentale
Mangosteen
Garcinia mangostana
Kintsay
Apium graveolens
Date
Phoenix dactylifera
Lansones
Lansium domesticum
Atis
Anona squamosa
Makabuhay
Tinospora crispa
Papaya
Carica papaya
Makahiya
Mimosa pudica
Potato
Solanum tuberosum
Malungggay
Moringa oleifera
Orange
Citrus aurantium
Mansanilya
Chrysanthemum indicum
Codiaeum variegatum
Moras
Vetiveria zizanioides
Pakwan
Citrus vulgaris
Patola
Lufa acutangula
Sampalok
Tamarindus indica
Suha
Citrus grandis
San Francisco Rosy periwinkle/chichirika Turmeric Jimson weed/talumpunay Picapica
Tanglad
Cymbopogon citratus Grammatophyllum scriptum
Pacific yew
Taxus brevifolia
Tawa-tawa
Catharanthus roseus Curcuma longa Datura spp Mucana pruriens
CARBOHYDRATES AND RELATED COMPOUNDS MONOSACCHARIDES 1 Dextrose 2 Fructose 3 Xylose
(blood sugar, d-glucose, alpha-d (+) – glucopyranose) (d-fructose, levulose. B-D (-) fructopyranose, fruit sugar) (d-xylose, wood sugar)
DISACCHARIDES 4 Sucrose 5 Maltose 6 Lactose
(saccharum, cane sugar, beet sugar, table sugar) (malt sugar) (cows milk, milk sugar)
POLYSACCHARIDES HOMOGLYCANS 1 Starch 2 Dextran 3 Cellulose HETEROGLYCANS 1 Tragacanth 2 Acacia 3 Ghatti Gum 4 Karaya Gum 5 Plantago Seed 6 Cydonium 7 Guar Gum 8 Locust Bean Gum 9 Agar 10 Sodium Alginate 11 Carrageenan 12 Danish Agar 13 Xanthan Gum 14 Pectin
(gum Arabic) (Indian Gum) (Sterculia Gum)
(red Algae) (brown Seaweeds) (red Algae Or Seaweeds) (red Algae) (microbial Gum)
DRUGS CONTAINING COMPOUNDS METABOLICALLY RELATED TO SUGARS 1 Citric Acid ( 2-hydroxy 1,2,3, propane trioic acid) 2 Lactic Acid ( alpha-hydroxy propionic acid) 3 Tartaric Acid ( 1,2,3, dihydroxy butane dioic acid ) 4 Mannitol (D-mannitol) 5 Sorbitol (D-glucitol) 6 Alcohol or Ethanol
GLYCOSIDES CARDIAC 1 Foxglove 2 Grecian Foxglove 3 Convallaria 4 Apocynum 5 Adonis 6 Cactus Grandiflorus 7 Black Hellebore 8 Strophanthus 9 Squill ANTHRAQUINONE 1 Cascara Sagrada 2 Frangula 3 Aloe 4 Rhubarb 5 Senna 6 Chrysarobin SAPONIN 1 Glycyrrhiza 2 Ginseng 3 Dioscorea
(Digitalis purpurea) (Digitalis lanata) (Lily-of-the-Valley) (black Indian hemp, dog bane or Canadian hemp) (pheasant’s eye) (night blooming cereus) (Christmas rose) (Squill bulb)
(rhamnus purshiana) (Frangula or buckthorn bark) (Rheum, or Chinese rhubarb) (Senna or senna leaves)
(licorice root) (Mexican Yam)
CYANOPHORE OR CYANOGENIC (bound poisons) 1 Bitter Almonds 2 Wild Cherry (Prunus Virginiana, Wild Black Cherry Tree) 3 Apricot Pits GLUCOSINOLATES OR ISOTHIOCYANATES 1 Mustard (black mustard, sinapis nigra or brown mustard) 2 White Mustard (white mustard or sinapis alba) LACTONE GLYCOSIDES 1 Coumarin 2 Cantharides 3 Psoralens
(dicumarol or Bishydroxycoumarin) (Spanish flies, Russian flies, blistering flies)
ALCOHOL: ALDEHYDE: PHENOL:
(vanilla or vanilla bean)
Salicin Vanilla Uva Ursi
LIPIDS FIXED OILS SATURATED 1 Coconut Oil 2 Palm Oil MONOUNSATURATED 1 Castor Oil 2 Olive Oil 3 Peanut Oil 4 Rapeseed Oil POLYUNSATURATED 1 Soybean Oil 2 Cottonseed Oil 3 Sesame Oil 4 Almond Oil 5 Persic Oil 6 Corn Oil 7 Safflower Oil 8 Sunflower Oil 9 Linseed Oil 10 Cod Liver Oil FATS AND RELATED COMPUNDS 1 Theobroma Oil 2 Lanolin FATTY ACIDS 1 Stearic Acid 2 Oleic Acid 3 Undecylenic Acid 4 Sodium Morrhuate WAXES 1 Spermaceti 2 Jojoba Oil 3 Beeswax 4 Carnauba Wax
(sweet Oil) (arachis Oil) (canola Oil)
(teel Oil, Benne Oil) (sweet And Bitter Almond) (apricot Kernel Oil, Peach Kernel Oil) (Safflower Seed Oil)
VOLATILE OILS HYDROCARBON: OXIDE:
Turpentine Oil Cineole/Eucalyptol
ALCOHOL 1 Peppermint Oil 2 Cardamom Oil 3 Coriander Oil 4 Rose Oil 5 Orange Flower Oil 6 Juniper Oil 7 Pine Oil ALDEHYDE 1 Cinnamon Oil 2 Lemon Peel 3 Orange Oil 4 Citronella Oil 5 Hamamelis Water KETONE 1 Camphor 2 Spearmint 3 Spearmint Oil 4 Caraway Oil 5 Buchu 6 Wormwood Oil 7 Cedar Leaf Oil PHENOL 1 Thymol 2 Clove Oil 3 Myrcia Oil 4 Creosote 5 Juniper Tar PHENOLIC ETHER 1 Nutmeg Oil 2 Fennel Oil 3 Anise Oil ESTER 1 2 3 4
Gaultheria Oil Lavender Oil Pine Needle Oil Mustard Oil
(Spirits Of Turpentine) (cajuputol)
(otto Of Rose) (neroli Oil)
(cassia Oil)
(absinthe Oil)
(bay Oil) (beachwood Creosote) (cade Oil)
(myristica Oil)
(wintergreen Oil, Betula Oil, Sweet Birch Oil) (dwarf Pine Needle Oil) (allyl Isothiocyanate)
RESIN AND RESIN COMBINATIONS RESINS 1 Rosin 2 Podophyllum 3 Eriodictyon 4 Jalap 5 Mastic 6 Kava 7 Cannabis OLEORESINS 1 Turpentine 2 Capsicum 3 Ginger 4 White Pine 5 Copaiba
OLEO-GUM-RESIN: BALSAMS 1 Storax 2 Peruvian Balsam 3 Tolu Balsam 4 Benzoin
(colophony) (mayapple, Mandrake) (yerba Santa) (jalap Root) (mastiche, Mastich) (kava-kava) (Indian Hemp, Marihuana)
(cayenne Pepper)
Myrrh
(liquid Storax, Styrax)
ALKALOIDS PYRIDINE-PIPERIDINE 1 Areca 2 Lobelia 3 Nicotine
(Areca Nut, Betel Nut) (Indian Tobacco)
TROPANE/SOLANACEOUS 1 Belladona 2 Stramonium 3 Cocaine
(Deadly Nightshade Leaf) (Jimson Weed, Jamestown Weed) (Coca)
QUINOLINE: Cinchona IMIDAZOLE: Pilocarpine
(Peruvian Bark) (pilocarpus , Jaborandi)
ISOQUINOLINE 1 Ipecac 2 Hydrastis 3 Sanguinaria 4 Opium
(Golden Seal) (Blood Root) (opium Or Gum Opium)
INDOLE 1 Rauwolfia Serpentina 2 Catharanthus (Vinca) 3 Nux Vomica 4 Physostigma (Physostigma, Calabar Bean, Ordeal Bean) 5 Ergot (rye Ergot, Secale Cornutum) STEROIDAL 1 Veratum Viride 2 White Hellebore
(American Or Green Hellebore) (European Hellebore)
ALKALOIDAL AMINES 1 Ephedrine 2 Colchicine 3 Khat 4 Peyote
(Ephedra, Mahuang) (Colchium Seed) (abyssinian Tea) (mescal Buttons)
PURINE BASES 1 Caffeine 2 Theophylline 3 Theobromine
(1,3,7 Trimethylxanthine) (Thea , Tea , 1,3 Dimethylxanthine) (3,7 Dimethyl Xanthine)