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PHARMACOGNOSY

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PHARMACOGNOSY

Applied science -> biological, biochemical and economic features of drugs of biological origin and their constituents

Medicinal products in their crude or unprepared form

HISTORY OF PHARMACOGNOSY

Bablylonians

Laws of Hammurabi (172 BC); clay models of human body; medicinal effects of 250 plants; mages and physician; wheat and barley

Ayurveta (2500 BC)

Traditional medicine; “Science of life”; Mother of all healing arts

Charaka text on internal medicine

Sushruta 184 chapters; 1120 illness

Egyptians (Ebers papyrus 1150 BC)

Embalming; George Ebers; priest and doctors; human anatomy and use of plants

Greeks

Dioscorides wrote De Materia Medica” or The Medicinal material; aloe, belladonna, colchicum, ergot, opium; 600 plants

Claudius Galen described methods and processes of preparing formulas containing plant and animal drug; FATHER OF PHARMACEUTICAL COMPOUNDING

Germans

CA Seydler (1815) – coined the term, “pharmacognosy” from “pharmakon” and “gnosisin Analecta Pharmacognistica

JA Schidt (1811) – used the word, “pharmacognosy”; Lehrbuck de Materia Medica; described study of medicinal plants and their properties

Fluckiger simultaneous application of various scientific

disciplines with the object of acquiring drugs from every point of view

Pellitier and Caventou Quinine

Freidrich Serturner - Morphine

CRUDE DRUGS

vegetable or animal drugs consists of natural substances that had undergone only the processes of collection and drying; plant exudates

Natural Substances formed in nature; whole plants or parts; animals or organs; no molecular modifications had been made Derivatives of Extractives chief principle or constituents of crude drugs that are separated and used in a specific manner

Menstruum solvent; liquid/liquid mixture used to extract active principle

Marc undissolved portion of the drug that remarks after extraction process is completed

Methods of Extraction

Infusion hot water (ex. tea); short contact of action

Maceration soaked in solvent for long period of time

Percolation passage through percolate (ex. Simple Syrup USP)

Digestion - <35-40 o C

Decoction boiling water

Liquid-Liquid Extraction Partitioning Distillation

Indigenous Plants plants growing in their native countries (ex. Rinorea niccolifera metal eating plant; more on nickel) Naturalized Plants plants that grow in foreign land other than their native homes

Preparation of Crude Drugs 1. Collection ensuring the true natural source of the drug:

improper collection, collection time, highest content Harvesting specific or proper season; manual labor vs mechanical devices 2. Drying remove moisture to prevent bacterial and fungal growth with enzymatic degradation; fixed constituents, facilitates grinding and milling; converts plants to convenient form 3. Curing special drying process that enhances properties of plants’ active ingredients 4. Garbling final step in preparation of crude drugs; removal of extraneous matter *Last Packaging, Storage, Preservation protection and marketability; maintain high degree of quality of drug

Evaluation of Crude Drugs determine quality and purity; qualitative (intrinsic value of drug; type of medicinal prinnciples) and quantitative (amount)

Organoleptic Evaluation organs of senses; evaluates macroscopic appearance of drug

Microscopic evaluate in a cellular level

Pharmacologic Evaluation o Bioassays assays using living animals or excised organs to evaluate effects of drugs

Chemical Evaluation assay of active constituents using chemicals (titration); best determination of official potency

CLASSIFICATION OF DRUGS

1. Morphology forms; plant part used; convenient but no chemical correlation 2. Taxonomic (Lireus) evolutionary development; no correlation on chemical and biological activity Phylogeny natural relationship that occurs among plants and animals 3. Pharmacologic based on therapeutic effect on body 4. Chemical preferred method of classification based-active constituents that are present; phytochemical studies but ambiguous at times

Active Constituents considered secondary metabolites; through drug biosynthesis or biogenesis

BIOGENESIS

Ontogemy or Stage of Development Ex. Cannabis sativa (cannabidiol plant is young; cannabinol mature plant)

Heredity same but not the same

Environment

I.

CARBOHYDRATES

Polyhydric aldehyde or ketone alcohols that contain C, H, and

O

H and O has same ratio as that of water, thus named CARBO +

HYDRATES

First product of synthesis [CH 2 O] n

Xylem H 2 O

Phloem nutrients food (source; storage; structure)

A. CLASSIFICATION OF CARBOHYDRATES

I. MONOSACCHARIDES simplest carbohydrate unit; cannot be hydrolyzed; identification test: Benedicts and Barfoed’s = brick red ppt.; *neuramonic aka sialic PENTOSES

Xylose wood sugar”; obtained from boiling corn cobs, straw; diagnostic aid for intestinal malabsorption; absorbed but not metabolized

o Xylan -> Xylose (aldehyde) -> xylulose (ketoses)

HEXOSES most important monosaccharide

Glucose aldohexose; aldehyde group is present in C1; reducing sugar as determined by Benedict’s Test; occurs as linear and cylic;

o

β-D-Glucose most abundant

o

D-Glucose aka Dextrose, Blood Sugar, Grape Sugar, Physiologic Sugar

o

Uses:

Parenteral rigorously purified; as nutrient

Pharmaceutic necessity less rigorous purification; Liquid Glucose syrupy liquid; incomplete acid hydrolysis of starch; almost colorless and taste sweet; Dextrose excipient crystalline sweetening agent (Oral Glucose Tolerance Test 75g)

Fructose ketohexose = (+)Seliwanoff’s Test: pink/red; ketone group is present in C2; reducing sugar; fruit sugar; sweet fruits and honey; aka Levulose (sweetest monosaccharide); obtained from inversion of aq. sucrose solution; honey (mostly sucrose)

o

High Fructose Sweeteners isomerization of glucose isomers from Streptomyces sp.

o

Uses:

Food for diabetic

Ingredient in infant feeding formula

Ingredient in Fructose injection nutruient

Galactose aldohexose; “Brain Sugar”; C4 epimer of glucose (C2 mannose); milk:lactose::neuronal fibers:galactosides; Gaucher’s Disease; (+) Mucic acid and Phenylhydralazine = crystal formation (osazone crystals)

II. DISACCHARIDES composed of two monosaccharide units; formed via dehydration synthesis; glycosidic bond

Sucrose “table sugar”; obtained from:

o

Saccharum officianarum (sugar cane) (+) lime = decreased albumin; use SO 2 clear = clarification

o

Beta vulgaris (sugar beets) – cossettes (“cut limps livers” – chop finely)

o

Acer saccharum (sugar maple)

-

non-reducing sugar: (-)Benedict’s Test

-

glucose + fructose, α-1,2 bond

-

uses: demulcent, sweetening agent to mask taste, coating agent, preservative (85%), production of syrups, retards oxidations

- Molasses residual dark colored syrup after complete crystallization of sucrose; only disaccharide in free state; food and ethanol industry

Maltose malt sugar; produced-germination of barley; glucose + glucose, α-1,4 bond; major degradation product of starch; reducing sugar (beer, ovaltine, cereal drinks); glu + glu + glu = maltotriose (oligosaccharide 3-10C)

Lactose milk sugar (cow’s milk); glucose + galactose, β-1,4 bond; reducing sugar; milk products:

1. Whole milk (sit)-> butter 2. Butter milk (churn)-> cream 3. Skimmed milk -> whey (rennin young calf) coagulum (tx)-> cheese

* Kamyss fermented spoiled milk

* Condensed Milk partial condense autoclave, evapo

Lactulose fructose + galactose, β-1,4 bond; alkaline rearrangement of lactose; converted by lactose to lactic and acetic acid, which causes irritation of the intestines and subsequent cathartics ideally used with MI and stroke

PRODUCTS OF OXIDATIVE METABOLISM

Cherry Juice ripe fruit of Prunus cerasus (Rosaceae); contains pectin and 1% malic acid; cherry syrup

Plant Acids uses: acidulants in effervescent formulations; component of buffer systems

o

Citric Acid Scheele lemon juice (1784); citric Tricarboxylic acid (TCA) (Deniges Test)-> tartaric (by product, dicarboxylic) = wine

o

Lactic Acid acidulant infant feeding formula, feminine wash (0.2% chlohexidine vaginal; 0.6% - mouth) (INSERT)

Alcohol/Ethanol 95% ethanol by volume 15.56 o C; product of fermentation; undergo process of distillation to concentration the alcohol content to 40-55%; low conc. CNS stimulant; high conc. CNS depressant

o

Brandy - wine

o

Whiskey malted grain

o

Rhum - molasses

o

Diluted Alcohol 48.4-49.5% ethanol at 15.56% o C

PRODUCTS OF REDUCTIVE METABOLISM

Mannitol from manna, dried exudate of Franxinus ornus; osmotic diuretic and osmotic laxative, GFR; used in people with neurological trauma

Sorbitol from berries of mountain ash, Sorbus aucuparia; aka D-glucitol; tastes ½ sweet as sugar; used in manufacture of toothpaste and chewing gum xylitol as alternative

III. POLYSACCHARIDES

Homoglycans

polysaccharides

that

yield

one

type

of

monosaccharide unit upon hydrolysis

o

Starch temporary storage form of photosynthetic products from:

Zea mays corn

 

Triticum aestivum wheat

Solanum tuberosum potato

Oryza sativa rice

Maranta arundinacea arrowroot

Constituents:

 
 

Bases of

Amylose

Amylopectin

Differences

Structure

Linear/Helical

Branched (every 25-30 mins) 1000 or more α-1,4 and α-1,6

250-300 units

α-1,4

Solubility

Insoluble

Soluble

in water

Iodine test

Deep/Dark blue

Blue violet/purple

Enzymes that breaks down starches:

 

1. Alpha amylase present in pancreatic juice and saliva; *metabolism/breakdown of carbohydrates starts in mouth 2. Beta amylase hydrolyses starch to nearly pure maltose Uses: tablet filler, binder and disintegrant; antidote for iodine poisoning Starch Preparations:

1. Pregelatinized starch chemically or mechanically processed to rupture all or part of granules; tablet binder 2. Sodium starch glycollate disintegrating agent 3. Hetastarch - >90-99% amylopectin; plasma expander; hydroxyethylstarch; Voluben® 4. Glutens tacky proteins that impedes flow of starch

o

Glycogen storage polysaccharide in animals; more branched than starch (every 10); red color with iodine

o

Inulin polyfructan of fructofuranose; Chicorium intybus (Asteraceae) chicory root; improve digestion; Uses:

ingredient in culture media; evaluation of renal function

o

Dextran glucosan; Leuconostoc mesenteroides; plasma

expander

 

o

Cellulose structural polysaccharide in plants (from the hair of seeds of Gossypium hirsutum)

Purified/Absorbent Cotton surgical dressing

Soluble Guncotton/Pyroxylin formed by action of nitric and sulfuric acid on cotton; Other ingredients: castor oil (flexibility); camphor (water-proof); Use: topical protectant

Other Cellulose Derivatives cellulose acetatephthalate (CAP) coating agent; methylcellulose and ethycellulose artificial tears

o Chitin structural polysaccharides in animals; exoskeleton:

mollusks and arthropods; homoglycan of N- acetylglucosamine

Chitosan deacetylation of chitin; water purification

Glucosamine acid deacetylation and hydrolysis of chitin

Heteroglycans polysaccharides that yield more than one types of monosaccharide units upon hydrolysis

B. 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

Pb acetate and alcohol

   

LINEAR

BRANCHED

Solubility

Less

More

Stability

Less

More

Use

Viscosity enhancers

Gelating agents

 

GUMS

MUCILAGES

Production

 

Pathologic (injury)

Physiologic

 

(natural)

Solubility in water

Readily soluble

Slimy mass

 

PLANT EXUDATES

 

BOTANICAL SOURCE

Acacia - Gum Arabic -> arabin -> K, Ca, Mg, Arabic acid; mucilage; emulsifier; suspending agent (33-35%); 12% H 2 O content; <60% alcohol

 

Acacia Senegal

Tragacanth Types: vermiform (worm); taragacanth sorts (tear) Constituents: Bassorin (swells: 2/3); traganthin (dissolves: 1/3) SA: 5-6% K: galactomannan -> bulk laxative

 

Astragalus gummifer

Karaya most fetid gum Sterculia gum

 

Sterculia urens

Indian Ghatti; alternative fro acacia

 

Anogeissus latifolia

MARINE GUMS

 
 

GUM

SOURCE

CONSTITUENTS

Agar

or

Algae Gelidium cartilagineum Gracilaria confervoides

 

Japanese

Agarose

Isinglas

Agaropectin

Algin

Brown Seaweeds

Mannuronic acid

Macrocystis pyrifera

Carageenan or Irish Moss

Red Algae

Kappa-gelling component Iota-gelling component Lambda non-gelling component

Chondrus crispus

 

Gigartina mamillosa

Danish Agar

Furcellaria fastigiata

Kappa

SEED GUMS

GUM

SOURCE

Psyllium

Seed coat of:

Plantago psyllium Spanish Plantago ovata Blonde

 

Cydonium/Quince Seed

Ripe seed of Cydonia vulgaris

 

Guar Gum or Guaran

Endosperm

of

Cyamopsis

tetragonolobus

 

Locust Bean Gum/Carob Pulp or St. John’s Bread

Endosperm

of

the

seed

of

Ceratonia siliqua

 

MICROBIAL GUM

GUM

SOURCE

NOTES

Xanthan

Action

of

Has a pseudoplastic activity enable toothpastes and ointments to spread easily

Gum

Xanthomonas

campestris

on

carbohydrates

 

C. PLANT EXTRACTIVES

Pectin intracellular cementing materials; partially methoxylated galacturonic acid (swelling); extract of inner

portion of rind of citrus fruits (pomelo, grapefruit, orange, ponkan, lemon, calamansi, dalanghita, apple) and apple pomace; antidiarrheal agent;

o

Kaopectate Kaolin + Pectin -> antidiarrheal preparation

o

Protopectin unripe

o

Pectin (sol) just ripe

o

Pectic acid overripe

D.

GLYCOSIDES

Heteroglycans; “sugar ethers”; BETA form occur in plants; N-, S-, C-, O, alpha or beta; regulatory, protective and sanitary compounds

Components: glycone (acts as vehicle; inactive) and aglycone (genin; basis for classification; active)

CARDIAC GLYCOSIDES

o

Unsaturated steroidal aglycone tests

Libermann-Burchard = blue/green; yellow for saturated

Salkowski = red/violet

 

o

2-deoxy sugar glycone test

Keller-Killanii test = reddish brown)

o

CARDENOLIDES vs BUFADIENOLIDES (C235-B246)

 

CARDENOLIDES

BUFADIENOLIDES

 

- Common (active)

- Rare (Bufo sp); (inactive)

- C-23 α and β unsaturated 5- membered lactone ring

- C-24 doubly unsaturated 6- membered lactone ring

o

Digoxin H 2 O; Digitoxin lipid; Desllanatoside digitalization = rapid

o

Convallaria Convallatoxin Lily of the Valley

o

Apocynum Dogbane cymarine

o

Adonis Pheasant’s Eye – adonitoxin

o

Black Hellebore Xmas Rose hellebrin

o

Strophantus K strophantin (good) G strophantin (bad) (toxic)- Oubain

o

Sqiuill Scillarenin -> expectorant (bufadienolides)

ANTHRAQUINONE GLYCOSIDES

o

Aglycone: Anthracene

 

o

Use: cathartic <drastic>

o

Derivative color: orange

o

Identification Test: Borntranger’s Test

o

Cascara Sagrada Rhamnus purshianus i. Constituents:

 

Cascarosides A and B optical isomers of barbaloin Cascarosides C and D optical isomers of chrysaloin

 

ii. LANE’s Pill – casanthol, purifiesd mix of anthranol glycosides

iii. Cured in MgO for 1 year

 

o

Frangula or Buckthorn Bark Rhamnus frangula

i.

Present in Movicol® Karaya (laxative) + Frangula (cathartics); for constipation

o

Aloe dried latex or juice of Aloe barbadensis or Aloe vera <Curacao aloe>; hybrids of Aloe ferox with Aloe Africana and

Aloe spicata <Cape aloe>; (cathartics and BURNS)

i.

Constituents: barbaloins and aloe emodin

o

Rhubarb glucohein

 

Rheum or Chinese Rhubarb (Therapeutic)

Indian Rhubarb or Himalayan Rhubarb (Ornamental)

Rheum officinale

Rheum emodi

Rheum palmatum

Rheum webbianum

o

Senna dried leaflet of Cassia acutifolia <Alexandria>;

Cassia angustifolia <Tinnevelly>; cultivated in wat lands resembling rice paddies; derivative color: blue green

Constituents: Sennosides A, B, C, and D

o

Chrysarobin from Goa powder, Andira araroba; only anthraquinone glycoside that is NOT used as cathartic because it is very irritating; used as keratolytic; hot benzene is used to extract this substance

SAPONINS foam upon shakin (froth test); bitter, acrid taste; sternutatory (may irritate mucous membrane = sneezing); destroy RBCs of cold blooded animals -> fish poisons; froth, hemolysis, capillary

o

Glycyrrhiza or Licorice dried roots of Glycyrrhiza glabra; increase foaminess of beer

Constituents: glycrrrhizia, glycyrrhziac acid

o

Dioscorea or Yam

Dioscorea spiculiflora contains diosgenin which is a

 

glucocorticoid precursor;

 

Dioscorea floribunda best source of steroids;

Diosgenin anti-inflammatory

o

Ginseng Panax ginseng (Asia); Panax quinquefolius (American); aphrodisiac and an adaptogen

Constituents: panaxosides, ginsenosides, chikusetsusaponins

CYANOPHOIC OR CYANOGENIC GLYCOSIDES

o

Amygdalin (H 2 O and amygdalase) mandelonitrile glucose (H 2 O and prunase) mandelonitrile + glucose benzaldehyde +HCN

o

Rosaceae

o

Emulsin amygdalase and prunase (collectively)

o

APE = A+P+E

o

Guingard’s Test = brick red/red coloration

Bitter almond Prunus amygdalus; source of Laetrile (Vit B17) controversial treatment for sickle cell anemia

Wild cherry Prunus serotina; flavored vehicle, expectorant and sedative

Apricots Prunus armeniaca

ISOTHIOCYANATE GLYCOSIDES

o

Rapeseed Brassicca napus; gluconapin

o

Watercress Nastutium officinale; gluconasturtiin

o

Odor test mustard smell (volatile); garlic (allicin)

o

Ferric chloride test blood red (non-volatile)

o

Black Mustart or Sinapis Nigra Brassica nigra sinigrin Sinigrin/sinalbin (myrosinase)-> allyl/acrinyl

o

White Mustard Brassica alba sinalbin

FLAVONOL GLYCOSIDES flavonoids or bioflavonoids from citrus fruits and soya

o

Rutin and Hesperidin vitamin P or permeability factors; treatment of capillary bleeding secondary to capillary fragility

o

Hesperitin, Diosmin, and Naringen treatment of symptoms of common colds

o

Yellow Pigment rutin and quercetin

o

Milk Thistle Silybum marianum; silibinin, silymarin, hepatoprotective

o

Gingko Ginggko biloba; gingkolides, bilolabides; memory enhancement

ALCOHOL GLYCOSIDES Salicin salix and populous

o

Salix purpurea and Salix fragilis

o

Aglycone: saligenin

o

Anti-inflammatory; anti-rheumatic

o

Tests:

Fehling’s – brick red

Nessler’s – gray

Tollen’s – silver mirror

Schiff’s – recolorization

ALDEHYDE GLYCOSIDES

o Vanilla cured fruit of Vanilla planifolia (orchidaceae) Mexican, Vera Cruz, Bourbon

Constituent: vanillin

Use: flavoring agents

PHENOL GLYCOSIDES

o

Urva ursi dried leaf of Arctostaphylos urva ursi

Constituents: arbutin (hydroquinone + sugar)

Use: astringent and diuretic

o

Poison Ivy (Rhus radicans) and Poison Oak (Rhus

toxicondendron); uroshiol delayed contact dermatitis (type

IV)

LACTONE GLYCOSIDES

o

Coumarin from Tonka beans, Dipteryx odorata; constitutents: dicoumarol bishydroxycoumarin anticoagulant, Warfarin; Test for unsaturated lactone:

Kedde’s = blue-violet

o

Cantharides from dried insect, Cantharis vesicatoria; Russian/Spanish fly; Blistering fly

Constituents: cantharidin-irritant, vesicant and rubefacient

Causes priaprism sustained erection

o

Psoralens photosensitizing furocoumarins; from Bishop’s

flower, Ammi majus

Methoxsalen repigmentation in vitiligo

Trioxsalen

II. TANNINS

Complex substances or polypeptides that are difficult to separate because they do not crystallize

Phenolic in nature; non-crystallizable polyphenols; protein precipitant (astringent); found in barks and leaves

Local sources:

deposit ova); constituent: tannic acid (Gallic + Ellagic = Tannic [GET]) astringent

Chinese/Japanese Gall Rhus chinensis; Aphis sp. gallic acid (Bismuth subgallate protectant; deodorizer for flatulence)

III. LIPIDS

FIXED OILS

   

FATS

 

WAXES

Long

chain fatty

Long chain fatty acids + glycerol

Long

chain

fatty

acids + glycerol

acids

+

high

From vegetables

From animals

molecular weight

Liquid

at

room

Sold at room temp

alcohol

(cetyl

temp

EXCEPTIONS:

alcohol,

stearyl

EXCEPTIONS:

 

Liquid F: Cod liver oil

alcohol)

 

Solid

FO

EXCEPTIONS:

Theobroma,

 

Liquid W: Jojoba oil

Myristica

USE: storage

USE: storage

USE: protectant

 

Fatty Acids

o

Saturated capric, lauric, myristic, palmitic, stearic, arachidic

o

Unsaturated (=) palmitoleic, oleic, linoleic, linolenic, arachodonic

o

Guava Psidium guajava

 

o

Kamachile Pithecolobium dulce

 

Uses: emollients; vehicles for IM injection (COCOPESE);

USP Tests:

o

Duhat Syzigium cumini

 

cathartic (castor oil); soap production; increase caloric value

Characteristics:

 

(TPN)

o

Acidic

 

o

Acid value or Acid number mg of KOH needed to neutralize

Saponification value mg of KOH needed to saponify the

Iodine value g of iodine absorbed in 100g of sample

o

Sharp puckering taste

 

o

Causes precipitation of alkaloids

 

o

free FAs

o

Industrial leather and ink

 

o

Clinical astringents GI or skin, treatment of burns

 

o

esters

Chemical

classes:

(True

tannins

vs

Pseudo

tannins

chlorogenic acid and catechins)

 

Expression cold-pressed oil; hot-pressed oil; only from fixed oils

A.True Tannins animal skin leather; (+) Gold Beater’s Skin Test

i. Hydrolyzable readily hydrolyzed to yield phenolic acids and sugars

Pyrogallol

Leather: bloom

FeCl 3 = blue-black; Br 2 test = (-)

(aka Condensed Tannins/

Phlobatannins) results from condensation of catechin and leucocyanidin

tend to polymerize phlobaphenes (red colored product)

Leather: tanners red

FeCl 3 = green-black; Br 2 test = (+)

ii. Non-hydrolyzable

B.Pseudo Tannin

Hamamelis Leaf Witch Hazel Leaf, dried leaf of Hamamelis viriniana; constituent: hamamelitanin; used for hemorrhoids

Nutgall excrescence obtained from young twigs of Quercus infectoria, Fagacea (when Cynips tinctoria bores a hole to

Rendering fats

Solvent extraction fats; hexane best solvent for extracting fats

Types of oils ability to absorb oxygen; oxygen saturates double bonds forming oxides that polymerize to form films; paint industry

 

IODINE VALUE RANGE

EXAMPLES

Non-drying

<100

Olive; Almond

Semi-drying

100-120

Cottonseed; Sesame

Drying

>120

Linseed; Cod liver oil

Reactions of Lipids

o

Hydrogenation liquid oil to semi-solid fat; passing of H with Pd/Ni in 160-200 o C; shortening and cooking fat

o

Sulfation reaction with sulfuric acid; temp at chilling; sulfates adds to double bonds, surfactants

IV. FIXED OILS

SEED OILS

FIXED OIL

BOTANICAL SOURCE

Cottonseed Oil IM injection; not edible; constituent: gossypol x-> male sterility; ID test: Halphen/Bevan

Gossypium hirsutum

Sesame Seed Oil Benne/Teel Oil; uses: IM injection, edible; constituent:

Sesmum indicum

sesamol (phenol) self-preserving + lignin sesamolin & pyrethrin insecticides; ID test: Bauduoin

Coconut Oil constituents: lauric, myristic, triclycerides

Cocos nucifera

Castor Oil tangan-tangan; ricinoleic (good) - cathartic trcinoleic (good) ricin (toxic) = abrin (jequirity bean)

Ricinus communis

Peanut Oil peanut oil cake; peanut butter; afflotoxin aspergillus (due to improper storage and drying)

Arachis hypogaea

Soybean Oil stigmasterol - steroid; lecithin regulate cholesterol; antilipemic agents

Glycine soja

Corn Oil germ oil cake IM injection; antilipemic agents; Hydrogenated volatile oils = sergers

Zea mays

Safflower Oil antilipemic agents

Carthamus tinctoria

Sunflower Oil antilipemic agents

Helianthus anuus

Ethiodized Oil Injection

Iodine addition product of ethyl ester of fatty acid of Poppy seed

PERICARP OILS

FIXED OIL

BOTANICAL

NOTES

SOURCE

Olive Oil ID test:

Olea

Grades:

europaea

1.

First Grade Virgin Olive Oil

Milon’s

extracted with less pressure

2.

Second Grade Virgin Olive Oil

pulp in #1 is extracted with more

pressure

3.

Technical Oil extracted with

hot water

4.

Sulfur Grade extracted with

Carbon disulfide; inferior quality

5.

Tournant Oil fallen and

decomposing fruits

V. FATS AND RELATED COMPOUNDS

Theobroma Oil Theobroma cocao; food for the gods

o

Uses: cocoa syrup beverage; cocoa butter suppository base (melts at 30-35 o C)

o

Nibs prepared cacao/breakfast cacao

Lanolin purified fatlike substance from wool of sheep Ovis aries, Boviidae; contains 25% water; Uses: water absorbable ointment base; emollient

o Anhydrous lanolin woolfat (contains 0.25% water)

Cod Liver Oil from Gadus morrhua; sclerosing agent to obliterate varicose veins; source of vitamin A and D (Scott’s emulsion)

Undecylenic Acid pyrolysis of ricinoleic acid from castor oil; has antifungal property

Azelaic Acid onolysis of Castor oil; anti-acne

VI. WAXES

Spremaceti head of spermwhale, Physeter macrocephalus; synthetic spermaceti cetyl ester wax

Jojoba Oil seeds of Simmondsia chinensis, Buxaceae; hydrogenated form resembles spermaceti; eicosenoic acids:

eicosenol and docosenol

Beeswas or Yellow Wax honeycomb of bees, Apis mellifera; stiffening agent in plasters and cerates; White Wax bleached yellow wax; myricyl pamitate

Carnuba Wax leaves of Copernicia prunifera; myricyl cerotate

VII. VOLATILE OILS

Odorous principle in carious plants

Colorless and photosensitive; light resistant tight container in a cool and dry place

Undergoes auto-oxidation and resinification

Plant families:

o

Glandular hairs or trichomes (lamiaceae labiatae)

o

Modified parenchymal cells piperaceae

o

Oil tubes or vittae apiacea (umbelliferae)

o

Lysigenous and schizogenous passages pinaceae and rutaceae

Physical characteristics:

o Possess characteristic odors, high refractive index, optically active, immiscible in H 2 O but can be sufficiently be soluble to impart odor in water aromatic water

VOLATILE OILS

FIXED OILS

Distillation Resinification (-) Grease Spot

Saponification Rancidity (+) Grease Spot

Methods of Obtaining Volatile Oils

Distillation

o

Water Distillation dry sample; turpentine oil

o

Water and Steam Distillation dry sample; clove and cinnamon oil

o

Steam Distillation - peppermint and spearmint

o

Destructive Distillation empyreumatic oils (heat without access of air); pinaceae and cuppressiaceae only family to use destructive distillation (“char”)

Enzymatic Actions mustards

Expressions

o Ecuellle and Piquer rolling a fruit in a trough line with sharp tiny projections enough to puncture the rind citrus fruit

o Enfleurage flower petals (or small plant part) on a fatty pomade followed by EtOH extraction Components of Volatile Oil

STEREOPTENE

ELEOPLENESES

- Solid oxidized hydrocarbon portion

- Liquid hydrocarbon portion

- Menthol

- Methysalicylate

- Amenthol

- Encalyptol

- Thymol

- Eugenol

Medicinal and commercial use: fabrication of perfumes

o

Top Notes (smell minute to hour); most volatile product; leave skin readily lemon (limonene most used flavorant), lavender, anise oil

o

Middle Notes (3-6 hours); intermediate tenacity and volatility thyme, neroli and rose oil

o

Base Notes (long hours); low volatility and high tenacity; aka Fixatives = staying power

Musk dried secretion from the preputial follicles of the male musk deer of Asia, Moschus spp muskane

Civet glandular secretion appearing in an outwardly discharging pockets of civet cat, Paracloxutus hermaphrodites

Amber gris most valuable material; pathologic product formed in stomach of spermwhale when if feeds on squid or cattlefish (ambrein)

Constituents of Volatile Oils:

o Terpenes natural products whose structure are made up of isoprene units:

Monoterpene 2

Hydrocarbon Volatile Oils

1. Turpentine Oil Pinus palustris; rectified tuperntine;

terpinhydrate/terpinol expectorant; α and β pinene ** turpentine oil + NaOH = rectified turpentine ** RT + HNO 3 = terpinhydrate/terpinol

2. Peppermint Oil Mentha piperita; menthol

(antipruritic) (+) synthetic, (-) natural; Japanese Peppermint Oil Mentha arvensis; increase menthol concentration; flavorant, carminative, stimulant counter irritant *****INSERT HERE********* Aldehyde Volatile Oil

1. Cinnamon Oil Cinnamomum loureiril; Cinnamomum zeylanicum; Cinnamomum cassia (aka cassia oil); constituent: cinnamaldehyde; uses: flavoring, carminative, antiseptic

2. Lemon Peel Oil rind of the fruit Citrus limon; lemon oil; citral and limonene

3. Citronella Oil leaves of Cymbopogon winterianus tanglad; citronellal; insect repellant

4. Hamamelis Oil Hamamelis virginiana; 2-hexanal; hemorrhodal preparation

Ketone Volatile Oil

1. Camphor Cinnamomum camphora; natural camphor: (+); synthetic camphor: racemic (-); anti pruritic, rubefacient, anti-infective 2. Spearmint Mentha spicata; carvone (-); (+) carvone same odor as caraway (Carum carvi) 3. Buchu Oil Berosma betulina; diosphenol; menstrual problem, carminative, anti-rheumatic 4. Wormwood/Quinghaosu Artemia annua; Artemisia ketone and camphor; anti-malarial artemisinin, artenether, artesunate Phenol Volatile Oil 1. Clove Oil Engenia caryophyllus; eugenol; toothache drops, dental analgesic 2. Thyme Thymus vulgaris; thymol antifungal and antibacterial 3. Creosole Oil Fagus grandiflorus; creosole disinfectant, guiacol 4. Jupiter Tar Juniperus oxycedrus; cadinene; anti- exzema Polytar® Phenolic Ether Volatile Oil 1. Nutmeg/Myristica Oil Myristica fragrans; constitentuents: safrole and myristicin; halloahogen 2. Anise Pimpenella Pimpenella anisum anisaldehyde, transanethol 3. Fennel Freniculum vulgare; fendiole, transanethole

Sesquiterpene - 3

Diterpene - 4

Triterpene - 6

Tetraterpene 8

o

Acetate-Mevalonate Pathways

o

Shikimic Pathway aromatic compound

VIII. RESIN AND RESIN COMBINATION

RESINS amorphous products with complex chemical nature; hard transparent or translucent and when heated they soften and melt; complex mixtures of:

Resin acids

Resin alcohols

Resinotannols

Esters

Resenes

of

B-complex

neutral

substances

devoid

characteristics

RESIN

SOURCE

CONSTITUENTS/NOTES

Rosin/Colophony

Pinus palustris

 

Podophyllum

Podophyllum

Podophyllin caustic agent for warts Peltatin purgative Podophyllotoxin etoposide, tenoposide

peltatum

Eriodictyon/Yerba

Eriodictyon

 

Santa

californicum

Jalap

 

Exogonium

Jalapin

and

purganol

 

purge

drastic purgative

 

Mastic

 

Pistacia

Masticin and mastichic acid

 

lentiscus

Kava/Kava-kava

 

Piper

Styrylpyrones

yangonin,

 

methysticum

kawaiin, methysticin

 

Cannabis/Indian

 

Tops

of

Resin: Hashish

 

Hemp/

Cannabis

Constituets:

THC,

Marijuana/Pot

sativa

Cannabidiol, nabilone

 
 

Duquenois

Test:

violet

on

chloroform layer

 

RESIN COMBINATIONS:

 

Oleoresins volatile oils + resin

 
 

OLEORESINS

SOURCE

CONSTITUENTS

Turpentine/

Pinus palustris

   

Gum Turpentine

 

Capsicum/ Cayenne Pepper African chilles

Capsicum frutescence C. annum var longum (Louisiana long pepper)

Capsaicin

vesicant; irritant

Ginger

Zingiber officinale

Zingebol

and

bisabolene

stomachic;

antibacterial

White Pine

Pinus strobus

   

Balsam

of

Copaifera spp.

   

Comaiba

 

Oleo-Gum-Resin volatile oil + gum + resin

o

Myrrh/Gum Myrrh Commipholra molmol; use: astringent (Astring-o-sol®)

o

Asafetida – Devil’s dung; Ferula asafetida

Balsams mixtures that contain cinnamic acid, benzoinc acid or both or esters of these acids

BALSAM

SOURCE

Storax/Styrax wound healing; perfumery; storesin (α and β – Levant’s storax 50:50); pharmaceutic and compound benzoic tincture (benzoin, storax, tolu balsam, aloe, ethyl alcohol)

Liquidambar

orientalis

Peru Balsam parasiticide

Myroxylon pereirae

Tolu Balsam flavorant, expectorant; compound benzoic tincture (benzoin, storax, tolu balsam, aloe, ethyl alcohol)

Myroxylon balsamum

Benzoin Sumatra; Siam topical compound benzoin tincture

Styrax benzoin

Resin Acids oxyacids (-COOH and phenik)

Glycoresin resin + carbohydrate

IX. STEROIDS

Compounds with CPPP; metabolites of mevalonic pathways

Sterols

o

Cholesterol animals

o

Ergosterol fungi

o

Phytosterol plants

Bile Acids

o Primary

directly from

chenodeoxycholic acid

cholesterol

(liver); cholic acid,

o Secondary fermentation of primary bile acids by intestinal flora; desoxycholic acid, litocholic acid

Steroid Hormones

o

Glucocorticoids carbohydrate metabolism; anti- inflamatory; cortisone, cortisol

o

Mineralocorticoids electrolyte and water balance; aldosterone

o

Sex Hormones Males: androgens, testosterone; Females:

estrogen, progestin

X. ALKALOIDS

Bitter, basic nitrogenous compounds; physiologically active; most of them ends in ine;

Nitrogen can be: Primary amine RNH 2 ; Secondary amine R 2 NH; Tertiary amine R 3 N

All are solids except for: [CANS]

o

Coniine Coniium maculatum; poison hemlock (Socrates)

o

Arecoline scotchbroom (Cysticus coparius), lupin Lupinus mutabilis anti-arrhythmic

o

Nicotine

o

Sparteine

Alkaloidal Reagents form double salts with compounds of mercury, gold, platinum, and other heavy metals

o

Wagnner’s Reagent – iodine in KI (red-brown)

o

Mayer’s Reagent – potassium mercuric iodide (cream)

o

Valser’s Reagent – mercuric iodide (white)

o

Dragendorff’s Reagent – potassium bismuth iodide (orange)

o

Bouchdart’s Reagent – iodine in KI, most sensitive

o

Marme’s Reagent – K cadmium iodide

o

Sonnencheims’s Reagent – phosphotungstic acid

o

Hager’s Reagent – picric acid

o

Gold compounds

o

Tannic acid

A.

PYRIDINE-PIPERIDINE ALKALOIDS

Nicotine leaves of Nicotiana tabacum; use: CNS stimulant; smoking deterrent (Nicoret®)

Areca, Areca Nut or Betel Nut dried ripe seed of Areca catechu; arecoline anthelminthic-taenicid; tannin content causes oropharengeal cancer; catechutannin cancer causing

Lobella Indian tobacco; Lobella inflata; Lobeline CNS stimulant and smoking deterrent (Bantron®)

B. TROPANE ALKALOIDS (Solaneous alkaloids)

Belladona Atropa belladonna; anticholinergic, mydriatic; (-) hyoscyamine atropine]

Hyocyamus or Henbane leaves of Hyscyamus niger, 0.04%; hog +bean toxic to swine

Egyptian Hyoscyamus or Egyptian Henbane hyoscyamus muticus, 1.5%

Duboisia Duboisia myoporoides

Withania

Withania

somnifera;

atropine3

commercial

sources

of

Stramonium or Jimson Weed/Jamestown Weed Datura stramonium Solanaceae; Talumpunay; used for asthma and COPD burned then vapors are obtained

Mandragora or European Mandrake/Satan’s Apple – roots of Mandragora officinarum; mandragorine; potent poison

Cocaine Huanuco coca Erythroxylon coca; Truxillo coca E. truxillense; crack/coke; psychomotor stimulant, local anesthetic; Brompton’s cocktail

Atropine

and

cycloplegic; antidote for cholinesterase inhibitors; (+) inotropic

antispasmodic;

antisialogogue;

mydriatic

agent

Scopolamine or Hyoscine treatment form motion sickness; Trans-scop® or Transderm®

C. QUINOLINE ALKALOIDS

Cinchona Red cinchona bark Cinchona succirubra; Yellow cinchona bark C. calisaya; “cinchonism”; Quinine, Quinidine – antimalarial; Thalleioquin test = fine blue fluorescence then green ppt

Cuprea Remijia purdieana, Cupreaceae; commercial source of quinidine

D. ISOQUINOLINE ALKALOIDS

Ipecac dried rhizome and rood of Cephaelis ipecacuanha; constituent: emetine or methylcephaeline; use: ipecac syrup emetic

o

Ipecac fluidextract is 14 times more potent

o

Ipecac + Opium = Dover’s Powder (diaphoretic)

o

Paregoric camphorated opium tincture

o

Laudanum deodorized opium tincture

Sanguinaria Canadensis;

constituents: saguinarine; use: stimulating expectorant and emetic

Tubocurarine Chloride aka curare or south American arrow poison; Strychnos castelnaei; constituent: tubocurarine skeletal muscle relaxant

Sanguinaria

or

Bloodrood

o

Pot clay

o

Tube bamboo

o

Calabash gourd

o

Standardization of Tubocurarine Head Drop Assay in Rabbits least amount of drug capable of producing muscle relaxation so that head of animal drops in a characteristic manner

Opium or Gum Opium unripe poppy seed capsules of Papaver somniferum; only legal source is India; stone of immortality; Marquis Test: opiods (purple); synthetic

o Diacetlymorphine Heroin; acetylation of morphin; increase danger of habit formation (very potent)

o

Hydromorphone more potent analgesic; less frequent SE

o

Apomorphine condensation of morphine + HCl; use:

emetic

o

Hydrocodone - antitussive

o

Opiates natural source

Morphine Serturner; most important, most abundant, narcotig analgesic

Codeine P. Robiquet; most widely used opium alkaloid; obtained from methylation of morphine; methymorphine antitussive

Noscapine non-narcotic opium alkaloid; antitussive; anarcotin/narcotine

Papeverine smooth muscle relaxant, antitussive

Thebane

E. INDOLE ALKALOIDS (Tryptophan)

Rawolfia Serpentina dried root of Raubolfia serpentina; constituent: reserpine treatment of snake bites to insanity, hypotensive effects, sedative and tranquilizong properties

Chichirica/Catharanthus/Vinca Cantharanthus roseus; constituents: vinscristine and vinblastine; lymph, hodgkins; aka Periwinkle

Nux Vomica dried ripe seed Strychnos nux vomica; Strychnos Ignatii (St. Ignatius Bean) commercial source of strychnine; constituents: strychnine (toxic central stimulant) Mandelin’s Test = violet; Brucine (alcohol denaturant)

Physostigmine/Eserine local sources: calabar, ordeal, or Esere Bean; from Physostigma venenosum; treatment of Glaucoma

Ergot dried sclerotium of Claviceps purpurea on rye, secale cereal; constituents: ergonovine (ergometrine & metylsergide prophylaxis for migraine) oxytoxic agent, ergotamine

o Lysergic Acid Diethylacmide most active and most specific psychomimetic drugs

F. IMIDIZOLE ALKALOIDS

Pilocarpine leaflets of Pilocarpus jaborandi; treatment of glaucoma

G. STEROIDAL ALKALOIDS

Green Hellebore/Veratum viride roots of Veratrum viride; use: cardiac depressant; (-) inotrope

Black Hellebore cardiac stimulant; (+) inotrope

White Hellebore/European Hellebore roots of Veratum album; insectesies

H. ALKALOIDAL AMIDES

Ephedra/Ma Huang ephedrine; overground portion of Ephedra sinica; nasal decongestant; bronchodilator

Colchicine Colchicum autumnale, Liliaceae; used in plant genetics because it can double the chromosomes

Khat/Abyssynian Tea fresh leaces of Catha edulis; constituents: cathinone amphetiamine like effects

Peyote/Mescal Buttons aka “shrooms”dried tops of Lophophora williamsii; hallucinogenic and euphoric agent; constituent: mescaline (psilycybe psilocybine)

I. PURINE ALKALOIDS/METHYLXANTHNES

Cannot be precipitated by any alkaloidal reagents

Caffeine 1,3,7-trimethylxanthine *INSERT STRUCTURES*

o

Kola, Cola or Kolanuts dried cotyledon of Cola nitida

o

Coffee Bean dried seeds of Coffea Arabica

o

Amaic Acid Test: Red-brown/transient purple

o

C. robusta; C. liberica

Chlorogenic acid + caffeine (+ caffeole) ()

Decaffenieted coffee 0.08%

o

Phosphodiesterase Inhibitors diuresis; increase gastric secretions; inhibit uterine contraction; weak (+)

chronotropic and inotropic effects

Theophylline 1,3-dimethylxanthine; leaf buds of Camellia sinensis; treatment of bronchial asthma; tocolytic agent

o Aminophylline semi-synthetic theophylline derivative treatment of bronchial asthma

Green Tea (Fresh) China and Japan

Black Tea (Fermented) India and Sri Lanka (Ceylon)

Theobromine 3,7-dimethylxanthine; seeds of Theobroma cacao; diuretic in cardiac and pulmonary edema