Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes

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TANNINS
Introduction
The term tannin was first time coined by Seguin in 1796. This term was used to denote substances present in plant extract which react with protein of animal hide, prevent their putrefaction (process of decay of organic materials) and convert hide and skin into leather.

Definition
Complex substances that usually occur as mixtures of polyphenols that are very difficult to separate since they don't crystallize, are called tannins. OR Tannins are polyhydroxy phenolic compounds.

Physical Properties
Color: Taste: State: Solubility: Dark brown or reddish brown Puckering taste Non-crystalline Soluble in water, alcohol, dilute alkalis, glycerols and acetone.

Chemical properties
(i) (ii) (iii) (iv) (v) (vi) Precipitation Anti-oxidizing properties Astringent Carcinogenicity Reaction with salts Reaction with potassium ferricyanide and ammonia

(i) Precipitation: Tannins have ability to precipitate solutions of; Gelatin. Alkaloids. Glycosides. Heavy metals. Proteins. (ii) Anti-oxidizing properties: Because of accumulation of OH group on small size nucleus, these agents have anti-oxidant nature.

Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
(iii) Astringent:

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Tannins have property to react with protein of mucous membrane and cause precipitation (iv) Carcinogenicity: Prolong use of tannin containing plant material is hazardous because it causes cancer. Habitual use of Areca catechu can cause oral and esophageal cancer. (v) Reaction with Salts:

(vi) Reaction with Potassium ferricyanide and Ammonia:

Importance of Tannins
Medicinal Uses: Antidote. Antiseptic. Algicidals. Astringents. Anti-carcinogenic.

Industrial Uses: Ink manufacture. Vegetable tanning. Preservatives. Biological Activities: Inhibition of lipid per oxidation. Decrease in blood urea nitrogen content. Inhibition of plasmin. Lipolysis in fat cells.

Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes Chemical Classification

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Based on identity of phenolic nuclei involved and on the way they are joined.

Tannins

Hydrolysable tannins

Condensed tannins

Complex tannins

(i) Hydrolysable Tannins:

These tannins are hydrolyzed by enzymes or acids. Precursors: Phenolic acid (Gallic acid, Ellagic acid) Glucose residue Between phenolic acids and glucose sugar, there is ester linkage.

Properties:

Types:
Hydrolysable tannins

Gallitannins

Ellagitannins

Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes

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Gallitannins Occurrence Rhubarb Clove Hamamelis Upon acid hydrolysis of Gallitannins, Gallic acid is produces. * Rapidly soluble in water. * Free Gallic acid, in plant, is converted to gluco Gallitannins.

Ellagitannins Pomegranate Eucalyptus Upon acid hydrolysis of Ellagitannins, Ellagic acid is produces. * Slowly soluble in water. * Present in plants in open and ring forms as Hexa hydroxy diphenic acid.

Hydrolysis

Properties

(ii) Condensed Tannins

These tannins are derivatives of Flavonoid, catechin, flavonol-3-4-diol. Precursors: Flavonoid Catechin Flavonol-3-4-diol

Properties: When heated with acids, these are self condensated, polymerized and converted to insoluble red colored complexes, called Phlobaphenes.

Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes

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Examples Hamamelis Cinchona Cinnamon

(iii) Complex Tannins

These tannins are mixtures of both, hydrolysable and condensed tannins Examples: Tea Quercus Castanea Types (2nd Classification of tannins based on complexity): Tannin is a substance which is detected qualitatively by tanning test (The Gold Beaters skin test) and quantitatively by its adsorption on standard hide powder. Depending upon this, tannins are of two types; 1) True tannins. 2) Pseudo tannins.

Tannins

True tannins
Difference: True tannins Polyhydroxy phenolic compounds which convert animal hide to leather by precipitating proteins and give positive Gold beaters skin test, are called true tannins. Molecular weight is 1000-5000

Pseudo tannins
Pseudo tannins Phenolic compounds of plant origin that don't convert animal hide to leather but do give positive Gold beaters skin test, are called pseudo tannins. Molecular weight is less than true tannins.

Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes Identification Tests (for Tannins)
1. Color reaction: Tannins give color reaction with iron.

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2. Matchstick test: Dip matchstick in plant extract. Dry it. Moisten it with hydrochloric acid. And warm near flame. Wood will turn pink or red in color due to phloroglucinol. 3. Gelatin test: Solution of tannin (0.5%-1%) precipitates 1% solution of gelatin containing 10% sodium chloride. 4. Phenazone test: Take 5ml of aqueous extract of drug. Add 0.5grams of sodium acid phosphate. Warm it and cool. Filter solution. To the filtrate, add 2%solution of Phenazone. Tannins will be precipitated. Precipitates will be bulky and colored. 5. Gold beaters skin test: Gold beaters skin is a membrane prepared from intestine of Ox and behaves similarly to un tanned skin. Soak a small piece of Gold beaters skin in 2% hydrochloric acid. Rinse it with distilled water. Place it in solution to be tested for 5 minutes. Wash in water and transfer to 1% solution of ferrous sulphate. Black or brown color of skin indicates presence of tannins. *** It is a quantitative test and +ive only for true tannins.

Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes

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6. Catechin test: Catechin when heated with acid produce phloroglucinol. Phloroglucinol can be detected with matchstick test. 7. Test for chlorogenic acid: Treat extract containing chlorogenic acid with aqueous ammonia and expose it to air. Green color will appear gradually.

Plants, Containing Tannins

a) Hamamelis
Botanical origin: Family: Part used: Hamamelis virginiana. Hamamelidaceae. Dried leaves.

Collection: Leaves are collected throughout summers. Drying is done in open air, preferably under shade to preserve green color. Constituents: Gallitannins Ellagitannins Free gallic acid Pro-anthocyanadins Hamamelase Uses: Astringent Anti-hemorrhagic Anti-inflammatory Anti-carcinogenic

b) Catechu
Botanical origin: Family: Part used: Uncaria gambir Rubiaceae Dried aqueous extract from leaves and young twigs.

Collection: Boil leaves and twigs in water. Evaporate to a pasty consistency. Paste is put in cubes and dried in sun.

Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
Constituents: Catechin Catechutannic acid Catechu red Quercitin Gambir flourescin Uses: Astringent Dying Tanning industry

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c) Nutt gall
Botanical origin: Family: Part used: Quercus infectoria. Fagaceae. Galls obtained from twigs.

Formation of galls: Galls are pathological outgrowth formed on twigs of tree. Galls arise due to deposition of eggs by small insect Adleria galactinctoria. Steps are; Early summers, insects lay eggs on twigs Larvae come out from eggs and enter soft epidermis. Larvae secretes enzyme that stimulates abnormal growth around larvae. Starch in the tissue gets converted to sugars and stimulate cell division. Disappearance of starch causes cell shrinkage. Central cavity is formed in which larvae and pupae grows. Larvae remains in gall for 5-6months. Mature insect bores the covering of gall and escapes away. Galls are collected before escaping of insect. Constituents: Tannic acid Gallic acid Ellagic acid Roburic acid Syringic acid Calcium oxalate crystals Uses: Haemostatic Antidote for alkaloidal poisoning Astringent

Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes

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LIPIDS
INTRODUCTION Lipids constitute a broad group of naturally occurring molecules which include waxes, fats, sterols, fat-soluble vitamins, monoglycerides, diglycerides, phospholipids and others. FIXED OILS Fixed oils are esters of fatty acid with glycerol. PROPERTIES Non-irritant Odorless Tasteless Non-volatile Insoluble in water and soluble in organic solvents Produce greasy mark on paper Upon heating strongly, undergo decomposition Upon hydrolysis, yield glycerol and fatty acid

CHEMISTRY Fixed oils are esters of fatty acid with glycerol. These may be; Monoglycerides Diglycerides Triglycerides CLASSIFICATION On the basis of their ability to absorb Oxygen from air; these are classified as: a) Drying oil b) Non-drying oil c) Semi-drying oil a) Drying oil when exposed to air, undergo oxidation and form tough and hard film. These are usually used in paints and varnishes. For example; Linseed oil

Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes

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b) Non-Drying oil These oils neither undergo oxidation nor form tough and hard film. For example; Olive oil c) Semi-Drying oil When exposed to air, undergo little bit oxidation and form tough and thin film. For example; Cotton seed oil METHODS OF OBTAINING FIXED OILS Direct expression Solvent extraction Steam treatment + extraction

COTTON SEED OIL Botanical origin: Family: Part used: Collection: Gossypium herbaceum Malvaceae Seeds

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
Constituents: Glycerides of; Linoleic acid Oleic acid Palmitic acid Stearic acid Arachidic acid Myristic acid

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Uses: Food Emollient Vehicle for injections Preparation of hydrogenated vegetable oils Soap manufacture

Toxicity: Occur due to intravenous administration of Cottonseed oil emulsion. Acute toxicity includes following symptoms; Fever Pain in back or chest Nausea Vomiting Headache Tachycardia Dizziness

Chronic toxicity includes following symptoms; GIT bleeding Mild anemia Defects in blood clotting Treatment of toxicity: IV hydrocortisone sodium succinate 50grams Promethazine 50mg Heparin (to aid clearance of fat from circulation)

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
CASTER OIL Botanical origin: Family: Part used: Collection: Ricinus communis Euphorbeaceae seeds

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Constituents: Glycerides of; Ricinoleic acid Oleic acid Linoleic acid Stearic acid Toxicity: Excessive oral administration in larger doses Results in toxicity Symptoms include; Nausea Colic Vomiting severe purgation Electrolyte imbalance Uses: Purgative Emollient Preparation of zinc and castor oil ointment Sterilized castor oil as soothing agent in eye
Oily vehicle for eye drops
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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
LINSEED OIL Botanical origin: Family: Part used: Constituents: Glycerides of; Isolinoleic acid Linoleic acid Stearic acid Myristic acid Palmitic acid Uses: Linum usitatissimum Linaceae Seeds

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In veterinary medicine as Purgative

OLIVE OIL Botanical origin: Family: Part used: Constituents: Glycerides of; Oleic acid Linoleic acid Stearic acid Arachidic acid Palmitic acid Uses: Laxative Nutrient Emollient Demulcent Olea europaea Oleaceae Ripe fruit

PEANUT OIL Botanical origin: Family: Part used: Arachis hypogaea Leguminosae Seeds

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
Constituents: Glycerides of; Oleic acid Linoleic acid Stearic acid Arachidic acid Behenic acid Lignoceric acid Palmitic acid

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Uses:

Vehicles in emulsions, liniments, plasters, soap Ink manufacture Preparation of hydrogenated vegetable oil

CORN OIL Botanical origin: Family: Part used: Constituents: Glycerides of; 1. 2. 3. 4. 5. 6. 7. Uses: 1. 2. 3. Vehicles in pharmaceutical and cosmetic preparation Solvent for injections Nutrient Oleic acid Linoleic acid Stearic acid Arachidic acid Palmitic acid Myristic acid Lignoceric acid Zea mays Gramineae Embryo

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
SWEET ALMOND OIL Botanical origin: Family: Part used: Constituents: Glycerides of; 1. 2. 3. 4. Oleic acid Linoleic acid Palmitic acid Myristic acid Uses: 5. 6. 7. 8. Prunus amygdalus Rosaceae Seeds

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Nutrient Demulcent Emollient Preparation of cold creams, hair lotions and toilet articles

COCONUT OIL Botanical origin: Family: Part used: Constituents: Glycerides of; 1. Lauric acid 2. Myristic acid 3. Capric acid 4. Caprylied acid 5. Caproic acid 6. Oleic acid 7. Palmitic acid 8. Stearic acid Cocos nucifera Palmae Dried solid part of endosperm

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
Uses: Nutrient Confectionaries Cosmetics Ointment base MUSTARD OIL Botanical origin: Family: Part used: Constituents: Glycerides of; Uses: Linoleic acid Oleic acid Erucic acid Brassica juncea Cruciferae Seeds

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Nutrient Rubefacient In preparation of liniments In massages SESAME OIL

Botanical origin: Family: Part used: Constituents: Glycerides of;

Sesamum indicum Pedaliaceae Seeds

Linoleic acid Oleic acid

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
Stearic acid Palmitic acid Arachidic acid

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And other components include; Sesamin sesamolin

SAFFLOWER OIL Botanical origin: Family: Part used: Constituents: Glycerides of; Uses: Nutritive Palmitic acid Stearic acid Arachidic acid Oleic acid Linoleic acid Linolenic acid Carthamus tinctorius Compositae Seeds

SUNFLOWER OIL Botanical origin: Family: Part used: Constituents: Helianthus annus Compositae Seeds

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
Glycerides of; Uses: Nutritive Preparation of hydrogenated products Preparation of paints, varnishes and soap Palmitic acid Stearic acid Arachidic acid Oleic acid Linoleic acid Behenic acid

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THEOBROMA OIL Botanical origin: Family: Part used: Constituents: Uses: Ingredient in cosmetic ointment in pharmacy for coating pills Preparation of suppositories Diuretic 2% Theobromine 40-60% solid fat Mucilage Theobroma cacao Sterculiaceae Seeds

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
LENOLIN

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Lanolin is also called wool wax or wool grease. It is a yellow waxy substance secreted by the sebaceous glands of wool bearing animals. Most lanolin used by humans comes from domestic sheep.

Constituents: A typical high purity grade of lanolin is composed predominantly of; long chain waxy esters

lanolin alcohols lanolin acids lanolin hydrocarbons It has been estimated that there may be between 8,000 and 20,000 different types of lanolin ester present in lanolin. Production: Lanolin is extracted by washing the wool in hot water with a special wool scouring detergent to remove dirt, wool grease (crude lanolin), suint (sweat salts), and anything else stuck to the wool. The wool grease is continuously removed during this washing process by centrifugal separators, which concentrate the wool grease into a wax-like substance melting at approximately 38 C (100 F). Applications: Lanolin and its many derivatives are used extensively in high value cosmetics, facial cosmetics, lip products etc Lanolin is used commercially in many industrial products ranging from rust-proof coatings to lubricants. Lanolin is often used as a raw material for producing cholecalciferol (vitamin D3). Anhydrous lanolin is also used as a lubricant for brass instrument tuning slides. Lanolin can also be restored to woolen garments to make them water and dirt repellent.

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
BEES WAX Zoological origin: Family: Source: Production:

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Apis mellifera/ Apis dosarta/ Apis cerana/ Apis indica/ Apis florea Apidae Bee hives

Worker bees have eight wax-producing mirror glands. The size of these wax glands depends on the age of the worker and after daily flights begin these glands gradually atrophies. The new wax scales are initially glass-clear and colorless becoming opaque afterwards. The wax of honeycomb is nearly white, but becomes progressively more yellow or brown by incorporation of pollen oils and propels.Honey bees use the beeswax to build honeycomb cells. In which their young are raised and honey and pollen are stored. For the wax-making bees to secrete wax, the ambient temperature in the hive has to be 33 to 36C (91 to 97 F).To produce their wax, bees must consume about eight times as much honey by mass. When beekeeper extracts the honey, they cut off the wax caps from each honeycomb cell with an uncapping knife or machine. The wax may further be clarified by heating in water. Constituents: Beeswax is a tough wax formed from a mixture of several compounds. Its main components are; Palmitate Palmitoleate Hydroxypalmitate oleate esters of long-chain (30-32 carbons) Aliphatic alcohols with the ratio of triacontanyl Palmitate to cerotic acid, the two principal components, being 6:1.

Applications: Making of honeycomb foundation Beeswax is an ingredient in surgical bone wax Purified and bleached beeswax is used as: Coating for cheese Protectant of the food as it ages Food additive As a component of shoe polish, furniture polish

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
As a component of modelling waxes

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JOJOBA OIL Botanical origin: Family: Part used: Simmondsia chinensis Simmondsiaceae seeds

Constituents: This oil is rare in that it is an extremely long (C36-C46) straight-chain wax ester Uses: In cosmetics as a moisturizer As a carrier oil for specialty fragrances Bio-diesel fuel for cars and trucks Biodegradable lubricant.

SPERMACETI Source: Spermaceti is a wax present in the head cavities of the whale i.e. Physeter macrocephalus. Extraction: Spermaceti is extracted from oil by Crystallization at 6 C. When treated by pressure and a chemical solution of caustic alkali, spermaceti forms brilliant white crystals that are hard but oily to the touch, and are devoid of taste or smell.

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
Uses: Ingredient in cosmetics Leather working Lubricants Making of candles Dressing of fabrics Pharmaceutical excipient (in ointments) CARNAUBA WAX Botanical origin: Family: Part used: Constituents: Carnauba consists mostly of; Aliphatic esters Diesters of 4-hydroxycinnamic acid -hydroxycarboxylic acids Fatty acid alcohols Methoxy cinnamic acid Uses:

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Copernicia cerifera/ Copernicia prunifera Arecaceae Leaves

Automobile waxes Shoe polishes Dental floss Food products such as sweets, Floor and furniture waxes and polishes Use for paper coatings Emollient

FATS VS FIXED OILS

Fats Solid at room temperature Contain saturated glycerides e.g. glyceryl stearate Fixed oils Liquid at room temperature Contain unsaturated glycerides e.g. glyceryl oleate

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Pharmacognosy By Sir Tanveer Khan

Lecture: Tannins + Lipids + Oils + Waxes
VOLATILE OILS VS FIXED OILS
Volatile oils Volatilize at room temperature Obtained by distillation Leave no spot after evaporation Cannot be saponified Mixtures of oleoptenes and stereoptenes High refractive index

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Fixed oils Don't get volatiles at room temperature Obtained by extraction After evaporation, do leave spot Can be saponified Esters of fatty acid with glycerol Low refractive index

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