PHARM.

D Chemical Pharmacognosy- I Lecture 31 May 18th, 2011

TANNINSTANNINS-II

M. Ahsan Khalid, B.Pharm, Pharm. D B.Pharm, M.Phil Scholar (RIPS/RIU) HIPSHIPS-HUKIC

3 major classes of tannins are: Hydrolysable tannins on heating with hydrochloric or sulphuric acids yield gallic or ellagic acids Eg- Turkish galls, hemamalis, Eghemamalis, pomegranat NonNon-hydrolysable tannins on heating with hydrochloric acid yield phlobaphenes like phloroglucinol Eg- black catechu, pale catechu, Egkinos Pseudo tannins are low molecular weight compounds associated with other compounds. They do not answer gold beater skin test unlike hydrolysable and condensed tannins. Eg- tea, Egcoffee They have catechins which give rise to the peculiar odour. odour.

Classification of Tannins

In higher plants, two groups of tannins are generally distinguished, which differ by their structure, as well as their biogenic origin hydrolysable tannins and condensed tannins. Hydrolysable Tannins: Tannins: Ellagitannins Gallotannins

Hydrolysable Tannins

Hydrolyzable tannins are hydrolyzed by weak acids or weak bases to produce carbohydrate and phenolic acids. Examples of gallotannins are the gallic acid esters of glucose in tannic acid, (found in leaves and bark of many plant species)

Hydrolysable Tannins

They may be hydrolyzed by acids or enzymes such as tannase, tannase, (products being sugar and phenolic acids). Formed by several phenolic acids which are united by ester linkages to a central sugar (glucose) molecule. Hydrolysable tannins are therefore esters of a sugar and phenolic acid molecules. molecules. The phenolic acid is in the case of gallotannins gallic acid in the case of ellagi-tannins hexahydroxydiphenic ellagiacid (HHDP) and its oxidized derivatives (HHDP) (dehydrohexahydroxydiphenic acid). Ellagitannins are found in Herb Robert (Geranium species, Meadowsweed and Oak bark).

Egs of Hydrolysable Tannins

Gallotannins: rhubarb, cloves, red rose petals, bearberry leaves, Chinese galls, Turkish galls, hamamelis, chestnut and maple Ellagitannins: Ellagitannins: pomegranate rind, pomegranate bark, eucalyptus leaves, some Australian kinos, chestnut (Castanea spp), and oak bark.

Ellagitannins

With more than 500 natural products characterized so far, ellagitannins are the largest group of known tannins. Ellagitannins are formed from the gallotannins by the oxidative coupling of at least two galloyl units.

Gallotannins
Gallotannins are the simplest hydrolysable tannins, containing a polyphenolic and a polyol residue. Polyol: alcohol with multiple hydroxyl groups. Most of the gallotannins isolated from plants contain a polyol residue derived from D-glucose.

Gallotannins

Hydrolyzable TANNIN CONTAINING HERBS

Turkish Galls
Definition: Turkish galls are vegetable growths formed on the young twigs of the dyers oak, Quercus infectoria (Fagaceae). Fagaceae). They result from the decomposition of the eggs of the gall-wasp gallAdleria gallaetinctoriae. gallaetinctoriae. If the galls are not collected and dried, the mature insect bores out of the gall and escapes.

Turkish Galls: Collection

Galls are collected by peasants of Turkey and Syria. Syria. In the summer gall wasps lay eggs on the twigs. It penetrates the soft epidermis of the plant & soon forms a larvae. This larvae develops into galls. Ideally galls should be collected before the mature insect comes out. After collection they are graded according to colour into 3 grades: blue, green and white. Colour changes occur due to enzymatic secretions of insect.

Turkish galls - Constituents

50 70% tannin gallotannic acid. Tannic acid: hydrolysable tannin (consisting of gallic acid and glucose). glucose). Gallic acid Ellagic acid Sitosterol Starch Calcium oxalate Syringic acid (CNS-active (CNScomponent)

Extraction of tannic acid:

A mixture of alcohol-ether is added to alcoholgalls. When water is added to this extract the tannic acid enters the alcohol layer. The ether layer can be discarded. After precipitation with a non-polar solvent nonit occurs as a white shiny powder.

Turkish Galls Uses & Allied Drugs

Uses

Allied Drugs

Used as a source of tannic acid. Tannic acid is used as an astringent and styptic. Used for tanning and dyeing. Ink manufacturing.

Chinese and Japanese Galls Hungarian Galls

Pomegranate Rind

Definition: Pomegranate consists of the fruit pericarp, or the stem and bark of Punica granatum.

Punica granatum - Punicaceae

History: Mentioned in Bible and Quran. Used as an Ancient Medicine (Indian and Arab physicians).

Active Constituents: Punica

Fruit: Gallo/ellagitannins

Mainly punicalin and punicalagin

Alkaloids are present in the bark, leaves and young fruit. (no alkaloids are present in the rind).

Pomegranate: Actions & Uses

Therapeutic category: AntiAnti-diarrhoeal, antiantihelminthic. Uses: Bark is traditionally used to treat worms. Dried fruit rind or fruit pulp is used to treat diarrhoea. A tea is normally made with honey (bitter taste).

Punica granatum: Pomegranate granatum:

Pharmacological Effects: AntiAnti-diarrhoeal effect Tannins

AntiAnti-helminthic effect alkaloids They interact strongly with the nicotinic Acetylcholine receptors: cause tapeworms to lose their grip, and are expelled from the body. NOTE: Alkaloids are toxic and self medication may be dangerous.

Punica granatum and Alzheimers

Research conducted on mice that were given pomegranate juice, experienced 50% less degeneration of brain cells, compared to their counterparts, who drank only sweetened water. This indicates that pomegranate juice may help cut risk of Alzheimers disease.

Punica granatum & CV Health

Tests showed that pomegranate juice reduced the effects of stress on human blood vessel cells by stimulating the production of nitric oxide. This chemical is thought to help keep arteries open and keep blood flowing. Additional research shows pomegranate juice can both reverse and prevent atherosclerosis.

Researchers say the beneficial effects of pomegranate juice on hardening of the arteries are likely largely due to its high antioxidant content. The study showed that the antioxidant level in pomegranate juice was higher than that found in other fruit juices, including blueberry, cranberry, orange, and even red wine.

Punica granatum & Cancer

Drinking 8 ounces of pomegranate juice daily can suppress prostate cancer activity in men with recurrent prostate cancer, according to a study presented at the annual meeting of the American Urological Association in San Antonio. A recent study at the University of WisconsinMadison using a Wisconsin mouse model shows that consuming pomegranates could potentially help reduce the growth and spread of lung cancer cells or even prevent lung cancer from developing.