tannins and vescalagin

In this study the effect of growth medium strength on the minimum inhibitory concentration (MIC) of different tannins and tannin extracts against

Topics: Bacteriological Techniques; Culture Media; Escherichia coli; Gallic Acid; Hydrolyzable Tannins; Microbial Sensitivity Tests; Mimosa; Molecular Structure; Plant Extracts; Plants; Quercus; Tannins

Three new phenolic compounds named whiskey tannins A and B and carboxyl ellagic acid were isolated from commercial Japanese whiskey, along with gallic acid, ellagic acid, brevifolin carboxylic acid, three galloyl glucoses, a galloyl ester of phenolic glucoside, 2,3-(S)-hexahydroxydiphenoylglucose, and castacrenin B. Whiskey tannins A and B were oxidation products of a major oak wood ellagitannin, castalagin, in which the pyrogallol ring at the glucose C-1 position of castalagin was oxidized to a cyclopentenone moiety. These tannins originated from ellagitannins contained in the oak wood used for barrel production; however, the original oak wood ellagitannins were not detected in the whiskey. To examine whether the whiskey tannins were produced during the charring process of barrel production, pyrolysis products of castalagin were investigated. Dehydrocastalagin and a new phenolcarboxylic acid trislactone having an isocoumarin structure were isolated, along with castacrenin F and ellagic acid. However, whiskey tannins were not detected in the products.

Topics: Alcoholic Beverages; Ellagic Acid; Flavonoids; Hydrolyzable Tannins; Oxidation-Reduction; Phenols; Polyphenols; Quercus; Tannins; Wood

The gastroprotective effects of 70% acetone extracts of Quercus suber and Quercus coccifera leaves and of tannins (pedunculagin, castalagin, phillyraeoidin A, and acutissimin B) purified from these extracts were examined in the mouse using the ethanol-induced gastric ulcer model. Both extracts (25, 50, and 100 mg/kg), given orally, prevented the formation of ethanol-induced lesions in the stomach. The percent protection varied between 68 and 91%. Purified tannins (50 mg/kg) were also effective in protecting the stomach against ethanol, and the percent protection varied from 66 to 83%. Castalagin was the most potent. Both extracts and all of the tannins tested (10, 25, and 50 microg/mL) strongly inhibited (55-65%) the lipid peroxidation of rabbit brain homogenate. These results suggest that the gastroprotective effects of extracts of Q. suber and Q. coccifera leaves and the purified tannins in this experimental model are related to their anti-lipoperoxidant properties.

Topics: Acetone; Animals; Biphenyl Compounds; Catechols; Ethanol; Hydrolyzable Tannins; Lipid Peroxidation; Male; Mice; Plant Extracts; Plant Leaves; Quercus; Rabbits; Stomach Ulcer; Tannins

Brandies, cognac, armagnac, whiskeys, and rums are aged in oak barrels to improve their organoleptic properties. During this period, numerous compounds such as ellagitannins are extracted from the wood and can subsequently be transformed into new derivatives by chemical reactions. Model solutions of castalagin and vescalagin have been studied to determine the behavior of polyphenols in ethanol-water. Upon prolonged exposure to 40 and 70% (v/v) ethanol at room temperature, hemiketal derivatives containing ethoxy groups have been characterized by LC/MS and NMR. These compounds further evolve to afford the corresponding ketals. They have also been detected in the extracts of oak wood stored under similar conditions.

Topics: Alcoholic Beverages; Antihypertensive Agents; Biphenyl Compounds; Catechols; Chromatography, High Pressure Liquid; Ethanol; Food Handling; Hydrolyzable Tannins; Molecular Conformation; Molecular Structure; Solutions; Tannins; Wood

The ellagitannins 2,3-(S)-hexahydroxydiphenoyl-glucose, pedunculagin, vescalagin, and castalagin; the flavanoellagitannins acutissimin A, acutissimin B, eugenigrandin A, guajavin B, and stenophyllanin C; and the procyanidinoellagitannin mongolicanin have been isolated from the bark of Quercus petraea. The ellagitannin fraction had a weak antisecretory effect.

Topics: Anthelmintics; Biphenyl Compounds; Catechols; Hydrolyzable Tannins; Magnetic Resonance Spectroscopy; Tannins; Trees