Sulfated c-glycoside, method for isolating same and method...

C - Chemistry – Metallurgy – 07 – D

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C07D 407/04 (2006.01) A61K 31/352 (2006.01) A61K 36/00 (2006.01) A61P 17/00 (2006.01) A61P 29/00 (2006.01) A61P 35/00 (2006.01) A61P 37/08 (2006.01) A61P 39/06 (2006.01) C07D 493/14 (2006.01)

Patent

CA 2748729

Provided are a sulfated C-glycoside which is a novel compound serving as a precursor of chafuroside and chafuroside analogs; a method for efficiently producing the sulfated C--glycoside; and a method for efficiently producing chafuroside and chafuroside analogs using said sulfated C-glycoside. A sulfated C-glycoside represented by general formula (A1) or (B1) [wherein R1, R2 and R3 independently represent each a hydrogen atom or an OH group] is obtained by extracting tea leaves or tea tannins with water, a lower alcohol solvent having 1 to 3 carbon atoms or a liquid mixture comprising the same. Alternatively, the sulfated C-glycoside is produced by reacting a flavone C- glycoside such as isovitexin or vitexin with a sulfate group-introducing agent to thereby sulfate the flavone C-glycoside. By heating the sulfated C-glycoside thus obtained, chafuroside and chafuroside analogs are efficiently produced.

L'invention porte sur un C-glycoside sulfaté qui est un nouveau composé servant de précurseur de chafuroside et d'analogues de chafuroside; sur un procédé pour produire efficacement du C-glycoside sulfaté; et sur un procédé pour produire efficacement du chafuroside et des analogues de chafuroside utilisant ledit C-glycoside sulfaté. Un C-glycoside sulfaté représenté par la formule générale (A1) ou (B1) [dans lesquelles R1, R2 et R3 représentent indépendamment chacun un atome d'hydrogène ou un groupe OH] est obtenu par l'extraction de feuilles de thé ou de tannins de thé avec de l'eau, un solvant alcoolique inférieur ayant 1 à 3 atomes de carbone ou un mélange liquide les comprenant. En variante, le C-glycoside sulfaté est produit par la réaction d'un C-glycoside de flavone tel que l'isovitexine ou la vitexine avec un agent d'introduction de groupe sulfate pour de cette manière sulfater le C-glycoside de flavone. Par chauffage du C-glycoside sulfaté ainsi obtenu, du chafuroside et des analogues de chafuroside sont produits efficacement.

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