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US 8,138,359 B2Granted
Stabilized 3-hydroxyflavan compositions and methods therefor
AssigneeMitsui Norin Co., Ltd.
InventorsYukihiko Hara, Hiroshi Hojo, Slobodan Jovanovic
Life of this patent
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Abstract
Compositions and methods are directed to covalent adducts between reducing agents and optionally substituted 3-hydroxyflavans, wherein the reducing agent is covalently bound to the B-ring of the 3-hydroxyflavan. Such adducts exhibit markedly increased stability towards oxidation as compared to the unmodified 3-hydroxyflavan. Particularly preferred 3-hydroxyflavans include green tea catechins, and especially EGCG, while especially preferred reducing agents include NAC and glutathione.
Claims13
A composition comprising:
- an isolated 3-hydroxyflavan adduct in which a reducing agent, selected from the group consisting of a N-substituted cysteine, glutathione, dithiothreitol, dithioerythrol, mercaptoethanol, and Tris(2-carboxyethyl)phosphine, is covalently bound to a B-ring of the 3-hydroxyflavan, with the proviso that
- (a) where the 3-hydroxyflavan is catechin, then the reducing agent is not glutathione or glutamine-cysteine dipeptide;
- (b) where the 3-hydroxyflavan is epicatechin, then the reducing agent is not dithiothreitol or glutamine-cysteine dipeptide.
A compound having a structure of Formula I
- wherein n is independently between 0 and 3, inclusive;
- R1 is selected from H, OH, an optionally substituted aryl ester, an optionally substituted aryl thioester, and an optionally substituted aryl amide;
- R2 is a reducing agent that is covalently bound via a sulfur atom to the carbon atom of the B-ring;
- wherein the reducing agent is selected from the group consisting of a N-substituted cysteine, glutathione, dithiothreitol, dithioerythrol and mercaptoethanol;
- with the proviso that where R1 is a substituted aryl ester and n is 2 in the A-ring and n is 3 in the B-ring, then R2 is not glutathione;
- with the proviso that where R1 is OH and n is 2, then R2 is not glutathione or glutamine-cysteine dipeptide, or dithiothreitol.
3 more elements
Dependencies are inferred from the claim text.