Stabilized 3-hydroxyflavan compositions and methods therefor
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07D-311/62
C07F-009/50
출원번호
US-0996933
(2005-07-26)
등록번호
US-8138359
(2012-03-20)
국제출원번호
PCT/US2005/026521
(2005-07-26)
§371/§102 date
20080721
(20080721)
국제공개번호
WO2007/018502
(2007-02-15)
발명자
/ 주소
Hara, Yukihiko
Hojo, Hiroshi
Jovanovic, Slobodan
출원인 / 주소
Mitsui Norin Co., Ltd.
대리인 / 주소
Fish & Associates, PC
인용정보
피인용 횟수 :
0인용 특허 :
1
초록▼
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 u
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.
대표청구항▼
1. 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-hydroxy
1. 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. 2. The composition of claim 1 wherein the reducing agent is covalently bound via a sulfur atom to a carbon atom of the B-ring. 3. The composition of claim 1 wherein the reducing agent is a nutritionally acceptable reducing agent. 4. The composition of claim 1 wherein the 3-hydroxyflavan is selected from the group consisting of (−)-Epigallocatechin gallate, (−)-Gallocatechin gallate, (+)-Epigallocatechin gallate, (+)-Gallocatechin gallate, (−)-Epigallocatechin, (−)-Gallocatechin, (+)-Epigallocatechin, (+)-Gallocatechin, (−)-Epicatechin gallate, (−)-Catechin gallate, (+)-Epicatechin gallate, (+)-Catechin gallate, (−)-Epicatechin, (−)-Catechin, (+)-Epicatechin, and (+)-Catechin. 5. The composition of claim 1 wherein the 3-hydroxyflavan is selected from the group consisting of (−)-Epigallocatechin gallate, (−)-Gallocatechin gallate, (+)-Epigallocatechin gallate, (+)-Gallocatechin gallate, (−)-Epigallocatechin, (−)-Gallocatechin, (+)-Epigallocatechin, and (+)-Gallocatechin. 6. The composition of claim 1 wherein the 3-hydroxyflavan is selected from the group consisting of (−)-Epigallocatechin gallate, (−)-Gallocatechin gallate, (+)-Epigallocatechin gallate and (+)-Gallocatechin gallate. 7. The composition of claim 1 having a pH between 4.0 and 6.0, inclusive. 8. The composition of claim 1 wherein the reducing agent is selected from the group consisting of glutathione and N-acetyl cysteine. 9. 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. 10. The compound of claim 9 wherein the reducing agent is a nutritionally acceptable reducing agent. 11. The compound of claim 9 wherein R1 has a structure according to Formula II wherein n is between 0 and 3, inclusive. 12. The compound of claim 9 wherein R2 has a structure according to Formula III wherein R3, R4, and R5 are independently selected from the group consisting of H, acyl, acetyl, alkyl, aryl, each of which may be substituted wherein one or both of R3 and R4 other than H, and wherein m is 1. 13. The compound of claim 9 wherein n is independently between 2 and 3, inclusive, R1 is a gallic acid radical, and R2 is a glutathione radical or an N-acetyl cysteine radical.
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