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Aldehyde conjugated flavonoid preparations

A technology of flavonoids and flavonoids, which is applied in the field of flavonoid oligomers, can solve the problems of difficult compound delivery and impossible utilization of beneficial physiological activities

Inactive Publication Date: 2008-05-14
AGENCY FOR SCI TECH & RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, flavonoids may be expected to remain only in the digestive tract, and thus their beneficial physiological activity may not be available to other tissues
Also, their strong hydrophobicity and their tendency to form complexes with proteins make delivery of these compounds difficult

Method used

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  • Aldehyde conjugated flavonoid preparations
  • Aldehyde conjugated flavonoid preparations
  • Aldehyde conjugated flavonoid preparations

Examples

Experimental program
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Effect test

Embodiment 1

[0096] Example 1: Conjugation of polyethylene glycol with (-)-epigalcatechin gallate or with oligomeric (-)-epigalcatechin gallate

[0097] In this study, the inventors synthesized conjugates of poly(ethylene glycol) (PEG) with (-)-epicatechin gallate (EGCG) or oligomeric EGCG (OEGCG). PEG-EGCG or PEG-OEGCG conjugation utilizing aldehyde-terminated PEG (PEG-CHO) proceeds via Baeyer acid-catalyzed condensation between the aldehyde moiety at the end of the PEG chain and the nucleophilic phloroglucinol ring of the EGCG moiety (Fig. 1).

[0098] Materials: (-)-Epicatechin gallate (EGCG) was purchased from KURITA LTD., Japan. Aldehyde terminated polyethylene glycol (PEG-CHO) was purchased from NOF Co., Japan. Acetic acid, acetaldehyde, PURPALD TM , Folin-Ciocalteau phenolic reagent, sodium carbonate, vanillin and dimethylsulfoxide-d 6 Available from Sigma-Aldrich. 1N sodium hydroxide was purchased from Wako Pure Chemical Industries, Japan. Other reagents and solvents were com...

Embodiment 2

Embodiment 3

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Abstract

The invention provides a method of conjugating a polymer containing a free aldehyde group with a flavonoid in the presence of an acid catalyst, such that the polymer is conjugated to the C6 or C8 position of the flavonoid A ring. The resulting conjugates may be used to form delivery vehicles to deliver high doses of flavonoids, and may also be used as delivery vehicles to deliver an additional bioactive agent.

Description

[0001] Cross References to Related Applications [0001] This application claims the benefit of and priority from US Provisional Patent Application No. 60 / 682,801, filed May 20, 2005, the contents of which are hereby incorporated by reference. field of invention [0002] The present invention relates generally to formulations of flavonoids, and in particular to delivery agent-bound flavonoids and / or delivery agent-bound flavonoid oligomers. Background of the invention [0003] Flavonoids are one of the most diverse and well-studied classes of plant polyphenols. Flavonoids consist of a large class of low molecular weight polyphenolic substances that occur naturally in fruits and vegetables and are an integral part of the human diet. Dried green tea leaves can contain as much as 30% by weight flavonoids, including high percentages of flavonoids known as catechins (flavan-3-ol derivatives or catechin-based flavonoids), including (- )-epicatechin, (-)-epigallocatechin, (+)-cat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A61K47/48A61K31/353C08G65/331
CPCA61K47/488C08G65/331A61K47/48284A61K47/48215C08B37/0072A61K47/60A61K47/643A61K47/6907
Inventor 卓朗郑株润栗泽元一杨仪岩
Owner AGENCY FOR SCI TECH & RES
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