Enhanced anti-influenza A virus activity of (-)-epigallocatechin-3-O-gallate fatty acid monoester derivatives: effect of alkyl chain length

Shuichi Mori; Shinya Miyake; Takayoshi Kobe; Takaaki Nakaya; Stephen D Fuller; Nobuo Kato; Kunihiro Kaihatsu

doi:10.1016/j.bmcl.2008.02.020

Enhanced anti-influenza A virus activity of (-)-epigallocatechin-3-O-gallate fatty acid monoester derivatives: effect of alkyl chain length

Bioorg Med Chem Lett. 2008 Jul 15;18(14):4249-52. doi: 10.1016/j.bmcl.2008.02.020. Epub 2008 Feb 10.

Authors

Shuichi Mori¹, Shinya Miyake, Takayoshi Kobe, Takaaki Nakaya, Stephen D Fuller, Nobuo Kato, Kunihiro Kaihatsu

Affiliation

¹ The Institute of Scientific and Industrial Research, Osaka University, 8-1 Mihogaoka, Ibaraki, Osaka 567-0047, Japan.

PMID: 18547804
DOI: 10.1016/j.bmcl.2008.02.020

Abstract

A series of fatty acid monoester derivatives of (-)-epigallocatechin-3-O-gallate (EGCG) were prepared by one-pot lipase-catalyzed transesterification. The introduction of long alkyl chains enhanced anti-influenza A/PR8/34 (H1N1) virus activity 24-fold relative to native EGCG.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antiviral Agents / chemical synthesis*
Antiviral Agents / pharmacology*
Catalysis
Catechin / analogs & derivatives*
Catechin / chemistry
Chemistry, Pharmaceutical / methods
Detergents / chemistry
Dogs
Drug Design
Fatty Acids / chemistry*
Flavonoids / chemistry
Influenza A Virus, H1N1 Subtype / metabolism*
Models, Chemical
Phenols / chemistry
Polyphenols
Solubility
Water / chemistry

Substances

Antiviral Agents
Detergents
Fatty Acids
Flavonoids
Phenols
Polyphenols
Water
Catechin
epigallocatechin gallate