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

被引:101
作者
Mori, Shuichi [1 ]
Miyake, Shinya [1 ]
Kobe, Takayoshi [1 ]
Nakaya, Takaaki [2 ]
Fuller, Stephen D. [3 ]
Kato, Nobuo [1 ]
Kaihatsu, Kunihiro [1 ]
机构
[1] Osaka Univ, Inst Sci & Ind Res, Osaka 5670047, Japan
[2] Osaka Univ, Microbial Dis Res Inst, Suita, Osaka 5650871, Japan
[3] Univ Oxford, Wellcome Trust Ctr Human Genet, Div Struct Biol, Oxford OX3 7BN, England
关键词
epigallocatechin gallate; influenza virus; lipase-catalyzed esterification; antivirus agent;
D O I
10.1016/j.bmcl.2008.02.020
中图分类号
R914 [药物化学];
学科分类号
100701 [药物化学];
摘要
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. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4249 / 4252
页数:4
相关论文
共 18 条
[1]
A major constituent of green tea, EGCG, inhibits the growth of a human cervical cancer cell line, CaSki cells, through apoptosis, G1 arrest, and regulation of gene expression [J].
Ahn, WS ;
Huh, SW ;
Bae, SM ;
Lee, IP ;
Lee, JM ;
Namkoong, SE ;
Kim, CK ;
Sin, JI .
DNA AND CELL BIOLOGY, 2003, 22 (03) :217-224
[2]
Green tea and tea polyphenols in cancer prevention [J].
Chen, D ;
Daniel, KG ;
Kuhn, DJ ;
Kazi, A ;
Bhuiyan, M ;
Li, LH ;
Wang, ZG ;
Wan, SB ;
Lam, WH ;
Chan, TH ;
Dou, QP .
FRONTIERS IN BIOSCIENCE-LANDMARK, 2004, 9 :2618-2631
[3]
Concise synthesis of dideoxy-epigallocatechin gallate (DO-EGCG) and evaluation of its anti-influenza virus activity [J].
Furuta, Takumi ;
Hirooka, Yasuo ;
Abe, Ayako ;
Sugata, Yusuke ;
Ueda, Mitsuru ;
Murakami, Kouki ;
Suzuki, Takashi ;
Tanaka, Kiyoshi ;
Kan, Toshiyuki .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (11) :3095-3098
[4]
Hong J, 2002, CANCER RES, V62, P7241
[5]
Tea catechins with a galloyl moiety suppress postprandial hypertriacylglycerolemia by delaying lymphatic transport of dietary fat in rats [J].
Ikeda, I ;
Tsuda, K ;
Suzuki, Y ;
Kobayashi, M ;
Unno, T ;
Tomoyori, H ;
Goto, H ;
Kawata, Y ;
Imaizumi, K ;
Nozawa, A ;
Kakuda, T .
JOURNAL OF NUTRITION, 2005, 135 (02) :155-159
[6]
Additional inhibitory effect of tea extract on the growth of influenza A and B viruses in MDCK cells [J].
Imanishi, N ;
Tuji, Y ;
Katada, Y ;
Maruhashi, M ;
Konosu, S ;
Mantani, N ;
Terasawa, K ;
Ochiai, H .
MICROBIOLOGY AND IMMUNOLOGY, 2002, 46 (07) :491-494
[7]
Green tea extract (AR25®) inhibits lipolysis of triglycerides in gastric and duodenal medium in vitro [J].
Juhel, C ;
Armand, M ;
Pafumi, Y ;
Rosier, C ;
Vandermander, J ;
Lairon, D .
JOURNAL OF NUTRITIONAL BIOCHEMISTRY, 2000, 11 (01) :45-51
[8]
KAIHATSU K, 2006, Patent No. 304788
[9]
Identification of biliary metabolites of (-)-epigallocatechin gallate in rats [J].
Kida, K ;
Suzuki, M ;
Matsumoto, N ;
Nanjo, F ;
Hara, Y .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2000, 48 (09) :4151-4155
[10]
Synthesis of (-)-[4-3H]epigallocatechin gallate and its metabolic fate in rats after intravenous administration [J].
Kohri, T ;
Nanjo, F ;
Suziki, M ;
Seto, R ;
Matsumoto, N ;
Yamakawa, M ;
Hojo, H ;
Hara, Y ;
Desai, D ;
Amin, S ;
Conaway, CC ;
Chung, FL .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2001, 49 (02) :1042-1048