Relationship between Antibacterial Activity of (+)-Catechin Derivatives and Their Interaction with a Model Membrane
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- 作者：Katsuko Kajiya ; Hiroshi Hojo ; Masayuki Suzuki ; Fumio Nanjo ; Shigenori Kumazawa ; and Tsutomu Nakayama
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2004
- 出版时间：March 24, 2004
- 年：2004
- 卷：52
- 期：6
- 页码：1514 - 1519
- 全文大小：124K
- 年卷期：v.52,no.6(March 24, 2004)
- ISSN：1520-5118
文摘
(+)-Catechin derivatives with different alkyl chain lengths were synthesized from (+)-catechin andvarious straight chain alkylaldehydes in the presence of methyl mercaptan, and their antibacterialactivities against Gram-positive bacteria were evaluated. The antibacterial activity increased markedlywith elongation of the alkyl chain lengths of the derivatives and reached a maximum at a chain offour to seven carbons. Subsequently, interaction of the (+)-catechin derivatives with a modelmembrane using liposome was investigated. The derivatives with a chain of three carbons or morewere found to have very strong affinity for the membrane. The injury action of the derivatives againstthe membrane was examined with liposome in which calcein was enclosed as a fluorescent indicator.The leakage was observed in the derivatives with chain lengths of four carbons or more. Particularlythe derivatives with chains longer than five carbons are considered to destroy the liposome membranejudging from the degree of the fluorescent leakage. These results implied that the lipophilicity anddisrupting ability of the (+)-catechin derivatives to the liposome membrane participate in theirantibacterial activity.Keywords: Antibacterial activity; (+)-catechin derivative; lipid bilayer; liposome