Synthesis and antimicrobial activities of 3-O-alkyl analogues of (+)-catechin: Improvement of stability and proposed action mechanism

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Title
Synthesis and antimicrobial activities of 3-O-alkyl analogues of (+)-catechin: Improvement of stability and proposed action mechanism
Author(s)
Ki Duk Park; S J Cho
Bibliographic Citation
European Journal of Medicinal Chemistry, vol. 45, no. 3, pp. 1028-1033
Publication Year
2010
Abstract
We report here the synthesis and biological properties of 3-O-alkyl analogues of (+)-catechin (5), which itself is one of the major natural polyphenols found in green tea and has several physiological activities. Starting from 5, a series of 3-O-alkyl-(+)-catechin derivatives were investigated as potent antimicrobial agents. The presence of an alkyl chain rather than acyl on 3-O- showed an increase in antimicrobial activity which may be due to stability in standard culture condition. The most promising compound is 8e, 3-O-decyl analogue, with the MIC of 0.5-2, 32-128 and 2-4 μg/mL against Gram-positive bacteria, Gram-negative bacteria and human pathogenic fungi, respectively. Regarding action mechanism, the antimicrobial activity is possibly due to the lipophilicity and disrupting ability of the analogues to the liposome membrane.
Keyword
3-O-acyl-(+)-catechins3-O-Alkyl-(+)-catechinsAntimicrobial activity
ISSN
0223-5234
Publisher
Elsevier
DOI
http://dx.doi.org/10.1016/j.ejmech.2009.11.045
Type
Article
Appears in Collections:
1. Journal Articles > Journal Articles
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