title: Synthesis and antimicrobial activities of 3-O-alkyl analogues of (+)-catechin: improvement of stability and proposed action mechanism.
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 microg/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.
authors: Laboratory of Cellular Function Modulator, Korea Research Institute of Bioscience and Biotechnology, Yuseong, Daejeon 305-806, Republic of Korea. kdpark@email.unc.edu
authors: Ki Duk
authors: KD
authors: Park
authors: Sung Jin
authors: SJ
authors: Cho
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects*; D028241:Camellia sinensis / Q000737:chemistry; D002392:Catechin / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015195:Drug Design; D004355:Drug Stability; D005658:Fungi / Q000187:drug effects*; D006801:Humans; D006863:Hydrogen-Ion Concentration; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D013662:Tea / Q000737:chemistry
chemical_list: D000890:Anti-Infective Agents; D013662:Tea; D002392:Catechin