Syntheses and Antimicrobial Activity of Tetrasubstituted Tetrahydrofuran Lignan Stereoisomers
Bioscience Biotechnology and Biochemistry2009Vol. 73(7), pp. 1608–1617
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Tomofumi Nakato, Satoshi Yamauchi, Ryosuke Tago, Koichi Akiyama, Masafumi Maruyama, Takuya Sugahara, Taro Kishida, Yojiro Koba
Abstract
The syntheses of all stereoisomers of tetrasubstituted tetrahydrofuran lignan were accomplished, and the antimicrobial activity was examined. The 9,9'-diol compound bearing (7R,7'R,8R,8'R) and (7R,7'S,8R,8'R) stereochemistry showed the strongest antibacterial activity against Listeria denitrificans and Bacillus subtilis, respectively. It was also found that (-)-virgatusin bearing (7S,7'R,8S,8'S) stereochemistry had strongest antifungal activity.
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