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Antimicrobiological Activity of Lignan: Effect of Benzylic Oxygen and Stereochemistry of 2,3-Dibenzyl-4-butanolide and 3,4-Dibenzyltetrahydrofuran Lignans on Activity

2007; Oxford University Press; Volume: 71; Issue: 7 Linguagem: Inglês

10.1271/bbb.70168

1347-6947

Koichi Akiyama, Masafumi Maruyama, Satoshi Yamauchi, Yuki Nakashima, Tomofumi Nakato, Ryosuke Tago, Takuya Sugahara, Taro Kishida, Yojiro Koba,

Natural product bioactivities and synthesis

The effect of oxidation degree at the benzylic position of 2,3-dibenzyl-4-butanolide and 3,4-dibenzyltetrahydrofuran lignans on the antimicrobiological activity was examined. The highest oxidation degree at the benzylic position of 2,3-dibenzyl-4-butanolide gave the greatest activity, and 3,4-dibenzoyltetrahydrofuran showed the highest antifungal activity. The relationship between stereochemistry and activity was also examined. Both enantiomers of cis-matairesinol were synthesized for the first time, one of the cis-matairesinols showing antibacterial activity.