Syntheses and Antimicrobial Activity of Tetrasubstituted Tetrahydrofuran Lignan Stereoisomers

Tomofumi NAKATO; Satoshi YAMAUCHI; Ryosuke TAGO; Koichi AKIYAMA; Masafumi MARUYAMA; Takuya SUGAHARA; Taro KISHIDA; Yojiro KOBA

doi:10.1271/bbb.90107

This article has now been updated. Please use the final version.

Syntheses and Antimicrobial Activity of Tetrasubstituted Tetrahydrofuran Lignan Stereoisomers

Tomofumi NAKATO, Satoshi YAMAUCHI, Ryosuke TAGO, Koichi AKIYAMA, Masafumi MARUYAMA, Takuya SUGAHARA, Taro KISHIDA, Yojiro KOBA

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Keywords: lignan, tetrahydrofuran lignan, antimicrobial activity

JOURNAL FREE ACCESS Advance online publication

Article ID: 90107

DOI https://doi.org/10.1271/bbb.90107

The final version of this article is now available: Vol. 73 (2009) , No. 7 p.1608

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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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