Antimicrobial Activity of Stereoisomers of Butane-Type Lignans

Yuya KAWAGUCHI; Satoshi YAMAUCHI; Kenta MASUDA; Hisashi NISHIWAKI; Koichi AKIYAMA; Masafumi MARUYAMA; Takuya SUGAHARA; Taro KISHIDA; Yojiro KOBA

doi:10.1271/bbb.90167

Organic Chemistry Regular Papers

Antimicrobial Activity of Stereoisomers of Butane-Type Lignans

Yuya KAWAGUCHI, Satoshi YAMAUCHI, Kenta MASUDA, Hisashi NISHIWAKI, Koichi AKIYAMA, Masafumi MARUYAMA, Takuya SUGAHARA, Taro KISHIDA, Yojiro KOBA

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Keywords: lignans, butane-type lignan, antimicrobial activity

JOURNAL FREE ACCESS

2009 Volume 73 Issue 8 Pages 1806-1810

DOI https://doi.org/10.1271/bbb.90167

View "Advance Publication" version (August 7, 2009).

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Abstract

The relationship between the stereochemistry and antimicrobial activity of butane-type lignans was clarified. All stereoisomers of dihydroguaiaretic acid (DGA) showed both antibacterial and antifungal activity. The (+)- and (−)-7,7′-dioxodihydroguaiaretic acid (ODGA) also showed both antibacterial and antifungal activity, while meso-ODGA did not show antibacterial activity, but showed antifungal activity. No activity of any stereoisomer of secoisolariciresinol (SECO) was apparent.

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