Antimicrobiological activity of lignan: Effect of benzylic oxygen and stereochemistry of 2,3-dibenzyl-4-butanolide and 3,4-dibenzyltetrahydrofuran lignans on activity

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-dibenz...

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Veröffentlicht in:	Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2007-07, Vol.71 (7), p.1745-1751
Hauptverfasser:	Akiyama, K.(Ehime Univ., Matsuyama (Japan). Faculty of Agriculture), Maruyama, M, Yamauchi, S, Nakashima, Y, Nakato, T, Tago, R, Sugahara, T, Kishida, T, Koba, Y
Format:	Artikel
Sprache:	eng
Schlagworte:	4-Butyrolactone - chemistry 4-Butyrolactone - pharmacology Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology ANTIMICROBIAL PROPERTIES antimicrobiological activity Bacillus subtilis - drug effects Biological and medical sciences Fundamental and applied biological sciences. Psychology Furans - chemistry Furans - pharmacology LIGNANAS LIGNANE LIGNANS Lignans - chemistry Lignans - pharmacology MICRO-ORGANISME MICROORGANISMOS MICROORGANISMS Molecular Conformation OXIDACION OXIDATION OXYDATION Oxygen - chemistry PROPIEDADES ANTIMICROBIANAS PROPRIETE ANTIMICROBIENNE Pseudomonas fluorescens - drug effects Staphylococcus aureus - drug effects Structure-Activity Relationship tetrahydrofuran lignan γ-butyrolactone lignan
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Zusammenfassung:	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.
ISSN:	0916-8451 1347-6947
DOI:	10.1271/bbb.70168