title: Antimicrobiological activity of lignan: effect of benzylic oxygen and stereochemistry of 2,3-dibenzyl-4-butanolide and 3,4-dibenzyltetrahydrofuran lignans on activity.
abstract: 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.
authors.affiliation: Integrated Center for Sciences, Ehime University, Matsuyama, Ehime, Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Akiyama
authors.forename: Masafumi
authors.initials: M
authors.lastname: Maruyama
authors.forename: Satoshi
authors.initials: S
authors.lastname: Yamauchi
authors.forename: Yuki
authors.initials: Y
authors.lastname: Nakashima
authors.forename: Tomofumi
authors.initials: T
authors.lastname: Nakato
authors.forename: Ryosuke
authors.initials: R
authors.lastname: Tago
authors.forename: Takuya
authors.initials: T
authors.lastname: Sugahara
authors.forename: Taro
authors.initials: T
authors.lastname: Kishida
authors.forename: Yojiro
authors.initials: Y
authors.lastname: Koba
mesh_terms: D015107:4-Butyrolactone / Q000737:chemistry / Q000494:pharmacology; D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology*; D001412:Bacillus subtilis / Q000187:drug effects; D005663:Furans / Q000737:chemistry / Q000494:pharmacology*; D017705:Lignans / Q000737:chemistry / Q000494:pharmacology*; D008968:Molecular Conformation; D010100:Oxygen / Q000737:chemistry*; D011551:Pseudomonas fluorescens / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship
chemical_list: D000890:Anti-Infective Agents; D005663:Furans; D017705:Lignans; D015107:4-Butyrolactone; D010100:Oxygen