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-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.
Akiyama
Koichi
K
Integrated Center for Sciences, Ehime University, Matsuyama, Ehime, Japan.
Maruyama
Masafumi
M
Yamauchi
Satoshi
S
Nakashima
Yuki
Y
Nakato
Tomofumi
T
Tago
Ryosuke
R
Sugahara
Takuya
T
Kishida
Taro
T
Koba
Yojiro
Y
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
D000890:Anti-Infective Agents; D005663:Furans; D017705:Lignans; D015107:4-Butyrolactone; D010100:Oxygen