Syntheses and antimicrobial activity of tetrasubstituted tetrahydrofuran lignan stereoisomers.
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.
Nakato
Tomofumi
T
Faculty of Agriculture, Ehime University, Matsuyama, Ehime, Japan.
Yamauchi
Satoshi
S
Tago
Ryosuke
R
Akiyama
Koichi
K
Maruyama
Masafumi
M
Sugahara
Takuya
T
Kishida
Taro
T
Koba
Yojiro
Y
D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D005663:Furans / Q000737:chemistry*; D017705:Lignans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000890:Anti-Infective Agents; D005663:Furans; D017705:Lignans