Antifungal activity of tetra-substituted tetrahydrofuran lignan, (-)-virgatusin, and its structure-activity relationship.
Antifungal activities of the optically pure (>99%ee) (-)- and (+)-virgatusin, a tetra-substituted tetrahydrofuran lignan, were tested. (-)-Virgatusin, which is a natural product, showed highest antifungal activity against Colletotrichum lagenarium. Research on its structure-activity relationship was also performed. It was shown that two methoxy groups on 9 and 9' positions and a 3,4-methylenedioxyphenyl group on the 7 position of virgatusin were essential for high fungal growth inhibition. The part on 7'-phenyl group was not essential for activity. The 7'-(4-methoxyphenyl) derivative showed higher activity than that of (-)-virgatusin.
Akiyama
Koichi
K
Integrated Center for Sciences, Tarumi Station, Ehime University, Matsuyama, Ehime, Japan.
Yamauchi
Satoshi
S
Nakato
Tomofumi
T
Maruyama
Masafumi
M
Sugahara
Takuya
T
Kishida
Taro
T
D000935:Antifungal Agents / Q000494:pharmacology*; D002392:Catechin / Q000494:pharmacology; D004121:Dimethyl Sulfoxide / Q000494:pharmacology; D005419:Flavonoids / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects*; D005663:Furans / Q000494:pharmacology*; D007202:Indicators and Reagents; D017705:Lignans / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D010636:Phenols / Q000494:pharmacology; D059808:Polyphenols; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000935:Antifungal Agents; D005419:Flavonoids; D005663:Furans; D007202:Indicators and Reagents; D017705:Lignans; D010636:Phenols; D059808:Polyphenols; C511226:virgatusin; D002392:Catechin; D004121:Dimethyl Sulfoxide