Stachyflin and acetylstachyflin, novel anti-influenza A virus substances, produced by Stachybotrys sp. RF-7260. I. Isolation, structure elucidation and biological activities.
Two novel compounds, stachyflin and acetylstachyflin, have been isolated by solid-state fermentation of Stachybotrys sp. RF-7260. The structures of both metabolites, determined by detailed NMR analyses and X-ray crystallographic analysis, are novel with a pentacyclic moiety including cis-fused decalin. The absolute stereochemistry of stachyflins was determined by circular dichroism analysis. Stachyflin showed antiviral activity against influenza A virus (H1N1) in vitro with an IC50 value of 0.003 microM. Acetylstachyflin was about 77-fold less active than stachyflin.
Minagawa
Kazuyuki
K
Shionogi Research Laboratories, Shionogi & Co, Ltd, Osaka, Japan. kazuyuki.minagawa@shionogi.co.jp
Kouzuki
Shuichi
S
Yoshimoto
Jun
J
Kawamura
Yoshimi
Y
Tani
Hiroyoshi
H
Iwata
Tatsuo
T
Terui
Yoshihiro
Y
Nakai
Hiroshi
H
Yagi
Shigenori
S
Hattori
Naohiko
N
Fujiwara
Tamio
T
Kamigauchi
Toshiyuki
T
D000998:Antiviral Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D005285:Fermentation; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009980:Influenza A virus / Q000187:drug effects; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D006576:Heterocyclic Compounds, 4 or More Rings; D007211:Indoles; D012717:Sesquiterpenes; C455263:acetylstachyflin; C120519:stachyflin