189185-67-9Relevant academic research and scientific papers
Stachyflin and acetylstachyflin, novel anti-influenza A virus substances, produced by Stachybotrys sp. RF-7260. I. Isolation, structure elucidation and biological activities
Minagawa, Kazuyuki,Kouzuki, Shuichi,Yoshimoto, Jun,Kawamura, Yoshimi,Tani, Hiroyoshi,Iwata, Tatsuo,Terui, Yoshihiro,Nakai, Hiroshi,Yagi, Shigenori,Hattori, Naohiko,Fujiwara, Tamio,Kamigauchi, Toshiyuki
, p. 155 - 164 (2002)
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 μM. Acetylstachyflin was about 77-fold less active than stachyflin.
Stachyflin and acetylstachyflin, novel anti-influenza A virus substances, produced by Stachybotrys sp. RF-7260. II. Synthesis and preliminary structure-activity relationships of stachyflin derivatives
Minagawa, Kazuyuki,Kouzuki, Shuichi,Kamigauchi, Toshiyuki
, p. 165 - 171 (2007/10/03)
Stachyflin and acetylstachyflin, produced by Stachybotrys sp. RF-7260, were found to have potent anti-influenza A virus activity. Stachyflin is a new class of hemagglutinin fusion inhibitors of influenza A virus. Several derivatives were synthesized from acetylstachyflin and subjected to preliminary examination of their structure-activity relationships. Among them, the 3-oxo and 3,8′-dioxo derivatives showed potent antiviral activity similar to stachyflin. The 3-epi derivative was four times less active than stachyflin. Modification of the 6′-hydroxy group and the C-5′ position markedly diminished the antiviral activity.
