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 decal...

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Bibliographic Details
Published in:Journal of antibiotics 2002/02/25, Vol.55(2), pp.155-164
Main Authors: MINAGAWA, KAZUYUKI, KOUZUKI, SHUICHI, YOSHIMOTO, JUN, KAWAMURA, YOSHIMI, TANI, HIROYOSHI, IWATA, TATSUO, TERUI, YOSHIHIRO, NAKAI, HIROSHI, YAGI, SHIGENORI, HATTORI, NAOHIKO, FUJIWARA, TAMIO, KAMIGAUCHI, TOSHIYUKI
Format: Article
Language:English
Subjects:
Antibiotics. Antiinfectious agents. Antiparasitic agents
Antiviral agents
Antiviral Agents - chemistry
Antiviral Agents - isolation & purification
Antiviral Agents - pharmacology
Biological and medical sciences
Fermentation
Heterocyclic Compounds, 4 or More Rings - chemistry
Heterocyclic Compounds, 4 or More Rings - isolation & purification
Heterocyclic Compounds, 4 or More Rings - pharmacology
Indoles - chemistry
Indoles - isolation & purification
Indoles - pharmacology
Influenza A virus - drug effects
Medical sciences
Molecular Structure
Pharmacology. Drug treatments
Sesquiterpenes - chemistry
Sesquiterpenes - isolation & purification
Sesquiterpenes - pharmacology
Structure-Activity Relationship
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Description
Summary: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 0.003μM. Acetylstachyflin was about 77-fold less active than stachyflin.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.55.155