Hypocoprins A-C: new sesquiterpenoids from the coprophilous fungus Hypocopra rostrata

Dinith R Jayanetti; Qun Yue; Gerald F Bills; James B Gloer

doi:10.1021/np5007718

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Hypocoprins A-C: new sesquiterpenoids from the coprophilous fungus Hypocopra rostrata

Journal article

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Hypocoprins A-C: new sesquiterpenoids from the coprophilous fungus Hypocopra rostrata

Dinith R Jayanetti, Qun Yue, Gerald F Bills and James B Gloer

Journal of natural products (Washington, D.C.), Vol.78(3), pp.396-401

03/27/2015

DOI: 10.1021/np5007718

PMCID: PMC4380195

PMID: 25549014

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Abstract

Studies of the coprophilous fungus Hypocopra rostrata (TTI-0009, NRRL 66178) isolated from a sample of horse dung collected in Texas led to the isolation of three new sesquiterpenoids that we named hypocoprins A-C (1-3), together with the known fungal metabolite helvolic acid. The new metabolites have a distinctive ring system consisting of fused cyclopropane and cyclodecene units not previously reported from a fungal source. Compounds 1 and 3 moderately inhibited growth of Staphylococcus aureus. The structures of these metabolites were assigned mainly by analysis of 2D NMR and HRESITOFMS data. Relative and absolute configurations were assigned by interpretation of NMR J-values and NOESY data and by application of Mosher's method. These results represent the first report of chemistry from any strain of the genus Hypocopra.

Antifungal Agents - pharmacology

Fusidic Acid - isolation & purification

Sesquiterpenes - isolation & purification

Sesquiterpenes - chemistry

Animals

Texas

Horses

Nuclear Magnetic Resonance, Biomolecular

Fusidic Acid - analogs & derivatives

Manure - microbiology

Molecular Structure

Staphylococcus aureus - drug effects

Xylariales - chemistry

Details

Title: Subtitle: Hypocoprins A-C: new sesquiterpenoids from the coprophilous fungus Hypocopra rostrata
Creators: Dinith R Jayanetti - †Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
Qun Yue - ‡Texas Therapeutics Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston, 1881 East Road, Houston, Texas 77054, United States
Gerald F Bills - ‡Texas Therapeutics Institute, The Brown Foundation Institute of Molecular Medicine, University of Texas Health Science Center at Houston, 1881 East Road, Houston, Texas 77054, United States
James B Gloer - †Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, United States
Resource Type: Journal article
Publication Details: Journal of natural products (Washington, D.C.), Vol.78(3), pp.396-401
Publisher: United States
DOI: 10.1021/np5007718
PMID: 25549014
PMCID: PMC4380195
ISSN: 0163-3864
eISSN: 1520-6025
Grant note: S10 RR025500 / NCRR NIH HHS
Language: English
Date published: 03/27/2015
Academic Unit: Chemistry
Record Identifier: 9983985850902771

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