New bioactive rosigenin analogues and aromatic polyketide metabolites from the freshwater aquatic fungus Massarina tunicata

Hyuncheol Oh; Dale C Swenson; James B Gloer; Carol A Shearer

doi:10.1021/np020342d

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New bioactive rosigenin analogues and aromatic polyketide metabolites from the freshwater aquatic fungus Massarina tunicata

Journal article

Peer reviewed

New bioactive rosigenin analogues and aromatic polyketide metabolites from the freshwater aquatic fungus Massarina tunicata

Hyuncheol Oh, Dale C Swenson, James B Gloer and Carol A Shearer

Journal of natural products (Washington, D.C.), Vol.66(1), pp.73-79

01/2003

DOI: 10.1021/np020342d

PMID: 12542349

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Abstract

Four new rosigenin analogues (massarigenins A-D; 1-4) and two new aromatic polyketide-derived secondary metabolites (massarinins A and B; 6, 7) and have been isolated from the freshwater aquatic fungus Massarina tunicata. The structures of these compounds were determined primarily by analysis of NMR data, and that of compound 1 was verified by X-ray crystallography. The known compound 4-(2-hydroxybutynoxy)benzoic acid (11) was also obtained, and its absolute stereochemistry was assigned. Several of these metabolites showed antibiotic activity against Gram-positive bacteria.

Ascomycota - chemistry

Aspergillus - drug effects

Bacillus subtilis - drug effects

Candida albicans - drug effects

Crystallography, X-Ray

Furans - chemistry

Fusarium - drug effects

Gram-Negative Bacteria - drug effects

Models, Molecular

Molecular Conformation

Molecular Structure

Nuclear Magnetic Resonance, Biomolecular

Sesquiterpenes - chemistry

Sesquiterpenes - isolation & purification

Sesquiterpenes - pharmacology

Spiro Compounds - chemistry

Staphylococcus aureus - drug effects

Stereoisomerism

Wisconsin

Details

Title: Subtitle: New bioactive rosigenin analogues and aromatic polyketide metabolites from the freshwater aquatic fungus Massarina tunicata
Creators: Hyuncheol Oh - Department of Chemistry, University of Iowa, Iowa City, Iowa 52242, USA
Dale C Swenson
James B Gloer
Carol A Shearer
Resource Type: Journal article
Publication Details: Journal of natural products (Washington, D.C.), Vol.66(1), pp.73-79
DOI: 10.1021/np020342d
PMID: 12542349
ISSN: 0163-3864
eISSN: 1520-6025
Grant note: R01 GM 60600 / NIGMS NIH HHS
Language: English
Date published: 01/2003
Academic Unit: Chemistry
Record Identifier: 9984216719802771

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