| JM47, a cyclic tetrapeptide HC-toxin analogue from a marine Fusarium species. | |
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MedLine Citation:
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PMID: 11985849 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The known metabolite, enniatin B, and a cyclic tetrapeptide, JM47, which is a new natural product, were extracted from brown rice cultures of a marine fungus, identified as a Fusarium species, isolated from the marine alga Codium fragile. NMR studies, including 15N HMQC and 15N HMBC, established the structure of JM47 as cyclo(Ala-Ala-Aoh-Pro), where Aoh is the amino acid, (2S,9S)-2-amino-8-oxo-9-hydroxydecanoic acid. The absolute stereochemistry of the Aoh side chain carbinol centre was determined using Mosher ester methodology. Analysis of NOESY data assisted by molecular modelling revealed an alternating L-, D-, L-, D-configuration for the tetrapeptide core. The absolute stereochemistry of the core was determined by acidic hydrolysis and chiral TLC analysis of the proline residue. JM47 belongs to the HC-toxin family of cyclic tetrapeptides which possess a 2-amino-8-oxo-9,10-epoxydecanoic acid residue in place of the Aoh unit. This is the first report of an analogue of HC-toxin from a marine Fusarium species. |
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Authors:
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Zhong Jiang; Marc-Olivier Barret; Kenneth G Boyd; David R Adams; Alan S F Boyd; J Grant Burgess |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Phytochemistry Volume: 60 ISSN: 0031-9422 ISO Abbreviation: Phytochemistry Publication Date: 2002 May |
Date Detail:
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Created Date: 2002-05-02 Completed Date: 2002-07-26 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0151434 Medline TA: Phytochemistry Country: United States |
Other Details:
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Languages: eng Pagination: 33-8 Citation Subset: IM |
Affiliation:
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Department of Biological Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Algae
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microbiology Anti-Bacterial Agents / chemistry*, isolation & purification*, pharmacology Chromatography, Thin Layer Depsipeptides* Fusarium / chemistry*, metabolism Magnetic Resonance Spectroscopy Molecular Conformation Molecular Structure Peptides* Peptides, Cyclic / chemistry*, isolation & purification*, pharmacology |
| Chemical | |
Reg. No./Substance:
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0/Anti-Bacterial Agents; 0/Depsipeptides; 0/JM47 peptide; 0/Peptides; 0/Peptides, Cyclic; 0/enniatins |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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