Document Detail


JM47, a cyclic tetrapeptide HC-toxin analogue from a marine Fusarium species.
MedLine Citation:
PMID:  11985849     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Zhong Jiang; Marc-Olivier Barret; Kenneth G Boyd; David R Adams; Alan S F Boyd; J Grant Burgess
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Phytochemistry     Volume:  60     ISSN:  0031-9422     ISO Abbreviation:  Phytochemistry     Publication Date:  2002 May 
Date Detail:
Created Date:  2002-05-02     Completed Date:  2002-07-26     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0151434     Medline TA:  Phytochemistry     Country:  United States    
Other Details:
Languages:  eng     Pagination:  33-8     Citation Subset:  IM    
Affiliation:
Department of Biological Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK.
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MeSH Terms
Descriptor/Qualifier:
Algae / 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:
0/Anti-Bacterial Agents; 0/Depsipeptides; 0/JM47 peptide; 0/Peptides; 0/Peptides, Cyclic; 0/enniatins

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