JM47, a cyclic tetrapeptide HC-toxin analogue from a marine Fusarium species

Zhong Jiang, Marc Olivier Barret, Kenneth G. Boyd, David R. Adams, A. S F Boyd, J. Grant Burgess

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

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. © 2002 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)33-38
Number of pages6
JournalPhytochemistry
Volume60
Issue number1
DOIs
Publication statusPublished - 10 May 2002

Keywords

  • Codium fragile
  • Enniatin B
  • Fusarium species
  • HC-toxin analogue
  • JM47

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