JM47, a cyclic tetrapeptide HC-toxin analogue from a marine Fusarium species |
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Authors: | Jiang Zhong Barret Marc-Olivier Boyd Kenneth G Adams David R Boyd Alan S F Burgess J Grant |
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Affiliation: | Department of Biological Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK. |
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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. |
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Keywords: | Fusarium species Codium fragile Enniatin B JM47 HC-toxin analogue |
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