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

• Published in: Phytochemistry (Oxford) 2002-05, Vol.60 (1), p.33-38
• Main Authors: Jiang, Zhong, Barret, Marc-Olivier, Boyd, Kenneth G, Adams, David R, Boyd, Alan S.F, Grant Burgess, J
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Biological and medical sciences; Chemical constitution; Chromatography, Thin Layer; Codium fragile; Depsipeptides; Enniatin B; Eukaryota - microbiology; Fundamental and applied biological sciences. Psychology; Fusarium; Fusarium - chemistry; Fusarium - metabolism; Fusarium species; General pharmacology; HC-toxin analogue; JM47; Magnetic Resonance Spectroscopy; Marine; Medical sciences; Molecular Conformation; Molecular Structure; natural products; Peptides; Peptides, Cyclic - chemistry; Peptides, Cyclic - isolation & purification; Peptides, Cyclic - pharmacology; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant physiology and development
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(02)00061-4

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, (2 S,9 S)-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. JM47, a cyclic tetrapeptide natural product, was isolated from cultures of a marine Fusarium species; its structure was elucidated through NMR studies assisted by molecular modelling.