JM47, a cyclic tetrapeptide HC-toxin analogue from a marine Fusarium species.
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.
Jiang
Zhong
Z
Department of Biological Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK.
Barret
Marc-Olivier
MO
Boyd
Kenneth G
KG
Adams
David R
DR
Boyd
Alan S F
AS
Burgess
J Grant
JG
D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D002855:Chromatography, Thin Layer; D047630:Depsipeptides; D056890:Eukaryota / Q000382:microbiology; D005670:Fusarium / Q000737:chemistry* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D010455:Peptides; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D047630:Depsipeptides; C460541:JM47 peptide; D010455:Peptides; D010456:Peptides, Cyclic; C100264:enniatins