TY - JOUR
T1 - JM47, a cyclic tetrapeptide HC-toxin analogue from a marine Fusarium species
AU - Jiang, Zhong
AU - Barret, Marc Olivier
AU - Boyd, Kenneth G.
AU - Adams, David R.
AU - Boyd, Alan S.F.
AU - Grant Burgess, J.
N1 - Funding Information:
The authors thank the Scottish Hospital Endowments Research Trust (RG9/99) for financial support, Dr. R. Ferguson for acquisition of the mass spectra and Mrs. C. Graham for determination of the specific optical rotation. We also thank Professor S. Amyes (Department of Medical Microbiology, University of Edinburgh) for test strains.
Copyright:
Copyright 2008 Elsevier B.V., All rights reserved.
PY - 2002/5/10
Y1 - 2002/5/10
N2 - 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.
AB - 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.
KW - Codium fragile
KW - Enniatin B
KW - Fusarium species
KW - HC-toxin analogue
KW - JM47
UR - https://www.scopus.com/pages/publications/0037052308
UR - https://www.scopus.com/pages/publications/0037052308#tab=citedBy
U2 - 10.1016/S0031-9422(02)00061-4
DO - 10.1016/S0031-9422(02)00061-4
M3 - Article
C2 - 11985849
AN - SCOPUS:0037052308
SN - 0031-9422
VL - 60
SP - 33
EP - 38
JO - Phytochemistry
JF - Phytochemistry
IS - 1
ER -