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, A. S F
AU - Grant Burgess, J.
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. © 2002 Elsevier Science Ltd. All rights reserved.
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. © 2002 Elsevier Science Ltd. All rights reserved.
KW - Codium fragile
KW - Enniatin B
KW - Fusarium species
KW - HC-toxin analogue
KW - JM47
UR - http://www.scopus.com/inward/record.url?scp=0037052308&partnerID=8YFLogxK
U2 - 10.1016/S0031-9422(02)00061-4
DO - 10.1016/S0031-9422(02)00061-4
M3 - Article
SN - 0031-9422
VL - 60
SP - 33
EP - 38
JO - Phytochemistry
JF - Phytochemistry
IS - 1
ER -
