The unexpected isolation of CTP-431, a novel thiopyrone from the sponge Cacospongia mycofijiensis.
A reinvestigation of a Fijian collection of Cacospongia mycofijiensis has yielded the known mycothiazole and a novel heterocyclic, CTP-431 (1). Its structure including absolute configuration as 8R,9R,10S,13S was established using NMR data, calculated DFT (13)C chemical shifts and results from X-ray crystallography. It is possible that the tricyclic skeleton of CTP-431 (1) is biosynthetically related to the macrolide latrunculin A, however the thiopyrone moiety of 1 has no previous precedent in natural products chemistry.
Johnson
Tyler A
TA
Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA.
Amagata
Taro
T
Oliver
Allen G
AG
Tenney
Karen
K
Valeriote
Frederick A
FA
Crews
Phillip
P
D000818:Animals; D018360:Crystallography, X-Ray; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008956:Models, Chemical; D008958:Models, Molecular; D008968:Molecular Conformation; D011161:Porifera / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification*; D012015:Reference Standards
C532726:CTP-431; D011753:Pyrones