Structure elucidation of roselipins, inhibitors of diacylglycerol acyltransferase produced by Gliocladium roseum KF-1040.
The structures of roselipins 1A, 1B, 2A and 2B were elucidated by spectroscopic studies including 1H-1H COSY, 13C-1H COSY, 13C-1H HMQC and 13C-1H HMBC NMR experiments, and degradation experiments. They have the common skeleton of 2,4,6,8,10,12,14,16,18-nonamethyl-5,9,13-trihydroxy-2E,6E, 10E-icosenoic acid modified with a D-mannose and a D-arabinitol. Roselipin A and B groups were stereoisomers at the arabinitol moiety, which esterified the fatty acid from the different terminal hydroxy residue. Roselipin 2 group was 6"-O-acetyl roselipin 1 group.
Tabata
N
N
Research Center for Biological Function, The Kitasato Institute and Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
Ohyama
Y
Y
Tomoda
H
H
Abe
T
T
Namikoshi
M
M
Omura
S
S
D000217:Acyltransferases / Q000037:antagonists & inhibitors*; D051048:Diacylglycerol O-Acyltransferase; D004791:Enzyme Inhibitors / Q000737:chemistry*; D005227:Fatty Acids / Q000737:chemistry*; D003904:Mitosporic Fungi / Q000378:metabolism*; D008968:Molecular Conformation; D009005:Monosaccharides / Q000737:chemistry*
D004791:Enzyme Inhibitors; D005227:Fatty Acids; D009005:Monosaccharides; C401212:roselipin 1A; C401213:roselipin 2A; D000217:Acyltransferases; D051048:Diacylglycerol O-Acyltransferase