Erabulenols, inhibitors of cholesteryl ester transfer protein produced by Penicillium sp. FO-5637. II. Structure elucidation of erabulenols A and B.
Structures of erabulenols A and B, novel fungal inhibitors of cholesteryl ester transfer protein were elucidated by spectroscopic studies including various NMR measurements. Erabulenols consist of a phenalenone skeleton and a 1,2,2-trimethyltetrahydrofuran moiety in common. Erabulenol B possesses an additional 2,6-dihydroxy-5-methyl-3-methylketonyl benzyl moiety. The absolute stereochemistry at the C-2' position of erabulenol A was deduced as S by comparison of the optical rotation with that of other related compounds.
Tabata
N
N
Research Center for Biological Function, The Kitasato Institute and Graduate School of Pharmaceutical Sciences, Kitasato University, Tokyo, Japan.
Tomoda
H
H
Omura
S
S
D002352:Carrier Proteins / Q000037:antagonists & inhibitors*; D053480:Cholesterol Ester Transfer Proteins; D002788:Cholesterol Esters / Q000378:metabolism*; D004224:Diterpenes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D006023:Glycoproteins; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010407:Penicillium / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D014280:Triglycerides / Q000378:metabolism*; D014315:Triterpenes / Q000737:chemistry*
D002352:Carrier Proteins; D053480:Cholesterol Ester Transfer Proteins; D002788:Cholesterol Esters; D004224:Diterpenes; D005663:Furans; D006023:Glycoproteins; D014280:Triglycerides; D014315:Triterpenes; C114131:erabulenol B; C114130:erabulenol A