Bisabosquals, novel squalene synthase inhibitors. II. Physico-chemical properties and structure elucidation.
The squalene synthase inhibitor bisabosqual A was isolated from the culture broth of Stachybotrys sp. RF-7260, and its structure was determined on the basis of spectroscopic methods including detailed 2D NMR analyses. The structures of bisabosquals B, C and D isolated from Stachybotrys ruwenzoriensis RF-6853 were determined by spectroscopic methods and chemical reactions. The absolute stereochemistry of bisabosquals A, B and D was determined by X-ray crystallographic analysis. They have novel cis-fused tetracyclic structures with a bisabolane-type sesquiterpene and phenol moieties.
Minagawa
K
K
Shionogi Research Laboratories, Shionogi & Co., Ltd., Osaka, Japan. kazuyuki.minagawa@shionogi.co.jp
Kouzuki
S
S
Nomura
K
K
Kawamura
Y
Y
Tani
H
H
Terui
Y
Y
Nakai
H
H
Kamigauchi
T
T
D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000737:chemistry*; D013186:Farnesyl-Diphosphate Farnesyltransferase / Q000037:antagonists & inhibitors*; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D008970:Molecular Weight; D009904:Optical Rotation; D011714:Pyrans / Q000302:isolation & purification* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013191:Stachybotrys / Q000737:chemistry*; D013237:Stereoisomerism
D004791:Enzyme Inhibitors; D011714:Pyrans; D013186:Farnesyl-Diphosphate Farnesyltransferase