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 ruwenzoriensi...

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Bibliographic Details
Published in:Journal of antibiotics 2001/11/25, Vol.54(11), pp.896-903
Main Authors: MINAGAWA, KAZUYUKI, KOUZUKI, SHUICHI, NOMURA, KAZUHIDE, KAWAMURA, YOSHIMI, TANI, HIROYOSHI, TERUI, YOSHIHIRO, NAKAI, HIROSHI, KAMIGAUCHI, TOSHIYUKI
Format: Article
Language:English
Subjects:
Antibiotics (antibacterial agents, antifungal agents)
Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents
Applied microbiology
Biological and medical sciences
Crystallography, X-Ray
Enzyme Inhibitors - chemistry
Farnesyl-Diphosphate Farnesyltransferase - antagonists & inhibitors
Fundamental and applied biological sciences. Psychology
Gas Chromatography-Mass Spectrometry
Magnetic Resonance Spectroscopy
Microbiology
Molecular Weight
Optical Rotation
Pyrans - isolation & purification
Pyrans - pharmacology
Spectrophotometry, Infrared
Spectrophotometry, Ultraviolet
Stachybotrys - chemistry
Stereoisomerism
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Summary: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.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.54.896