THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA: II. STRUCTURE ELUCIDATION

Three novel fungal metabolites 1-3 isolated from cultures of a Phoma sp. C2932, are potent and selective inhibitors of squalene synthase. Their structures have been determined by a combination of spectroscopic, X-ray crystallographic and chemical methods; these natural products incorporate the highl...

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Veröffentlicht in:	Journal of antibiotics 1992/05/25, Vol.45(5), pp.648-658
Hauptverfasser:	SIDEBOTTOM, PHILIP J., HIGHCOCK, RONA M., LANE, STEPHEN J., PROCOPIOU, PAN A., WATSON, NIGEL S.
Format:	Artikel
Sprache:	eng
Schlagworte:	Antibiotics (antibacterial agents, antifungal agents) Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents Antifungal Agents - chemistry Antifungal Agents - isolation & purification Antifungal Agents - pharmacology Applied microbiology Biological and medical sciences Bridged Bicyclo Compounds - chemistry Bridged Bicyclo Compounds - isolation & purification Bridged Bicyclo Compounds - pharmacology Bridged Bicyclo Compounds, Heterocyclic Farnesyl-Diphosphate Farnesyltransferase - antagonists & inhibitors Fundamental and applied biological sciences. Psychology Microbiology Phoma Structure-Activity Relationship Tricarboxylic Acids - chemistry Tricarboxylic Acids - isolation & purification Tricarboxylic Acids - pharmacology
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Beschreibung
Zusammenfassung:	Three novel fungal metabolites 1-3 isolated from cultures of a Phoma sp. C2932, are potent and selective inhibitors of squalene synthase. Their structures have been determined by a combination of spectroscopic, X-ray crystallographic and chemical methods; these natural products incorporate the highly functionalised bicyclic core, [1S-(1α, 3α, 4β, 5α, 6α, 7β)]-4, 6, 7-trihydroxy-2, 8-dioxabicyclo[3.2.l]octane-3, 4, 5-tricarboxylic acid.
ISSN:	0021-8820 1881-1469
DOI:	10.7164/antibiotics.45.648