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

PHILIP J. SIDEBOTTOM; RONA M. HIGHCOCK; STEPHEN J. LANE; PAN A. PROCOPIOU; NIGEL S. WATSON

doi:10.7164/antibiotics.45.648

The Journal of Antibiotics

Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820

THE SQUALESTATINS, NOVEL INHIBITORS OF SQUALENE SYNTHASE PRODUCED BY A SPECIES OF PHOMA

II. STRUCTURE ELUCIDATION

PHILIP J. SIDEBOTTOM, RONA M. HIGHCOCK, STEPHEN J. LANE, PAN A. PROCOPIOU, NIGEL S. WATSON

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1992 Volume 45 Issue 5 Pages 648-658

DOI https://doi.org/10.7164/antibiotics.45.648

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Abstract

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.

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