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Latrunculin with a highly oxidized thiazolidinone ring: structure assignment and actin docking.

ABSTRACT: A new latrunculin, oxalatrunculin B (3), was isolated from Red Sea sponge Negombata corticata. Extensive spectroscopic analysis revealed an unprecedented heterocycle in which the rare thiazolidinone ring found in latrunculins was oxidized with three additional oxygens. An actin polymerization inhibition assay agreed with MM-PBSA free energy calculations that 3 binds more weakly than latrunculin B to actin. Significant antifungal and anticancer activity of 3 was found, suggesting an alternate target in addition to actin for latrunculin bioactivity.

SUBMITTER: Ahmed SA

PROVIDER: S-EPMC2529398 | biostudies-literature | 2007 Nov

REPOSITORIES: biostudies-literature

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Latrunculin with a highly oxidized thiazolidinone ring: structure assignment and actin docking.

Ahmed Safwat A SA Odde Srinivas S Daga Pankaj R PR Bowling John J JJ Mesbah Mostafa K MK Youssef Diaa T DT Khalifa Sherief I SI Doerksen Robert J RJ Hamann Mark T MT

Organic letters 20071012 23

A new latrunculin, oxalatrunculin B (3), was isolated from Red Sea sponge Negombata corticata. Extensive spectroscopic analysis revealed an unprecedented heterocycle in which the rare thiazolidinone ring found in latrunculins was oxidized with three additional oxygens. An actin polymerization inhibition assay agreed with MM-PBSA free energy calculations that 3 binds more weakly than latrunculin B to actin. Significant antifungal and anticancer activity of 3 was found, suggesting an alternate tar ...[more]

PMID: 17929935

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