Hurghadolide A and swinholide I, potent actin-microfilament disrupters from the red sea sponge Theonella swinhoei

Diaa T.A. Youssef, Susan L. Mooberry

Research output: Contribution to journalArticlepeer-review

31 Scopus citations

Abstract

As part of our continuing interest in identifying anticancer drug leads from Red Sea marine organisms, we have investigated the sponge Theonella swinhoei. We report here the isolation and structure elucidation of swinholide A (1) and two new macrolides, swinholide I (2) and hurghadolide A (3). Swinholide I is the first derivative of swinholide A with hydroxylation at the side chain. Hurghadolide A possesses an unprecedented asymmetric 42-membered dilactone moiety and presents a novel skeleton of macrolides. The structural determinations were based on extensive interpretation of high-field NMR spectra and HRFABMS data. Swinholide I and hurghadolide A showed in vitro cytotoxicity against human colon adenocarcinoma (HCT-116) with IC50 values of 5.6 and 365 nM, respectively. Furthermore, swinholide I and hurghadolide A caused disruption of the actin cytoskeleton at concentrations of 70 and 7.3 nM, respectively. In addition, both compounds were active against Candida albicans.

Original languageEnglish (US)
Pages (from-to)154-157
Number of pages4
JournalJournal of Natural Products
Volume69
Issue number1
DOIs
StatePublished - Jan 1 2006
Externally publishedYes

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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