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 journalArticle

30 Citations (Scopus)

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 2006
Externally publishedYes

Fingerprint

Theonella
Indian Ocean
macrolides
Red Sea
Porifera
microfilaments
Actin Cytoskeleton
Actins
antineoplastic agents
Macrolides
hydroxylation
adenocarcinoma
Candida albicans
colon
skeleton
inhibitory concentration 50
cytotoxicity
chemical derivatives
Aquatic Organisms
Hydroxylation

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Hurghadolide A and swinholide I, potent actin-microfilament disrupters from the red sea sponge Theonella swinhoei. / Youssef, Diaa T A; Mooberry, Susan L.

In: Journal of Natural Products, Vol. 69, No. 1, 01.2006, p. 154-157.

Research output: Contribution to journalArticle

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