Didemnaketals F and G, new bioactive spiroketals from a Red Sea ascidian Didemnum species

Lamiaa A. Shaala, Diaa T.A. Youssef, Sabrin R.M. Ibrahim, Gamal A. Mohamed, Jihan M. Badr, April L. Risinger, Susan L. Mooberry

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

In continuation of our ongoing efforts to identify bioactive compounds from Red Sea marine organisms, a new collection of the ascidian Didemnum species was investigated. Chromatographic fractionation and HPLC purification of the CH2Cl2 fraction of an organic extract of the ascidian resulted in the identification of two new spiroketals, didemnaketals F (1) and G (2). The structure determination of the compounds was completed by extensive study of 1D (1H, 13C, and DEPT) and 2D (COSY, HSQC, and HMBC) NMR experiments in addition to high-resolution mass spectral data. Didemnaketal F (1) and G (2) differ from the previously reported compounds of this class by the lack the terminal methyl ester at C-1 and the methyl functionality at C-2. Instead, 1 and 2 possess a methyl ketone moiety instead of the terminal ester. Furthermore, didemnaketal F possesses a disubstituted double bond between C-2 and C-3, while the double bond was replaced by a secondary alcohol at C-3 in didemnaketal G. In addition, they possess the unique spiroketal/hemiketal functionality which was previously reported in didemnaketal E. Didemnaketals F (1) and G (2) displayed moderate activity against HeLa cells with of IC50s of 49.9 and 14.0 μM, respectively. In addition, didemnaketal F (1) displayed potent antimicrobial activity against E. coli and C. albicans. These findings provide further insight into the biosynthetic capabilities of this ascidian and the chemical diversity as well as the biological activity of this class of compounds.

Original languageEnglish (US)
Pages (from-to)5021-5034
Number of pages14
JournalMarine Drugs
Volume12
Issue number9
DOIs
StatePublished - Sep 1 2014

Keywords

  • Antimicrobial activity
  • Antiproliferative and cytotoxic activity
  • Didemnaketals F and G
  • Didemnum species
  • HeLa cells
  • Red sea ascidian
  • Spiroketals

ASJC Scopus subject areas

  • Drug Discovery

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