2. Academic Validation
  3. Isoswinholide B and swinholide K, potently cytotoxic dimeric macrolides from Theonella swinhoei

Isoswinholide B and swinholide K, potently cytotoxic dimeric macrolides from Theonella swinhoei

  • Bioorg Med Chem. 2013 Sep 1;21(17):5332-8. doi: 10.1016/j.bmc.2013.06.015.
Annamaria Sinisi 1,  Barbara Calcinai,  Carlo Cerrano,  Henny A Dien,  Angela Zampella,  Claudio D'Amore,  Barbara Renga,  Stefano Fiorucci,  Orazio Taglialatela-Scafati
Affiliations

Affiliation

  • 1 Dipartimento di Farmacia, Università di Napoli 'Federico II', Via D. Montesano 49, 80131 Napoli, Italy.
PMID: 23830699 DOI: 10.1016/j.bmc.2013.06.015
Abstract

Chemical investigation of an Indonesian specimen of Theonella swinhoei afforded the new dimeric macrolides isoswinholide B (5) and swinholide K (6), along with the known swinholides A (1), B (2) and D (3) and isoswinholide A (4). Isoswinholide B showed an unprecedented 21/19' lactonization pattern, while swinholide K included an sp(2) methylene attached at C-4 and an additional oxymethine group at C-5, whose configuration has been determined through application of J-based configuration analysis. The isolated swinholides (1-6), with the exception of isoswinholide B, showed a cytotoxic activity on HepG2 (hepatocarcinoma cell line) in the nanomolar range.

Keywords

Actin-binding cytotoxins; Macrolides; Swinholides; Theonella swinhoei.

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