New luffariellolide derivatives from the Indonesian sponge Acanthodendrilla sp

Ehab Elkhayat, RuAngelie Edrada, Rainer Ebel, Victor Wray, Rob van Soest, Sumaryono Wiryowidagdo, Mahmoud H Mohamed, Werner E G Müller, Peter Proksch, Ruangelie Edrada-Ebel

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23 Citations (Scopus)

Abstract

Investigation of the Indonesian sponge Acanthodendrilla sp. afforded five new luffariellolide-related sesterterpenes, acantholides A-E (1-5), in addition to luffariellolide and its 25-O-methyl and 25-O-ethyl derivatives. All structures were unambiguously established by 1D and 2D NMR and MS spectroscopy. Acantholide D and E are derivatives comprising the 1-acetylcyclopentan-5-ol moiety, which are new variants of the C(14)-C(20) segment for this type of linear sesterterpenes. Luffariellolide and its 25-O-methyl congener as well as acantholide E (5) were cytotoxic against the mouse lymphoma L5187Y cell line. Acantholide B (2), luffariellolide, and its 25-O-methyl congener were active against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis, the Gram-negative bacterium Escherichia coli, the yeast Candida albicans, and the plant pathogenic fungus Cladosporium herbarum.

Original languageEnglish
Pages (from-to)1809-1817
Number of pages9
JournalJournal of Natural Products
Volume67
Issue number11
DOIs
Publication statusPublished - Nov 2004

Keywords

  • antifungal agents
  • antineoplastic agents
  • bacillus subtilis
  • candida albicans
  • cladosporium
  • drug screening assays
  • escherichia coli
  • Indonesia
  • mice
  • microbial sensitivity tests
  • molecular structure
  • nuclear magnetic resonance
  • porifera
  • sesquiterpenes
  • sesterterpenes
  • staphylococcus aureus
  • stereoisomerism
  • terpenes

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  • Cite this

    Elkhayat, E., Edrada, R., Ebel, R., Wray, V., van Soest, R., Wiryowidagdo, S., Mohamed, M. H., Müller, W. E. G., Proksch, P., & Edrada-Ebel, R. (2004). New luffariellolide derivatives from the Indonesian sponge Acanthodendrilla sp. Journal of Natural Products, 67(11), 1809-1817. https://doi.org/10.1021/np040118j