New anthracene derivatives – structure elucidation and antimicrobial activity

Abdessamad Debbab, Amal H. Aly, Ruangelie Edrada-Ebel, Victor Wray, Alexander Pretsch, Gennaro Pescitelli, Tibor Kurtan, Peter Proksch

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

Three new anthracene derivatives, which include tetrahydroanthraquinone 1 and two tetrahydroanthraquinone heterodimers 2 and 3, were isolated from Stemphylium globuliferum, together with four known metabolites 4–7. Detailed analysis of the spectroscopic data allowed the unambiguous determination of the structures of 1 and 2 and a revision of the structure of alterporriol C and its atropisomer. Furthermore, alterporriol G, previously obtained as part of a mixture, was isolated in its pure form for the first time and its structure was also revised. The absolute configurations of 1, 2 and 3 were assigned by calculation of their CD spectra, which also allowed the configurational assignment of altersolanol A and the determination of the axial chirality of alterporriols D and E. All isolated compounds were analysed for their antimicrobial and cytotoxic activities. Compounds 1 and 5 inhibited the growth of most pathogenic microorganisms tested, whereas 2, 6 and 7 showed selective inhibition of bacteria but were inactive against fungi.
Original languageEnglish
Pages (from-to)1351-1359
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2012
DOIs
Publication statusPublished - 2012

Keywords

  • natural products
  • antibiotics
  • structure elucidation
  • circular dichroism
  • quinone

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  • Cite this

    Debbab, A., Aly, A. H., Edrada-Ebel, R., Wray, V., Pretsch, A., Pescitelli, G., Kurtan, T., & Proksch, P. (2012). New anthracene derivatives – structure elucidation and antimicrobial activity. European Journal of Organic Chemistry, 2012, 1351-1359. https://doi.org/10.1002/ejoc.201101442