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

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42 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. Three new anthracene derivatives and four known metabolites were isolated from the extract of the endophytic Stemphylium globuliferum. The structures were determined by comprehensive NMR spectroscopy and MS, and the absolute configurations by TDDFT and ZINDO methods. All isolated compounds were tested for their cytotoxic and antimicrobial activities.

Original languageEnglish
Pages (from-to)1351-1359
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number7
DOIs
Publication statusPublished - Mar 1 2012

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Keywords

  • Antibiotics
  • Biological activity
  • Circular dichroism
  • Density functional calculations
  • Medicinal chemistry
  • Natural products
  • Quinones
  • Structure elucidation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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, (7), 1351-1359. https://doi.org/10.1002/ejoc.201101442