Pseudoanguillosporin A and B: Two new isochromans isolated from the endophytic fungus Pseudoanguiliospom sp.

Ines Kock, Siegfried Draeger, Barbara Schulz, Brigitta Elsässer, Tibor Kurtán, Ágnes Kenéz, Sándor Antus, Gennaro Pescitelli, Piero Salvadori, John Bryan Speaknian, Joachim Rheinheinier, Karsten Krohn

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35 Citations (Scopus)

Abstract

Two new isochromans named pseudoanguillosporin A (2a) and B (3), together with the known cephalochromin (1), were isolated from Pseudoanguiliospom sp. The C-2 absolute configuration of 2a and 3 was deduced from its CD spectrum by the isochroman helicity rule, supported by TDDFT CD calculations. The absolute configuration of the sec-hydroxyl group of 3 was determined by the Mosher NMR method from the MPA esters of its methylated derivative. The axial chirality of 1 was assigned through exciton analysis of its CD spectrum and confirmed by ZINDO CD calculations. The metabolites showed broad antimicrobial activities.

Original languageEnglish
Pages (from-to)1427-1434
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number9
DOIs
Publication statusPublished - Mar 1 2009

Keywords

  • Biological activity
  • Circular dichroism
  • Isochromans
  • NMR spectroscopy
  • Natural products

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Kock, I., Draeger, S., Schulz, B., Elsässer, B., Kurtán, T., Kenéz, Á., Antus, S., Pescitelli, G., Salvadori, P., Speaknian, J. B., Rheinheinier, J., & Krohn, K. (2009). Pseudoanguillosporin A and B: Two new isochromans isolated from the endophytic fungus Pseudoanguiliospom sp. European Journal of Organic Chemistry, (9), 1427-1434. https://doi.org/10.1002/ejoc.200801083