Diversonol and blennolide derivatives from the endophytic fungus Microdiplodia sp. Absolute configuration of diversonol

Imran Nafees Siddiqui, Aqib Zahoor, Hidayat Hussain, Ishtiaq Ahmed, Viqar Uddin Ahmad, Daniele Padula, Siegfried Draeger, Barbara Schulz, Kathrin Meier, Michael Steinert, Tibor Kurtán, Ulrich Flörke, Gennaro Pescitelli, Karsten Krohn

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44 Citations (Scopus)

Abstract

Chemical investigation of the fungal strain Microdiplodia sp. isolated from the shrub Lycium intricatum led to the isolation of four new compounds: a hexahydroxanthone (2), a 2,3-dihydrochroman-4-one (3), a 7-oxoxanthone derivative (4), and a 1,4-oxazepan-7-one (5). The relative configurations of the new compounds were determined by intensive NMR investigations, notably NOESY experiments at different temperatures. The absolute configurations of the well-known fungal metabolite diversonol (1) and of other xanthone derivatives (3, 4) were established by means of TDDFT ECD calculations. Most of the metabolites were biologically active, with antibacterial activity against Legionella pneumophila and/or antifungal activity against Microbotryum violaceum.

Original languageEnglish
Pages (from-to)365-373
Number of pages9
JournalJournal of Natural Products
Volume74
Issue number3
DOIs
Publication statusPublished - Mar 25 2011

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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    Siddiqui, I. N., Zahoor, A., Hussain, H., Ahmed, I., Ahmad, V. U., Padula, D., Draeger, S., Schulz, B., Meier, K., Steinert, M., Kurtán, T., Flörke, U., Pescitelli, G., & Krohn, K. (2011). Diversonol and blennolide derivatives from the endophytic fungus Microdiplodia sp. Absolute configuration of diversonol. Journal of Natural Products, 74(3), 365-373. https://doi.org/10.1021/np100730b