Metabolic products of the endophytic fungus Microsphaeropsis sp. from Larix decidua

Jingqiu Dai, Karsten Krohn, Brigitta Elsässer, Ulrich Flörke, Siegfried Draeger, Barbara Schulz, Gennaro Pescitelli, Piero Salvadori, Sándor Antus, Tibor Kurtán

Research output: Contribution to journalArticle

40 Citations (Scopus)

Abstract

Five new metabolites, palmarumycin M1 (1a) and M2 (3), papyracillic acid C (6) and the microsphaeropsins A (7) and B (8) were isolated from the fungus Microsphaeropsis sp. together with the known decaspirone (2) and the papyracillic acids A and B (4 and 5). Their structures were determined by means of spectroscopic data including HREIMS, 1H NMR, 13C NMR, 2D NMR (HMQC, HMBC, NOESY) and X-ray single crystal analysis. The absolute configuration of palmarumycin M1 (1a) was determined by single-crystal X-ray analysis of the bis(4-bromobenzoate) 1c and the relationship between 1a, 2 and 3 established by chemical transformation of 1a into 2 and of 3 into 2. The relative configuration of papyracillic acids A-C (4-6) was revised and their absolute configuration determined by comparison of TDDFT-calculated and experimental solid-state CD spectra.

Original languageEnglish
Pages (from-to)4845-4854
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number29
DOIs
Publication statusPublished - Oct 24 2007

Keywords

  • Exciton chirality
  • Fungal secondary metabolites
  • Microsphaeropsins
  • Microsphaeropsis sp.
  • Palmarumycins M
  • Papyracillic acids
  • Solid-state CD

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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  • Cite this

    Dai, J., Krohn, K., Elsässer, B., Flörke, U., Draeger, S., Schulz, B., Pescitelli, G., Salvadori, P., Antus, S., & Kurtán, T. (2007). Metabolic products of the endophytic fungus Microsphaeropsis sp. from Larix decidua. European Journal of Organic Chemistry, (29), 4845-4854. https://doi.org/10.1002/ejoc.200700348