Structure elucidation and absolute configuration of metabolites from the soil-derived fungus Dictyosporium digitatum using spectroscopic and computational methods

Trong D. Tran, Brice A.P. Wilson, Curtis J. Henrich, Karen L. Wendt, Jarrod King, Robert H. Cichewicz, Alberto M. Stchigel, Andrew N. Miller, Barry R. O'Keefe, Kirk R. Gustafson

Research output: Contribution to journalArticlepeer-review

Abstract

Following the discovery of a new class of compounds that inhibit the mucosa-associated lymphoid tissue lymphoma translocation 1 (MALT1) protease in a prior study, further chemical investigation of the Dictyosporium digitatum fungus resulted in the identification of 16 additional metabolites, including 12 undescribed compounds (1–12). The constitution and relative configuration of these new molecules were established by comprehensive NMR and HRMS analyses. Their absolute configurations were determined by employing Mosher's ester analysis and TDDFT ECD calculations. Two sesquiterpenes, dictyosporins A (1) and B (2), possess an undescribed eudesmen-type of structural scaffold. The ability of the isolated compounds to inhibit MALT1 proteolytic activity was evaluated, but none of them exhibited significant inhibition.

Original languageEnglish (US)
Article number112278
JournalPhytochemistry
Volume173
DOIs
StatePublished - May 2020

Keywords

  • DFT calculations
  • Dictyosporiaceae
  • Dictyosporin
  • Dictyosporium digitatum
  • Mosher's ester analysis
  • Structure elucidation

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Plant Science
  • Horticulture

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