Xyolide, a bioactive nonenolide from an Amazonian endophytic fungus, Xylaria feejeensis

Ezra G. Baraban, Jesse B. Morin, Gillian M. Phillips, Andrew J. Phillips, Scott A. Strobel, Jo Handelsman

Research output: Contribution to journalArticlepeer-review

Abstract

Endophytes isolated from tropical plants represent a largely untapped reservoir of bioactive secondary metabolites. We screened a library of fungal endophyte extracts for inhibition of the plant pathogen, Pythium ultimum, and purified an active compound using bioassay-guided fractionation. A new nonenolide, (4S,7S,8S,9R)-4-O-succinyl-7,8-dihydroxy-9-heptyl-nonen-9-olide, was isolated and named xyolide. The structure was elucidated by a combination of 1D and 2D NMR methods and the absolute configuration was determined by exciton-coupled circular dichroism. The MIC of xyolide against P. ultimum was 425 μM.

Original languageEnglish (US)
Pages (from-to)4058-4060
Number of pages3
JournalTetrahedron Letters
Volume54
Issue number31
DOIs
StatePublished - Jul 31 2013
Externally publishedYes

Keywords

  • Fungal endophyte
  • Natural product
  • Nonenolide
  • Pythium ultimum

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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