Purpurolide A, 5/5/5 Spirocyclic Sesquiterpene Lactone in Nature from the Endophytic Fungus Penicillium purpurogenum

Org Lett. 2018 Nov 16;20(22):7341-7344. doi: 10.1021/acs.orglett.8b03323. Epub 2018 Nov 5.

Abstract

Purpurolide A (1), an unprecedent sesquiterpene lactone with a rarely encountered 5/5/5 spirocyclic skeleton, along with two new 6/4/5/5 tetracyclic sesquiterpene lactones (2 and 3), were isolated from the cultures of the endophytic fungus Penicillium purpurogenum IMM003. The structures and absolute configurations of 1-3 were established by spectroscopic analysis, single-crystal X-ray diffraction, and calculations of the 13C NMR and ECD data. Compounds 1-3 showed significant inhibitory activity against pancreatic lipase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Lactones / chemistry
  • Lactones / isolation & purification*
  • Lactones / pharmacology
  • Lipase / antagonists & inhibitors
  • Molecular Structure
  • Penicillium / isolation & purification
  • Penicillium / metabolism*
  • Plant Leaves / microbiology
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Spiro Compounds / pharmacology
  • Stereoisomerism
  • Thymelaeaceae / microbiology

Substances

  • Enzyme Inhibitors
  • Lactones
  • Sesquiterpenes
  • Spiro Compounds
  • Lipase