Three new polyoxygenated bergamotanes from the endophytic fungus Penicillium purpurogenum IMM 003 and their inhibitory activity against pancreatic lipase

Chin J Nat Med. 2020 Jan;18(1):75-80. doi: 10.1016/S1875-5364(20)30007-8.

Abstract

Purpurolides D-F (1-3), three new polyoxygenated bergamotanes bearing a 6/4/5/5 tetracyclic ring system, were isolated from the endophytic fungus Penicillium purpurogenum IMM 003. Their structures were unambiguously elucidated based on extensive spectroscopic data analyses, 13C NMR chemical shifts calculations coupled with the DP4+ probability method, and the calculated and experimental electronic circular dichroism (ECD) spectra. Compounds 1-3 showed significant inhibitory activity against pancreatic lipase (PL). The result highlights that the presence of 3-hydroxylated decanoic acid moiety at C-14 is important for increasing the inhibition potency against PL.

Keywords: Pancreatic lipase inhibitors; Penicillium purpurogenum; Sesquiterpene lactones.

MeSH terms

  • Cell Line, Tumor
  • Humans
  • Lipase / antagonists & inhibitors*
  • Molecular Structure
  • Penicillium / chemistry*
  • Penicillium / isolation & purification*
  • Sesquiterpenes / chemistry*

Substances

  • Sesquiterpenes
  • Lipase
  • pancreatic lipase-related protein 1