Neocucurbitacin D, a novel lactone-type norcucurbitacin as xanthine oxidase inhibitor from Herpetospermum pedunculosum

Nat Prod Res. 2020 Jun;34(12):1728-1734. doi: 10.1080/14786419.2018.1528592. Epub 2018 Nov 17.

Abstract

A novel lactone-type norcucurbitacin, designated as neocucurbitacin D (1), together with five known cucurbitane triterpenes were isolated from traditional Tibetan medicine "Se Ji Mei Duo", which is the seed of Herpetospermum pedunculosum (Ser.) C.B. Clarke. The structure of neocucurbitacin D was elucidated by spectroscopic analysis, including 2D NMR and X-ray techniques. Compounds 1-6 were screened for their xanthine oxidase (XOD) inhibitory activity. Compound 1, 2 and 4 exhibited significant XOD inhibition with IC50 values ranging from 10.16 to 18.41 μM. The absolute stereochemistry and XOD inhibitiory activity of lactone-type norcucurbitacins was reported firstly.

Keywords: Cucurbitane triterpenes; Herpetospermum pedunculosum; Norcucurbitacin; Xanthine oxidase inhibitor.

MeSH terms

  • Cucurbitaceae / chemistry*
  • Cucurbitacins
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology
  • Glycosides
  • Humans
  • Inhibitory Concentration 50
  • Lactones / chemistry
  • Lactones / isolation & purification
  • Lactones / pharmacology
  • Molecular Conformation
  • Seeds / chemistry
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*
  • Xanthine Oxidase / antagonists & inhibitors*

Substances

  • Enzyme Inhibitors
  • Glycosides
  • Lactones
  • Triterpenes
  • cucurbitane
  • cucurbitacin D
  • Cucurbitacins
  • Xanthine Oxidase