Melipatulinones A-C, Three Lignan-Phloroglucinol Hybrids from Melicope patulinervia

Org Lett. 2020 Feb 21;22(4):1380-1384. doi: 10.1021/acs.orglett.9b04680. Epub 2020 Jan 30.

Abstract

(±)-Melipatulinones A-C (1-3), three unique enantiomeric pairs of lignan-phloroglucinol hybrids along with the biogenetically related compound melipatulignan A (4), were isolated from the leaves of Melicope patulinervia. Melipatulinones A (1) and B (2) share a novel spiro[hydrobenzofuran-2,3'-furan] 5/5/6 tricyclic ring system, while melipatulinone C (3) features an unprecedented spiro[cyclopenta[b]hydrofuran-2,3'-furan] 5/5/5 tricyclic framework. Their structures were determined by spectroscopic methods, electronic circular dichroism (ECD) calculations, and X-ray diffraction. Compounds 1-3 exhibited a pancreatic lipase inhibitory effect.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Lignans / chemistry
  • Lignans / isolation & purification
  • Lignans / pharmacology*
  • Lipase / antagonists & inhibitors*
  • Lipase / metabolism
  • Molecular Conformation
  • Pancreas / enzymology
  • Plant Leaves / chemistry
  • Rutaceae / chemistry*
  • Stereoisomerism

Substances

  • Enzyme Inhibitors
  • Lignans
  • Lipase