Limonoids from Cipadessa baccifera

J Nat Prod. 2020 Jun 26;83(6):1751-1765. doi: 10.1021/acs.jnatprod.9b00666. Epub 2020 May 29.

Abstract

Eighteen new limonoids, including eight methyl angolensates (1-8) and 10 cipadesins (9-18), were isolated from the leaves of Cipadessa baccifera. Their structures were characterized by means of spectroscopic data analyses, single-crystal X-ray diffraction, and quantum chemistry computational methods. The C-6 configurations in those compounds possessing a C-6 hydroxy group were all assigned as S regardless of the magnitude of J5,6, and the C-2' configuration in those bearing a 2-methylbutyryl residue was defined by single-crystal X-ray diffraction and NMR data. Compounds 1, 5, 6, 7, 11, and 12 showed moderate antimalarial activities with IC50 values ranging from 12 to 28 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antimalarials / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry
  • Limonins / chemistry*
  • Limonins / pharmacology
  • Magnetic Resonance Spectroscopy
  • Meliaceae / chemistry*
  • Molecular Conformation
  • Molecular Structure
  • Plant Leaves / chemistry
  • Plasmodium falciparum / drug effects
  • Spectrometry, Mass, Electrospray Ionization
  • X-Ray Diffraction

Substances

  • Antimalarials
  • Antineoplastic Agents, Phytogenic
  • Limonins