Methyl angolensate and mexicanolide-type limonoids from the seeds of Cipadessa baccifera

Phytochemistry. 2014 Feb:98:174-82. doi: 10.1016/j.phytochem.2013.11.006. Epub 2013 Dec 13.

Abstract

Six new methyl angolensate type (1-6) and three new mexicanolide-type (7-9) limonoids, along with six known limonoids (10-15), were isolated from the seeds of Cipadessa baccifera. The structures of all these compounds were established by extensive 1D, 2D NMR, and HRESIMS experiments, and structures of 11 and 13 were further confirmed by a single crystal X-ray diffraction analysis, which are reported for the first time. The cytotoxic activities of these isolates were also studied against A549, MCF7, ME-180, HT-29, B-16, ACHN cancer cell lines using MTT assay, and results indicated that compounds 4, 10, and 14 displayed potent cytotoxic activity against B-16, ACHN cell lines with an IC50 values of 8.51 and 7.0 μg/mL, respectively.

Keywords: Cancer cell lines; Cipadessa baccifera; Cytotoxic activity; Limonoids.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Crystallography, X-Ray
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HT29 Cells
  • Humans
  • Limonins / chemistry
  • Limonins / isolation & purification
  • Limonins / pharmacology*
  • MCF-7 Cells
  • Magnetic Resonance Spectroscopy
  • Meliaceae / chemistry*
  • Mice
  • Models, Molecular
  • Molecular Conformation
  • Seeds / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Structure-Activity Relationship
  • Triterpenes / chemistry
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Limonins
  • Triterpenes
  • methyl angolensate