Kingianic acids A-G, Endiandric acid analogues from Endiandra kingiana

Molecules. 2014 Jan 31;19(2):1732-47. doi: 10.3390/molecules19021732.

Abstract

A phytochemical investigation of the methanolic extract of the bark of Endiandra kingiana led to the isolation of seven new tetracyclic endiandric acid analogues, kingianic acids A-G (1-7), together with endiandric acid M (8), tsangibeilin B (9) and endiandric acid (10). Their structures were determined by 1D- and 2D-NMR analysis in combination with HRMS experiments. The structure of compounds 9 and 10 were confirmed by single-crystal X-ray diffraction analysis. These compounds were screened for Bcl-xL and Mcl-1 binding affinities and cytotoxic activity on various cancer cell lines. Compound 5 showed moderate cytotoxic activity against human colorectal adeno-carcinoma (HT-29) and lung adenocarcinoma epithelial (A549) cell lines, with IC50 values in the range 15-17 µM, and compounds 3, 6 and 9 exhibited weak binding affinity for the anti-apoptotic protein Mcl-1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Apoptosis / drug effects
  • Carboxylic Acids / chemistry*
  • Drug Screening Assays, Antitumor
  • HT29 Cells
  • Humans
  • Lauraceae / chemistry*
  • Molecular Structure*
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology
  • X-Ray Diffraction

Substances

  • Antineoplastic Agents, Phytogenic
  • Carboxylic Acids
  • Plant Extracts
  • endiandric acid