Scalemic Caged Xanthones Isolated from the Stem Bark Extract of Garcinia propinqua

J Nat Prod. 2017 May 26;80(5):1658-1667. doi: 10.1021/acs.jnatprod.7b00240. Epub 2017 May 10.

Abstract

Seven new caged xanthones, doitunggarcinones E-K (1-7), all as scalemic mixtures and 10 known compounds (8-17), were isolated from the stem bark extract of Garcinia propinqua. The structures were elucidated on the basis of spectroscopic methods. The separation of the enantiomers of 1-6 was achieved by semipreparative chiral HPLC. The absolute configuration of compound (+)-1 was determined by single-crystal X-ray crystallographic analysis using Cu Kα radiation. The absolute configurations of the other related compounds were determined from comparisons of their ECD spectra with that of compound (+)-1. Compounds (-)-6 and 7 showed cytotoxicity against a colon cancer cell line with IC50 values of 14.23 and 23.95 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Cell Line, Tumor
  • Chromatography, High Pressure Liquid
  • Colonic Neoplasms / drug therapy*
  • Garcinia / chemistry*
  • Humans
  • Molecular Structure
  • Plant Bark / chemistry*
  • Plant Stems / chemistry*
  • Stereoisomerism
  • Xanthones / chemistry
  • Xanthones / isolation & purification*
  • Xanthones / pharmacology*

Substances

  • Antineoplastic Agents, Phytogenic
  • Xanthones
  • chdoitunggarcinone J
  • doitunggarcinone