Isolation, characterization and cytotoxic activity of benzophenone glucopyranosides from Mahkota Dewa (Phaleria macrocarpa (Scheff.) Boerl)

Bioorg Med Chem Lett. 2012 Nov 15;22(22):6862-6. doi: 10.1016/j.bmcl.2012.09.038. Epub 2012 Sep 20.

Abstract

Two benzophenone glucopyranosides have been isolated from the nut shell part of Mahkota Dewa. The structures were identified as 2,4',6-trihydroxy-4-methoxy-benzophenone-2-O-β-d-glucoside (Mahkoside A) and 2,4',6-trihydroxy-4-methoxy-6″-acetyl-benzophenone-2-O-β-d-glucoside (Mahkoside B). Mahkoside B was recognized as a novel compound. Furthermore, a series of benzophenone glucopyranoside derivatives (compounds 3-18) were synthesized and their bioactivities were characterized. Our results demonstrated that compound 18 has significant cytotoxicity against two esophageal cancer cell lines, stomach cancer cell line and prostate cancer cell line, with IC(50) less than 10 μM, indicating its potential activity against cancer cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzophenones / chemistry*
  • Benzophenones / isolation & purification
  • Benzophenones / toxicity
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Drug Screening Assays, Antitumor
  • Glucosides / chemical synthesis
  • Glucosides / chemistry*
  • Glucosides / isolation & purification
  • Glucosides / toxicity
  • Glycosides / chemistry*
  • Glycosides / isolation & purification
  • Glycosides / toxicity
  • Humans
  • Nuts / chemistry
  • Phenols / chemistry*
  • Phenols / isolation & purification
  • Phenols / toxicity
  • Reactive Oxygen Species / metabolism
  • Thymelaeaceae / chemistry*

Substances

  • 2,4',6-trihydroxy-4-methoxy-6'-acetylbenzophenone-2-O-glucoside
  • Benzophenones
  • Glucosides
  • Glycosides
  • Phenols
  • Reactive Oxygen Species
  • mahkoside A
  • benzophenone