Cytotoxic bibenzyl dimers from the stems of Dendrobium fimbriatum Hook

Bioorg Med Chem Lett. 2014 Nov 15;24(22):5268-73. doi: 10.1016/j.bmcl.2014.09.052. Epub 2014 Sep 28.

Abstract

The bioassay-guided chemical investigation of the stems of Dendrobium fimbriatum Hook led to the isolation of seven first reported bibenzyl dimers with a linkage of a methylene moiety, fimbriadimerbibenzyls A-G (1-7), together with a new dihydrophenanthrene derivative (S)-2,4,5,9-tetrahydroxy-9,10-dihydrophenanthrene (8) and thirteen known compounds (9-21). The structure of the new compound was established by spectroscopic analysis. Biological evaluation of bibenzyl derivatives against five human cell lines indicated that seven of those compounds exhibited broad-spectrum and cytotoxic activities with IC50 values ranging from 2.2 to 21.2 μM. Those rare bibenzyl dimers exhibited cytotoxic activities in vitro and the cytotoxicity decreased as the number of oxygen-containing groups in the structure decreases.

Keywords: Bibenzyl dimer; Cytotoxicity; Dendrobium fimbriatum Hook; Fimbriadimerbibenzyl.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry
  • Antioxidants / isolation & purification
  • Antioxidants / toxicity
  • Bibenzyls / chemistry*
  • Bibenzyls / isolation & purification
  • Bibenzyls / toxicity
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Dendrobium / chemistry*
  • Dendrobium / metabolism
  • Dimerization
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Plant Stems / chemistry
  • Plant Stems / metabolism

Substances

  • Antioxidants
  • Bibenzyls