New cytotoxic prenylated isoflavonoids from Bituminaria morisiana

Planta Med. 2005 Mar;71(3):254-60. doi: 10.1055/s-2005-837841.


Using cytotoxicity against KB cancer cells as a lead, bioguided-fractionation of the petroleum ether and ethyl acetate extracts of Bituminaria morisiana leaves led to the isolation of two new pterocarpans, namely 3,9-dihydroxy-4-(3,3-dimethylallyl) [6a R, 11a R]-pterocarpan, 3-hydroxy-4-(3,3-dimethylallyl)-4'',5''-dehydropyrano[8,9:2'',3''][6a R,11a R]-pterocarpan and one new isoflavone identified as 4',5''-dihydroxy-6''-methoxy-4'',4''-dimethyl-4'',5''-dihydro-6'' H-pyrano[2'',3'':7,8]-isoflavone. Moreover, two known pterocarpans, erybraedin C and bitucarpin A, three known isoflavones, daidzein, 8-prenyldaidzein and bidwillon C, one known furocoumarin, pseudoisopsoralen and one known coumestan, coumestrol were isolated. The structures of the isolated compounds were established by means of 1D and 2D NMR spectroscopy, as well as mass spectrometry. Further cytotoxicity tests against cells related to the immune system (Jurkat T, Mono-Mac-6 and polymorphonuclear cells) showed a moderate activity of the known pterocarpan erybraedin C against all cell lines used (IC (50) values between 17.6-28.8 microM). In addition, erybraedin C was found to induce necrosis in leukaemia Jurkat T cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / administration & dosage
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Antineoplastic Agents, Phytogenic / therapeutic use
  • Cell Line, Tumor / drug effects
  • Fabaceae*
  • Humans
  • Inhibitory Concentration 50
  • Isoflavones / administration & dosage
  • Isoflavones / chemistry
  • Isoflavones / pharmacology
  • Isoflavones / therapeutic use
  • Jurkat Cells / drug effects
  • KB Cells / drug effects
  • Monocytes / drug effects
  • Phytotherapy*
  • Plant Extracts / administration & dosage
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology*
  • Plant Extracts / therapeutic use
  • Plant Leaves
  • Protein Prenylation


  • Antineoplastic Agents, Phytogenic
  • Isoflavones
  • Plant Extracts