Phenanthrenes and a dihydrophenanthrene from Tamus communis and their cytotoxic activity

Phytochemistry. 2007 Mar;68(5):687-91. doi: 10.1016/j.phytochem.2006.10.028. Epub 2006 Dec 12.

Abstract

From the petroleum ether extract of the rhizomes of Tamus communis, the 7-hydroxy-2,3,4,8-tetramethoxyphenanthrene (1) was isolated, together with the known 2,3,4-trimethoxy-7,8-methylenedioxyphenanthrene (2), 3-hydroxy-2,4,-dimethoxy-7,8-methylenedioxyphenanthrene (3), 2-hydroxy-3,5,7-trimethoxyphenanthrene (4) and 2-hydroxy-3,5,7-trimethoxy-9,10-dihydrophenanthrene (5), through cytotoxic assay guidance. The structures were determined by means of HREIMS, (1)H NMR, JMOD and NOESY experiments. The cytotoxic effects of the isolated compounds were tested on cervix adenocarcinoma (HeLa) cells, with the MTT assay. The results demonstrated that, with the exception of 2, all these compounds displayed pronounced cytotoxic activity; especially 1 and 3 exhibited significant cell growth inhibitory effects, with IC(50)=8.52+/-0.70 and 3.64+/-0.12 microM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Survival / drug effects*
  • Combretum / chemistry
  • HeLa Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Phenanthrenes / chemistry
  • Phenanthrenes / isolation & purification*
  • Phenanthrenes / pharmacology*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Rhizome / chemistry
  • Tamus / chemistry*

Substances

  • Phenanthrenes
  • Plant Extracts