Inhibition of MMP-2 secretion from brain tumor cells suggests chemopreventive properties of a furanocoumarin glycoside and of chalcones isolated from the twigs of Dorstenia turbinata

Phytochemistry. 2006 Dec;67(23):2573-9. doi: 10.1016/j.phytochem.2006.09.017. Epub 2006 Oct 30.

Abstract

A furanocoumarin glycoside new named turbinatocoumarin (1) was isolated from the twigs of Dorstenia turbinata. The structure of turbinatocoumarin (1) was assigned as 5-methoxy-3-[3-(beta-glucopyranosyloxy)-2-hydroxy-3-methylbutyl]psoralen by means of spectroscopic analysis. Known compounds have also been isolated from this genus and identified as (2'S, 3'R)-3'-hydroxymarmesin (2), 5-methoxy-3-(3-methyl-2,3-dihydroxybutyl)psoralen (3), psoralen (4), kanzonol C (5) which was isolated for the first time from this genus, 4-hydroxylonchocarpin (6), umbelliferone, 4-hydroxy-3-methoxybenzaldehyde and 4-methoxyphenol. As part of our continuing search for potential naturally-occurring antitumor drug candidates, the inhibition of matrix metalloproteinase (MMP)-2 secretion from brain tumor-derived glioblastoma cells by the isolated compounds 1, 3, 5, and 6 was evaluated by zymography and compared to the documented naturally-occurring MMP secretion inhibitors chlorogenic acid (CHL) and epigallocatechin-3-gallate (EGCg). Among the compounds tested, the inhibiting MMP secretion concentrations ranged from 0.025 to 250 microM with up to 80% inhibition. The inhibitory activities of compounds 5 and 6 were found comparable to the common reference compounds CHL and EGCg. This suggests that alternate sources can be explored and exploited for the availability of chemopreventive molecules.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / metabolism
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Brain Neoplasms / metabolism*
  • Cell Line, Tumor
  • Chalcones / chemistry
  • Chalcones / metabolism
  • Chalcones / pharmacology*
  • Furocoumarins / chemistry
  • Furocoumarins / metabolism
  • Furocoumarins / pharmacology*
  • Glioblastoma / enzymology
  • Glycosides / chemistry
  • Glycosides / metabolism
  • Glycosides / pharmacology*
  • Humans
  • Matrix Metalloproteinase 2 / metabolism*
  • Molecular Structure
  • Moraceae / chemistry
  • Moraceae / metabolism*

Substances

  • Antineoplastic Agents, Phytogenic
  • Chalcones
  • Furocoumarins
  • Glycosides
  • Matrix Metalloproteinase 2