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.
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.
Ngameni
Bathelemy
B
Département de Chimie, Université du Québec à Montréal, Montreal, 2101 Jeanne-Mance, CP 8888, Succ., Centre-ville, Quebec, Canada H3C 3P8.
Touaibia
Mohamed
M
Patnam
Ramesh
R
Belkaid
Anissa
A
Sonna
Pascal
P
Ngadjui
Bonaventure T
BT
Annabi
Borhane
B
Roy
René
R
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D001932:Brain Neoplasms / Q000378:metabolism*; D045744:Cell Line, Tumor; D047188:Chalcones / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D011564:Furocoumarins / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D005909:Glioblastoma / Q000201:enzymology; D006027:Glycosides / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D006801:Humans; D020778:Matrix Metalloproteinase 2 / Q000378:metabolism*; D015394:Molecular Structure; D029586:Moraceae / Q000737:chemistry / Q000378:metabolism*
D000972:Antineoplastic Agents, Phytogenic; D047188:Chalcones; D011564:Furocoumarins; D006027:Glycosides; D020778:Matrix Metalloproteinase 2