Cancer preventive investigation of new compounds from Echinophora cinerea, a condiment

Aerial parts of Echinophora cinerea (Apiaceae) are used as vegetable and as yogurt and cheese seasoning. It is used for the treatment of digestive disorders in parts of Iran as well. Despite several biological investigations on the plant, our team is the only group working on its chemistry and several research has been performed up to now. Due to importance of chemopreventive effects of edible plants, the phytochemicals of the plant were investigated on several cancerous cell lines. Powdered aerial parts of the plant were macerated with acetone and EtOH:H2O (8:2), respectively. The former was fractionated on RP-18 sorbent using mixture of methanol and water and resulted fractions were analyzed by NMR and promising fractions were refractionated and purified using normal or reversed phase column chromatography and preparative HPLC analyses. Hydroalcoholic extract was fractionated by VLC and finally purified using reversed phase HPLC. Structures of pure compounds were determined with 1D and 2D NMR and mass analyses. The effect of compounds on MCF-7, SKNMC, PC3 and PC12 cell lines were investigated. Three new polyacetylenes (echinophorin A-C, 1-3), an iridoid (Verbenone-5-O-glucoside, 4) and a coumarin (osthol, 5) were isolated from acetone extract. Cell cytotoxicity of pure compounds was evaluated with MTT assay on MCF-7, SKNMC and PC3 cell lines. Echinophorin A and B show cytotoxicity effect on PC3 and SKNMC cell line with IC50 as 23 and 25 μg/ml on PC3, respectively. Six compounds (quercetin-3-O- -D-glucopyranoside, 6, Kaempferol glycoside, 7, osthol, 5, verbenone glycoside, 4, isoimperatorin, 8 and echinophorin B, 2) were purified from hydroethanol extract. Treatment of PC12 cells with 6 and 5 before exposure to the cisplatin increased cell viability and decreased apoptosis through up-regulation of Bcl2, inhibition of caspase-3 activity and increasing of mitochondrial membrane potential. As well, 5 decreased ROS generation induced by cisplatin. 6 prevented cytotoxicity of H2O2 in PC12 cell line and led to a decrease in the generation of reactive oxygen species. Conclusion: Echinophora cinerea is a good source of protective and antioxidant natural products. Since, it is an edible plant, it can be considered as a safe supplementary.

Echinophora cinerea, polyacetylenes, iridoid, coumarin