Montamine, a unique dimeric indole alkaloid, from the seeds of Centaurea montana (Asteraceae), and its in vitro cytotoxic activity against the CaCo2 colon cancer cells |
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Authors: | Mohammad Shoeb Marcel Jaspars Lutfun Nahar Satyajit D Sarker |
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Institution: | a Department of Chemistry, University of Dhaka, Dhaka 1000, Bangladesh b School of Pharmacy, The Robert Gordon University, Schoolhill, Aberdeen AB10 1FR, UK c Marine Natural Products Laboratory, Department of Chemistry, University of Aberdeen, Aberdeen AB24 3UE, UK d School of Life Sciences, The Robert Gordon University, St Andrew Street, Aberdeen AB25 1HG, UK e School of Biomedical Sciences, University of Ulster at Coleraine, Cromore Road, Coleraine BT52 1SA, Co. Londonderry, Northern Ireland, UK |
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Abstract: | Reversed-phase HPLC analysis of the methanol extract of the seeds of Centaurea montana afforded a flavanone, montanoside (4), six epoxylignans, berchemol (7), berchemol 4′-O-β-d-glucoside (5), pinoresinol (10), pinoresinol 4-O-β-d-glucoside (8), pinoresinol 4,4′-di-O-β-d-glucoside (6), pinoresinol 4-O-apiose-(1→2)-β-d-glucoside (9), two quinic acid derivatives, trans-3-O-p-coumaroylquinic acid (1), cis-3-O-p-coumaroylquinic acid (2), and eight indole alkaloids, tryptamine (3), N-(4-hydroxycinnamoyl)-5-hydroxytryptamine (11), cis-N-(4-hydroxycinnamoyl)-5-hydroxytryptamine (12), centcyamine (16), cis-centcyamine (17), moschamine (13), cis-moschamine (14) and a dimeric indole alkaloid, montamine (15). While the structures of two new compounds, montanoside (4) and montamine (15), were established unequivocally by UV, IR, MS and a series of 1D and 2D NMR analyses, all known compounds were identified by comparison of their spectroscopic data with literature data. The antioxidant properties of these compounds were assessed by the DPPH assay, and their toxicity towards brine shrimps and cytotoxicity against CaCo-2 colon cancer cells were evaluated by the brine shrimp lethality and the MTT cytotoxicity assays, respectively. The novel dimer, montamine (15), showed significant in vitro anticolon cancer activity (IC50=43.9 μM) while that of the monomer, moschamine (13), was of a moderate level (IC50=81.0 μM). |
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Keywords: | Centaurea montana Asteraceae DPPH assay Cytotoxicity MTT assay Colon cancer Brine shrimp lethality assay Lignan Flavanone Indole alkaloids Dimer |
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