Shoeb, Mohammad and MacManus, Stephen M. and Jaspars, Marcel and Trevidu, Jioji N. and Nahar, Lutfun and Kong-Thoo-Lin, Paul and Sarker, Satyajit D. (2006) 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. Tetrahedron, 62 (48). 11172 - 11177. ISSN 0040-4020
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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).
| Item Type: | Journal Article |
|---|---|
| Additional Information: | Journal Supports Open access |
| Uncontrolled Keywords: | Dimer |
| Subjects: | Q Science > QD Chemistry Q Science > QH Natural history > QH301 Biology |
| Divisions: | Faculty of Science, Technology and Environment (FSTE) > School of Biological and Chemical Sciences |
| Depositing User: | Repo Editor |
| Date Deposited: | 09 Jun 2017 00:01 |
| Last Modified: | 09 Jun 2017 00:01 |
| URI: | https://repository.usp.ac.fj/id/eprint/9923 |
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