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

M. Shoeb, S. M. MacManus, Marcel Jaspars, Jioji Natadra Tabudravu, L. Nahar, P. K. Thoo-Lin, S. D. Sarker

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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-beta-D-glucoside (5), pinoresinol (10), pinoresinol 4-O-beta-D-glucoside (8), pinoresinol 4,4'-di-O-beta-D-glucoside (6), pinoresinol 4-O-apiose-(1 -> 2)-beta-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 mu M) while that of the monomer, moschamine (13), was of a moderate level (IC50=81.0 mu M). (c) 2006 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)11172-11177
Number of pages5
JournalTetrahedron
Volume62
DOIs
Publication statusPublished - 2006

Keywords

  • Centaurea montana
  • Asteraceae
  • DPPH assay
  • cytotoxicity
  • MTT assay
  • colon cancer
  • brine shrimp lethality assay
  • lignan
  • flavanone
  • indole alkaloids
  • dimer
  • FLAVONOID GLYCOSIDE VARIATION
  • WILD SPECIMENS
  • CYANUS ASTERACEAE
  • LIGNAN GLYCOSIDES
  • CONSTITUENTS
  • IDENTIFICATION
  • COMPOSITAE
  • MOSCHATA
  • LEAVES

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