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

Research output: Contribution to journalArticle

64 Citations (Scopus)

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

Cite this

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

In: Tetrahedron, Vol. 62, 2006, p. 11172-11177.

Research output: Contribution to journalArticle

@article{2a7ba9cfa14b4370ba280085beecc6d7,
title = "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",
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.",
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",
author = "M. Shoeb and MacManus, {S. M.} and Marcel Jaspars and Tabudravu, {Jioji Natadra} and L. Nahar and Thoo-Lin, {P. K.} and Sarker, {S. D.}",
year = "2006",
doi = "10.1016/j.tet.2006.09.020",
language = "English",
volume = "62",
pages = "11172--11177",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

}

TY - JOUR

T1 - 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

AU - Shoeb, M.

AU - MacManus, S. M.

AU - Jaspars, Marcel

AU - Tabudravu, Jioji Natadra

AU - Nahar, L.

AU - Thoo-Lin, P. K.

AU - Sarker, S. D.

PY - 2006

Y1 - 2006

N2 - 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.

AB - 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.

KW - Centaurea montana

KW - Asteraceae

KW - DPPH assay

KW - cytotoxicity

KW - MTT assay

KW - colon cancer

KW - brine shrimp lethality assay

KW - lignan

KW - flavanone

KW - indole alkaloids

KW - dimer

KW - FLAVONOID GLYCOSIDE VARIATION

KW - WILD SPECIMENS

KW - CYANUS ASTERACEAE

KW - LIGNAN GLYCOSIDES

KW - CONSTITUENTS

KW - IDENTIFICATION

KW - COMPOSITAE

KW - MOSCHATA

KW - LEAVES

U2 - 10.1016/j.tet.2006.09.020

DO - 10.1016/j.tet.2006.09.020

M3 - Article

VL - 62

SP - 11172

EP - 11177

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

ER -