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Cytotoxic dimeric quinolone–terpene alkaloids from the root bark of Zanthoxylum rhetsa

Four quinolone–terpene alkaloids, chelerybulgarine (1), 2′-episimulanoquinoline (3), 2,11-didemethoxyvepridimerine B (4), and rhetsidimerine (5) were isolated from the root bark of Zanthoxylum rhetsa DC. •Four quinolone–terpene alkaloids were characterised.•The C5 units of the two 2-quinolone units...

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Published in:Phytochemistry (Oxford) 2014-07, Vol.103, p.8-12
Main Authors: Ahsan, Monira, Haque, Mohammad Rashedul, Hossain, Md. Belayet, Islam, Sheikh Nazrul, Gray, Alexander I., Hasan, Choudhury Mahmood
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container_title Phytochemistry (Oxford)
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description Four quinolone–terpene alkaloids, chelerybulgarine (1), 2′-episimulanoquinoline (3), 2,11-didemethoxyvepridimerine B (4), and rhetsidimerine (5) were isolated from the root bark of Zanthoxylum rhetsa DC. •Four quinolone–terpene alkaloids were characterised.•The C5 units of the two 2-quinolone units joined in a different manner leaving a 2-methyl-2-propene chain in rhetsidimerine.•The isolated compounds were tested for cytotoxicity against a panel of six human stomach cancer cell lines. Four quinolone–terpene alkaloids, chelerybulgarine (1), 2′-episimulanoquinoline (3), 2,11-didemethoxyvepridimerine B (4), and rhetsidimerine (5) were isolated from the root bark of Zanthoxylum rhetsa DC. Chelerybulgarine (1) is a C–C linked terpene alkaloid where the C-6 of dihydrochelerythrine is linked to C-11 of the sesquiterpenoid 10β-methoxybulgarene. 2′-Episimulanoquinoline is a dimeric alkaloid containing dihydrochelerythrine and 8-methoxy-N-methylflindersine moieties, whereas 2,11-didemethoxyvepridimerine B and rhetsidimerine are dimeric prenylated quinolone alkaloids. Seven of the isolated compounds exhibited weak cytotoxicity when tested against a panel of six human stomach-cancer cell lines.
doi_str_mv 10.1016/j.phytochem.2014.03.008
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subjects 2,11-Didemethoxyvepridimerine
2′-Episimulanoquinoline
Alkaloids - chemistry
Alkaloids - pharmacology
Cell Line, Tumor
Cell Survival - drug effects
Chelerybulgarine
Dihydrochelerythrine
Humans
Molecular Structure
Plant Bark - chemistry
Plant Extracts - chemistry
Plant Extracts - pharmacology
Plant Roots - chemistry
Rhetsidimerine
Zanthoxylum - chemistry
title Cytotoxic dimeric quinolone–terpene alkaloids from the root bark of Zanthoxylum rhetsa
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