Antiproliferative alkaloids from Crinum zeylanicum |
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Authors: | Berkov Strahil Romani Stefania Herrera Maria Viladomat Francesc Codina Carles Momekov Georgi Ionkova Iliana Bastida Jaume |
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Institution: | Departament de Productes Naturals, Biologia Vegetal i Edafologia, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Catalonia, Spain. |
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Abstract: | Crinum zeylanicum is used in folk medicine as a rubefacient in rheumatism, a treatment for malaria or as a poison. Complex alkaloid profiles in C. zeylanicum plant organs were revealed by GC‐MS analysis, including several bioactive compounds. Crinine, lycorine, 11‐O‐acetoxyambelline, ambelline, 6‐hydroxybuphanidrine and 6‐ethoxybuphanidrine (an artefact of the isolation procedure) were isolated. Crinine, 6‐hydroxybuphanidrine and 6‐ethoxybuphanidrine showed antiproliferative effects against human tumor cell lines, crinine being the most active (IC50 14.04 μm against HL‐60/Dox). The latter compound induced apoptosis in a dose‐dependent manner in HL‐60 and MDA‐MB‐231 cell lines. Structure‐activity relationships in the studied molecules indicated that the hydrogenation of the double bond at C1‐C2 leads to a loss of activity, whereas substitutions at C6, C8 and C11 affect their cytotoxicity. Copyright © 2011 John Wiley & Sons, Ltd. |
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Keywords: | Crinum zeylanicum Amaryllidaceae alkaloids apoptosis cytotoxicity |
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