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Antiproliferative Alkaloids from Crinum zeylanicum
Author(s) -
Berkov Strahil,
Romani Stefania,
Herrera Maria,
Viladomat Francesc,
Codina Carles,
Momekov Georgi,
Ionkova Iliana,
Bastida Jaume
Publication year - 2011
Publication title -
phytotherapy research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.019
H-Index - 129
eISSN - 1099-1573
pISSN - 0951-418X
DOI - 10.1002/ptr.3468
Subject(s) - lycorine , alkaloid , cytotoxicity , traditional medicine , amaryllidaceae , apoptosis , stereochemistry , cell culture , folk medicine , chemistry , biology , botany , biochemistry , medicine , in vitro , genetics
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 (IC 50 14.04 μ m 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.