title: Antiproliferative alkaloids from Crinum zeylanicum.
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.
authors: Departament de Productes Naturals, Biologia Vegetal i Edafologia, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Catalonia, Spain.
authors: Strahil
authors: S
authors: Berkov
authors: Stefania
authors: S
authors: Romani
authors: Maria
authors: M
authors: Herrera
authors: Francesc
authors: F
authors: Viladomat
authors: Carles
authors: C
authors: Codina
authors: Georgi
authors: G
authors: Momekov
authors: Iliana
authors: I
authors: Ionkova
authors: Jaume
authors: J
authors: Bastida
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000302:isolation & purification / Q000494:pharmacology*; D017209:Apoptosis / Q000187:drug effects*; D031407:Crinum / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D018922:HL-60 Cells / Q000187:drug effects; D006801:Humans; D015394:Molecular Structure; D013329:Structure-Activity Relationship
chemical_list: D047151:Amaryllidaceae Alkaloids