RRC ID 44313
Author Ukiya M, Sawada S, Kikuchi T, Kushi Y, Fukatsu M, Akihisa T.
Title Cytotoxic and apoptosis-inducing activities of steviol and isosteviol derivatives against human cancer cell lines.
Journal Chem Biodivers
Abstract Seventeen steviol derivatives, i.e., 2-18, and 19 isosteviol derivatives, i.e., 19-37, were prepared from a diterpenoid glycoside, stevioside (1). Upon evaluation of the cytotoxic activities of these compounds against leukemia (HL60), lung (A549), stomach (AZ521), and breast (SK-BR-3) cancer cell lines, nine steviol derivatives, i.e., 5-9 and 11-14, and five isosteviol derivatives, i.e., 28-32, exhibited activities with single-digit micromolar IC(50) values against one or more cell lines. All of these active compounds possess C(19)-O-acyl group, and among which, ent-kaur-16-ene-13,19-diol 19-O-4',4',4'-trifluorocrotonate (14) exhibited potent cytotoxicities against four cell lines with IC(50) values in the range of 1.2-4.1 μM. Compound 14 induced typical apoptotic cell death in HL60 cells upon evaluation of the apoptosis-inducing activity by flow-cytometric analysis. These results suggested that acylation of the 19-OH group of kaurane- and beyerane-type diterpenoids might be useful for enhancement of their cytotoxicities with apoptosis-inducing activity.
Volume 10(2)
Pages 177-88
Published 2013-2-1
DOI 10.1002/cbdv.201200406
PMID 23418165
MeSH Antineoplastic Agents, Phytogenic / chemistry* Antineoplastic Agents, Phytogenic / pharmacology* Apoptosis / drug effects* Cell Line, Tumor Cell Survival / drug effects Diterpenes, Kaurane / chemistry* Diterpenes, Kaurane / pharmacology* Humans Neoplasms / drug therapy Stevia / chemistry
IF 2.039
Times Cited 21
WOS Category BIOCHEMISTRY & MOLECULAR BIOLOGY CHEMISTRY, MULTIDISCIPLINARY
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Total number of mentions 13
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Human and Animal Cells HL60(RCB0041) A549(RCB0098) SK-BR-3(RCB2132)