Antiproliferative Terpenoids from Almond Hulls (Prunus dulcis): Identification and Structure-Activity Relationships

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• 作者：Vincenzo Amico ; Vincenza Barresi ; Daniele Condorelli ; Carmela Spatafora ; and Corrado Tringali
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2006
• 出版时间：February 8, 2006
• 年：2006
• 卷：54
• 期：3
• 页码：810 - 814
• 全文大小：76K
• 年卷期：v.54,no.3(February 8, 2006)
• ISSN：1520-5118

文摘

Bioassay-guided fractionation of the EtOAc crude extract from Sicilian almond hulls, a waste materialfrom Prunus dulcis crop, allowed identification of 10 constituents, isolated as pure compounds (1-5,7, and 10) or unseparable mixtures (5 + 6 and 8 + 9). All compounds were subjected to spectroscopicanalysis and 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide bioassay on MCF-7 humanbreast cancer cells. In addition to the main components oleanolic (1), ursolic (2), and betulinic (3)acids, the 2-hydroxy analogues alphitolic (4), corosolic (5), and maslinic (6) acids, as well as therelated aldehydes, namely, betulinic (7), oleanolic (8), and ursolic (9), were identified. From a morepolar fraction, the -sitosterol 3-O-glucoside (10) was also identified. A sample of commerciallyavailable betulin (11) was also included in bioassays as further support to a structure-activityrelationship study. Betulinic acid showed antiproliferative activity toward MCF-7 cells (GI₅₀ = 0.27M), higher than the anticancer drug 5-fluorouracil.Keywords: Almond hulls; Prunus dulcis sin. amygdalus; terpenoids; antiproliferative; MCF-7 cells;structure-activity relationship study