Identification of triterpene hydroxycinnamates with in vitro antitumor activity from whole cranberry fruit (Vaccinium macrocarpon).
Bioactivity-guided fractionation of cranberry fruit was used to determine the identity of triterpenoid esters from Vaccinium macrocarpon, which inhibit tumor cell growth and may play a role in cancer prevention. In our previous study, a fraction from whole fruit exhibited tumor cell growth inhibition in vitro. The major components of this fraction were isolated by chromatographic separation of ethyl acetate extracts, purified by semipreparative HPLC, and identified by NMR as cis- (1) and trans- (2) isomers of 3-O-p-hydroxycinnamoyl ursolic acid. These triterpenoid esters have not been previously reported in Vaccinium fruit. Bioassay of the purified triterpene cinnamates in tumor cell lines in vitro showed slightly greater activity of compound 1 in most cell lines, with GI(50) values of approximately 20 microM in MCF-7 breast, ME180 cervical and PC3 prostate tumor cell lines. Quercetin was slightly less active than 1, while cyanidin-3-galactoside exhibited much lower cytotoxicity, with GI(50) greater than 250 microM in all cell lines. Phenylboronic acid (3) was also isolated from the fruit but showed insignificant antitumor activity.
Murphy
Brian T
BT
Department of Chemistry and Biochemistry, University of Massachusetts Dartmouth, North Dartmouth 02747, USA.
MacKinnon
Shawna L
SL
Yan
Xiaojun
X
Hammond
Gerald B
GB
Vaisberg
Abraham J
AJ
Neto
Catherine C
CC
D000972:Antineoplastic Agents, Phytogenic / Q000032:analysis* / Q000494:pharmacology; D002455:Cell Division / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003373:Coumaric Acids / Q000032:analysis* / Q000494:pharmacology; D006801:Humans; D066298:In Vitro Techniques; D009682:Magnetic Resonance Spectroscopy; D009369:Neoplasms / Q000517:prevention & control*; D010936:Plant Extracts / Q000032:analysis; D014315:Triterpenes / Q000032:analysis* / Q000737:chemistry / Q000302:isolation & purification; D014407:Tumor Cells, Cultured; D029799:Vaccinium macrocarpon / Q000737:chemistry*
D000972:Antineoplastic Agents, Phytogenic; D003373:Coumaric Acids; D010936:Plant Extracts; D014315:Triterpenes