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Flavonoid constituents of Chorizanthe diffusa with potential cancer chemopreventive activity
Authors:Chung H S  Chang L C  Lee S K  Shamon L A  van Breemen R B  Mehta R G  Farnsworth N R  Pezzuto J M  Kinghorn A D
Institution:Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, IL 60612, USA.
Abstract:An ethyl acetate-soluble extract of Chorizanthe diffusa was found to exhibit significant antioxidant activity, as judged by scavenging stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals and inhibition of 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced free radical formation with cultured HL-60 cells. Bioassay-directed fractionation of this extract using the DPPH antioxidant assay as a monitor led to the isolation of five structurally related flavonoids (1-5), including the novel compound 5,8,3',4',5'-pentahydroxy-3, 7-dimethoxyflavone (1). Isolates 1-5 demonstrated varying degrees of antioxidant or antimutagenic activity. Two of the compounds, 5,7,3', 4'-tetrahydroxy-3-methoxyflavone (2) and quercetin (4), were subsequently found to inhibit carcinogen-induced preneoplastic lesions in a mouse mammary organ culture model. Inhibitory activity of this type is known to correlate with cancer chemopreventive effects in full-term models of tumorigenesis.
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