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Identification and antioxidant activity of novel chlorogenic acid derivatives from bamboo (Phyllostachys edulis)


, : Identification and antioxidant activity of novel chlorogenic acid derivatives from bamboo (Phyllostachys edulis). Journal of Agricultural and Food Chemistry 49(10): 4646-4655

One known and two novel antioxidant compounds have been isolated from bamboo (Phyllostachys edulis). The butanol-soluble extract of the bamboo leaves was found to have a significant antioxidant activity, as measured by scavenging the stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical and the superoxide anion radical (superoxide) in the xanthine/xanthine oxidase assay system. Antioxidant activity-directed fractionation of the extract led to the isolation and characterization of three structural isomeric chlorogenic acid derivatives: 3-O-(3'-methylcaffeoyl)quinic acid (1), 5-O-caffeoyl-4-methylquinic acid (2), and 3-O-caffeoyl-1-methylquinic acid (3). Compounds 2 and 3 were isolated and characterized for the first time from the natural products. In the DPPH scavenging assay as well as in the iron-induced rat microsomal lipid peroxidation system, compounds 2 (IC50 = 8.8 and 19.2 micromolar) and 3 (IC50 = 6.9 and 14.6 micromolar) showed approximately 2-4 times higher antioxidant activity than did chlorogenic acid (IC50 = 12.3 and 28.3 micromolar) and other related hydroxycinnamates such as caffeic acid (IC50 = 13.7 and 25.5 micromolar) and ferulic acid (IC50 = 36.5 and 56.9 micromolar). Among the three compounds, compound 1 yielded the weakest antioxidant activity, and the DPPH scavenging and lipid peroxidation inhibitory activity (IC50 = 16.0 and 29.8 micromolar) was lower than those of chlorogenic and caffeic acids. All three compounds exhibited both superoxide scavenging activities and inhibitory effects on xanthine oxidase. Their superoxide anion (superoxide) scavenging activities (IC50 = 1, 4.3 micromolar; 2, 2.8 micromolar; and 3, 1.2 micromolar) were markedly stronger than those of ascorbic acid (IC50 = 56.0 micromolar), alpha-tocopherol (IC50 > 100 micromolar), and other test compounds, although their inhibition effects on xanthine oxidase may contribute to the potent scavenging activity. alpha-Tocopherol exerted a significant inhibitory effect (65.5% of the control) on superoxide generation in 12-O-tetradecanoylphorbol-13-acetate-induced human promyelocytic leukemia HL-60 cells, and compound 3 showed moderate activity (36.0%). On the other hand, other compounds including 1, 2, chlorogenic acid, and other antioxidants were weakly active (24.8-10.1%) in the suppression of superoxide generation.

US$19.90

PMID: 11600002

DOI: 10.1021/jf010514x


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