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

Citation
Mh. Kweon et al., Identification and antioxidant activity of novel chlorogenic acid derivatives from bamboo (Phyllostachys edulis), J AGR FOOD, 49(10), 2001, pp. 4646-4655
Citations number
51
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis
Journal title
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN journal
00218561 → ACNP
Volume
49
Issue
10
Year of publication
2001
Pages
4646 - 4655
Database
ISI
SICI code
0021-8561(200110)49:10<4646:IAAAON>2.0.ZU;2-O
Abstract
One known and two novel antioxidant compounds have been isolated from bambo o (Phyllostachys edulis). The butanol-soluble extract of the ba m-boo leave s was found to have a significant antioxidant activity, as measured by scav enging the stable 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical and the superoxide anion radical (O-2(-)) in the xanthine/xanthine oxidase assay s ystem. Antioxidant activity-directed fractionation of the extract led to th e isolation and characterization of three structural isomeric chlorogenic a cid derivatives: 3-O-(3'-methylcaffeoyl)quinic acid (1), 5-O-caffeoyl-4-met hylquinic acid (2), and 3-O-caffeoyl-1-methylquinic acid (3). Compounds 2 a nd 3 were isolated and characterized for the first time from the natural pr oducts. In the DPPH scavenging assay as well as in the iron-induced rat mic rosomal lipid peroxidation system, compounds 2 (IC50 = 8.8 and 19.2 muM) an d 3 (IC50 = 6.9 and 14.6 muM) showed similar to2-4 times higher antioxidant activity than did chlorogenic acid (IC50 = 12.3 and 28.3 muM) and other re lated hydroxycinnamates such as caffeic acid (IC50 = 13.7 and 25.5 muM) and ferulic acid (IC50 = 36.5 and 56.9 muM). Among the three compounds, compou nd 1 yielded the weakest antioxidant activity, and the DPPH scavenging and lipid peroxidation inhibitory activity (IC50 = 16.0 and 29.8 muM) was lower than those of chlorogenic and caffeic acids. All three compounds exhibited both superoxide scavenging activities and inhibitory effects on xanthine o xidase. Their superoxide anion (O-2(-)) scavenging activities (IC50 = 1, 4. 3 muM; 2, 2.8 muM; and 3, 1.2 muM) were markedly stronger than those of asc orbic acid (IC50 = 56.0 muM), alpha -tocopherol (IC50 > 100 muM), and other test compounds, although their inhibition effects on xanthine oxidase may contribute to the potent scavenging activity. cc-Tocopherol exerted a signi ficant 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 antioxida nts were weakly active (24.8-10.1%) in the suppression of superoxide genera tion.