title: Antioxidant activity of caffeoyl quinic acid derivatives from the roots of Dipsacus asper Wall.
abstract: The methanol extract from Dipsacus asper Wall (Dipsacaceae) was found to show antioxidant activity against free radical and Cu(2+)-mediated LDL oxidation. In further study, to identify active constituents from the plant, six caffeoyl quinic acid derivatives: 3,4-di-O-caffeoylquinic acid (1), methyl 3,4-di-O-caffeoyl quinate (2), 3,5-di-O-caffeoylquinic acid (3), methyl 3,5-di-O-caffeoyl quinate (4), 4,5-di-O-caffeoylquinic acid (5) and methyl 4,5-di-O-caffeoyl quinate (6) were isolated. Their structures were identified by spectroscopic methods including 2D-NMR. The isolated compounds, 1-6, were found to be potent scavengers of the free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH), and are more potent than butylated hydroxyl toluene (BHT) used as a positive control. The compounds 1-6 also inhibited Cu(2+)-mediated low-density lipoprotein (LDL) oxidation. They increased the lag time of conjugated dienes formation and inhibited the generation of thiobarbituric acid reactive substances (TBARS) in a dose-dependent manner. These results suggested that Dipsacus asper due to its antioxidant constituents, 1-6, may have a role to play in preventing the development and progression of atherosclerotic disease.
authors.affiliation: College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
authors.forename: Tran Manh
authors.initials: TM
authors.lastname: Hung
authors.forename: MinKyun
authors.initials: M
authors.lastname: Na
authors.forename: Phuong Thien
authors.initials: PT
authors.lastname: Thuong
authors.forename: Nguyen Duy
authors.initials: ND
authors.lastname: Su
authors.forename: DaiEun
authors.initials: D
authors.lastname: Sok
authors.forename: Kyung Sik
authors.initials: KS
authors.lastname: Song
authors.forename: Yeon Hee
authors.initials: YH
authors.lastname: Seong
authors.forename: KiHwan
authors.initials: K
authors.lastname: Bae
mesh_terms: D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000378:metabolism; D002084:Butylated Hydroxytoluene / Q000494:pharmacology; D002109:Caffeic Acids / Q000494:pharmacology; D002726:Chlorogenic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D003300:Copper / Q000737:chemistry / Q000494:pharmacology; D049917:Dipsacaceae / Q000737:chemistry*; D004305:Dose-Response Relationship, Drug; D016166:Free Radical Scavengers / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005707:Gallic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D006834:Hydrazines / Q000378:metabolism; D015227:Lipid Peroxidation / Q000187:drug effects; D008077:Lipoproteins, LDL / Q000378:metabolism; D008315:Malondialdehyde / Q000378:metabolism; D000432:Methanol; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010851:Picrates; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry; D011801:Quinic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D017392:Thiobarbituric Acid Reactive Substances / Q000378:metabolism; D024502:alpha-Tocopherol / Q000494:pharmacology
chemical_list: C500583:4,5-di-O-(E)-caffeoylquinic acid; D000975:Antioxidants; D001713:Biphenyl Compounds; D002109:Caffeic Acids; D016166:Free Radical Scavengers; D006834:Hydrazines; D008077:Lipoproteins, LDL; D009005:Monosaccharides; D010851:Picrates; D010936:Plant Extracts; D017392:Thiobarbituric Acid Reactive Substances; C472707:caffeoylquinic acid; D011801:Quinic Acid; C061725:3,5-di-O-galloyl-4-O-digalloylquinic acid; D002084:Butylated Hydroxytoluene; D002726:Chlorogenic Acid; D008315:Malondialdehyde; D005707:Gallic Acid; D003300:Copper; C004931:1,1-diphenyl-2-picrylhydrazyl; C478100:3,4-di-O-caffeoylquinic acid; D024502:alpha-Tocopherol; C040048:caffeic acid; D000432:Methanol