Antioxidant activity of caffeoyl quinic acid derivatives from the roots of Dipsacus asper Wall.
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.
Hung
Tran Manh
TM
College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
Na
MinKyun
M
Thuong
Phuong Thien
PT
Su
Nguyen Duy
ND
Sok
DaiEun
D
Song
Kyung Sik
KS
Seong
Yeon Hee
YH
Bae
KiHwan
K
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
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