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.
Publication types
-
Research Support, Non-U.S. Gov't
MeSH terms
-
Antioxidants / chemistry
-
Antioxidants / isolation & purification
-
Antioxidants / pharmacology*
-
Biphenyl Compounds / metabolism
-
Butylated Hydroxytoluene / pharmacology
-
Caffeic Acids / pharmacology
-
Chlorogenic Acid / analogs & derivatives
-
Chlorogenic Acid / chemistry
-
Chlorogenic Acid / isolation & purification
-
Chlorogenic Acid / pharmacology
-
Copper / chemistry
-
Copper / pharmacology
-
Dipsacaceae / chemistry*
-
Dose-Response Relationship, Drug
-
Free Radical Scavengers / chemistry
-
Free Radical Scavengers / isolation & purification
-
Free Radical Scavengers / pharmacology
-
Gallic Acid / analogs & derivatives
-
Gallic Acid / chemistry
-
Gallic Acid / isolation & purification
-
Gallic Acid / pharmacology
-
Humans
-
Hydrazines / metabolism
-
Lipid Peroxidation / drug effects
-
Lipoproteins, LDL / metabolism
-
Malondialdehyde / metabolism
-
Methanol
-
Molecular Structure
-
Monosaccharides / chemistry
-
Monosaccharides / isolation & purification
-
Monosaccharides / pharmacology
-
Picrates
-
Plant Extracts / chemistry
-
Plant Extracts / isolation & purification
-
Plant Extracts / pharmacology
-
Plant Roots / chemistry*
-
Plants, Medicinal / chemistry
-
Quinic Acid / analogs & derivatives*
-
Quinic Acid / chemistry
-
Quinic Acid / isolation & purification
-
Quinic Acid / pharmacology
-
Thiobarbituric Acid Reactive Substances / metabolism
-
alpha-Tocopherol / pharmacology
Substances
-
4,5-di-O-(E)-caffeoylquinic acid
-
Antioxidants
-
Biphenyl Compounds
-
Caffeic Acids
-
Free Radical Scavengers
-
Hydrazines
-
Lipoproteins, LDL
-
Monosaccharides
-
Picrates
-
Plant Extracts
-
Thiobarbituric Acid Reactive Substances
-
caffeoylquinic acid
-
Quinic Acid
-
3,5-di-O-galloyl-4-O-digalloylquinic acid
-
Butylated Hydroxytoluene
-
Chlorogenic Acid
-
Malondialdehyde
-
Gallic Acid
-
Copper
-
1,1-diphenyl-2-picrylhydrazyl
-
3,4-di-O-caffeoylquinic acid
-
alpha-Tocopherol
-
caffeic acid
-
Methanol