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Chlorogenic acid
About: Chlorogenic acid is a research topic. Over the lifetime, 6809 publications have been published within this topic receiving 179379 citations. The topic is also known as: 3-(3,4-Dihydroxycinnamoyl)quinic acid & 3-Caffeoylquinic acid.
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TL;DR: The fragmentation behavior of 18 chlorogenic acids that are not substituted at position 1 has been investigated using LC-MS(4) applied to a methanolic coffee bean extract and commercial cider and these assignments are internally consistent and consistent with the limited data previously available.
Abstract: The fragmentation behavior of 18 chlorogenic acids that are not substituted at position 1 has been investigated using LC-MS(4) applied to a methanolic coffee bean extract and commercial cider (hard cider). Using LC-MS(3), it is possible to discriminate between each of the three isomers of p-coumaroylquinic acid, caffeoylquinic acid, feruloylquinic acid, and dicaffeoylquinic acid, and a hierarchical key has been prepared to facilitate this process when standards are not available. MS(4) fragmentations further support these assignments, but were not essential in reaching them. The distinctive behavior of 4-acyl and 3-acyl chlorogenic acids compared with the 5-acyl chlorogenic acids is a key factor permitting these assignments. The fragmentation patterns are dependent upon the particular stereochemical relationships between the individual substituents on the quinic acid moiety. Fragmentation is facilitated by 1,2-acyl participation and proceeds through quinic acid conformers in which the relevant substituents transiently adopt a 1,3-syn-diaxial relationship. Selected ion monitoring at m/z 529 clearly indicated the presence in coffee of six caffeoylferuloylquinic acid isomers, whereas previously only two or three had been demonstrated. The hierarchical key permitted specific structures to be assigned to each of the six isomers. These assignments are internally consistent and consistent with the limited data previously available.
1,112 citations
TL;DR: In this article, the major antioxidant activity in the non-hydrolyzed extract was caused by flavonol glycosides, chlorogenic acid (7.1 × 10−4 mol/kg of seed) and caffeic acid (6.6 × 10 −3 m/kg).
Abstract: Chia (Salvia sp) seeds were investigated as a source of natural lipid antioxidants. Methanolic and aqueous extracts of defatted chia seeds possessed potent antioxidant activity. Analysis of 2 batches of chia-seed oils demonstrated marked difference in the fatty acid composition of the oils. In both batches, the oils had high concentrations of polyunsaturated fatty acids. The major antioxidant activity in the nonhydrolyzed extract was caused by flavonol glycosides, chlorogenic acid (7.1 × 10−4 mol/kg of seed) and caffeic acid (6.6 × 10−3 m/kg). Major antioxidants of the hydrolyzed extracts were flavonol aglycones/kaempferol (1.1 × 10−3 m/kg), quercetin (2.0 × 10−4 m/kg) and myricetin (3.1 × 10−3 m/kg); and caffeic acid (1.35 × 10−2 m/kg). Two methods were used to measure antioxidant activities. Both were based on measuring bleaching ofβ-carotene in the coupled oxidation ofβ-carotene and linoleic acid in the presence of added antioxidants.
937 citations
TL;DR: In this paper, the authors compared the antioxidative and free radical scavenging activities of caffeic acid compounds with those of α-tocopherol and BHT in the Rancimat test and found that the addition of test compounds in lard significantly extended the induction time of lipid oxidation.
Abstract: Hydroxycinnamic acid compounds are an important source of antioxidants due to their ubiquitous occurrence in the plant kingdom and their characteristic activities. In this study, we compared the antioxidative and free radical scavenging activities of caffeic acid (CA), caffeic acid phenethyl ester (CAPE), ferulic acid (FA), ferulic acid phenethyl ester (FAPE), rosmarinic acid (RA), and chlorogenic acid (CHA) with those of α-tocopherol and BHT. In the Rancimat test, the addition of test compounds in lard significantly extended the induction time of lipid oxidation, and the activities in decreasing order were CA ∼ α-tocopherol > CAPE ∼ RA > CHA ≫ BHT > FA ∼ FAPE. When the lipid substrate was changed to corn oil, the effectiveness of antioxidants on the induction time was obviously decreased, and the potency order of antioxidants was changed to RA > CA ∼ CAPE ∼ CHA > α-tocopherol > BHT; FA and FAPE had no significant antioxidative effect in the corn oil system. The 2,2-diphenyl-1-picrylhydrazyl radical (DPPH...
865 citations
TL;DR: One third of chlorogenic acid and almost all of the caffeic acid were absorbed in the small intestine of humans, which implies that part ofchlorogenic acid from foods will enter into the blood circulation, but most will reach the colon.
Abstract: Chlorogenic acid, an ester of caffeic acid and quinic acid, is a major phenolic compound in coffee; daily intake in coffee drinkers is 0.5-1 g. Chlorogenic acid and caffeic acid are antioxidants in vitro and might therefore contribute to the prevention of cardiovascular disease. However, data on the absorption of chlorogenic acid and caffeic acid in humans are lacking. We determined the absorption of chlorogenic acid and caffeic acid in a cross-over study with 4 female and 3 male healthy ileostomy subjects. In such subjects, degradation by the colonic microflora is minimal and absorption can be calculated as the amount ingested minus the amount excreted in ileostomy effluent. The ileostomy subjects ingested 2.8 mmol chlorogenic acid and 2.8 mmol caffeic acid on separate days in random order and subsequently collected ileostomy fluid and urine for 24 h. Absorption of chlorogenic acid was 33 +/- 17% (mean +/- SD) and of caffeic acid 95 +/- 4%. Traces of the ingested chlorogenic acid and 11% of the ingested caffeic acid were excreted in urine. Thus, one third of chlorogenic acid and almost all of the caffeic acid were absorbed in the small intestine of humans. This implies that part of chlorogenic acid from foods will enter into the blood circulation, but most will reach the colon.
864 citations
TL;DR: Phenolics such as quercetin and cyanidin had highly effective radical scavenging structures in blueberries, cranberry, chokeberry, and lingonberries, and Phenolic acids such as caffeic acid showed high antioxidant activity, probably due to its dihydroxylation in the 3-4 positions as hydrogen donors.
Abstract: The antioxidant activity of phenolics in fruits of blueberry (Vaccinium corymbosum cv. Sierra), cranberry (Vaccinium macrocarpon cv. Ben Lear), wild chokeberry (Aronia melanocarpa), and lingonberry (Vaccinium vitis-idaea cv. Amberland) was determined in this study. The phenolic constituents and contents among the different berries varied considerably. Anthocyanins were found to be the main components in all these berries. Chlorogenic acid in blueberry, quercetin glycosides in cranberry and lingonberry, and caffeic acid and its derivative in chokeberry were also present in relatively high concentrations. Chlorogenic acid, peonidin 3-galactoside, cyanidin 3-galactoside, and cyanidin 3-galactoside were the most important antioxidants in blueberry, cranberry, wild chokeberry, and lingonberry, respectively. The contribution of individual phenolics to the total antioxidant capacity was generally dependent on their structure and content in the berries. Phenolics such as quercetin and cyanidin, with 3',4'-dihydroxy substituents in the B ring and conjugation between the A and B rings, had highly effective radical scavenging structures in blueberries, cranberries, chokeberries, and lingonberries. Phenolic acids such as caffeic acid also showed high antioxidant activity, probably due to its dihydroxylation in the 3,4 positions as hydrogen donors.
801 citations