Chicoric acid: chemistry, distribution, and production

Lee, Jungmin; Scagel, Carolyn F.

doi:10.3389/fchem.2013.00040

Cited by 124 publications

(85 citation statements)

References 154 publications

(249 reference statements)

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“…Kour and Bani demonstrated that ChA has a protective effect on chronic restraint stress . Recently, ChA has been shown to have anti‐cancer, anti‐obesity, and anti‐diabetic properties . A significant reduction in acute alcohol‐induced steatosis was observed on oral intake of chicoric acid in mice through interfering with inducible nitric oxide synthase (iNOS) in the liver .…”

Section: Introductionsupporting

confidence: 86%

Mechanism of Chicoric Acid Electrochemical Oxidation and Identification of Oxidation Products by Liquid Chromatography and Mass Spectrometry

2016

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Electrochemical oxidation of chicoric acid (ChA) was investigated using cyclic voltammetry and chronoamperometry at a glassy carbon electrode. Chicoric acid generates single quasi‐reversible redox wave in cyclic voltammetry over a wide pH range, and an ECEC‐dimerization mechanism is proposed. Effect of glutathione (GSH) on the electrochemical oxidation of chicoric acid (ChA) was investigated in Britton−Robinson buffer solution. Ultra‐high performance liquid chromatography (UPLC) coupled with mass spectrometry (MS) was used to show that the naturally occurring chicoric acid (ChA) underwent an electrochemical oxidation in the presence of glutathione (GSH) to form mono‐, bi‐, tri‐, and four‐glutathione conjugates of chicoric acid and a mono‐glutathione conjugate of a chicoric acid dimer. The obtained results are useful for understanding and predicting the oxidative degradation pathway of chicoric acid.

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Section: Introductionsupporting

confidence: 86%

Mechanism of Chicoric Acid Electrochemical Oxidation and Identification of Oxidation Products by Liquid Chromatography and Mass Spectrometry

2016

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“…This metabolite has been proposed as an indicator compound for quality control due to its instability and rapid degradation when compared to other secondary metabolites within plant materials [9, 18]. Enhancement due to the incorporation of methanol as a cosolvent during PHWE can be associated with interactions based on polarity.…”

Section: Resultsmentioning

confidence: 99%

The effect of temperature and methanol–water mixture on pressurized hot water extraction (PHWE) of anti-HIV analogoues from Bidens pilosa

Gbashi

Njobeh

Steenkamp

et al. 2016

Chemistry Central Journal

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BackgroundPressurized hot water extraction (PHWE) technique has recently gain much attention for the extraction of biologically active compounds from plant tissues for analytical purposes, due to the limited use of organic solvents, its cost-effectiveness, ease-of-use and efficiency. An increase in temperature results in higher yields, however, issues with degradation of some metabolites (e.g. tartrate esters) when PHWE is conditioned at elevated temperatures has greatly limited its use. In this study, we considered possibilities of optimizing PHWE of some specific functional metabolites from Bidens pilosa using solvent compositions of 0, 20, 40 and 60 % methanol and a temperature profile of 50, 100 and 150 °C.ResultsThe extracts obtained were analyzed using UPLC-qTOF-MS/MS and the results showed that both temperature and solvent composition were critical for efficient recovery of target metabolites, i.e., dicaffeoylquinic acid (diCQA) and chicoric acid (CA), which are known to possess anti-HIV properties. It was also possible to extract different isomers (possibly cis-geometrical isomers) of these molecules. Significantly differential (p ≤ 0.05) recovery patterns corresponding to the extraction conditions were observed as recovery increased with increase in methanol composition as well as temperature. The major compounds recovered in descending order were 3,5-diCQA with relative peak intensity of 204.23 ± 3.16 extracted at 50 °C and 60 % methanol; chicoric acid (141.00 ± 3.55) at 50 °C and 60 % methanol; 4,5-diCQA (108.05 ± 4.76) at 150 °C and 0 % methanol; 3,4-diCQA (53.04 ± 13.49) at 150 °C and 0 % methanol; chicoric acid isomer (40.01 ± 1.14) at 150 °C and 20 % methanol; and cis-3,5-diCQA (12.07 ± 5.54) at 100 °C and 60 % methanol. Fitting the central composite design response surface model to our data generated models that fit the data well with R2 values ranging from 0.57 to 0.87. Accordingly, it was possible to observe on the response surface plots the effects of temperature and solvent composition on the recovery patterns of these metabolites as well as to establish the optimum extraction conditions. Furthermore, the pareto charts revealed that methanol composition had a stronger effect on extraction yield than temperature.ConclusionUsing methanol as a co-solvent resulted in significantly higher (p ≤ 0.05) even at temperatures as low as 50 °C, thus undermining the limitation of thermal degradation at higher temperatures during PHWE.

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“…It has been reported that chicoric acid possesses various functional properties including antioxidant, antivirus and immunoregulation. [28,29] Particularly, chicoric acid is a potent inhibitor of the integrase of the Type 1 human immunodeficiency virus (HIV-1). [30] Additionally, Lee and Scagel [28] indicated that chicoric acid helps a plant protect itself from insects and infection from viruses, bacteria, fungi, and nematodes and that it aids in wound healing in plants after mechanical damage.…”

Section: Rp-hplc Analysis Of Phenolic Compoundsmentioning

confidence: 99%

Antioxidant Sources from Leaves of Russian Dandelion

Molinu

Piluzza

Campesi

et al. 2019

Chemistry & Biodiversity

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Taraxacum kok‐saghyz (TKS) is a dandelion species native to Kazakhstan, Uzbekistan and north‐west China, considered as a promising alternative source of natural rubber from its roots. The aim of this study was to investigate the possible exploitation of TKS leaves, a rubber byproduct, as a source of phenolic compounds with antioxidant properties for potential applications in forage, nutraceutical and pharmacological fields. Two accessions (TKS016, TKS018) grown under Mediterranean conditions of Sardinia were evaluated at vegetative and flowering stages. The leaves of TKS018 had the highest antioxidant capacity (19.6 mmol trolox equivalent antioxidant capacity 100 g−1), total phenolic (106.4 g gallic acid equivalent kg−1), tannic phenolics (58.5 g gallic acid equivalent kg−1) and total flavonoid contents (22.9 g catechin equivalent kg−1). At both phenological stages, TKS016 showed significantly lower values than TKS018 in 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH), total phenolic and tannic phenolics. Six individual molecules were identified, namely chlorogenic, cryptochlorogenic, caffeic, sinapic, chicoric and 3,4‐dimethoxycinnamic acids. Chicoric (8.53–10.68 g kg−1 DW) and chlorogenic acids (4.18–7.04 g kg−1 DW) were the most abundant. TKS leaves represent a valuable source of chicoric acid with potential application as antioxidant to be used as herbal medicine and nutrition for production of healthy food/feed.

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Chicoric acid: chemistry, distribution, and production

Cited by 124 publications

References 154 publications

Mechanism of Chicoric Acid Electrochemical Oxidation and Identification of Oxidation Products by Liquid Chromatography and Mass Spectrometry

Mechanism of Chicoric Acid Electrochemical Oxidation and Identification of Oxidation Products by Liquid Chromatography and Mass Spectrometry

The effect of temperature and methanol–water mixture on pressurized hot water extraction (PHWE) of anti-HIV analogoues from Bidens pilosa

Antioxidant Sources from Leaves of Russian Dandelion

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