Dicaffeoylquinic acid ameliorates chronic dermatitis caused by trinitrochlorobenzene

Planta Medica ◽  
2009 ◽  
Vol 75 (09) ◽  
Author(s):  
RM Giner ◽  
M El Alami ◽  
S Máñez
Keyword(s):  
Dicaffeoylquinic Acid

Assessment of Cota altissima (L.) J. Gay for phytochemical composition and antioxidant, anti-inflammatory, antidiabetic and antimicrobial activities

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Gamze Göger ◽  
Muhammed Allak ◽  
Ali Şen ◽  
Fatih Göger ◽  
Mehmet Tekin ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Essential Oil ◽  
Antioxidant Activities ◽  
Antimicrobial Activities ◽  
Antidiabetic Activity ◽  
Gram Negative Bacteria ◽  
Inhibitory Effects ◽  
Dicaffeoylquinic Acid ◽  
Anti Inflammatory ◽  
Phytochemical Profiles

Abstract Phytochemical profiles of essential oil (EO), fatty acids, and n-hexane (CAH), diethyl ether (CAD), ethyl acetate (CAE) and methanol extracts (CAM) of Cota altissima L. J. Gay (syn. Anthemis altissima L.) were investigated as well as their antioxidant, anti-inflammatory, antidiabetic and antimicrobial activites. The essential oil was characterized by the content of acetophenone (35.8%) and β-caryophyllene (10.3%) by GC-MS/FID. Linoleic and oleic acid were found as main fatty acids. The major constituents of the extracts were found to be 5-caffeoylquinic acid, 3,5-dicaffeoylquinic acid, isorhamnetin glucoside, quercetin and quercetin glucoside by LC-MS/MS. Antioxidant activities of the extracts were determined by scavenging of DPPH and ABTS free radicals. Also, the inhibitory effects on lipoxygenase and α-glucosidase enzymes were determined. Antimicrobial activity was evaluated against Gram positive, Gram negative bacteria and yeast pathogens. CAM showed the highest antioxidant activity against DPPH and ABTS radicals with IC50 values of 126.60 and 144.40 μg/mL, respectively. In the anti-inflammatory activity, CAE demonstrated the highest antilipoxygenase activity with an IC50 value of 105.40 μg/mL, whereas, CAD showed the best inhibition of α-glucosidase with an IC50 value of 396.40 μg/mL in the antidiabetic activity. CAH was effective against Staphylococcus aureus at MIC = 312.5 µg/mL. This is the first report on antidiabetic, anti-inflammatory and antimicrobial activities of different extracts of C. altissima.

scholarly journals Quantification of Major Bioactive Constituents, Antioxidant Activity, and Enzyme Inhibitory Effects of Whole Coffee Cherries (Coffea arabica) and Their Extracts

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4306
Author(s):  
Boris Nemzer ◽  
Diganta Kalita ◽  
Nebiyu Abshiru
Keyword(s):  
Antioxidant Activity ◽  
Coffea Arabica ◽  
Digestive Enzymes ◽  
Chlorogenic Acids ◽  
Inhibitory Effects ◽  
Bioactive Constituents ◽  
Caffeoylquinic Acids ◽  
Dicaffeoylquinic Acid ◽  
Ic50 Values ◽  
Control Of Diabetes

Coffee cherry is a rich source of chlorogenic acids (CGAs) and caffeine. In this study we examined the potential antioxidant activity and enzyme inhibitory effects of whole coffee cherries (WCC) and their two extracts on α-amylase, α-glucosidase and acetylcholinesterase (AChE) activities, which are targets for the control of diabetes and Alzheimer’s diseases. Whole coffee cherry extract 40% (WCCE1) is rich in chlorogenic acid compounds, consisting of a minimum of 40% major isomers, namely 3-caffeoylquinic acids, 4-caffeoylquinic acids, 5-caffeoylquinic acids, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, 4-feruloylquinc acid, and 5-feruloylquinc acid. Whole coffee cherry extract 70% (WCCE2) is rich in caffeine, with a minimum of 70%. WCCE1 inhibited the activities of digestive enzymes α-amylase and α-glucosidase, and WCCE2 inhibited acetylcholinesterase activities with their IC50 values of 1.74, 2.42, and 0.09 mg/mL, respectively. Multiple antioxidant assays—including DPPH, ABTS, FRAP, ORAC, HORAC, NORAC, and SORAC—demonstrated that WCCE1 has strong antioxidant activity.

scholarly journals Phenolic Constituents of Knautia arvensis Aerial Parts

2011 ◽  
Vol 6 (11) ◽  
pp. 1934578X1100601 ◽  
Author(s):  
Jaroslaw Moldoch ◽  
Barbara Szajwaj ◽  
Milena Masullo ◽  
Lukasz Pecio ◽  
Wieslaw Oleszek ◽  
...  
Keyword(s):  
Chlorogenic Acid ◽  
2D Nmr ◽  
Spectroscopic Methods ◽  
Flavone Glycoside ◽  
Aerial Parts ◽  
Dicaffeoylquinic Acid ◽  
Phenolic Constituents ◽  
First Time

A new C-6 flavone glycoside (6), together with seven known compounds, cryptochlorogenic acid (1), chlorogenic acid (2), 2- O- trans-caffeoylhydrocitric acid (3), isovitexin 7-β-D-glucopyranoside (4), 7,4′-dihydroxy-5-methoxyflavone-6- C-β-D-glucopyranoside (5), 3,5- O-dicaffeoylquinic acid (7) and 4,5- O-dicaffeoylquinic acid (8), were isolated from the aerial parts of Knautia arvensis. Their structures were elucidated by extensive spectroscopic methods including 1D- (1H, 13C and TOCSY) and 2D-NMR (DQF-COSY, HSQC, HMBC) experiments, as well as ESIMS analysis. Compounds 1, 3-5 and 8 are reported for the first time in Knautia arvensis.

scholarly journals Anti-austeric Activity of Phenolic Constituents of Seeds of Arctium lappa

2013 ◽  
Vol 8 (4) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Yasuhiro Tezuka ◽  
Keiichi Yamamoto ◽  
Suresh Awale ◽  
Feng Li ◽  
Satoshi Yomoda ◽  
...  
Keyword(s):  
Pancreatic Cancer ◽  
Cytotoxic Activity ◽  
Chlorogenic Acid ◽  
Human Pancreatic Cancer ◽  
Arctium Lappa ◽  
Dicaffeoylquinic Acid ◽  
Phenolic Constituents ◽  
Pure Compounds ◽  
F 14

From seeds of Arctium lappa L. (Asteraceae) we obtained arctigenin (1), arctiin (2), chlorogenic acid (3), 4,5-dicaffeoylquinic acid (4), 3,5-dicaffeoylquinic acid (5), 3,4-dicaffeoylquinic acid (6), matairesinol (11), isolappaol A (12), lappaol F (14), and lappaol B (15), together with 1:1 mixtures of isolappaol C (7) and lappaol C (8), arctignan E (9) and arctignan D (10), and 12 and lappaol A (13), while 3,3′,4′-tri- O-demethylarctigenin (16), 3,3′-di- O-demethyl-4′-dehydroxyarctigenin (17), and 3- O-demethylarctigenin (18) were obtained by anaerobic microbiological metabolism of 1. Then, we evaluated the in vitro preferential cytotoxic activity of these pure compounds and 1:1 mixtures, together with enterodiol (19) and enterolactone (20), against human pancreatic cancer PANC-1 cells in nutrient-deprived medium (NDM). Among them, 1 and 18 showed potent activity, with PC50 values of 1.75 and 4.38 μ M, respectively, while 11, 15, and 17 showed mild activity with PC50 values of 31.1, 30.9, and 38.7 μ/M, respectively. By comparing their structures and PC50 values, the following structural moieties could be concluded to be important for the preferential cytotoxicity of 1: 1) the 3-hydroxy-4-methoxyphenyl group at the 2-position on the γ-butyrolactone ring, 2) the less polar substituent at the 3-position on the γ-butyrolactone ring, and 3) the γ-butyrolactone ring.

Simultaneous determination of 1,3-dicaffeoylquinic acid and caffeic acid in rat plasma by liquid chromatography/tandem mass spectrometry and its application to a pharmacokinetic study

2015 ◽  
Vol 7 (8) ◽  
pp. 3587-3592 ◽  
Author(s):  
Guoliang Dai ◽  
Shitang Ma ◽  
Bingting Sun ◽  
Tao Gong ◽  
Shijia Liu ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Liquid Chromatography ◽  
Plasma Concentration ◽  
Rat Plasma ◽  
Tandem Mass ◽  
Concentration Time ◽  
Chromatography Tandem Mass Spectrometry ◽  
Dicaffeoylquinic Acid ◽  
Liquid Chromatography Tandem Mass

The figure shows the average plasma concentration–time curves after an intravenous administration of 4 mL kg−1 Dengzhanxixin injection to rats.

scholarly journals The Effect of Geometrical Isomerism of 3,5-Dicaffeoylquinic Acid on Its Binding Affinity to HIV-Integrase Enzyme: A Molecular Docking Study

2016 ◽  
Vol 2016 ◽  
pp. 1-9 ◽  
Author(s):  
Mpho M. Makola ◽  
Ian A. Dubery ◽  
Gerrit Koorsen ◽  
Paul A. Steenkamp ◽  
Mwadham M. Kabanda ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Density Functional ◽  
Catalytic Domain ◽  
Synergistic Activity ◽  
Hiv Integrase ◽  
Molecular Docking Study ◽  
Geometrical Isomers ◽  
Catalytic Core ◽  
Dicaffeoylquinic Acid ◽  
Hiv 1

A potent plant-derived HIV-1 inhibitor, 3,5-dicaffeoylquinic acid (diCQA), has been shown to undergo isomerisation upon UV exposure where the naturally occurring3trans,5trans-diCQA isomer gives rise to the3cis,5trans-diCQA,3trans,5cis-diCQA, and3cis,5cis-diCQA isomers. In this study, inhibition of HIV-1 INT by UV-induced isomers was investigated using molecular docking methods. Here, density functional theory (DFT) models were used for geometry optimization of the 3,5-diCQA isomers. The YASARA and Autodock VINA software packages were then used to determine the binding interactions between the HIV-1 INT catalytic domain and the 3,5-diCQA isomers and the Discovery Studio suite was used to visualise the interactions between the isomers and the protein. The geometrical isomers of 3,5-diCQA were all found to bind to the catalytic core domain of the INT enzyme. Moreover, thecisgeometrical isomers were found to interact with the metal cofactor of HIV-1INT, a phenomenon which has been linked to antiviral potency. Furthermore, the3trans,5cis-diCQA isomer was also found to interact with both LYS156 and LYS159 which are important residues for viral DNA integration. The differences in binding modes of these naturally coexisting isomers may allow wider synergistic activity which may be beneficial in comparison to the activities of each individual isomer.

Caffeoyl Quinic and Tartaric Acids and Flavonoids from Lapsana communis L. subsp. communis (Asteraceae)

1998 ◽  
Vol 53 (11-12) ◽  
pp. 1090-1092 ◽  
Author(s):  
D. Fontanel ◽  
C. Galtier ◽  
C. Viel ◽  
A. Gueiffier
Keyword(s):  
Chlorogenic Acid ◽  
Caffeic Acid ◽  
Hydroxycinnamic Acids ◽  
First Report ◽  
Chicoric Acid ◽  
Caftaric Acid ◽  
Aerial Parts ◽  
Tartaric Acids ◽  
Dicaffeoylquinic Acid

Abstract Six hydroxycinnamic acids : caffeic acid, chlorogenic acid, 3,5-O-dicaffeoylquinic acid 2-O-caffeoyltartaric acid (caftaric acid) and 2,3-O-dicaffeoyltartaric acid (chicoric acid) have been isolated from Lapsana communis L. subsp. communis aerial parts. Among flavonoids, only isoquercitrin, luteolin and luteolin-7-O-β-glucuronide were identified. Except for chlorogenic acid, these com­ pounds represent the first report in Lapsana communis. Chicoric acid is the major phenylpropanoic constituent in this plant.

Bioactivity of allelochemicals isolated from the roots of Echinacea purpurea L. Moench on Amaranthus viridis L., Portulaca oleracea L. and Microcystis aeruginosa

2021 ◽  
Vol 52 (1) ◽  
pp. 119-130
Author(s):  
Xiao Jing-Lei ◽  
Zhang Yan-Xin ◽  
Jia Cheng-Guo ◽  
Zhang Ming-Zhe ◽  
Chen Wei ◽  
...  
Keyword(s):  
Microcystis Aeruginosa ◽  
Echinacea Purpurea ◽  
Shoot Length ◽  
Portulaca Oleracea ◽  
Algicidal Activity ◽  
Ionization Mass ◽  
Cichoric Acid ◽  
Compound I ◽  
Dicaffeoylquinic Acid ◽  
Compound Ii

Based on the bioassay-guided strategy, we isolated 6-six allelochemicals [cichoric acid (I), 1,3-dicaffeoylquinic acid (II), 4,5-dicaffeoylquinic acid (III), chlorogenic acid (IV), 1-hydroxy-2-phthoic acid (V), echinacoside (VI)] from the roots of Echinacea purpurea (L.) Moench. Their structures were identified by nuclear magnetic resonance (NMR) and electrospray ionization mass spectrometry (ESI-MS) spectroscopic data. The bioassays studies included allelopathic and algicidal activities to test the effects of extracts and isolated fractions against the test weeds (Amaranthus viridis L., Portulaca oleracea L. and Microcystis aeruginosa Kutzing). At 100 µg/mL, compound (II) inhibited the shoot length and germination of A. viridis and P. oleracea weeds with the germination RI of -0.95±0.04 and -0.95±0.02, respectively. Furthermore, compound (III) showed the strongest inhibition of root length of P. oleracea L. We also found that compounds I-VI have algicidal activity. The compound (I) at low inoculum (5.0×102 cells mL-1) and high inoculum (1.0×104 cells mL-1), showed the highest algicidal activity of 78 % and 87.67 % 6 h after the treatment at 5 µg mL-1 respectively.

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