chicoric-acid and caftaric-acid

Medicinal plants are widely used for the relief of disease symptoms or as dietary supplements. In recent decades, purple coneflower has become extremely well known. An infusion or tincture of purple coneflower can be prepared by anyone simply, inexpensively, and ecologically safely. Three plant parts of purple coneflower were used in the study: extracts from roots, flowers, and leaves were obtained using three different solvents (100% and 40% ethanol and water). High-performance liquid chromatography-mass spectrophotometer identified and quantified 23 individual phenolics. Pure (100%) ethanol gave the lowest yield of all the investigated phenolic compounds in all herb parts. Chicoric and caftaric acids were the major phenolic compounds in coneflower. Caftaric acid, with health promoting properties, was extracted best in a water solution from purple coneflower leaves (2673.31 mg/100 g dry weight [DW]) and chicoric acid, also with a beneficial effect on human health, yielded the highest levels in 40% ethanol solution from flowers (1571.79 mg/100 g DW) and roots (1396.27 mg/100 g DW).

Topics: Caffeic Acids; Chemistry, Pharmaceutical; Chromatography, High Pressure Liquid; Echinacea; Flowers; Humans; Phenols; Phytotherapy; Plant Extracts; Plant Leaves; Plant Roots; Succinates; Teas, Herbal

The Cretan diet, as the basis of the Mediterranean diet, has provided traditional remedies for the general well being of people through the long-established consumption of cooked wild greens and vegetables. The intake of the water decoctions of Cichorium spinosum and Cichorium intybus in the context of the daily dietary regime in Greece has been long associated with "liver detoxifying" properties. In the current study, we performed an in-depth investigation of the water decoctions traditionally prepared from C. spinosum and C. intybus through qualitative UHPLC-HRMS profiling and direct quantification of cichoric and caftaric acid as major antioxidant components of the decoction. In addition, we developed a one-step countercurrent chromatography method for the isolation of the two phenolic acids, along with a sulfoconjugate sesquiterpene lactone present only in the Cretan C. spinosum. All water decoctions were found not to be cytotoxic in human fibroblasts, whereas they all significantly reduced the intracellular reactive oxygen species, which is consistent with the major presence of strong antioxidant compounds such as cichoric acid. This work demonstrates that the intake of these decoctions in doses suggested by Greek traditional use is comparable to the ingestion of a phytomedical preparation of antioxidants. These results contribute to our current knowledge on the beneficial health effect of the Cretan diet.

Topics: Antioxidants; Asteraceae; Caffeic Acids; Cell Line; Chromatography, High Pressure Liquid; Cichorium intybus; Diet, Mediterranean; Humans; Mass Spectrometry; Molecular Structure; Phenols; Phytochemicals; Plant Extracts; Succinates

Chicoric acid has recently become a hot research topic due to its potent bioactivities. However, there are few studies relevant to this acid's pharmacokinetic characteristics and the pharmacological activities of its metabolites. To compare the abilities of chicoric acid and its metabolites in scavenging free radicals and their effects on the viability of 3T3-L1 preadipocytes, an in vitro study of the metabolism of chicoric acid in rat liver microsomes was performed using liquid tandem mass spectrometry (HPLC-MS/MS). The results indicated that caffeic acid and caftaric acid were the hepatic phase I metabolites of chicoric acid. These three compounds had strong capacities for scavenging free radicals and had been demonstrated to increase intracellular ROS levels in 3T3-L1 preadipocytes, thereby reducing cell vitality. Finally, the pharmacological activities of chicoric acid were significantly stronger than those of its metabolites within a certain concentration range.

Topics: 3T3-L1 Cells; Adipocytes; Animals; Anti-Obesity Agents; Antioxidants; Caffeic Acids; Cell Survival; Chromatography, High Pressure Liquid; Free Radical Scavengers; Kinetics; Metabolic Detoxication, Phase I; Mice; Microsomes, Liver; Molecular Structure; Phenols; Rats; Reactive Oxygen Species; Spectrometry, Mass, Electrospray Ionization; Succinates; Tandem Mass Spectrometry

The study objective was to evaluate the composition of a neutral and weakly acidic water-soluble extract from Echinacea purpurea (L.) Moench (EchNWA) previously shown to modify murine influenza infection, and to assess immunomodulatory effects on human T-cells. EchNWA extract from fresh aerial parts was extracted with water, ethanolic precipitation, and size-exclusion chromatography. The chemical profile of EchNWA was characterized by chromatography (size-exclusion, HPLC, GC-MS), and small molecule fingerprint analysis performed by HPLC-PDA. Jurkat T-cells at high and low cell density were pretreated or not with doses of EchNWA, followed by activation with phorbol 12-myristate 13-acetate plus ionomycin (PMA+I). Interleukin-2 (IL-2) and interferon gamma (IFNg) cytokine secretions were measured by multi-cytokine luminex technology. Results showed that EchNWA contains 80% polysaccharides, predominantly a 10kDa entity; phenolic compounds, cynarin, cichoric and caftaric acids, but no detectable alkylamides. Cytokine production required stimulation and was lower after PMA+I activation in high-density compared to low-density conditions. EchNWA mediated a strong dose-dependent enhancement of high-density T-cell production of IL-2 and IFNg response to PMA+I. EchNWA alone did not stimulate T-cells. EchNWA enhanced mean fluorescence intensity of IL-2 in Jurkat T-cells activated by PMA+1 or ionomycin alone. Conversely EchNWA mediated modest but significant suppression of IFNg response and reduced the percentage of CD25+ T-cells under low-density conditions. Conclusions are that EchNWA polysaccharides, but not phenolic compounds have dose-related adjuvant effects on human T-cell cytokine responses characterized by enhancing and suppressive effects that are regulated by T-cell density.

Topics: Caffeic Acids; Cytokines; Echinacea; Humans; Immunologic Factors; Jurkat Cells; Monosaccharides; Phenols; Plant Extracts; Polysaccharides; Succinates; T-Lymphocytes

To investigate effects of different postharvest drying processes and storage conditions on key antioxidants in Sonchus oleraceus L. leaves.. Fresh leaves were oven-dried (60°C), freeze-dried or air-dried (∼25°C) for 6 h, 24 h and 3 days, respectively. Design of experiments (DOE) was applied to study the stability of antioxidants (caftaric, chlorogenic and chicoric acids) in S. oleraceus leaves and leaf extracts stored at different temperatures (4, 25 and 50°C) and relative humidities (15%, 43% and 75%) for 180 days. The concentration of antioxidants was quantified by a HPLC-2,2'-diphenylpicrylhydrazyl post-column derivatisation method. Antioxidant activity was assessed by a cellular antioxidant activity assay.. The three antioxidants degraded to unquantifiable levels after oven-drying. More than 90% of the antioxidants were retained by freeze-drying and air-drying. Both leaf and extract samples retained >90% of antioxidants, except those stored at 75% relative humidity. Leaf material had higher antioxidant concentrations and greater cellular antioxidant activity than corresponding extract samples.. Freeze-drying and air-drying preserved more antioxidants in S. oleraceus than oven-drying. From DOE analysis, humidity plays an important role in degradation of antioxidants during storage. To preserve antioxidant activity, it is preferable to store S. oleraceus as dried leaf material.

Topics: Antioxidants; Caffeic Acids; Chlorogenic Acid; Desiccation; Drug Stability; Drug Storage; Freeze Drying; Humans; Humidity; Phenols; Plant Extracts; Plant Leaves; Sonchus; Succinates; Temperature

To use an online assay to identify key antioxidants in Sonchus oleraceus leaf extracts and to investigate the effect of leaf position and extraction conditions on antioxidant concentration and activity.. Separation of phytochemicals and simultaneous assessment of antioxidant activity were performed online using HPLC and post-column reaction with a free-radical reagent (2, 2-diphenylpicrylhydrazyl, DPPH). Active compounds were identified using nuclear magnetic resonance spectroscopy and mass spectrometry. We applied the online HPLC-DPPH radical assay to evaluate antioxidants in leaves from different positions on the plant and to assess the effect of pre-treatment of leaves with liquid N(2) before grinding, extraction time, extraction temperature and method of concentrating extracts.. Key antioxidants identified in S. oleraceus leaf extracts were caftaric acid, chlorogenic acid and chicoric acid. Middle leaves contained the highest total amount of the three key antioxidant compounds, consisting mainly of chicoric acid. Pre-treatment with liquid N(2), increasing the extraction temperature and time and freeze-drying the extract did not enhance the yield of the key antioxidants.. The online HPLC-DPPH radical assay was validated as a useful screening tool for investigating individual antioxidants in leaf extracts. Optimized extraction conditions were middle leaves pre-treated with liquid N(2), extraction at 25°C for 0.5 h and solvent removal by rotary evaporation.

Topics: Antioxidants; Biphenyl Compounds; Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Free Radicals; Online Systems; Phenols; Picrates; Plant Extracts; Plant Leaves; Solvents; Sonchus; Succinates

Chicoric acid (ChA) and caftaric acid (CafA) were identified as bioactive components of chicory and have been ascribed a number of health benefits. This study investigated the hydrolysis of ChA and CafA with enzymes and a probiotic bacterium Lactobacillus johnsonii (La1). Esterase from Aspergillus japonicus (24 U/mg) hydrolyzed 100% of ChA (5 mM) and CafA (5 mM) after 3 h, at pH 7.0 and 37 °C. Under the same reaction conditions, 100% hydrolysis of ChA and CafA was achieved with a spray-dried preparation of La1. The addition of La1 (100 mg/mL, 3.3 E9 cfu/g) to CafA solution in a gastrointestinal model (GI model) resulted in 65% hydrolysis of CafA. This model simulates the physicochemical conditions of the human gastrointestinal tract. No hydrolysis of CafA was observed after passage through the GI model in the absence of La1. The results of this study support the hypothesis that ChA and CafA are degraded by gut microflora before absorption and metabolization.

Topics: Aspergillus; Caffeic Acids; Cichorium intybus; Esterases; Fungal Proteins; Gastrointestinal Tract; Humans; Kinetics; Lactobacillus; Models, Biological; Phenols; Probiotics; Succinates

Roots of Echinacea purpurea and Echinacea pallida cultivated for 4 years in a North European climate were analyzed for seasonal variations in the concentrations of lipophilic constituents (alkamides, ketoalkenes, and ketoalkynes) and phenolic acids by harvesting five times during 1 year to establish the optimal time for harvest. A total of 16 alkamides, three ketoalkenes, two ketoalkynes, and four phenolic acids (echinacoside, cichoric acid, caftaric acid, and chlorogenic acid) were identified in aqueous ethanolic (70%) extracts by liquid chromatography-mass spectrometry and quantified by reverse-phase high-performance liquid chromatography. The major alkamides in the roots of E. purpurea were at their lowest concentration in the middle of autumn and early winter, and the total concentration of lipophilic compounds in E. pallida showed the same pattern. Moreover, all of the major phenolic acids in E. purpurea were at their highest concentrations in spring. The optimal harvest time in spring is in contrast to normal growing guidelines; hence, this specific information of seasonal variations in the concentrations of lipophilic and phenolic compounds in E. purpurea and E. pallida is valuable for research, farmers, and producers of medicinal preparations.

Topics: Alkenes; Alkynes; Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Echinacea; Glycosides; Hydroxybenzoates; Phenols; Plant Extracts; Plant Roots; Seasons; Succinates

Stromelysin-1 (matrix metalloproteinase-3: MMP-3) occupies a central position in collagenolytic and elastolytic cascades, leading to cutaneous intrinsic and extrinsic aging. We screened extracts of a propolis sample from Algeria with the aim to isolate compounds able to selectively inhibit this enzyme. A butanolic extract (B (3)) of the investigated propolis sample was found to potently inhibit MMP-3 activity (IC (50) = 0.15 ± 0.03 µg/mL), with no or only weak activity on other MMPs. This fraction also inhibited plasmin amidolytic activity (IC (50) = 0.05 µg/mL) and impeded plasmin-mediated proMMP-3 activation. B (3) was fractionated by HPLC, and one compound, characterized by NMR and mass spectroscopy and not previously identified in propolis, i.e., (+)-chicoric acid, displayed potent IN VITRO MMP-3 inhibitory activity (IC (50) = 6.3 × 10 (-7) M). In addition, both caffeic acid and (+)-chicoric acid methyl ester present in fraction B (3) significantly inhibited UVA-mediated MMP-3 upregulation by fibroblasts.

Topics: Adult; Algeria; Butanols; Caffeic Acids; Cells, Cultured; Chromatography, High Pressure Liquid; Complex Mixtures; Drug Evaluation, Preclinical; Enzyme Activation; Fibrinolysin; Fibroblasts; Humans; Inhibitory Concentration 50; Magnetic Resonance Spectroscopy; Matrix Metalloproteinase 3; Matrix Metalloproteinase Inhibitors; Middle Aged; Phenols; Propolis; Protease Inhibitors; Succinates; Ultraviolet Rays; Young Adult

A new mechanistic class of BoNT/A zinc metalloprotease inhibitors, from Echinacea, exemplified by the natural product d-chicoric acid (I1) is disclosed. A detailed evaluation of chicoric acid's mechanism of inhibition reveals that the inhibitor binds to an exosite, displays noncompetitive partial inhibition, and is synergistic with a competitive active site inhibitor when used in combination. Other components found in Echinacea, I3 and I4, were also inhibitors of the protease.

Topics: Biological Factors; Botulinum Toxins, Type A; Caffeic Acids; Chlorogenic Acid; Clostridium botulinum; Hydroxamic Acids; Molecular Conformation; Phenols; Protease Inhibitors; Stereoisomerism; Structure-Activity Relationship; Succinates

In this Letter, we report the natural products salvianolic acid A, salvianolic acid B, and caftaric acid as inhibitors of the protein-protein interactions mediated by the SH2 domains of the Src-family kinases Src and Lck, two established disease targets. Moreover, we propose a binding mode for the inhibitors based on molecular modeling, which will facilitate chemical optimization efforts of these important lead structures for drug discovery.

Topics: Benzofurans; Biological Products; Caffeic Acids; Drug Discovery; Humans; Lactates; Lymphocyte Specific Protein Tyrosine Kinase p56(lck); Models, Molecular; Phenols; Protein Binding; Protein Kinase Inhibitors; Proto-Oncogene Proteins pp60(c-src); src Homology Domains; src-Family Kinases

Adventitious roots of Echinacea purpurea were cultured in airlift bioreactors (20 l, 500 l balloon-type, bubble bioreactors and 1,000 l drum-type bubble bioreactor) using Murashige and Skoog (MS) medium with 2 mg indole butyric acid l(-1) and 50 g sucrose l(-1) for the production of chichoric acid, chlorogenic acid and caftaric acid. In the 20 l bioreactor (containing 14 l MS medium) a maximum yield of 11 g dry biomass l(-1) was achieved after 60 days. However, the amount of total phenolics (57 mg g(-1) DW), flavonoids (34 mg g(-1) DW) and caffeic acid derivatives (38 mg g(-1) DW) were highest after 50 days. Based on these studies, pilot-scale cultures were established and 3.6 kg and 5.1 kg dry biomass were achieved in the 500 l and 1,000 l bioreactors, respectively. The accumulation of 5 mg chlorogenic acid g(-1) DW, 22 mg chichoric acid g(-1) DW and 4 mg caftaric acids g(-1) DW were achieved with adventitious roots grown in 1,000 l bioreactors.

Topics: Biomass; Bioreactors; Biotechnology; Caffeic Acids; Cell Culture Techniques; Chlorogenic Acid; Echinacea; Models, Biological; Phenol; Phenols; Plant Extracts; Plant Roots; Succinates; Time Factors