ABSTRACT
ATP citrate lyase (ACLY) is a key enzyme in glucolipid metabolism, and abnormally high expression of ACLY occurs in many diseases, including cancers, dyslipidemia and cardiovascular diseases. ACLY inhibitors are prospective treatments for these diseases. However, the scaffolds of ACLY inhibitors are insufficient with weak activity. The discovery of inhibitors with structural novelty and high activity continues to be a research hotpot. Acanthopanax senticosus (Rupr. & Maxim.) Harms is used for cardiovascular disease treatment, from which no ACLY inhibitors have ever been found. In this work, we discovered three novel ACLY inhibitors, and the most potent one was isochlorogenic acid C (ICC) with an IC50 value of 0.14 ± 0.04 µM. We found dicaffeoylquinic acids with ortho-dihydroxyphenyl groups were important features for inhibition by studying ten phenolic acids. We further investigated interactions between the highly active compound ICC and ACLY. Thermal shift assay revealed that ICC could directly bind to ACLY and improve its stability in the heating process. Enzymatic kinetic studies indicated ICC was a noncompetitive inhibitor of ACLY. Our work discovered novel ACLY inhibitors, provided valuable structure-activity patterns and deepened knowledge on the interactions between this targe tand its inhibitors.
Subject(s)
ATP Citrate (pro-S)-Lyase , Eleutherococcus , Eleutherococcus/chemistry , Molecular Structure , ATP Citrate (pro-S)-Lyase/antagonists & inhibitors , Enzyme Inhibitors/pharmacology , Enzyme Inhibitors/isolation & purification , Enzyme Inhibitors/chemistry , Chlorogenic Acid/pharmacology , Chlorogenic Acid/isolation & purification , Chlorogenic Acid/chemistry , Phytochemicals/pharmacology , Phytochemicals/isolation & purification , Phytochemicals/chemistry , Quinic Acid/analogs & derivatives , Quinic Acid/pharmacology , Quinic Acid/isolation & purification , Quinic Acid/chemistry , Hydroxybenzoates/pharmacology , Hydroxybenzoates/isolation & purification , Hydroxybenzoates/chemistry , Structure-Activity RelationshipABSTRACT
Developing novel strategies for defeating osteoporosis has become a world-wide challenge with the aging of the population. In this work, novel supramolecular nanoagonists (NAs), constructed from alkaloids and phenolic acids, emerge as a carrier-free nanotherapy for efficacious osteoporosis treatment. These precision nanoagonists are formed through the self-assembly of berberine (BER) and chlorogenic acid (CGA), utilizing noncovalent electrostatic, π-π, and hydrophobic interactions. This assembly results in a 100% drug loading capacity and stable nanostructure. Furthermore, the resulting weights and proportions of CGA and BER within the NAs are meticulously controlled with strong consistency when the CGA/BER assembly feed ratio is altered from 1:1 to 1:4. As anticipated, our NAs themselves could passively target osteoporotic bone tissues following prolonged blood circulation, modulate Wnt signaling, regulate osteogenic differentiation, and ameliorate bone loss in ovariectomy-induced osteoporotic mice. We hope this work will open a new strategy to design efficient herbal-derived Wnt NAs for dealing with intractable osteoporosis.
Subject(s)
Berberine , Chlorogenic Acid , Osteoporosis , Osteoporosis/drug therapy , Animals , Mice , Berberine/pharmacology , Berberine/therapeutic use , Berberine/chemistry , Berberine/administration & dosage , Berberine/pharmacokinetics , Chlorogenic Acid/chemistry , Chlorogenic Acid/pharmacology , Chlorogenic Acid/therapeutic use , Chlorogenic Acid/administration & dosage , Female , Humans , Osteogenesis/drug effects , Bone and Bones/drug effects , Bone and Bones/pathology , Nanostructures/chemistry , Nanostructures/therapeutic useABSTRACT
Ulcerative colitis (UC) is a multifactorial disorder of the large intestine, especially the colon, and has become a challenge globally. Allopathic medicines are primarily available for the treatment and prevention of UC. However, their uses are limited due to several side effects. Hence, an alternative therapy is of utmost importance in this regard. Herbal medicines are considered safe and effective for managing human health problems. Chlorogenic acid (CGA), the herbal-derived bioactive, has been reported for pharmacological effects like antiinflammatory, immunomodulatory, antimicrobial, hepatoprotective, antioxidant, anticancer, etc. This review aims to understand the antiinflammatory and chemopreventive potential of CGA against UC. Apart from its excellent therapeutic potential, it has been associated with low absorption and poor oral bioavailability. In this context, colon-specific novel drug delivery systems (NDDS)are pioneering to overcome these problems. The pertinent literature was compiled from a thorough search on various databases such as ScienceDirect, PubMed, Google Scholar, etc., utilizing numerous keywords, including ulcerative colitis, herbal drugs, CGA, pharmacological activities, mechanism of actions, nanoformulations, clinical updates, and many others. Relevant publications accessed till now were chosen, whereas non-relevant papers, unpublished data, and non-original articles were excluded. The present review comprises recent studies on pharmacological activities and novel drug delivery systems of CGA for managing UC. In addition, the clinical trials of CGA against UC have been discussed.
Subject(s)
Chlorogenic Acid , Clinical Trials as Topic , Colitis, Ulcerative , Drug Delivery Systems , Humans , Colitis, Ulcerative/drug therapy , Chlorogenic Acid/administration & dosage , Chlorogenic Acid/pharmacology , Chlorogenic Acid/therapeutic use , Chlorogenic Acid/chemistry , Animals , Anti-Inflammatory Agents/administration & dosage , Anti-Inflammatory Agents/therapeutic useABSTRACT
To increase the effectiveness of using typical biomass waste as a resource, iridoids, chlorogenic acid, and flavonoids from the waste biomass of Eucommia ulmoides leaves (EULs) were extracted by deep eutectic solvents (DESs) in conjunction with macroporous resin. To optimize the extract conditions, the experiment of response surface was employed with the single-factor of DES composition molar ratio, liquid-solid ratio, water percentage, extraction temperature, and extraction time. The findings demonstrated that the theoretical simulated extraction yield of chlorogenic acid (CGA), geniposidic acid (GPA), aucubin (AU), geniposide (GP), rutin (RU), and isoquercetin (IQU) were 42.8, 137.2, 156.7, 5.4, 13.5, and 12.8 mg/g, respectively, under optimal conditions (hydrogen bond donor-hydrogen bond acceptor molar ratio of 1.96, liquid-solid ratio of 28.89 mL/g, water percentage of 38.44%, temperature of 317.36 K, and time of 55.59 min). Then, 12 resins were evaluated for their adsorption and desorption capabilities for the target components, and the HPD950 resin was found to operate at its optimum. Additionally, the HPD950 resin demonstrated significant sustainability and considerable potential in the recyclability test. Finally, the hypoglycemic in vitro, hypolipidemic in vitro, immunomodulatory, and anti-inflammatory effects of EUL extract were evaluated, and the correlation analysis of six active components with biological activity and physicochemical characteristics of DESs by heatmap were discussed. The findings of this study can offer a theoretical foundation for the extraction of valuable components by DESs from waste biomass, as well as specific utility benefits for the creation and development of natural products.
Subject(s)
Eucommiaceae , Flavonoids , Flavonoids/chemistry , Solvents/chemistry , Chlorogenic Acid/chemistry , Eucommiaceae/chemistry , Deep Eutectic Solvents , Plant Extracts/chemistry , Water , IridoidsABSTRACT
Consumer demand for natural, chemical-free products has grown. Food industry residues, like coffee pulp, rich in caffeine, chlorogenic acid and phenolic compounds, offer potential for pharmaceutical and cosmetic applications due to their antioxidant, anti-inflammatory, and antibacterial properties. Therefore, the objective of this work was to develop a phytocosmetic only with natural products containing coffee pulp extract as active pharmaceutical ingredient with antioxidant, antimicrobial and healing activity. Eight samples from Coffea arabica and Coffea canephora Pierre were analyzed for caffeine, chlorogenic acid, phenolic compounds, tannins, flavonoids, cytotoxicity, antibacterial activity, and healing potential. The Robusta IAC-extract had the greatest prominence with 192.92 µg/mL of chlorogenic acid, 58.98 ± 2.88 mg GAE/g sample in the FRAP test, 79.53 ± 5.61 mg GAE/g sample in the test of total phenolics, was not cytotoxic, and MIC 3 mg/mL against Staphylococcus aureus. This extract was incorporated into a stable formulation and preferred by 88% of volunteers. At last, a scratch assay exhibited the formulation promoted cell migration after 24 h, therefore, increased scratch retraction. In this way, it was possible to develop a phytocosmetic with the coffee pulp that showed desirable antioxidant, antimicrobial and healing properties.
Subject(s)
Antioxidants , Coffea , Humans , Antioxidants/pharmacology , Antioxidants/chemistry , Caffeine/pharmacology , Caffeine/chemistry , Chlorogenic Acid/pharmacology , Chlorogenic Acid/chemistry , Plant Extracts/pharmacology , Plant Extracts/chemistry , Phenols/pharmacology , Anti-Bacterial Agents/pharmacology , Coffea/chemistryABSTRACT
Chlorogenic acid (CGA), also known as 3-caffeioylquinic acid or coffee tannin, is a water-soluble polyphenol phenylacrylate compound produced through the shikimate pathway by plants during aerobic respiration. CGA widely exists in higher dicotyledons, ferns and many Chinese medicinal materials, and enjoys the reputation of 'plant gold'. Here, we summarized the source, chemical structure, biological activity functions of CGA and its research progress in pigs, aiming to provide a more comprehensive understanding and theoretical basis for the prospect of CGA replacing antibiotics as a pig feed additive.
Subject(s)
Chlorogenic Acid , Coffee , Animals , Swine , Chlorogenic Acid/chemistry , Coffee/chemistry , AntioxidantsABSTRACT
Coffee is one of the most widely consumed beverages, which has several effects on the human body. In particular, current evidence suggests that coffee consumption is associated with a reduced risk of inflammation, various types of cancers, and certain neurodegenerative diseases. Among the various constituents of coffee, phenolic phytochemicals, more specifically chlorogenic acids, are the most abundant, and there have been many attempts to utilize coffee chlorogenic acid for cancer prevention and therapy. Due to its beneficial biological effect on the human body, coffee is regarded as a functional food. In this review article, we summarize the recent advances and knowledge on the association of phytochemicals contained in coffee as nutraceuticals, with a particular focus on phenolic compounds, their intake, and nutritional biomarkers, with the reduction of disease risk, including inflammation, cancer, and neurological diseases.
Subject(s)
Coffee , Neoplasms , Humans , Coffee/chemistry , Chlorogenic Acid/chemistry , Neoplasms/prevention & control , Phenols/pharmacology , Phytochemicals , InflammationABSTRACT
Lycopene-loaded emulsions were formulated with whey protein isolate (WPI) covalently modified with high methoxylated pectin (HMP) or/and chlorogenic acid (CA) prepared by dry heating or/and alkali grafting. Covalent WPI products were confirmed by SDS-PAGE and degree of graft/CA binding equivalent values. The α-helix and ß-sheet percentage, surface hydrophobicity and fluorescence intensity of WPI decreased significantly (p < 0.05) upon binding. Both binary and ternary complexes enhanced the stability of the emulsions, and lycopene retained more after UV irradiation, thermal treatment, storage, compared with emulsions stabilized by WPI, with the best protection by both ternary complexes. In vitro simulated digestion results showed that free fatty acids were released in the order of WPI > WPI-HMP > WPI-CA > WPI-HMP-CA ≈ WPI-CA-HMP. Bio-accessibility analysis showed the same trend as the fatty acid release rate. These results may provide a theoretical basis for applications of conjugating protein with polysaccharide or/and polyphenol emulsions.
Subject(s)
Chlorogenic Acid , Pectins , Whey Proteins/chemistry , Emulsions/chemistry , Pectins/chemistry , Lycopene , Chlorogenic Acid/chemistryABSTRACT
Phenolic acids are now receiving a great deal of interest as pervasive human dietary constituents that have various therapeutic applications against chronic and age-related diseases. One such phenolic acid that is being utilized in traditional medicine is chlorogenic acid (CGA). It is one of the most readily available phytochemicals that can be isolated from the leaves and fruits of plants, such as coffee beans (Coffea arabica L.), apples (Malus spp.), artichoke (Cynara cardunculus L.), carrots (Daucus carota L.), betel (Piper betle L.), burdock (Arctium spp.), etc. Despite its low oral bioavailability (about 33%), CGA has drawn considerable attention due to its wide range of biological activities and numerous molecular targets. Several studies have reported that the antioxidant and anti-inflammatory potentials of CGA mainly account for its broad-spectrum pharmacological attributes. CGA has been implicated in exerting a beneficial role against dysbiosis by encouraging the growth of beneficial GUT microbes. At the biochemical level, its therapeutic action is mediated by free radical scavenging efficacy, modulation of glucose and lipid metabolism, down-regulation of pro-inflammatory cytokines, such as tumor necrosis factor-alpha (TNF-α), interleukin-6 (IL-6), IL-1ß, and interferon-gamma (IFN-γ), upregulation of nuclear factor erythroid 2-related factor 2 (Nrf-2), and inhibition of the activity of nuclear factor- κß (NF-κß), thus helping in the management of diabetes, cardiovascular diseases, neurodegenerative disorders, cancer, hypertension etc. This review highlights the natural sources of CGA, its bioavailability, metabolism, pharmacotherapeutic potential, and underlying mechanisms of action for the clinical usefulness of CGA in the management of health disorders.
Subject(s)
Chlorogenic Acid , Diabetes Mellitus , Humans , Chlorogenic Acid/pharmacology , Chlorogenic Acid/therapeutic use , Chlorogenic Acid/chemistry , Diet , Hydroxybenzoates , Diabetes Mellitus/drug therapyABSTRACT
Coffee cherry is a rich source of caffeine and chlorogenic acids. In this study we investigate the structural analysis of caffeine-enriched whole coffee cherry extracts, CEWCCE by using 1H and 13C NMR spectroscopy. The changes in 1H chemical shift data in NMR spectra of CEWCCE compared to pure caffeine indicated the formation of complexes between caffeine and chlorogenic acids in aqueous solution. The effect of complexation on the peak position of caffeoylquinic acid and caffeine resonance with increasing addition of caffeine was investigated. 2D NOESY experiments show the presence of cross-peaks that are due to the proximity of chlorogenic acid and caffeine molecules in stable complexes in protic solvents. The quantification data of caffeine by 1H qNMR was found to be in close agreement with the data obtained by HPLC analysis.
Subject(s)
Coffea , Prunus avium , Coffea/chemistry , Coffee/chemistry , Chlorogenic Acid/chemistry , Caffeine/analysis , Magnetic Resonance Spectroscopy , Plant Extracts/chemistryABSTRACT
Chlorogenic acid (CQA) is one of phenolics commonly found in higher plants, possessing numerous health-promoting effects on humans. Unfortunately, it is easily degraded/transformed into other substances during extraction. Therefore, its reliable analysis requires a special approach that does not involve high temperatures. This paper presents a very simple method of CQA isolation using the sea sand disruption method with subsequent purification of the extract using the ion-pair solid-phase extraction process, followed by HPLC-DAD detection. It was found that control of the ion pairing reagent concentration and sample pH is crucial to improve purification, and that the best results, with recovery exceeding 98%, were obtained for 0.05 M tetrabutylammonium bisulfate at pH 7 when the ion pairs were formed directly in the extract and eluted from the C18 sorbent using an acidified methanol-water mixture. The practical potential of the developed procedure was verified by using it for CQA isolation from different plants. The approach represents one of the contemporary analytical trends and current advances in the solid phase extraction, in which several sorption extraction techniques are combined to ensure high-quality analytical results.
Subject(s)
Chlorogenic Acid , Sand , Chlorogenic Acid/chemistry , Chromatography, High Pressure Liquid/methods , Humans , Plant Extracts/chemistry , Plants/chemistry , Solid Phase ExtractionABSTRACT
Scorzonera species belong to the Asteraceae family comprising more than 25000 species. The present study aimed to examine the phytochemical profiles and biological activities of S.â sandrasica Hartvig et Strid, S.â coriacea A. Duran&Aksoy, and S.â ahmet-duranii Makbul&Coskuncelebi which are endemic species to Turkey. Flavonoids such as hyperoside, isoquercitrin, rutin, isoorientin, orientin, 7-O-methyl isoorientin, luteolin-7-O-ß-glycoside, apigenin-7-O-ß-glucoside, vitexin, isovitexin as well as caffeoylquinic acid derivatives including chlorogenic acid, 4,5-O-dicaffeoylquinic acid, and 1,5-O-dicaffeoylquinic acid contents were analyzed to clarify phytochemical content of the extracts. Aerial parts of the investigated extracts were determined as contain flavonoids in high amounts. Chlorogenic acid and its derivatives were detected in all investigated species, in varying amounts, both in the roots and aerial parts. S.â coriacea aerial parts contained the highest total phenolic and flavonoids. The strongest inhibitory activities on ABTS and DPPH radicals were also observed with S.â coriacea aerial parts by 8.07±0.28 and 13.94±0.53â µg/ml of IC50 values, respectively. Total phenolic contents of the extracts were significantly correlated with DPPH (r=-0.9842, p=0.0004) and ABTS free radical scavenging (r=-0.9870, p=0.0003) and total antioxidant capacity (r=0.8173, p=0.0470), as well as total flavonoid contents (r=0.8820, p=0.0201). S.â sandrasica aerial parts and S.â ahmet-duranii roots exhibited the greatest red blood cell membrane protection and protein denaturation inhibition, respectively. From the phytochemical point of view, all the selected species were analyzed for the first time.
Subject(s)
Scorzonera , Antioxidants/pharmacology , Apigenin , Chlorogenic Acid/pharmacology , Chlorogenic Acid/chemistry , Flavonoids/pharmacology , Flavonoids/analysis , Free Radicals , Glucosides , Luteolin , Phenols/chemistry , Phytochemicals/pharmacology , Plant Extracts/chemistry , Rutin , Scorzonera/chemistry , TurkeyABSTRACT
A holistic ultraperformance liquid chromatography (UPLC)-time of flight (TOF)-mass spectrometry-based approach was used to screen for storage-induced reaction products consisting of the volatile key coffee thiols methanethiol, 2-furfurylthiol, 2-methyl-3-furanthiol, 3-mercapto-3-methylbutanol, and 3-mercapto-2-butanone and low-molecular weight phenolic constituents of coffee beverages including chlorogenic acid, caffeic acid, and their thermal degradation products hydroxyhydroquinone, catechol, and 4-ethylcatechol. Multiple marker compounds could be detected in thiol-enriched coffee brews after UPLC-TOF-MS profiling and statistical data analysis. Subsequently, marker compounds were synthesized and structurally characterized via high-resolution mass spectrometry and 1D- and 2D-NMR experiments. Quantification of these reaction products in fresh and stored coffee beverages was realized in native coffee and after stir bar sorptive extraction with liquid desorption by means of UHPLC-MS/MS. The quantitative data revealed the biggest influence of storage time on the formation of reaction products between hydroxyhydroquinone and methanethiol and 2-furfurylthiol, while other reaction products were only slightly affected by storage and thus most likely formed during the roasting process.
Subject(s)
Chlorogenic Acid , Coffee , Caffeic Acids , Chlorogenic Acid/chemistry , Coffee/chemistry , Odorants/analysis , Sulfhydryl Compounds/chemistry , Tandem Mass SpectrometryABSTRACT
Prosopis farcta (Banks & Sol.) J.F.Macbr. is an emerging medicinal plant containing a diverse array of phytochemicals, including protein, fat, carbohydrate, fibre, alkaloids, fatty acids, glycosides, and polyphenols, with strong antioxidant potential. However, the screening and characterization of phenolic compounds in P. farcta is limited. This study is conducted to determine the polyphenol contents and their antioxidant activity in P. farcta leaves samples via liquid chromatography-electrospray ionization quadrupole time-of-flight mass spectrometry (LC-ESI-QTOF-MS/MS) and high-performance liquid chromatography-photodiode array (HPLC-PDA). Total phenolic content (TPC), total flavonoid content (TFC), and total tannins content (TTC) were determined for polyphenol estimation. The antioxidant properties were measured by total antioxidant capacity (TAC), 2,2'-Diphenyl-2-picrylhydrazyl (DPPH), Ferric Reducing Antioxidant Power (FRAP), and 2,2"²-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS). LC-ESI-QTOF-MS/MS was used to identify and characterize 47 phenolic compounds, which mainly included phenolic acids (13), flavonoids (28), other polyphenols (4), lignans (1), and stilbenes (1). According to HPLC-PDA quantification, chlorogenic acid (9.78 ± 2.15 mg/g dw) was the most abundant phenolic acid, while the main flavonoids included catechin (12.73 ± 1.29 mg/g dw) and kaempferol (7.93 ± 1.47 mg/g dw). The study demonstrated the significance of P. farcta as a rich source of phenolic compounds with antioxidant capacity that can be widely used in food, beverage, feed, and pharmaceutical applications.
Subject(s)
Antioxidants/pharmacology , Chromatography, High Pressure Liquid/methods , Phenols/pharmacology , Prosopis/chemistry , Spectrometry, Mass, Electrospray Ionization/methods , Tandem Mass Spectrometry/methods , Antioxidants/analysis , Antioxidants/chemistry , Catechin/analysis , Catechin/chemistry , Catechin/pharmacology , Chlorogenic Acid/analysis , Chlorogenic Acid/chemistry , Chlorogenic Acid/pharmacology , Flavonoids/analysis , Flavonoids/chemistry , Flavonoids/pharmacology , Molecular Structure , Phenols/analysis , Phenols/chemistry , Phytochemicals/analysis , Phytochemicals/chemistry , Phytochemicals/pharmacology , Plant Extracts/analysis , Plant Extracts/chemistry , Plant Extracts/pharmacology , Plant Leaves/chemistry , Plants, Medicinal/chemistry , Polyphenols/analysis , Polyphenols/chemistry , Polyphenols/pharmacologyABSTRACT
The increasing interest towards greener antioxidants obtained via natural sources and more sustainable processes encourages the development of new theoretical and experimental methods in the field of those compounds. Two advanced separation methods using supercritical CO2 are applied to obtain valuable antioxidants from Salvia officinalis, and a first approximation to a QSAR model relating molecular structure with antioxidant activity is explored in order to be used, in the future, as a guide for the preselection of compounds of interest in these processes. Separation experiments through antisolvent fractionation with supercritical CO2 were designed using a Response Surface Methodology to study the effect of pressure and CO2 flow rate on both mass yields and capability to obtain fractions enriched in three antioxidant compounds: chlorogenic acid, caffeic acid and rosmarinic acid which were tracked using HPLC PDA. Rosmarinic acid was completely retained in the precipitation vessel while chlorogenic and caffeic acids, though distributed between the two separated fractions, had a major presence in the precipitation vessel too. The conditions predicted for an optimal overall yield and enrichment were 148 bar and 10 g/min. Although a training dataset including much more compounds than those now considered can be recommended, descriptors calculated from the σ-profiles provided by COSMO-RS model seem to be adequate for estimating the antioxidant activity of pure compounds through QSAR.
Subject(s)
Antioxidants/chemistry , Antioxidants/isolation & purification , Plant Extracts/chemistry , Plant Extracts/isolation & purification , Salvia officinalis/chemistry , Antioxidants/analysis , Caffeic Acids/chemistry , Chemical Fractionation/methods , Chlorogenic Acid/chemistry , Chromatography, High Pressure Liquid , Chromatography, Supercritical Fluid/methods , Cinnamates/chemistry , Depsides/chemistry , Molecular Conformation , Plant Extracts/analysis , Quantitative Structure-Activity Relationship , Rosmarinic AcidABSTRACT
Annonacea species have been reported to possess antitumor properties. However, the in vitro and in vivo antitumor activities of Xylopia aromatica (Annonacea) have not yet been elucidated. This study aimed to investigate the effects of Xylopia aromatica leaves hexane fraction (XaHF) on Ehrlich ascites carcinoma cells lines (EAC), both in vitro and in vivo. In vitro assays revealed a significant cytotoxic effect with the two lower XaHF concentrations (62.5 and 32.3mg/mL). EAC (2.5x106 cells) were inoculated in the right flank of Swiss mice, and the animals were treated intraperitoneally with 32.3mg kg-1 of XaHF daily, for 20 days. Our findings indicate that XaHF suppressed the growth of EAC in vivo, with a significant decrease (46%) in tumor volume. There was also a decrease in the necrosis area (71%), inflammatory infiltrate, and MMP-2 expression. High-Performance Liquid Chromatography with Diode Array Detector (HPLC-DAD) identified secondary metabolites possibly related to phenolic acids, flavonoids, and alkaloids. Thus, the results confirmed the antitumoral activity that may be related to the presence of the identified metabolites in XaHF extract.
Subject(s)
Carcinoma, Ehrlich Tumor/metabolism , Cell Proliferation/drug effects , Matrix Metalloproteinase 2/drug effects , Plant Extracts/pharmacology , Plant Leaves , Xylopia , Alkaloids/chemistry , Animals , Aporphines/chemistry , Carcinoma, Ehrlich Tumor/pathology , Catechin/chemistry , Cell Line, Tumor , Chlorogenic Acid/chemistry , Chromatography, High Pressure Liquid , Down-Regulation , Flavonoids/chemistry , Gallic Acid/chemistry , Lymphocytes, Tumor-Infiltrating/drug effects , Matrix Metalloproteinase 2/metabolism , Mice , Necrosis , Phenols/chemistry , Plant Extracts/chemistry , Quercetin/chemistry , Rutin/chemistry , Tumor Burden/drug effectsABSTRACT
BACKGROUND: Filtration of osmotic solution affects selective penetration during osmotic dehydration (OD), and after drying is finished, this can influence the chemical composition of the material, which is also modified by OD. METHODS: Osmotic dehydration was carried out in filtrated and non-filtrated concentrated chokeberry juice with the addition of mint infusion. Then, this underwent convective drying, vacuum-microwave drying and combined convective pre-drying, followed by vacuum-microwave finishing drying. Drying kinetics were presented and mathematical models were selected. The specific energy consumption for each drying method was calculated and the energy efficiency was determined. RESULTS AND DISCUSSION: The study revealed that filtration of osmotic solution did not have significant effect on drying kinetics; however, it affected selective penetration during OD. The highest specific energy consumption was obtained for the samples treated by convective drying (CD) (around 170 kJ·g-1 fresh weight (fw)) and the lowest for the samples treated by vacuum-microwave drying (VMD) (around 30 kJ·g-1 fw), which is due to the differences in the time of drying and when these methods are applied. CONCLUSIONS: Filtration of the osmotic solution can be used to obtain the desired material after drying and the VMD method is the most appropriate considering both phenolic acid content and the energy aspect of drying.
Subject(s)
Desiccation/methods , Malus/drug effects , Mentha/metabolism , Osmosis , Plant Extracts/chemistry , Antioxidants/chemistry , Caffeic Acids/chemistry , Chemistry, Physical/methods , Chlorogenic Acid/chemistry , Chromatography, Liquid , Cinnamates/chemistry , Color , Depsides/chemistry , Energy Metabolism , Filtration , Food Handling , Fruit/chemistry , Hydroxybenzoates/analysis , Kinetics , Microwaves , Models, Theoretical , Phenol , Tandem Mass Spectrometry , Temperature , Rosmarinic AcidABSTRACT
Nerium oleander L. is a widely used medicinal plant for pharmaceutical purposes. In this work, an extract of the pink flowers of this plant (FE) was characterized in terms of phenolic composition by LC-DAD-ESI-MS/MS and bioactivity, namely, antioxidant and antiproliferative effects. A total of 20 compounds from different classes, including derivatives of phenolic acids and flavonoid glycosylated derivatives, were identified in FE. Chlorogenic acid was the dominant phenolic compound in the extract (62.28 ± 1.74 µg mg-1 of dry extract). The antioxidant activity was assessed by ORAC assay, and FE showed an ability to reduce peroxyl radicals (ORAC value of 791.26 µmol TEAC per g DE). Additionally, the FE inhibited the proliferation of a colorectal cancer cell line (HT29 cells, EC50 = 11.72 ± 0.02 µg mL-1) and showed no cytotoxicity to confluent Caco-2 cells, a model of human intestinal epithelium. These results provide new information about the phenolic composition of Nerium oleander pink flowers and the bioactivity of the extracts.
Subject(s)
Antineoplastic Agents/pharmacology , Chlorogenic Acid/pharmacology , Nerium , Plant Extracts/pharmacology , Antineoplastic Agents/chemistry , Caco-2 Cells/drug effects , Chlorogenic Acid/chemistry , Flowers , HT29 Cells/drug effects , Humans , Phytotherapy , Plant Extracts/chemistry , Spectrometry, Mass, Electrospray IonizationABSTRACT
The aim of this study was to investigate and compare the effects of different extraction techniques (high hydrostatic pressure-assisted extraction (HHPE), ultrasound-assisted extraction (UAE), and classical solvent extraction (CSE)) on phenolic compounds from spent coffee grounds (SCG). Different HHPE parameters (300, 400 and 500 MPa at 25 °C for 5, 10 and 15 min) and UAE parameters (40%, 50%, and 60% amplitude at 25 °C for 5, 10 and 15 min) were used. These techniques were compared with CSE (at 50 °C for 30 min) according to total phenolic content (TPC), antioxidant activity (AA), high-performance liquid chromatography (HPLC), scanning electron microscopy (SEM), and infrared (IR) spectroscopy. The results showed that eco-friendly techniques increased the TPC and AA compared to CSE and morphological changes were verified by SEM results. Furthermore, chlorogenic and caffeic acid were also quantified by using HPLC. Chlorogenic acid was found as the main phenolic compound in spent coffee grounds (SCG). The highest chlorogenic acid was detected as 85.0 ± 0.6 mg/kg FW with UAE at 60% amplitude for 15 min. In brief, for the extraction of phenolic compounds from waste SCG eco-friendly techniques such as HHPE and/or UAE were more convenient than CSE.
Subject(s)
Coffee/chemistry , Phenols/chemistry , Antioxidants/chemistry , Caffeic Acids/chemistry , Chlorogenic Acid/chemistry , Chromatography, High Pressure Liquid/methods , Waste ProductsABSTRACT
To gain comprehensive insight into the interactions of key coffee odorants, like the Strecker aldehydes, acetaldehyde, propanal, methylpropanal, 2- and 3-methylbutanal, and methional, and the nonvolatile fraction of coffee, an untargeted metabolomics approach was applied. Ultra performance liquid chromatography (UPLC)-time of flight (TOF)-mass spectrometry (ESI-) profiling followed by statistical data analysis revealed a marker substance for a coffee beverage spiked with acetaldehyde with an accurate mass of 217.0703 [M - H]-. This compound could be identified as a reaction product of quinic acid (QA) and acetaldehyde linked by acetalization at the cis-diol function of QA. Consequently, the acetalization of aldehydes, QA, 5-O-caffeoyl quinic acid (CQA), and quinic acid γ-lactone (QAL) was investigated by means of model reactions, followed by synthesis, isolation, and structure elucidation via UPLC-TOF-MS and 1D and 2D NMR techniques. UHPLC-MS/MSMRM screening and the quantification of aldehyde adducts in coffee beverages revealed the presence of QA/acetaldehyde, -/propanal, -/methylpropanal, and -/methional reaction products and CQA/acetaldehyde, -/propanal, -/methylpropanal, -/2- and 3-methylbutanal, and -/methional and QAL/acetaldehyde adducts for the first time, in concentrations of 12-270 µg/L for QA/aldehydes, 5-225 µg/L for CQA/aldehydes, and 62-173 µg/L for QAL/acetaldehyde. The sensory characterization of the identified compounds showed bitter taste recognition thresholds of 48-297 µmol/L for CQA adducts and 658 µmol/L for QAL/acetaldehyde, while the QA adducts showed no bitter taste (<2000 µmol/L).