Phenolic Acid Derivatives Research Articles

Cardioprotective effects of Plinia cauliflora (Mart.) Kausel in a rabbit model of doxorubicin-induced heart failure

Ethnopharmacological relevanceIn Brazil, the fruit of a native species that is popularly known as “jabuticaba” (Plinia cauliflora [Mart.] Kausel) is widely consumed fresh or used for the production of liqueur, juice, and jelly. In Brazilian folk medicine, this species is used to treat asthma, throat inflammation, and gastrointestinal and cardiovascular disturbances. However, no previous studies have reported its cardioprotective effects. AimTo evaluate the possible cardioprotective effects of a hydroethanolic extract of Plinia cauliflora (EEPC) in female rabbits in a model of doxorubicin-induced heart failure. Material and methodsEEPC was obtained and fractionated by solid phase extraction, and its constituents were determined by liquid chromatography coupled to diode array detector and mass spectrometry (LC-DAD-MS). Thirty female New Zealand rabbits received doxorubicin administration for 6 weeks to induce heart failure. EEPC was orally administered at doses of 75 and 150 mg/kg daily for 42 days. Enalapril (5 mg/kg) was used as a reference cardioprotective drug. At the end of the experimental period, blood pressure and heart rate were recorded. Serum parameters, including lipid profile, troponin, creatinine, nitrotyrosine, malondialdehyde, nitrite, and brain natriuretic peptide, were measured. The electrocardiographic profile and renal vascular reactivity were evaluated. Cardiac histopathology and ventricular morphometry were performed, and the tissue enzymatic antioxidant system was investigated. ResultsA total of 37 compounds were detected in EEPC, including organic acids, phenolic acid derivatives, flavonoids, anthocyanins, and hydrolysable tannins (gallotannins and ellagitannins). EEPC treatment induced a cardiorenal protective response, prevented hemodynamic and functional alterations, and prevented ventricle remodeling. These effects were associated with the normalization of creatinine and brain natriuretic peptide levels and modulation of the tecidual antioxidant defense system. ConclusionThe present study demonstrated that EEPC may prevent doxorubicin-induced heart failure by modulating the antioxidant defense system, reducing reactive oxygen species-induced damage, preventing alterations of hemodynamic and endothelial function, and preventing damage to the cardiac structure. EEPC, especially at the highest dose tested, may be considered a cardioprotective coadjuvant to prevent doxorubicin-induced cardiotoxicity.

Extraction and recovery of rare earths by chelating phenolic copolymers bearing diglycolamic acid or diglycolamide moieties

Extraction and recovery of rare earth elements (REEs) have been studied using ion-exchange and chelating process thanks to phenol copolymeric resins. The ion-exchange and chelating resins have been prepared through an alkaline polycondensation reaction of phenolic diglycolamic acid or diglycolamide derivatives with admixture of phenol, catechol or resorcinol in the presence of formaldehyde as crosslinker. The phenol copolymeric resins were fully characterized and involved in sorption experiments. The sorption experiments of rare earth elements have been investigated in different acidic conditions. Lanthanum (La), europium (Eu) and ytterbium (Yb) were chosen to represent the light, medium and heavy REEs respectively. Changes in the extraction properties of the copolymeric resins have been observed depending on the nature of chelating groups in the phenolic matrices and the extraction conditions. The obtained results indicate that the synthesized material exhibit good sorbent properties for REEs with cation uptake capacity in the range 50–100 mg/g and in some cases above 150 mg/g.

Chemical constituents of Medinilla septentrionalis (W. W. Sm.) H. L. Li (Melastomataceae)

Our phytochemical investigation of the whole plants of Medinilla septentrionalis (W. W. Sm.) H. L. Li led to the isolation of five tannins (1–5), five phenolic acids and phenolic acid derivatives (6–10), four flavonoids (11–14), two triterpenes (15 and 16), and one hydantoin derivative (17). The structures of the obtained compounds were identified using spectrometric methods (1H NMR, 13C NMR and MS). This is the first study reporting on the chemical constituent of M. septentrionalis and the chemotaxonomic relationships between Medinilla and other genera of Melastomataceae.

Pharmacological, phytochemical and in-vivo toxicological perspectives of a xero-halophyte medicinal plant: Zaleya pentandra (L.) Jeffrey

This study endeavours to investigate the phytochemical composition, biological properties and in vivo toxicity of methanol and dichloromethane extracts of Zaleya pentandra (L.) Jeffrey. Total bioactive contents, antioxidant (phosphomolybdenum and metal chelating, DPPH, ABTS, FRAP and CUPRAC) and enzyme inhibition (cholinesterases, tyrosinase α-amylase, and α-glucosidase) potential were assessed utilizing in vitro bioassays. UHPLC-MS phytochemical profiling was carried out to identify the essential compounds. The methanol extract was found to contain highest phenolic (22.60 mg GAE/g) and flavonoid (31.49 mg QE/g) contents which correlate with its most significant radical scavenging, reducing potential and tyrosinase inhibition. The dichloromethane extract was most potent for phosphomolybdenum, ferrous chelation, α-amylase, α-glucosidase, and cholinesterase inhibition assays. UHPLC-MS analysis of methanol extract unveiled to identify 11 secondary metabolites belonging to five sub-groups, i.e., phenolic, alkaloid, carbohydrate, terpenoid, and fatty acid derivatives. Additionally, in vivo toxicity was conducted for 21 days and the methanol extract at different doses (150, 200, 250 and 300 mg/kg) was administered in experimental chicks divided into five groups each containing five individuals. Different physical, haematological and biochemical parameters along with the absolute and relative weight of visceral body organs were studied. Overall, no toxic effect was noted for the extract at tested doses.

Hydroxycinnamic acid amide (HCAA) derivatives, flavonoid C-glycosides, phenolic acids and antioxidant properties of foxtail millet

The profiles of phenolic compounds and antioxidant properties of dehulled foxtail millets were studied. Twenty-one phenolics were detected in the free fraction, including a series of nine hydroxycinnamic acid spermidines reported for the first time and three flavonoid C-glycosides of kaempferol and apigenin. Twenty-three phenolic acid derivatives were detected in the bound fraction with ferulic acid being the predominant phenolic acid, as well as four ferulic acid dimers (DFAs) reported for the first time in foxtail millet. Total phenolic contents (TPC) of free and bound fractions varied from 161.86 to 224.47 mg ferulic acid equivalent (FAE)/kg DW, 170.69 to 294.75 mg FAE/kg DW, respectively. Antioxidant activities, based on the DPPH, ABTS+ and ORAC assays, were determined for all extracts related to TPC. Dehulled foxtail millet contains a diverse profile of phenolic compounds potentially suitable for development of functional foods with unique antioxidant properties.

Compositional Diversity among Blackcurrant ( Ribes nigrum) Cultivars Originating from European Countries.

Berries representing 21 cultivars of blackcurrant were analyzed using liquid chromatographic, gas chromatographic, and mass spectrometric methods coupled with multivariate models. This study pinpointed compositional variation among cultivars of different origins cultivated in the same location during two seasons. The chemical profiles of blackcurrants varied significantly among cultivars and growing years. The key differences among cultivars of Scottish, Lithuanian, and Finnish origins were in the contents of phenolic acids (23 vs 16 vs 19 mg/100 g on average, respectively), mainly as 5-O-caffeoylquinic acid, 4-O-coumaroylglucose, (E)-coumaroyloxymethylene-glucopyranosyloxy-(Z)-butenenitrile, and 1-O-feruloylglucose. The Scottish cultivars were grouped on the basis of the 3-O-glycosides of delphinidin and cyanidin, as were the Lithuanian cultivars. Among the Finnish samples, the content of myricetin 3-O-glycosides, 4-O-caffeoylglucose, 1-O-coumaroylglucose, and 4-O-coumaroylglucose were significantly different between the two green-fruited cultivars and the black-fruited cultivars. The samples from the studied years differed in the content of phenolic acid derivatives, quercetin glycosides, monosaccharides, and citric acid.

Chemical composition and cytotoxic screening of Musa cavendish green peels extract: Antiproliferative activity by activation of different cellular death types

Musa cavendish, commonly known as banana, is a fruit with nutritional and therapeutic properties. We investigated the chemical composition and in vitro cytotoxic effect of M. cavendish green peel extract (MHE) on cancer cells for the first time. The compounds characterization was performed by HPLC-UV/Vis and FIA-ESI-IT-MSn. We investigated in vitro cytotoxic effect of Musa cavendish green peels extract (MHE) in HepG2, A-375, MCF-7 and Caco-2 cancer cells. We evaluated the effect of MHE on proliferation of different cell lines through apoptosis, necrosis, mitochondrial membrane potential (MMP) and reactive oxygen species (ROS) content determination. We identified 12 compounds from different classes in the extract, including derivatives of phenolic acids, aglycone flavonoids, glycoside flavonoids and catecholamines. Our results indicate that MHE exerts, after 48 h treatment, an accentuated antiproliferative effect from the dose of 100 μg/mL in all cell lines tested. In HepG2 cells, these effects were related to the induction of cell death, both necrotic and apoptotic, and remarkable changes in cell morphology. Depolarization of MMP and high ROS content were also observed in the cells in a dose-dependent manner. Our results show that MHE may be used as a source of new drugs with anticancer activity.

Phytochemical Characterization of Five Edible Purple-Reddish Vegetables: Anthocyanins, Flavonoids, and Phenolic Acid Derivatives.

Vegetables comprise a significant portion of our daily diet with their high content in nutrients including fiber, vitamins, minerals, as well as phenolic compounds. Vegetable consumption has been shown to be positively associated with the prevention of several degenerative diseases thanks to their bioactive compounds. Accordingly, five selected vegetables, namely, red chicory, red onion, eggplant, purple sweet potato, and black carrot were thoroughly assessed for their phenolic content in this study. For this purpose, the total phenolic and flavonoid content of these five vegetables and their antioxidant activities that are based on three common methods ABTS radical cation decolorization assay (ABTS), Cupric Ion Reducing Antioxidant Capacity (CUPRAC), and DPPH scavenging activity assay were determined. Additionally, HPLC-PDA/Electrospray ionization coupled with mass spectrometry (HPLC-PDA/-ESI+-MS)-based identification and quantification of the members belonging to polyphenols present in each vegetable were determined. Statistical correlations between antioxidant activities and the specific type of phenolic compounds, such as anthocyanins, flavonoids, anthocyanins, and phenolic acids were further elucidated. Phenolic acids (chlorogenic and syringic acids) were found to be the most abundant compounds that are present in all samples. Among the anthocyanins, cyaniding derivatives were present in all vegetables. In terms of their antioxidant activities, the analyzed vegetables were ranked as red chicory > purple sweet potato > black carrot > eggplant > red onion, in descending order. Superior antioxidant activities exhibited by red chicory and purple sweet potato were attributed to the high content of phenolic compounds, especially flavonols (quercetin-3,4-O-diglucoside) in red chicory and anthocyanins (peonidin-3-caffeoyl p-hydroxybenzoylsophoroside-5-glucoside) in purple sweet potato.

New naturally occurring phenolic derivatives from marine Nocardiopsis sp. AS23C: Structural elucidation and in silico computational studies

AbstractIn our persistent research for new bioactive secondary metabolites from marine actinomycetes, Nocardiopsis sp. AS23C strain was isolated from the marine Alga Sargassum arnaudianum collected in the Red Sea at Hurghada coast, Egypt. A large‐scale fermentation of the strain on M2 medium containing 50% sea water, followed by fractionation and purification of the obtained extract afforded a new phenolic acid derivative, 4‐amino‐6‐methylsalicylic acid (1a), together with 5‐methylresorcinol (2) and linoleic acid (3). Their molecular structures were proved through the sophisticated spectroscopic analyses including exhaustive 1D and 2D NMR (1 and 2‐Dimensional Nuclear Magnetic Resonance) as well mass spectroscopy techniques. The extract exhibited antibacterial activity against the Gram‐positive Staphylococcus aureus, Bacillus subtilis ATCC6051, and Streptomyces viridochromogenes Tü 57. An in vitro cytotoxicity assaying of 1a and 2 against the human cervix carcinoma cell line (KB‐3‐1), pronounced no obvious activity. Additionally, in silico predictions of physicochemical properties, ADME (absorption, distribution, metabolism and excretion) parameters, acute oral toxicity and indication of toxicity targets were performed for 1a and 2 in comparison with the antioxidant agent orsellinic acid.

Phytochemical Characterization and Biological Activities of a Hydroalcoholic Extract Obtained from the Aerial Parts of Matthiola incana (L.) R.Br. subsp. incana (Brassicaceae) Growing Wild in Sicily (Italy).

This study aimed to characterize the phenolic and the volatile constituents and to establish the antioxidant potential and the toxicity of a hydroalcoholic extract obtained from the leaves and flower buds of Matthiola incana (L.) R.Br. subsp. incana growing wild in Sicily (Italy). By HPLC-PDA/ESI-MS analysis, 12 phenolics (two phenolic acid derivatives and ten flavonoids) were identified, and eight of them were reported for the first time; luteolin-glucoside was the main component (57.07 mg/g±0.87 % RSD). By SPME-GC/MS, 47 volatile constituents were fully characterized, and dimethyl trisulfide turned out to be the most abundant one (33.24 %). The extract showed moderate activity both in the DPPH and in the reducing power assays (IC50 =2.32±0.24 mg/mL; ASE/mL=12.29±0.42); it did not inhibit the lipid peroxidation, whereas it was found to possess good chelating properties reaching approximately 90 % activity at the highest tested dose. Moreover, the extract protected growth and survival from H2 O2 -induced oxidative stress in Escherichia coli. Finally, the extract was non-toxic against Artemia salina (LC50 >1000 μg/mL). These findings increase the knowledge of M. incana subsp. incana and they could be helpful to a chemosystematic distinguishing of this subspecies also demonstrating that the aerial parts represent a safe source of antioxidants.

Accumulation of phenolic compounds in different in vitro cultures of Salvia viridis L. and their antioxidant and antimicrobial potential

Different in vitro cultures of the Turkish origin medicinal plant species, Salvia viridis, were estimated in order to investigate their potential for the accumulation of phenolic compounds. Among the seventeen detected compounds, thirteen phenolic acid derivatives and four phenylethanoids were identified in extracts from shoot and/or callus cultures using the UPLC-DAD/ESI-MS method. The accumulation of the compound depended on the type of culture (callus, shoot), the medium composition and age of culture (6, 12, 18 and 24 months in in vitro conditions). Six of the seventeen detected compounds were estimated in all the analyzed samples, however, sometimes only in trace amounts. The predominant metabolite was rosmarinic acid (RA). Its content ranged between 2.4 and 11.5 mg/g dry weight (DW). The highest levels of rosmarinic acid and total phenolic compounds were found in a half-year-old shoot culture. The content of the RA was nine times higher than that in the shoots of plant grown in field conditions. The antioxidant activity of S. viridis cultures was examined by the O2− and 1-1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging test and FRAP (ferric reducing antioxidant power) assay. In addition, the antifungal and the antibacterial activities were examined against a wide spectrum of micro-organisms. All the samples showed promising antioxidant potential; however, the shoot extract had the highest antioxidant activity in all the assays. Preliminary results demonstrated that all the analyzed extracts inhibited the growth of Gram-positive and Gram-negative bacteria. The extracts also showed strong activity against Candida and Aspergillus species.

The use of nanofiltration membranes for the fractionation of polyphenols from grape pomace extracts

Filtration experiments in batch concentration mode (with recycling of the retentate stream) of grape pomace extract were performed in laboratory filtration membrane equipment by using nine commercial nanofiltration (NF) membranes with an approximate molecular weight cut-off (MWCO) of 1000‒150 Da. The filtration experiments of the selected pomace extract were performed by modifying the most important operating variables: transmembrane pressure, tangential velocity, temperature, and the nature and MWCO of the membranes. The evolution of the cumulative permeate volumes and permeate fluxes with processing time was analyzed till a volume reduction factor (VRF) of 10 was reached. The effect of the mentioned operating conditions was discussed. The effectiveness of the filtration treatments was determined by the evaluation of the rejection coefficients for several families of polyphenols. Membranes possessing MWCO between 1000 and 500 Da were able to quantitatively recover polymeric proanthocyanidins in the concentrate stream and separate them from phenols that passed through the membrane into the permeate stream. On the other hand, the 600 to 300 Da membranes could also be used for the fractionation of monomeric phenolic families. The membranes were able to partially remove the anthocyanin fragments of phenolic acid derivatives and flavonols in the concentrate stream and at the same time.

Phenolic Acids Derivatives - Biotechnological Methods of Synthesis and Bioactivity.

Phenolic acids are secondary plant metabolites belonging to polyphenol classes, widely spread throughout the plant kingdom. The name "phenolic acids", in general, describes phenols that possess one carboxylic acid functionality and they could be divided into three major subclasses: hydroxybenzoic, hydroxycinnamic and hydroxyphenylacetic acids. The great interest in phenolic acids is associated with their high potential for food preservation (antioxidant and antimicrobial activity) and, last but not least, high therapeutic potential. The aim of this review is to summarise the current knowledge concerning phenolic acids and the topics discussed include natural sources of phenolic acids, biosynthesis and metabolism, health benefits of phenolic acids (first of all the antioxidant activity of dietary phenolics and also anticarcinogenic and anti-inflammatory effect), their antimicrobial activity for selected groups of bacteria and fungi (yeasts) and structural modifications of the molecule especially those increasing lipophilicity and improving solubility in lipids. Recent advances in the methods of enzymatic synthesis of phenolic acid derivatives are described and some conclusions referring to Structure-Property-Activity Relationships of phenolic acids, particularly important from the point of view of their pharmaceutical and nutritional applications, are discussed.

Effect of <i>Antigonon leptopus</i> Leaf Extract on Seed Germination and Seedling Growth of <i>Trigonella foenum graecum</i>

<i>Trigonella foenum graecum</i> (fenugreek) seeds were treated with different dilutions of aqueous leaves extract of <i>Antigonan</i> (i.e., from 10 to 50%) and grown on sterile cotton and Whatman filter paper in a Petri dish. The seedling length, fresh weight and dry weight of plants was taken after 5 to 15 days. It was found that the germination was 62% (85% in distilled water control and the germination process was completed in 2 days) in all dilutions and growth was severely inhibited as compared to distilled water grown control. Growth inhibition was increases with extract concentration. Maximum inhibition was recorded in radicle growth after five days of sowing in treated seedling with 50% aqueous extracts. Qualitative LCMS analysis of methanolic leaf extract of <i>A. leptopus</i> reveals the presence of various phenolic acid derivatives, like ferulic acid derivatives, arachidonic acid, citronellic acid, and coumarins derivatives etc. These phytotoxins not only inhibits the germination but also plant growth and interfere with ion accumulation of the plant. These results indicate that <i>Antigonan</i> plants have strong negative allopathic interactions with <i>Trigonella</i>. <i>Antigonan</i> may be harmful for our crop as well as native plants. However, the plant has certain medicinal properties like anti-cancerous properties, anti-diabetic properties that can be utilized for human welfare.

UPLC-DAD-QToF/MS를 이용한 야콘(Smallanthus sonchifolius) 괴근 내 페놀산 유도체 분석

UPLC-DAD-QToF/MS를 이용한 야콘(Smallanthus sonchifolius) 괴근 내 페놀산 유도체 분석

Metabolomic profiling and anti-infective potential of Zinnia elegans and Gazania rigens (Family Asteraceae)

The present study evaluates the chemical composition of Zinnia elegans and Gazania rigens based on their metabolomic profiles using liquid chromatography coupled with high-resolution mass spectrometry (LC‐HR-MS), alongside with the anti-infective activities of their ethanol extracts, as well as, different fractions. A significant difference was observed between the LC-MS profiles of the two plants such as, coumarins, sesquiterpene lactones and phenylethanoids which were characteristic for Z. elegans, while amides and phenolic acid derivatives were characteristic for G. rigens. These results highlight the chemical potential of Z. elegans and G. rigens. Furthermore, the ethyl acetate fraction of Z. elegans showed a significant antimalarial activity with IC50 values of 21.03 and 13.72 µg/mL against Plasmodium falciparum D6 and P. falciparum W2, respectively.

Salviachinensines A-F, Antiproliferative Phenolic Derivatives from the Chinese Medicinal Plant Salvia chinensis.

Six new phenolic acid derivatives, salviachinensines A-F (1-6), together with 14 known compounds (7-20) were isolated from the Chinese medicinal plant Salvia chinensis. The structures of salviachinensines A-F (1-6) were elucidated by NMR spectroscopy, bioinspired chemical synthesis, ECD analysis, and quantum chemical calculation methods. Compounds 2 and 3 are a pair of cis- trans isomers, and compounds 5 and 6 a pair of epimers. The solvent-induced isomerization of compounds 5 and 6 and the hypothetical biogenetic pathway of compounds 1-6, as well as the antiproliferative property and the ability of 1 to induce apoptosis and arrest cell cycle progression of MOLM-13 cells, were also investigated.

Phytochemical analysis and anti-inflammatory effects of Filipendula vulgaris Moench extracts

Filipendula vulgaris Moench (dropwort) is used in traditional medicine for relieving various inflammation-related diseases. In the present study, the phytochemical profile of F. vulgaris aerial part (FVA) and root (FVR) methanolic extracts was evaluated by LC-DAD-HRMS analysis. Furthermore, their in vitro and in vivo anti-inflammatory effects, as well as their potential cytotoxicity, were assessed. Results showed that the extracts mainly contain phenolics like flavonoids, hydrolyzable tannins, procyanidins, and phenolic acid derivatives, including gaultherin. No in vitro cytotoxicity was found at the highest concentration (50 μg/mL). FVA extract (50 μg/mL) significantly inhibited cyclooxygenase-1 and -2 (COX-1 and COX-2) activities in vitro (>50% inhibition), and FVR extract considerably inhibited COX-2 activity (52.5 ± 2.7%) without affecting COX-2 gene expression in LPS-stimulated THP-1 cells. The extracts demonstrated prominent in vivo anti-inflammatory potential upon oral administration in rats. Especially FVA extract at 100 and 200 mg/kg significantly inhibited carrageenan-induced edema formation. From these results, it can be concluded that F. vulgaris extracts possess interesting anti-inflammatory properties.

Determination and quantification of phenolic acids in raw propolis by reversed phase high performance liquid chromatography. Feasibility study for the use of near infrared spectroscopy

In this study we analyzed the phenolic composition of 50 propolis extracts from Spain and Chile by high performance liquid chromatography (HPLC). Ten compounds were identified and quantified: caffeic acid; p-coumaric acid; cinnamic acid; ferulic acid; isoferulic acid and 3,4-dimethyl-caffeic acid (DMCA); caffeic acid benzyl ester; p-coumaric cinnamyl ester; p-methoxy cinnamic acid cinnamyl ester; and caffeic acid phenylethyl ester (CAPE). The amounts of phenolic acids found ranged from 20.1–156.4 mg/g for Spanish propolis to 1.7–37.4 mg/g for Chilean propolis. Higher amounts were found for phenolic acid derivatives in all samples analyzed with values between 23.5–132.2 mg/g in Spanish propolis and 21.0–123.0 mg/g in Chilean propolis. A new method based on Near-Infrared Spectroscopy (NIR) is used to estimate the phenolic composition of acids and acid derivatives. The results obtained show that there are no differences between the results obtained by NIR spectroscopy and the chromatographic data.

Characterizing the phenolic constituents and antioxidant capacity of Georgia peaches

Acetonic crude phenolic extracts of six Georgia peach cultivars were prepared and separated into low- and high-molecular-weight (LMW and HMW) fractions by Sephadex LH-20 column chromatography. Further characterization via RP-HPLC-ESI-MS identified the main phenolics as hydroxycinnamates, (+)-catechin, and proanthocyanidins with degrees of polymerization up to seven. The LMW phenolics of the commercial cultivar, ‘July Prince’, were further chromatographed and examined by RP-HPLC-ESI-MS. Derivatives of phenolic acids and flavan-3-ols, along with eriodictyol and quercetin diglycosides, were identified. Antioxidant capacities of the LMW and HMW fractions were determined using in vitro assays. H-ORACFL and FRAP assays gave values of 872 to 2428 μmol Trolox eq./100 g f.w. and 309 to 432 μmol Fe2+ eq./100 g f.w., respectively. The total phenolics content (TPC) was also measured; correlations between TPCs and antioxidant assays indicated that the HMW fractions of peach extracts were major contributors to the antioxidant capacity of the cultivars analyzed.