Phenolic Acid Constituents Research Articles

Computational evaluation of bioactive compounds from Viscum album (mistletoe) as inhibitors of p63 for pancreatic cancer treatment

Pancreatic ductal adenocarcinoma is an aggressive malignancy usually detectable at the advanced stage, with a 5-year survival rate of less than 8%. It has been reported that a gene called tumor-protein 63 (TP63) is expressed in an aggressive form of pancreatic cancer with a squamous signature. Thus, inhibiting the activity of p63 can be a means of treating and managing PDA. Different studies have shown that plant constituents are rich and can be a promising source for discovering drug candidates. The extract from mistletoe (Viscum album) is known to contain anticancer compounds; however, the specific molecular mechanism of the bioactive compounds is unknown. This study examines the pancreatic cancer therapeutic potential of the bioactive compounds in the flavonoid and phenolic acid constituents of mistletoe by adopting structural bioinformatics and advanced theoretical chemistry techniques via molecular docking, molecular dynamics simulation, molecular mechanics/generalized Born surface area (MM/GBSA) calculations, pharmacokinetic analysis, and density functional theory analysis. The six best compounds from the flavonoid constituent with the highest binding affinity ranging from −6.8 kcal/mol to −6.7 kcal/mol were selected with the control gemcitabine (−5.5 kcal/mol) for further computational analysis after molecular docking. Furthermore, MM/GBSA calculation showed the highest binding energy for the selected docked compounds, which validates their inhibitory potential. Hence, the molecular dynamics simulation, post-simulation analysis, pharmacokinetics model, and DFT results showed that mistletoe compounds are reliable due to their stable interaction with the target protein and drug-likeness properties. Communicated by Ramaswamy H. Sarma

Antioxidant activity and phenolic acid constituents of two andean Hypericum L. species from Colombia

Antioxidant capacity of extracts of different polarity obtained from two Hypericum L. species (H. juniperinum and H. mexicanum) was assessed by means of total polyphenolic content (TPC), 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay, 2,2-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) assay, ferric reducing antioxidant power (FRAP) assay and oxygen radical absorbance capacity (ORAC) assay. Their phenolic acid composition was also determined by HPLC. The ethyl acetate extract of H. juniperinum was the most active in the ABTS, FRAP and TPC assays with 10867.48 ?mol TEAC/g, 242.80 mg AAE/g and 491.08 mg GAE/g respectively. On the other hand, the methanol extract obtained from H. mexicanum appeared as the most active extract in the DPPH assay (3714.23 ?mol TEAC/g). Similarly, the butanol fraction coming from the methanolic extract of H. mexicanum showed the highest activity in the ORAC assay (12910.06 ?mol TEAC/g). HPLC analysis of the extracts revealed the presence of phenolic acid compounds, such as chlorogenic (50.09 mg/g) and p-coumaric acids (63.36 mg/g) in H. mexicanum and p-coumaric acid (8.45 mg/g) in H. juniperinum. A high correlation between antioxidant activity and total polyphenol content was established. Specifically, H. mexicanum exhibited the highest ORAC capacity, which may be associated with the high content of chlorogenic and p-coumaric acids present in medium to polar extracts. Our results constitute a significant contribution to the study of antioxidant activity and the determination of the phenolic acid profile in both species. The analysed extracts showed promising antioxidant activity that could be useful in the pharmaceutical, cosmetic and food industries.

Antiviral activities of Polygonum perfoliatum L. extract and related phenolic acid constituents against hepatitis B virus.

Chronic hepatitis B virus (HBV) infection is an important public health problem. Polygonum perfoliatum L. is a traditional medicinal herb and has been reported to have pharmacological activities such as anti-inflammatory, antibacterial, and antiviral. In this study, the antiviral activities and mechanisms of Polygonum perfoliatum L. extract against HBV and the effective components were investigated. The results showed that the total extract of Polygonum perfoliatum L. reduced the levels of HBV e antigen (HBeAg) secretion and the viral covalently closed circular DNA (CCC DNA) formation, but had little or no negative effects on viral capsid assembly and pregenomic RNA packaging. Further fractionation showed that the water extract (WE) fraction exerted comparable anti-HBV activities with the total extract, especially in inhibiting the CCC DNA formation and HBeAg production, indicating that the effective antiviral components are mainly distributed in this fraction. Further study showed that the phenolic acids constituents, protocatechuic acid, and gallic acid, but not ethyl caffeate, which is reported enriched in the WE fraction, showed strong anti-HBV activities in inhibiting viral core DNA synthesis, CCC DNA formation, and HBeAg production. These results suggested that the Polygonum perfoliatum L. total extract and the related phenolic acids like protocatechuic acid and gallic acid could inhibit HBV replication and also indicated the potential utility of Polygonum perfoliatum L. and related constituents as sources of novel antivirals against HBV.

Astringent Gallic Acid in Red Wine Regulates Mechanisms of Gastric Acid Secretion via Activation of Bitter Taste Sensing Receptor TAS2R4

Red wine is rich in phenolic compounds, which chiefly determine its characteristic taste. One of its major phenolic acid constituents for which an astringency, yet no clear contribution to bitter taste has been reported, is gallic acid (GA). In previous studies, we have demonstrated bitter-tasting constituents to regulate cellular proton secretion (PS) as a key mechanism of gastric acid secretion via activation of bitter taste sensing receptors (TAS2Rs). Here, we hypothesized a contributing role of GA to the red wine-stimulated effect on PS in human gastric tumor cells (HGT-1 cells). Sensory analyses revealed that 10 μM GA as the lowest concentration tested more bitter than tap water, with increasing bitter ratings up to 1000 μM. In HGT-1 cells, the concentration of 10 μM GA evoked the most pronounced effect on PS secretion, either when added to cells as in-water solution or when spiked to a red wine matrix. GA-spiking of Zweigelt and Blaufränkisch red wine samples up to a concentration of 10 μM resulted in an equally stimulated PS, whereas the non-GA-spiked wine samples demonstrated contrary effects on PS, indicating a functional role of GA on PS. Involvement of TAS2R4 in the GA-induced PS was verified by means of an HGT-1 homozygote CRISPR-Cas9 TAS2R4 knockout approach. Moreover, gene expression analyses revealed GA to increase TAS2R4. These results demonstrate a functional role of TAS2R4 in GA-evoked PS as a key mechanism of gastric acid secretion aiding digestion. Moreover, our data provide mechanistic insights, which will help to produce stomach-friendly red wines.

Evaluating Protein Tyrosine Phosphatase 1B Inhibitory Activity of Bioactive Compounds from Momordica charantia for Diabetes Treatment Type 2 by using Molecular Docking Method

Evaluating Protein Tyrosine Phosphatase 1B Inhibitory Activity of Bioactive Compounds from Momordica charantia for Diabetes Treatment Type 2 by using Molecular Docking Method

Antiviral activity of Sambucus FormosanaNakai ethanol extract and related phenolic acid constituents against human coronavirus NL63

Human coronavirus NL63 (HCoV-NL63), one of the main circulating HCoVs worldwide, causes respiratory tract illnesses like runny nose, cough, bronchiolitis and pneumonia. Recently, a severe respiratory illness outbreak of HCoV-NL63 has been reported in a long-term care facility. Sambucus FormosanaNakai, a species of elderberry, is a traditional medicinal herb with anti-inflammatory and antiviral potential. The study investigated the antiviral activity of Sambucus FormosanaNakai stem ethanol extract and some phenolic acid constituents against HCoV-NL63. The extract was less cytotoxic and concentration-dependently increased anti-HCoV-NL63 activities, including cytopathicity, sub-G1 fraction, virus yield (IC50 = 1.17 μg/ml), plaque formation (IC50 = 4.67 μg/ml) and virus attachment (IC50 = 15.75 μg/ml). Among the phenolic acid constituents in Sambucus FormosanaNakai extract, caffeic acid, chlorogenic acid and gallic acid sustained the anti-HCoV-NL63 activity that was ranked in the following order of virus yield reduction: caffeic acid (IC50 = 3.54 μM) > chlorogenic acid (IC50 = 43.45 μM) > coumaric acid (IC50 = 71.48 μM). Caffeic acid significantly inhibited the replication of HCoV-NL63 in a cell-type independent manner, and specifically blocked virus attachment (IC50 = 8.1 μM). Therefore, the results revealed that Sambucus Formosana Nakai stem ethanol extract displayed the strong anti-HCoV-NL63 potential; caffeic acid could be the vital component with anti-HCoV-NL63 activity. The finding could be helpful for developing antivirals against HCoV-NL63.

Estrogen Receptor-Mediated Transcriptional Activities of Spent Coffee Grounds and Spent Coffee Grounds Compost, and Their Phenolic Acid Constituents.

Spent coffee grounds (SCG) are the most abundant coffee byproduct and are generally discarded as waste. The horticultural use of SCG and SCG compost (SCGC) has become popular due to a growing interest in environmentally friendly measures for waste disposal. Estrogen-like endocrine disrupting chemicals in the soil can be absorbed by plants and subsequently by humans who consume these plants. The objectives of this study are to determine the phytochemical profiles of extracts of SCG and SCGC and to evaluate the estrogen-like activities of SCG, SCGC, and the major coffee phenolic acids, specifically, 5-O-caffeoylquinic acid (CQA), caffeic acid, and ferulic acid. Their inductive effects on estrogen receptor (ER)-mediated gene transcription have been examined in cultured cell lines. CQA was the most abundant phenolic acid in SCG and SCGC and was further examined for its ER-mediated estrogen-like activity using various assays. This is the first study to report the estrogen-like signaling activities of coffee byproducts and their major constituents.

Open-label uncontrolled pilot study on antipsoriatic activity of Rosa hemisphaerica

Background and objective: Rosa hemisphearica (Rosaceae) is highly cultivated worldwide as an ornamental plant and medicinally have an antibacterial and antioxidant effect. This study aimed to investigate clinically and histopathologically the anti-inflammatory activity of Rosa hemisphearica in psoriasis and to correlate the anti-inflammatory activity with the active constituents in the plant by the phytochemical study. Methods: In this open-label uncontrolled pilot study, a topical preparation of R. hemisphearica stem extract was used by 20 patients suffering from psoriasis for three weeks. Three histopathological slides for each patient, one each week for three weeks was done for anti-inflammatory response evaluation. Subsequently, total phenolic content was measured followed by thin layer chromatography (TLC) and high-performance liquid chromatography (HPLC) analysis for the identification of phenolic acid content in the stem. Results: By histopathological examination revealed that both Munro’s and Kogoj’s abscesses were gradually disappeared, the granular layer gradually restored to normal and the inflammatory cells gradually reduced in number prominently polymorph (neutrophils) and eventually histocytes disappeared. Total phenolic contents in R. hemisphearica stem extract were determined as 205.625 µg gallic acid equivalent each gm of the sample extract, TLC, and HPLC results showed the presence of rosmarinic acid in the stem extract. On quantitative HPLC analysis, the percentage of rosmarinic acid in the stem extract was 0.024 with a retention time (Rt) of 3.4 min. The proposed HPLC method was found to be linear, accurate and precise. Conclusion: The organic solvent extract of R. hemisphearica stem showed a significant reduction in an inflammatory cell among psoriatic patients under study. Rosmarinic acid was identified by TLC and HPLC as important phenolic acid constituents.

Carotenoids, Phenolics, Hydroxycinnamic Acids and Tannin Composition of Salacia senegalensis (Lam) DC Leaves

Salacia senegalensis leaves with established antimalarials activities were assayed (dry weight) for its carotenoids, phenolics, hydroxycinnamic acids and tannin composition using gas chromatography analysis. The results showed the presence of carotenoids, phenolic acids, hydroxycinnamic acids and tannic acids. Ten known carotenoids were detected, mainly lutein (6.4370100 mg/100 g), carotene (4.0964900 mg/100 g), viola-xanthin (3.3858800 mg/100 g), zeaxanthin (2.8979100 mg/100 g), asta-xanthin (1.3826700 mg/100 g), beta-cryptoxanthin (0.3527960 mg/100 g), neo-xanthin (0.3501600 mg/100 g), malvidin (0.3150850 mg/100 g), anthera-xanthin (0.0063927 mg/100 g) and lycopene (0.0010883 mg/100 g). The phenolic acid constituents found were ferulic acid (0.1370260 mg/100 g), vanillic acid (0.1168070 mg/100 g), ellagic acid (0.0049325 mg/100 g), piperic acid (0.0015819 mg/100 g), syringic acid (0.0005970 mg/100 g) and rosmarinio acid (0.0005967 mg/100 g). Hydroxycinnamic acids detected were caffeic acid (3.3525900 mg/100 g), p-coumaric acid (2.2189400 mg/100 g), o-coumaric acid (0.0042574 mg/100 g), coumarin (0.0027936 mg/100 g), cinnamic acid (0.0012745 mg/100 g), and sinapinic acid (0.0003049 mg/100 g). While tannic acid (162.86 mg/100 g) was, the only tannin found in the leaves of Salacia senegalensis.

Abstract A52: Characterization of Indian honey and its anticancerous activity against colon cancer

Abstract Four multifloral honey types from different Indian origin (named as Samples A, B, C and D) were analyzed for their phenolic acids using high performance liquid chromatography (HPLC). HPLC-Mass Spectroscopy analysis revealed that dihydroxy benzoic acid, caffeic acid, ferulic acid and cinnamic acid were the major phenolic acid constituents of the tested honey. The total antioxidant potential and free radical scavenging ability varied among the honey samples and exhibited a significant correlation with their phenolic content. Further the honey samples were studied for rheology and thermal properties. Controlled shear rate viscometry indicated the Newtonian behavior (a drop in the viscosity as the temperature increases) in the honey samples. Differential Scanning Calorimetry (DSC) analysis revealed the inflection transition temperature (Tg) of the honey samples ranged between - 51.40 °C to −30.64 °C. Thiazolyl blue tetrazolium bromide (MTT) assay revealed that the honey samples containing higher phenolic content showed significant antiproliferative effect against colon cancer cells. From the abovesaid experiments, Sample C among the four was found to be better based on its phenolic, antioxidant and antiproliferative effects and chosen for further studies. Honey induced the apoptotic signal via initial depletion of intracellular non protein thiols, consequently reducing the mitochondrial membrane potential (MMP) and increased the reactive oxygen species (ROS) generation. P53 up-regulation and modulation of pro and antiapoptotic proteins were observed in the honey induced apoptosis. The work was extended further to study the constituents of honey that induced apoptosis. For this, we screened the antiproliferative effect of some reported phenolic constituents namely p-coumaric acid, caffeic acid, gallic acid and eugenol in colon cancer cells. We had selected eugenol based on their better antiproliferative nature and elucidated the mechanism. Eugenol treatment resulted in reduction of intracellular non-protein thiols and increase in the earlier lipid layer break. Further events like dissipation of mitochondrial membrane potential and generation of ROS were accompanied in the eugenol-induced apoptosis. Finally we had studied the anticancer activity of honey samples (Samples B and C) and eugenol against Ehrlich ascites carcinoma. We found that Sample C remarkably inhibited the tumor growth by 40 % compared to Sample B (12.17 %) against Ehrlich ascites carcinoma when given 25% v/v intraperitoneally (i/p). We had found eugenol with a dose of 100 mg/Kg showed nearly 29% tumor inhibition. Citation Information: Cancer Prev Res 2010;3(1 Suppl):A52.

Quantification of flavan-3-ols and phenolic acids in milk-based food products by reversed-phase liquid chromatography–tandem mass spectrometry

This article reports the development and validation of a liquid chromatography–tandem mass spectrometry (LC–MS/MS) method for the comprehensive quantification of flavan-3-ol and phenolic acid constituents of milk-based food products. Isotope dilution-based sample preparation consisted of protein precipitation using acidic methanol enriched with the stable isotope labelled internal standards and ultrafiltration to preserve overall polyphenol composition, but to eliminate milk proteins in order to comply with LC. Reversed-phase liquid chromatography was optimized to achieve separation of 22 analytes in 8 min in order to reduce suppression effects, achieve a wide dynamic range and, most importantly, to resolve isomeric compounds. Negative-ion electrospray mass spectrometric detection and fragmentation of analytes was optimized, final transitions were selected for maximized selectivity, reliable quantification and reduction of false positives. The quantitative performance of the method was validated, the main features include: (1) range of lower limits of detection 5–15 ng/mL for flavan-3-ols, 60–100 ng/mL for procyanidins, 1–60 ng/mL for other phenolic acids, (2) lower limits of quantification 15–45 ng/mL for flavan-3-ols, 200–300 ng/mL for procyanidins, 3–200 ng/mL for other phenolic acids, (3) averaged intra-day precision 9.5%, (4) calibrated range 60–300,000 ng/mL for flavan-3-ols, 900–900,000 ng/mL for procyanidins, 9–225,000 ng/mL for other phenolic acids, (5) averaged accuracy 99.5%. Applications for yoghurt and ice-cream products are given. The presented data suggest that this method will help to better characterize the polyphenol composition of milk-based food products for quality control, assessment of dietary intake and for polyphenol bioavailability/bioefficacy studies.

Total Phenolic Contents and Phenolic Acid Constituents in 4 Varieties of Bitter Melons (Momordica charantia) and Antioxidant Activities of their Extracts

(CG), and China white (CW G), and China white (CW G), and China white (CW G), and China white (CW CAE/g, r CAE/g, r CAE/g, respectively. The total phenolic contents of IG, IW The total phenolic contents of IG, IW The total phenolic contents of IG, IW The total phenolic contents of IG, IW The total phenolic contents of IG, IW, CG, and CW w G, and CW w G, and CW w G, and CW w G, and CW wer y w y w y w y weight basis eight basis eight basis eight basis eight basis, respectively, while in inner tissues w , while in inner tissues w , while in inner tissues w , while in inner tissues w , while in inner tissues wer er er difference in the antioxidant activities of the extracts among varieties ( difference in the antioxidant activities of the extracts among varieties ( difference in the antioxidant activities of the extracts among varieties ( difference in the antioxidant activities of the extracts among varieties (P = 0.2556) and between drying methods ( = 0.2556) and between drying methods ( = 0.2556) and between drying methods ( = 0.2556) and between drying methods ( = 0.2556) and between drying methods (P = 0.1444). The antioxidant activities of flesh, inner tissue, and seed ranged from 81.7% to 86.5%, 78.8% to 88.4%, = 0.1444). The antioxidant activities of flesh, inner tissue, and seed ranged from 81.7% to 86.5%, 78.8% to 88.4%, = 0.1444). The antioxidant activities of flesh, inner tissue, and seed ranged from 81.7% to 86.5%, 78.8% to 88.4%, = 0.1444). The antioxidant activities of flesh, inner tissue, and seed ranged from 81.7% to 86.5%, 78.8% to 88.4%, = 0.1444). The antioxidant activities of flesh, inner tissue, and seed ranged from 81.7% to 86.5%, 78.8% to 88.4%, and 78.5% to 85.4% inhibition, r and 78.5% to 85.4% inhibition, r and 78.5% to 85.4% inhibition, r and 78.5% to 85.4% inhibition, r and 78.5% to 85.4% inhibition, respectiv espectiv espectiv espectively ely ely ely. Bitter melon is a r itter melon is a r itter melon is a r itter melon is a r

Phenolic Acid Content and Composition of Eggplant Fruit in a Germplasm Core Subset

Eggplant (Solanum melongena L.) is ranked among the top ten vegetables in terms of oxygen radical absorbance capacity due to its fruit's phenolic constituents. Several potential health promoting effects have been ascribed to plant phenolic phytochemicals. We report here a first evaluation of phenolic acid constituents in eggplant fruit from accessions in the USDA eggplant core subset. The core subset includes 101 accessions of the cultivated eggplant, S. melongena, and 14 accessions representing four related eggplant species, S. aethiopicum L., S. anguivi Lam., S. incanum L., and S. macrocarpon L. Significant differences in phenolic acid content and composition were evident among the five eggplant species and among genotypes within species. Fourteen compounds separated by HPLC, that were present in many but not all accessions, were identified or tentatively identified as hydroxycinnamic acid (HCA) derivatives based on HPLC elution times, UV absorbance spectra, ES-—MS mass spectra, and in some cases proton NMR data. These phenolics were grouped into five classes: chlorogenic acid isomers, isochlorogenic acid isomers, hydroxycinnamic acid amide conjugates, unidentified caffeic acid conjugates, and acetylated chlorogenic acid isomers. Among S. melongena accessions, there was a nearly 20-fold range in total HCA content. Total HCA content in S. aethiopicum and S. macrocarpon was low relative to S. melongena. A S. anguivi accession had the highest HCA content among core subset accessions. Chlorogenic acid isomers ranged from 63.4% to 96% of total HCAs in most core accessions. Two atypical accessions, S. anguivi PI 319855 and S. incanum PI500922, exhibited strikingly different HCA conjugate profiles, which differed from those of all other core subset accessions by the presence of several unique phenolic compounds. Our findings on eggplant fruit phenolic content provide opportunities to improve eggplant fruit quality and nutritive value.

Chemical analysis of lignocellulose materials

An improved methodology using 80% aqueous ethanol for effective and non-destructive removal from lignocellulosic materials of extractives for quantification (or prior to further analytical characterization) and for analysis of starch and fibre components in the residue is described, and some applications are given. Starch is removed or analyzed by an enzymatic system containing a thermostable α-amylase in combination with an amyloglucosidase. Sugar constituents in the non-starch polysaccharides are analyzed by gas liquid chromatography (GLC) (alternatively as alditol acetates or by a new direct acetylation procedure), uronic acid constituents by decarboxylation, and lignin gravimetrically. Acetyl and phenolic acid constituents on hemicellulose or other cell wall polymers are determined by GLC or high performance liquid chromatography (HPLC) after alkaline treatment.