Hydroxycinnamic Acid Derivatives Research Articles

Comparative Study of the Stilbenes and Other Phenolic Compounds in Cabernet Sauvignon Wines Obtained from Two Different Vinifications: Traditional and Co-Inoculation

From grape cultivation to ripening and harvest timing to processing, each step of the winemaking process can be a critical point when it comes to wine quality and phenolic composition. In this study, the influence of winemaking technology on resveratrol and quercetin content, as well as other polyphenolic compounds, was investigated. Resveratrol is a non-flavonoid polyphenolic stilbene synthesized by grape skin when damaged by infectious diseases or ionizing radiation. Quercetin is a phenol found in grape skins and stems and is produced to protect grapes from UV light damage. Trans-resveratrol and quercetin are known to act as antioxidants, reduce the risk of atherosclerosis and type 2 diabetes, inhibit the growth of cancer cells, and prevent the release of allergic and inflammatory molecules. However, the question was whether red wine could be enriched with these phenols using a co-inoculation winemaking technology. The main new idea was to completely replace the cold maceration process with maceration with the addition of wild yeast (Torulaspora delbrueckii, Td). Maceration with the addition of wild yeast (Td) offers the following advantages over traditional cold maceration: (1) higher concentrations of trans-resveratrol (>35–40%) and quercetin (>35–40%) in the final wine, (2) the new wine has a higher potential for human health, (3) the wine has better aroma and stability due to the higher mannoprotein content, and (4) better energy efficiency in the production process. The study of stability during storage and aging also included derivatives of benzoic acid and hydroxycinnamic acid, piceid, catechin, naringenin, rutin, kaempherol, hesperetin, and anthocyanins. This study found that younger wines had higher phenolic content, while storage of the wine resulted in a decrease in total phenolic content, especially monomeric stilbenes and quercetin. This study represents a small part of the investigation of the influence of non-Saccharomyces yeasts on the phenolic profile of wine, which still requires extensive research with practical application. In addition, non-Saccharomyces yeasts such as Kluyveromyces thermotolerans, Candida stellata, and Metschnikowia pulcherrima could also be used in future studies.

Berberis vulgaris L. Root Extract as a Multi-Target Chemopreventive Agent against Colon Cancer Causing Apoptosis in Human Colon Adenocarcinoma Cell Lines.

Berberis vulgaris L. (Berberidaceae) is a shrub that has been widely used in European folk medicine as an anti-inflammatory and antimicrobial agent. The purpose of our study was to elucidate the mechanisms of the chemopreventive action of the plant's methanolic root extract (BVR) against colon cancer cells. Studies were conducted in human colon adenocarcinoma cell lines (LS180 and HT-29) and control colon epithelial CCD841 CoN cells. According to the MTT assay, after 48 h of cell exposure, the IC50 values were as follows: 4.3, 46.1, and 50.2 µg/mL for the LS180, HT-29, and CCD841 CoN cells, respectively, showing the greater sensitivity of the cancer cells to BVR. The Cell Death Detection ELISAPLUS kit demonstrated that BVR induced programmed cell death only against HT-29 cells. Nuclear double staining revealed the great proapoptotic BVR properties in HT-29 cells and subtle effect in LS180 cells. RT-qPCR with the relative quantification method showed significant changes in the expression of genes related to apoptosis in both the LS180 and HT-29 cells. The genes BCL2L1 (126.86-421.43%), BCL2L2 (240-286.02%), CASP3 (177.19-247.83%), and CASP9 (157.99-243.75%) had a significantly elevated expression, while BCL2 (25-52.03%) had a reduced expression compared to the untreated control. Furthermore, in a panel of antioxidant tests, BVR showed positive effects (63.93 ± 0.01, 122.92 ± 0.01, and 220.29 ± 0.02 mg Trolox equivalents (TE)/g in the DPPH•, ABTS•+, and ORAC assays, respectively). In the lipoxygenase (LOX) inhibition test, BVR revealed 62.60 ± 0.87% of enzyme inhibition. The chemical composition of BVR was determined using a UHPLC-UV-CAD-MS/MS analysis and confirmed the presence of several known alkaloids, including berberine, as well as other alkaloids and two derivatives of hydroxycinnamic acid (ferulic and sinapic acid hexosides). The results are very promising and encourage the use of BVR as a comprehensive chemopreventive agent (anti-inflammatory, antioxidant, and pro-apoptotic) in colorectal cancer, and were widely discussed alongside data from the literature.

Exploring the anti-osteoporosis potential of Petroselinum crispum (Mill.) Fuss extract employing experimentally ovariectomized rat model and network pharmacology approach

One of the most prevalent secondary osteoporosis is ovariectomy-induced osteoporosis. Parsley (Petroselinum crispum) has potent estrogenic and antioxidant properties and was used traditionally in the treatment of amenorrhea and dysmenorrhea. The present study aimed to characterize parsley leaf extract (PLE) employing RP-HPLC-MS-MS/MS-based method and possible protective effect in ovariectomized (OVX)-induced osteoporosis in rats was assessed. Rats were randomly assigned into SHAM group, OVX group, PLE + OVX group (150 mg/kg/day, p.o), and estradiol benzoate (E2) + OVX group (30 μg/kg/day, s.c). After eight weeks following ovariectomy, biomarkers of bone strength, bone resorption, oxidative stress and histopathology were carried out. A network pharmacology approach investigated the key targets and potential mechanisms by of PLE metabolites against osteoporosis using databases: PubChem, BindingDB server, DisGeNET, ShinyGO, and KEGG Pathway. Moreover, FunRich 3.1.3, Cytoscape 3.10.0, and MOE 2019.0102 softwares were used for network pharmacology analysis and molecular docking studies.Flavones and hydroxycinnamic acid derivatives were predominant among 38 metabolites in PLE. It significantly restored bone strength and bone resorption biomarkers, osteocalcin (OST), oxidative stress biomarkers and histopathological alterations. The employed network pharmacology approach revealed that 14 primary target genes were associated with decreasing the severity of osteoporosis. Molecular docking revealed that cGMP-PKG signaling pathway has the highest fold enrichment and its downstream PDE5A. Luteolin, diosmetin, and isorhamnetin derivatives affected mostly osteoporosis targets. PLE exhibited protective action against ovariectomy-induced osteoporosis in rats and may be a promising therapy for premenopausal bone loss. cGMP-PKG signaling pathway could be a promising target for PLE in treating osteoporosis.

Qualitative Metabolite Profiling of Orchis purpurea Huds. by GC and UHPLC/MS Approaches.

Orchids are experiencing wide success in ornamental, medicinal, and food fields. The reason for their success is correlated with both their morphology and metabolomics, the latter linked to their taste and biological effects. Despite many orchids having already been the subject of chemotaxonomic works, some of them are still untapped, like the case of Orchis purpurea. O. purpurea is one of the most common species of the genus Orchis, present in hedgerows, verges, and light woodland, where it is one of the few herbaceous plants able to be unpleasant to herbivorous animals. Essential oil from roots, stems, leaves, and flowers were analyzed via GC/MS analyses, revealing the presence of 70 compounds, with a clear prevalence of coumarin. The high concentration of this metabolite may explain the resistance of O. purpurea to herbivores, being associated with appetite-suppressing properties and a bitter taste. Non-volatile fractions were analyzed via UHPLC-MS analysis revealing the presence of hydroxycinnamic acid derivatives, polyphenols, and glycosidic compounds, probably responsible for their color and fragrance. Taken together, the herein presented results shed light on both the defensive strategy and the chemotaxonomy of O. purpurea.

UHPLC-HRMS-based profiling and simultaneous quantification of the hydrophilic phenolic compounds from the aerial parts of Hypericum aucheri Jaub. & Spach (Hypericaceae)

A validated UHPLC-HRMS method was developed to identify and quantify polar phenolic metabolites in the EtOH extract from H. aucheri Jaub. & Spach’s aerial parts. The external standards, chlorogenic acid, mangiferin, and hyperoside were selected in this analysis. Forty-four compounds, encompassing hydroxybenzoic and hydroxycinnamic acids derivatives, benzophenones, catechins, xanthones, flavonols, biflavones, and chromones were detected and quantified in the aerial parts of the titled plant. Pentahydroxyxanthone-C-glycoside 15, maclurin-O-(benzoyl)-hexoside 37, norathyriol-O-(benzoyl)-hexosides 38 and 42 were suggested to be new natural compounds, while maclurin-O-hexoside 2 was reported for the first time for Hypericum genus. Additionally, more than 22 secondary metabolites, including benzophenones, hydroxycinnamic acid derivatives, catechins, and a chromone, were identified for the first time in H. aucheri. The amounts of the detected metabolites were calculated relative to external standards. The dominant polar phenolic constituents were chlorogenic acid (11.55 mg/g D.W.) and mangiferin (9.13 mg/g D.W.).

Yeast Bioflavoring in Beer: Complexity Decoded and Built up Again

Yeast is a powerful bioflavoring platform, suitable to confer special character and complexity to beer aroma. Enhancing yeast bioflavoring represents a chance for the brewing production chain to diversify its product portfolio and to increase environmental sustainability in the era of climate change. In flavor compound metabolism, multiple genes encoding biosynthetic enzymes and the related regulatory factors are still poorly known, but significant advances have been recently made to dissect gene contribution in flavor molecule production. Furthermore, causative mutations responsible for the huge strain diversity in yeast bioflavoring aptitude have been recently disclosed. This review covers the most recent advances in the genetics of yeast bioflavoring, with special regards to higher alcohols, esters, monoterpene alcohols, thiols, and phenolic derivatives of hydroxycinnamic acids. We also critically discussed the most significant strategies to enhance yeast bioflavoring, including bioprospecting for novel Saccharomyces and non-Saccharomyces strains, whole-genome engineering, and metabolic engineering.

Phenolic Compounds in Berries of Winter-Resistant Actinidia arguta Miq. and Actinidia kolomikta Maxim.: Evidence of Antioxidative Activity.

Variations between fruit cultivars can significantly impact their biochemical composition. The present research examined the variability in the qualitative and quantitative content of phenolic compounds in berry extracts of Actinidia kolomikta and Actinidia arguta cultivars. Additionally, antioxidant activities of berry extracts were evaluated. The total phenolic, flavonoid, proanthocyanidin contents and hydroxycinnamic acid derivatives were determined using the appropriate methodologies. The average amount of phenolic compounds in A. kolomikta berries (177.80 mg/g) was three times higher than that of A. arguta (54.45 mg/g). Our findings revealed that berries of A. kolomikta and A. arguta accumulated, on average, 1.58 RE/g DW (rutin equivalent/g dry weight) and 0.615 mg RE/g DW of total flavonoids, 1439.31 mg EE/g DW (epicatechin equivalent/g dry weight) and 439.97 mg EE/g DW of proanthocyanidins, and 23.51 mg CAE/g DW (chlorogenic acid equivalent/g dry weight) and 5.65 mg CAE/g DW of hydroxycinnamic acid derivatives, respectively. The cultivars of both species were characterized by higher antioxidant activity of total phenolic compounds determined using CUPRAC and FRAP methods compared to the ABTS•+ method. The variability in phenolic compounds' qualitative and quantitative content in tested berry extracts was evaluated by applying ultra-high performance liquid chromatography (UHPLC) coupled to mass spectrometry in tandem with electrospray ionization. Significant intraspecific differences in the amounts of total phenolic compounds, total flavonoid compounds, proanthocyanidins, and hydroxycinnamic acid derivatives were determined among cultivars. Four phenolic acids, eight flavonols, two flavones, and five flavon-3-ols were identified in the berry extracts.

Polyphenols profile and in vitro biological activities of black goji berries (Lycium ruthenicum Murr.)

BACKGROUND: Due to the presence of wide-range phytochemicals, particularly anthocyanins, and their health-promoting activities, black goji fruits (Lycium ruthenicum Murr., LRf) gained attention as functional foods or nutraceuticals. However, data on the phytochemical composition and bioactivities of LRf from outside Asian countries are very limited. OBJECTIVE: This study reports the polyphenols profile and in vitro biological activities of LRf cultivated in the southern part of Serbia. METHODS: The total content of polyphenols, flavonoids and anthocyanins of LRf was determined spectrophotometrically, while the polyphenol profile was evaluated by LC-DAD-ESI-MS. Antioxidant and enzyme-inhibitory potentials against α-amylase, α-glucosidase, acetylcholinesterase, tyrosinase, and 15-lipoxygenase properties were determined spectrophotometrically. The prebiotic potential was assessed by the broth microdilution method. RESULTS: Chromatographic analysis confirmed that hydroxycinnamic acid derivatives and acylated anthocyanins were the predominant polyphenols of LRf. In addition to antioxidative activities, Lycium ruthenicum methanol extract (LRe) showed inhibitory effects against all tested enzymes (IC50 = 5.28–7.28 mg/mL). Prebiotic potential on the growth of various microorganisms’ species was observed, with a marked effect on the growth of yeast Saccharomyces boulardii. CONCLUSIONS: The polyphenol pattern of LRf cultivated in Serbia corresponds with the literature data. Observed bioactivities support further phytochemical characterizations of LRf and investigations of their health-promoting effects, especially prebiotic properties.

Identification and quantification of flavonoids and hydroxycinnamic acids in yellow wood anemone (<i>Anemone ranunculoides</i> L.) by UHPLC-DAD-HESI/MS analysis

Introduction. Yellow wood anemone (Anemone ranunculoides L.) is a herbaceous perennial. This plant grows in the European parts of Russia, Ciscaucasia, Siberia, Central Europe and other regions. It has many different pharmacological activities: immunomodulatory, sedative, anti-inflammatory, antitoxic, diuretic, antibacterial, antioxidant, antitumor and antirheumatic activity. These various effects are due to their biologically active compounds, which include ephemeroids, protoanemonin, saponins, tannins, resins, ascorbic acid, ranunculin, oils lipids and triterpene glycosides. As to phenolic compounds, currently there is no sufficient information on flavonoids and hydroxycinnamic acids (HCAs) profiles in different species of genus Anemone. Because these groups of compounds are quite specific for yellow wood anemone, their detailed study seems to be relevant.Aim. The objective of this research is to identify and quantify flavonoids, HCAs, and their conjugates in Yellow wood anemone leaves, flowers and rhizomes with roots.Materials and methods. The identification was carried out by using ultra-high-performance liquid chromatography with diode array and electrospray ionization-mass spectrometric detection (UHPLC–DAD–ESI-MS) with quantification of individual compounds by external calibration method.Results and discussion. Among the 47 compounds, 30 flavonoids and 17 derivatives of HCAs were detected. Quercetin glycosides were found to be the major flavonoids in aerial parts whereas chalcone glycosides – in underground parts. The major HCA in rhizomes with roots was feruloyltartaric acid (1.18 mg/g) whereas chlorogenic acid was predominant in leaves and flowers (8.68 mg/g and 2.62 mg/g accordingly). The total content of phenolic compounds was estimated at 60 mg/g on a dry weight basis.Conclusion. As a result of the research a detailed profile of flavonoids and HCAs acids of anemon was described. The data obtained can serve to identify this species in the standardization of medicinal plant materials and taxonomic studies.

Sustainable Chemical Derivatization of Hydroxycinnamic Acids

AbstractGreen solvents like ethyl acetate and acetone convert hydroxycinnamic acids into natural and unnatural derivatives such as amides, esters, and other valuable synthetic intermediates. Employing as protection‐activation a system based on an alkyl chloroformate and N‐methyl morpholine, ethyl acetate emerges as an excellent solvent for coupling O‐carbonate‐protected mixed anhydrides in acylation reactions of C‐protected amino acids, amines, and catalyzed acylation of alcohols. This results in high yields of O‐protected phenolic amides and esters. Acetone is preferred for acyl nucleophilic substitution reactions involving ionic species like free amino acids, sodium azide, and sodium hydroxide, all added in water. This approach releases the resultant O‐protected acylation products. Free phenolic compounds are promptly obtained on demand through carbonate deprotection. This synthetic method offers a simplified procedure and employs low‐cost reagents to prepare natural and unnatural hydroxycinnamic acid derivatives.

Changes in Chemical Composition of Red and Black Currant Fruits and Leaves During Berry Ripening

ABSTRACT The composition and variations of sugars, organic acids and phenolic compounds of red and black currant fruits and leaves were studied during the last four weeks of ripening. The results showed that sugar content increased during berry ripening in both species. In comparison, organic acids decreased in red currant, whereas no differences between sampling dates were observed in black currant. Forty-seven individual phenolic compounds, belonging to anthocyanins, flavonols, flavanols, hydroxycinnamic acid derivatives and flavanones were identified in red currant fruits and 52 in black currant fruits by HPLC-MS analysis. In black currant fruits, the major phenolic compounds were anthocyanins (81.51–85.15% of total phenolics), which increased during ripening until the last sampling date. In both red and black currant leaves, 47 phenolic compounds were identified. The content of phenolic compounds in red currant leaves was 1.31-fold to 1.90-fold higher compared to the content in black currant leaves. The most abundant phenolics in both currant leaves were flavonol glycosides, accounting for 58.5–67.9% of total phenolics, and their content was the highest at the end of berry ripening.

ИЗМЕНЕНИЕ ИНДИВИДУАЛЬНО-ГРУППОВОГО СОСТАВА ПОЛИФЕНОЛОВ В ЛИСТЬЯХ РАСТЕНИЙ LONICERA CAERULEA SUBSP. ALTAICA (CAPRIFOLIACEAE) В ВЫСОТНОМ ГРАДИЕНТЕ

Comparative analysis of the variability of quantitative indicators of the individual-group composition of biologically active phenolic compounds in leaf extracts of the resource species L. caerulea subsp. altaica (Caprifoliaceae Juss.) was carried out. Sampling for the study was carried out in the cenopopulations of the Altai Mountains in the valley of the Multa River, in the altitudinal gradient. Eighteen polyphenols were identified by high performance liquid chromatography in extracts from the leaves of L. caerulea subsp. altaica. Luteolin-7-glucoside is the main component among them. The content of individual classes of phenolic compounds in extracts from the leaves of L. caerulea subsp. altaica in the altitude profile varied significantly: hydroxycinnamic acid derivatives – 3.3-4.8 mg/g, flavonols – 6.6-12.1 mg/g, flavones – 13.6-29.6 mg/g. A significant increase in the total content of polyphenols and luteolin-7-glucoside in extracts from the leaves of L. caerulea subsp. altaica was noted above and below the limits of the optimum distribution of this plant in the vertical gradient. Positive statistically significant correlations of flavones and the total content of phenolic compounds with the height of plant growth are established within 1200–1850 meters above sea level. The content of flavonols and hydroxycinnamic acids, on the contrary, decreased with increasing altitude.

Chemical, sensory and biological variations of black tea under different drying temperatures

As the final processing step, drying temperature between 90 and 140 ℃ is usually applied to terminate enzymatic activities and improve sensory characteristics of black tea. Liquid chromatography tandem mass spectrometry (LC-MS) based non-targeted and targeted metabolomics analyses combined in vitro biological assays were adopted to investigate the chemical and biological variations after drying. Fifty-nine differentially expressed metabolites including several hydroxycinnamic acid derivatives and pyroglutamic acid–glucose Amadori rearrangement products (ARPs) were identified, the latter of which was correspondingly accumulated with increasing temperature. The levels of theaflavins (TFs), thearubigins (TRs), monosaccharides and free amino acids gradually decreased with increasing temperature. Furthermore, the bioassays of black tea showed that drying under 110 ℃ provided the highest antioxidant capacities, but the inhibitory effects on α-glucosidase and α-amylase were decreasing along with increasing drying temperature. These results are valuable for optimizing drying process to obtain superior sensory properties and preserve bioactivities of black tea.

Data-Driven Characterization of Metabolome Reprogramming during Early Development of Sorghum Seedlings.

Specialized metabolites are produced via discrete metabolic pathways. These small molecules play significant roles in plant growth and development, as well as defense against environmental stresses. These include damping off or seedling blight at a post-emergence stage. Targeted metabolomics was followed to gain insights into metabolome changes characteristic of different developmental stages of sorghum seedlings. Metabolites were extracted from leaves at seven time points post-germination and analyzed using ultra-high performance liquid chromatography coupled to mass spectrometry. Multivariate statistical analysis combined with chemometric tools, such as principal component analysis, hierarchical clustering analysis, and orthogonal partial least squares-discriminant analysis, were applied for data exploration and to reduce data dimensionality as well as for the selection of potential discriminant biomarkers. Changes in metabolome patterns of the seedlings were analyzed in the early, middle, and late stages of growth (7, 14, and 29 days post-germination). The metabolite classes were amino acids, organic acids, lipids, cyanogenic glycosides, hormones, hydroxycinnamic acid derivatives, and flavonoids, with the latter representing the largest class of metabolites. In general, the metabolite content showed an increase with the progression of the plant growth stages. Most of the differential metabolites were derived from tryptophan and phenylalanine, which contribute to innate immune defenses as well as growth. Quantitative analysis identified a correlation of apigenin flavone derivatives with growth stage. Data-driven investigations of these metabolomes provided new insights into the developmental dynamics that occur in seedlings to limit post-germination mortality.

Two gene clusters and their positive regulator SlMYB13 that have undergone domestication-associated negative selection control phenolamide accumulation and drought tolerance in tomato

Among plant metabolites, phenolamides, which are conjugates of hydroxycinnamic acid derivatives and polyamines, play important roles in plant adaptation to abiotic and biotic stresses. However, the molecular mechanisms underlying phenolamide metabolism and regulation as well as the effects of domestication and breeding on phenolamide diversity in tomato remain largely unclear. In this study, we performed a metabolite-based genome-wide association study and identified two biosynthetic gene clusters (BGC7 and BGC11) containing 12 genes involved in phenolamide metabolism, including four biosynthesis genes (two 4CL genes, one C3H gene, and one CPA gene), seven decoration genes (five AT genes and two UGT genes), and one transport protein gene (DTX29). Using gene co-expression network analysis we further discovered that SlMYB13 positively regulates the expression of two gene clusters, thereby promoting phenolamide accumulation. Genetic and physiological analyses showed that BGC7, BGC11 and SlMYB13 enhance drought tolerance by enhancing scavenging of reactive oxygen species and increasing abscisic acid content in tomato. Natural variation analysis suggested that BGC7, BGC11 and SlMYB13 were negatively selected during tomato domestication and improvement, leading to reduced phenolamide content and drought tolerance of cultivated tomato. Collectively, our study discovers a key mechanism of phenolamide biosynthesis and regulation in tomato and reveals that crop domestication and improvement shapes metabolic diversity to affect plant environmental adaptation.

Theory and experiment on the terahertz vibrational spectrum of ferulic acid

Ferulic acid (FA, C10H10O4), a type of hydroxycinnamic acid derivative, has beneficial pharmacological effects and biological activities and is known for its high application value in medicine, health care, and cosmetic products. The vibration spectrum of FA ranging from 0.3 THz to 2.0 THz has been investigated by terahertz time-domain spectroscopy. The characteristic absorption peaks located at 0.937, 1.159, 1.464, 1.694, and 1.910 THz are obtained experimentally. To understand the origin of the characteristic absorption peaks of FA, density functional theory calculations based on isolated molecule and crystalline structure are separately performed to differentiate the intramolecular and intermolecular vibrational modes. Combined analysis of the experimental and theoretical results informs that the characteristic absorption peak at 1.464 THz comes from intramolecular interaction, and the ones at 0.937, 1.159, 1.694, and 1.910 THz originate from intermolecular collective vibrational modes.

Phytochemical Profiles and Biological Activities of Plant Extracts from Aromatic Plants Cultivated in Cyprus.

Medicinal and aromatic plants' properties, still an interesting research area, are attributed to the presence of various specialized products that possess important pharmacological activities. In the present study, six medicinal/aromatic plants (Sideritis cypria, Origanum dubium, Melissa officinalis, Mentha piperita, Thymus capitatus, and Salvia fruticosa) were evaluated for their phytochemical and nutritive composition, as well as their biological activities, including antioxidant, antimicrobial, and cytotoxic properties. The results obtained indicate that M. piperita was rich in proteins and minerals such as N and Mg, while S. cypria accumulated more K, Na, P, and Ca. The highest content of phenols and flavonoids was observed in M. piperita, followed by O. dubium and T. capitatus, which eventually influenced their high antioxidant capacity. NMR screening revealed the presence of (i) triterpenoids and hydroxycinnamic acid derivatives in M. officinalis; (ii) terpenoids, flavonoids, and phenolic acid derivatives in S. fruticosa; (iii) flavonoids and phenolic acid derivatives in M. piperita; (iv) phenolic monoterpenes in O. dubium and T. capitatus; and (v) terpenoids, flavones, and phenylethanoid glycosides in S. cypria. The results of the antimicrobial activity showed that the tested samples overall had quite good antimicrobial potential. High antibacterial activity was found in O. dubium and T. capitatus, while O. dubium and S. cypria exhibited great antifungal activities. The studied species also had an important effect on the viability of female-derived and colon cancer cells. In particular, in colon cancer cells, the extracts from T. capitatus, M. officinalis, M. piperita, and S. fruticosa exhibited a stronger effect on cell viability in the more metastatic cell line at significantly lower concentrations, indicating an important therapeutic potential in targeting highly metastatic tumors. This finding is worth further investigation. The present study unveiled interesting phytochemical profiles and biological properties of the six medicinal/aromatic plants, which should be further explored, contributing to green chemistry and the possible creation of natural health products for humans' health/nutrition and additives in cosmetics.

A Comprehensive Study on Lathyrus tuberosus L.: Insights into Phytochemical Composition, Antimicrobial Activity, Antioxidant Capacity, Cytotoxic, and Cell Migration Effects.

In this study, in vitro antioxidant, antimicrobial, cytotoxic, and cell migration effects of phenolic compounds of Lathyrus tuberosus leaves, known in the Transylvanian ethnomedicine, were investigated. Ultra-high-performance liquid chromatography-tandem mass spectrometry was employed for the analysis of the ethanolic and aqueous extracts. The antimicrobial properties were determined using a conventional microdilution technique. Total antioxidant capacity techniques were used using cell-free methods and cell-based investigations. Cytotoxic effects were conducted on 3T3 mouse fibroblasts and HaCaT human keratinocytes using a multiparametric method, assessing intracellular ATP, total nucleic acid, and protein levels. Cell migration was visualized by phase-contrast microscopy, employing conventional culture inserts to make cell-free areas. Together, 93 polyphenolic and monoterpenoid compounds were characterized, including flavonoid glycosides, lignans, hydroxycinnamic acid, and hydroxybenzoic acid derivatives, as well as iridoids and secoiridoids. The ethanolic extract showed high antioxidant capacity and strong antimicrobial activity against Bacillus subtilis (MIC80 value: 354.37 ± 4.58 µg/mL) and Streptococcus pyogenes (MIC80 value: 488.89 ± 4.75 µg/mL). The abundance of phenolic compounds and the results of biological tests indicate the potential for L. tuberosus to serve as reservoirs of bioactive compounds and to be used in the development of novel nutraceuticals.

Phenolic compounds in the fruits of Enterolobium cyclocarpum and the inhibition of Haemonchus contortus eggs

The fabacean Enterolobium cyclocarpum is a tree with multiple uses in production systems and its fruits serve as food for livestock, in addition, they contain phenolic compounds. The ovicidal effect of the secondary compounds of the Enterolobium cyclocarpum fruits extracted with hydroalcoholic solvent (HA-E) and the aqueous (Aq-F) and organic (AcOEt-F) fractions was evaluated. Additionally, a phytochemical analysis of the extract and fractions was performed by high performance liquid chromatography (HPLC). The HA-E showed an ovicidal effect close to 100% with the concentration evaluated of the 100 mg/mL. The fractionation of the extract allowed to potentiate the activity in the Aq (94.05% at 12 mg/mL) and AcOEt (99.45% at 3 mg/mL) fractions. The secondary compounds extracted from the fruits of E. cyclocarpum in the HA-E and fractions were flavonols, coumaric and ferulic acids and other derivatives of hydroxycinnamic acid and were responsible for the ovicidal activity observed against H. contortus.

Investigating the binding of caffeic acid to human hemoglobin using multispectroscopic and molecular docking approaches

Caffeic acid (CA) is a hydroxycinnamic acid derivative that possess a wide variety of biological properties and is non-toxic to humans. The binding mechanism of CA with human hemoglobin (HHb) was studied for the first time using multispectroscopic and molecular docking methods. The UV–visible absorption spectra showed that CA interacts with HHb through the formation of ground state complex. The fluorescence studies revealed that CA quenches HHb fluorescence by the static mechanism and confirmed the presence of a single CA binding site on the HHb molecule. The negative values of thermodynamics parameters (ΔH,ΔSand ΔG) showed that the binding of CA to HHb is a spontaneous and exothermic process. Hydrogen bonds and van der Waal interactions are the major intermolecular forces that stabilize the HHb-CA complex. Synchronous fluorescence experiments showed that binding of CA altered the microenvironment around tryptophan residues of HHb. Fluorescence resonance energy transfer studies indicated a high propensity of energy transfer from tryptophan residues of HHb to CA. Circular dichroism spectra and catalytic esterase activity confirmed that only minor changes occur in the secondary structure of HHb in the presence of CA. Molecular docking study identified the HHb amino acid residues involved in binding to CA. Analysis of the binding mode of CA with HHb represents an important step in elucidating the molecular mechanism of the protection of HHb from oxidative damage. This will help in understanding the potential role of CA and related antioxidants as therapeutic agents in various blood-related diseases.