The seed coat serves as the primary protective barrier, offering mechanical and chemical defense for the embryo. It contains various metabolites, including phenolic compounds, which can be oxidized by polyphenol oxidase (PPO) to form oligomers. In this study, we heterologously expressed a 515 amino acid protein derived from wild pea (Pisum elatius), omitting its N-terminal signal sequence, and analyzed its biochemical properties. The recombinant PeaPPO required sodium dodecyl sulfate (SDS) for activation and exhibited activity between pHs 5.2 and 7.0, peaking at pH 6.0 with 0.25 mM SDS. Tropolone and its isomer thujaplicin were the most effective inhibitors. PeaPPO catalyzed reactions with seed coat-derived substrates, displaying activity toward phenols, catechols, and pyrogallols, with the highest affinity for catechols. Principal component analysis of LC-MS/MS-derived phenolic profiles demonstrated that PPO+ and ppo- genotypes differ significantly in their accumulation of PPO substrates and inhibitors. These findings confirm that PeaPPO possesses both monophenolase and catechol oxidase activities, identifying it as a tyrosinase.
- Keywords
- legumes, pea, phenolics, polyphenol oxidase, seeds, tyrosinase,
- MeSH
- Phenols * metabolism chemistry MeSH
- Pisum sativum * enzymology genetics chemistry MeSH
- Catechol Oxidase * metabolism genetics chemistry MeSH
- Kinetics MeSH
- Recombinant Proteins metabolism chemistry genetics MeSH
- Plant Proteins * genetics chemistry metabolism MeSH
- Seeds * enzymology chemistry genetics MeSH
- Substrate Specificity MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Phenols * MeSH
- Catechol Oxidase * MeSH
- Recombinant Proteins MeSH
- Plant Proteins * MeSH
Apremilast (APR) is an anti-inflammatory drug commonly used in the treatment of psoriasis. In efforts to enhance its solubility, several cocrystals with similar structural features have been developed. This study investigates the cocrystallization of APR with four phenolic-type coformers: phenol, catechol, pyrogallol, and hydroxyquinol. These coformers differ in the number and position of their hydroxyl groups, with their melting points varying by as much as 100 °C. Four novel cocrystal forms were synthesized, purified, and characterized using X-Ray diffraction and thermal analysis techniques. Surprisingly, the resulting cocrystals exhibited minimal differences in their melting points. The molecular packing of APR appears to limit the network-forming potential of the hydroxyl groups, a conclusion supported by the solved crystal structures, Hirshfeld surface analysis, and differential scanning calorimetry (DSC) results.
- Keywords
- Apremilast, cocrystals, hydrogen bonds, phenolic compounds, π–π interactions,
- Publication type
- Journal Article MeSH
Determination of the urinary protein-to-creatinine ratio (UPC) is an important tool in the quantification of proteinuria in animals. However, the result may be affected by the different methods of determining the urinary protein concentration. The aim of this study was to compare the turbidimetric method using benzethonium chloride and the colorimetric method using pyrogallol red in the measurement of the urinary protein concentration in dogs, cats, guinea pigs and horses. A total of 464, 192, 216 and 119 urine samples from dogs, cats, guinea pigs and horses were examined in the study, respectively. The group consisted of animals of both sexes and different ages, and, in the dogs and cats, it included both healthy animals and those with various health problems. In the group of horses and guinea pigs, only clinically healthy animals were included. A total of 347, 185, 103 and 100 samples from the dogs, cats, guinea pigs and horses were used in the statistical analysis; the other values were excluded as they were below the detection limit. According to the Passing-Bablok analysis, there was a significant constant and proportional difference in the horses. In the dogs, cats and guinea pigs, there was a significant constant difference, but no proportional difference. The Bland-Altman method showed significant bias between the two methods in the horses and cats, but not in the dogs and guinea pigs. In the dogs and cats, the agreement between the two methods was tested and expressed as Cohen's kappa (κ). In the cats, it was almost perfect for the proteinuric samples (κ = 0.823 3) and significant for the non-proteinuric samples (κ = 0.804 9). In the dogs, the agreement was significant for the non-proteinuric samples (κ = 0.621 5) and only moderate for the proteinuric samples (κ = 0.527 5). The influence of the method used to determine the urinary protein concentration should be taken into account when evaluating the UPC. Repeated examinations in one patient should be performed with the same method.
- Keywords
- UPC, cat, dog, guinea pig, horse, proteinuria,
- Publication type
- Journal Article MeSH
In this study, MNPs were functionalized with pyrocatechol (CAT), pyrogallol (GAL), caffeic acid (CAF), and nitrodopamine (NDA) at pH 8 and pH 11. The functionalization of the MNPs was successful, except in the case of NDA at pH 11. The thermogravimetric analyses indicated that the surface concentration of the catechols was between 1.5 and 3.6 molecules/nm2. The saturation magnetizations (Ms) of the functionalized MNPs were higher than the starting material. XPS analyses showed only the presence of Fe(III) ions on the surface, thus refuting the idea of the Fe being reduced and magnetite being formed on the surfaces of the MNPs. Density functional theory (DFT) calculations were performed for two modes of adsorption of CAT onto two model surfaces: plain and adsorption via condensation. The total magnetization of both adsorption modes remained the same, indicating that the adsorption of the catechols does not affect the Ms. The analyses of the size and the size distribution showed an increase in the average size of the MNPs during the functionalization process. This increase in the average size of the MNPs and the reduction in the fraction of the smallest (i.e., <10 nm) MNPs explained the increase in the Ms values.
- Keywords
- DFT, XPS, adsorption, catechols, magnetic nanoparticles, magnetic properties,
- Publication type
- Journal Article MeSH
Medicinal plants are rich sources of valuable molecules with various profitable biological effects, including antimicrobial activity. The advantages of herbal products are their effectiveness, relative safety based on research or extended traditional use, and accessibility without prescription. Extensive and irrational usage of antibiotics since their discovery in 1928 has led to the increasing expiration of their effectiveness due to antibacterial resistance. Now, medical research is facing a big and challenging mission to find effective and safe antimicrobial therapies to replace inactive drugs. Over the years, one of the research fields that remained the most available is the area of natural products: medicinal plants and their metabolites, which could serve as active substances to fight against microbes or be considered as models in drug design. This review presents selected flavonoids (such as apigenin, quercetin, kaempferol, kurarinone, and morin) and tannins (including oligomeric proanthocyanidins, gallotannins, ellagitannins, catechins, and epigallocatechin gallate), but also medicinal plants rich in these compounds as potential therapeutic agents in oral infectious diseases based on traditional usages such as Agrimonia eupatoria L., Hamamelis virginiana L., Matricaria chamomilla L., Vaccinium myrtillus L., Quercus robur L., Rosa gallica L., Rubus idaeus L., or Potentilla erecta (L.). Some of the presented compounds and extracts are already successfully used to maintain oral health, as the main or additive ingredient of toothpastes or mouthwashes. Others are promising for further research or future applications.
- Keywords
- antibiofilm activity, antimicrobial activity, flavonoids, medicinal plants, natural products, oral infections, oral pathogens, tannins,
- MeSH
- Anti-Infective Agents * pharmacology therapeutic use MeSH
- Flavonoids therapeutic use MeSH
- Hydrolyzable Tannins metabolism MeSH
- Communicable Diseases * MeSH
- Plants, Medicinal * metabolism MeSH
- Plant Extracts MeSH
- Tannins metabolism MeSH
- Publication type
- Journal Article MeSH
- Review MeSH
- Names of Substances
- Anti-Infective Agents * MeSH
- Flavonoids MeSH
- Hydrolyzable Tannins MeSH
- Plant Extracts MeSH
- Tannins MeSH
The aim of this work is to determine the biological activity of ellagitannins rich extracts from leaves of raspberry (Rubus idaeus L.) and wild strawberry (Fragaria vesca L.) in relation to cells and cell membranes. Detailed qualitative and quantitative analysis of phenolic compounds of the extract was made using chromatographic methods. Cytotoxic and antioxidant activities of tested extracts in relation to erythrocytes and human vascular endothelial cells (HMEC-1) were determined by using fluorimetric and spectrophotometric methods. In order to establish the influence of the extracts on the physical properties of the membrane, such as osmotic resistance and erythrocytes shapes, mobility and/or hydration of polar heads and fluidity of hydrocarbon chains of membrane lipids, microscopic and spectroscopic methods were used. The results showed that the extracts are non-toxic for erythrocytes and HMEC-1 cells (up to concentration of 50 µg/mL), but they effectively protect cells and their membranes against oxidative damage. The increase in osmotic resistance of erythrocytes, formation of echinocytes and changes only in the polar part of the membrane caused by the extracts demonstrate their location mainly in the hydrophilic part of the membrane. The results indicate that tested extracts have high biological activities and may be potentially used in delaying the ageing process of organisms and prevention of many diseases, especially those associated with oxidative stress.
- Keywords
- Fragaria vesca L., HMEC-1, Rubus idaeus L., bioactivity, cells, cytotoxicity, erythrocytes, membrane, oxidation, raspberry, wild strawberry,
- MeSH
- Antioxidants chemistry pharmacology MeSH
- Endothelial Cells MeSH
- Erythrocytes MeSH
- Hydrolyzable Tannins MeSH
- Fragaria * chemistry MeSH
- Humans MeSH
- Membrane Lipids MeSH
- Oxidative Stress MeSH
- Plant Extracts chemistry pharmacology MeSH
- Rubus * chemistry MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Antioxidants MeSH
- Hydrolyzable Tannins MeSH
- Membrane Lipids MeSH
- Plant Extracts MeSH
The aim of this publication is to compile a summary of the findings regarding punicalagin in various tissues described thus far in the literature, with an emphasis on the effect of this substance on immune reactions. Punicalagin (PUN) is an ellagitannin found in the peel of pomegranate (Punica granatum). It is a polyphenol with proven antioxidant, hepatoprotective, anti-atherosclerotic and chemopreventive activities, antiproliferative activity against tumor cells; it inhibits inflammatory pathways and the action of toxic substances, and is highly tolerated. This work describes the source, metabolism, functions and effects of punicalagin, its derivatives and metabolites. Furthermore, its anti-inflammatory and antioxidant effects are described.
- Keywords
- apoptosis, ellagic acid, immune cells, metabolism, proliferation, punicalagin,
- MeSH
- Anti-Inflammatory Agents pharmacology MeSH
- Biological Availability MeSH
- Hydrolyzable Tannins immunology metabolism MeSH
- Immunosuppressive Agents pharmacology MeSH
- Ellagic Acid analysis MeSH
- Humans MeSH
- Metabolome MeSH
- Animals MeSH
- Check Tag
- Humans MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Review MeSH
- Names of Substances
- Anti-Inflammatory Agents MeSH
- Hydrolyzable Tannins MeSH
- Immunosuppressive Agents MeSH
- Ellagic Acid MeSH
- punicalagin MeSH Browser
Mineralization of hydrogel biomaterials with calcium phosphate (CaP) is considered advantageous for bone regeneration. Mineralization can be both induced by the enzyme alkaline phosphatase (ALP) and promoted by calcium-binding biomolecules, such as plant-derived polyphenols. In this study, ALP-loaded gellan gum (GG) hydrogels were enriched with gallotannins, a subclass of polyphenols. Five preparations were compared, namely three tannic acids of differing molecular weight (MW), pentagalloyl glucose (PGG), and a gallotannin-rich extract from mango kernel (Mangifera indica L.). Certain gallotannin preparations promoted mineralization to a greater degree than others. The various gallotannin preparations bound differently to ALP and influenced the size of aggregates of ALP, which may be related to ability to promote mineralization. Human osteoblast-like Saos-2 cells grew in eluate from mineralized hydrogels. Gallotannin incorporation impeded cell growth on hydrogels and did not impart antibacterial activity. In conclusion, gallotannin incorporation aided mineralization but reduced cytocompatibility.
- Keywords
- composite, enzyme, gellan gum, mineralization, polyphenol, protein-polyphenol interaction,
- MeSH
- Alkaline Phosphatase metabolism MeSH
- Anti-Bacterial Agents pharmacology MeSH
- Polysaccharides, Bacterial MeSH
- Biocompatible Materials MeSH
- Biomimetics methods MeSH
- Calcium Phosphates MeSH
- Calcification, Physiologic drug effects MeSH
- Hydrogels chemistry MeSH
- Hydrolyzable Tannins metabolism pharmacology MeSH
- Humans MeSH
- Mangifera chemistry MeSH
- Minerals chemistry MeSH
- Osteoblasts metabolism MeSH
- Polyphenols chemistry MeSH
- Polysaccharides chemistry MeSH
- Bone Regeneration MeSH
- Plant Extracts chemistry MeSH
- Plants metabolism MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Alkaline Phosphatase MeSH
- Anti-Bacterial Agents MeSH
- Polysaccharides, Bacterial MeSH
- Biocompatible Materials MeSH
- calcium phosphate MeSH Browser
- Calcium Phosphates MeSH
- gellan gum MeSH Browser
- Hydrogels MeSH
- Hydrolyzable Tannins MeSH
- Mangifera indica extract MeSH Browser
- Minerals MeSH
- pentagalloylglucose MeSH Browser
- Polyphenols MeSH
- Polysaccharides MeSH
- Plant Extracts MeSH
Flavonoids are abundant polyphenols in nature. They are extensively biotransformed in enterocytes and hepatocytes, where conjugated (methyl, sulfate, and glucuronide) metabolites are formed. However, bacterial microflora in the human intestines also metabolize flavonoids, resulting in the production of smaller phenolic fragments (e.g., hydroxybenzoic, hydroxyacetic and hydroxycinnamic acids, and hydroxybenzenes). Despite the fact that several colonic metabolites appear in the circulation at high concentrations, we have only limited information regarding their pharmacodynamic effects and pharmacokinetic interactions. Therefore, in this in vitro study, we investigated the interactions of 24 microbial flavonoid metabolites with human serum albumin and cytochrome P450 (CYP2C9, 2C19, and 3A4) enzymes. Our results demonstrated that some metabolites (e.g., 2,4-dihydroxyacetophenone, pyrogallol, O-desmethylangolensin, and 2-hydroxy-4-methoxybenzoic acid) form stable complexes with albumin. However, the compounds tested did not considerably displace Site I and II marker drugs from albumin. All CYP isoforms examined were significantly inhibited by O-desmethylangolensin; nevertheless, only its effect on CYP2C9 seems to be relevant. Furthermore, resorcinol and phloroglucinol showed strong inhibitory effects on CYP3A4. Our results demonstrate that, besides flavonoid aglycones and their conjugated derivatives, some colonic metabolites are also able to interact with proteins involved in the pharmacokinetics of drugs.
- Keywords
- CYP450 enzymes, O-desmethylangolensin, colonic flavonoid metabolites, pharmacokinetic interaction, phloroglucinol, polyphenols, resorcinol, serum albumin,
- MeSH
- Erythrocytes enzymology MeSH
- Flavonoids * chemistry metabolism MeSH
- Hepatocytes enzymology MeSH
- Humans MeSH
- Serum Albumin, Human * chemistry metabolism MeSH
- Cytochrome P-450 Enzyme System * chemistry metabolism MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Flavonoids * MeSH
- Serum Albumin, Human * MeSH
- Cytochrome P-450 Enzyme System * MeSH
In Italy a particularly valuable chestnut is "Marrone di Roccadaspide", a protected geographical indication (PGI) product, deriving from a Castanea sativa cultivar, typical of Salerno province in Campania region. As chestnut industrial processes yield a large amount of shell by-products, in this study the possibility to retrain this waste food as potential source of bioactives was investigated. The ability of "Marrone di Roccadaspide" shell MeOH extract to modulate the pro-inflammatory transcriptional factor NF-κB after LPS stimulation, along with the antioxidant activity by a cell-based in vitro test, were evaluated. To correlate the NF-κB inhibition (67.67% at 5 μg/mL) and the strong antioxidant activity to the chemical composition, an analytical approach based on LC-ESI/LTQOrbitrap/MS/MSn along with NMR characterization of isolated compounds was developed. The identification of hydrolysable and condensed tannins, along with flavonoids, phenol glucosides, ellagic acid derivatives, and triterpenoids was accomplished. The most representative compounds were quantitatively analyzed by LC-ESI/QTrap/MS/MS, showing bartogenic acid as the compound occurring in the highest amount (103.08 mg/100 g shells). With the aim to explore the possibility to employ chestnut shells as suitable source of bioactives for the preparation of functional ingredients, the chemical composition and the antioxidant activity of "eco-friendly" extracts (EtOH and EtOH:H2O 7:3) was finally evaluated, showing a high superimposability of the EtOH:H2O (7:3) extract to the MeOH extract.
- Keywords
- Antioxidant activity, LC-HRMS/MS(n), Shells, Tannins, Triterpenes, “Marrone di Roccadaspide” PGI, “green” extracts,
- MeSH
- Antioxidants analysis MeSH
- Fagaceae chemistry MeSH
- Phenols analysis MeSH
- Flavonoids analysis MeSH
- Glucosides analysis MeSH
- Evaluation Studies as Topic MeSH
- Hydrolyzable Tannins analysis MeSH
- Calibration MeSH
- Ellagic Acid analysis MeSH
- Humans MeSH
- NF-kappa B metabolism MeSH
- Nuts chemistry MeSH
- Proanthocyanidins analysis MeSH
- Cell Proliferation MeSH
- Rationalization * MeSH
- Reactive Oxygen Species MeSH
- Plant Extracts analysis MeSH
- Tandem Mass Spectrometry MeSH
- Tannins analysis MeSH
- Triterpenes analysis MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Geographicals
- Italy MeSH
- Names of Substances
- Antioxidants MeSH
- bartogenic acid MeSH Browser
- Phenols MeSH
- Flavonoids MeSH
- Glucosides MeSH
- Hydrolyzable Tannins MeSH
- Ellagic Acid MeSH
- NF-kappa B MeSH
- Proanthocyanidins MeSH
- Reactive Oxygen Species MeSH
- Plant Extracts MeSH
- Tannins MeSH
- Triterpenes MeSH
