This service exclusively searches for literature that cites resources. Please be aware that the total number of searchable documents is limited to those containing RRIDs and does not include all open-access literature.
A comparative in vitro study of the antioxidant potential of natural phenols (zingerone, curcumin, raspberry ketone, magnolol) and their synthesized derivatives was performed. The antioxidant efficiency was evaluated in blood serum obtained from healthy individuals, by means of spectrophotometry, before and after the addition of pro-oxidant tert-butyl hydroperoxide (TBH). Moreover, the antioxidant effect of an equimolar mixture of curcumin and zingerone was investigated. Interpretation of our results reveals that in the blood serum of healthy individuals curcumin (C1), raspberry ketone (RK1), magnolol (M1) and synthesized derivative of zingerone (Z2) demonstrate remarkable antioxidant effects (p < 0.05). However, in the state of TBH-induced excessive oxidative stress natural magnolol and synthesized derivatives C1, Z1 and RK1 show powerful antioxidant activity and thus can be further investigated to obtain information about their metabolic transformations and their potential influence at the cellular level. Results obtained from measurements in an equimolar mixture of zingerone and curcumin indicate synergism (p < 0.05) between the two compounds. This combination is especially successful due to the fast and efficient neutralization of added pro-oxidant TBH. The commercial availability of turmeric and ginger and their frequent combined use in diet suggest ideas for further broader utilization of the beneficial synergistic effect of their phenolic components.
Natural small-molecule phenols (NSMPs) share some bioactivities. The anxiolytic activity of NSMPs is attracting attention in the scientific community. This paper provides data supporting the hypothesis that NSMPs are generally anxiolytic. The anxiolytic activities of seven simple phenols, including phloroglucinol, eugenol, protocatechuic aldehyde, vanillin, thymol, ferulic acid, and caffeic acid, were assayed with the elevated plus maze (EPM) test in mice. The oral doses were 5, 10 and 20 mg/kg, except for phloroglucinol for which the doses were 2.5, 5 and 10 mg/kg. All tested phenols had anxiolytic activity in mice. The phenolic hydroxyl group in 4-hydroxycinnamic acid (4-OH CA) was essential for the anxiolytic activity in the EPM test in mice and rats compared to 4-chlorocinnamic acid (4-Cl CA). The in vivo spike recording of rats' hippocampal neurons also showed significant differences between 4-OH CA and 4-Cl CA. Behavioral and neuronal spike recording results converged to indicate the hippocampal CA1 region might be a part of the anxiolytic pathways of 4-OH CA. Therefore, our study provides further experimental data supporting NSMPs sharing anxiolytic activity, which may have general implications for phytotherapy because small phenols occur extensively in herbal medicines.
Nutraceutics is a growing research field in which researchers study and attempt to improve the biological properties of metabolites in food. Wine is one of the most consumed products in the world and contains a plethora of molecules biologically relevant to human health. In this article, several polyphenols with potential antioxidant activity were measured in wines from Apulia, in Southeast Italy. Hydroxytyrosol, gallic and syringic acids, luteolin, quercetin, and trans-resveratrol were identified and quantified by HPLC. The amount of the analyzed metabolites in wines were largely dependent on their color, with red ones being the richest compared to white and rose wines. Gallic acid was the most abundant polyphenol, followed by syringic acid and luteolin. Nevertheless, significant amounts of hydroxytyrosol, quercetin, and trans-resveratrol were also found. The average concentration of polyphenols found in these wines could have potential health-promoting effects, especially if consumed in moderate quantities on a regular basis.
Gastrodia elata is a famous traditional Chinese herb with medicinal and edible application. In this study, three new polybenzyls, gastropolybenzylols G-I (1-3) were isolated from the EtOAc extract of G. elata. Their structures were identified by extensive spectroscopic analyses involving HRESIMS, UV, IR, 1D and 2D NMR. Compound 1 showed agonistic effects on MT1 and MT2 receptors with agonistic rates of 55.91±4.84% and 165.13±5.65% at the concentration of 0.5 mM, respectively, and an EC50 value of 76.24 μM on MT2 receptor.
The α-class carbonic anhydrases (CAs, EC 4.2.1.1) from the bacterial pathogens Neisseria gonorrhoeae (NgCAα) and Vibrio cholerae (VchCAα) were investigated for their inhibition by a panel of phenols and phenolic acids. Mono-, di- and tri-substituted phenols incorporating additional hydroxyl/hydroxymethyl, amino, acetamido, carboxyl, halogeno and carboxyethenyl moieties were included in the study. The best NgCAα inhibitrs were phenol, 3-aminophenol, 4-hydroxy-benzylalcohol, 3-amino-4-chlorophenol and paracetamol, with KI values of 0.6-1.7 µM. The most effective VchCAα inhibitrs were phenol, 3-amino-4-chlorophenol and 4-hydroxy-benzyl-alcohol, with KI values of 0.7-1.2 µM. Small changes in the phenol scaffold led to drastic effects on the bacterial CA inhibitory activity. This class of underinvestigated bacterial CA inhibitors may thus lead to effective compounds for fighting drug resistant bacteria.
Combining two pharmacophores in a molecule can lead to useful synergistic effects. Herein, we show hybrid systems that combine sterically hindered phenols with dinitrobenzofuroxan fragments exhibit a broad range of biological activities. The modular assembly of such phenol/benzofuroxan hybrids allows variations in the phenol/benzofuroxan ratio. Interestingly, the antimicrobial activity only appears when at least two benzofuroxan moieties are introduced per phenol. The most potent of the synthesized compounds exhibit high cytotoxicity against human duodenal adenocarcinoma (HuTu 80), human breast adenocarcinoma (MCF-7), and human cervical carcinoma cell lines. This toxicity is associated with the induction of apoptosis via the internal mitochondrial pathway and an increase in ROS production. Encouragingly, the index of selectivity relative to healthy tissues exceeds that for the reference drugs Doxorubicin and Sorafenib. The biostability of the leading compounds in whole mice blood is sufficiently high for their future quantification in biological matrices.
A few structurally related phenols, dehydrozingerone (DZ), bromopentenone (BP), eugenol (EG) and isoeugenol (IEG), derived from plant products show antioxidant properties by inhibiting lipid peroxidation in membrane models. The phenoxyl radicals produced by the scavenging of free radicals during the inhibition of lipid peroxidation, were also generated by specific one-electron oxidants using pulse radiolysis. The radical lifetimes (second order rate constants for radical-radical reactions), reactivities with hydroxyl and model peroxyl radicals and the one-electron reduction potentials with respect to the standard couples were quantified. These results along with their lipophilicity data were correlated with their antioxidant activity (IC50 values).
Botrytis cinerea is a ubiquitous fungus that affects hundreds of plants, resulting in economic losses to the horticulture and fruit industry. The search for new antifungal agents is a matter of current interest. Thus, in this work a series of geranylated phenols in which the side alkyl chain has been hydrated have been synthesized, and their activity against B. cinerea has been evaluated. The coupling of phenol and geraniol has been accomplished under microwave irradiation obtaining the highest reaction yields in the shortest reaction times. Hydration of the side chain was carried out in dioxane with p-toluenesulfonic acid polymer-bound as the catalyst. All synthesized compounds were tested against B. cinerea using the growth inhibition assay and EC50 values were determined. The results show that activity depends on the number and nature of functional groups in the phenol ring and hydration degree of the geranyl chain. The most active compound is 1,4-dihydroquinone with one hydroxyl group attached at the end of the alkyl chain. Results from a molecular docking study suggest that hydroxyl groups in the phenol ring and alkyl chain are important in the binding of compounds to the active site, and that the experimental antifungal activity correlates with the number of H-bond that can be formed in the binding site.
Beer is a fermented beverage with beneficial phenolic compounds and is widely consumed worldwide. The current study aimed to describe the content of three families of phenolic compounds with relevant biological activities: prenylated flavonoids (from hops), simple phenolic alcohols (from fermentation) and alkylresorcinols (from cereals) in a large sample of beers (n = 45). The prenylated flavonoids analyzed were xanthohumol, isoxanthohumol, 6- and 8-prenylnaringenin. The total prenylated flavonoids present in beer ranged from 0.0 to 9.5 mg/L. The simple phenolic alcohols analyzed were tyrosol and hydroxytyrosol, ranging from 0.2 to 44.4 and 0.0 to 0.1 mg/L, respectively. Our study describes, for the first time, the presence of low amounts of alkylresorcinols in beer, in concentrations ranging from 0.02 to 11.0 µg/L. The results in non-alcoholic beer and the differences observed in the phenolic composition among different beer types and styles highlight the importance of the starting materials and the brewing process (especially fermentation) on the final phenolic composition of beer. In conclusion, beer represents a source of phenolic compounds in the diet that could act synergistically, triggering beneficial health effects in the context of its moderate consumption.
An acceleration of free radical formation within human system exacerbates the incidence of several life-threatening diseases. The systemic antioxidants often fall short for neutralizing the free radicals thereby demanding external antioxidant supplementation. Therein arises the need for development of new antioxidants with improved potency. In order to search for efficient antioxidant molecules, the present work deals with quantitative structure-activity relationship (QSAR) studies of a series of antioxidants belonging to the class of phenolic derivatives bearing NO donor groups. In this study, several QSAR models with appreciable statistical significance have been reported. Models were built using various chemometric tools and validated both internally and externally. These models chiefly infer that presence of substituted aromatic carbons, long chain branched substituents, an oxadiazole-N-oxide ring with an electronegative atom containing group substituted at the 5 position and high degree of methyl substitutions of the parent moiety are conducive to the antioxidant activity profile of these molecules. The novelty of this work is not only that the structural attributes of NO donor phenolic compounds required for potent antioxidant activity have been explored in this study, but new compounds with possible antioxidant activity have also been designed and their antioxidant activity has been predicted in silico.
A series of benzotriazole, cyclic amides and pyrimidine derivatives, containing 2,6-di-tert-butyl-phenol fragments, were synthesized. The redox properties of obtained compounds were studied using the cyclic voltammetry on a platinum electrode in acetonitrile. The oxidation potentials of all substances were comparable to those of BHT. The obtained compounds were tested for their antibacterial activity, and N-(2-(3,5-di-tert-butyl-4-hydroxyphenyl)-2-oxoethyl)isatin (32 μg/mL) exerted good activity against Staphylococcus aureus.
Volatile phenols have been implicated as contributors to off-odors associated with taints from bushfire smoke and microbial spoilage. Various methods for the amelioration of off-odors have been evaluated, but to date, they have not included cyclodextrin (CD) polymers. In the current study, two CD polymers were prepared from β- and γ-CD, using hexamethylene diisocyanate (HDI) as a crosslinking agent. Adsorption tests were performed with four volatile phenols (guaiacol, 4-methylguaiacol, 4-ethylguaiacol and 4-ethylphenol) at concentrations up to 1 mg/L. The removal of volatile phenols by CD polymers achieved equilibrium almost instantly, with isotherm tests suggesting an adsorption capacity of 20.7 µg of volatile phenol per gram of polymer. Langmuir and Freundlich models were subsequently used to fit the data. In batch adsorption tests, the CD polymers achieved 45 to 77% removal of volatile phenols. Polymer reusability was also evaluated and was found to be excellent. A comparison between volatile phenol adsorption by CDs vs. CD polymers, determined using a novel four-phase headspace solid-phase microextraction (HS-SPME) method for gas chromatography-mass spectrometry (GC-MS), suggests CD polymers offer several advantages for use by the wine industry.
Phenols confer bioactivity to a plethora of organic compounds. Protecting the phenolic functionality with photoremovable protecting groups (PPGs) sensitive to two-photon excitation (2PE) can block the bioactivity and provide controlled release of these compounds in a spatially and temporally restricted manner by photoactivation with IR light. To develop an efficient 2PE-sensitive PPG for releasing phenols, the (8-cyano-7-hydroxyquinolin-2-yl)methyl (CyHQ) chromophore was functionalized at the C4 position with methyl, morpholine, methoxy, para-tolyl, and 3,4,5-trimethoxyphenyl groups to provide 4-methyl-CyHQ (Me-CyHQ), 4-morpholino-CyHQ (Mor-CyHQ), 4-methoxy-CyHQ (MeO-CyHQ), 4-(p-tolyl)-CyHQ (pTol-CyHQ), and 4-(3,4,5-trimethoxyphenyl)-CyHQ (TMP-CyHQ) PPGs. The probes possess attributes useful for biological use, including high quantum yield (Φu), hydrolytic stability, and good aqueous solubility in physiological conditions. The MeO-CyHQ PPG enhanced the two-photon uncaging action cross section (δu) of dopamine 3.5-fold (0.85 GM) compared to CyHQ (0.24 GM) at 740 nm and 1.49 GM at 720 nm. MeO-CyHQ was used to mediate photoactivation via 2PE of serotonin, rotigotine, N-vanillyl-nonanoylamide (VNA) (a capsaicin analogue), and eugenol. The constructs except rotigotine showed excellent efficiency in 2PE with δu ranging from 0.75 to 1.01 GM at 740 nm and from 1.31 to 1.36 GM at 720 nm high yielding release of the payloads. These probes also performed well by using conventional single photon excitation (1PE). The spatially and temporally controlled release of dopamine from CyHQ-DA and MeO-CyHQ-DA and serotonin (5-HT) from MeO-CyHQ-5HT was quantified in cell culture by using genetically encoded sensors for dopamine and serotonin, respectively. Calcium imaging was employed to quantify the release of VNA and eugenol (EG) from MeO-CyHQ-VNA and MeO-CyHQ-EG, respectively. These tools will enable experiments to understand the intricate mechanisms involved in neurological signaling and the roles played by neurotransmitters, such as dopamine and serotonin, in the activation of their respective receptors.
Senescent cells display an increase in the secretion of growth factors, inflammatory cytokines and proteolytic enzymes, termed the "senescence-associated-secretory-phenotype" (SASP), playing a major role in many age-related diseases. The phenolic compounds present in extra-virgin olive oil are inhibitors of oxidative damage and have been reported to play a protective role in inflammation-related diseases. Particularly, hydroxytyrosol and oleuropein are the most abundant and more extensively studied. Pre-senescent human lung (MRC5) and neonatal human dermal (NHDF) fibroblasts were used as cellular model to evaluate the effect of chronic (4-6 weeks) treatment with 1 μM hydroxytyrosol (HT) or 10 μM oleuropein aglycone (OLE) on senescence/inflammation markers. Both phenols were effective in reducing β-galactosidase-positive cell number and p16 protein expression. In addition, senescence/inflammation markers such as IL-6 and metalloprotease secretion, and Ciclooxigenase type 2 (COX-2) and α-smooth-actin levels were reduced by phenol treatments. In NHDF, COX-2 expression, Nuclear Factor κ-light-chain-enhancer of activated B cells (NFκB) protein level and nuclear localization were augmented with culture senescence and decreased by OLE and HT treatment. Furthermore, the inflammatory effect of Tumor Necrosis Factor α (TNFα) exposure was almost completely abolished in OLE- and HT-pre-treated NHDF. Thus, the modulation of the senescence-associated inflammatory phenotype might be an important mechanism underlying the beneficial effects of olive oil phenols.
To assess the in vitro activity of five naturally occurring phenolic compounds (ferulic acid, apocynin, magnolol, honokiol, and thymol) on mycelial growth and type B trichothecene mycotoxin accumulation by Fusarium graminearum, three complementary approaches were adopted. First, a high-throughput photometric continuous reading array allowed a parallel quantification of F. graminearum hyphal growth and reporter TRI5 gene expression directly on solid medium. Second, RT-qPCR confirmed the regulation of TRI5 expression by the tested compounds. Third, liquid chromatography-tandem mass spectrometry analysis allowed quantification of deoxynivalenol (DON) and its acetylated forms released upon treatment with the phenolic compounds. Altogether, the results confirmed the activity of thymol and an equimolar mixture of thymol-magnolol at 0.5 mM, respectively, in inhibiting DON production without affecting vegetative growth. The medium pH buffering capacity after 72-96 h of incubation is proposed as a further element to highlight compounds displaying trichothecene inhibitory capacity with no significant fungicidal effect.
Wine is probably the oldest and still most consumed alcoholic beverage in the world. Nevertheless, it contains several biomolecules with beneficial health effects. Phenols are among them and, in this article, we identified and quantified by HPLC catechin, gallic acid, hydroxytyrosol, quercetin, trans-resveratrol, and syringic acid in Primitivo and Negroamaro red wines from Salento, in Southeast Italy. The concentrations of the analyzed antioxidant molecules were quite high in all varieties. Gallic acid and catechin were the most abundant, but significant concentrations of quercetin, hydroxytyrosol, syringic acid, and trans-resveratrol were also found. Multivariate statistical analysis was also employed to discriminate between Negroamaro and Primitivo wines, suggesting the variables influencing their separation.
Seventeen compounds, quercetin-3-O-α-l-rhamnoside (1), kaempferol-3-O-α-L-rhamnoside (2), apigenin-7-O-β-D-glucuronide (3), apigenin 7-O-β-D-glucuronide methyl ester (4), apigenin 7-O-β-D-glucuronide ethyl ester (5), chrysoeriol (6), apigenin (7), kaempferol (8), luteolin (9), quercetin (10), methyl 3,4-dihydroxybenzoate (11), p-coumaric acid (12), 4-hydroxybenzoic acid (13), hydroquinone (14), protocathehuic acid (15), gallic acid (16), and indole-3-carboxylic acid (17), were isolated from the ethanol extract of Taiwanese Cardiospermum halicabum. All chemical structures were determined by physical and extensive spectroscopic analyses such as (1) H Nuclear Magnetic Resonance spectroscopy (NMR), (13)C NMR, (1)H-(1)H Correlation spectroscopy ((1)H-(1)H COSY), Heteronuclear Multiple Quantum Coherence spectroscopy (HMQC), Heteronuclear Multiple-bond Correlation spectroscopy (HMBC), and Nuclear Overhauser Effect spectroscopy (NOESY), as well as comparison with literature values. Furthermore, the High-Performance Liquid Chromatography- Photodiode Array Detector (HPLC-DAD) fingerprint profile was established for the determination of major constituents in the EtOAc extract and retention times of the isolated compounds. All isolated compounds were also evaluated for antiinflammatory and antioxidant activities.
Photoinduced electron transfer (PET), which causes pH-dependent quenching of fluorescent dyes, is more effectively introduced by phenolic groups than by amino groups which have been much more commonly used so far. That is demonstrated by fluorescence measurements involving several classes of fluorophores. Electrochemical measurements show that PET in several amino-modified dyes is thermodynamically favorable, even though it was not experimentally found, underlining the importance of kinetic aspects to the process. Consequently, the attachment of phenolic groups allows for fast and simple preparation of a wide selection of fluorescent pH-probes with tailor-made spectral properties, sensitive ranges, and individual advantages, so that a large number of applications can be realized. Fluorophores carrying phenolic groups may also be used for sensing analytes other than pH or molecular switching and signaling.
Plant-derived phenols are a major input to the terrestrial carbon cycle that might be expected to contribute substantially to dissolved organic carbon (DOC) losses from soils. This study investigated changes in DOC and phenols in leachates from soil treated with individual plant litter types under seasonal temperature change.
Monobenzone is a 4-substituted phenol that can induce vitiligo and antimelanoma immunity. We investigated the influence of the chemical structure on the biological activity of a series of structurally related 4-substituted phenols. All phenols inhibited cellular melanin synthesis, and eight of ten phenols inhibited tyrosinase activity, using the MBTH assay. These phenols also induced glutathione (GSH) depletion, indicative of quinone formation and protein thiol binding, which can increase the immunogenicity of melanosomal proteins. Specific T-cell activation was found upon stimulation with phenol-exposed pigmented cells, which also reacted with unexposed cells. In contrast, 4-tertbutylphenol induced immune activation was not restricted to pigment cells, analogous to contact sensitization. We conclude that 4-substituted phenols can induce specific T-cell responses against melanocytes and melanoma cells, also acting at distant, unexposed body sites, and may confer a risk of chemical vitiligo. Conversely, these phenols may be applicable to induce specific antimelanoma immunity.
Welcome to the FDI Lab - SciCrunch.org Resources search. From here you can search through a compilation of resources used by FDI Lab - SciCrunch.org and see how data is organized within our community.
You are currently on the Community Resources tab looking through categories and sources that FDI Lab - SciCrunch.org has compiled. You can navigate through those categories from here or change to a different tab to execute your search through. Each tab gives a different perspective on data.
If you have an account on FDI Lab - SciCrunch.org then you can log in from here to get additional features in FDI Lab - SciCrunch.org such as Collections, Saved Searches, and managing Resources.
Here is the search term that is being executed, you can type in anything you want to search for. Some tips to help searching:
You can save any searches you perform for quick access to later from here.
We recognized your search term and included synonyms and inferred terms along side your term to help get the data you are looking for.
If you are logged into FDI Lab - SciCrunch.org you can add data records to your collections to create custom spreadsheets across multiple sources of data.
Here are the facets that you can filter your papers by.
From here we'll present any options for the literature, such as exporting your current results.
If you have any further questions please check out our FAQs Page to ask questions and see our tutorials. Click this button to view this tutorial again.
Year:
Count: