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The American Journal of Clinical... Jun 2023Evidence suggests that the intake of blueberry (poly)phenols is associated with improvements in vascular function and cognitive performance. Whether these cognitive... (Randomized Controlled Trial)
Randomized Controlled Trial
BACKGROUND
Evidence suggests that the intake of blueberry (poly)phenols is associated with improvements in vascular function and cognitive performance. Whether these cognitive effects are linked to increases in cerebral and vascular blood flow or changes in the gut microbiota is currently unknown.
METHODS
A double-blind, parallel randomized controlled trial was conducted in 61 healthy older individuals aged 65-80 y. Participants received either 26 g of freeze-dried wild blueberry (WBB) powder (302 mg anthocyanins) or a matched placebo (0 mg anthocyanins). Endothelial function measured by flow-mediated dilation (FMD), cognitive function, arterial stiffness, blood pressure (BP), cerebral blood flow (CBF), gut microbiome, and blood parameters were measured at baseline and 12 wk following daily consumption. Plasma and urinary (poly)phenol metabolites were analyzed using microelution solid-phase extraction coupled with liquid chromatography-mass spectrometry.
RESULTS
A significant increase in FMD and reduction in 24 h ambulatory systolic BP were found in the WBB group compared with the placebo group (0.86%; 95% CI: 0.56, 1.17, P < 0.001; -3.59 mmHg; 95% CI: -6.95, -0.23, P = 0.037; respectively). Enhanced immediate recall on the auditory verbal learning task, alongside better accuracy on a task-switch task was also found following WBB treatment compared with placebo (P < 0.05). Total 24 h urinary (poly)phenol excretion increased significantly in the WBB group compared with placebo. No changes in the CBF or gut microbiota composition were found.
CONCLUSIONS
Daily intake of WBB powder, equivalent to 178 g fresh weight, improves vascular and cognitive function and decreases 24 h ambulatory systolic BP in healthy older individuals. This suggests that WBB (poly)phenols may reduce future CVD risk in an older population and may improve episodic memory processes and executive functioning in older adults at risk for cognitive decline. Clinical Trial Registration number in clinicaltrials.gov: NCT04084457.
Topics: Humans; Aged; Anthocyanins; Blueberry Plants; Phenols; Phenol; Powders; Fruit; Cognition; Memory, Short-Term; Double-Blind Method
PubMed: 36972800
DOI: 10.1016/j.ajcnut.2023.03.017 -
Nutrients Aug 2022Plant-derived (poly)phenolic compounds have been undoubtedly shown to promote endocrine homeostasis through the improvement of diverse metabolic outcomes. Amongst... (Review)
Review
Plant-derived (poly)phenolic compounds have been undoubtedly shown to promote endocrine homeostasis through the improvement of diverse metabolic outcomes. Amongst diverse potential mechanisms, the prebiotic modulatory effects exerted by these compounds on the gut microbiota have supported their nutraceutical application in both experimental and clinical approaches. However, the comprehension of the microbiota modulatory patterns observed upon (poly)phenol-based dietary interventions is still in its infancy, which makes the standardization of the metabolic outcomes in response to a given (poly)phenol a herculean task. Thus, this narrative review sought to gather up-to-date information on the relationship among (poly)phenols intake, their modulatory effect on the gut microbiota diversity, and consequent metabolic outcomes as a supportive tool for the future design of experimental approaches and even clinical trials.
Topics: Gastrointestinal Microbiome; Microbiota; Phenol; Phenols; Prebiotics
PubMed: 36079768
DOI: 10.3390/nu14173510 -
Environmental Science and Pollution... May 2023Endocrine-disrupting chemicals (EDCs) may impact sleep during the menopausal transition by altering sex hormones. However, these studies are scarce among Latin American...
Associations between exposure to phthalates, phenols, and parabens with objective and subjective measures of sleep health among Mexican women in midlife: a cross-sectional and retrospective analysis.
Endocrine-disrupting chemicals (EDCs) may impact sleep during the menopausal transition by altering sex hormones. However, these studies are scarce among Latin American women. This investigation utilized cross-sectional and retrospective data from midlife women enrolled in the Early Life Exposure in Mexico to Environmental Toxicants (ELEMENT) study to examine associations between exposure to EDCs (phthalates, phenols, and parabens) and sleep health measures. For cross-sectional analyses, single spot urine samples were collected between 2017-2019 from a pilot sample of women (N = 91) of midlife age to estimate the urinary concentration of individual phthalates, phenols, and parabens and to calculate the summary concentration of phthalate mixtures. Seven-day nightly sleep duration, midpoint, and fragmentation were obtained from wrist-actigraphy devices and estimated from the actigraphy data using a pruned dynamic programming algorithm. Self-reported poor sleep quality was assessed by one item from the Pittsburgh Sleep Quality Index (PSQI). We examined associations between urinary summary phthalate mixtures, phthalate metabolites, phenol, and paraben analytes with each sleep measure using linear or logistic (to compute odds of poor sleep quality only) regression models adjusted for specific gravity, age, and socioeconomic status. We ran similar regression models for retrospective analyses (N = 74), except that urine exposure biomarker data were collected in 2008 when women were 24-50 years old. At the 2017-2019 midlife visit, 38% reported poor sleep quality. Cross-sectionally, EDCs were associated with longer sleep duration, earlier sleep timing, and more fragmented sleep. For example, every 1-unit IQR increase in the phenol triclosan was associated with a 26.3 min per night (95% CI: 10.5, 42.2; P < 0.05) longer sleep duration and marginally associated with 0.2 decimal hours (95% CI: -0.4, 0.0; P < 0.10) earlier sleep midpoint; while every 1-unit IQR increase in the phthalate metabolite MEHP was associated with 1.1% higher sleep fragmentation (95% CI: 0.1, 2.1; P < 0.05). Retrospective study results generally mirrored cross-sectional results such that EDCs were linked to longer sleep duration, earlier sleep timing, and more fragmented sleep. EDCs were not significantly associated with odds of self-reported poor sleep quality. Results from cross-sectional and retrospective analyses revealed that higher exposure to EDCs was predictive of longer sleep duration, earlier sleep timing, and more fragmented sleep among midlife women.
Topics: Humans; Female; Young Adult; Adult; Middle Aged; Retrospective Studies; Parabens; Cross-Sectional Studies; Phenols; Phenol; Mexico; Phthalic Acids; Endocrine Disruptors; Sleep Initiation and Maintenance Disorders; Sleep; Environmental Pollutants; Environmental Exposure
PubMed: 37086320
DOI: 10.1007/s11356-023-26833-5 -
Reproductive Toxicology (Elmsford, N.Y.) Oct 2022Exposure to phenols is widespread since they are found in many everyday products. Given that phenols are considered endocrine disrupting chemicals with the potential to...
Exposure to phenols is widespread since they are found in many everyday products. Given that phenols are considered endocrine disrupting chemicals with the potential to interfere with hormonal activities, they could have adverse effects on female reproductive health. We analyzed cross-sectional data from the National Health and Nutrition Examination Survey (NHANES), 2003-2006 to examine the association between phenols and endometriosis and uterine leiomyoma (fibroids). Levels of bisphenol A (BPA), benzophenone-3, and triclosan were measured using urine samples, and information on endometriosis and fibroids diagnoses as well as other relevant characteristics were ascertained using self-reported questionnaires. Multivariate logistic regression with odds ratios (ORs) and 95 % confidence intervals (CIs) were used to quantify the association between each phenol and female gynecologic condition. Our study included 700 women, of which 53 women had endometriosis and 107 women had fibroids. We found exposure to BPA to be statistically significantly positively associated with endometriosis (p = 0.05); women in the highest exposure quartile had over the three times the odds of having endometriosis relative to women in the lowest quartile (OR=3.58, 95 % CI 1.00-12.89). None of the phenols considered were significantly associated with fibroids. Overall, exposure to BPA increased the odds of having endometriosis, and there appeared to be a dose-response relationship. This suggests that BPA may play a role in the pathogenesis of endometriosis although the cross-sectional nature of NHANES data is a methodological limitation. Additional research on the impact of endocrine disrupting chemicals, like phenols, on female reproductive health should be conducted.
Topics: Benzhydryl Compounds; Cross-Sectional Studies; Endocrine Disruptors; Endometriosis; Environmental Exposure; Environmental Pollutants; Female; Humans; Leiomyoma; Nutrition Surveys; Phenol; Phenols; Triclosan
PubMed: 35948171
DOI: 10.1016/j.reprotox.2022.08.003 -
Physical Chemistry Chemical Physics :... Nov 2022Halogenated groups are relevant in pharmaceutical applications and potentially useful spectroscopic probes for infrared spectroscopy. In this work, the structural...
Halogenated groups are relevant in pharmaceutical applications and potentially useful spectroscopic probes for infrared spectroscopy. In this work, the structural dynamics and infrared spectroscopy of -fluorophenol (F-PhOH) and phenol (PhOH) is investigated in the gas phase and in water using a combination of experiment and molecular dynamics (MD) simulations. The gas phase and solvent dynamics around F-PhOH and PhOH is characterized from atomistic simulations using empirical energy functions with point charges or multipoles for the electrostatics, Machine Learning (ML) based parametrizations and with full (QM) and mixed Quantum Mechanical/Molecular Mechanics (QM/MM) simulations with a particular focus on the CF- and OH-stretch region. The CF-stretch band is heavily mixed with other modes whereas the OH-stretch in solution displays a characteristic high-frequency peak around 3600 cm most likely associated with the -OH group of PhOH and F-PhOH together with a characteristic progression below 3000 cm due to coupling with water modes which is also reproduced by several of the simulations. Solvent and radial distribution functions indicate that the CF-site is largely hydrophobic except for simulations using point charges which renders them unsuited for correctly describing hydration and dynamics around fluorinated sites. The hydrophobic character of the CF-group is particularly relevant for applications in pharmaceutical chemistry with a focus on local hydration and interaction with the surrounding protein.
Topics: Quantum Theory; Phenols; Spectrophotometry, Infrared; Water; Solvents; Phenol
PubMed: 36268728
DOI: 10.1039/d2cp02857c -
Scientific Reports Nov 2022Boron tribromide-mediated demethylation of rhenium-oxo and gold meso-tris(4-methoxyphenyl)corrole and meso-tris(3,5-dimethoxyphenylcorrole), M[TpOMePC] and...
Boron tribromide-mediated demethylation of rhenium-oxo and gold meso-tris(4-methoxyphenyl)corrole and meso-tris(3,5-dimethoxyphenylcorrole), M[TpOMePC] and M[T(3,5-OMe)PC] (M = ReO, Au), have yielded the corresponding phenol- and resorcinol-appended metallocorroles, M[TpOHPC] and M[T(3,5-OH)PC], in good yields. The latter compounds proved insoluble in dichloromethane and chloroform but soluble in THF. The M[T(3,5-OH)PC] derivatives also proved moderately soluble in 0.05 M aqueous KOH. Unlike oxidation-prone aminophenyl-substituted corroles, the phenol- and resorcinol-appended metallocorroles could be readily handled in air without special precautions. The phenolic metallocorroles could be readily alkylated with 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl iodide ("FtI") to afford the fluorous-tagged metallocorroles M[TpOFtPC] and M[T(3,5-OFt)PC] in > 90% yields. The simplicity of the synthetic protocols promise a wide range of phenolic and fluorous-tagged porphyrin analogues with potential applications to diverse fields such as sensors, catalysis, and photodynamic therapy, among others.
Topics: Phenol; Phenols; Resorcinols; Catalysis
PubMed: 36357501
DOI: 10.1038/s41598-022-23889-0 -
Molecules (Basel, Switzerland) Sep 2022Vitamin E, a collection of lipophilic phenolic compounds based on chroman-6-ol, has a rich and fascinating oxidative chemistry involving a range of intermediate forms,... (Review)
Review
Vitamin E, a collection of lipophilic phenolic compounds based on chroman-6-ol, has a rich and fascinating oxidative chemistry involving a range of intermediate forms, some of which are proposed to be important in its biological functions. In this review, the available electrochemical and spectroscopic data on these oxidized intermediates are summarized, along with a discussion on how their lifetimes and chemical stability are either typical of similar phenolic and chroman-6-ol derived compounds, or atypical and unique to the specific oxidized isomeric form of vitamin E. The overall electrochemical oxidation mechanism for vitamin E can be summarized as involving the loss of two-electrons and one-proton, although the electron transfer and chemical steps can be controlled to progress along different pathways to prolong the lifetimes of discreet intermediates by modifying the experimental conditions (applied electrochemical potential, aqueous or non-aqueous solvent, and pH). Depending on the environment, the electrochemical reactions can involve single electron transfer (SET), proton-coupled electron transfer (PCET), as well as homogeneous disproportionation and comproportionation steps. The intermediate species produced via chemical or electrochemical oxidation include phenolates, phenol cation radicals, phenoxyl neutral radicals, dications, diamagnetic cations (phenoxeniums) and -quinone methides. The cation radicals of all the tocopherols are atypically long-lived compared to the cation radicals of other phenols, due to their relatively weak acidity. The diamagnetic cation derived from α-tocopherol is exceptionally long-lived compared to the diamagnetic cations from the other β-, γ- and δ-isomers of vitamin E and compared with other phenoxenium cations derived from phenolic compounds. In contrast, the lifetime of the phenoxyl radical derived from α-tocopherol, which is considered to be critical in biological reactions, is typical for what is expected for a compound with its structural features. Over longer times via hydrolysis reactions, hydroxy -quinone hemiketals and quinones can be formed from the oxidized intermediates, which can themselves undergo reduction processes to form intermediate anion radicals and dianions. Methods for generating the oxidized intermediates by chemical, photochemical and electrochemical methods are discussed, along with a summary of how the final products vary depending on the method used for oxidation. Since the intermediates mainly only survive in solution, they are most often monitored using UV-vis spectroscopy, FTIR or Raman spectroscopies, and EPR spectroscopy, with the spectroscopic techniques sometimes combined with fast photoinitiated excitation and time-resolved spectroscopy for detection of short-lived species.
Topics: Benzoquinones; Chromans; Electron Spin Resonance Spectroscopy; Oxidation-Reduction; Phenol; Phenols; Protons; Solvents; Tocopherols; Vitamin E; alpha-Tocopherol
PubMed: 36234726
DOI: 10.3390/molecules27196194 -
International Journal of Molecular... Jun 2020The clinically important () and related mycobacterial pathogens use various virulence mechanisms to survive and cause disease in their hosts. Several well-established... (Review)
Review
The clinically important () and related mycobacterial pathogens use various virulence mechanisms to survive and cause disease in their hosts. Several well-established virulence factors include the surface-exposed lipids in the mycobacterial outer membrane, as well as the Esx family proteins and the Pro-Glu (PE)/ Pro-Pro-Glu (PPE) family proteins secreted by type VII secretion systems (T7SS). Five ESX T7SS exist in and three-EsxA secretion system-1 (ESX-1), ESX-3, and ESX-5-have been implicated in virulence, yet only the structures of ESX-3 and ESX-5 have been solved to date. Here, we summarize the current research on three outer membrane lipids-phthiocerol dimycocerosates, phenolic glycolipids, and sulfolipids-as well as the secretion machinery and substrates of three mycobacterial T7SS-ESX-1, ESX-3, and ESX-5. We propose a structural model of the ESX-1 system based on the latest structural findings of the ESX-3 and ESX-5 secretion apparatuses to gain insight into the transport mechanism of ESX-associated virulence factors.
Topics: Animals; Antigens, Bacterial; Bacterial Proteins; Glycolipids; Humans; Lipids; Mycobacterium tuberculosis; Phenol; Surface Properties; THP-1 Cells; Virulence; Virulence Factors
PubMed: 32498243
DOI: 10.3390/ijms21113985 -
International Journal of Molecular... Sep 2021Skin cancer represents any tumor development from the cutaneous structures within the epidermis, dermis or subcutaneous tissue, and is considered to be the most... (Review)
Review
Skin cancer represents any tumor development from the cutaneous structures within the epidermis, dermis or subcutaneous tissue, and is considered to be the most prevalent type of cancer. Compared to other types of cancer, skin cancer is proven to have a positive growth rate of prevalence and mortality. There are available various treatments, including chemotherapy, immunotherapy, radiotherapy and targeted therapy, but because of the multidrug resistance development, a low success has been registered. By this, the importance of studying naturally occurring compounds that are both safe and effective in the chemoprevention of skin cancer is emphasized. This review focuses on melanoma because it is the deadliest form of skin cancer, with a significantly increasing incidence in the last decades. As chemopreventive agents, we present polyphenols and their antioxidant activity, anti-inflammatory effect, their ability to balance the cell cycle and to induce apoptosis and their various other effects on skin melanoma. Besides chemoprevention, studies suggest that polyphenols can have treating abilities in some conditions. The limitations of using polyphenols are also pointed out, which are related to their poor bioavailability and stability, but as the technology is well developed, it is possible to augment the efficacy of polyphenols in the case of melanoma.
Topics: Animals; Anti-Inflammatory Agents; Anticarcinogenic Agents; Antioxidants; Apoptosis; Autophagy; Cell Cycle; Cell Proliferation; Chemoprevention; Humans; Immunosuppressive Agents; Immunotherapy; Melanoma; Mice; Neoplasm Metastasis; Phenol; Phenols; Polyphenols; Skin; Skin Neoplasms; Tea; Ultraviolet Rays; Melanoma, Cutaneous Malignant
PubMed: 34575899
DOI: 10.3390/ijms22189707 -
Techniques in Coloproctology Dec 2023Non-excisional techniques for pilonidal sinus disease (PSD) have gained popularity over the last years. The aim of this study was to review short and long-term outcomes... (Review)
Review
Non-excisional techniques for pilonidal sinus disease (PSD) have gained popularity over the last years. The aim of this study was to review short and long-term outcomes for non-excisional techniques with special focus on the additive effect of treatment of the inner lining of the sinus cavity and the difference between primary and recurrent PSD. A systematic search was conducted in Embase, Medline, Web of Science Core Collection, Cochrane and Google Scholar databases for studies on non-excisional techniques for PSD including pit picking techniques with or without additional laser or phenol treatment, unroofing, endoscopic techniques and thrombin gelatin matrix application. Outcomes were recurrence rates, healing rates, complication rates, wound healing times and time taken to return to daily activities. In total, 31 studies comprising 8100 patients were included. Non-excisional techniques had overall healing rates ranging from 67 to 100%. Recurrence rates for pit picking, unroofing and gelatin matrix application varied from 0 to 16% depending on the follow-up time. Recurrence rates after additional laser, phenol and endoscopic techniques varied from 0 to 29%. Complication rates ranged from 0 to 16%, and the wound healing time was between three and forty-seven days. The return to daily activities varied from one to nine days. Non-excisional techniques are associated with fast recovery and low morbidity but recurrence rates are high. Techniques that attempt to additionally treat the inner lining of the sinus have worse recurrence rates than pit picking alone. Recurrence rates do not differ between primary and recurrent disease.
Topics: Humans; Pilonidal Sinus; Gelatin; Neoplasm Recurrence, Local; Wound Healing; Phenol; Recurrence; Treatment Outcome
PubMed: 37930579
DOI: 10.1007/s10151-023-02870-7