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Se Pu = Chinese Journal of... Feb 2024Phenols such as bisphenols, parabens, and triclosan are common environmental endocrine disruptors. Previous epidemiological studies have suggested that phenols may...
Phenols such as bisphenols, parabens, and triclosan are common environmental endocrine disruptors. Previous epidemiological studies have suggested that phenols may affect semen quality, but the results were inconsistent. In addition, most existing studies have been limited to the effects of a single chemical compound, ignoring the health effects of mixed exposure to multiple chemicals. Thus, we aimed to explore the associations between individual and mixed exposure to phenols and various semen quality parameters. In this study, a rapid and sensitive method was used to determine 18 phenolic compounds in urine samples of 799 volunteers who donated sperm samples to the Shanghai Human Sperm Bank. A spot urine sample was collected from each subject on the day of their clinic visit and stored at -20 ℃ until testing. Urine samples (200 μL) were extracted and added with 20 μL of an internal standard and 50 μL of β-glucuronidase solution. The mixtures were then incubated for 12 h at 37 ℃. After hydrolysis, the samples were extracted twice using ethyl acetate (500 μL). The concentrations of the 18 phenolic compounds were measured using high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS). Semen quality parameters were analyzed using a computer-aided semen analyzer. Multiple linear regressions were used to detect the associations between individual phenol exposure and semen quality parameters. In addition, weighted quantile sum (WQS) models were used to explore the associations between mixed-phenol exposure and semen quality parameters. After adjusting for potential covariates, the results of multiple linear regressions showed that exposure to ethyl paraben (EtP) was significantly negatively associated with sperm concentration and total sperm count (P<0.05). In addition, exposure to mixed phenols was significantly associated with decreased sperm concentration; methyl paraben (MeP) and EtP were identified as the main contributors to this decrease. Thus, phenol exposure may be associated with decreased semen quality in young males, particularly with respect to sperm concentration and total sperm count.
Topics: Humans; Male; Semen Analysis; Phenol; Semen; Tandem Mass Spectrometry; China; Phenols; Parabens
PubMed: 38374601
DOI: 10.3724/SP.J.1123.2023.09009 -
MicrobiologyOpen Oct 2022Five yeast fungi strains (i.e., two Cryptococcus albidus, one Candida guillermondii, and two Candida tropicalis) were isolated from sugarcane and tested for their use of...
Five yeast fungi strains (i.e., two Cryptococcus albidus, one Candida guillermondii, and two Candida tropicalis) were isolated from sugarcane and tested for their use of lignin as sole carbon source and their potential to grow in the presence of phenol and phenol derivatives (i.e., pentachlorophenol and p-nitrophenol). The full set of isolated yeasts showed ligninolytic activity, achieving at least 36% lignin degradation after 25 days. The C. albidus JS-B1 strain had the highest ligninolytic activity, achieving 27% lignin degradation within 4 days. This increased activity was associated with the production of ligninolytic laccase enzymes. All the tested yeast fungi strains showed growth in the presence of high concentrations of phenolic compounds (i.e., 900 mg/L phenol, 200 mg/L p-nitrophenol, 50 mg/L pentachlorophenol) and showed significant potential for lignin and lignin by-product degradation. Each of these five strains has the potential to be used in biological treatment processes for contaminated effluents from paper pulping and bleaching or phenol and phenol-derivative biodegradation processes for other industrial wastewater effluents.
Topics: Lignin; Pentachlorophenol; Nitrophenols; Yeasts; Phenol; Biodegradation, Environmental; Phenols
PubMed: 36314751
DOI: 10.1002/mbo3.1326 -
The Journal of Physical Chemistry. B Oct 2021Therapeutic preparations of insulin often contain phenolic molecules, which can impact both pharmacokinetics and shelf life. Thus, understanding the interactions of...
Therapeutic preparations of insulin often contain phenolic molecules, which can impact both pharmacokinetics and shelf life. Thus, understanding the interactions of insulin and phenolic molecules can aid in designing improved therapeutics. In this study, we use molecular dynamics to investigate phenol release from the insulin hexamer. Leveraging recent advances in methods for analyzing molecular dynamics data, we expand on existing simulation studies to identify and quantitatively characterize six phenol binding/unbinding pathways for wild-type and A10 Ile → Val and B13 Glu → Gln mutant insulins. A number of these pathways involve large-scale opening of the primary escape channel, suggesting that the hexamer is much more dynamic than previously appreciated. We show that phenol unbinding is a multipathway process, with no single pathway representing more than 50% of the reactive current and all pathways representing at least 10%. We use the mutant simulations to show how the contributions of specific pathways can be rationally manipulated. Predicting the net effects of mutations is more challenging because the kinetics depend on all of the pathways, demanding quantitatively accurate simulations and experiments.
Topics: Insulin; Kinetics; Phenol; Phenols
PubMed: 34648712
DOI: 10.1021/acs.jpcb.1c06544 -
Microbiology Spectrum Dec 2023Aromatic compounds are globally abundant organic molecules with a multitude of natural and anthropogenic sources, underpinning the relevance of their biodegradation....
Aromatic compounds are globally abundant organic molecules with a multitude of natural and anthropogenic sources, underpinning the relevance of their biodegradation. EbN1 is a well-studied environmental betaproteobacterium specialized on the anaerobic degradation of aromatic compounds. The here studied responsiveness toward phenol in conjunction with the apparent high ligand selectivity (non-promiscuity) of its PheR sensor and those of the related -cresol (PcrS) and -ethylphenol (EtpR) sensors are in accord with the substrate-specificity and biochemical distinctiveness of the associated degradation pathways. Furthermore, the present findings advance our general understanding of the substrate-specific regulation of the strain's remarkable degradation network and of the concentration thresholds below which phenolic compounds become essentially undetectable and as a consequence should escape substantial biodegradation. Furthermore, the findings may inspire biomimetic sensor designs for detecting and quantifying phenolic contaminants in wastewater or environments.
Topics: Phenol; Phenols; Rhodocyclaceae; Biodegradation, Environmental; Anaerobiosis
PubMed: 37823660
DOI: 10.1128/spectrum.02100-23 -
ACS Chemical Biology Sep 2021Membrane protein structures provide a fundamental understanding of their molecular actions and are of importance for drug development. Detergents are widely used to...
Membrane protein structures provide a fundamental understanding of their molecular actions and are of importance for drug development. Detergents are widely used to solubilize, stabilize, and crystallize membrane proteins, but membrane proteins solubilized in conventional detergents are prone to denaturation and aggregation. Thus, developing novel detergents with enhanced efficacy for protein stabilization remains important. We report herein the design and synthesis of a class of phenol-derived maltoside detergents. Using two different linkers, we prepared two sets of new detergents, designated maltose-bis(hydroxymethyl)phenol (MBPs) and maltose-tris(hydroxymethyl)phenol (MTPs). The evaluation of these detergents with three transporters and two G-protein coupled receptors allowed us to identify a couple of new detergents (MBP-C9 and MTP-C12) that consistently conferred enhanced stability to all tested proteins compared to a gold standard detergent (DDM). Furthermore, the data analysis based on the detergent structures provides key detergent features responsible for membrane protein stabilization that together will facilitate the future design of novel detergents.
Topics: Detergents; Glycolipids; Hydrophobic and Hydrophilic Interactions; Membrane Transport Proteins; Phenol; Protein Conformation; Protein Denaturation; Protein Stability; Receptors, G-Protein-Coupled; Structure-Activity Relationship; Thermodynamics
PubMed: 34445864
DOI: 10.1021/acschembio.1c00578 -
International Journal of Hygiene and... Mar 2023Early life environmental exposures may affect bone mass accrual in childhood, but only one study has assessed the role of environmental phenols on child bone health.
BACKGROUND
Early life environmental exposures may affect bone mass accrual in childhood, but only one study has assessed the role of environmental phenols on child bone health.
METHODS
We used data from 223 mother-child dyads enrolled in the Health Outcomes and Measures of the Environment (HOME) Study (Cincinnati, OH; 2003-2006). We quantified benzophenone-3, bisphenol A (BPA), 2,5-dichlorophenol, and triclosan in maternal urine collected at 16- and 26-weeks gestation and calculated the average of creatinine-adjusted concentrations. We performed dual x-ray absorptiometry at age 12 years and calculated Z-scores for whole body (less head), total hip, femoral neck, and 1/3rd distal radius bone mineral content (BMC) and areal bone mineral density (aBMD) as well as ultra-distal radius aBMD and spine BMC and bone mineral apparent density (BMAD). We estimated covariate-adjusted associations per doubling of maternal urinary environmental phenol concentrations in linear regression models. We also examined effect measure modification by child's sex and estimated associations of the environmental phenol mixture with BMC and aBMD using quantile g-computation.
RESULTS
We observed generally null associations for all analytes and bone measures. Yet, in adjusted models, higher urinary 2,5-dichlorophenol concentrations were associated with higher 1/3rd distal radius BMC (β: 0.09; 95% CI: 0.02, 0.17) and aBMD (β: 0.09; 95% CI: 0.02, 0.17) Z-scores in the overall sample. In sex-stratified analyses, the magnitude of the BMC association was positive for females (β: 0.16; 95% CI: 0.06, 0.26) and null for males (β: 0.02; 95% CI: 0.08, 0.13). The environmental phenol mixture was associated with greater 1/3rd distal radius BMC and aBMD Z-scores in both sexes, which was mostly driven by benzophenone-3 in males and 2,5-dichlorophenol in females.
CONCLUSION
In this prospective cohort study, we observed generally null associations for environmental phenols with BMC and aBMD at age 12 years. While there was a positive association of 2,5-dichlorophenol concentrations during fetal development with distal radius BMC and aBMD at age 12 years, future studies utilizing methods capable of differentiating cortical and trabecular bone are needed to elucidate potential mechanisms and implications for bone strength and microarchitecture.
Topics: Male; Female; Humans; Child; Bone Density; Prospective Studies; Phenol
PubMed: 36525700
DOI: 10.1016/j.ijheh.2022.114104 -
International Journal of Molecular... May 2023A number of novel di- and triorganotin(IV) complexes - (PhSnL, PhSnL, EtSnL, PhSnL, PhSnL) with mono- or dianionic forms of thio-Schiff bases containing antioxidant...
A number of novel di- and triorganotin(IV) complexes - (PhSnL, PhSnL, EtSnL, PhSnL, PhSnL) with mono- or dianionic forms of thio-Schiff bases containing antioxidant sterically hindered phenol or catechol fragments were synthesized. Compounds - were characterized by H, C NMR, IR spectroscopy, and elemental analysis. The molecular structures of complexes and in the crystal state were established by single-crystal X-ray analysis. The antioxidant activity of new complexes as radical scavengers was estimated in DPPH and ABTS assays. It was found that compounds and with free phenol or catechol fragments are more active in these tests than complexes - with tridentate O,N,S-coordinated ligands. The effect of compounds - on the promoted oxidative damage of the DNA by 2,2'-azobis(2-amidinopropane) dihydrochloride and in the process of rat liver (Wistar) homogenate lipid peroxidation in vitro was determined. Complexes and were characterized by more pronounced antioxidant activity in the reaction of lipid peroxidation in vitro than compounds -. The antiproliferative activity of compounds - was investigated against MCF-7, HTC-116, and A-549 cell lines by an MTT test. The values of IC are significantly affected by the presence of free antioxidant fragments and the coordination site for binding.
Topics: Rats; Animals; Antioxidants; Phenol; Schiff Bases; Rats, Wistar; Organotin Compounds; Phenols; Catechols; Coordination Complexes; Ligands
PubMed: 37176027
DOI: 10.3390/ijms24098319 -
Molecules (Basel, Switzerland) Aug 2022Phenol is an important chemical material that is widely used in industry. Currently, phenol is dominantly produced by the well-known three-step cumene process, which... (Review)
Review
Phenol is an important chemical material that is widely used in industry. Currently, phenol is dominantly produced by the well-known three-step cumene process, which suffers from severe drawbacks. Therefore, developing a green, sustainable, and economical strategy for the production of phenol directly from benzene is urgently needed. In recent years, the photocatalytic hydroxylation of benzene to phenol, which is economically feasible and could be performed under mild conditions, has attracted more attention, and development of highly efficient photocatalyst would be a key issue in this field. In this review, we systematically introduce the recent achievements of photocatalytic hydroxylation of benzene to phenol from 2015 to mid-2022, and various heterogeneous photocatalysts are comprehensively reviewed, including semiconductors, polyoxometalates (POMs), graphitic carbon nitride (g-CN), metal-organic frameworks (MOFs), carbon materials, and some other types of photocatalysts. Much effort is focused on the physical and chemical approaches for modification of these photocatalysts. The challenges and future promising directions for further enhancing the catalytic performances in photocatalytic hydroxylation of benzene are discussed in the end.
Topics: Benzene; Catalysis; Hydroxylation; Phenol; Phenols
PubMed: 36080224
DOI: 10.3390/molecules27175457 -
Molecules (Basel, Switzerland) Mar 2022Plant polyphenols, such as the African potato ()-derived bis-catechol rooperol, can display promising anticancer activity yet suffer from rapid metabolism. Embarking...
Plant polyphenols, such as the African potato ()-derived bis-catechol rooperol, can display promising anticancer activity yet suffer from rapid metabolism. Embarking upon a program to systematically examine potentially more metabolically stable replacements for the catechol rings in rooperol, we report here a general, scalable synthesis of rooperol and analogues that builds on our previous synthetic approach incorporating a key Pd-catalyzed decarboxylative coupling strategy. Using this approach, we have prepared and evaluated the cancer cell cytotoxicity of rooperol and a series of analogues. While none of the analogues examined here were superior to rooperol in preventing the growth of cancer cells, analogues containing phenol or methylenedioxyphenyl replacements for one or both catechol rings were nearly as effective as rooperol.
Topics: Catechols; Neoplasms; Phenol; Phenols; Polyphenols
PubMed: 35335155
DOI: 10.3390/molecules27061792 -
European Journal of Nutrition Feb 2023(Poly)phenols are bioactive compounds widely distributed in plant-based foods. Currently, limited data exist on the intake distribution of (poly)phenols across meals....
PURPOSE
(Poly)phenols are bioactive compounds widely distributed in plant-based foods. Currently, limited data exist on the intake distribution of (poly)phenols across meals. This study aimed to estimate dietary intakes of all individual (poly)phenols and total intake per class and subclass by meal event, and to identify their main food sources in the subcohort MAX from the Diet, Cancer and Health-Next Generations cohort (DCH-NG).
METHODS
Dietary data were collected using three web-based 24-h dietary recalls over 1 year. In total, 676 participants completed at least one recall. The dietary data were linked to Phenol-Explorer database using standardized procedures and an in-house software. We categorized foods/drinks into five options of meal events selected by the participant: 'Breakfast', 'Lunch', 'Evening', 'Snack', and 'Drink'.
RESULTS
Adjusted total (poly)phenols mean intake by meal was the highest in the drink event (563 mg/day in men and 423 mg/day in women) and the lowest in the evening event (146 mg/day in men and 137 mg/day in women). The main overall (poly)phenol class contributor was phenolic acids (55.7-79.0%), except for evening and snack events where it was flavonoids (45.5-60%). The most consumed (poly)phenol subclasses were hydroxycinnamic acids and proanthocyanidins. Nonalcoholic beverages (coffee accounted for 66.4%), cocoa products, and cereals were the main food sources of total (poly)phenols.
CONCLUSION
This study provides data on the variability in the intake of classes and subclasses of (poly)phenols and their main food sources by meal event according to lifestyle data, age, and gender in a Danish population.
Topics: Male; Humans; Female; Phenol; Polyphenols; Phenols; Diet; Neoplasms
PubMed: 35994085
DOI: 10.1007/s00394-022-02977-x