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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 -
F1000Research 2021contains several bioactive molecules such as phenol, flavonoid and phycocyanin pigments. This study unveils total phenol, flavonoid, antioxidant activity,...
contains several bioactive molecules such as phenol, flavonoid and phycocyanin pigments. This study unveils total phenol, flavonoid, antioxidant activity, phycocyanin content and evaluated encapsulation efficiency from intervention on . intervention aims to reduce unpleasant odors from that will increase consumption and increase bioactive compounds. The intervention was carried out by soaking a control sample (SP) in with a ratio of 1:4 (w/v) and it was then dried (DSB) and microencapsulated by freeze drying methods (MSB) using a combination of maltodextrin and gelatin. Total flavonoid and phenolic analysis with curve fitting analysis used a linear regression approach. Antioxidant activity of samples was analysed with the 2,2'-azino-bis-3-3thylbenzthiazoline-6-sulphonic acid (ABTS) method. Data were analysed using ANOVA at significance level (p < 0.05) followed by Tukey test models using SPSS v.22. The result of this study indicated that intervention treatment (DSB) has the potential to increase bioactive compounds such as total phenol, antioxidant activity and phycocyanin, and flavonoid content. Intervention of on (DSB) significantly increases total phenol by 49.5% and phycocyanin by 40.7%. This is due to the phenol and azulene compounds in which have a synergistic effect on phenol and phycocyanin in . Microencapsulation using a maltodexrin and gelatin coating is effective in phycocyanin protection and antioxidant activity with an encapsulation efficiency value of 71.58% and 80.5%. The intervention of on improved the total phenol and phycocyanin content and there is potential for a pharmaceutical product for a functional food and pharmaceutical product.
Topics: Antioxidants; Flavonoids; Gelatin; Ocimum basilicum; Phenol; Phenols; Phycocyanin; Powders; Spirulina
PubMed: 35083034
DOI: 10.12688/f1000research.52394.3 -
Journal of Hazardous Materials Oct 2021In this study, anaerobic batch experiments were conducted to investigate the effect of carbon-based (biochar) and metal-based (nanoscale zero-valent iron, NZVI and zero...
In this study, anaerobic batch experiments were conducted to investigate the effect of carbon-based (biochar) and metal-based (nanoscale zero-valent iron, NZVI and zero valent iron, ZVI) mediators on the AD process treating phenolic wastewater. Fresh apricot shell- and wood-derived biochar (BiocharA, BiocharB) could remove the phenol efficiently (77.1% and 86.2%), suggesting that biodegradation cooperated with adsorption had advantage in phenol removal. BiocharB, NZVI and ZVI enhanced the methane production by 17.6%, 23.7% and 23.2%, respectively. Apart from serving as carrier for microbial growth, BiocharB might promote the direct interspecies electron transfer (DIET) since the Anaerolineaceae/Clostridium sensu stricto, which have potential for DIET, were enriched. NZVI and ZVI added systems mainly enhanced the abundance of Clostridium sensu stricto (24.5%, 37.6%) and Methanosaeta. Interestingly, BiocharA inhibited the methanogenesis completely. An inhibitory mechanism was proposed: the exposure of absorbed microbes on the BiocharA to the highly concentrated phenol in biochar' pores resulted in the inhibition of methanogens, especially for Methanosarcina. In conclusion, this study showed that suitable biochar (BiocharB) could serve as an alternative redox mediator for realizing simultaneously the efficient phenol removal and methane production.
Topics: Anaerobiosis; Carbon; Methane; Phenol; Phenols; Sewage
PubMed: 34329085
DOI: 10.1016/j.jhazmat.2021.126615 -
Physical Chemistry Chemical Physics :... May 2022Although synthesis of oligoaniline (OANI) by persulfate and aniline has been investigated in the recent years, the impact of phenol on the synthesized soluble OANI is...
Although synthesis of oligoaniline (OANI) by persulfate and aniline has been investigated in the recent years, the impact of phenol on the synthesized soluble OANI is still not clear. In this study, our results indicate that phenol and pH mediate the production of the blue water-soluble OANI (OANI) in the reaction between sodium persulfate (SPS) and aniline under alkaline conditions, and the yields of OANI increase with increasing concentrations of phenol and pH values. Quenching experiments rule out the contributions of SO˙ and ˙OH to aniline oxidation and imply that the non-radical activation of SPS is an important pathway in the formation of OANI. MALDI-TOF-MS analysis indicates that phenol apparently inhibits the polymerization degree of aniline in that the molecular weights of OANI gradually decrease from 1586.4 to 684.6 when phenol is increased from 0 to 2.0 mM. FTIR and Raman analyses confirm the structure of aniline oligomers in OANI and indicate that phenol inhibits the phenazine-like structure in OANI and facilitates the transformation of benzenoid rings to quinoid rings in the oxidation products. However, simultaneous activation of SPS by phenol and aniline is likely to occur in the reaction system with the formation of PhNH˙, as indicated by DFT calculations. The high scavenging reactivity of phenol towards both PhNH˙ and PhNH˙ implies that PhNH˙ and PhNH˙ are not the intermediates in the formation of OANI. DFT calculations also reveal that apart from the one-electron transfer pathway between aniline and SPS, the two-electron transfer pathway is also likely to occur in the presence of phenol, resulting in the formation of PhNH/PhN˙˙ without producing PhNH˙ and PhNH˙. The produced PhNH/PhN˙˙ intermediates then couple with aniline, PhNH, aminophenyl sulfate and its hydrolysate to form dimers, trimers, oligomers, and eventually OANI. This study not only describes a novel method to prepare water-soluble OANI, but also gives new insight on the importance of phenol in the production of OANI.
Topics: Aniline Compounds; Oxidation-Reduction; Phenol; Phenols; Sulfates; Water; Water Pollutants, Chemical; Water Purification
PubMed: 35441182
DOI: 10.1039/d1cp05983a -
Food & Function Mar 2024Thermal treatments applied to plant-based foods prior to consumption might influence (poly)phenols' bioaccessibility and the metabolization of these compounds by the gut...
Thermal treatments applied to plant-based foods prior to consumption might influence (poly)phenols' bioaccessibility and the metabolization of these compounds by the gut microbiota. In the present research, the impact of industrial (grilling and canning) and culinary (microwaving and frying) treatments on the bioaccessibility and colonic biotransformations of (poly)phenols from Piquillo pepper () were evaluated by gastrointestinal digestion and colonic fermentation models and HPLC-ESI-MS/MS. The application of industrial treatments impacted positively on (poly)phenols' bioaccessibility compared to raw pepper. Microwaving also exerted a positive effect on (poly)phenols' bioaccessibility compared to canning whereas the addition of oil for frying seemed to negatively affect (poly)phenols' release from the food matrix. Throughout the 48 hours of the colonic fermentation process (poly)phenolic compounds were catabolized into different (poly)phenol derivatives whose formation was also positively affected by industrial and culinary treatments. Based on the concentration and time of appearance of these derivatives, catabolic pathways of (poly)phenols from Piquillo pepper were proposed. The major (poly)phenol derivatives identified (3-(3'-hydroxyphenyl)propanoic acid, 4-hydroxy-3-methoxyphenylacetic acid and benzene-1,2-diol) are considered of great interest for the study of their bioactivity and the potential effect on human health.
Topics: Humans; Phenols; Capsicum; Gastrointestinal Microbiome; Phenol; Tandem Mass Spectrometry; Digestion
PubMed: 38344768
DOI: 10.1039/d3fo04762h -
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 -
Journal of Hazardous Materials Sep 2023Phenols are infamous pollutants in marine environments and present a grave danger to human health, which makes their efficient detection and removal serious issues....
Phenols are infamous pollutants in marine environments and present a grave danger to human health, which makes their efficient detection and removal serious issues. Colorimetry is a simple method for detecting phenols in water because phenols can be oxidized by natural laccase and generate a brown product. However, high cost and poor stability impede the wide-spread implementation of natural laccase in phenol detection. To reverse this adverse situation, a nanoscale Cu-S cluster, Cu(MPPM) (CuS, MPPM = 2-mercapto-5-n-propylpyrimidine), is synthesized. As a stable and inexpensive nanozyme, CuS shows excellent laccase-mimicking activity and prompts the oxidation of phenols. This characteristic makes CuS a perfect option for phenol detection with colorimetry. In addition, CuS also exhibits sulfite activation properties. It can degrade phenols and other pollutants with advanced oxidation processes (AOPs). Theoretical calculations show good laccase-mimicking and sulfite activation properties originating from appropriate interactions between CuS and substrates. We anticipate that the phenol detection and degradation characteristics of CuS make it a promising material to be used for practical phenol remediation in water environments.
Topics: Humans; Phenol; Laccase; Phenols; Environmental Pollutants; Sulfites; Water
PubMed: 37285787
DOI: 10.1016/j.jhazmat.2023.131776 -
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