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Communications Biology Feb 2024Phenolic compounds are industrially versatile chemicals, also the most ubiquitous pollutants. Recently, biosynthesis and biodegradation of phenols has attracted...
Phenolic compounds are industrially versatile chemicals, also the most ubiquitous pollutants. Recently, biosynthesis and biodegradation of phenols has attracted increasing attention, while phenols' toxicity is a major issue. Here, we evolved phloroglucinol-tolerant Escherichia coli strains via adaptive evolution, and three mutations (ΔsodB, ΔclpX and fetAB overexpression) prove of great assistance in the tolerance improvement. We discover that phloroglucinol complexes with iron and promotes the generation of hydroxyl radicals in Fenton reaction, which leads to reducing power depletion, lipid peroxidation, and ferroptosis-like cell death of E. coli. Besides phloroglucinol, various phenols can trigger ferroptosis-like death in diverse organisms, from bacteria to mammalian cells. Furthermore, repressing this ferroptosis-like death improves phloroglucinol production and phenol degradation by corresponding strains respectively, showing great application potential in microbial degradation or production of desired phenolic compounds, and phloroglucinol-induced ferroptosis suppresses tumor growth in mice, indicating phloroglucinol as a promising drug for cancer treatment.
Topics: Mice; Animals; Hydroxyl Radical; Escherichia coli; Ferroptosis; Phenols; Phloroglucinol; Mammals
PubMed: 38368473
DOI: 10.1038/s42003-024-05903-5 -
Food Chemistry Aug 2023The purpose of this study is to investigate the interaction between buckwheat protein and buckwheat phenols in the process of protein extraction and to compare the...
Different interactions between Tartary buckwheat protein and Tartary buckwheat phenols during extraction: Alterations in the conformation and antioxidant activity of protein.
The purpose of this study is to investigate the interaction between buckwheat protein and buckwheat phenols in the process of protein extraction and to compare the effects of phenols on protein structure and antioxidant activity. With the extension of extraction time, the content of total phenol increased from 150.51 to 336.01 mg gallic acid equivalent/g sample. Four phenols and seven phenols were identified by UPLC-Q/TOF-MS as binding to proteins in non-covalent and covalent forms, respectively. The contribution of non-covalent and covalent bound phenols to the antioxidant activity of the complexes were different. Meanwhile, the binding of phenols changed the infrared characteristic peak of protein, and reduced the fluorescence intensity and surface hydrophobic value. The free amino and sulfhydryl content of the protein decreased with increasing extraction time. These findings provide valuable information for one-step preparation of protein-phenol complexes.
Topics: Antioxidants; Fagopyrum; Gallic Acid; Phenol; Phenols; Plant Extracts
PubMed: 37001350
DOI: 10.1016/j.foodchem.2023.135711 -
Food & Function Nov 2023(Poly)phenol (PP)-rich blackcurrant (BC) extracts reduce postprandial glucose concentrations. Combinations with other fruit (poly)phenols and fruit fibre may enhance the...
Acute effects of drinks containing blackcurrant and citrus (poly)phenols and dietary fibre on postprandial glycaemia, gut hormones, cognitive function and appetite in healthy adults: two randomised controlled trials.
(Poly)phenol (PP)-rich blackcurrant (BC) extracts reduce postprandial glucose concentrations. Combinations with other fruit (poly)phenols and fruit fibre may enhance the effect. This study investigated the acute effects of combinations of BC extracts, high (H-BC) and low (L-BC) (poly)phenol concentrations, sweet orange extracts (SO) and fibre-rich orange pulp (F) in reducing postprandial glycaemia. In two randomised, double-blind, crossover design studies, healthy participants consumed seven types of 200 mL beverages: in the GLU-FX trial, H-BC (1600 mg PP); L-BC (800 mg PP); SO (800 mg PP); BC + SO (1600 mg PP) or CON (placebo); in the GLU-MIX trial, BC + F (800 mg PP), F (1.5 g fibre), or CON2 (placebo), immediately followed by consumption of 75 g available carbohydrate (starch and sugars). Blood was sampled at baseline and postprandially to measure changes in glucose, insulin, and gut hormones; appetite changes were assessed by visual analogue scales and, in GLU-MIX, food intake and cognitive function were assessed. Twenty-nine and thirty-seven adults completed GLU-FX and GLU-MIX, respectively. L-BC reduced early postprandial glycaemia (0-30 min) with no differences in glucose incremental or total glycaemic response. No significant effect was observed following other drinks relative to CON. L-BC and H-BC drinks inhibited insulin secretion up to 30 min and GIP up to 120 min. In GLU-MIX, BC + F improved some indicators of cognitive function but not all. Measures of appetite were unaffected. The impact of (poly)phenol-rich BC extracts on total postprandial glycaemia in healthy participants was minimal and not enhanced when administered in combination with an orange (poly)phenol extract or orange pulp. Clinical Trials registered at https://www.clinicaltrials.gov: NCT03184064 (GLU-FX) and NCT03572296 (GLU-MIX).
Topics: Humans; Adult; Appetite; Blood Glucose; Phenols; Citrus; Phenol; Glucose; Dietary Fiber; Gastrointestinal Hormones; Insulin; Cognition; Postprandial Period; Cross-Over Studies; Randomized Controlled Trials as Topic
PubMed: 37902089
DOI: 10.1039/d3fo03085g -
European Journal of Medicinal Chemistry Dec 2023Erianin, a bioactive compound extracted from Dendrobium, a traditional Chinese medicine, exhibits remarkable anti-cancer properties through diverse molecular mechanisms... (Review)
Review
Erianin, a bioactive compound extracted from Dendrobium, a traditional Chinese medicine, exhibits remarkable anti-cancer properties through diverse molecular mechanisms and has attracted the attention of medicinal chemists. However, the low solubility in water, rapid metabolism and elimination from the body lead to poor bioavailability of Erianin, and greatly hinder its clinical application. The development of new Erianin derivatives is continuously proceed to improve its anticancer effects. In recent years, although important progress in the development of Erianin and the publication of some reviews in this aspect, the mechanism against various cancers, pharmacokinetic study, structural modification as well as structure-activity relationships have not been thoroughly considered. This review is aimed at providing complete picture regarding the above aspects by reviewing studies from 2000 to 2023.06. This review also supplies some important viewpoints on the design and future directions for the development of Erianin derivatives as possible clinically effective anticancer agents.
Topics: Cell Line, Tumor; Bibenzyls; Phenol; Antineoplastic Agents
PubMed: 37804769
DOI: 10.1016/j.ejmech.2023.115844 -
Nature Sep 2023Plywood is widely used in construction, such as for flooring and interior walls, as well as in the manufacture of household items such as furniture and cabinets. Such...
Plywood is widely used in construction, such as for flooring and interior walls, as well as in the manufacture of household items such as furniture and cabinets. Such items are made of wood veneers that are bonded together with adhesives such as urea-formaldehyde and phenol-formaldehyde resins. Researchers in academia and industry have long aimed to synthesize lignin-phenol-formaldehyde resin adhesives using biomass-derived lignin, a phenolic polymer that can be used to substitute the petroleum-derived phenol. However, lignin-phenol-formaldehyde resin adhesives are less attractive to plywood manufacturers than urea-formaldehyde and phenol-formaldehyde resins owing to their appearance and cost. Here we report a simple and practical strategy for preparing lignin-based wood adhesives from lignocellulosic biomass. Our strategy involves separation of uncondensed or slightly condensed lignins from biomass followed by direct application of a suspension of the lignin and water as an adhesive on wood veneers. Plywood products with superior performances could be prepared with such lignin adhesives at a wide range of hot-pressing temperatures, enabling the use of these adhesives as promising alternatives to traditional wood adhesives in different market segments. Mechanistic studies indicate that the adhesion mechanism of such lignin adhesives may involve softening of lignin by water, filling of vessels with softened lignin and crosslinking of lignins in adhesives with those in the cell wall.
Topics: Adhesives; Formaldehyde; Lignin; Phenols; Urea; Water; Wood; Biomass; Hot Temperature
PubMed: 37553075
DOI: 10.1038/s41586-023-06507-5 -
Journal of Food Science Dec 2023Sorghum 3-deoxyanthocyanins (3-DXAs) have greater stability when compared to other anthocyanins. However, the efficiency in extracting these phenolic compounds from...
Sorghum 3-deoxyanthocyanins (3-DXAs) have greater stability when compared to other anthocyanins. However, the efficiency in extracting these phenolic compounds from cereals, using conventional methods, is low, because most of them are bound to the cell wall. Thus, the aim of this study was to optimize the ultrasound-assisted extraction (UAE) of anthocyanins and total phenolics from sorghum flour, and evaluate the stability of the 3-DXAs. Two frequencies (25 and 45 kHz) were applied in a Central Composite Rotational design to investigate the effect of the variables time (5-75 min) and temperature (30-65°C) using the UAE, with amplitude of the ultrasonic power set at 400 W. In addition, the stability of the 3-DXAs present in the extracts was evaluated. It was possible to successfully optimize the extraction of total anthocyanins (both frequencies) and phenolics (at 45 kHz), and then to obtain equations, to predict their concentrations, with high R . The efficiency of UAE was observed, increasing the yield of total anthocyanins, phenolics, and antioxidant capacity at the frequencies of 25 and 45 kHz by 30% and 27%, 10% and 5%, and 30% and 15%, respectively. The apigeninidin was the major 3-DXA found in the extracts, and the luteolinidin was the most stable over storage time. Overall, there was no difference in the 3-DXAs stability obtained by the UAE compared to the conventional method. Thus, ultrasound is an alternative to obtaining sorghum extracts rich in 3-DXAs and other phenolic compounds. PRACTICAL APPLICATION: The health benefits of sorghum 3-deoxyanthocyanins coupled with the growing interest of the food industry in producing healthier food products have motivated this study, because it is important to find ways to optimize 3-deoxyanthocyanins extraction. We have demonstrated that ultrasound-assisted extraction was efficient in extracting high amounts of 3-deoxyanthocyanins and other phenolics from sorghum flour. Moreover, some 3-deoxyanthocyanins have shown to be more stable than others after extraction. Thus, the ultrasound has great potential to produce sorghum phenolic extracts rich in 3-deoxyanthocyanins, which can be used as natural colorants and functional ingredients in foods.
Topics: Anthocyanins; Edible Grain; Sorghum; Plant Extracts; Phenols; Antioxidants
PubMed: 37942949
DOI: 10.1111/1750-3841.16826 -
Phytotherapy Research : PTR Apr 2024In recent years, heightened interest surrounds the exploration of natural phenols as potential agents for cancer therapy, specifically by inducing ferroptosis, a unique... (Review)
Review
In recent years, heightened interest surrounds the exploration of natural phenols as potential agents for cancer therapy, specifically by inducing ferroptosis, a unique form of regulated cell death characterized by iron-dependent lipid peroxidation. This review delves into the roles of key natural phenols, flavonoids, phenolic acids, curcumin, and stilbenes, in modulating ferroptosis and their underlying mechanisms. Emphasizing the significance of amino acid, lipid, and iron metabolism, the study elucidates the diverse pathways through which these phenols regulate ferroptosis. Notably, curcumin, a well-known polyphenol, exhibits multifaceted interactions with cellular components involved in ferroptosis regulation, providing a distinctive therapeutic avenue. Stilbenes, another phenolic class, demonstrate promising potential in influencing lipid metabolism and iron-dependent processes, contributing to ferroptotic cell death. Understanding the intricate interplay between these natural phenols and ferroptosis not only illuminates complex cellular regulatory networks but also unveils potential avenues for novel cancer therapies. Exploring these compounds as inducers of ferroptosis presents a promising strategy for targeted cancer treatment, capitalizing on the delicate balance between cellular metabolism and regulated cell death mechanisms. This article synthesizes current knowledge, aiming to stimulate further research into the therapeutic potential of natural phenols in the context of ferroptosis-mediated cancer therapy.
Topics: Phenols; Ferroptosis; Curcumin; Iron; Stilbenes; Neoplasms
PubMed: 38391022
DOI: 10.1002/ptr.8149 -
Food Research International (Ottawa,... Dec 2023The molecular and biofunctional properties of protein and phenolic fractions in edible truffles remain largely unknown. This study examined the effect of ultrasonication...
Impact of ultrasonication on the contents, profiles and biofunctional properties of free and bound phenolics from white desert truffle (Tirmania nivea) and its protein fractions.
The molecular and biofunctional properties of protein and phenolic fractions in edible truffles remain largely unknown. This study examined the effect of ultrasonication on the contents, profiles, and bioactive properties of free and bound phenolics (FP and BP) from desert truffle (Tirmania nivea) and its protein fractions. Protein fractions from the Osborne extraction scheme were biochemically and structurally characterized. The albumin fraction showed the highest abundance (16.8%) and yield (35.8%). Total phenolic contents were the highest in non-sonicated samples (3.5-34.1 mg/g), particularly in the albumin fraction and in whole truffle. FP extracted at 30 °C (FP-30 °C) accounted for the largest proportion of total phenolics in all protein fractions, whereas BP-30 °C and FP-60 °C were predominant in non-sonicated and sonicated truffle, respectively. The highest antioxidant activity was obtained with FP-30 °C extracts from non-sonicated albumins, globulins and truffle (91.9, 72.7 and 30.0%), followed by BP-30 °C from non-sonicated albumins (25.4%) and FP-60 °C from sonicated glutelins-1 (24.2%). High inhibition of α-amylase was evidenced in several extracts, including FP-30 °C from non-sonicated glutelins-1 (99.2%) and FP-30 °C from sonicated globulins (72.4%). Several extracts also displayed high inhibition of angiotensin I-converting enzyme (ACE), including FP-60 °C from non-sonicated glutelins-1 (65.1%) and sonicated glutelins-1 (71.1%) and globulins (64.7%). Most extracts were rich in epicatechin, gallic acid, chlorogenic acid and catechin. Correlations between phenolic content, antioxidant activity, anti-α-amylase and anti-ACE activities were influenced by sonication. Sonication reduced the particle size of the proteins and modified their structural characteristics. These findings demonstrate that white desert truffle proteins co-occur with bioactive phenolics whose functionalities can be tailored by protein fractionation and sonication.
Topics: Antioxidants; Phenols; Catechin; alpha-Amylases; Albumins; Globulins; Glutens
PubMed: 37986408
DOI: 10.1016/j.foodres.2023.113453 -
Food Research International (Ottawa,... Oct 2023Cranberry (poly)phenols may have potential health benefits. Circulating (poly)phenol metabolites can act as mediators of these effects, but they are subjected to an... (Randomized Controlled Trial)
Randomized Controlled Trial
Cranberry (poly)phenols may have potential health benefits. Circulating (poly)phenol metabolites can act as mediators of these effects, but they are subjected to an extensive inter-individual variability. This study aimed to quantify both plasma and urine (poly)phenol metabolites following a 12-week intake of a cranberry powder in healthy older adults, and to investigate inter-individual differences by considering the existence of urinary metabotypes related to dietary (poly)phenols. Up to 13 and 67 metabolites were quantified in plasma and urine respectively. Cranberry consumption led to changes in plasma metabolites, mainly hydroxycinnamates and hippuric acid. Individual variability in urinary metabolites was assessed using different data sets and a combination of statistical models. Three phenolic metabotypes were identified, colonic metabolism being the main driver for subject clustering. Metabotypes were characterized by quali-quantitative differences in the excretion of some metabolites such as phenyl-γ-valerolactones, hydroxycinnamic acids, and phenylpropanoic acids. Metabotypes were further confirmed when applying a model only focused on flavan-3-ol colonic metabolites. 5-(3',4'-dihydroxyphenyl)-γ-valerolactone derivatives were the most relevant metabolites for metabotyping. Metabotype allocation was well preserved after 12-week intervention. This metabotyping approach for cranberry metabolites represents an innovative step to handle the complexity of (poly)phenol metabolism in free-living conditions, deciphering the existence of metabotypes derived from the simultaneous consumption of different classes of (poly)phenols. These results will help contribute to studying the health effects of cranberries and other (poly)phenol-rich foods, mainly considering gut microbiota-driven individual differences.
Topics: Phenol; Vaccinium macrocarpon; Phenols; Cluster Analysis; Dietary Supplements
PubMed: 37689939
DOI: 10.1016/j.foodres.2023.113187 -
Scientific Reports Nov 2023Phenol, an important bioactive substance in jujube fruit, is one of the most important indexes of fruit quality. In order to clarify the phenolic substance composition,...
Phenol, an important bioactive substance in jujube fruit, is one of the most important indexes of fruit quality. In order to clarify the phenolic substance composition, content and distribution characteristics of different varieties of jujube fruits, this study measured and compared the content of total phenols, total flavonoids and phenolic substance composition in different parts of fruits of six jujube varieties, and combined with the principal component analysis, the results showed that: Fourteen phenolic substances were identified in the fruits of different jujube varieties, and proanthocyanidins, epicatechin, catechin and rutin were the main components, accounting for 58.60%, 16.08%, 13.56% and 5.57% of the total phenolic substances, respectively. The total phenolic and total flavonoid contents of jujube fruits of each variety were between 18.11 and 21.45 mg GAE/g DW and 10.56-20.25 mg RE/g DW, respectively, and the differences in the contents between the varieties were significant, and the contents of 'Junzao' and 'Jinlingyuanzao' were higher than those of other varieties.The phenolic content of different parts of jujube fruits showed spatial distribution differences, manifested as the total phenols, total flavonoids and their fractions of the peel were significantly higher than that of the pulp, while the content of the pulp near the kernel was significantly higher than that of other parts of the pulp, This study provides a theoretical basis for analysing the differences in phenolic substances in jujube fruits.
Topics: Fruit; Ziziphus; Antioxidants; Phenols; Flavonoids; Catechin
PubMed: 37919376
DOI: 10.1038/s41598-023-46228-3