-
Biomedicine & Pharmacotherapy =... Jan 2024The tobacco use is one of the biggest public health threats worldwide. Cigarette smoke contains over 7000 chemicals among other aldehydes, regarded as priority...
BACKGROUND
The tobacco use is one of the biggest public health threats worldwide. Cigarette smoke contains over 7000 chemicals among other aldehydes, regarded as priority toxicants. β-escin (a mixture of triterpenoid saponins extracted from the Aesculus hippocastanum. L) is a potent activator of aldehyde dehydrogenase (ALDH) - an enzyme catalyzing oxidation of aldehydes to non-toxic carboxylic acids.
PURPOSE
The aim of this study was to evaluate the effect of β-escin on ALDH activity, ALDH isoforms mRNA expression and cytotoxicity in nasal epithelial cells exposed to cigarette smoke extract (CSE).
METHODS
Nasal epithelial cells from healthy non-smokers were treated with β-escin (1 µM) and exposed to 5% CSE. After 6- or 24-hours of stimulation cell viability, DNA damage, ALDH activity and mRNA expression of ALDH isoforms were examined.
RESULTS
24 h β-escin stimulation revised CSE induced cytotoxicity and DNA damage. Cells cultured with β-escin or exposed to CSE responded with strong increase in ALDH activity. This effect was more pronounced in cultures treated with combination of β-escin and CSE. The strongest stimulatory effect on ALDH isoform mRNA expression was observed in cells cultured simultaneously with β-escin and CSE: at 6 h for ALDH1A1 and ALDH3A1, and at 24 h for ALDH1A3, ALDH3A2, ALDH3B1, and ALDH18A1. Combined β-escin and CSE treatment prevented the CSE-induced inhibition of ALDH2 expression at 24 h.
CONCLUSIONS
β-escin is an effective ALDH stimulatory and cytoprotective agent and might be useful in the prevention or supportive treatment of tobacco smoke-related diseases.
Topics: Aldehyde Dehydrogenase; Escin; Cigarette Smoking; Epithelial Cells; Aldehydes; Cell Death; RNA, Messenger; Protein Isoforms; Cell Survival; Tobacco Products
PubMed: 38016364
DOI: 10.1016/j.biopha.2023.115924 -
Angewandte Chemie (International Ed. in... Jul 2023The demand for new biomass-derived fine and commodity chemicals propels the discovery of new methodologies and synthons. Whereas furfural and 5-hydroxymethylfurfural are...
The demand for new biomass-derived fine and commodity chemicals propels the discovery of new methodologies and synthons. Whereas furfural and 5-hydroxymethylfurfural are cornerstones of sustainable chemistry, 3-acetamido-5-acetyl furan (3A5AF), an N-rich furan obtained from chitin biomass, remains unexplored, due to the poor reactivity of the acetyl group relative to previous furanic aldehydes. Here we developed a reactive 3-acetamido-5-furfuryl aldehyde (3A5F) and demonstrated the utility of this synthon as a source of bio-derived nitrogen-rich heteroaromatics, carbocycles, and as a bioconjugation reagent.
Topics: Biomass; Furans; Furaldehyde; Aldehydes; Chitin
PubMed: 37142557
DOI: 10.1002/anie.202304449 -
Journal of the Science of Food and... Mar 2024Extra virgin olive oil (EVOO), a natural product with a multidisciplinary role, has been and is continuing to be studied from several points of view. Among them, its...
BACKGROUND
Extra virgin olive oil (EVOO), a natural product with a multidisciplinary role, has been and is continuing to be studied from several points of view. Among them, its chemical analysis is of major importance and several methods have been used. Nuclear magnetic resonance (NMR) spectroscopy has inherent advantages, among them monitoring the chemical constituents without the need for a separation technique and without, for instance, possible carry-over effects. Additionally, several magnetic resonance spectroscopic techniques can provide a novel powered insight into the nature and properties of a sample under study. Moreover, -omics procedure can reveal new information and can lead to the classification of populations under study. The main objective of the present work was the possible classification of the EVOO samples based on their aldehyde content using a proposed unreferenced H-NMR spectroscopic quantification method combined with a metabolomic approach. Moreover, the study of the impact of such elevated aldehyde content on several spectra regions of importance in the proton NMR spectra led to the proposal of a possible new isomer indicator.
RESULTS
Univariate analysis of 12 EVOO samples showed that oleacein, oleocanthal, elenolic acid, hydroxytyrosol/hydroxytyrosol derivatives and tyrosol/tyrosol derivatives strongly differentiated two classes of EVOO: OEH (for high aldehyde EVOO content) and OE (for non-high aldehyde content). Moreover, we pointed out the 'impact' of such elevated secoiridoid and derivatives content, through their moieties' units, on a range of several resonances of the H-NMR spectrum. The metabolomic approach demonstrated the classification of EVOO samples based on their secoiridoid and derivatives content. Multivariate analysis showed a strong influence on the discrimination of the EVOO classes based on the protons resonating at the aldehyde region of the H-NMR spectrum; the aldehyde protons corresponding to 5S,4R-ligstrodial and 5S,4R-oleuropeindial, oleacein, oleocanthal, elenolic acid, p-HPEA-EA, 3,4-DHPEA-EA, 5S,4R- and 5S,4S-ligstrodial and the proton corresponding to a new compound were reported for the first time. This isomer compound, reported for the first time, could serve as a possible indicator for EVOO classification.
CONCLUSIONS
An unreferenced quantification method was proposed and EVOO samples were classified into two classes: OEH and OE, according to their aldehyde content, gaining thus probably higher nutrient and possible pharmacological value. Moreover, we point out the 'impact' of such elevated aldehyde content on several spectral regions of the H spectrum. Finally, a new compound was detected in the OEH samples and is reported for the first time. This compound could possibly be an indicator. © 2023 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
Topics: Olive Oil; Iridoids; Protons; Aldehydes; Magnetic Resonance Spectroscopy; Cyclopentane Monoterpenes; Phenylethyl Alcohol; Phenols
PubMed: 38018400
DOI: 10.1002/jsfa.13139 -
ACS Applied Materials & Interfaces Apr 2024Changeable substituent groups of organic molecules can provide an opportunity to clarify the antibacterial mechanism of organic molecules by tuning the electron cloud...
Changeable substituent groups of organic molecules can provide an opportunity to clarify the antibacterial mechanism of organic molecules by tuning the electron cloud density of their skeleton. However, understanding the antibacterial mechanism of organic molecules is challenging. Herein, we reported a molecular view strategy for clarifying the antibacterial switch mechanism by tuning electron cloud density of cinnamaldehyde molecule skeleton. The cinnamaldehyde and its derivatives were self-assembled into nanosheets with excellent water solubility, respectively. The experimental results show that α-bromocinnamaldehyde (BCA) nanosheets exhibits unprecedented antibacterial activity, but there is no antibacterial activity for α-methylcinnamaldehyde nanosheets. Therefore, the BCA nanosheets and α-methylcinnamaldehyde nanosheets achieve an antibacterial switch. Theoretical calculations further confirmed that the electron-withdrawing substituent of the bromine atom leads to a lower electron cloud density of the aldehyde group than that of the electron-donor substituent of the methyl group at the α-position of the cinnamaldehyde skeleton, which is a key point in elucidating the antimicrobial switch mechanism. The excellent biocompatibility of BCA nanosheets was confirmed by CCK-8. The mouse wound infection model, H&E staining, and the crawling ability of drosophila larvae show that as-prepared BCA nanosheets are safe and promising for wound healing. This study provides a new strategy for the synthesis of low-cost organic nanomaterials with good biocompatibility. It is expected to expand the application of natural organic small molecule materials in antimicrobial agents.
Topics: Mice; Animals; Nanostructures; Anti-Bacterial Agents; Acrolein; Skeleton
PubMed: 38556984
DOI: 10.1021/acsami.3c18277 -
Journal of Affective Disorders Jan 2024Humans have many opportunities to be exposed to aldehydes which have potential mechanisms for causing depression. We aimed to explore the relationships between serum...
BACKGROUND
Humans have many opportunities to be exposed to aldehydes which have potential mechanisms for causing depression. We aimed to explore the relationships between serum individual and mixed aldehydes with depressive symptoms in general population.
METHODS
The data was extracted from the National Health and Nutrition Examination Survey 2013-2014. Depressive symptoms were assessed by Patient Health Questionnaire-9. Weighted binomial logistic regression and Bayesian kernel machine regression (BKMR) model were used to explore the association of six individual aldehyde and mixed aldehydes with depressive symptoms, respectively. Sex stratification analysis and sensitivity analysis were conducted.
RESULTS
A total of 701 participants were included. We found a positive association between the highest (Q4) versus lowest quartile (Q1) of butyraldehyde with depressive symptoms (OR: 2.86, 95 % CI: 1.22-6.68), and a negative association between the Q3 versus Q1 of benzaldehyde (0.21, 0.07-0.60) and isopentanaldehyde (0.28, 0.08-0.90) with depressive symptoms in multivariate-adjusted model. The mixed aldehydes were positively associated with depressive symptoms using BKMR model, and butyraldehyde and heptanaldehyde were the dominant aldehydes. Several aldehydes, such as butyraldehyde and benzaldehyde, interacted with each other in their effects on depressive symptoms. The results of gender stratification analysis showed that butyraldehyde was the major contributor to the total effect of aldehydes on depressive symptoms in males, while heptanaldehyde was the dominant aldehyde in females.
LIMITATIONS
Causality cannot be inferred in this cross-sectional study.
CONCLUSIONS
Our study indicated that mixed aldehydes can increase the risk of depressive symptoms, of which butyraldehyde and heptanaldehyde were the major contributing aldehydes.
Topics: Male; Female; Humans; Depression; Benzaldehydes; Nutrition Surveys; Cross-Sectional Studies; Bayes Theorem; Aldehydes; Machine Learning
PubMed: 37865348
DOI: 10.1016/j.jad.2023.10.123 -
Journal of Agricultural and Food... Aug 2023During beer and wine production, Maillard reaction products (MRPs) are formed, which have a particular influence on the taste and aroma of the fermented beverages....
During beer and wine production, Maillard reaction products (MRPs) are formed, which have a particular influence on the taste and aroma of the fermented beverages. Compared to beer, less is known about individual Maillard compounds and especially corresponding yeast metabolites in wine. In this study, 36 selected wines (Amarone, Ripasso, red, and white wines) were analyzed by HPLC-UV and GC-MS concerning the amounts of 3-deoxyglucosone (3-DG), 3-deoxygalactosone (3-DGal), methylglyoxal (MGO), glyoxal (GO), 5-hydroxymethylfurfural (HMF), and furfural (FF). 3-DG was found to be the dominant compound with values from 3.3 to 35.1 mg/L. The contents of 3-DGal, MGO, GO, HMF, and FF were in a single digit range. In addition to MRPs, the yeast metabolites originating from 3-DG, namely, 3-deoxyfructose and 3-deoxy-2-ketogluconic acid, 2,5-bis(hydroxymethyl)furan and 5-formyl-2-furancarboxylic acid, both formed from HMF, and the FF metabolites furfuryl alcohol and furan-2-carboxylic acid were detected and quantitated in wines for the first time. The amounts were between 0.1 and 53.5 mg/L with especially high contents of the oxidation products. Differences between red and white wines indicate that enological parameters like grape variety, production method, and aging may have an influence on the MRP contents in wines.
Topics: Saccharomyces cerevisiae; Wine; Maillard Reaction; Magnesium Oxide; Pyruvaldehyde; Glyoxal; Glycation End Products, Advanced
PubMed: 37530036
DOI: 10.1021/acs.jafc.3c04512 -
Environmental Science and Pollution... Nov 2023This study aims to produce beneficial products with pomegranate peel waste through pyrolysis. For this purpose, the usability of the liquid product as a biofuel and the...
This study aims to produce beneficial products with pomegranate peel waste through pyrolysis. For this purpose, the usability of the liquid product as a biofuel and the solid product as an adsorbent for dye removal was investigated. To characterize the bio-oil and biochar produced under the best pyrolysis conditions, Fourier transforms infrared spectroscopy (FT-IR), Gas chromatography-mass spectrometry (GC-MS), calorific value, Brunauer-Emmett-Teller (BET), and Scanning electron microscopy (SEM) analyses were conducted. When we examine the FT-IR spectrum of the bio-oil, the presence of phenol, alcohol, ketone, and aldehyde groups is seen in the structure. The GC-MS analysis demonstrated that phenol content was 27.9%, aldehyde content was 19%, acid compound content was 18.28%, ketone content was 8.7%, and aromatic compound content was 8.4%. The lower calorific value of bio-oil was determined as 27.33 MJ/kg. It was observed that activated carbon produced from biochar at a 3:1 KOH/biochar impregnation ratio and a carbonization temperature of 800 °C exhibited the highest surface area (1307 m/g). In adsorption analysis, it was observed that the adsorption efficiency was higher at pH 9 and 35 °C and with 150 ppm initial concentration. Langmuir and Freundlich adsorption isotherms were determined, and the high R (0.99) was consistent with the Langmuir methylene blue (MB) adsorption model.
Topics: Charcoal; Pomegranate; Pyrolysis; Spectroscopy, Fourier Transform Infrared; Phenols; Phenol; Adsorption; Aldehydes; Ketones; Kinetics
PubMed: 37880403
DOI: 10.1007/s11356-023-30527-3 -
Sheng Wu Gong Cheng Xue Bao = Chinese... Aug 2023ω-transaminases are able to catalyze the reversible transfer of amino groups between diverse amino compounds (such as amino acids, alkyl amines, aromatic amines) and... (Review)
Review
ω-transaminases are able to catalyze the reversible transfer of amino groups between diverse amino compounds (such as amino acids, alkyl amines, aromatic amines) and carbonyl compounds (such as aldehydes, ketones, ketoacids). ω-transaminases exhibit great application prospects in the field of chiral amine biosynthesis because of their desirable properties, such as wide range of substrates, high stereoselectivity, and mild catalytic conditions. It is therefore important for China to develop efficient, specific, and environment-friendly chiral amine production technologies with independent intellectual property rights, which is of great significance for the development of pharmaceutical, pesticide, and material industries. This review systematically summarizes the Chinese patents regarding ω-transaminase filed by Chinese institutions in the recent decade. The development of ω-transaminase resource, enzymatic property improvement by protein engineering, application in chiral amine synthesis, and development of production technologies are elaborated. This review will shed light on further basic and application studies of ω-transaminase.
Topics: Transaminases; Amino Acids; China; Aldehydes; Amines
PubMed: 37622354
DOI: 10.13345/j.cjb.220908 -
Nutrition Research Reviews Dec 2023Many epidemiological studies have emphasised the relation between carotenoid dietary intake and their circulating concentrations and beneficial health effects, such as... (Review)
Review
Many epidemiological studies have emphasised the relation between carotenoid dietary intake and their circulating concentrations and beneficial health effects, such as lower risk of cardiometabolic diseases and cancer. However, there is dispute as to whether the attributed health benefits are due to native carotenoids or whether they are instead induced by their metabolites. Several categories of metabolites have been reported, most notably involving (a) modifications at the cyclohexenyl ring or the polyene chain, such as epoxides and geometric isomers, (b) excentric cleavage metabolites with alcohol-, aldehyde- or carboxylic acid-functional groups or (c) centric cleaved metabolites with additional hydroxyl, aldehyde or carboxyl functionalities, not counting their potential phase-II glucuronidated / sulphated derivatives. Of special interest are the apo-carotenoids, which originate in the intestine and other tissues from carotenoid cleavage by β-carotene oxygenases 1/2 in a symmetrical / non-symmetrical fashion. These are more water soluble and more electrophilic and, therefore, putative candidates for interactions with transcription factors such as NF-kB and Nrf2, as well as ligands for RAR-RXR nuclear receptor interactions. In this review, we discuss detected apo-carotenoids, their reported tissue concentrations, and potential associated health effects, focusing exclusively on the human situation and based on quantified / semi-quantified carotenoid metabolites proven to be present in humans.
Topics: Humans; Retinoids; Carotenoids; Neoplasms; Aldehydes
PubMed: 36380523
DOI: 10.1017/S095442242200021X -
Free Radical Biology & Medicine Oct 2023Acrolein, which is the most reactive aldehyde, is a byproduct of lipid peroxidation in a hypoxic environment. Acrolein has been shown to form acrolein-cysteine bonds,...
Acrolein, which is the most reactive aldehyde, is a byproduct of lipid peroxidation in a hypoxic environment. Acrolein has been shown to form acrolein-cysteine bonds, resulting in functional changes in proteins and immune effector cell suppression. Neutrophils are the most abundant immune effector cells in circulation in humans. In the tumor microenvironment, proinflammatory tumor-associated neutrophils (TANs), which are termed N1 neutrophils, exert antitumor effects via the secretion of cytokines, while anti-inflammatory neutrophils (N2 neutrophils) support tumor growth. Glioma is characterized by significant tissue hypoxia, immune cell infiltration, and a highly immunosuppressive microenvironment. In glioma, neutrophils exert antitumor effects early in tumor development but gradually shift to a tumor-supporting role as the tumor develops. However, the mechanism of this anti-to protumoral switch in TANs remains unclear. In this study, we found that the production of acrolein in glioma cells under hypoxic conditions inhibited neutrophil activation and induced an anti-inflammatory phenotype by directly reacting with Cys310 of AKT and inhibiting AKT activity. A higher percentage of cells expressing acrolein adducts in tumor tissue are associated with poorer prognosis in glioblastoma patients. Furthermore, high-grade glioma patients have increased serum acrolein levels and impaired neutrophil functions. These results suggest that acrolein suppresses neutrophil function and contributes to the switch in the neutrophil phenotype in glioma.
Topics: Humans; Acrolein; Neutrophils; Proto-Oncogene Proteins c-akt; Glioblastoma; Anti-Inflammatory Agents; Tumor Microenvironment
PubMed: 37414347
DOI: 10.1016/j.freeradbiomed.2023.06.027