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1.
Acta Biochim Biophys Sin (Shanghai) ; 56(7): 963-972, 2024 Jun 03.
Article in English | MEDLINE | ID: mdl-38993132

ABSTRACT

Endothelial dysfunction (ED) serves as the pathological basis for various cardiovascular diseases. Guanosine triphosphate cyclopyrrolone 1 (GCH1) emerges as a pivotal protein in sustaining nitric oxide (NO) production within endothelial cells, yet it undergoes degradation under oxidative stress, contributing to endothelial cell dysfunction. Citronellal (CT), a monoterpenoid, has been shown to ameliorate endothelial dysfunction induced by in atherosclerosis rats. However, whether CT can inhibit the degradation of GCH1 protein is not clear. It has been reported that ubiquitination may play a crucial role in regulating GCH1 protein levels and activities. However, the specific E3 ligase for GCH1 and the molecular mechanism of GCH1 ubiquitination remain unclear. Using data-base exploration analysis, we find that the levels of the E3 ligase Smad-ubiquitination regulatory factor 2 (Smurf2) negatively correlate with those of GCH1 in vascular tissues and HUVECs. We observe that Smurf2 interacts with GCH1 and promotes its degradation via the proteasome pathway. Interestingly, ectopic Smurf2 expression not only decreases GCH1 levels but also reduces cell proliferation and reactive oxygen species (ROS) levels, mostly because of increased GCH1 accumulation. Furthermore, we identify BH 4/eNOS as downstream of GCH1. Taken together, our results indicate that CT can obviously improve vascular endothelial injury in Type 1 diabetes mellitus (T1DM) rats and reverse the expressions of GCH1 and Smurf2 proteins in aorta of T1DM rats. Smurf2 promotes ubiquitination and degradation of GCH1 through proteasome pathway in HUVECs. We conclude that the Smurf2-GCH1 interaction might represent a potential target for improving endothelial injury.


Subject(s)
Acyclic Monoterpenes , Human Umbilical Vein Endothelial Cells , Ubiquitin-Protein Ligases , Animals , Ubiquitin-Protein Ligases/metabolism , Ubiquitin-Protein Ligases/genetics , Humans , Human Umbilical Vein Endothelial Cells/metabolism , Acyclic Monoterpenes/pharmacology , Acyclic Monoterpenes/metabolism , Rats , Ubiquitination , Aldehydes/metabolism , Reactive Oxygen Species/metabolism , Male , Rats, Sprague-Dawley , Nitric Oxide/metabolism , Cell Proliferation , Protein Stability , Endothelium, Vascular/metabolism , Endothelium, Vascular/pathology , Oxidative Stress
2.
Cell Death Dis ; 15(7): 546, 2024 Jul 31.
Article in English | MEDLINE | ID: mdl-39085238

ABSTRACT

Non-small cell lung cancer (NSCLC) is among the most prevalent cancers and a leading cause of cancer-related mortality globally. Extracellular vesicles (EVs) derived from NSCLC play a pivotal role in lung cancer progression. Our findings reveal a direct correlation between the abundance of EVs and the transfection efficiencies. Co-culturing two different lung cancer cell lines could enhance EVs formation, cell proliferation, migration and tumorigenicity. mRNA chip and metabolic analyses revealed significant alterations in the FOXO signaling pathway and unsaturated fatty acid metabolism within tumor tissues derived from co-cultured cells. Shotgun lipidomics studies and bioinformatics analyses guided our attention towards 4-Hydroxynonenal (4-HNE) and FOXO4. Elevating 4-HNE or FOXO4 levels could reduce the formation of EVs and impede cell growth and migration. While silencing FOXO4 expression lead to an increase in cell cloning rate and enhanced migration. These findings suggest that regulating the production of 4-HNE and FOXO4 might provide an effective therapeutic approach for the treatment of NSCLC.


Subject(s)
Aldehydes , Carcinoma, Non-Small-Cell Lung , Cell Movement , Cell Proliferation , Down-Regulation , Forkhead Transcription Factors , Lung Neoplasms , Humans , Carcinoma, Non-Small-Cell Lung/pathology , Carcinoma, Non-Small-Cell Lung/metabolism , Carcinoma, Non-Small-Cell Lung/genetics , Cell Movement/genetics , Forkhead Transcription Factors/metabolism , Forkhead Transcription Factors/genetics , Lung Neoplasms/pathology , Lung Neoplasms/metabolism , Lung Neoplasms/genetics , Aldehydes/metabolism , Down-Regulation/genetics , Cell Line, Tumor , Cell Cycle Proteins/metabolism , Cell Cycle Proteins/genetics , Animals , Gene Expression Regulation, Neoplastic , Extracellular Vesicles/metabolism , Mice , Signal Transduction , Mice, Nude
3.
Sci Rep ; 14(1): 15174, 2024 07 02.
Article in English | MEDLINE | ID: mdl-38956161

ABSTRACT

Coronary artery bypass surgery can result in endothelial dysfunction due to ischemia/reperfusion (IR) injury. Previous studies have demonstrated that DuraGraft helps maintain endothelial integrity of saphenous vein grafts during ischemic conditions. In this study, we investigated the potential of DuraGraft to mitigate endothelial dysfunction in arterial grafts after IR injury using an aortic transplantation model. Lewis rats (n = 7-9/group) were divided in three groups. Aortic arches from the control group were prepared and rings were immediately placed in organ baths, while the aortic arches of IR and IR + DuraGraft rats were preserved in saline or DuraGraft, respectively, for 1 h before being transplanted heterotopically. After 1 h after reperfusion, the grafts were explanted, rings were prepared, and mounted in organ baths. Our results demonstrated that the maximum endothelium-dependent vasorelaxation to acetylcholine was significantly impaired in the IR group compared to the control group, but DuraGraft improved it (control: 89 ± 2%; IR: 24 ± 1%; IR + DuraGraft: 48 ± 1%, p < 0.05). Immunohistochemical analysis revealed decreased intercellular adhesion molecule-1, 4-hydroxy-2-nonenal, caspase-3 and caspase-8 expression, while endothelial cell adhesion molecule-1 immunoreactivity was increased in the IR + DuraGraft grafts compared to the IR-group. DuraGraft mitigates endothelial dysfunction following IR injury in a rat bypass model. Its protective effect may be attributed, at least in part, to its ability to reduce the inflammatory response, oxidative stress, and apoptosis.


Subject(s)
Endothelium, Vascular , Rats, Inbred Lew , Reperfusion Injury , Animals , Rats , Endothelium, Vascular/drug effects , Endothelium, Vascular/metabolism , Reperfusion Injury/metabolism , Male , Coronary Artery Bypass/methods , Coronary Artery Bypass/adverse effects , Oxidative Stress/drug effects , Intercellular Adhesion Molecule-1/metabolism , Disease Models, Animal , Aldehydes/metabolism , Aldehydes/pharmacology , Caspase 3/metabolism , Vasodilation/drug effects , Apoptosis/drug effects , Acetylcholine/pharmacology
4.
Nat Commun ; 15(1): 5737, 2024 Jul 09.
Article in English | MEDLINE | ID: mdl-38982157

ABSTRACT

Exploring the promiscuity of native enzymes presents a promising strategy for expanding their synthetic applications, particularly for catalyzing challenging reactions in non-native contexts. In this study, we explore the promiscuous potential of old yellow enzymes (OYEs) to facilitate the Morita-Baylis-Hillman reaction (MBH reaction), leveraging substrate similarities between MBH reaction and reduction reaction. Using mass spectrometry and spectroscopic techniques, we confirm promiscuity of GkOYE in both MBH and reduction reactions. By blocking H- and H+ transfer pathways, we engineer GkOYE.8, which loses its reduction ability but enhances its MBH activity. The structural basis of MBH reaction catalyzed by GkOYE.8 is obtained through mutation studies and kinetic simulations. Furthermore, enantiocomplementary mutants GkOYE.11 and GkOYE.13 are obtained by directed evolution, exhibiting the ability to accept various aromatic aldehydes and alkenes as substrates. This study demonstrates the potential of leveraging substrate similarities to unlock enzyme functionalities, enabling the catalysis of new-to-nature reactions.


Subject(s)
Biocatalysis , Substrate Specificity , Kinetics , Aldehydes/metabolism , Aldehydes/chemistry , Catalysis , Mutation , Alkenes/metabolism , Alkenes/chemistry , Bacterial Proteins/metabolism , Bacterial Proteins/genetics , Bacterial Proteins/chemistry , Protein Engineering
5.
Int J Mol Sci ; 25(14)2024 Jul 19.
Article in English | MEDLINE | ID: mdl-39063136

ABSTRACT

A method for the reduction of aldehydes with pinacolborane catalyzed by pincer cobalt complexes based on a triazine backbone is developed in this paper. The presented methodology allows for the transformation of several aldehydes bearing a wide range of electron-withdrawing and electron-donating groups under mild conditions. The presented procedure allows for the direct one-step hydrolysis of the obtained intermediates to the corresponding primary alcohols. A plausible reaction mechanism is proposed.


Subject(s)
Alcohols , Aldehydes , Cobalt , Oxidation-Reduction , Cobalt/chemistry , Aldehydes/chemistry , Catalysis , Alcohols/chemistry , Molecular Structure , Boranes/chemistry
6.
Carbohydr Polym ; 342: 122389, 2024 Oct 15.
Article in English | MEDLINE | ID: mdl-39048229

ABSTRACT

The paper reports new hydrogels based on quaternary ammonium salts of chitosan designed as biocidal products. The chitosan derivative was crosslinked with salicylaldehyde via reversible imine bonds and supramolecular self-assemble to give dynamic hydrogels which respond to environmental stimuli. The crosslinking mechanism was demonstrated by 1H NMR and FTIR spectroscopy, and X-ray diffraction and polarized light microscopy. The hydrogel nature, self-healing and thixotropy were proved by rheological investigation and visual observation, and their morphology was assessed by scanning electron microscopy. The relevant properties for application as biocidal products, such as swelling, dissolution, bioadhesiveness, antimicrobial activity and ex-vivo hemocompatibility and in vivo local toxicity and biocompatibility on experimental mice were measured and analyzed in relationship with the imination degree and the influence of each component. It was found that the hydrogels are superabsorbent, have good adhesivity to skin and various surfaces and antimicrobial activity against relevant gram-positive and gram-negative bacteria, while being hemocompatible and biocompatible. Besides, the hydrogels are easily biodegraded in soil. All these properties recommend the studied hydrogels as ecofriendly biocidal agents for living tissues and surfaces, but also open the perspectives of their use as platform for in vivo applications in tissue engineering, wound healing, or drug delivery systems.


Subject(s)
Biocompatible Materials , Chitosan , Hydrogels , Quaternary Ammonium Compounds , Chitosan/chemistry , Chitosan/pharmacology , Hydrogels/chemistry , Hydrogels/pharmacology , Quaternary Ammonium Compounds/chemistry , Quaternary Ammonium Compounds/pharmacology , Animals , Biocompatible Materials/pharmacology , Biocompatible Materials/chemistry , Mice , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/chemical synthesis , Microbial Sensitivity Tests , Disinfectants/pharmacology , Disinfectants/chemistry , Anti-Infective Agents/pharmacology , Anti-Infective Agents/chemistry , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Aldehydes
7.
Sci Rep ; 14(1): 16322, 2024 07 15.
Article in English | MEDLINE | ID: mdl-39009704

ABSTRACT

Age-related macular degeneration (AMD) is one of the leading causes of blindness. AMD is currently incurable; the best solution is to prevent its occurrence. To develop drugs for AMD, it is crucial to have a model system that mimics the symptoms and mechanisms in patients. It is most important to develop safer and more effective anti-AMD drug. In this study, the dose of A2E and the intensity of blue light were evaluated to establish an appropriate atrophic in vitro model of AMD and anti-AMD effect and therapeutic mechanism of Codonopsis lanceolata. The experimental groups included a control group an AMD group treated with A2E and blue light, a lutein group treated with 25 µM lutein after AMD induction, and three groups treated with different doses of C. lanceolata (10, 20, and 50 µg/mL) after AMD induction. Intrinsic apoptotic pathway (Bcl-2 family), anti-oxidative system (Keap1/Nrf2/HO-1 antioxidant response element), and anti-carbonyl effect (4-hydroxynonenal [4-HNE]) were evaluated using immunofluorescence, MTT, TUNEL, FACS, and western blotting analyses. A2E accumulation in the cytoplasm of ARPE-19 cells depending on the dose of A2E. Cell viability of ARPE-19 cells according to the dose of A2E and/or blue light intensity. The population of apoptotic or necrotic cells increased based on the A2E dose and blue light intensity. Codonopsis lanceolata dose-dependently prevented cell death which was induced by A2E and blue light. The antiapoptotic effect of that was caused by activating Keap1/Nrf2/HO-1 pathway, suppressing 4-HNE, and modulating Bcl-2 family proteins like increase of antiapoptotic proteins such as Bcl-2 and Bcl-XL and decrease of proapoptotic protein such as Bim. Based on these findings, 30 µM A2E and 20 mW/cm2 blue light on adult retinal pigment epithelium-19 cells was an appropriate condition for AMD model and C. lanceolata shows promise as an anti-AMD agent.


Subject(s)
Apoptosis , Codonopsis , Macular Degeneration , NF-E2-Related Factor 2 , Oxidative Stress , Codonopsis/chemistry , Humans , Macular Degeneration/drug therapy , Macular Degeneration/metabolism , Macular Degeneration/pathology , Oxidative Stress/drug effects , Apoptosis/drug effects , NF-E2-Related Factor 2/metabolism , Plant Extracts/pharmacology , Antioxidants/pharmacology , Kelch-Like ECH-Associated Protein 1/metabolism , Cell Line , Aldehydes/pharmacology , Retinal Pigment Epithelium/drug effects , Retinal Pigment Epithelium/metabolism , Retinal Pigment Epithelium/pathology , Light/adverse effects , Proto-Oncogene Proteins c-bcl-2/metabolism
8.
Anal Chim Acta ; 1318: 342932, 2024 Aug 22.
Article in English | MEDLINE | ID: mdl-39067919

ABSTRACT

Recently, various biosensors based on odorant-binding proteins (OBPs) were developed for the detection of odorants and pheromones. However, important data gaps exist regarding the sensitive and selective detection of aldehydes with various carbon numbers. In this work, an OBP2a-based electrochemical impedance spectroscopy (EIS) biosensor was developed by immobilizing OBP2a on a gold interdigital electrode, and was characterized by EIS and atomic force microscopy. EIS responses showed the OBP2a-based biosensor was highly sensitive to citronellal, lily aldehyde, octanal, and decanal (detection limit of 10-11 mol/L), and was selective towards aldehydes compared with interfering odorants such as small-molecule alcohols and fatty acids (selectivity coefficients lower than 0.15). Moreover, the OBP2a-based biosensor exhibited high repeatability (relative standard deviation: 1.6%-9.1 %, n = 3 for each odorant), stability (NIC declined by 3.6 % on 6th day), and recovery (91.2%-96.6 % on three real samples). More specifically, the sensitivity of the biosensor to aldehydes was positively correlated to the molecular weight and the heterocyclic molecule structure of the odorants. These results proved the availability and the potential usage of the OBP2a-based EIS biosensor for the rapid and sensitive detection of aldehydes in aspects such as medical diagnostics, food and favor analysis, and environmental monitoring.


Subject(s)
Aldehydes , Biosensing Techniques , Receptors, Odorant , Biosensing Techniques/methods , Aldehydes/chemistry , Aldehydes/analysis , Receptors, Odorant/chemistry , Receptors, Odorant/metabolism , Electrochemical Techniques , Electrodes , Limit of Detection , Odorants/analysis , Gold/chemistry , Dielectric Spectroscopy
9.
J Med Chem ; 67(14): 12439-12458, 2024 Jul 25.
Article in English | MEDLINE | ID: mdl-38996004

ABSTRACT

The discovery of effective and safe antiobesity agents remains a challenging yet promising field. Our previous studies identified Bouchardatine derivatives as potential antiobesity agents. However, the 8a-aldehyde moiety rendered them unsuitable for drug development. In this study, we designed two series of novel derivatives to modify this structural feature. Through a structure-activity relationship study, we elucidated the role of the 8a-aldehyde group in toxicity induction. We identified compound 14d, featuring an 8a-N-acylhydrazone moiety, which exhibited significant lipid-lowering activity and reduced toxicity. Compound 14d shares a similar lipid-lowering mechanism with our lead compound 3, but demonstrates improved pharmacokinetic properties and safety profile. Both oral and injectable administration of 14d significantly reduced body weight gain and ameliorated metabolic syndrome in diet-induced obese mice. Our findings identify 14d as a promising antiobesity agent and highlight the potential of substituting the aldehyde group with an N-acylhydrazone to enhance drug-like properties.


Subject(s)
Aldehydes , Anti-Obesity Agents , Hydrazones , Obesity , Animals , Anti-Obesity Agents/pharmacology , Anti-Obesity Agents/chemical synthesis , Anti-Obesity Agents/pharmacokinetics , Anti-Obesity Agents/therapeutic use , Anti-Obesity Agents/chemistry , Hydrazones/pharmacology , Hydrazones/chemistry , Hydrazones/chemical synthesis , Hydrazones/pharmacokinetics , Hydrazones/therapeutic use , Mice , Structure-Activity Relationship , Aldehydes/chemistry , Male , Obesity/drug therapy , Mice, Inbred C57BL , Diet, High-Fat/adverse effects , Humans , Mice, Obese , Molecular Structure
10.
Food Res Int ; 191: 114651, 2024 Sep.
Article in English | MEDLINE | ID: mdl-39059903

ABSTRACT

To understand the relationship between changes in aroma and bacteria in pigeon breast meat (PBM) during preservation, bacterial communities and volatile compounds in PBM were analyzed using high-throughput sequencing and gas chromatography-ion mobility spectrometry. Analyses of total viable bacteria counts revealed that modified atmospheric packaging (MAP) and electron beam irradiation (EBI) could be used to extend the shelf-life of PBM to 10 d and 15 d, respectively. Furthermore, Lactococcus spp. and Psychrobacter spp. were the dominant bacterial genera of the MAP and EBI groups, respectively. The results of the study revealed 91 volatile organic compounds, one of which, butanal, was the most intense volatile organic compound while being an important source of aroma differences between the physical preservation techniques. Alpha-terpinolene, acetoin-M, gamma-butyrolactone, 1-hexanol-M, and 2,6-dimethyl-4-heptanone may be markers of PBM spoilage. During preservation, the MA group (treatment with 50 % CO2 + 50 % N2) demonstrated greater stabilization of PBM aroma. A Spearman correlation analysis showed that Lactococcus spp., Psychrobacter spp., and Pseudomonas spp. were the dominant bacterial genera of PBM during preservation and were closely related to an increase in the intensity of anisole, 2-methyl-3-furanthiol, and 5-methyl-2-furanmethanol, respectively. Lactococcus spp. and Psychrobacter spp. play crucial roles in the sensory degradation of PBM. In this study, we analyzed the changes in bacterial genera and volatile organic compounds of PBM under different physical preservation techniques to identify a suitable method for preserving PBM and evaluating its freshness.


Subject(s)
Columbidae , Food Microbiology , Psychrobacter , Volatile Organic Compounds , Volatile Organic Compounds/analysis , Animals , Columbidae/microbiology , Psychrobacter/metabolism , Odorants/analysis , Food Preservation/methods , Bacteria/classification , Meat/microbiology , Meat/analysis , Food Packaging/methods , Lactococcus , Gas Chromatography-Mass Spectrometry , Aldehydes/analysis , Microbiota
11.
Food Res Int ; 191: 114716, 2024 Sep.
Article in English | MEDLINE | ID: mdl-39059964

ABSTRACT

Dehydration is an effective method for the long-term storage and aroma retention of gonggan (Citrus sinensis Osb. 'Deqing Gonggan'), which is a Chinese variety of citrus, with unique and characteristic floral, fruity, and citrus flavors. However, the aroma profiles of gonggans prepared using oven- and freeze-drying, the most widely-used drying methods, remain unclear. In this study, a total of 911 volatile organic compounds (VOCs) were detected in dried gonggan. These were primarily composed of alcohols (7.69%), aldehydes (7.03%), esters (15.38%), ketones (7.58%), and terpenoids (23.19%). A total of 67 odorants contributed significantly to the overall aroma of dried gonggans, with the major odor qualities being detected as green, citrus, fruity, floral, and sweet. These were mainly attributed to the presence of aldehydes, esters, and terpenoids. Freeze-drying was more effective in maintaining the unique citrus and mandarin-like aromas attributed to compounds such as limonene, citrial, ß-myrcene, ß-pinene, and γ-terpinene. Moreover, (E,E)-2,4-decadienal had the highest relative odor activity value (rOAV) in freeze-dried gonggans, followed by (E)-2-nonenal, furaneol, (E, E)-2, 4-nonadienal, and E-2-undecenal. Oven-drying promoted the accumulation of terpenes such as octatriene, trans-ß-ocimene, cyclohexanone, copaene, and ɑ-irone, imparting a soft aroma of flowers, fruits, and sweet. Increasing the temperature led to an increase in existing VOCs or the generation of new VOCs through phenylpropanoid, terpenoid, and fatty acid metabolism. The findings of this study offer insights into an optimized procedure for producing high-quality dried gonggans. These insights can be valuable for the fruit-drying industry, particularly for enhancing the quality of dried fruits.


Subject(s)
Freeze Drying , Odorants , Terpenes , Volatile Organic Compounds , Volatile Organic Compounds/analysis , Odorants/analysis , Terpenes/analysis , Fruit/chemistry , Citrus sinensis/chemistry , Desiccation/methods , Aldehydes/analysis , Gas Chromatography-Mass Spectrometry , Ketones/analysis , Bicyclic Monoterpenes/analysis , Esters/analysis , Alkadienes/analysis , Cyclohexenes/analysis , Food Handling/methods , Acyclic Monoterpenes , Cyclohexane Monoterpenes , Alkenes , Sesquiterpenes
12.
Food Res Int ; 191: 114735, 2024 Sep.
Article in English | MEDLINE | ID: mdl-39059967

ABSTRACT

The present study was carried out to investigate the proximate composition, fatty acid (FA) profile and volatile compounds (VC) of cooked green licuri (Syagrus coronata) - an unripe stage that is then cooked - and naturally ripe licuri almonds. The FA profiles were determined by gas chromatography (GC) and the VC composition was evaluated using headspace-solid-phase microextraction coupled with GC-MS. The cooked green licuri presented higher moisture, and lower contents of ashes, proteins and lipids than naturally ripe licuri almonds. The FA profiles of cooked green licuri and naturally ripe licuri almonds showed that saturated FAs were predominant (80%) in both samples, and the concentrations of lauric, palmitic, and oleic acids in naturally ripe licuri almonds were higher than those in cooked green licuri. Limonene was the predominant compound in naturally ripe licuri almonds. The main class of VC in the cooked green licuri were aldehydes, with 3-methyl-butanal and furfural being the main species. Alcohols, such as 3-methyl-butanol and 2-heptanol, were the main class of VC in naturally ripe licuri almonds. Among the volatile compounds, 1-hexanol and 2-nonanone contributed to the aroma of cooked green licuri almonds, whereas 2-heptanone, ethanol, and limonene contributed to the aroma of naturally ripe licuri almonds (almonds not subjected to any cooking process). In a word, cooked green licuri and naturally riped licuri almonds, despite having different proximate compositions, present similar fatty acid profile and distinct aromatic characteristics. Therefore, cooked green licuri and naturally riped licuri almonds are an alternative source of nutrient and could be investigated for the use in the food industry to enhance flavor and aroma to new products.


Subject(s)
Cooking , Fatty Acids , Gas Chromatography-Mass Spectrometry , Volatile Organic Compounds , Volatile Organic Compounds/analysis , Fatty Acids/analysis , Brazil , Solid Phase Microextraction , Cyclohexenes/analysis , Terpenes/analysis , Limonene/analysis , Odorants/analysis , Palmitic Acid/analysis , Oleic Acid/analysis , Aldehydes/analysis , Lauric Acids/analysis , Pentanols/analysis
13.
Biosens Bioelectron ; 261: 116457, 2024 Oct 01.
Article in English | MEDLINE | ID: mdl-38850733

ABSTRACT

Degradation of ionizable lipids in mRNA-based vaccines was recently found to deactivate the payload, demanding rigorous monitoring of impurities in lipid nanoparticle (LNP) formulations. However, parallel screening for lipid degradation in customized delivery systems for next-generation therapeutics maintains a challenging and unsolved problem. Here, we describe a nanopore electrochemical sensor to detect ppb-levels of aldehydes arising from lipid degradation in LNP formulations that can be deployed in massively parallel fashion. Specifically, we combine nanopore electrodes with a block copolymer (BCP) membrane capable of hydrophobic gating of analyte transport between the bulk solution and the nanopore volume. By incorporating aldehyde dehydrogenase (ALDH), enzymatic oxidation of aldehydes generates NADH to enable ultrasensitive voltammetric detection with limits-of-detection (LOD) down to 1.2 ppb. Sensor utility was demonstrated by detecting degradation of N-oxidized SM-102, the ionizable lipid in Moderna's SpikeVax™ vaccine, in mRNA-1273 LNP formulation. This work should be of significant use in the pharmaceutical industry, paving the way for automated on-line quality assessments of next-generation therapeutics.


Subject(s)
Aldehydes , Biosensing Techniques , Electrochemical Techniques , Nanoparticles , Nanopores , Biosensing Techniques/methods , Aldehydes/chemistry , Nanoparticles/chemistry , Electrochemical Techniques/methods , Lipids/chemistry , Limit of Detection , Aldehyde Dehydrogenase/chemistry , Liposomes
14.
Food Res Int ; 190: 114603, 2024 Aug.
Article in English | MEDLINE | ID: mdl-38945572

ABSTRACT

More than 40 volatile compounds were detected in sea cucumber powder during the processing (through freeze-dried, desalination, supercritical fluid extraction and ultra-micro grinding) by multiple methods including e-nose, GC-IMS and GC-MS. It has been determined that aldehydes are the predominant volatile substances in the original freeze-dried sample, accounting for about 30 % of the total volatile substances. In addition, we established a supercritical fluid extraction strategy that could efficiently remove the aldehydes from the sea cucumber powder. GC-IMS and GC-MS showed that the relative content of aldehydes significantly decreased by 14 % and 28 %, respectively. Quantification of aldehydes using GC-MS showed a significant decrease in octanal from 927 µg/kg to 159 µg/kg. Further investigation combined with OAV analysis showed that 17 volatile substances in the freeze-dried sea cucumber powder were considered to be the predominant volatile compounds (OAV > 1).The primary fishy compounds found in sea cucumber powder were identified as hexanal, octanal, and an unidentified compound using GC-O, which can be effectively removed (OAV can't been estimated) by the supercritical fluid extraction strategy we established.


Subject(s)
Chromatography, Supercritical Fluid , Food Handling , Gas Chromatography-Mass Spectrometry , Powders , Sea Cucumbers , Volatile Organic Compounds , Chromatography, Supercritical Fluid/methods , Sea Cucumbers/chemistry , Volatile Organic Compounds/analysis , Volatile Organic Compounds/isolation & purification , Animals , Food Handling/methods , Freeze Drying , Aldehydes/analysis , Aldehydes/isolation & purification , Electronic Nose , Seafood/analysis
15.
Sci Rep ; 14(1): 14568, 2024 06 24.
Article in English | MEDLINE | ID: mdl-38914586

ABSTRACT

COVID-19 has caused a worldwide pandemic, creating an urgent need for early detection methods. Breath analysis has shown great potential as a non-invasive and rapid means for COVID-19 detection. The objective of this study is to detect patients infected with SARS-CoV-2 and even the possibility to screen between different SARS-CoV-2 variants by analysis of carbonyl compounds in breath. Carbonyl compounds in exhaled breath are metabolites related to inflammation and oxidative stress induced by diseases. This study included a cohort of COVID-19 positive and negative subjects confirmed by reverse transcription polymerase chain reaction between March and December 2021. Carbonyl compounds in exhaled breath were captured using a microfabricated silicon microreactor and analyzed by ultra-high-performance liquid chromatography-mass spectrometry (UHPLC-MS). A total of 321 subjects were enrolled in this study. Of these, 141 (85 males, 60.3%) (mean ± SD age: 52 ± 15 years) were COVID-19 (55 during the alpha wave and 86 during the delta wave) positive and 180 (90 males, 50%) (mean ± SD age: 45 ± 15 years) were negative. Panels of a total of 34 ketones and aldehydes in all breath samples were identified for detection of COVID-19 positive patients. Logistic regression models indicated high accuracy/sensitivity/specificity for alpha wave (98.4%/96.4%/100%), for delta wave (88.3%/93.0%/84.6%) and for all COVID-19 positive patients (94.7%/90.1%/98.3%). The results indicate that COVID-19 positive patients can be detected by analysis of carbonyl compounds in exhaled breath. The technology for analysis of carbonyl compounds in exhaled breath has great potential for rapid screening and detection of COVID-19 and for other infectious respiratory diseases in future pandemics.


Subject(s)
Breath Tests , COVID-19 , SARS-CoV-2 , Humans , COVID-19/diagnosis , COVID-19/virology , Breath Tests/methods , Male , Middle Aged , Female , Adult , Aged , SARS-CoV-2/isolation & purification , Exhalation , Aldehydes/analysis , Chromatography, High Pressure Liquid/methods , Mass Spectrometry/methods
16.
Planta Med ; 90(7-08): 554-560, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38843795

ABSTRACT

A selective Oxone-induced oxidation of oleocanthal and oleacein, the two main secoiridoids of olive oil, to their bis-oxidized products is described. This protocol is based on a Baeyer-Villiger mechanism and the concentration of Oxone in the final solution. The bis-oxidation of the aldehydic compounds could be extended for the synthesis of various semisynthetic analogs. The obtained acids exhibit strong antioxidant activity, being efficient free radical scavengers.


Subject(s)
Aldehydes , Olive Oil , Oxidation-Reduction , Aldehydes/chemistry , Olive Oil/chemistry , Antioxidants/chemistry , Antioxidants/pharmacology , Phenols/chemistry , Furans/chemistry , Cyclopentane Monoterpenes/chemistry
17.
Pestic Biochem Physiol ; 202: 105938, 2024 Jun.
Article in English | MEDLINE | ID: mdl-38879329

ABSTRACT

The excessive and indiscriminate use of synthetic insecticides has led to environmental pollution, wildlife destruction, and adverse effects on human health, while simultaneously giving rise to resistance in insect pest populations. This adaptive trait is expressed through various mechanisms, such as changes in the cuticle, heightened activities of detoxifying enzymes, and alterations in the sites of action that reduce their affinity for insecticides. In this context, we associate variation in toxicological response with genomic variation, to identify genetic polymorphisms underlying the different steps of the insect (genotype)-response (phenotype)-insecticide (environment) interaction. Under this framework, our objective was to investigate the genetic factors involved in the toxicological response of D. melanogaster lines when exposed to citronellal and eucalyptol vapors (monoterpenes of plant origin). We quantified KT50 in adult males, representing the time necessary for half of the exposed individuals to be turned upside down (unable to walk or fly). Since the genomes of all lines used are completely sequenced, we perform a Genome Wide Association Study to analyze the genetic underpinnings of the toxicological response. Our investigation enabled the identification of 656 genetic polymorphisms and 316 candidate genes responsible for the overall phenotypic variation. Among these, 162 candidate genes (77.1%) exhibited specificity to citronellal, 45 (21.4%) were specific to eucalyptol, and 3 candidate genes (1.5%) namely CG34345, robo2, and Ac13E, were implicated in the variation for both monoterpenes. These suggest a widespread adaptability in the response to insecticides, encompassing genes influenced by monoterpenes and those orchestrating resistance to the toxicity of these compounds.


Subject(s)
Acyclic Monoterpenes , Drosophila melanogaster , Eucalyptol , Insecticides , Animals , Drosophila melanogaster/drug effects , Drosophila melanogaster/genetics , Eucalyptol/toxicity , Insecticides/toxicity , Male , Acyclic Monoterpenes/toxicity , Genome-Wide Association Study , Monoterpenes/toxicity , Aldehydes/toxicity , Insecticide Resistance/genetics
18.
Food Microbiol ; 122: 104550, 2024 Sep.
Article in English | MEDLINE | ID: mdl-38839218

ABSTRACT

Listeria monocytogenes presents significant risk to human health due to its high resistance and capacity to form toxin-producing biofilms that contaminate food. The objective of this study was to assess the inhibitory effect of citronella aldehyde (CIT) on L. monocytogenes and investigate the underlying mechanism of inhibition. The results indicated that the minimum inhibitory concentration (MIC) and Minimum sterilisation concentration (MBC) of CIT against L. monocytogenes was 2 µL/mL. At this concentration, CIT was able to effectively suppress biofilm formation and reduce metabolic activity. Crystalline violet staining and MTT reaction demonstrated that CIT was able to inhibit biofilm formation and reduce bacterial cell activity. Furthermore, the motility assessment assay revealed that CIT inhibited bacterial swarming and swimming. Scanning electron microscopy (SEM) and laser confocal microscopy (LSCM) observations revealed that CIT had a significant detrimental effect on L. monocytogenes cell structure and biofilm integrity. LSCM also observed that nucleic acids of L. monocytogenes were damaged in the CIT-treated group, along with an increase in bacterial extracellular nucleic acid leakage. The proteomic results also confirmed the ability of CIT to affect the expression of proteins related to processes including metabolism, DNA replication and repair, transcription and biofilm formation in L. monocytogenes. Consistent with the proteomics results are ATPase activity and ATP content of L. monocytogenes were significantly reduced following treatment with various concentrations of CIT. Notably, CIT showed good inhibitory activity against L. monocytogenes on cheese via fumigation at 4 °C.This study establishes a foundation for the potential application of CIT in food safety control.


Subject(s)
Biofilms , Cheese , Listeria monocytogenes , Microbial Sensitivity Tests , Listeria monocytogenes/drug effects , Listeria monocytogenes/growth & development , Listeria monocytogenes/physiology , Cheese/microbiology , Biofilms/drug effects , Biofilms/growth & development , Anti-Bacterial Agents/pharmacology , Food Preservation/methods , Food Microbiology , Bacterial Proteins/metabolism , Bacterial Proteins/genetics , Aldehydes/pharmacology , Plant Extracts/pharmacology , Acyclic Monoterpenes/pharmacology
19.
Food Res Int ; 188: 114506, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38823846

ABSTRACT

The characteristic aroma compounds of braised pork were identified through molecular sensory science and PLSR analysis, and the difference between two cooking methods, traditional open-fire (BPF) and induction cooker (BPC), was compared. Seventeen aroma compounds with odor activity values (OAVs) > 1 were identified in both samples. BPF revealed higher OAVs for most of the aroma compounds compared to BPC, and the higher aroma quality. Aroma recombination and omission experiments confirmed that twelve aroma compounds significantly contributed to the characteristic aroma of braised pork, and eight compounds such as hexanal, (E)-2-octenal, and methanethiol were further confirmed as important contributors by PLSR analysis. Furthermore, PLSR analysis clarified the role of aldehydes such as hexanal, (E)-2-octenal, and (E,E)-2,4-decadienal in contributing to fatty attribute, whereas methanethiol was responsible for the meaty aroma. These characteristic aroma compounds mainly derived from lean meat due to its high content of phospholipids, and the exogenous seasonings contributed to the balanced characteristic aroma profile of braised pork by altering the distribution of these characteristic aroma compounds. Variations in heating parameters affected the formation of lipid oxidation and Strecker degradation products, which might explain aroma discrepancy between braised pork cooked by two methods with different heat transfer efficiencies.


Subject(s)
Aldehydes , Cooking , Odorants , Cooking/methods , Odorants/analysis , Animals , Swine , Aldehydes/analysis , Volatile Organic Compounds/analysis , Pork Meat/analysis , Humans , Sulfhydryl Compounds/analysis
20.
Int J Mol Sci ; 25(12)2024 Jun 20.
Article in English | MEDLINE | ID: mdl-38928488

ABSTRACT

The oxidative esterification of aldehydes under mild conditions remains a significant challenge. This study introduces a unique defective UiO-66 to achieve gold nanoclusters (AuNCs) for efficient aldehyde oxidation under mild conditions. The construction and characterization of these materials are thoroughly investigated by techniques of XRD, SEM and TEM images, FT-IR, Raman, and XPS spectrum, emphasizing the unique microporous in defective UiO-66 are conducive to the fabrication of AuNCs. The catalytic performance of the prepared materials in aldehyde oxidation reactions is systematically evaluated, demonstrating the remarkable efficiency of dispersed Au@UiO-66-25 with high-content (9.09 wt%) Au-loading and ultra-small size (~2.7 nm). Moreover, mechanistic insights into the catalytic process under mild conditions (70 °C for 1 h) are provided, elucidating the determination of defective UiO-66 in the confined fabrication of AuNCs and subsequent furfural adsorption, which underlie the principles governing the observed enhancements. This study establishes the groundwork for the synthesis of highly dispersed and catalytically active metal nanoparticles using defective MOFs as a platform, advancing the catalytic esterification reaction of furfural to the next level.


Subject(s)
Aldehydes , Gold , Metal Nanoparticles , Oxidation-Reduction , Gold/chemistry , Metal Nanoparticles/chemistry , Aldehydes/chemistry , Catalysis , Metal-Organic Frameworks/chemistry , Porosity , Esterification , Spectroscopy, Fourier Transform Infrared
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