Nonanoic Acid Research Articles

Stability Mechanism of Menthol and Fatty Acid Based Hydrophobic Eutectic Solvents: Insights from Nonbonded Interactions

Deep eutectic solvents (DESs), being ionic liquid (IL) analogues, are easy to prepare, cost-effective, recyclable, and biocompatible and have low toxicity. Hydrophobic deep eutectic solvents (HDESs) composed of natural compounds are highly effective in the extraction of micropollutants (metal ions, pharmaceuticals, and so on) from an aqueous stream. In this work, the formation mechanism of dl-menthol and carboxylic acid (acetic, butanoic, hexanoic, octanoic, nonanoic, decanoic, and dodecanoic acid) based DESs in a molar ratio of 1:1 has been presented along with their structural composition, charge transfer analysis, chemical stability, and aqueous phase solvation analysis using density functional theory (DFT) calculations. The intermolecular hydrogen bonding and dispersion interactions between menthol (−OH group) and carboxylic acids (−COOH) at a short to medium range are responsible for the stable DES formation. CHELPG and natural bonding orbital (NBO) analyses suggest that the acetic acid based DES is more closely structured and has lesser resistance to charge transfer as compared to higher chain length acid (C8 to C12) based DESs. Frontier molecular orbital (FMO) analysis confirms higher chemical stability and lesser reactivity of long-chain fatty acid based DESs as compared to their short-chain counterparts. The atom-in-molecules (AIM) and noncovalent interaction (NCI) analyses suggest that a strong network of hydrogen bonding and dispersion interactions are solely responsible for the formation and strength of the DESs. The DFT-based solvation study supported by spatial distribution function (SDF) from molecular dynamics (MD) indicates that the lower fatty acid (C1 to C6) based DESs are disrupted by water penetration to a higher extent as compared to the higher fatty acid (C8 to C12) based DESs. According to the solvation-based NCI analysis, van der Waals and dispersion connections are the interactions that are largely responsible for the chemical and physical stability of the DESs in the aqueous phase. The overall findings from the computational study have a remarkable degree of coherence with the findings of the experiments that were previously reported.

Effects of High-Canolol Phenolic Extracts on Fragrant Rapeseed Oil Quality and Flavor Compounds during Frying

Fragrant rapeseed oil (FRO) is a frying oil widely loved by consumers, but its quality deteriorates with increasing frying time. In this study, the effect of high-canolol phenolic extracts (HCP) on the physicochemical properties and flavor of FRO during frying was investigated. During frying, HCP significantly inhibited the increase in peroxide, acid, p-anisidine, and carbonyl values, as well as total polar compounds and degradation of unsaturated fatty acids. A total of 16 volatile flavor compounds that significantly contributed to the overall flavor of FRO were identified. HCP was effective in reducing the generation of off-flavors (hexanoic acid, nonanoic acid, etc.) and increased the level of pleasant deep-fried flavors (such as (E,E)-2,4-decadienal). Therefore, the application of HCP has a positive effect on protecting the quality and prolonging the usability of FRO.

NMR-Based Metabolomics: A New Paradigm to Unravel Defense-Related Metabolites in Insect-Resistant Cotton Variety through Different Multivariate Data Analysis Approaches.

Cotton (Gossypium hirsutum) is an economically important crop and is widely cultivated around the globe. However, the major problem of cotton is its high vulnerability to biotic and abiotic stresses. It has been around three decades since the cotton plant was genetically engineered with genes encoding insecticidal proteins (mainly Cry proteins) with an aim to protect it against insect attack. Several studies have been reported on the impact of these genes on cotton production and fiber quality. However, the metabolites responsible for conferring resistance in genetically modified cotton need to be explored. The current work aims to unveil the key metabolites responsible for insect resistance in Bt cotton and also compare the conventional multivariate analysis methods with deep learning approaches to perform clustering analysis. We aim to unveil the marker compounds which are responsible for inducing insect resistance in cotton plants. For this purpose, we employed 1H-NMR spectroscopy to perform metabolite profiling of Bt and non-Bt cotton varieties, and a total of 42 different metabolites were identified in cotton plants. In cluster analysis, deep learning approaches (linear discriminant analysis (LDA) and neural networks) showed better separation among cotton varieties compared to conventional methods (principal component analysis (PCA) and orthogonal partial least square discriminant analysis (OPLSDA)). The key metabolites responsible for inter-class separation were terpinolene, α-ketoglutaric acid, aspartic acid, stigmasterol, fructose, maltose, arabinose, xylulose, cinnamic acid, malic acid, valine, nonanoic acid, citrulline, and shikimic acid. The metabolites which regulated differently with the level of significance p < 0.001 amongst different cotton varieties belonged to the tricarboxylic acid cycle (TCA), Shikimic acid, and phenylpropanoid pathways. Our analyses underscore a biosignature of metabolites that might involve in inducing insect resistance in Bt cotton. Moreover, novel evidence from our study could be used in the metabolic engineering of these biological pathways to improve the resilience of Bt cotton against insect/pest attacks. Lastly, our findings are also in complete support of employing deep machine learning algorithms as a useful tool in metabolomics studies.

Adverse effects, studied on ants, of six products largely used by humans; a mini review

Working on ants as models, we examined the side effects of six largely used products, separately published our findings, and here summarize them for the readers’ convenience. The herbicides, the active substance of which is pelargonic acid, must be used only for not cultivated area since they impact the live of the soil fauna. Imodium, the active substance of which is Loperamide, used to stop diarrhea, should be used during short time periods, monitoring the patients as for their food consumption, locomotion, social relationships, cognition and dependence on the drug use. Only small amount of the myorelaxant Epsipram, the active substance of which is Tetrazepam, should be used, monitoring the patients as for their activity, locomotion, social relationships, stress, cognition, memory and dependence on the drug consumption. The antiemetic Motilium, the active substance of which is Domperidone, should be used after having made an adequate clinical examination of the patients, take then care of them monitoring them as for their health since side effects may occur. The dietary supplement Cognizing, the active substance of which is citicoline, should not be used, being inefficient and causing stress, agitation, nervousness and strong dependence on its consumption. The dietary supplement PQQ is efficient and has no adverse effect; it could be used, but at low doses, since, being novel, some not yet observed side effects may occur.

Antidiabetic Potentials of Ethanol Extract of Timonius flavescens (Jacq.) Baker Leaf

Diabetes Mellitus (DM) is a chronic disease caused by heredity or deficiency in insulin secretion. This disease has occupied the second position as an epidemic in Indonesia. The World Health Organization (WHO) states that nearly 70% of diabetic patients use plants as the main source of antidiabetic agents. One of the plants used by the community for a long time to lower blood sugar is Timonius flavescens (family Rubiaceae). This study aims to determine the content of antidiabetic active compounds in the ethanol extract of T. flavescens leaves by using massspectrometry gas chromatography (GC-MS). The results of GC-MS showed that there were more than 40 compounds, then 10 of them had the highest value detected as having antidiabetic agent properties. These compounds include (3β)- stigmast-5-en-3-ol, 3β.-(acetyloxy)-15.-hydroxy- 5..-cholesta-8(14),9(11)-dien-7-one, alpha-tocopherol, hexade-canoic acid, nonanoic acid, phytol, 2,3-dihydrobenzofuran, heptanoic acid, neophytadiene, and campesterol which have been shown to have antidiabetic properties. The results of this study are expected to provide criticalinformation for researchers and the public regarding the use of T. flavescens leaves as medicine.

Analysis of Hazelnuts (Corylus avellana L.) Stored for Extended Periods by 1H NMR Spectroscopy Monitoring Storage-Induced Changes in the Polar and Nonpolar Metabolome

Storage is a critical step in the post-harvest processing of hazelnuts, as it can lead to mold, rancidity, and off-flavor. However, there is a lack of analytical methods to detect improper or extended storage. To comprehensively investigate the effects of hazelnut storage, samples were stored under five different conditions for up to 18 months. Subsequently, the polar and nonpolar metabolome were analyzed by 1H NMR spectroscopy and chemometric approaches for classification as well as variable selection. Increases in hexanoic, octanoic, and nonanoic acid, all products of lipid oxidation and responsible for quality defects, were found across all conditions. Furthermore, the concentration of free long-chain fatty acids increased in samples stored at high temperatures. Harsh short-term storage resulted in an increase in fumaric and lactic acid, glucose, fructose, and choline and a decrease in acetic acid.

Estimating the Reduction in Cover Crop Vitality Followed by Pelargonic Acid Application Using Drone Imagery

Cultivation of cover crops is a valuable practice in sustainable agriculture. In cover crop management, the method of desiccation is an important consideration, and one widely used method for this is the application of glyphosate. With use of glyphosate likely to be banned soon in Europe, the purpose of this study was to evaluate the herbicidal effect of pelargonic acid (PA) as a bio-based substitute for glyphosate. This study presents the results of a two-year field experiment (2019 and 2021) conducted in northeast Germany. The experimental setup included an untreated control, three different dosages (16, 8, and 5 L/ha) of PA, and the active ingredients glyphosate and pyraflufen. A completely randomised block design was established. The effect of the herbicide treatments was assessed by a visual estimate of the percentage of crop vitality and a comparison assessment provided by an Ebee+ drone. Four vegetation indices (VIs) calculated from the drone images were used to verify the credibility of colour (RGB)-based and near-infrared (NIR)-based vegetation indices. The results of both types of assessment indicated that pelargonic acid was reasonably effective in controlling cover crops within a week of application. In both experimental years, the PA (16 L/ha) and PA_2T (double application of 8 L/ha) treatments demonstrated their highest herbicidal effect for up to seven days after application. PA (16 L/ha) vitality loss decreased over time, while PA_2T (double application of 8 L/ha) continued to exhibit an almost constant effect for longer due to the second application one week later. The PA dosage of 5 L/ha, pyraflufen, and a mixture of the two exhibited a smaller vitality loss than the other treatments. However, except for glyphosate, the herbicidal effect of all the other treatments decreased over time. At the end of the experiment, the glyphosate treatment (3 L/ha) demonstrated the lowest estimated vitality. The results of the drone assessments indicated that vegetation indices (VIs) can provide detailed information regarding crop vitality following herbicide application and that RGB-based indices, such as EXG, have the potential to be applied efficiently and cost-effectively utilising drone imagery. The results of this study demonstrate that pelargonic acid has considerable potential for use as an additional tool in integrated crop management.

Monitorization of Varietal Aroma Composition Dynamics during Ripening in Intact Vitis vinifera L. Tempranillo Blanco Berries by Hyperspectral Imaging.

The measurement of aromatic maturity during grape ripening provides very important information for determining the harvest date, particularly in white cultivars. However, there are currently no tools that allow this measurement to be carried out in a noninvasive and rapid way. For this reason, in the present work, we have studied the use of hyperspectral imaging (HSI)) to estimate the aromatic composition of Vitis vinifera L. Tempranillo Blanco berries during ripening. A total of 236 spectra in the VIS+short wave near-infrared (VIS+SW-NIR) range (400-1000 nm) of intact berries were acquired contactless under laboratory conditions. As gold standard values, a total of 20 volatile compounds were quantified by gas chromatography-mass spectrometry (GC-MS), and the concentration of total soluble solids (TSS) was measured by refractometry. Calibration, cross-validation, and prediction models were built using partial least squares (PLS). Values of RCV2 ≥ 0.70 were obtained for α-terpineol, p-cymene, β-damascenone, β-ionone, benzaldehyde, benzyl alcohol, hexanal, citral, linalool, 2-phenylethanol, octanoic acid, nonanoic acid, 2-hexenal, 2-hexen-1-ol, (Z)-3-hexen-1-ol, total C13 norisoprenoids, total C6 compounds, total positive compounds (i.e., the sum of all families except C6 compounds), total benzenoids, and total soluble solids (TSS). Therefore, it can be affirmed that HSI in the VIS + SW-NIR range could be a good tool to estimate the aromatic composition of Tempranillo Blanco grape berries in a contactless, fast, and nondestructive way.

The Effects of Processing Time and Temperature on the Characteristics of Candlenut Oil using the Rendering Process Method

Hazelnut (Aleurits moluccana), contains nutrients and non-nutrition. Non-nutritional substances in hazelnut, for example, saponins, falvonoids, and polyphenols. In this research, the hot extraction process was carried out for candlenut raw materials, as well as product analysis for candlenut oil. The purpose of this study was to process hazelnut seeds into hazelnut oil using the rendering process method and to determine the effect of the process on the composition of the chemical compounds contained in hazelnut oil. The process parameters used were temperature and extraction process time of 65 ℃, 70 ℃ and 75 ℃ with various extraction times of 75, 100, 125 and 150 minutes. The results showed that the yield of hazelnut oil using the rendering method obtained a yield of 23.57% at an extraction time of 150 minutes and a temperature of 75℃ with a density of 0.9241 gr/ml. Analysis using Gas Chromatography Mass Spectrometry (GC-MS) in the rendering process there are five main components Margaric acid methyl ester at 8.98%, Linoleic Acid, 32.66% , Linolenic 22.31% Oleic at 33.39%. acid, Nonanoic acid of 2.66 %

Cellular responses to 8-methyl nonanoic acid, a degradation by-product of dihydrocapsaicin, in 3T3-L1 adipocytes

BackgroundCapsaicinoids, such as dihydrocapsaicin (DHC), exert the health-promoting effects of chili peppers on energy metabolism. The metabolic responses to capsaicinoids are primarily mediated through transient receptor potential cation channel subfamily V member 1 (TRPV1). However, the varying contributions of their metabolites to beneficial health outcomes remain unclear. 8-methyl nonanoic acid (8-MNA), a methyl-branched medium chain fatty acid (MCFA), is an in vivo degradation by-product of DHC. Since MCFAs have emerged as metabolic modulators in adipocytes, here we examined various cellular responses to 8-MNA in 3T3-L1 adipocytes.MethodsThe viability of 3T3-L1 adipocytes exposed to various concentrations of 8-MNA was assessed by the Calcein AM assay. Biochemical assays for lipid accumulation, AMP-activated protein kinase (AMPK) activity, lipolysis and glucose uptake were performed in 3T3-L1 adipocytes treated with 8-MNA during 48-h nutrient starvation or 5-day maturation.Results8-MNA caused no impact on cell viability. During nutrient starvation, 8-MNA decreased lipid amounts in association with AMPK activation, a molecular event that suppresses lipogenic processes. Moreover, 3T3-L1 adipocytes that were treated with 8-MNA during 5-day maturation exhibited a reduced lipolytic response to isoproterenol and an increased glucose uptake when stimulated with insulin.ConclusionsThese results suggest that 8-MNA derived from DHC modulates energy metabolism in adipocytes and also support the idea that the metabolic benefits of chili consumption are partly attributable to 8-MNA.

Recombinant yeast for production of the pain receptor modulator nonivamide from vanillin

We report on the development of a method based on recombinant yeast Saccharomyces cerevisiae to produce nonivamide, a capsaicinoid and potent agonist of the pain receptor TRPV1. Nonivamide was produced in a two-step batch process where yeast was i) grown aerobically on glucose and ii) used to produce nonivamide from vanillin and non-anoic acid by bioconversion. The yeast was engineered to express multiple copies of an amine transaminase from Chromobacterium violaceum (CvTA), along with an NADH-dependent alanine dehydrogenase from Bacillus subtilis (BsAlaDH) to enable efficient reductive amination of vanillin. Oxygen-limited conditions and the use of ethanol as a co-substrate to regenerate NADH were identified to favour amination over the formation of the by-products vanillic alcohol and vanillic acid. The native alcohol dehydrogenase ADH6 was deleted to further reduce the formation of vanillic alcohol. A two-enzyme system consisting of an N-acyltransferase from Capsicum annuum (CaAT), and a CoA ligase from Sphingomonas sp. Ibu-2 (IpfF) was co-expressed to produce the amide. This study provides proof of concept for yeast-based production of non-ivamide by combined transamination and amidation of vanillin.

Biodegradation of oil-contaminated aqueous ecosystem using an immobilized fungi biomass and kinetic study

Remediation of environmental oil pollution with the usage of fungal organisms has proven to be a successful cleanup bioremediation method for organic contaminants. To investigate the breakdown of oil pollutants in water environments, biosurfactant-producing fungi have been isolated from oil-polluted soil samples. 16s rRNA sequencing technique was performed to identify the fungal organism and phylogenetic tree has been constructed. A variety of biosurfactant screening tests have demonstrated the better biosurfactant producing ability of fungi. The emulsion's stability, which is essential for the biodegradation process, was indicated by the emulsification index of 68.48% and emulsification activity of 1.3. In the isolated biosurfactant, important functional groups such as amino groups, lipids, and sugars were found according to thin layer chromatography analysis with a maximum retention value of 0.85. A maximum oil degradation of around 64% was observed with immobilized beads within 12 days. The half-life, and degradation removal rate constant of 20.21 days and 0.03 day−1, respectively, have been determined by the degradation kinetic analysis. GCMS analysis confirmed the highly degraded hydrocarbons such as nonanoic acid and pyrrolidine. The immobilized fungi exhibit better oil biodegradability in aqueous solutions.

A new sample treatment strategy based on supramolecular solvent for determination of herbicide residues in water samples by Box-Behnken design

This paper describes a sensitive, simple and green analytical method for pretreatment of sulfonylurea and pyrethroid herbicides in water samples by supramolecular solvent-based liquid phase microextraction (SUPRAS-LPME). The SUPRAS was rapidly formed by nonanoic acid and tetrahydrofuran (THF)/water solution. The attractive features of SUPRAS-LPME include the simplicity, high enrichment factor, low cost and less consumption of organic solvents. The main influencing factors including type and volume of fatty acids, volume of THF, ionic strength, vortex time and volume of formic acid were optimized in detail, and then the significant variables were optimized by Box-Behnken design (BBD). Under the optimized condition, the proposed method shows high precision (RSDs < 13.7 %), low limits of detection (0.5–10 μg L-1) and limits of quantitation (10–45 μg L-1), acceptable recovery (71.3 %-95.9 %). The proposed method was successfully applied for analysis of sulfonylurea and pyrethroid herbicides in water samples, making it an alternative analytical strategy for determination of trace analytes at the microgram per liter range with desirable sensitivity.

Spatial analysis of the risk for canine visceral leishmaniasis in an urban area in the State of Sergipe.

Visceral Leishmaniasis is included among the neglected tropical diseases, being directly related to conditions of social vulnerability, in urban environments, dogs act as important reservoirs. The aim of the study was to evaluate the distribution of dogs, related risk factors and identify of volatile organic compounds from infected dogs. Peripheral blood samples from 72 dogs were collected for detection using the ELISA test, in addition to hair samples for analysis by GC-MS. Of the evaluated dogs, 13 (18.05%/72) were reactive for canine VL, seven in Aracaju and six in Propriá. Factors related to vegetation, age, place where the dog stays and free access to the street, were associated with a greater chance of the dog becoming infected. Fifty-three compounds were identified from ten canine hair samples, among which 2-butoxyethanol, benzaldehyde, decane, 2-phenylacetaldehyde, nonan-1-ol, 2-phenoxyethanol, nonanoic acid, 8-heptadecene and eicosane were found in seropositive dogs for leishmaniasis. The guardian's posture has been increasingly important, requiring more attention to the dog's health and actions aimed at environmental management in an attempt to reduce cases of canine VL in the state. Even though the identified VOCs have not been associated with leishmanial infection, it is of great use for understanding canine hair substances.

Kinetic versus thermodynamic polymorph stabilization of a tri-carboxylic acid derivative at the solid-liquid interface.

The carboxylic acid moiety gives rise to structural variability in surface-supported self-assembly due to the common expression of various H-bonding motifs. Self-assembly of 3-fold symmetric tricarboxylic acid derivatives on surfaces typically results in monolayer structures that feature the common 2-fold cyclic R22(8) H-bond motif for at least one of the carboxylic acid groups. Polymorphs that are exclusively based on 3-fold cyclic R33(12) H-bonds were predicted but remained elusive. Here, we show the emergence of such a superflower (SF) structure purely based on R33(12) H-bonds for L-benzene-1,3,5-tricarbonyl phenylalanine (L-BTA), a molecule derived from the well-studied trimesic acid (TMA). In contrast to TMA, L-BTA is not completely planar and is also equipped with additional functional groups for the formation of secondary intermolecular bonds. At the heptanoic acid-graphite interface we transiently observe a SF structure, which is dynamically converted into a chicken-wire structure that only exhibits R22(8) H-bonds. Interestingly, when using nonanoic acid as a solvent the initially formed SF structure remained stable. This unexpected behaviour is rationalized by accompanying force field simulations and experimental determination of solvent-dependent L-BTA solubility.

Lactobacillus paracasei ET-22 and derived postbiotics reduce halitosis and modulate oral microbiome dysregulation - a randomized, double-blind placebo-controlled clinical trial.

Oral microbial dysbiosis is the primary etiologic factor for halitosis and may be the critical preventive target for halitosis. This study included randomized controlled trials (RCTs) assessing the effects of Lactobacillus paracasei ET-22 live and heat-killed bacteria on halitosis and the related oral microbiome. 68 halitosis subjects were divided into placebo, ET-22 live (ET-22.L) and ET-22 heat-killed (ET-22.HK) groups. Subjects took different lozenges three times a day for 4 weeks and underwent saliva collection and assessment of breath volatile sulfur compound (VSC) levels at the beginning and end of the intervention. Salivary volatile organic compounds were measured using HS-SPME-GC/MS, and the microbiome profile was determined by 16S rRNA gene amplicon sequencing. A positive decrease in breath volatile sulfur compound (VSC) levels was observed in the means of both ET-22.L and ET-22.HK groups after 4 weeks of intervention, being more marked in the ET-22.L group (p = 0.0148). Moreover, ET-22.L and ET-22.HK intervention remarkably changed the composition of total salivary volatile organic compounds (VOCs) and aroma-active VOCs. Key undesirable VOCs, such as indole, pyridine, nonanoic acid, benzothiazole, and valeric acid, were significantly reduced. Meanwhile, ET-22.L or ET-22.HK also altered the taxonomic composition of the salivary microbiome. The halitosis pathogens Rothia and Streptococcus were significantly reduced in the ET-22.HK group and the pathogenic Solobacterium and Peptostreptococcus were significantly inhibited in the ET-22.L group. Collectively, our study suggests that both ET-22.L and ET-22.HK can significantly inhibit the production of undesirable odor compounds in subjects with halitosis, which may be related to the changes of the oral microbiome.

One-step effervescence tablet-assisted switchable hydrophilic solvent microextraction combined with micro spectrophotometry for the determination of copper in Salvia yunnanensis and environmental samples

In this work, an efficient one-step effervescence tablet-assisted switchable hydrophilic solvent microextraction (ETA-SHS-ME) method was developed and firstly combined with micro ultraviolet-visible (micro UV-Vis) spectrophotometry for the determination of trace copper (Cu) in natural medicine Salvia yunnanensis and environmental samples (water and soil). The extraction was rapidly accomplished in one step by transferring the effervescence tablet into the aqueous sample, the proton donor agent (malonic acid) contained in the tablet reacted simultaneously with the organic phase source (sodium nonanoate) and the effervescent agent (sodium bicarbonate, NaHCO3) to produce the extractant nonanoic acid and CO2. The in situ generated CO2 promoted the dispersion of nonanoic acid in the aqueous sample and improved the extraction efficiency of the analytical method. Under the optimal conditions, the limit of detection (LOD) and the limit of quantification (LOQ) were 0.01 and 0.04 μg/L, respectively, and the enhancement factor (EF) was 76.3. The developed method was successfully applied to the analysis of trace Cu in natural medicine and environmental samples. The one-step extraction method coupled with portable spectrophotometer has a good prospect for application in field analysis.

Stereoselective Synthesis of γ‐(Acyloxy)carboxylic Acids and γ‐Lactones Featuring the Switch of Stereopreference of Candida antarctica Lipase B in Sodium γ‐Hydroxycarboxylate Homologues

AbstractScalable protocols of straightforward synthesis of enantiomeric γ‐(acyloxy)carboxylic acids and γ‐lactones are presented. The key step is lipase‐catalyzed stereoselective acylation of γ‐hydroxycarboxylic acid sodium salt in organic solvent followed by acidification of the product, extraction and acidic relactonization of the unreacted enantiomer. The mixture of γ‐(acyloxy)carboxylic acid and γ‐lactone is separated either by extraction with solution of sodium bicarbonate or by distillation. A switch of enantioinduction of Candida antarctica lipase B along homologous nucleophiles from R configuration of γ‐hydroxyhexanoic acid salt to S configuration of the C7 and longer‐chain homologues has been disclosed. Both enantiomers of γ‐(acyloxy)pentanoic acids; γ‐(acetyloxy)octanoic and ‐nonanoic acids with S configuration; [(1S,5R)‐5‐(chloroacetyloxy)cyclopent‐2‐en‐1‐yl]acetic acid and enantiomeric γ‐lactones derived from them were prepared with e. r. &gt;98.5/1.5. The rates of acylation of C5 to C9 homologous salts differ by three orders of magnitude but remain applicable for preparative synthesis by variation of the enzyme loading and reaction time.

Medium-Chain-Length Fatty Acid Catabolism in Cupriavidus necator H16: Transcriptome Sequencing Reveals Differences from Long-Chain-Length Fatty Acid β-Oxidation and Involvement of Several Homologous Genes.

The number of genes encoding β-oxidation enzymes in Cupriavidus necator H16 (synonym, Ralstonia eutropha H16) is high, but only the operons A0459-A0464 and A1526-A1531, each encoding four genes for β-oxidation enzymes, were expressed during growth with long-chain-length fatty acids (LCFAs). However, we observed that C. necator ΔA0459-A0464 ΔA1526-A1531 and C. necator H16 showed the same growth behavior during growth with decanoic acid and shorter FAs. The negative effect of the deletion of these two operons increased with an increasing chain length of the utilized FAs. Transcriptome sequencing (RNA-Seq) revealed the expression profiles of genes involved in the catabolism of medium-chain-length fatty acids (MCFAs) in C. necator H16. Operon A0459-A0464 was expressed only during growth with nonanoic acid, whereas operon A1526-A1531 was highly expressed during growth with octanoic and nonanoic acid. The gene clusters B1187-B1192 and B0751-B0759 showed a log2 fold change in expression of up to 4.29 and 4.02, respectively, during growth with octanoic acid and up to 8.82 and 5.50, respectively, with nonanoic acid compared to sodium gluconate-grown cells. Several acyl-CoA ligases catalyze the activation of MCFAs with coenzyme A (CoA), but fadD3 (A3288), involved in activation of LCFAs, was not detected. The expression profiles of C. necator strain ΔA0459-A0464 ΔA1526-A1531 showed that the growth with nonanoic acid resulted in the expression of further β-oxidation enzyme-encoding genes. Additional insights into the transport of FAs in C. necator H16 revealed the complexity and putative involvement of the DegV-like protein encoded by A0463 in the transport of odd-chain-length FAs and of siderophore biosynthesis in the transport mechanism. IMPORTANCE Although Cupriavidus necator H16 has been used in several studies to produce polyhydroxyalkanoates from various lipids, the fatty acid metabolism is poorly understood. The β-oxidation of long-chain-length FAs has been investigated, but the tremendous number of homologous genes encoding β-oxidation enzymes hides the potential for variances in the expressed genes for catabolism of shorter FAs. The catabolism of medium-chain-length FAs and connected pathways has not been investigated yet. As more sustainable substrates such as lipids and the production of fatty acids and fatty acid derivates become more critical with the dependency on fossil-based substances, understanding the complex metabolism in this highly diverse workhorse for biotechnology, C. necator, is inevitable. For further metabolic engineering and construction of production strains, we investigated the metabolism during growth on medium-chain-length FAs by RNA-Seq.

The capsaicinoid nonivamide suppresses the inflammatory response and attenuates the progression of steatosis in a NAFLD-rat model.

Nonalcoholic fatty liver disease (NAFLD) is relatively associated with comorbidities in obesity and metabolic inflammation. Low-grade inflammation following the high-fat diet (HFD)-induced NAFLD can promote the development of nonalcoholic steatohepatitis (NASH) through particularly liver-resident immune cell recruitment and hepatic nuclear factor kappa B (NF-κB) pathway. Therefore, inflammatory intervention may contribute to NASH reduction. Pelargonic acid vanillylamide (PAVA) or nonivamide is one of the pungent capsaicinoids of Capsicum species and has been found in chili peppers. Our previous study demonstrated that PAVA improved hepatic function, decreased oxidative stress and reduced apoptotic cell death but the insight role of PAVA on NAFLD is still unclear. Thus, this study aimed to investigate the underlying anti-inflammatory mechanism of PAVA in an NAFLD-rat model. Male Sprague Dawley rats were fed with normal diet or HFD for 16 weeks. Then high-fat rats were given vehicle or PAVA (1 mg/kg/day) for another 4 weeks. We found that PAVA alleviated hepatic inflammation associated with the reducing toll-like receptor 4/NF-κB pathway, showing significantly lower recruitment of cluster of differentiation 44. PAVA also maintained activity of insulin signaling pathway, and attenuated NOD-, LRR- and pyrin domain-containing protein 3 (NLRP3) inflammasome formation. NAFLD progresses to NASH through transforming growth factor (TGF-β1), and also recovery to simple stage followed by PAVA suppresses pro-inflammatory cytokines such as tumor necrosis factor-α, interleukin-1β, interleukin-6, and Janus kinase 2 (JAK2)/signal transducer and activator of transcription 3 (STAT3) pathway. Therefore, our findings suggest that PAVA provides a novel therapeutic approach for NAFLD and slows the progression to NASH.