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Molecules (Basel, Switzerland) Nov 2023Camphene, C12-C18 fatty acids, and titanium sulfate were used as raw materials to study the synthesis of long-chain fatty acid isobornyl esters. Products were analyzed...
Camphene, C12-C18 fatty acids, and titanium sulfate were used as raw materials to study the synthesis of long-chain fatty acid isobornyl esters. Products were analyzed quantitatively by gas chromatography (GC), characterized by nuclear magnetic resonance spectroscopy (hydrogen and carbon), and evaluated using toxicity tests. The optimum reaction conditions were as follows: n(lauric acid):n(camphene) = 2.5:1, m(titanium sulfate):m(camphene) = 0.25:1, reaction temperature of 80 °C, and reaction time of 25 h. Under these conditions, the content of isobornyl laurate in the product was 74.49%, and the content of purified product was 95.02%. The reaction kinetics for isobornyl laurate showed an apparent first-order reaction in the first 9 h with an activation energy of 31.01 kJ/mol. The reaction conditions of myristic acid, palmitic acid, and stearic acid were similar to those of lauric acid, but the reaction time had to be increased as the molecular weight of the fatty acid increased. Toxicity tests for four types of long-chain fatty acid isobornyl esters showed that the samples had low toxicity.
PubMed: 38005232
DOI: 10.3390/molecules28227510 -
Molecules (Basel, Switzerland) Nov 2023To disperse fatty acids in aqueous solution, choline, a quaternary ammonium ion, has been used recently. So far, only the self-assembly of myristic acid (MA) in the...
To disperse fatty acids in aqueous solution, choline, a quaternary ammonium ion, has been used recently. So far, only the self-assembly of myristic acid (MA) in the presence of choline hydroxide as a function of the molar ratio has been investigated, and, thus, the current understanding of these fatty acid systems is still limited. We investigated the self-assembly of palmitic acid (PA) in the presence of choline hydroxide (ChOH) as a function of the molar ratio () between ChOH and PA. The self-assemblies were characterized by phase contrast microscopy, cryo-TEM, small-angle X-ray scattering, and H NMR. The ionization state of PA was determined by pH, conductivity, and FT-IR measurements. With increase in , various self-assembled structures, including vesicles, lamellar phase, rigid membranes (large sheets, tubules, cones, and polyhedrals), and micelles, form in the PA/ChOH system, different from those of the MA/ChOH system. The change in induces pH variation and, consequently, a change in the PA ionization state, which, in turn, regulates the molecular interactions, including hydrogen bonding and electrostatic interaction, leading to various self-assemblies. Temperature is an important factor used to tune the self-assembly transitions. The fatty acid choline systems studied here potentially may be applicable in medicine, chemical engineering, and biotechnology.
PubMed: 38005186
DOI: 10.3390/molecules28227463 -
Brain : a Journal of Neurology Apr 2024The acyl-CoA-binding domain-containing protein 6 (ACBD6) is ubiquitously expressed, plays a role in the acylation of lipids and proteins and regulates the...
The acyl-CoA-binding domain-containing protein 6 (ACBD6) is ubiquitously expressed, plays a role in the acylation of lipids and proteins and regulates the N-myristoylation of proteins via N-myristoyltransferase enzymes (NMTs). However, its precise function in cells is still unclear, as is the consequence of ACBD6 defects on human pathophysiology. Using exome sequencing and extensive international data sharing efforts, we identified 45 affected individuals from 28 unrelated families (consanguinity 93%) with bi-allelic pathogenic, predominantly loss-of-function (18/20) variants in ACBD6. We generated zebrafish and Xenopus tropicalis acbd6 knockouts by CRISPR/Cas9 and characterized the role of ACBD6 on protein N-myristoylation with myristic acid alkyne (YnMyr) chemical proteomics in the model organisms and human cells, with the latter also being subjected further to ACBD6 peroxisomal localization studies. The affected individuals (23 males and 22 females), aged 1-50 years, typically present with a complex and progressive disease involving moderate-to-severe global developmental delay/intellectual disability (100%) with significant expressive language impairment (98%), movement disorders (97%), facial dysmorphism (95%) and mild cerebellar ataxia (85%) associated with gait impairment (94%), limb spasticity/hypertonia (76%), oculomotor (71%) and behavioural abnormalities (65%), overweight (59%), microcephaly (39%) and epilepsy (33%). The most conspicuous and common movement disorder was dystonia (94%), frequently leading to early-onset progressive postural deformities (97%), limb dystonia (55%) and cervical dystonia (31%). A jerky tremor in the upper limbs (63%), a mild head tremor (59%), parkinsonism/hypokinesia developing with advancing age (32%) and simple motor and vocal tics were among other frequent movement disorders. Midline brain malformations including corpus callosum abnormalities (70%), hypoplasia/agenesis of the anterior commissure (66%), short midbrain and small inferior cerebellar vermis (38% each) as well as hypertrophy of the clava (24%) were common neuroimaging findings. Acbd6-deficient zebrafish and Xenopus models effectively recapitulated many clinical phenotypes reported in patients including movement disorders, progressive neuromotor impairment, seizures, microcephaly, craniofacial dysmorphism and midbrain defects accompanied by developmental delay with increased mortality over time. Unlike ACBD5, ACBD6 did not show a peroxisomal localization and ACBD6-deficiency was not associated with altered peroxisomal parameters in patient fibroblasts. Significant differences in YnMyr-labelling were observed for 68 co- and 18 post-translationally N-myristoylated proteins in patient-derived fibroblasts. N-myristoylation was similarly affected in acbd6-deficient zebrafish and X. tropicalis models, including Fus, Marcks and Chchd-related proteins implicated in neurological diseases. The present study provides evidence that bi-allelic pathogenic variants in ACBD6 lead to a distinct neurodevelopmental syndrome accompanied by complex and progressive cognitive and movement disorders.
Topics: Animals; Female; Humans; Male; ATP-Binding Cassette Transporters; Intellectual Disability; Microcephaly; Movement Disorders; Nervous System Malformations; Neurodevelopmental Disorders; Tremor; Zebrafish; Infant; Child, Preschool; Child; Adolescent; Young Adult; Adult; Middle Aged
PubMed: 37951597
DOI: 10.1093/brain/awad380 -
Molecular & Cellular Proteomics : MCP Dec 2023Proteins can be modified by lipids in various ways, for example, by myristoylation, palmitoylation, farnesylation, and geranylgeranylation-these processes are...
Proteins can be modified by lipids in various ways, for example, by myristoylation, palmitoylation, farnesylation, and geranylgeranylation-these processes are collectively referred to as lipidation. Current chemical proteomics using alkyne lipids has enabled the identification of lipidated protein candidates but does not identify endogenous lipidation sites and is not readily applicable to in vivo systems. Here, we introduce a proteomic methodology for global analysis of endogenous protein N-terminal myristoylation sites that combines liquid-liquid extraction of hydrophobic lipidated peptides with liquid chromatography-tandem mass spectrometry using a gradient program of acetonitrile in the high concentration range. We applied this method to explore myristoylation sites in HeLa cells and identified a total of 75 protein N-terminal myristoylation sites, which is more than the number of high-confidence myristoylated proteins identified by myristic acid analog-based chemical proteomics. Isolation of myristoylated peptides from HeLa digests prepared with different proteases enabled the identification of different myristoylated sites, extending the coverage of N-myristoylome. Finally, we analyzed in vivo myristoylation sites in mouse tissues and found that the lipidation profile is tissue-specific. This simple method (not requiring chemical labeling or affinity purification) should be a promising tool for global profiling of protein N-terminal myristoylation.
Topics: Humans; Animals; Mice; Myristic Acid; HeLa Cells; Proteomics; Proteins; Peptides; Liquid-Liquid Extraction; Protein Processing, Post-Translational
PubMed: 37949301
DOI: 10.1016/j.mcpro.2023.100677 -
Journal of Dairy Science Apr 2024Recently, the interest in improving livestock product nutraceutical profiles through sustainable feeding systems has increased. In this context, the overall quality and...
Recently, the interest in improving livestock product nutraceutical profiles through sustainable feeding systems has increased. In this context, the overall quality and nutraceutical profiles were examined in dairy products obtained from 16 lactating Cinisara cows given an integrated feed in dry season with Opuntia ficus-indica cladodes. Two homogeneous groups of cows (milk yield: 6.3 ± 1.5 kg; body weight: 213 ± 55 kg) were fed with 2 different diets (CON: pasture and wheat bran; OFI: pasture, wheat bran, and cladodes), according to a 2 × 2 Latin square design. The bulk milk produced during the study was used to make Caciotta cheese and was analyzed at 0, 15, and 30 storage days. Milk and cheese samples were analyzed for chemical, physical, and microbiological traits. The nutraceutical and sensorial profiles, as well as the antioxidant capacity, were also determined in the final products. For milk, the urea content in individual samples was reduced in OFI but not in CON. In the cheese, integration of cladodes did not influence the starter cultures development with 2 strains of Streptococcus thermophilus, but it caused a higher content of polyphenols and a consequent greater antioxidant capacity and a change in the fatty acids profile. In particular, the caprylic, capric, lauric, myristic, and palmitic fatty acids were higher, as were the petroselinic, vaccenic, rumenic, and α-linolenic fatty acids. In contrast, the oleic and the γ-linolenic fatty acids were lower for OFI. The cheese from the OFI group showed better overall acceptability, and a higher yellow color, odor intensity, and butter flavor. The multivariate analysis well distinguished the cheeses belonging to the 2 groups. Further investigations should be conducted to formulate well-balanced diets that include cladodes for Cinisara lactating cows, but also to determine the content of other important bioactive compounds in fresh and treated cladodes, as well as their effects on animal welfare and production.
Topics: Female; Cattle; Animals; Antioxidants; Opuntia; Lactation; Diet; Milk; Fatty Acids; Dietary Fiber; Animal Feed
PubMed: 37944810
DOI: 10.3168/jds.2023-23847 -
Microorganisms Oct 2023In this research, six strains of oleaginous yeasts native to southern Chile were analyzed for their biotechnological potential in lipid accumulation. For this purpose,...
In this research, six strains of oleaginous yeasts native to southern Chile were analyzed for their biotechnological potential in lipid accumulation. For this purpose, the six strains, named PP1, PP4, PR4, PR10, PR27 and PR29, were cultivated in a nitrogen-deficient synthetic mineral medium (SMM). Then, two strains were selected and cultivated in an industrial residual "vinasse", under different conditions of temperature (°C), pH and carbon/nitrogen (C/N) ratio. Finally, under optimized conditions, the growth kinetics and determination of the lipid profile were evaluated. The results of growth in the SMM indicate that yeasts PP1 and PR27 presented biomass concentrations and lipid accumulation percentages of 2.73 and 4.3 g/L of biomass and 36.6% and 45.3% lipids, respectively. Subsequently, for both strains, when cultured in the residual vinasse under optimized environmental conditions, biomass concentrations of 14.8 ± 1.51 g/L (C/N 80) and 15.83 ± 0.57 g/L (C/N 50) and lipid accumulations of 28% and 30% were obtained for PP1 and PR27, respectively. The composition of the triglycerides (TGs), obtained in the culture of the yeasts in a 2 L reactor, presented 64.25% of saturated fatty acids for strain PR27 and 47.18% for strain PP1. The saturated fatty acid compositions in both strains are mainly constituted of fatty acids, myristic C 14:0, heptadecanoic C 17:0, palmitic C 16:0 and stearic C 18:0, and the monounsaturated fatty acids constituted of oleic acid C 18:1 (cis 9) (28-46%), and in smaller amounts, palmitoleic acid and heptadecenoic acid. This work demonstrates that the native yeast strains PP1 and PR27 are promising strains for the production of microbial oils similar to conventional vegetable oils. The potential applications in the energy or food industries, such as aquaculture, are conceivable.
PubMed: 37894174
DOI: 10.3390/microorganisms11102516 -
Gels (Basel, Switzerland) Oct 2023The larvae of the Black Soldier Fly (BSF, ) have been introduced as one of the tools to create a circular economy model, which will be used in areas such as waste...
The larvae of the Black Soldier Fly (BSF, ) have been introduced as one of the tools to create a circular economy model, which will be used in areas such as waste management and the treatment of industrial by-products to produce high-added-value food grade ingredients. The main aim of this research was to investigate the fat composition and antimicrobial activity against food pathogens and spoilers of Black Soldier Fly larvae. The research revealed that the Black Soldier Fly larvae fats are predominantly lauric fatty (40.93%), which are followed by palmitic, oleic, myristic, linolenic and palmitoleic fatty acids, accounting for 19.11, 17.34, 6.49, 8.79 and 3.89% of the fatty acid content, respectively. The investigation of the fats showed stability through a one-year monitoring period with no indication of chemical or microbiological spoilage. Different fat fractions were tested for antimicrobial activity, which showed efficiency against (the inhibition zone varied from 10.5 to 12.5 mm), (from 12.5 to 16.5 mm), (12.5 mm) and (10.0 mm). The inhibitory effect on was confirmed by shelf-life studies using larvae fat-based oleogel in a model food matrix. GraphPad Prism (ver. 8.0.1) was used for the statistical data processing. This research revealed the potential of Black Soldier Fly larvae fat as a very stable ingredient with promising antibacterial properties that can extend the product shelf-life in food matrixes even when used in relatively small amounts.
PubMed: 37888366
DOI: 10.3390/gels9100793 -
Journal of Materials Chemistry. B Nov 2023Emulsion-templated foams have displayed promise as injectable bone grafts; however, the use of a surfactant as an emulsifier resulted in relatively small pores and...
Emulsion-templated foams have displayed promise as injectable bone grafts; however, the use of a surfactant as an emulsifier resulted in relatively small pores and impedes cell attachment. Hydroxyapatite nanoparticles were explored as an alternative stabilizer to address these limitations. To this end, hydroxyapatite nanoparticles were first modified with myristic acid to generate the appropriate balance of hydrophobicity to stabilize a water-in-oil emulsion of neopentyl glycol diacrylate and 1,4-butanedithiol. surface modification of the resulting foam with hydroxyapatite was confirmed with elemental mapping and transmission electron microscopy. Nanoparticle-stabilized foams displayed improved human mesenchymal stem cell viability (91 ± 5%) over surfactant-stabilized foams (23 ± 11%). Although the pore size was appropriate for bone grafting applications (115 ± 71 μm), the foams lacked the interconnected architecture necessary for cell infiltration. We hypothesized that a co-stabilization approach with both surfactant and nanoparticles could be used to achieve interconnected pores while maintaining improved cell attachment and larger pore sizes. A range of hydroxyapatite nanoparticle and surfactant concentrations were investigated to determine the effects on microarchitecture and cell behavior. By balancing these interactions, a co-stabilized foam was identified that possessed large, interconnected pores (108 ± 67 μm) and improved cell viability and attachment. The co-stabilized foam was then evaluated as an injectable bone graft including network formation, microscale integration with bone, push out strength, and compressive properties. Overall, this work demonstrated that surface modification with nHA improved cell attachment while retaining desirable bone grafting features and injectability.
Topics: Humans; Porosity; Bone Transplantation; Emulsions; Durapatite; Nanoparticles; Surface-Active Agents
PubMed: 37878081
DOI: 10.1039/d3tb01839c -
Animals : An Open Access Journal From... Sep 2023Maternal genetic effects (MGE) could affect meat quality traits such as intramuscular fat (IMF) and its fatty acid composition. However, it has been scarcely studied,...
Maternal genetic effects (MGE) could affect meat quality traits such as intramuscular fat (IMF) and its fatty acid composition. However, it has been scarcely studied, especially in rabbits. The objectives of the present study were, first, to assess the importance of MGE on intramuscular fat and fatty acid composition by applying a Bayesian maternal animal model in two rabbit lines divergently selected for IMF. The second objective was to identify genomic regions and candidate genes of MGE that are associated with the traits of these offspring, using Bayesian methods in a Genome Wide Association Study (GWAS). Quantitative analyses were performed using data from 1982 rabbits, and 349 animals from the 9th generation and 76 dams of the 8th generation with 88,512 SNPs were used for the GWAS. The studied traits were IMF, saturated fatty acids (total SFA, C14:0; myristic acid, C16:0; palmitic acid and C18:0; stearic acid), monounsaturated fatty acids (total MUFA, C16:1n-7; palmitoleic acid and C18:1n-9; oleic acid), polyunsaturated fatty acids (total PUFA, C18:2n-6; linoleic acid, C18:3n-3; α-linolenic acid and C20:4n-6; arachidonic acid), MUFA/SFA and PUFA/SFA. The proportion of phenotypic variance explained by the maternal genetic effect ranged from 8 to 22% for IMF, depending on the model. For fatty acid composition, the proportion of phenotypic variance explained by maternal genetic effects varied from 10% (C18:0) to 46% (MUFA) in a model including both direct and additive maternal genetic effects, together with the common litter effect as a random variable. In particular, there were significant direct maternal genetic correlations for C16:0, C18:1n9, C18:2n6, SFA, MUFA, and PUFA with values ranging from -0.53 to -0.89. Relevant associated genomic regions were located on the rabbit chromosomes (OCU) OCU1, OCU5 and OCU19 containing some relevant candidates (, , , , , , , and ) related to lipid metabolism, binding, and obesity. These regions explained about 1.2 to 13.9% of the total genomic variance of the traits studied. Our results showed an important maternal genetic effect on IMF and its fatty acid composition in rabbits and identified promising candidate genes associated with these traits.
PubMed: 37835677
DOI: 10.3390/ani13193071 -
Food Science & Nutrition Oct 2023The current study investigated the antiadipogenic mechanism of krill oil from the 3T3-L1 adipocytes. The krill oil adhered to the criteria as a food standard by showing...
The current study investigated the antiadipogenic mechanism of krill oil from the 3T3-L1 adipocytes. The krill oil adhered to the criteria as a food standard by showing 50.8% of the total phospholipid, 5.27% myristic acid, and 1.63% linoleic acid. The lipid accumulation that was measured in the 3T3-L1 cells using oil red O staining was reduced up to 54% by the krill oil. The krill oil treatment reduced the adipogenic transcription factors by downregulating the sterol regulatory element binding protein 1 (SREBP1) and acetyl-CoA carboxylase (ACC), phospho-ACC, and AMP-activated protein kinase (AMPK) phosphorylation. The current study confirmed that the krill oil inhibited adipogenesis by downregulating SREBP1 and ACC via the upregulation of the AMPK and nuclear factors E2-related factor 2 (Nrf2) signaling pathway in the 3T3-L1 adipocytes. These findings suggest that krill oil is a good source of phospholipid and phosphatidylcholine, which could be a potential natural antiobesity ingredient by inhibiting adipogenesis.
PubMed: 37823164
DOI: 10.1002/fsn3.3576