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1.
Food Chem ; 462: 141008, 2025 Jan 01.
Article in English | MEDLINE | ID: mdl-39217746

ABSTRACT

Hydrophobic bioactive compounds like astaxanthin (AST) exhibit poor water solubility and low bioavailability. Liposomes, which serve as nanocarriers, are known for their excellent biocompatibility and minimal immunogenicity. Traditionally, liposomes have been primarily constructed using phospholipids and cholesterol. However, the intake of cholesterol may pose a risk to human health. Phytosterol ester was reported to reduce level of cholesterol and improve properties of liposomes. In this study, phytosterol oleate was used to prepare liposomes instead of cholesterol to deliver AST (AST-P-Lip). The size range of AST-P-Lip was 100-220 nm, and the morphology was complete and uniform. In vitro studies showed that AST-P-Lip significantly enhanced the antioxidant activity and oral bioavailability of AST. During simulated digestion, AST-P-Lip protected AST from damage by gastric and intestinal digestive fluid. Additionally, AST-P-Lip had a good storage stability and safety. These results provide references for the preparation of novel liposomes and the delivery of bioactive compounds.


Subject(s)
Cholesterol , Liposomes , Phytosterols , Xanthophylls , Liposomes/chemistry , Xanthophylls/chemistry , Xanthophylls/pharmacology , Xanthophylls/administration & dosage , Humans , Phytosterols/chemistry , Phytosterols/pharmacology , Phytosterols/administration & dosage , Cholesterol/chemistry , Particle Size , Biological Availability , Oleic Acid/chemistry , Drug Compounding , Animals , Antioxidants/chemistry , Antioxidants/pharmacology
2.
Food Res Int ; 194: 114927, 2024 Oct.
Article in English | MEDLINE | ID: mdl-39232539

ABSTRACT

In this study, the potential mechanism of aroma loss in non-smoked bacon due to excessive hot air drying (beyond 24 h) was investigated, focusing on protein conformational changes and the inhibition of heme protein-mediated lipid oxidation by oleic acid. The results showed that prolonged hot-air drying caused a stretching of the myofibrillar protein (MP) conformation in bacon before 36 h, leading to an increase in reactive sulfhydryl groups, surface hydrophobicity, and the exposure of additional hydrophobic sites. Consequently, the binding ability of MP to the eight key aroma compounds (hexanal, 1-octen-3-ol, (E)-2-nonenal, 3-methyl-butanoic acid, 2-undecenal, (E, E)-2,4-decadienal, 2,3-octanedione, and dihydro-5-pentyl-2(3H)-furanone) was enhanced, resulting in their retention. On the other hand, a sustained increase in oleic acid levels has been demonstrated to effectively inhibit heme protein-mediated lipid oxidation and the formation of these key aroma compounds. Using lipidomic techniques, 30 lipid molecules were identified as potential precursors of oleic acid during the bacon drying process. Among these precursors, triglycerides (16:0/18:0/18:1) may be the most significant.


Subject(s)
Hot Temperature , Odorants , Odorants/analysis , Desiccation/methods , Meat Products/analysis , Oleic Acid/chemistry , Food Handling/methods , Hydrophobic and Hydrophilic Interactions , Protein Conformation , Volatile Organic Compounds/analysis , Volatile Organic Compounds/chemistry , Oxidation-Reduction , Aldehydes/analysis , Aldehydes/chemistry
3.
Article in English | MEDLINE | ID: mdl-39128394

ABSTRACT

The aim of the present study was to elucidate unknown effects of intraocular fatty acids (ioFAs) including palmitic acid (C16:0), stearic acid (C18:0), oleic acid (C18:1), linoleic acid (C18:2), arachidonic acid (C20:4), eicosapentaenoic acid (EPA, C20:5) and docosahexaenoic acid (DHA, C22:6) on the outer blood-retinal barrier (oBRB). For this purpose, human retinal pigment epithelium cell line ARPE19 was subjected to analyses for evaluating the following biological phenotypes: (1) cell viability, (2) cellular metabolic functions, (3) barrier functions by trans-epithelial electrical resistance (TEER), and (4) expression of tight junction (TJ) molecules. In the presence of 100 nM ioFAs, no significant effects on cell viability of ARPE19 cells was observed. While treatment with EPA or DHA tended to reduce non-mitochondrial oxygen consumption, most indices in mitochondrial functions were not markedly affected by treatment with ioFAs in ARPE19 cells. On the other hand, ioFAs except for palmitic acid and stearic acid significantly increased basal extracellular acidification rates, suggesting activated glycolysis or increased lactate production. Interestingly, TEER values of planar ARPE19 monolayer were significantly increased by treatment any ioFAs. Consistently, gene expression levels of TJ proteins were increased by treatment with ioFAs. Collectively, the findings presented herein suggest that ioFAs may contribute to reinforcement of barrier functions of the oBRB albeit there are some differences in biological effects depending on the type of ioFAs.


Subject(s)
Blood-Retinal Barrier , Retinal Pigment Epithelium , Humans , Blood-Retinal Barrier/metabolism , Blood-Retinal Barrier/drug effects , Retinal Pigment Epithelium/metabolism , Retinal Pigment Epithelium/drug effects , Retinal Pigment Epithelium/cytology , Cell Line , Fatty Acids/metabolism , Fatty Acids/pharmacology , Cell Survival/drug effects , Palmitic Acid/pharmacology , Docosahexaenoic Acids/pharmacology , Stearic Acids/pharmacology , Linoleic Acid/pharmacology , Eicosapentaenoic Acid/pharmacology , Oleic Acid/pharmacology , Tight Junctions/metabolism , Tight Junctions/drug effects , Arachidonic Acid/pharmacology , Arachidonic Acid/metabolism
4.
Waste Manag ; 189: 34-43, 2024 Dec 01.
Article in English | MEDLINE | ID: mdl-39173470

ABSTRACT

Glycerine pitch is a highly alkaline residue from the oleochemical industry that contains glycerol and contaminants, such as water, soap, salt and ash. In this study, acidic heterogeneous glycerol-based carbon catalysts were synthesised for biodiesel production via single-step partial carbonisation and sulfonation using pure glycerol and glycerine pitch, producing products labelled as SGC and SGPC, respectively. Carbon materials were obtained by heating glycerol and concentrated sulfuric acid (1:3) at 200℃ for 1 h. The produced SGC and SGPC displayed high densities of sulfonic group (-SO3H), i.e. 1.49 and 1.00 mmol·g-1, respectively, alongside carboxylic (-COOH) and phenolic (-OH) acid. In the catalytic evaluation, excellent oleic acid conversions of 96.0 ± 0.4 % and 92.4 ± 0.5 % were achieved using SGC and SGPC, respectively, under optimised reaction conditions: 1:10 M ratio of oleic acid to methanol, 5 % (w/w) catalyst, 64℃ and 5 h. SGPC was found to be recyclable with 68.5 % conversion after the 6th cycle, which was attributed to the loss of -SO3H and catalyst deactivation by the deposition of oleic acid on its surface. Remarkably, despite the impurities present in the glycerine pitch, the obtained results demonstrated that the reactivity of SGPC is comparable to SGC and superior to that of commercial solid acid catalysts, which demonstrated that the presence of impurities appears to have minimal impact on the production of carbon materials and their properties.


Subject(s)
Biofuels , Carbon , Glycerol , Glycerol/chemistry , Catalysis , Biofuels/analysis , Carbon/chemistry , Sulfonic Acids/chemistry , Oleic Acid/chemistry , Sulfuric Acids/chemistry , Industrial Waste
5.
Lipids Health Dis ; 23(1): 241, 2024 Aug 08.
Article in English | MEDLINE | ID: mdl-39118087

ABSTRACT

BACKGROUND: This study aimed to explore the potential associations between trans fatty acid (TFA) and α-klotho levels. METHODS: Datasets from the 2009-2010 National Health and Nutrition Examination Survey (NHANES) were analysed for this study. Multivariable linear regression and restricted cubic spline (RCS) analyses were performed to examine the relationships between plasma TFA and serum α-klotho levels. RESULTS: A total of 1,205 participants were included, with a geometric mean (GM) of 803.60 (95% CI: 787.45, 820.00) pg/mL for serum α-klotho levels. RCS analysis revealed L-shaped relationships between TFA and α-klotho levels. The inflection points for palmitelaidic acid (PA), vaccinic acid (VA), elaidic acid (EA), and total TFA levels were 4.55, 20.50, 18.70, and 46.40 µmol/L, respectively. Before reaching the inflection point, serum α-klotho levels were negatively correlated with plasma PA, VA, EA and total TFA levels, with ß values (95% CI) of -0.15 (-0.24, -0.06), -0.16 (-0.23, -0.09), -0.14 (-0.22, -0.05) and - 0.19 (-0.27, -0.11), respectively. Linolelaidic acid (LA) levels exhibited an inverse and linear association with α-klotho levels ( Pnonlinearity=0.167, Poverall<0.001). L-shaped relationships between TFA and α-klotho levels were also observed in the subgroups of participants who were aged < 65 years, were male, did not exercise, were ex-smokers, and were overweight/obese. CONCLUSIONS: L-shaped correlations between plasma PA, VA, EA, and total TFA levels and serum α-klotho levels were observed among adults in the United States.


Subject(s)
Klotho Proteins , Nutrition Surveys , Trans Fatty Acids , Humans , Male , Female , United States/epidemiology , Middle Aged , Adult , Trans Fatty Acids/blood , Glucuronidase/blood , Aged , Oleic Acids/blood , Oleic Acid/blood , Linear Models
6.
Article in English | MEDLINE | ID: mdl-39147448

ABSTRACT

In the present study, we investigated the genotoxicity of the active products formed from N-nitrosoproline (NPRO) dissolved in oleic acid following ultraviolet A (UVA) irradiation, bypassing the need for metabolic activation. We previously demonstrated the photomutagenicity of NPRO dissolved in a phosphate-buffered solution. It has been suggested that the association of the nitrosamine group with acid ions facilitates rapid photodissociation and photoactivation. We hypothesized that NPRO's inherent carboxyl group may mimic an acid, inducing photodissociation and photomutagenicity, even in a non-aqueous solvent lacking acidic ions. Following UVA irradiation, NPRO dissolved in oleic acid exhibited a dose-dependent mutagenic activity. Similar results were obtained when NPRO was dissolved in linoleic acid and triolein. Nitric oxide formation, which is dependent on NPRO concentration, is accompanied by mutagenic activity. The mutagenicity spectrum obtained in response to NPRO irradiation followed the absorption curve of NPRO dissolved in oleic acid. Irradiated NPRO in oleic acid displayed relative stability, retaining approximately 18, 36, and 63 % of initial mutagenicity after 10 days of storage at 25, 4, and -20 °C, respectively. Thus NPRO stored in a fatty environment undergoes photoactivation upon irradiation, leading to genotoxicity.


Subject(s)
Mutagenicity Tests , Oleic Acid , Solvents , Ultraviolet Rays , Oleic Acid/chemistry , Solvents/chemistry , Mutagens/chemistry , Mutagens/toxicity , Nitric Oxide/chemistry , Nitric Oxide/metabolism , Salmonella typhimurium/drug effects , Salmonella typhimurium/genetics , Salmonella typhimurium/radiation effects
7.
Food Res Int ; 192: 114749, 2024 Sep.
Article in English | MEDLINE | ID: mdl-39147554

ABSTRACT

This research aims to assess the effect of amino acids as lipid antioxidants in reducing the formation of volatile aldehydes in frying oil. Methionine, histidine, and glycine at concentrations of 2.5, 5, and 10 mM were added to high oleic sunflower oil (HOSO) to investigate their effects on the distribution and formation of saturated, monounsaturated, and polyunsaturated volatile aldehydes. The results showed that the proportion of saturated volatile aldehydes was greater than that of unsaturated ones; Methionine exhibited the best inhibitory effect, after 12 h of frying, 10 mM methionine reduced the content of saturated volatile aldehydes by 24.21 %, monounsaturated by 52.4 %, and polyunsaturated by 54.73 % compared to the control. Methionine's sulfur-containing side chain was also proven to have strong antioxidant activity. Combined with the results of this study, this can also provide insights for using amino acids as lipid antioxidants.


Subject(s)
Aldehydes , Amino Acids , Antioxidants , Cooking , Hot Temperature , Sunflower Oil , Sunflower Oil/chemistry , Aldehydes/analysis , Antioxidants/analysis , Amino Acids/analysis , Methionine/chemistry , Plant Oils/chemistry , Volatile Organic Compounds/analysis , Histidine/analysis , Histidine/chemistry , Oleic Acid/analysis , Glycine/chemistry
8.
Cancer Cell ; 42(8): 1386-1400.e8, 2024 Aug 12.
Article in English | MEDLINE | ID: mdl-39137727

ABSTRACT

Changes in plasma and fecal metabolomes in colorectal cancer (CRC) progression (normal-adenoma-CRC) remain unclear. Here, plasma and fecal samples were collected from four independent cohorts of 1,251 individuals (422 CRC, 399 colorectal adenoma [CRA], and 430 normal controls [NC]). By metabolomic profiling, signature plasma and fecal metabolites with consistent shift across NC, CRA, and CRC are identified, including CRC-enriched oleic acid and CRC-depleted allocholic acid. Oleic acid exhibits pro-tumorigenic effects in CRC cells, patient-derived organoids, and two murine CRC models, whereas allocholic acid has opposing effects. By integrative analysis, we found that oleic acid or allocholic acid directly binds to α-enolase or farnesoid X receptor-1 in CRC cells, respectively, to modulate cancer-associated pathways. Clinically, we establish a panel of 17 plasma metabolites that accurately diagnoses CRC in a discovery and three validation cohorts (AUC = 0.848-0.987). Overall, we characterize metabolite signatures, mechanistic significance, and diagnostic potential of plasma and fecal metabolomes in CRC.


Subject(s)
Adenoma , Biomarkers, Tumor , Colorectal Neoplasms , Disease Progression , Feces , Metabolomics , Humans , Colorectal Neoplasms/diagnosis , Colorectal Neoplasms/metabolism , Colorectal Neoplasms/blood , Colorectal Neoplasms/pathology , Feces/chemistry , Adenoma/metabolism , Adenoma/diagnosis , Adenoma/pathology , Adenoma/blood , Metabolomics/methods , Animals , Biomarkers, Tumor/metabolism , Biomarkers, Tumor/blood , Mice , Male , Female , Early Detection of Cancer/methods , Metabolome , Middle Aged , Oleic Acid/metabolism , Oleic Acid/blood , Aged
9.
J Vis Exp ; (209)2024 Jul 19.
Article in English | MEDLINE | ID: mdl-39141537

ABSTRACT

The prevalence of metabolic dysfunction-associated steatotic liver disease (MASLD) has surged due to changes in economic and lifestyle patterns, leading to significant health challenges. Previous reports have studied the establishment of animal and cellular models for MASLD, highlighting differences between them. In this study, a cellular model was created by inducing fat accumulation in MASLD. HepG2 cells were stimulated with the unsaturated fatty acid oleic acid at various concentrations (0.125 mM, 0.25 mM, 0.5 mM, 1 mM) to emulate MASLD. The model's efficacy was assessed using cell counting kit-8 assays, Oil Red O staining, and lipid content analysis. This study aimed to create a simple-to-operate cellular model for MASLD cells. Results from the cell counting kit-8 assays showed that the survival of HepG2 cells was dependent on the concentration of oleic acid, with a GI50 of 1.875 mM. Cell viability in the 0.5 mM and 1 mM groups were significantly lower than those in the control group (P < 0.05). Furthermore, Oil Red O staining and lipid content analysis examined fat deposition at varying oleic acid concentrations (0.125 mM, 0.25 mM, 0.5 mM, 1 mM) on HepG2 cells. The lipid content of the 0.25 mM, 0.5 mM, and 1 mM groups was significantly higher than that of the control group (P < 0.05). Additionally, triglyceride levels in the OA groups were significantly higher than those in the control group (P < 0.05).


Subject(s)
Fatty Liver , Oleic Acid , Humans , Hep G2 Cells , Oleic Acid/pharmacology , Fatty Liver/metabolism , Fatty Liver/pathology , Azo Compounds , Lipid Metabolism/physiology , Models, Biological
10.
Methods Mol Biol ; 2851: 107-114, 2024.
Article in English | MEDLINE | ID: mdl-39210175

ABSTRACT

Hydroxy fatty acids (HFAs) are fatty acids with hydroxyl functional groups attached to the main chain. HFAs are used in widely diverse industrial applications, healthy functional foods, artificial food flavorings, and alcoholic beverages. A lactic acid bacterium (LAB), Lactobacillus sakei, hydroxylates oleic acid. Furthermore, the hydroxyl fatty acid was identified by GC-MS as 10-hydroxystearic acid. The Lactobacillus sakei hydroxylated more than 90% of the oleic acid in the medium at 15 °C after 30-48 h. The hydroxyl enzyme needs a coenzyme for an electron donor as NADPH. The enzyme is useful for assay with monitoring NADPH concentration used an A340 device. The hydroxylate fatty acids are converted by LAB lactonize aroma lactone from commercial yeast strains, which can be detected directly by scent. Commercial beer brewing yeast T-58 produced the highest concentration of aroma lactone from hydroxyl fatty acids. Furthermore, the aroma lactone is identified by GC-MS as gamma-dodecalactone. The ratio of conversion is 87%. These results suggest that the lactonization conversion system is useful to hydroxylate fatty acids for alcoholic beverages.


Subject(s)
Fatty Acids , Gas Chromatography-Mass Spectrometry , Hydroxylation , Fatty Acids/metabolism , Fatty Acids/chemistry , Lactobacillales/metabolism , Lactones/metabolism , Oleic Acid/metabolism
11.
Cell ; 187(17): 4586-4604.e20, 2024 Aug 22.
Article in English | MEDLINE | ID: mdl-39137778

ABSTRACT

Respiratory infections cause significant morbidity and mortality, yet it is unclear why some individuals succumb to severe disease. In patients hospitalized with avian A(H7N9) influenza, we investigated early drivers underpinning fatal disease. Transcriptomics strongly linked oleoyl-acyl-carrier-protein (ACP) hydrolase (OLAH), an enzyme mediating fatty acid production, with fatal A(H7N9) early after hospital admission, persisting until death. Recovered patients had low OLAH expression throughout hospitalization. High OLAH levels were also detected in patients hospitalized with life-threatening seasonal influenza, COVID-19, respiratory syncytial virus (RSV), and multisystem inflammatory syndrome in children (MIS-C) but not during mild disease. In olah-/- mice, lethal influenza infection led to survival and mild disease as well as reduced lung viral loads, tissue damage, infection-driven pulmonary cell infiltration, and inflammation. This was underpinned by differential lipid droplet dynamics as well as reduced viral replication and virus-induced inflammation in macrophages. Supplementation of oleic acid, the main product of OLAH, increased influenza replication in macrophages and their inflammatory potential. Our findings define how the expression of OLAH drives life-threatening viral disease.


Subject(s)
COVID-19 , Influenza, Human , Animals , Humans , Mice , COVID-19/virology , COVID-19/genetics , Influenza, Human/virology , Virus Replication , Macrophages/metabolism , Macrophages/virology , Female , Male , SARS-CoV-2 , Lung/virology , Lung/pathology , Lung/metabolism , Mice, Inbred C57BL , Oleic Acid/metabolism , Respiratory Syncytial Virus Infections/virology , Mice, Knockout , Viral Load , Carboxylic Ester Hydrolases/metabolism , Carboxylic Ester Hydrolases/genetics , Orthomyxoviridae Infections/virology , Respiratory Tract Infections/virology , Child
12.
Eur J Pharm Sci ; 201: 106874, 2024 Oct 01.
Article in English | MEDLINE | ID: mdl-39121923

ABSTRACT

Trazodone is a triazolpyridine derivative approved for the treatment of depression, and currently marketed as oral formulations. The transdermal administration of this drug could reduce side effects, related to peak plasma concentration, and improve patient adherence due to a reduced administration frequency. The aims of this work were: (a) the evaluation of the effect of pH vehicle and permeation enhancers on trazodone permeability across porcine skin ex-vivo; (b) the development and optimization of a transdermal drug delivery system containing trazodone hydrochloride. From the results obtained, it was found that the effect of pH of the vehicle on the permeation of trazodone across the skin is quite complex, because it influences both solubility and partitioning and that the presence of fatty acids in the vehicle has a notable effect on permeation (the enhancement factor obtained was approx. 100). For both the fatty acid selected (oleic and lauric) a parabolic relationship between the transdermal flux and the concentration was found, with an optimum activity in the range 2-3 %. In the second part of the work, different patches were prepared and tested ex-vivo. Overall, the results obtained seem to highlight that drug loading, rather than the components of the adhesive matrix, plays the most relevant role for the permeation of trazodone. The addition of lauric acid, which produced a considerable enhancement in solution, was not effective when included in the patch. The obtained data are promising although probably not clinically relevant for the treatment of depression, but might be interesting for the treatment of insomnia and anxiety disorder, which require much lower doses.


Subject(s)
Administration, Cutaneous , Skin Absorption , Trazodone , Trazodone/administration & dosage , Trazodone/pharmacokinetics , Animals , Swine , Skin Absorption/drug effects , Skin/metabolism , Skin/drug effects , Permeability , Oleic Acid/chemistry , Solubility , Hydrogen-Ion Concentration , Lauric Acids/chemistry , Lauric Acids/administration & dosage , Transdermal Patch , Chemistry, Pharmaceutical/methods , Antidepressive Agents, Second-Generation/administration & dosage , Antidepressive Agents, Second-Generation/pharmacokinetics , Drug Delivery Systems/methods
13.
AAPS PharmSciTech ; 25(6): 180, 2024 Aug 06.
Article in English | MEDLINE | ID: mdl-39107558

ABSTRACT

In recent years, there has been a significant increase in the prevalence of thyroid diseases, particularly hypothyroidism. In this study, we investigated the impact and mechanisms of Chemical permeation enhancement(CPE) on transdermal permeation of levothyroxine sodium (L-T4) patches.We found that the combination of oleic acid (OA) and Azone (NZ) yielded the best transdermal permeation effect for L-T4.Subsequently, we also investigated the relevant propermeability mechanism.The results demonstrate that the combined application of OA and NZ significantly enhances the transdermal permeation of L-T4 compared to individual applications,it is attributed to two mechanisms: firstly, OA improves drug release by increasing the flowability of the pressure-sensitive adhesive (PSA) matrix; secondly, both OA and NZ act on the stratum corneum, especially facilitating L-T4 permeation through the hair follicle pathway. No skin irritation or cytotoxicity is observed with these final patches, which exhibit a remarkable therapeutic effect on hypothyroidism. this study contributes to the development of transdermal formulations of L-T4.


Subject(s)
Administration, Cutaneous , Oleic Acid , Skin Absorption , Thyroxine , Oleic Acid/chemistry , Thyroxine/administration & dosage , Thyroxine/pharmacology , Thyroxine/pharmacokinetics , Animals , Skin Absorption/drug effects , Transdermal Patch , Skin/metabolism , Skin/drug effects , Drug Liberation , Mice , Permeability , Hypothyroidism/drug therapy , Hypothyroidism/metabolism , Humans , Chemistry, Pharmaceutical/methods , Male
14.
Int J Pharm ; 664: 124588, 2024 Oct 25.
Article in English | MEDLINE | ID: mdl-39153644

ABSTRACT

This study investigates the biodistribution of a nano lipid carrier system (NLCs) containing the hydrophobic drug erlotinib (ERL-NLCs). The system was labelled with the fluorescent dye IR-780 for real-time dynamic imaging. ERL-NLCs were initially developed using the ultrasonication method with oleic acid and stearic acid. In vitro and ex vivo studies were performed to confirm the formation and penetration of NLCs within the intestine. Subsequently, the biological distribution of ERL-NLCs was monitored using a fluorescent dye through the IVIS® fluorescent optical imaging technique in whole live animals. Mice were orally administered blank IR 780 dye solution, ERL suspension, and IR 780 labelled NLCs. Fluorescence images were acquired at different time intervals up to 24 h and then total radiant efficiency was calculated through the region of interest (ROI) of the whole animal at each interval of time for all three groups. To validate the results obtained from in vivo imaging, various organs including lungs, heart, liver, both kidneys, stomach, and intestine were subsequently extracted and examined after 24 h. The ROI was found to be higher in the blank IR 780 dye solution, followed by the drug suspension and IR 780 labelled NLCs. These results confirm that the plain ERL suspension distributes across the body, and its encapsulation in NLCs facilitates passage through the lymphatic intestinal pathway, effectively avoiding first-pass metabolism. The remarkable results indicated that the NLCs formulation effectively circumvents first-pass metabolism by adopting the intestinal lymphatic pathway, thereby enhancing the oral bioavailability of the drug. This observed behaviour underscores the potential of NLCs in optimizing drug delivery and minimizing adverse effects associated with gastrointestinal and metabolic processes.


Subject(s)
Drug Carriers , Erlotinib Hydrochloride , Fluorescent Dyes , Nanoparticles , Optical Imaging , Animals , Erlotinib Hydrochloride/administration & dosage , Erlotinib Hydrochloride/pharmacokinetics , Tissue Distribution , Fluorescent Dyes/administration & dosage , Fluorescent Dyes/chemistry , Fluorescent Dyes/pharmacokinetics , Administration, Oral , Drug Carriers/chemistry , Optical Imaging/methods , Mice , Nanoparticles/chemistry , Lipids/chemistry , Indoles/pharmacokinetics , Indoles/administration & dosage , Indoles/chemistry , Oleic Acid/chemistry , Male
15.
Int J Pharm ; 661: 124380, 2024 Aug 15.
Article in English | MEDLINE | ID: mdl-38950661

ABSTRACT

Melanoma is an aggressive form of skin cancer with elevated propensity to metastasize. One of the major critical issues in the treatment of oncological patients is represented by the development of toxicity and resistance to the available therapies. Great progress has been made in the field of nanotechnologies to limit the unwanted effects of anti-cancer treatments. We explored the potential of creating oil-in-water nanoemulsions composed of oleic acid, as a bioactive carrier for lipophilic drug delivery. This bioactive nanoemulsion was loaded with Curcumin, a natural fluorescent lipophilic compound, used as a model drug to evaluate nanoemulsion capability to: i) encapsulate the lipophilic moiety; ii) interact with the specific cells, and iii) improve the efficacy of the loaded model drug compared to the free one. Therefore, we evaluated the physical-chemical features of Curcumin-loaded nanoemulsions, confirming their pH sensibility and their stability over time. Moreover, the nanoemulsions were able to preserve the loaded Curcumin by degradation/destabilization phenomena. Finally, we verified some of the biological functions of Curcumin delivered by nanoemulsions in the B16F10 melanoma cell line. We obtained evidence of the biological action of Curcumin, suggesting oleic-based nanoemulsions as an efficient nanocarrier for lipophilic drug delivery.


Subject(s)
Curcumin , Emulsions , Melanoma, Experimental , Nanoparticles , Oleic Acid , Curcumin/administration & dosage , Curcumin/chemistry , Curcumin/pharmacology , Hydrogen-Ion Concentration , Cell Line, Tumor , Oleic Acid/chemistry , Animals , Mice , Melanoma, Experimental/drug therapy , Nanoparticles/chemistry , Drug Carriers/chemistry , Cell Survival/drug effects , Melanoma/drug therapy , Antineoplastic Agents/administration & dosage , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Drug Delivery Systems
16.
J Biotechnol ; 392: 118-127, 2024 Sep 10.
Article in English | MEDLINE | ID: mdl-38969178

ABSTRACT

This study aimed at Candida rugosa lipase immobilization on a low-cost and readily available support. Among agro-industrial crops, hemp tea waste was chosen as the carrier because it provides higher immobilization performance than hemp flower and leaf wastes. Support characterization by ATR-FTIR, SEM and elemental analysis and the optimization of the adsorption immobilization process were performed. The lipase adsorption immobilization was obtained by soaking the support with hexane under mild agitation for 2 h and a successively incubating the enzyme for 1 h at room temperature without removing the solvent. The esterification of oleic acid with n-decanol was tested in a solvent-free system by studying some parameters that influence the reaction, such as the substrates molar ratio, the lipase activity/oleic acid ratio, reaction temperature and the presence/absence of molecular sieves. The biocatalyst showed the ability to bring the esterification reaction to equilibrium under 60 min and good reusability (maintaining 60 % of its original activity after three successive esterification reactions) but low conversion (21 %) at the optimized conditions (40 °C, 1:2 substrates molar ratio, 0.56 lipase/oleic acid ratio, without sieves). Comparing the results with those obtained by free lipase form at the same activity (1 U) and experimental conditions, slightly higher conversion (%) appeared for the free lipase. All this highlighted that probably the source of lipase for its carbohydrate-binding pocket and lid structure affected the esterification of oleic acid but certainly, the immobilization didn't induce any lipase conformational change also allowing the reuse of the catalytic material.


Subject(s)
Cannabis , Enzymes, Immobilized , Lipase , Oleic Acid , Lipase/metabolism , Lipase/chemistry , Enzymes, Immobilized/metabolism , Enzymes, Immobilized/chemistry , Esterification , Oleic Acid/chemistry , Oleic Acid/metabolism , Cannabis/enzymology , Cannabis/chemistry , Cannabis/metabolism , Solvents/chemistry , Candida/enzymology , Saccharomycetales
17.
Phytochemistry ; 226: 114209, 2024 Oct.
Article in English | MEDLINE | ID: mdl-38972439

ABSTRACT

Seven undescribed benzoate glycosides (1-7) and five known ones (8-12) were isolated from the rhizomes of Gentiana scabra Bge. Their structures were characterized by comprehensive NMR and MS spectroscopic data analysis. The lipid-lowering effects of these compounds were evaluated by measuring the triglyceride (TG) contents and intracellular lipid droplets (LDs) in oleic acid (OA)-treated HepG2 cells. The results showed that compounds 1, 5, 7, and 11 significantly reduced the TG content at 20 µM, and the Bodipy staining displayed that OA enhanced the levels of LDs in the cell, while these compounds reversed the lipid accumulation caused by OA. These findings provide a basis for further development and utilization of G. scabra as a natural source of potential lipid-lowering agents.


Subject(s)
Gentiana , Glycosides , Hypolipidemic Agents , Glycosides/pharmacology , Glycosides/chemistry , Glycosides/isolation & purification , Humans , Gentiana/chemistry , Hep G2 Cells , Hypolipidemic Agents/pharmacology , Hypolipidemic Agents/chemistry , Hypolipidemic Agents/isolation & purification , Benzoates/pharmacology , Benzoates/chemistry , Benzoates/isolation & purification , Molecular Structure , Oleic Acid/pharmacology , Oleic Acid/chemistry , Structure-Activity Relationship , Dose-Response Relationship, Drug , Triglycerides , Rhizome/chemistry
18.
BMC Plant Biol ; 24(1): 733, 2024 Jul 31.
Article in English | MEDLINE | ID: mdl-39085764

ABSTRACT

BACKGROUND: Improving the quality and shelf life of groundnut oil is one of the foremost objectives of groundnut breeding programmes. This can be achieved by marker-assisted introgression, a technique that efficiently and precisely enables breeders to develop plants with enhanced qualities. This study focused on improving the oleic acid content of an elite groundnut variety, TMV 7, by introgressing a recessive mutation responsible for the increase in oleic acid from ICG 15419. Hybridization was performed between the donor and recurrent parents to develop the F1, BC1F1, BC2F1 and BC2F2 populations. Introgressed lines with increased oleic acid in the genetic background of TMV 7 were identified using allele-specific marker, F435-F, F435SUB-R and a set of SSR markers were employed to recover the genome of the recurrent parent. RESULTS: With two backcrosses, a total of ten homozygous plants in the BC2F2 population were identified with oleic acid content ranging from 54.23 to 57.72% causing an increase of 36% over the recurrent parent. Among the ten lines, the line IL-23 exhibited the highest level of recurrent parent genome recovery of 91.12%. CONCLUSIONS: The phenotypic evaluation of 10 homozygous introgressed lines indicated fewer differences for all other traits under study compared to the recurrent parent, except for oleic acid and linoleic acid content confirming the genetic background of the recurrent parent. The identified lines will be subjected to multilocation trials before their commercial release.


Subject(s)
Arachis , Oleic Acid , Plant Breeding , Oleic Acid/metabolism , Arachis/genetics , Arachis/metabolism , Plant Breeding/methods , Genetic Markers , Genetic Introgression , Plant Oils/metabolism
19.
J Oleo Sci ; 73(8): 1083-1090, 2024 Aug 01.
Article in English | MEDLINE | ID: mdl-39019618

ABSTRACT

Growing evidence indicates that the intake of trans fatty acids (TFAs) increases the risk of numerous diseases, such as cardiovascular diseases. Recently, our group found that certain natural sulfur compounds (allyl isothiocyanate [AITC] and diallyl disulfide [DADS]) promote cis to trans isomerization of fatty acid esters during heat treatment. However, little information is available on the fatty acid isomerization with them. In this study, we investigated the effects of oxygen and α-tocopherol (antioxidant) on isomerization of oleic acid (18:1) methyl ester (OA-ME) in the presence of AITC and DADS. Furthermore, the effect of the simultaneous use of AITC and DADS was evaluated. Our results indicate that oxygen enhances the AITC-induced trans isomerization, and DADS was found to promote trans isomerization but inhibit AITC-induced trans isomerization during heating. Both AITC- and DADS-induced trans isomerization were inhibited by α-tocopherol. These results indicate that the trans isomerization of fatty acids induced by sulfur compounds can be controlled by devising a cooking process and the food ingredients used together.


Subject(s)
Disulfides , Isothiocyanates , Oleic Acids , alpha-Tocopherol , Isomerism , alpha-Tocopherol/chemistry , Disulfides/chemistry , Oleic Acids/chemistry , Isothiocyanates/chemistry , Allyl Compounds/chemistry , Oxygen/chemistry , Antioxidants/chemistry , Hot Temperature , Sulfur Compounds/chemistry , Cooking , Oleic Acid/chemistry , Trans Fatty Acids/chemistry , Esters/chemistry , Stereoisomerism , Cysteine/analogs & derivatives
20.
Acta Biochim Pol ; 71: 13014, 2024.
Article in English | MEDLINE | ID: mdl-39027262

ABSTRACT

Fatty acid profiles are crucial for the functionality and viability of lactobacilli used in food applications. Tween 80™, a common culture media additive, is known to influence bacterial growth and composition. This study investigated how Tween 80™ supplementation impacts the fatty acid profiles of six mesophilic lactobacilli strains (Lacticaseibacillus spp., Limosilactobacillus spp., Lactiplantibacillus plantarum). Analysis of eleven strains revealed 29 distinct fatty acids. Tween 80™ supplementation significantly altered their fatty acid composition. Notably, there was a shift towards saturated fatty acids and changes within the unsaturated fatty acid profile. While some unsaturated fatty acids decreased, there was a concurrent rise in cyclic derivatives like lactobacillic acid (derived from vaccenic acid) and dihydrosterculic acid (derived from oleic acid). This suggests that despite the presence of Tween 80™ as an oleic acid source, lactobacilli prioritize the synthesis of these cyclic derivatives from precursor unsaturated fatty acids. Myristic acid and dihydrosterculic acid levels varied across strains. Interestingly, palmitic acid content increased, potentially reflecting enhanced incorporation of oleic acid from Tween 80™ into membranes. Conversely, cis-vaccenic acid levels consistently decreased across all strains. The observed fatty acid profiles differed from previous studies, likely due to a combination of factors including strain-specific variations and growth condition differences (media type, temperature, harvesting point). However, this study highlights the consistent impact of Tween 80™ on the fatty acid composition of lactobacilli, regardless of these variations. In conclusion, Tween 80™ significantly alters fatty acid profiles, influencing saturation levels and specific fatty acid proportions. This work reveals key factors, including stimulated synthesis of lactobacillic acid, competition for oleic acid incorporation, and strain-specific responses to myristic and dihydrosterculic acids. The consistent reduction in cis-vaccenic acid and the presence of cyclic derivatives warrant further investigation to elucidate their roles in response to Tween 80™ supplementation.


Subject(s)
Fatty Acids , Lactobacillus , Polysorbates , Polysorbates/pharmacology , Fatty Acids/metabolism , Lactobacillus/metabolism , Oleic Acids/metabolism , Myristic Acid/metabolism , Oleic Acid/metabolism , Culture Media/chemistry , Palmitic Acid/metabolism , Fatty Acids, Unsaturated/metabolism
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