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1.
Chem Commun (Camb) ; 56(9): 1353-1356, 2020 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-31904054

RESUMO

A novel cyclodextrin molecular tube with one fully modified and one unmodified end was facilely synthesized by selective desilylation of a 6-O-tert-butyldimethylsilylated ß-cyclodextrin dimer possessing multiple linkers. This molecular tube showed a selective inclusion ability toward cis-unsaturated fatty acid esters by utilizing the asymmetric cylindrical nanocavity.


Assuntos
Ésteres/química , Ácidos Graxos Insaturados/química , beta-Ciclodextrinas/química , Estrutura Molecular , Estereoisomerismo , beta-Ciclodextrinas/síntese química
2.
Chem Asian J ; 15(1): 42-50, 2020 Jan 02.
Artigo em Inglês | MEDLINE | ID: mdl-31782616

RESUMO

Polyunsaturated fatty acids are sources of diverse natural, and chemically designed products. The enzyme lipoxygenase selectively oxidizes fatty acid acyl chains using controlled free radical chemistry; the products are regio- and stereo-chemically unique hydroperoxides. A conserved structural fold of ≈600 amino acids harbors a long and narrow substrate channel and a well-shielded catalytic iron. Oxygen, a co-substrate, is blocked from the active site until a hydrogen atom is abstracted from substrate bis-allylic carbon, in a non-heme iron redox cycle. EPR spectroscopy of ferric intermediates in lipoxygenase catalysis reveals changes in the metal coordination and leads to a proposal on the nature of the reactive intermediate. Remarkably, free radicals are so well controlled in lipoxygenase chemistry that spin label technology can be applied as well. The current level of understanding of steps in lipoxygenase catalysis, from the EPR perspective, will be reviewed.


Assuntos
Ácidos Graxos Insaturados/metabolismo , Lipoxigenases/metabolismo , Biocatálise , Espectroscopia de Ressonância de Spin Eletrônica , Ácidos Graxos Insaturados/química , Humanos , Estrutura Molecular
4.
J Agric Food Chem ; 67(43): 11931-11941, 2019 Oct 30.
Artigo em Inglês | MEDLINE | ID: mdl-31589419

RESUMO

Lipid-based delivery systems (LBDSs) are widely applied in pharmaceuticals and health care because of the increased bioavailability of lipophilic components when they are coadministered with high-fat meals. However, how to accurately control their in vivo release and stability is still challenging. Here, after introducing the simple esterification and coprecipitation, we created the dual-functional composite ODS-ß-CD-VE by the coassembly of ß-cyclodextrin (ß-CD), octadecenyl succinic anhydride (ODSA), and vitamin E (VE). The resulting dual-functional particle presented a uniform sheetlike shape and nanometer size. In addition, its chemical structure was clarified in detail via nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FTIR), and X-ray diffraction (XRD). Benefiting from the antioxygenation of VE, lipid oxidation in the ODS-ß-CD-VE-stabilized Pickering emulsion was effectively inhibited. Meanwhile, pH-induced protonation/deprotonation of carboxyl groups guaranteed that the emulsions kept steady at pH ≤4 but were unsteady under neutral conditions. In this way, the lipids contained in the emulsion were protected from gastric juice and then digested and accurately released as n-3 polyunsaturated fatty acids (PUFA) in the simulated intestine environment. This strategy sheds some light on the rational and efficient construction of LBDSs for nutrient supplements and even pharmaceuticals in a living digestive tract.


Assuntos
Preparações de Ação Retardada/química , Ácidos Graxos Insaturados/química , Vitamina E/química , beta-Ciclodextrinas/química , Preparações de Ação Retardada/metabolismo , Digestão , Emulsões/química , Ácidos Graxos Insaturados/metabolismo , Trato Gastrointestinal/metabolismo , Humanos , Concentração de Íons de Hidrogênio , Modelos Biológicos
5.
Anal Chim Acta ; 1086: 82-89, 2019 Dec 04.
Artigo em Inglês | MEDLINE | ID: mdl-31561797

RESUMO

The location of double bond in unsaturated fatty acids (FAs) plays a critical role in their physiological properties. However, structural identification and quantification of unsaturated FAs by mass spectrometry are still challenging. In this work, we reported the coupling of epoxidation reaction of the C=C in unsaturated FAs and liquid chromatography-mass spectrometry (LC-MS) with multiple reaction monitoring (MRM) mode for accurate identification and quantification of C=C isomers of FAs. Epoxidation of the C=C in unsaturated FAs was induced by a dioxide of ketone, tetrahydrothiopyran-4-one 1,1-dioxide, as a catalyst and Oxone as an oxidant in less than 5 min with nearly 100% yield. All the C=C bonds were epoxidized to obtain a single product, simplifying the chromatographic separation of epoxidation products to enable more accurate quantification analysis. The epoxidation products were stable at room temperature and can produce highly abundant diagnostic ions indicative of C=C locations by tandem mass spectrometry using collision-induced association (CID). The application of this approach for the analysis of FAs isomers in human plasma demonstrated the potential of our method for the qualitative and quantitative analysis of unsaturated FAs in complex biological samples, which is valuable in biological and medical analysis.


Assuntos
Compostos de Epóxi/química , Ácidos Graxos Insaturados/sangue , Ácidos Graxos Insaturados/química , Cromatografia Líquida de Alta Pressão , Voluntários Saudáveis , Humanos , Espectrometria de Massas , Estrutura Molecular , Estereoisomerismo
6.
Analyst ; 144(19): 5848-5855, 2019 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-31482871

RESUMO

The carbon-carbon double bond positions of unsaturated fatty acids can have markedly different effects on biological function and also serve as biomarkers of disease pathology, dietary history, and species identity. As such, there is great interest in developing methods for the facile determination of double bond position for natural product chemistry, the pharmaceutical industry, and forensics. We paired ozonolysis with direct analysis in real time mass spectrometry (DART MS) to cleave and rapidly identify carbon-carbon double bond position in fatty acids, fatty alcohols, wax esters, and crude fatty acid extracts. In addition, ozone exposure time and DART ion source temperature were investigated to identify optimal conditions. Our results reveal that brief, offline exposure to ozone-generated aldehyde and carboxylate products that are indicative of carbon-carbon double bond position. The relative abundance of diagnostic fragments quantitatively reflects the ratios of isobaric fatty acid positional isomers in a mixture with a correlation coefficient of 0.99. Lastly, the unsaturation profile generated from unfractionated, fatty acid extracts can be used to differentiate insect species and populations. The ability to rapidly elucidate lipid double bond position by combining ozonolysis with DART MS will be useful for lipid structural elucidation, assessing isobaric purity, and potentially distinguishing between animals fed on different diets or belonging to different ecological populations.


Assuntos
Ácidos Graxos Insaturados/química , Ozônio/química , Animais , Drosophila/química , Drosophila/classificação , Álcoois Graxos/química , Isomerismo , Espectrometria de Massas/métodos , Ceras/química
7.
J Dairy Sci ; 102(11): 9870-9882, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31447159

RESUMO

Effects of culture pH and corn oil (CO) concentration on biohydrogenation (BH) of unsaturated fatty acids and disappearance of neutral detergent fiber (NDF) in batch culture were evaluated in a 2 × 3 factorial design experiment. Culture vessels (100 mL; 4 replicates/treatment per time point) included ground alfalfa hay plus CO at 0, 1, or 2% dry matter inclusion rate and were incubated at pH 5.8 (low pH) or 6.2 (high pH) for 0, 6, 12, 18, or 24 h. Effects of culture pH, CO, time, and their interactions were determined. Adding CO increased total fatty acid concentration in substrates to 1.01, 2.31, and 3.58% dry matter for 0, 1, and 2% CO, respectively. Corn oil concentration interacted with culture pH and resulted in different effects on BH of cis-9,cis-12 18:2 at low or high culture pH. After 24 h of incubation, low pH, compared with high pH, reduced disappearance of NDF by 35% and BH extent of cis-9,cis-12 18:2 by 31%. Increasing CO increased disappearance of NDF across pH treatments and decreased BH extent of cis-9,cis-12 18:2 at low pH and increased it at high pH over 24 h. Compared with high pH, low pH reduced concentrations of 18:0 by 31% and increased concentrations of trans-10,cis-12 18:2 and trans-10 18:1 by 110 and 79% after 24 h, respectively. Adding CO at low pH had greater effect on BH intermediates of cis-9,cis-12 18:2 compared with adding oil at high pH. In particular, increasing CO to 1 and 2% DM at low pH, compared with at high pH, resulted in a 36 and 46% reduction in the concentration of 18:0, an 84 and 131% increase in the concentration of trans-10,cis-12 18:2, and an 81 and 129% increase in the concentration of trans-10 18:1, respectively. Despite the interactions between culture pH and CO concentration, main effects across time were also significant for the response variables of interest. In conclusion, culture pH interacted with CO concentration to affect BH of UFA and disappearance of NDF in batch culture, as the effects were greater at low culture pH than at high culture pH.


Assuntos
Óleo de Milho/química , Fibras na Dieta/metabolismo , Ácidos Graxos Insaturados/química , Ácidos Graxos/química , Leite/química , Ração Animal/análise , Animais , Bovinos/fisiologia , Dieta/veterinária , Suplementos Nutricionais/análise , Feminino , Concentração de Íons de Hidrogênio , Hidrogenação , Lactação , Leite/metabolismo , Rúmen/metabolismo , Rúmen/microbiologia
8.
J Chem Ecol ; 45(8): 649-656, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31407197

RESUMO

Pheromone-baited traps can be excellent tools for sensitive detection of insects of conservation concern. Here, identification of the sex pheromone of Trichopteryx polycommata (Denis & Schiffermüller, 1775), an under-recorded UK priority species, is reported. In analyses of extracts of the pheromone glands of female T. polycommata by gas chromatography coupled to electroantennographic recording from the antenna of a male moth, a single active component was detected. This was identified as (Z,Z)-6,9-nonadecadiene (Z,Z6,9-19:H) by comparison of its mass spectrum and retention times with those of the synthetic standard. In a pilot field trial in Kent, UK, T. polycommata males were caught in pheromone traps baited with lures loaded with 1 mg and 2 mg (Z,Z)-6,9-19:H. Optimum lure loading was identified in a further five trials in Kent, Sussex and Lancashire where lures of 0, 0.001, 0.01, 0.1, 1, 2, 5 and 10 mg loadings were tested. Traps baited with 1 to 10 mg of ZZ6,9-19:H caught significantly more T. polycommata than traps baited with 0 mg and 0.001 mg. In a pilot survey of T. polycommata using pheromone lures around Morecambe Bay, UK, T. polycommata males were captured at 122 new sites within the three counties where trials took place, demonstrating the potential of pheromone monitoring to increase knowledge of abundance, distribution and ecology of this elusive species.


Assuntos
Mariposas/fisiologia , Atrativos Sexuais/química , Animais , Espécies em Perigo de Extinção , Ácidos Graxos Insaturados/química , Ácidos Graxos Insaturados/farmacologia , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Masculino , Feromônios/química , Feromônios/farmacologia , Atrativos Sexuais/farmacologia , Comportamento Sexual Animal/efeitos dos fármacos
9.
J Agric Food Chem ; 67(33): 9423-9431, 2019 Aug 21.
Artigo em Inglês | MEDLINE | ID: mdl-31329442

RESUMO

A high-throughput lipid analysis method was established to comprehensively investigate the lipid profiles of three marine (Scomberomorus niphonius, Scophthalmus maximus, and Oncorhynchus keta) and one freshwater (Ctenopharyngodon idellus) fish species using ultraperformance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. Over 700 molecular species from 12 major lipid subclasses were identified. Glycerolipids (73.7-85.6%) and phospholipids (PLs, 13.7-25.6%) were dominant components in total lipids. Polyunsaturated fatty acid PLs, such as phosphatidylethanolamine (PE, 16:0-22:6), PE (18:1-22:6), and phosphatidylcholine (16:0-22:6), were the major molecular species in PLs. The lipid composition of three marine fish (mainly C22:5) was significantly different from that in C. idellus (mainly C20:4 and C20:5). A unique long-chain base of sphingolipids was found in fish (mainly d19:3). These bioactive lipids were proposed to be potential biomarkers for distinguishing different fish species and evaluating nutritional values.


Assuntos
Lipídeos/química , Alimentos Marinhos/análise , Animais , Cromatografia Líquida de Alta Pressão , Cyprinidae , Ácidos Graxos Insaturados/química , Linguados , Espectrometria de Massas , Oncorhynchus keta , Fosfatidiletanolaminas/química , Fosfolipídeos/química , Atum
10.
Nutrients ; 11(7)2019 Jul 13.
Artigo em Inglês | MEDLINE | ID: mdl-31337035

RESUMO

Study objectives were to determine if erythrocyte omega-3 polyunsaturated fatty acids (n-3 PUFAs) increased in women participating in a dietary intervention that reduced inflammation and body weight and examine PUFA associations with markers of inflammation and quality of life (QOL). An experimental pre-post test, single group design was used. Fifteen post-menopausal women with obesity were enrolled in a 12-week pilot intervention focusing on lowering added sugars and increasing fiber and fish rich in n-3 PUFAs. Measurements included fasting blood samples, anthropometric, lifestyle and dietary data collected at baseline, end of intervention (Week 12) and follow-up (Week 24). Primary outcomes were change in erythrocyte PUFAs and associations between erythrocyte PUFAs, QOL (Short Form 12), and inflammatory markers (interleukin-6, tumor necrosis factor-α-receptor 2, and high sensitivity C-reactive protein (CRP)). Fourteen women completed all intervention visits. Mean erythrocyte docosahexaenoic acid and arachidonic acid (AA) increased at Week 12 and Week 24 (p < 0.001 for both), while eicosapentaenoic acid increased at Week 24 (p < 0.01). After adjustment for percent weight change, week 12 QOL related to physical function was significantly associated with erythrocyte linoleic acid (p < 0.05) and trended toward significant association with EPA (p = 0.051); week 24 CRP was directly associated with erythrocyte AA (p < 0.05). Erythrocyte n-3 PUFAs were not associated with inflammation.


Assuntos
Dieta Redutora , Eritrócitos/química , Ácidos Graxos Insaturados/química , Inflamação/metabolismo , Obesidade/metabolismo , Pós-Menopausa , Adulto , Feminino , Humanos , Projetos Piloto , Qualidade de Vida
11.
Biochim Biophys Acta Biomembr ; 1861(8): 1428-1436, 2019 08 01.
Artigo em Inglês | MEDLINE | ID: mdl-31189076

RESUMO

Unsaturated fatty acids (UFAs) are known to lower the level of sterols in blood, which accounts for their cardioprotective effect. To understand the molecular basis of this effect, Langmuir monolayer studies have been performed. A series of UFAs differing in the length of the fatty acid chain and the number of double bonds (oleic acid, OA; linoleic acid, LA; stearidonic acid, SDA; eicosanoic acid, EA) were mixed with cholesterol and its more toxic oxidized derivative, 7­ketocholesterol (7-KC), abundantly present in atheroma plaques. Strong attractive UFA-sterol interactions were attributed to the formation of "surface complexes", in which sterol molecules are bound, thereby reducing the amount of free sterol molecules. It has been found that strength of interactions increases with the degree of unsaturation of the acyl chain in UFA molecule. The most attractive interactions correspond to mixtures with SDA containing 70 mol% of 7-KC and 50 mol% of cholesterol. In both cases, the formation of high stability complexes of, respectively, 2:1 and 1:1 sterol/SDA stoichiometry has been proposed. Other complexes of lower stability and 1:2 stoichiometry were postulated for chol (or 7-KC)/LA systems. The complexes of the lowest stability correspond to chol (or 7-KC) mixtures with OA and EA of 1:1 stoichiometry. In all the cases, the interactions of 7-KC with UFAs are more energetically favorable versus cholesterol. The elongation of the hydrophobic chain of UFAs decreased the interactions with the studied sterols. The obtained results can be related to different conformations of the fatty acids chains.


Assuntos
Colesterol/química , Ácidos Graxos Insaturados/química , Cetocolesteróis/química , Propriedades de Superfície , Termodinâmica
12.
Anal Chim Acta ; 1075: 120-127, 2019 Oct 10.
Artigo em Inglês | MEDLINE | ID: mdl-31196417

RESUMO

In situ identification and quantification of unsaturated fatty acid (FA) C=C positional isomers in human serum is herein performed by negative-ion paper spray (PS) mass spectrometry. Typically, by direct application of an alternating current (AC) voltage to the wet paper, the PS ionization could perform stably in the negative-ion mode without severe discharge. We suppose epoxidation reaction between unsaturated C=C bonds and reactive oxidative species might be initiated by a mild electrical discharge, which could be rapidly and controllably produced via a low amplitude AC voltage. Upon collision-induce dissociation (CID), the epoxide was fragmented to generate diagnostic ions indicating the C=C location. The intensity of the characteristic product ions could also be used for absolute quantification of the FA C=C positional isomers. The limits of detection (LODs) and limits of quantification (LOQs) were roughly in the range of 0.0178-0.0506 µM and 0.0218-0.3634 µM for standard FAs. Without the additional sample preparations or reactive chemical reagents, epoxidation of unsaturated FAs and ionization of the epoxide could be achieved in one-step by negative-ion mode PS, which enable a promising methodology for on-site clinical diagnosis.


Assuntos
Ácidos Graxos Insaturados/sangue , Fontes de Energia Elétrica , Técnicas Eletroquímicas/instrumentação , Técnicas Eletroquímicas/métodos , Compostos de Epóxi/síntese química , Desenho de Equipamento , Ácidos Graxos Insaturados/química , Humanos , Limite de Detecção , Papel , Reprodutibilidade dos Testes , Espectrometria de Massas por Ionização por Electrospray/instrumentação , Espectrometria de Massas por Ionização por Electrospray/métodos
13.
J Oleo Sci ; 68(7): 625-635, 2019 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-31178462

RESUMO

The seed of five fruits and vegetables, which are often eaten by Chinese people, were selected as research objects to study the physicochemical properties, nutritional ingredients and antioxidant capacity of their seed oils. The fatty acid results indicated that the oleic acid was the main unsaturated fatty acid in almond oil and celery seed oil (content of 64.10% and 62.96%, respectively), and the wax gourd seed oil, watermelon seed oil and pumpkin seed oil were linoleic acid as the main unsaturated fatty acid (content of 72.45%, 76.77% and 47.35%, respectively). Unsaturated fatty acids are mainly located at the sn-2 position of the triacylglycerol (TAG), whereas saturated fatty acids are mainly located at the sn-1, 3 positions for the five seed oils. The pumpkin seed oil had certain advantages in terms of phytosterols and squalene (3716 and 2732 mg/kg, respectively). The high content of polyphenol for celery seed oil exhibits higher medicinal value. Polyphenols, and brassicasterols were have significant correlation with antioxidant capacity (p < 0.05, r = 0.890-0.998). The significant differences in nutrient composition between these fruits and vegetables seed oils indicate their unique value as food.


Assuntos
Antioxidantes , Frutas/química , Óleos Vegetais/química , Óleos Vegetais/farmacologia , Verduras/química , Fenômenos Químicos , China , Colestadienóis , Ácidos Graxos/análise , Ácidos Graxos/química , Ácidos Graxos/isolamento & purificação , Ácidos Graxos Insaturados/análise , Ácidos Graxos Insaturados/química , Ácidos Graxos Insaturados/isolamento & purificação , Ácidos Linoleicos/análise , Ácidos Linoleicos/isolamento & purificação , Ácido Oleico/análise , Ácido Oleico/isolamento & purificação , Fitosteróis , Polifenóis/análise , Polifenóis/isolamento & purificação , Esqualeno , Triglicerídeos/química
14.
Biol Pharm Bull ; 42(6): 937-943, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31155590

RESUMO

Hydroxyoctadecadienoic acids (HODEs) are generated by oxidation of linoleic acid in vivo and thought to mediate various pathophysiological responses. In this study, we examined the effects of HODEs on EL4 mouse lymphoma cell growth and found that 9-(E,Z)-HODE inhibited EL4 cell growth in a dose-dependent manner, whereas no such growth inhibition was observed with other isomers (9-(E,E)-, 13-(Z,E)-, or 13-(E,E)-HODE), suggesting that the growth-inhibitory effect of HODEs was stereospecific. Analysis by flow cytometry (FACS) with annexin V and propidium iodide (PI) staining showed that 9-(E,Z)-HODE induced apoptosis with G2/M phase arrest. We next examined the growth inhibition profile of 9-(E,Z)-HODE against a panel of 39 human cancer cell lines (JFCR39). The fingerprint of growth inhibition by 9-(E,Z)-HODE exhibited a high degree of similarity to that by MLN4924, an inhibitor of NEDD8-activating enzyme. The intracellular NEDD8 (ubiquitin-like protein) expression in EL4 cells was decreased by the treatment with 9-(E,Z)-HODE as assessed by immunoblotting and flow cytometry. In conclusion, 9-(E,Z)-HODE specifically induced G2/M phase arrest and apoptosis, and the decrease of NEDD8 expression might be involved in this effect.


Assuntos
Apoptose/efeitos dos fármacos , Ciclo Celular/efeitos dos fármacos , Ácidos Graxos Insaturados/farmacologia , Linfoma/metabolismo , Animais , Linhagem Celular Tumoral , Ácidos Graxos Insaturados/química , Linfoma/patologia , Camundongos , Proteína NEDD8/metabolismo , Estereoisomerismo
15.
J Food Sci ; 84(7): 1799-1805, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31218694

RESUMO

Defatting of seabass skins using pulsed electric field (PEF)-assisted process at different electric field strengths (16 and 24 kV/cm) and times (36, 72, and 108 ms) in combination with porcine pancreas lipase (PPL) at 25 U/g dry matter was investigated. PEF-treated skin at 24 kV/cm for 72 ms followed by PPL treatment removed 86.93% lipids. PEF-treated skin was further optimized for lipid reduction by response surface methodology. Central composite design was adopted to establish treatments based on two independent variables, involving PPL concentration (30 to 55 U/g dry matter) and hydrolysis time (60 to 180 min). Second-order polynomial model was used for predicting the response. The highest lipid removal (91.96 ± 1.70%) was attained when the optimal condition (42.36 PPL units/g dry skin matter for 139.78 min) was used. The experiment value was in accordance with the predicted value. PEF-PPL-treated skin had lower monounsaturated and polyunsaturated fatty acids than the solvent-extracted skin (P < 0.05). When PEF-PPL-treated skin was hydrolyzed using papain at 0.30 U/g dry matter, lower fishy odor/flavor of resulting hydrolyzed collagen (PEF-PPL-HC) was found than other samples (P < 0.05). Lower total volatile compounds were also obtained in PEF-PPL-HC sample. Thus, the use of PEF pretreatment along with PPL before papain hydrolysis effectively prevented the formation of fishy odor/flavor in hydrolyzed collagen from seabass skin. PRACTICAL APPLICATION: Fishy odor/flavor caused by lipid oxidation of fish skin hydrolysates limits their applications in foods. Defatting process is the significant step for skin pretreatment. Although several methods could remove lipids from fish skins, either by lipase or solvent extraction, fishy odor/flavor is still detected in hydrolysate. Pulsed electric field-assisted process in combination with porcine lipase is another approach that can be used to enhance efficiency via electroporation, causing the loosened skin matrix and facilitating the migration of lipase into the skin. Consequently, the resulting hydrolysate might have the lowered fishy odor/flavor and could be used in foods, especially for fortification.


Assuntos
Manipulação de Alimentos/métodos , Lipase/química , Lipídeos/química , Pele/química , Animais , Bass , Biocatálise , Colágeno/química , Ácidos Graxos Insaturados/química , Proteínas de Peixes/química , Manipulação de Alimentos/instrumentação , Humanos , Odorantes/análise , Oxirredução , Suínos , Paladar
16.
Drug Dev Ind Pharm ; 45(9): 1451-1458, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31216907

RESUMO

Objective: The aim of this study was to develop a coenzyme Q10 nanoemulsion cream, characterize and to determine the influence of omega fatty acids on the delivery of coenzyme Q10 across model skin membrane via ex vivo and in silico techniques. Methods: Coenzyme Q10 nanoemulsion creams were prepared using natural edible oils such as linseed, evening primrose, and olive oil. Their mechanical features and ability to deliver CoQ10 across rat skin were characterized. Computational docking analysis was performed for in silico evaluation of CoQ10 and omega fatty acid interactions. Results: Linseed, evening primrose, and olive oils each produced nano-sized emulsion creams (343.93-409.86 nm) and exhibited excellent rheological features. The computerized docking studies showed favorable interactions between CoQ10 and omega fatty acids that could improve skin permeation. The three edible-oil nanoemulsion creams displayed higher ex vivo skin permeation and drug flux compared to the liquid-paraffin control cream. The linseed oil formulation displayed the highest skin permeation (3.97 ± 0.91 mg/cm2) and drug flux (0.19 ± 0.05 mg/cm2/h). Conclusion: CoQ10 loaded-linseed oil nanoemulsion cream displayed the highest skin permeation. The highest permeation showed by linseed oil nanoemulsion cream may be due to the presence of omega-3, -6, and -9 fatty acids which might serve as permeation enhancers. This indicated that the edible oil nanoemulsion creams have potential as drug vehicles that enhance CoQ10 delivery across skin.


Assuntos
Portadores de Fármacos/química , Ácidos Graxos Insaturados/química , Creme para a Pele/farmacocinética , Ubiquinona/análogos & derivados , Administração Cutânea , Animais , Simulação por Computador , Composição de Medicamentos , Emulsões , Nanopartículas/química , Permeabilidade , Ratos , Pele/efeitos dos fármacos , Pele/metabolismo , Absorção Cutânea , Creme para a Pele/administração & dosagem , Ubiquinona/administração & dosagem , Ubiquinona/farmacocinética
17.
Food Chem ; 295: 423-431, 2019 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-31174778

RESUMO

Effects of natural phenolics on the shelf life of dried scallop adductor muscle predicted by accelerated shelf life testing (ALST) combined with Arrhenius model were investigated. This allows the food industries to reliably and rapidly determine the shelf life of dried shellfish species treated with antioxidants. The shelf life of dried scallop adductor muscle treated with antioxidants of bamboo leaves (AOB) and tea polyphenols (TP) was more than 1.70-fold that of dried control scallop adductor muscle. Thus, the highly nutritional value of dried scallop adductor muscle, based on its lipid constituents, is maintained during storage. OXITEST method further confirmed the improvement of lipid stability of antioxidant treated dried scallop adductor muscle by protecting polyunsaturated fatty acids, especially eicosapentaenoic and docosahexaenoic acids, against autoxidation. Moreover, the natural phenolics employed effectively limited lipid oxidation by breaking the autoxidative chain reaction and/or inhibiting free radical formation in dried scallop adductor muscle during storage.


Assuntos
Armazenamento de Alimentos , Lipídeos/química , Pectinidae/química , Polifenóis/química , Frutos do Mar , Animais , Antioxidantes/química , Camellia sinensis/química , Ácidos Graxos Insaturados/análise , Ácidos Graxos Insaturados/química , Liofilização , Músculo Esquelético/química , Valor Nutritivo , Oxirredução , Folhas de Planta/química , Carbamilação de Proteínas , Sasa/química
18.
PLoS One ; 14(5): e0217047, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31107897

RESUMO

Phytoplankton are the oceans' principal source of polyunsaturated fatty acids that support the growth and reproduction of consumers such as copepods. Previous studies have demonstrated ocean acidification (OA) can change the availability of polyunsaturated fatty acids to consumer diets which may affect consumer reproduction. Two laboratory experiments were conducted to examine the effects of feeding high-pCO2-reared phytoplankton on copepod egg production, hatching success, and naupliar survival. Marine phytoplankton Rhodomonas salina, Skeletonema marinoi, Prorocentrum micans, and Isochrysis galbana were exponentially grown in semi-continuous cultures at present (control) (400 ppm CO2, pH~8.1) and future (1,000 ppm CO2, pH~7.8) conditions and provided to Acartia tonsa copepods over 4 consecutive days as either nitrogen-limited (Exp. I) or nitrogen-depleted (Exp. II) mixed assemblage of phytoplankton. The composition of FAs in the phytoplankton diet was affected by pCO2 concentration and nitrogen deficiency; the ratio of essential fatty acids to total polyunsaturated fatty acids decreased in phytoplankton grown under high pCO2 and the mass of total fatty acids increased under nitrogen depletion. Additionally, total concentrations of essential fatty acids and polyunsaturated fatty acids in the diet mixtures were less under the high-pCO2 compared to the control-pCO2 treatments. Median egg production, hatching success, and naupliar survival were 48-52%, 4-87%, and 9-100% lower, respectively, in females fed high-pCO2 than females fed low-pCO2 phytoplankton, but this decrease in reproductive success was less severe when fed N-depleted, but fatty acid-rich cells. This study demonstrates that the effects of OA on the nutritional quality of phytoplankton (i.e., their cellular fatty acid composition and quota) were modified by the level of nitrogen deficiency and the resulting negative reproductive response of marine primary consumers.


Assuntos
Copépodes/fisiologia , Oceanos e Mares , Fitoplâncton/fisiologia , Água do Mar/química , Ração Animal , Animais , Dióxido de Carbono/química , Diatomáceas/fisiologia , Ácidos Graxos Insaturados/química , Feminino , Concentração de Íons de Hidrogênio , Masculino , Nitrogênio/química , Valor Nutritivo , Reprodução
19.
J Oleo Sci ; 68(5): 399-408, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31061263

RESUMO

Coconut oil rich in medium-chain saturated fatty acids was enzymatically modified at the sn-2 position with polyunsaturated fatty acids from fish oil by trans-esterification reaction. The modified coconut oil was combined with gelators (γ-oryzanol and ß-sitosterol) to prepare organogels. The effects of different modified coconut oil contents and γ-oryzanol:ß-sitosterol ratios on thermodynamic and rheological properties, and microstructures of organogels, as well as their relationships, were studied. The results showed that the addition of gelators increased the hardness, solid fat content, and oil binding capacity of organogels. In addition to its highest melting point and enthalpy change, the organogel containing γ-oryzanol:ß-sitosterol (6:4) had the best texture properties that closely resemble the crystalline structure properties. Moreover, the developed organogels had the properties of a pseudoplastic fluid, as described by the power law equation. G' of organogel was found to be significantly higher than G'', which indicates that the organogel remains in solid state. The analysis of crystal morphology showed that the crystal of organogels were clusters, consisting of dense three-dimensional network of gel.


Assuntos
Óleo de Coco/química , Ácidos Graxos Insaturados/química , Fenômenos Químicos , Cristalização , Esterificação , Ácidos Graxos , Óleos de Peixe/química , Géis , Fenilpropionatos/química , Reologia , Sitosteroides/química , Termodinâmica
20.
Nucleic Acids Res ; 47(12): 6029-6044, 2019 07 09.
Artigo em Inglês | MEDLINE | ID: mdl-31127296

RESUMO

Enhancing the functional uptake of antisense oligonucleotide (ASO) in the muscle will be beneficial for developing ASO therapeutics targeting genes expressed in the muscle. We hypothesized that improving albumin binding will facilitate traversal of ASO from the blood compartment to the interstitium of the muscle tissues to enhance ASO functional uptake. We synthesized structurally diverse saturated and unsaturated fatty acid conjugated ASOs with a range of hydrophobicity. The binding affinity of ASO fatty acid conjugates to plasma proteins improved with fatty acid chain length and highest binding affinity was observed with ASO conjugates containing fatty acid chain length from 16 to 22 carbons. The degree of unsaturation or conformation of double bond appears to have no influence on protein binding or activity of ASO fatty acid conjugates. Activity of fatty acid ASO conjugates correlated with the affinity to albumin and the tightest albumin binder exhibited the highest activity improvement in muscle. Palmitic acid conjugation increases ASO plasma Cmax and improved delivery of ASO to interstitial space of mouse muscle. Conjugation of palmitic acid improved potency of DMPK, Cav3, CD36 and Malat-1 ASOs (3- to 7-fold) in mouse muscle. Our approach provides a foundation for developing more effective therapeutic ASOs for muscle disorders.


Assuntos
Músculo Esquelético/metabolismo , Miocárdio/metabolismo , Oligonucleotídeos Antissenso/química , Oligonucleotídeos Antissenso/farmacocinética , Ácido Palmítico/química , Animais , Proteínas Sanguíneas/metabolismo , Antígenos CD36/genética , Caveolina 3/genética , Ácidos Graxos/química , Ácidos Graxos Insaturados/química , Masculino , Camundongos Endogâmicos C57BL , Miotonina Proteína Quinase/genética , Oligonucleotídeos Antissenso/síntese química , Oligonucleotídeos Antissenso/metabolismo , RNA Longo não Codificante/metabolismo , Relação Estrutura-Atividade
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