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1.
Food Chem ; 447: 138979, 2024 Jul 30.
Artículo en Inglés | MEDLINE | ID: mdl-38518617

RESUMEN

Traditional Beijing roast duck often suffers from uneven color and high sugar content after roasting. Water-in-oil (W/O) nanoemulsion is a promising alternative to replace high concentration of sugar solution used in sugaring process according to similarity-intermiscibility theory. Herein, 3% of xylose was embedded in the aqueous phase of W/O emulsion to replace 15% maltose solution. W/O emulsions with different ratios of lecithin (LEC) and polyglycerol polyricinoleate (PGPR) were constructed by high-speed homogenization and high-pressure homogenization. Distribution and penetration extent of solutions and emulsions through the duck skin, as well as the color uniformity of Beijing roast duck were analyzed. Emulsions with LEC:PGPR ratios of 1:3 and 2:2 had better stability. Stable interfacial film and spatial structure were important factors influencing emulsion stabilization. The stable W/O emulsions could more uniformly distribute onto the surface of duck skin and longitudinally penetrate through the skin than solutions.


Asunto(s)
Patos , Glicerol/análogos & derivados , Lecitinas , Ácidos Ricinoleicos , Animales , Lecitinas/química , Emulsiones/química , Azúcares , Agua/química , Beijing
2.
Compr Rev Food Sci Food Saf ; 22(6): 4282-4301, 2023 11.
Artículo en Inglés | MEDLINE | ID: mdl-37583303

RESUMEN

Polyglycerol polyricinoleate (PGPR) is a synthetic food additive containing a complex mixture of various esters. In recent years, there has been a growing trend to use PGPR-stabilized water-in-oil (W/O) emulsions to replace fat in order to produce low-calorie food products. In this respect, it is essential to comprehensively characterize the PGPR molecular species composition, which might enable to reduce its required amount in emulsions and foods based on a better understanding of the structure-activity relationship. This review presents the recent research progress on the characterization and quantitative analysis of PGPR. The influencing factors of the emulsifying ability of PGPR in W/O emulsions are further illustrated to provide new insights on the total or partial replacement of PGPR. Moreover, the latest progress on applications of PGPR in food products is described. Current studies have revealed the complex structure of PGPR. Besides, recent research has focused on the quantitative determination of the composition of PGPR and the quantification of the PGPR concentration in foods. However, research on the quantitative determination of the (poly)glycerol composition of PGPR and of the individual molecular species present in PGPR is still limited. Some natural water- or oil-soluble surfactants (e.g., proteins or lecithin) have been proven to enable the partial replacement of PGPR in W/O emulsions. Additionally, water-dispersible phytosterol particles and lecithin have been successfully used as a substitute of PGPR to create stable W/O emulsions.


Asunto(s)
Glicerol , Lecitinas , Glicerol/química , Ácidos Ricinoleicos/química , Emulsiones/química , Agua/química
3.
Sci Rep ; 12(1): 11946, 2022 07 13.
Artículo en Inglés | MEDLINE | ID: mdl-35831366

RESUMEN

In this study, effects of sesamol on improving the oxidative stability of sunflower oil and its oil-in-water emulsion was investigated. To investigate the kinetic parameters related to the initiation and propagation stages of oxidation, a sigmoidal-model was used. Sesamol exhibited higher antioxidant activity in sunflower oil-in-water emulsion than that of sunflower oil. In both sunflower oil and sunflower oil-in-water emulsion, the inhibitory effect of sesamol against lipid oxidation continued even after the induction period. To improve the efficiency of sesamol in sunflower oil, polyglycerol polyricinoleate (PGPR) was incorporated into the functional environment of the sesamol. Sesamol exhibited a synergistic effect with PGPR during both initiation (synergistic effect of 68.87%) and propagation (synergistic effect of 36.84%) stages. Comparison of the size of reverse micelles in samples containing PGPR with those without PGPR revealed that PGPR can enhance the efficiency of sesamol by increasing the acceptance capacity of lipid hydroperoxides in reveres micelles structures. This can result in enhancing the effective collisions between sesamol and lipid hydroperoxides in the presence of PGPR. The water produced as a major byproduct of oxidation played a key role on the antioxidant activity of sesamol alone or in combination with PGPR during oxidation process.


Asunto(s)
Antioxidantes , Micelas , Antioxidantes/farmacología , Benzodioxoles , Emulsiones/química , Glicerol/análogos & derivados , Fenoles , Ácidos Ricinoleicos/química , Aceite de Girasol , Agua/química
4.
J Oleo Sci ; 71(6): 781-793, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-35661063

RESUMEN

Castor oil is a vegetable product extracted from Ricinus communis L (castor seed), which is primarily considered an important commercial value for the manufacturing of soaps, lubricants, coatings, etc. It is rich in hydroxylated fatty acids (ricinoleic acid, 89-92%) and is widely used in the cosmetic, pharmaceutical, oleochemical, and agricultural industries. This oil has also been confirmed as a bactericidal, anti-inflammatory, and antiherpetic agents, due to the ricinoleic acid having functional groups, such as -COOH, -OH, and -C=C-. Furthermore, it is converted into various acid derivative compounds with several applications. Therefore, this article reviewed some reaction stages to the preparation of ricinoleic acid from castor oil. Several methods or reaction pathways were employed in the preparation procedure, such as the Twitchell and Colgate-Emery processes, as well as the alkaline catalyzed, transesterification with methyl ricinoleic, and lipase-catalyzed hydrolysis, respectively. Although each of these preparation methods has advantages and disadvantages, the most effective technique was the hydrolysis through the use of the enzyme lipozyme TL IM. Besides being a green method, the conversion rate in the hydrolysis process was 96.2 ± 1.5.


Asunto(s)
Ácidos Ricinoleicos , Ricinus communis , Aceite de Ricino/química , Esterificación , Ácidos Grasos/metabolismo , Ácidos Ricinoleicos/metabolismo
5.
J Oleo Sci ; 71(6): 915-925, 2022.
Artículo en Inglés | MEDLINE | ID: mdl-35661069

RESUMEN

In this study, bio-based ionic liquid prepared from ricinoleic acid and choline was firstly used as additive in lithium base grease. The characterization and tribological performance of the prepared ionic liquid ([cho][ricinoleic]) as additive in grease were studied compared with the traditional ionic liquid such as L-P104. All the concentrations showed promising friction-reducing and anti-wear properties, though a 3% concentration has superior lubricating properties than others. Furthermore, [cho][ricinoleic]) can greatly enhance the lubrication capability of lithium base greaseunder different frequency and load at room temperature. Although L-P104 showed good lubricating performance than [cho][ricinoleic] at 150°C, the chosen formulation (1.5% [cho][ricinoleic] + 1.5% L-P104) could have better synergism at high and room temperature, which could be a good supplement to ionic liquid as grease additive. Thin films formed according to the results of SEM and XPS were attributed to be the main account for the preferable tribological properties of [cho][ricinoleic] in lithium base grease.


Asunto(s)
Líquidos Iónicos , Litio , Colina , Hidrocarburos , Lubricantes , Ácidos Ricinoleicos
6.
Int J Biol Macromol ; 186: 759-769, 2021 Sep 01.
Artículo en Inglés | MEDLINE | ID: mdl-34271051

RESUMEN

The present work aims to fabricate the genipin-crosslinked alkaline soluble polysaccharides-whey protein isolate conjugates (G-AWC) to stabilize W/O/W emulsions for encapsulation and delivery of grape seed proanthocyanidins (GSP). After crosslinking reaction, the molecular weight was increased and surface hydrophobicity was decreased. Then, the G-AWC and polyglycerol polyricinoleate (PGPR, a lipophilic emulsifier) were employed to prepare a GSP-loaded W/O/W emulsion with the addition of gelatin and sucrose in W1 phase via a two-step procedure. Creamed emulsion could be fabricated at W1/O volume fraction (Φ) of 10%-70% and further increased Φ to 75% or even up to 90% could obtain gel-like emulsion with notably elastic behaviors. In the W1/O/W2 emulsion with Φ of 80%, the encapsulation efficiency (EE) of GSP reached up to 95.86%, and decreased by ca. 10% after a week of storage. Moreover, the encapsulated GSP in the emulsion showed a remarkably higher bioaccessibility (40.72%) compared to free GSP (13.11%) in the simulated gastrointestinal digestion. These results indicated that G-AWC-stabilized W/O/W emulsions could be an effective carrier to encapsulate water-soluble bioactive compounds with enhanced stability and bioaccessibility.


Asunto(s)
Reactivos de Enlaces Cruzados/química , Digestión , Manipulación de Alimentos , Extracto de Semillas de Uva/química , Iridoides/química , Aceites/química , Polisacáridos/química , Proantocianidinas/química , Agua/química , Proteína de Suero de Leche/química , Disponibilidad Biológica , Emulsionantes/química , Emulsiones , Jugo Gástrico/química , Geles , Glicerol/análogos & derivados , Glicerol/química , Concentración de Iones de Hidrógeno , Secreciones Intestinales/química , Lipólisis , Ácidos Ricinoleicos/química , Solubilidad
7.
Food Chem ; 327: 127014, 2020 Oct 15.
Artículo en Inglés | MEDLINE | ID: mdl-32434126

RESUMEN

The influence of diacylglycerol (DAG) combined with polyglycerol polyricinoleate (PGPR) on the stability of water-in-oil (W/O) emulsions containing hydrogenated palm oil (HPO) was studied. Polarized light microscope revealed that DAG promoted HPO to crystallize at the water-oil interface, providing the combination of Pickering and network stabilization effects. It was proposed that the molecular compatibility of fatty acids in DAG with HPO accounted for the promotional effect. The interfacial crystallization of DAG together with the surface activity of PGPR led to the formation of emulsions with uniform small droplets and high freeze-thaw stability. Further exploration of physical properties indicated that the combination of DAG and PGPR dramatically improved the emulsion's viscoelasticity and obtained a larger deformation yield. Water droplets in DAG-based emulsions acted as active fillers to improve the network rigidity. Therefore, DAG is a promising material to be used as emulsifier to enhance the physical stability of W/O emulsions.


Asunto(s)
Diglicéridos/química , Emulsiones/química , Cristalización , Congelación , Glicerol/análogos & derivados , Glicerol/química , Aceite de Palma/química , Aceite de Brassica napus/química , Ácidos Ricinoleicos/química , Viscosidad , Agua/química
8.
Chirality ; 32(7): 998-1007, 2020 07.
Artículo en Inglés | MEDLINE | ID: mdl-32250002

RESUMEN

(R)-ricinoleic acid is the main component of castor oil from Ricinus communis L. Due to the presence of the hydroxyl group in homoallylic position and asymmetrically substituted carbon atom, it may undergo a number of chemical and biochemical transformations resulting in the products with some specific bioactivities. Conversion of (R)-ricinoleic acid into its (S)-enantiomer enables synthesis of both (R)- and (S)-ricinoleic acid derivatives and comparison of their biological activities. In the present research, (R)- and (S)-ricinoleic acid amides synthesized from methyl ricinoleates and ethanolamine or pyrrolidine as well as acetate derivatives of ethanolamine amides were studied to demonstrate their biological activities using HT29 cancer cells. Double staining of cells with fluorochromes (Hoechst 33258/propidium iodide) as well as 2,'7'-dichlorodihydrofluorescein (DCF) and comet assays were performed. Both the tested amides and acetates caused DNA damage and induced apoptotic and necrotic cell death. In the case of (R)- and (S)-enantiomers of one of the tested acetates, significant difference in the ability to induce DNA damage was observed, which showed the impact of the stereogenic center on the activities of these compounds.


Asunto(s)
Acetatos/química , Amidas/química , Antineoplásicos/farmacología , Aceite de Ricino/química , Ácidos Ricinoleicos/química , Antineoplásicos/química , Daño del ADN/efectos de los fármacos , Células HT29 , Humanos , Ácidos Ricinoleicos/toxicidad , Estereoisomerismo
9.
Lipids ; 55(5): 537-548, 2020 09.
Artículo en Inglés | MEDLINE | ID: mdl-32115716

RESUMEN

Castor oil contains approximately 90% ricinoleic acid (RA) which is stored mainly in the form of tri-ricinoleic acid containing triacylglycerols (TAG). Ricinoleate is synthesized from oleate (18:1n-9) esterified to the sn-2 position of phosphatidylcholine (PtdCho) catalyzed by oleoyl-12-hydroxylase. PtdCho-derived diacylglycerol (DAG) is an important substrate pool for TAG synthesis, and the interconversion between PtdCho and DAG has been shown to play a critical role in channeling hydroxy fatty acids (HFA) to TAG. Although phospholipase D (PLD) has been reported to catalyze the hydrolysis of PtdCho to produce phosphatidic acid which can then be converted to DAG, its potential functions in the channeling of RA from PtdCho to DAG and the assembly of RA on TAG is largely unknown. In the present study, 11 PLD genes were identified from the Castor Bean Genome Database. Gene expression analysis indicated that RcPLD9 is expressed at relatively high levels in developing seeds compared to other plant tissues. Sequence and phylogenetic analyses revealed that RcPLD9 is a homolog of Arabidopsis PLDζ2. Overexpression of RcPLD9 in the Arabidopsis CL7 line producing C18-HFA resulted in RA content reductions in the polar lipid fraction (mainly PtdCho) and mono-HFA-TAG, but increased RA content in di-HFA-TAG. Since part of RA in di-HFA-TAG is derived from HFA-DAG, the results indicated that RcPLD9 facilitates the channeling of RA from PtdCho to DAG for its assembly on TAG in developing seeds.


Asunto(s)
Proteínas de Arabidopsis/genética , Fosfolipasa D/genética , Ácidos Ricinoleicos/metabolismo , Ricinus communis/genética , Triglicéridos/metabolismo , Arabidopsis/genética , Ricinus communis/metabolismo , Aceite de Ricino/química , Aceite de Ricino/genética , Aceite de Ricino/metabolismo , Endospermo/genética , Endospermo/metabolismo , Ácidos Grasos/genética , Ácidos Grasos/metabolismo , Plantas Modificadas Genéticamente/genética , Plantas Modificadas Genéticamente/metabolismo , Ácidos Ricinoleicos/química , Semillas/genética , Semillas/metabolismo , Triglicéridos/genética
10.
Food Chem ; 314: 126174, 2020 Jun 01.
Artículo en Inglés | MEDLINE | ID: mdl-31981885

RESUMEN

The aim of this work is to develop a W1/O/W2 multiple emulsion with gallic acid in the internal aqueous phase (W1). A quantification method for gallic acid using HPLC-UV was developed and validated. In the first step, a simple W1/O emulsion was prepared with distilled water, polyglycerol polyricinoleate, sodium chloride, gallic acid and pH 5.0 sodium acetate buffer system. The second step consisted of adding the simple emulsion to the external aqueous phase (W2) composed of distilled water, polysorbate 80 and xanthan gum. The multiple emulsion showed pseudoplastic behavior. After 28 days of analysis the multiple emulsion presented a stability index of 75% without pH variation, 89.61% of gallic acid concentration, 59.62% of antioxidant activity in the phosphomolybdenum complex assay and 80.58% of DPPH scavenging activity. It is concluded that the W1/O/W2 emulsion developed was stable for 28 days and maintained more than 50% of gallic acid antioxidant capacity.


Asunto(s)
Ácido Gálico/química , Emulsiones , Glicerol/análogos & derivados , Glicerol/química , Aceite de Brassica napus/química , Ácidos Ricinoleicos/química , Cloruro de Sodio/química , Viscosidad , Agua/química
11.
Prep Biochem Biotechnol ; 50(4): 401-407, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-31829798

RESUMEN

In the present study, we report a reverse-phase high-performance liquid chromatography (RP-HPLC) method for separation of the regio-isomers of Glyceryl MonoRicinoleate (GMR) identified using position specificity of lipases. The approaches explored to identify these regio-isomers include LC-mass spectrometry, UV spectroscopy, and selective hydrolysis with lipases. A distinct UV absorption spectrum and λmax values for each isomer were noted, and mass spectral analysis further revealed their molecular weight. Lastly, the purified regio-isomers were subjected to hydrolysis with two distinctive regio-specific lipases to identified as sn-2 and sn-1(3) GMR. The current methodology of using analytic tool and enzyme specificity provides a useful platform for identifying regio-isomers for structured lipid synthesis.


Asunto(s)
Glicéridos/análisis , Lipasa/química , Ácidos Ricinoleicos/análisis , Aceite de Ricino/química , Cromatografía Líquida de Alta Presión , Cromatografía de Fase Inversa , Glicéridos/química , Hidrólisis , Isomerismo , Ácidos Ricinoleicos/química , Ricinus/química
12.
Enzyme Microb Technol ; 133: 109454, 2020 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-31874691

RESUMEN

Castor oil extracted from castor bean has antibacterial property, and has been used in various folk remedies. The major structural component of castor oil, ricinoleic acid, has actual antibacterial activity. Some phenolic compounds derived from plants have antioxidant property. Among them, vanillyl alcohol from vanilla bean has strong antioxidant activity. As vanillyl alcohol has low solubility in hydrophobic solvents and castor oil has low solubility in hydrophilic solvents, there is practical difficulty in using them. We performed lipase-mediated transesterification using vanillyl alcohol and castor oil, and synthesized ricinoleic acid vanillyl ester (RAVE). 2,2-Diphenyl-1-picrylhydrazyl assay and 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) assay revealed that RAVE had a strong antioxidant activity in various organic solvents. RAVE also had antibacterial activity against some food spoilage bacteria. It showed more powerful antibacterial activity for gram positive bacteria than for gram negative bacteria. The critical micelle concentration of RAVE was measured at 7.36 µM and it partitioned exclusively into emulsion phase in water-emulsion system. Zeta potential measurement, membrane release test, and fluorescent microscopy showed that RAVE inserted itself into the bacterial cell membrane, destroyed membrane permeability, and induced cell death. As such, RAVE is a novel multi-functional compound with antioxidant and antibacterial activity, so it can be used as a functional material in the food and cosmetic industries.


Asunto(s)
Antibacterianos/farmacología , Antioxidantes/farmacología , Bacterias/efectos de los fármacos , Alcoholes Bencílicos/metabolismo , Aceite de Ricino/metabolismo , Lipasa/metabolismo , Antibacterianos/aislamiento & purificación , Esterificación , Ácidos Ricinoleicos , Solventes
13.
Lipids ; 55(2): 89-99, 2020 03.
Artículo en Inglés | MEDLINE | ID: mdl-31867745

RESUMEN

Ricinoleic acid (RA) is the main fatty acid component of castor oil and was found to inhibit Ca2+ -signal transduction pathway-mediated cell cycle regulation in a yeast-based drug screening assay. RA is expected to have antidiabetic, antiallergy, and/or anticancer properties but its target molecule is unknown. To identify a novel pharmacological effect of RA, we investigated its target molecule in the Ca2+ -signal transduction pathway. RA inhibition of calcineurin (CN) was examined in a yeast-based CN inhibitor screening assay using the rsp5A401E mutant and in a phosphatase assay using recombinant human CN. RA showed growth-restoration activity at 5 µg/spot in the CN inhibitor screening assay with the rsp5A401E yeast strain. Furthermore, it directly inhibited CN without immunophilins at Ki = 33.7 µM in a substrate-competitive manner. The effects of RA on CN in mammalian cells were further evaluated by measuring ß-hexosaminidase (ß-HEX) release in RBL-2H3 cells. RA at 50 µM suppressed the release of ß-HEX from RBL-2H3 cells. Moreover, this compound was found to inhibit glycogen synthase kinase-3ß (GSK-3ß), as determined by a kinase assay using recombinant human GSK-3ß. RA inhibited GSK-3ß at Ki = 1.43 µM in a peptide substrate-competitive manner. The inhibition of GSK-3ß by this molecule was further assessed in mammalian cells by measuring the inhibition of glucose production in H4IIE rat hepatoma cells. RA at 25 µM suppressed glucose production in these cells. These findings indicate that RA and/or castor oil could be a useful functional fatty acid to treat allergy or type 2 diabetes.


Asunto(s)
Inhibidores de la Calcineurina/farmacología , Señalización del Calcio/efectos de los fármacos , Aceite de Ricino/química , Ácidos Ricinoleicos/farmacología , Animales , Calcineurina/metabolismo , Evaluación Preclínica de Medicamentos , Regulación de la Expresión Génica/efectos de los fármacos , Glucosa/metabolismo , Glucógeno Sintasa Quinasa 3 beta/metabolismo , Humanos , Fosforilación , Ratas , Saccharomyces cerevisiae/genética , Saccharomyces cerevisiae/crecimiento & desarrollo , Saccharomyces cerevisiae/metabolismo , beta-N-Acetilhexosaminidasas/metabolismo
14.
Food Res Int ; 122: 252-262, 2019 08.
Artículo en Inglés | MEDLINE | ID: mdl-31229079

RESUMEN

Water-in-oil high internal phase emulsions (HIPEs) can provide interesting textures that could be used to reduce trans- and/or saturated fat content in food products. On the other hand oil-in-water emulsions can be found in a variety of food and beverages. Moreover, strategies aiming synthetic or semi-synthetic ingredients replacement by natural alternatives for food applications has been pursuit. For these purposes, the effect of partial replacement of PGPR by lecithin on properties of either W/O-HIPEs or O/W emulsions manufactured from the same initial composition but showing different volume fraction of dispersed phase were investigated aiming to understand the behaviour of emulsifiers' mixture in water-oil or oil-water interfaces. Firstly, water-in-oil HIPEs were produced using a rotor-stator device. At fixed total amount of emulsifier (2% w/w), W/O emulsions stabilized with LEC:PGPR ratios of 0.5:1.5 and 1.0:1.0 showed similar droplet size with a better kinetic stability compared to emulsions containing only PGPR. These results indicated good interaction between LEC and PGPR, which was also confirmed by dynamic interfacial tension profile and interfacial dilational rheology. In order to reduce the droplet size of W/O-HIPEs, these emulsions were subsequently subjected to high-pressure homogenization and interestingly phases inversion was observed. Confocal microscopy confirmed the phases inversion attributed to high input of energy leading to the formation of O/W emulsions. Then both W/O-HIPEs and O/W emulsions were investigated regarding LEC:PGPR mixtures as emulsifiers. All W/O-HIPEs showed shear thinning behavior and high viscosity at low shear rate whereas O/W emulsions showed low viscosity and Newtonian behavior. The increase of lecithin content in emulsifier mixture led to more stable O/W emulsions, whereas more stable W/O-HIPEs were produced by lecithin and PGPR mixtures ratio of 0.5:1.5 and 1.0:1.0.


Asunto(s)
Emulsionantes/química , Emulsiones/química , Glicerol/análogos & derivados , Lecitinas/química , Ácidos Ricinoleicos/química , Manipulación de Alimentos , Glicerol/química , Tamaño de la Partícula , Viscosidad , Agua/química
15.
Food Res Int ; 122: 471-478, 2019 08.
Artículo en Inglés | MEDLINE | ID: mdl-31229102

RESUMEN

The crystal network development, elastic properties scaling behavior, and mechanical reversibility of candelilla wax (CW) oleogels with and without emulsifiers were studied. Saturated monoglycerides (MG) and polyglycerol polyricinoleate (PGPR) were added at 1 or 2 times the critical micelle concentration. Although the micelles of both emulsifiers act as nucleation sites for the mixture of aliphatic acids and alcohols of CW, they did not affect the oleogel's thermodynamic stability. It was established that the crystal network of CW consists of at least two types of crystals, one rich in n-hentriacontane and other rich in aliphatic acids. Both crystals species contributed significantly to the oleogel elasticity. The elastic properties scaling behavior of CW oleogels fitted the fractal model within the weak-link regime. The setting temperature and added emulsifier modified the crystal network fractal dimension. During shearing, oleogels had massive breaking of junction zones, causing the loss of fractality in the crystal network, which in turn decreased the system's elasticity.


Asunto(s)
Emulsionantes/química , Rastreo Diferencial de Calorimetría , Elasticidad , Ácidos Grasos/análisis , Glicerol/análogos & derivados , Glicerol/química , Monoglicéridos/química , Ácido Oléico/análisis , Compuestos Orgánicos/química , Reología , Ácidos Ricinoleicos/química , Aceite de Cártamo/química , Ceras/química , Difracción de Rayos X
16.
ACS Synth Biol ; 8(5): 1055-1066, 2019 05 17.
Artículo en Inglés | MEDLINE | ID: mdl-31018087

RESUMEN

Whole cell biocatalysts can be used to convert fatty acids into various value-added products. However, fatty acid transport across cellular membranes into the cytosol of microbial cells limits substrate availability and impairs membrane integrity, which in turn decreases cell viability and bioconversion activity. Because these problems are associated with the mechanism of fatty acid transport through membranes, a whole-cell biocatalyst that can form caveolae-like structures was generated to promote substrate endocytosis. Caveolin-1 ( CAV1) expression in Escherichia coli increased both the fatty acid transport rate and intracellular fatty acid concentrations via endocytosis of the supplemented substrate. Furthermore, fatty-acid endocytosis alleviated substrate cytotoxicity in E. coli. These traits attributed to bacterial endocytosis resulted in dramatically elevated biotransformation efficiencies in fed-batch and cell-recycle reaction systems when caveolae-forming E. coli was used for the bioconversion of ricinoleic acid (12-hydroxyoctadec-9-enoic acid) to ( Z)-11-(heptanoyloxy) undec-9-enoic acid. We propose that CAV1-mediated endocytosing E. coli represents a versatile tool for the biotransformation of hydrophobic substrates.


Asunto(s)
Endocitosis , Escherichia coli/metabolismo , Ácidos Grasos/metabolismo , Biocatálisis , Biotransformación , Caveolas/metabolismo , Caveolina 1/genética , Caveolina 1/metabolismo , Ácidos Grasos/química , Ácidos Ricinoleicos/metabolismo
17.
J Food Sci ; 84(4): 782-791, 2019 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-30875433

RESUMEN

Cholecalciferol, also known as vitamin D3 , is a recognized therapeutic agent for treatment of bone diseases and cancer. However, instability and poor bioavailability have been major challenges for delivering Vitamin D3 . The objective of this study was to formulate improved nanostructured lipid carrier (NLC) vitamin D3 emulsions. We tested the effect of different carrier oils and the use of a solid lipid nanoparticle emulsifier, polyglycerol polyricinoleate (PGPR) on the stability of the vitamin D3 emulsions. In contrast to the control that used glyceryl monostearate (GMS) the PGPR substitution resulted in relatively small particle sizes (0.30 to 0.43 µm), with high absolute value of zeta potentials (39.5 to 67.8 mV) and high encapsulation efficiency (85.2% to 90.4%). The stability of the NLC emulsions against environmental stresses was evaluated under varying conditions of ionic strength, pH, freeze-thaw cycles, and storage at different temperatures. Although NLC emulsions were stable at high ionic strengths, they were found to be unstable at low pH (<3), which led to aggregation and coalescence of emulsion droplets. In case of freeze-thaw stress, although relatively stable compared to control NLC, the PGPR substituted groups exhibited a slight increase in particle size and a decrease in zeta potential when the cycle was repeated five times. Additionally, we found that PGPR-substituted emulsions showed higher liquid dispersion stability than controls at 25 and 65 °C. Thus, we have formulated a modified NLC vitamin D3 emulsion that can be widely used in the food industry. PRACTICAL APPLICATION: Vitamin D3 , an essential micronutrient, is often added as supplements in food products and beverages for added health benefits. However, the stability of vitamin D3 emulsions that are used in the preparation of such products has been a major concern. We have developed a modified emulsion that has improved stability against environmental stresses. We believe, in future, this formulation can be efficiently used in the food industry.


Asunto(s)
Colecalciferol/química , Emulsiones/química , Glicerol/análogos & derivados , Nanoestructuras/química , Ácidos Ricinoleicos/química , Composición de Medicamentos , Emulsionantes , Glicerol/química , Concentración Osmolar , Tamaño de la Partícula
18.
Metabolomics ; 15(1): 6, 2019 01 03.
Artículo en Inglés | MEDLINE | ID: mdl-30830477

RESUMEN

INTRODUCTION: Castor (Ricinus communis L.) seeds are valued for their production of oils which can comprise up to 90% hydroxy-fatty acids (ricinoleic acid). Castor oil contains mono-, di- and tri- ricinoleic acid containing triacylglycerols (TAGs). Although the enzymatic synthesis of ricinoleic acid is well described, the differential compartmentalization of these TAG molecular species has remained undefined. OBJECTIVES: To examine the distribution of hydroxy fatty acid accumulation within the endosperm and embryo tissues of castor seeds. METHODS: Matrix assisted laser desorption/ionization mass spectrometry imaging was used to map the distribution of triacylglycerols in tissue sections of castor seeds. In addition, the endosperm and embryo (cotyledons and embryonic axis) tissues were dissected and extracted for quantitative lipidomics analysis and Illumina-based RNA deep sequencing. RESULTS: This study revealed an unexpected heterogeneous tissue distribution of mono-, di- and tri- hydroxy-triacylglycerols in the embryo and endosperm tissues of castor seeds. Pathway analysis based on transcript abundance suggested that distinct embryo- and endosperm-specific mechanisms may exist for the shuttling of ricinoleic acid away from phosphatidylcholine (PC) and into hydroxy TAG production. The embryo-biased mechanism appears to favor removal of ricinoleic acid from PC through phophatidylcholine: diacylglycerol acyltransferase while the endosperm pathway appears to remove ricinoleic acid from the PC pool by preferences of phospholipase A (PLA2α) and/or phosphatidylcholine: diacylglycerol cholinephosphotransferase. CONCLUSIONS: Collectively, a combination of lipidomics and transcriptomics analyses revealed previously undefined spatial aspects of hydroxy fatty acid metabolism in castor seeds. These studies underscore a need for tissue-specific studies as a means to better understand the regulation of triacylglycerol accumulation in oilseeds.


Asunto(s)
Ácidos Ricinoleicos/metabolismo , Ricinus/metabolismo , Ricinus communis/metabolismo , Aceite de Ricino/metabolismo , Diacilglicerol Colinafosfotransferasa , Ácidos Grasos/metabolismo , Fosfolipasas A2 Grupo IV , Fosfatidilcolinas , Ácidos Ricinoleicos/análisis , Ricinus/química , Ricinus/genética , Semillas/química , Semillas/metabolismo , Análisis de Secuencia de ARN , Espectrometría de Masa por Láser de Matriz Asistida de Ionización Desorción/métodos , Triglicéridos/metabolismo
19.
Planta ; 249(5): 1285-1299, 2019 May.
Artículo en Inglés | MEDLINE | ID: mdl-30610363

RESUMEN

MAIN CONCLUSION: In vivo and in vitro analyses of Euphorbiaceae species' triacylglycerol assembly enzymes substrate selectivity are consistent with the co-evolution of seed-specific unusual fatty acid production and suggest that many of these genes will be useful for biotechnological production of designer oils. Many exotic Euphorbiaceae species, including tung tree (Vernicia fordii), castor bean (Ricinus communis), Bernardia pulchella, and Euphorbia lagascae, accumulate unusual fatty acids in their seed oils, many of which have valuable properties for the chemical industry. However, various adverse plant characteristics including low seed yields, production of toxic compounds, limited growth range, and poor resistance to abiotic stresses have limited full agronomic exploitation of these plants. Biotechnological production of these unusual fatty acids (UFA) in high yielding non-food oil crops would provide new robust sources for these valuable bio-chemicals. Previous research has shown that expression of the primary UFA biosynthetic gene alone is not enough for high-level accumulation in transgenic seed oils; other genes must be included to drive selective UFA incorporation into oils. Here, we use a series of in planta molecular genetic studies and in vitro biochemical measurements to demonstrate that lysophosphatidic acid acyltransferases from two Euphorbiaceae species have high selectivity for incorporation of their respective unusual fatty acids into the phosphatidic acid intermediate of oil biosynthesis. These results are consistent with the hypothesis that unusual fatty acid accumulation arose in part via co-evolution of multiple oil biosynthesis and assembly enzymes that cooperate to enhance selective fatty acid incorporation into seed oils over that of the common fatty acids found in membrane lipids.


Asunto(s)
Aciltransferasas/metabolismo , Euphorbiaceae/enzimología , Euphorbiaceae/metabolismo , Ácidos Grasos/metabolismo , Aceites de Plantas/metabolismo , Semillas/enzimología , Semillas/metabolismo , Regulación de la Expresión Génica de las Plantas , Ácidos Ricinoleicos/metabolismo
20.
Int J Biol Macromol ; 121: 373-380, 2019 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-30287377

RESUMEN

A novel bio-based polyurethane/chitosan foam (PU/chitosan) was synthesized using a polyol derived from castor oil and applied to remove Food Red 17 dye (FR17) from aqueous solutions. PU/chitosan foam presented better characteristics and adsorption potential than polyurethane foam (PU). PU/chitosan foam showed a semi-crystalline structure, with several functional groups, high porosity and good mechanical properties. These characteristics are adequate for adsorptive separations. Using identical adsorption conditions, PU/chitosan was able to remove >98% of FR17 dye from the solution, while, PU removed only 40%. The adsorption of FR17 on PU/chitosan composite foam was favored at pH 2. Pseudo-second order model was the most adequate to represent the kinetic data. The equilibrium data followed the Sips model, with a maximum adsorption capacity of 267.24 mg g-1. The adsorption process was spontaneous, favorable and endothermic. The results showed that polyurethane foams are capable to support chitosan, generating an adsorbent with better mechanical characteristics and high potential to remove anionic dyes from aqueous media.


Asunto(s)
Compuestos Azo/química , Compuestos Azo/aislamiento & purificación , Quitosano/química , Poliuretanos/química , Poliuretanos/síntesis química , Ácidos Ricinoleicos/química , Adsorción , Aceite de Ricino/química , Técnicas de Química Sintética , Concentración de Iones de Hidrógeno , Cinética , Polímeros/química , Termodinámica , Agua/química , Contaminantes Químicos del Agua/química , Contaminantes Químicos del Agua/aislamiento & purificación
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