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Ricinoleic acid (RA) from castor oil was employed in biotransformation of peach-flavoured γ-decalactone (GDL), using a Candida parapsilosis strain (MTCC13027) which was isolated from waste of pineapple crown base. Using four variables-pH, cell density, amount of RA, and temperature-the biotransformation parameters were optimized using RSM and BBD. Under optimized conditions (pH 6, 10 % of microbial cells, 10 g/L RA at 28°C), the conversion was maximum and resulted to 80 % (+)-GDL (4.4 g/L/120 h) yield in shake flask (500 mL). Furthermore, optimization was achieved by adjusting the aeration and agitation parameters in a 3 L bioreactor, which were then replicated in a 10 L bioreactor to accurately determine the amount of (+)-GDL. In bioreactor condition, 4.7 g/L (>85 %) of (+)-GDL is produced with 20 % and 40 % dissolved oxygen (1.0 vvm) at 150 rpm in 72 h and 66 h, respectively. Further, a new Al-Mg-Ca-Si composite column-chromatography method is developed to purify enantiospecific (+)-GDL (99.9 %). This (+)-GDL is 100 % nature-identical as validated through 14 C-radio-carbon dating. Thorough chemical investigation of enantiospecific (+)-GDL is authenticated for its use as flavour. This bioflavour has been developed through a cost-effective biotechnological process in response to the demand from the food industry on commercial scale., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. Competing interests The authors declare no competing interest., (Copyright © 2024 Elsevier B.V. All rights reserved.)

PGPR is an emulsifier (E476) widely used in the food industry. In this study, a gas chromatography-flame ionisation detection (GC-FID) method was developed for the quantitative characterisation of the polyglycerol composition of PGPR. The method was validated to analyse quantitatively the polyglycerol species in neat PGPR products and in PGPR samples present in a lipid matrix. This method consists of saponification, acidification and petroleum ether extraction to remove interfering fatty acids, neutralisation, silylation and finally GC-FID analysis. Phenyl β-D-glucopyranoside was used as internal standard as sorbitol proved unsuitable due to its susceptibility to interference from Na/K chloride during silylation. The response factors of glycerol and diglycerol towards phenyl β-D-glucopyranoside were determined using pure standards, while response factors of polyglycerols with a degree of polymerisation of at least 3 could be reliably estimated according to an effective carbon number (ECN) approach. The validity of the method applied to PGPR samples was further supported on the basis of a mass balance considering the experimentally determined polyglycerol and fatty acid content. Moreover, recoveries of di-, tri-, tetra- and pentaglycerol were more than 95% for various PGPR samples added to two different lipid matrices at 2 wt% and 5 wt% concentrations. Furthermore, the method proved to be very repeatable (with relative standard deviation values below 2.2%). On the other hand, the inevitable presence of glycerol in the lipid samples caused fouling of the detector and column overloading, requiring frequent cleaning of the detector and trimming off part of the column.

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., (© 2023 Institute of Food Technologists®.)

The alternating architecture and hydrophobic side chains hinder hydrolytic cleavage and anhydride interchange in poly(sebacic acid-ricinoleic acid) (P(SA-RA)), which provides stable polyanhydrides at room temperature. In this report, a series of polyanhydrides were designed to investigate the effect of ester bonds, hydrophobic side chains, phenyl moieties, and their distance from anhydride bonds on their stability and properties. Polyanhydrides with alternating architecture are constructed by the polymerization of ester-diacids prepared from ricinoleic or other hydroxy acids with anhydrides such as succinic, maleic, and phthalic anhydrides. The hydrophobic side chains are designed closer to anhydride bonds to investigate hindrance to hydrolytic cleavage and anhydride interchange. Polyanhydrides were obtained by the activation of ester-diacid using acetic anhydride followed by melt condensation. The reactions were monitored by NMR, Fourier transform infrared (FTIR), and gel permeation chromatography (GPC). The synthesized poly(ester-anhydride)s with a shorter chain length compared to P(SA-RA) were stable at room temperature. The hydrolytic degradation studies reveal that the phenyl moiety present in poly(ricinoleic acid phthalate) (PRAP) and poly(hydroxystearic acid phthalate) (PHSAP) reduces the hydrolysis of anhydride bonds. Poly(hydroxyoctanoic acid succinate) (PHOAS) demonstrates the highest molecular weight of all tested polymers. The results reveal that the presence of hydrophobic side chains, phenyl moieties, and their distance from anhydride bonds significantly improves the stability. These stable polyanhydrides can provide convenience to use in control drug-delivery applications. The in vitro drug release study using ibuprofen shows that polymers with aromatic units such as PRAP and PHSAP establish sustained release, which presents more than 50 and 40% of ibuprofen over a period of 28 days.

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., (© 2022. The Author(s).)

Polyglycerol polyricinoleate (PGPR) is a powerful lipophilic emulsifier used in low-fat spreads and chocolate. It should be used at the lowest level at which the desired technological effect is achieved, not exceeding the specified maxima according to Annexe II to Regulation (EC) No 1333/2008. A gas chromatography-flame ionisation detection (GC-FID) method was developed for quantification of PGPR. This method is based on estimating the content of ricinoleic acid using 12-hydroxyoctadecanoic acid as an internal standard, from which the PGPR concentration was deduced. The method involved saponification, methylation, a two-step solid phase extraction (SPE) separation of the fatty acid methyl esters (FAMEs), silylation, and GC-FID analysis. The limits of detection and quantification of ricinoleic acid were 2.2 and 6.7 μg/mL, respectively, at 0.1 µL injection volume. Considering the average content of ricinoleic acid in PGPR (i.e. 86.63 ± 2.0 wt%) and the amount of food product that is used in the proposed protocol (i.e. 20 mg), this resulted in a LOD and LOQ of 0.76 and 2.32 μg PGPR per mg of food product, respectively. The developed method was validated by determining PGPR recovery from a high oleic sunflower oil (HOSO) solution, from chocolate spiked with a commercially available PGPR, and from commercially available low fat spreads with a known PGPR content. The actual recovery was more than 95% for all matrices, indicating the accuracy of the developed analytical technique. Moreover, the method proved to be very reproducible, with RSD < 4% for concentrations ranging from 0.2 to 5 wt%. The results showed that our proposed GC-FID method enables the reliable and quantitative determination of the PGPR concentration in commercial food products with various fat contents.

Nosocominal infections associated with biofilm formation on urinary catheters cause serious complications. The aim of this study was to investigate the feasibility of the polyurethane (PU) catheter modified with tetracycline hydrochloride (TCH) attached Ag nanoparticles embedded PolyRicinoleic acid-Polystyrene Nanoparticles (PU-TCH-AgNPs-PRici-PS NPs) and the influence on antimicrobial and antibiofilm activity of urinary catheters infected by Escherichia coli and Staphylococcus aureus . For this purpose, AgNPs embedded PRici graft PS graft copolymers (AgNPs-PRici-g-PS) were synthesized via free radical polymerization and characterized by FTIR, HNMR and DSC. AgNPs-PRici-PS NPs were prepared and optimized by the different parameters and the optimized size of nanoparticle was found as about 150 ± 1 nm. The characterization of the nanoparticles and the morphological evaluation were carried out by FTIR and SEM. Short term stability of nanoparticles was realised at 4°C for 30 days. In vitro release profiles of TCH and Ag NPs were also investigated. The formation of biofilm on PU modified TCH-Ag NPs-PRici-PS NPs, was evaluated and the biocompatibility test of the nanoparticles was realized via the mouse fibroblast (L929) and mouse urinary bladder cells (G/G An1). This is the first time that TCH-AgNPs-PRici-PS NPs used in the modification of PU catheter demonstrated high antimicrobial and antibiofilm activities against the urinary tract infection.

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 W 1 phase via a two-step procedure. Creamed emulsion could be fabricated at W 1 /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 W 1 /O/W 2 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., (Copyright © 2021 Elsevier B.V. All rights reserved.)

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., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier Ltd. All rights reserved.)

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., (© 2020 AOCS.)

Microbial production of hydroxy fatty acids (HFAs) was widely studied because of important biological properties of HFAs. Among microorganisms producing HFAs, Pseudomonas aeruginosa PR3 was well known to produce various HFAs from different unsaturated fatty acids. Recently, a new variant species of P. aeruginosa PR3 was isolated and characterized, showing improved efficiency for producing 7,10-dihydroxy-8(E)-octadecenoic acid from oleic acid. In this study, we report the production of 7,10,12-trihydroxy-8(E)-octadecenoic acid (TOD) from ricinoleic acid by the newly isolated P. aeruginosa KNU-2B. TOD was efficiently produced from ricinoleic acid by KNU-2B with the maximum conversion yield of 56.7% under the optimum reaction conditions of pH 8.0 and 48-h incubation at 27 °C, 150 rpm. Under optimized reaction conditions, maximum TOD production reached 340.3 mg/100 mL of the culture. However, requirement of nutritional factors by KNU-2B for production of TOD were considerably different from those by PR3 strain.

(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., (© 2020 Wiley Periodicals, Inc.)

The aim of this work is to develop a W 1 /O/W 2 multiple emulsion with gallic acid in the internal aqueous phase (W 1 ). A quantification method for gallic acid using HPLC-UV was developed and validated. In the first step, a simple W 1 /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 (W 2 ) 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 W 1 /O/W 2 emulsion developed was stable for 28 days and maintained more than 50% of gallic acid antioxidant capacity., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier Ltd. All rights reserved.)

In this study, anthocyanin-loaded water 1 -in-oil-in-water 2 (W 1 /O/W 2 ) double Pickering emulsions stabilized by octenylsuccinate quinoa starch (OSQS) were optimized, and their storage stability and in vitro gastrointestinal digestion were evaluated. Novel starch-based double emulsions as anthocyanin cargos were achieved at 2% (w/v of oil) of polyglycerol polyricinoleate concentration, the W 1 /O volume proportion of 3:7, 6% (w/v of total volume) of OSQS concentration, and the volume proportion of (W 1 /O): W 2  = 6:4 and 5:5. CLSM results evidenced the formation of double Pickering emulsions, and the significant decreases in the encapsulation stability of anthocyanins were closely related to the increases in the droplet size induced by osmotic pressure. Less than 15% of anthocyanins in the double Pickering emulsions was released after incubated for 60 min under simulated stomach conditions; controlled-release of anthocyanins was observed during the 120 min of simulated intestinal digestion, consistent with starch hydrolysis data. These findings will be useful for designing starch-based double Pickering emulsion with intestinal-targeted delivery as a novel carrier of sensitive hydrophilic bioactive compounds., (Copyright © 2019 Elsevier B.V. All rights reserved.)

Long-chain aliphatic amines such as (S,Z)-heptadec-9-en-7-amine and 9-aminoheptadecane were synthesized from ricinoleic acid and oleic acid, respectively, by whole-cell cascade reactions using the combination of an alcohol dehydrogenase (ADH) from Micrococcus luteus, an engineered amine transaminase from Vibrio fluvialis (Vf-ATA), and a photoactivated decarboxylase from Chlorella variabilis NC64A (Cv-FAP) in a one-pot process. In addition, long chain aliphatic esters such as 10-(heptanoyloxy)dec-8-ene and octylnonanoate were prepared from ricinoleic acid and oleic acid, respectively, by using the combination of the ADH, a Baeyer-Villiger monooxygenase variant from Pseudomonas putida KT2440, and the Cv-FAP. The target compounds were produced at rates of up to 37 U g -1 dry cells with conversions up to 90 %. Therefore, this study contributes to the preparation of industrially relevant long-chain aliphatic chiral amines and esters from renewable fatty acid resources., (© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

A series of novel substituted 1- O -alkylglycerols (AKGs) containing methoxy ( 8 ), gem -difluoro ( 9 ), azide ( 10 ) and hydroxy ( 11 ) group at 12 position in the alkyl chain were synthesized from commercially available ricinoleic acid ( 12 ). The structures of these new synthesized AKGs were established by NMR experiments as well as from the HRMS and elementary analysis data. The antimicrobial activities of the studied AKGs 8 - 11 were evaluated, respectively, and all compounds exhibited antimicrobial activity to different extents alone and also when combined with some commonly used antibiotics (gentamicin, tetracycline, ciprofloxacin and ampicillin). AKG 11 was viewed as a lead compound for this series as it exhibited significantly higher antimicrobial activity than compounds 8 - 10 .

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 λ max 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.

In addition to our previous efforts toward bioenzymatic and chemical transformations of ricinoleic acid and oleic acid to their corresponding ,-dicarboxylic acids via their ester intermediates driven in Escherichia coli cells, several efficient oxidation conditions were investigated and optimized for the conversion of -hydroxycarboxylic acids to ,-dicarboxylic acids. Pd/C-catalyzed oxidation using NaBH 4 in a basic aqueous alcohol and Ni(II) salt-catalyzed oxidation using aqueous sodium hypochlorite were considered to be excellent as a hybrid reaction for three successive chemical reactions (hydrogenation, hydrolysis, and oxidation) and an eco-friendly, cost-effective, and practical approach, respectively. Omega-hydroxycarboxylic acids and -aminocarboxylic acid were also easily prepared as useful building blocks for plastics or bioactive compounds from the bioenzymatically driven ester intermediate. The scope of the developed synthetic methods can be utilized for large-scale synthesis and various derivatizations., Competing Interests: The authors declare no conflicts of interest.

In vitro dynamic aroma release over oil-in-water (o/w) and water-in-oil-in-water (w/o/w) emulsions stabilized with Tween 20 or octenyl succinic anhydride (OSA) starch as a hydrophilic emulsifier and polyglycerol polyricinoleate (PGPR) as a hydrophobic emulsifier was investigated. The equal-molecular-weight hydrophilic aroma diacetyl (2,3-butanedione) or relatively more-hydrophobic 3-pentanone was added to the emulsions prepared by high speed mixing, or membrane emulsification followed by thickened with xanthan gum removing droplet size distribution and creaming as variables affecting dynamic release. Results showed the differences of w/o/w emulsions in the dynamic release compared to o/w emulsions mainly depended on aroma hydrophobicity, emulsion type, emulsifier-aroma interactions, and creaming. Xanthan led to a reduced headspace replenishment. Interfacially adsorbed OSA starch and xanthan-OSA starch interaction influenced on diacetyl release over emulsions. OSA starch alone interacted with 3-pentanone. This study demonstrates the potential impact of emulsifying and thickening systems on aroma release systems and highlights that specific interactions may compromise product quality.

Background: Worldwide iron deficiency in diets has led to a growing interest in the development of food-compatible encapsulation systems for soluble iron, which are able to prevent iron's undesirable off-taste and pro-oxidant activity. Here, we explore the use of double emulsions for this purpose, and in particular, how the lipophilic emulsifier (polyglycerol polyricinoleate, PGPR) concentration influences the physicochemical stability of water-in-oil-in-water (W 1 /O/W 2 ) double emulsions containing ferrous sulphate in the inner water droplets. Double emulsions were prepared with sunflower oil containing 10 to 70 g kg -1 PGPR in the oil phase, and were monitored for droplet size distribution, morphology, encapsulation efficiency (EE) and oxidative stability over time., Results: Fresh double emulsions showed an initial EE higher than 88%, but EE decreased upon storage, which occurred particularly fast and to a high extent in the emulsions prepared with low PGPR concentrations. All double emulsions underwent lipid oxidation, in particular those with the highest PGPR concentration, which could be due to the small inner droplet size and thus promoted contact between oil and the internal water phase., Conclusion: These results show that a too high PGPR concentration is not needed, and sometimes even adverse, when developing double emulsions as iron encapsulation systems. © 2019 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry., (© 2019 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.)

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., (Copyright © 2019 Elsevier Ltd. All rights reserved.)

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., (Copyright © 2019. Published by Elsevier Ltd.)

Natural gamma-decalactone (GDL) produced by biotransformation is an essential food additive with a peach-like aroma. However, the difficulty of effectively controlling the concentration of the substrate ricinoleic acid (RA) in water limits the biotransformation productivity, which is a bottleneck for industrialization. In this study, expanded vermiculite (E-V) was utilized as a carrier of RA to increase its distribution in the medium. E-V and three commonly used organic compounds were compared with respect to their effects on the biotransformation process, and the mechanism was revealed. Scanning electron microscopy, Fourier transform infrared spectroscopy and thermogravimetric analysis indicated that RA was physically adsorbed onto the surface of and inside E-V instead of undergoing a chemical reaction, which increased the opportunity for interactions between microorganisms and the substrate. The highest concentration of GDL obtained in the medium with E-V was 6.2 g/l, which was 50% higher than that in the reference sample. In addition, the presence of E-V had no negative effect on the viability of the microorganisms. This study provides a new method for producing natural GDL through biotransformation on an industrial scale.

Water-in-oil-in-water emulsions containing an internalised salt solution were stabilised with non-chemically modified waxy rice starch (WRS), and octinyl succinic anhydride (OSA) as reference, to release salt during oral processing due to amylase-induced destabilisation. Salt levels were 1.5 g salt and 0.47 g salt per 100 g external and internal aqueous phases, respectively. Variables were the starch content (2, 3, 4 g per 100 g emulsion; 20 g oil per 100 g emulsion), level of polyglycerol polyricinoleate (PGPR) as a lipophilic emulsifier (0.29, 0.57 g per 100 g emulsion) and ambient-pressure processing temperature for WRS gelatinisation, the non-chemical modification process, (75 ± 3, 88 ± 5 °C). OSA starch was used under previously applied conditions (2, 3, 4 g starch, 0.57 g PGPR per 100 g emulsion, 25 ± 5 °C). Emulsions were stable for three months, except OSA and lower level PGPR low temperature processed WRS emulsions lost salt into the external emulsion phase. One day after processing, encapsulation efficiency (EE) was as predicted from the composition for OSA emulsions, while at the same PGPR content an external aqueous phase was incorporated into the oil droplets of the WRS emulsion increasing EE. Salt release was assessed in vitro and through sensory evaluation using paired comparison testing. The results revealed that the efficacy of this salt reduction approach was enhanced for gelatinised WRS compared to OSA starch stabilised emulsions. Consumer tests on a tomato soup, to validate this salt reduction approach for a real food, revealed a possible 25% salt reduction, compared to current UK products.

We use coarse-grained molecular dynamics simulations to study the effect of surfactant structure on the ordering of bulk tristearin at an oil-water interface. In the absence of surfactant, tristearin acyl chains are marginally aligned normal to the interface. The surfactant glycerol monooleate (GMO), a common small-molecule monoacylglycerol (MW: 357 g/mol), preferentially adsorbs to the oil-water interface, displacing more of the tristearin as its concentration increases. The tristearin that remains at the interface is closely aligned normal to the interface. Adjacent to the interface, bulk tristearin increasingly aligns with its acyl chains entwined with the GMO acyl chain, which also preferentially aligns normal to the interface. In contrast, polyglycerol polyricinoleate (PGPR), a bulkier, polymeric surfactant (MW: 1398 g/mol for a molecule with five monomers), both displaces tristearin from the interface and reduces the alignment of the molecules that remain. We suggest that the similar fatty acid moieties of GMO (oleic acid) and tristearin (stearic acid) lead to liquid-state association and alignment, the latter of which can then serve as a template onto which tristearin crystals can nucleate. Conversely, by both displacing tristearin from the interface and reducing alignment below that of the surfactant-free system, PGPR eliminates the possibility of tristearin interfacial crystallisation., (Copyright © 2019 Elsevier B.V. All rights reserved.)

Cholecalciferol, also known as vitamin D 3 , is a recognized therapeutic agent for treatment of bone diseases and cancer. However, instability and poor bioavailability have been major challenges for delivering Vitamin D 3 . The objective of this study was to formulate improved nanostructured lipid carrier (NLC) vitamin D 3 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 D 3 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 D 3 emulsion that can be widely used in the food industry. PRACTICAL APPLICATION: Vitamin D 3 , an essential micronutrient, is often added as supplements in food products and beverages for added health benefits. However, the stability of vitamin D 3 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., (© 2019 Institute of Food Technologists®.)

Although many investigations on phytochemicals in rice plant parts and root exudates have been conducted, information on the chemical profile of essential oil (EO) and potent biological activities has been limited. In this study, chemical compositions of rice leaf EO and in vitro biological activities were investigated. From 1.5 kg of fresh rice leaves, an amount of 20 mg EO was obtained by distillation and analyzed by gas chromatography-mass spectrometry (GC-MS), electrospray ionization (ESI), and atmospheric pressure chemical ionization (APCI) to reveal the presence of twelve volatile constituents, of which methyl ricinoleate (27.86%) was the principal compound, followed by palmitic acid (17.34%), and linolenic acid (11.16%), while 2-pentadecanone was the least (2.13%). Two phytoalexin momilactones A and B were first time identified in EO using ultra-performance liquid chromatography coupled with electrospray mass spectrometry (UPLC/ESI-MS) (9.80 and 4.93 ng/g fresh weight, respectively), which accounted for 7.35% and 3.70% of the EO, respectively. The assays of DPPH (IC 50 = 73.1 µg/mL), ABTS (IC 50 = 198.3 µg/mL), FRAP (IC 50 = 700.8 µg/mL) and β-carotene oxidation (LPI = 79%) revealed that EO possessed an excellent antioxidant activity. The xanthine oxidase assay indicated that the anti-hyperuricemia potential was in a moderate level (IC 50 = 526 µg/mL) as compared with the standard allopurinol. The EO exerted potent inhibition on growth of Raphanus sativus, Lactuca sativa , and two noxious weeds Echinochloa crus-galli , and Bidens pilosa , but in contrast, the growth of rice seedlings was promoted. Among the examined plants, the growth of the E. crus-galli root was the most inhibited, proposing that constituents found in EO may have potential for the control of the problematic paddy weed E. crus-galli . It was found that the EO of rice leaves contained rich phytochemicals, which were potent in antioxidants and gout treatment, as well as weed management. Findings of this study highlighted the potential value of rice leaves, which may provide extra benefits for rice farmers.

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., (Copyright © 2018 Elsevier B.V. All rights reserved.)

Currently, nanoparticles (NPs) made of amphiphilic block copolymer are still an essential part of drug delivery system. Here, we report a novel amphiphilic block copolymer and paclitaxel (PTX)-loaded copolymer NPs for the controlled delivery of PTX. The block copolymer was synthesized via melt polycondensation method of methoxy poly(ethylene glycol) (mPEG), sebacic acid (SA) and ricinoleic acid (RA). A series of characterization approaches such as Fourier Transform Infrared Spectroscopy (FTIR), 1 Hydrogen-Nuclear Magnetic Resonance ( 1 H-NMR), Differential Scanning Calorimetry (DSC), X-Ray Diffraction (XRD) and Gel Permeation Chromatography (GPC) applied have shown that the amphiphilic block copolymer was prepared as designed. NPs prepared by nanoprecipitation method consist of mPEG segments as the hydrophilic shell and RA-SA segments as the hydrophobic core, hydrophobic PTX was encapsulated as model drug. Subsequently, Transmission Electron Microscopy (TEM) analysis indicated that the spherical NPs have effective mean diameters ranging from 100 to 400 nm. Dynamic Light Scattering (DLS) analysis also revealed the controllable NPs diameter by modulating the mass ratio of RA to SA and drug loading amount (DLA). Besides, biphasic profile with zero order drug release was observed in general in vitro release behaviors of PTX from NPs. Further investigation confirmed that the release behaviors depend on the crystallinity of hydrophobic RA-SA segments. Results above suggest that NPs with amphiphlic block copolymer mPEG-b-P(RA-SA)-b-mPEG have a remarkable potential as a carrier for hydrophobic drug delivery in cancer therapy.

Based on ricinoleic acid, two asymmetric bolaamphiphiles with unsymmetrical hydrophobic skeletons and two different hydrophilic head groups were designed and synthesized. The first bola compound had acetylcholine (ACh) and maleimide (MAL) head groups while the second was derived from the first bolaamphiphile by thiol-ene conjugation of its maleimide moiety with l-glutathione and possessed ACh and l-glutathione-MAL head groups. Both synthetic bolaamphiphiles were characterized by common spectroscopic methods. The asymmetric bola compound with ACh and MAL head groups was investigated for its ability to self-aggregate into nanoparticles and showed to form in aqueous media nano-sized vesicles that were stable, positively charged and had symmetrical monolayer membrane with antiparallel packing. These vesicles prepared with or without membrane stabilizers such as cholesterol (CHOL) and cholesteryl hemisuccinate (CHEMS) were able to encapsulate carboxyfluorescein (CF), a water soluble and self-quenching marker and particularly those without additives were more CF encapsulating. The synthesis of bolaamphiphile with ACh-l-glutathione-MAL head groups gives evidence that the bola with ACh and MAL head groups can be utilized as a precursor of a plethora of asymmetric bolas., (Copyright © 2018 Elsevier B.V. All rights reserved.)

The dynamic collision of emulsified water drops in the presence of non-ionic surfactants plays a crucial role in many practical applications. Interaction force between water drops coated with non-ionic food grade surfactants is expected to exhibit rich dynamic behavior that is not yet explored. The collision forces between immobilized water drops in canola oil in the presence of a well-known food grade surfactant polyglycerol polyricinoleate (PGPR) are measured at concentrations well below typically used to form stable emulsions. An extension or kink, attributed to a short-range attractive interaction due to PGPR bridging between the drops, was observed in the retract portion of the force curves at higher applied forces or slower collision velocities. The Stokes-Reynolds-Young-Laplace (SRYL) model was used to calculate theoretical force curves. For higher collisions velocities, the agreement between the calculated and experiment data was acceptable, but the SRYL model failed to describe the extension or kink feature observed at slower velocities below. Both the AFM data and the comparison to the model calculation indicated the presence of a short-range attractive force, not of a hydrodynamic origin, attributed to the bridging and extension of PGPR molecules on the surface of water drops below saturation of the interface., (Copyright © 2018 Elsevier Inc. All rights reserved.)

Firstly, we report the localization analysis of the lipid components of a water-in-oil (W/O) semi-solid emulsion by mass spectrometry imaging (MSI). Uniform emulsion droplets were prepared using microchannel emulsification devices with lecithin, stearic acid-binding monoglyceride (St-MAG), and polyglycerol polyricinoleate (PGPR) as emulsifiers. The mass image gives us the localization of phosphatidylcholine (PC) in lecithin, St-MAG, tripalmitin (PPP), medium-chain triglyceride (MCT), and high-melting-point triglyceride tristearin (C18-TAG). PC, St-MAG, and PPP were localized at the interface with the dispersed water droplets. PC and PPP took the same localized position, suggesting an interaction between PC and PPP at the interface. Conversely, PC existed in other regions with St-MAG. MSI revealed multiple target molecules in fat products in a single measurement, and it is expected to reveal fat crystallization at the emulsion interfaces, which will clarify the mechanisms related to the physical properties of high-fat products such as fat spread and butter., (Copyright © 2017 Elsevier Ltd. All rights reserved.)

Particle-stabilized W 1 /O/W 2 emulsion gels were fabricated using a two-step procedure: ( i) a W 1 /O emulsion was formed containing saccharose (for osmotic stress balance) and gelatin (as a gelling agent) in the aqueous phase and polyglycerol polyricinoleate (a lipophilic surfactant) in the oil phase; ( ii) this W 1 /O emulsion was then homogenized with another water phase (W 2 ) containing wheat gliadin nanoparticles (hydrophilic emulsifier). The gliadin nanoparticles in the external aqueous phase aggregated at pH 5.5, which led to the formation of particle-stabilized W 1 /O/W 2 emulsion gels with good stability to phase separation. These emulsion gels were then used to coencapsulate a hydrophilic bioactive (epigallocatechin-3-gallate, EGCG) in the internal aqueous phase (encapsulation efficiency = 65.5%) and a hydrophobic bioactive (quercetin) in the oil phase (encapsulation efficiency = 97.2%). The emulsion gels improved EGCG chemical stability and quercetin solubility under simulated gastrointestinal conditions, which led to a 2- and 4-fold increase in their effective bioaccessibility, respectively.

The role of the lipophilic surfactant, polyglycerol polyricinoleate (PGPR) in water transfer in food-grade double emulsions was investigated, and related to physical emulsion stability. Double (W/O/W) emulsions were prepared with various PGPR concentrations (0.5-5.0 wt%) in the oil phase, at initial osmotic pressure differences of up to 1.1 MPa between the water phases. At high PGPR concentrations (>2 wt%), emulsions showed good physical stability, with encapsulation efficiency close to 100%. It was found that PGPR is involved in water transfer between the water phases through reverse micelle formation by PGPR molecules or hydrated monomers of PGPR, and this allows for controlled swelling. Emulsions that are initially of low viscosity (milk-like emulsions), obtain an apparent viscosity of up to 3 Pa·s, and this effect can be used to tune the emulsion properties to the targeted application, whithout the need to gel either the internal or external phase., (Copyright © 2018 Elsevier Ltd. All rights reserved.)

Iron deficiency is a major global human health concern. Encapsulation of iron in functional food products may help to solve this problem. However, iron is highly reactive and may promote rapid lipid oxidation in fatty foods. In this study, the effect of ferrous sulfate (0.1 to 0.5 wt%) and rice bran stearin (0 or 30 wt%) on the physical properties, oxidative stability, and encapsulation efficiency of 20 wt% water-in-oil (W/O) emulsions stabilized with polyglycerol polyricinoleate was investigated. In the presence of rice bran stearin crystals in the continuous oil phase, W/O emulsions had smaller mean droplet diameters (d ∼ 250 nm) and better physical stability than its absence (d ∼ 330 nm). An increase in the ferrous sulfate concentration in the water droplets led to a decrease in the oxidative stability of the W/O emulsions. However, the presence of rice bran stearin significantly (P ≤ 0.05) improved their oxidative stability. Moreover, addition of rice bran stearin also significantly (P ≤ 0.05) improved the encapsulation efficiency and delayed ferrous sulfate release from the W/O emulsions. The impact of pH and ionic strength on the encapsulation efficiency of the W/O emulsion was also investigated. Ionic strength affected the encapsulation efficiency much more than pH. The W/O emulsions created in the present study may be useful for the encapsulation and delivery of iron and other water-soluble nutrients into food products., Practical Application: Water-in-oil (W/O) emulsions may be used to encapsulate, protect, and deliver water-soluble bioactive compounds or nutrients into food products. In this study, W/O emulsions stabilized using an oil-soluble surfactant (polyglycerol polyricinoleate, PGPR) and fat crystal network (rice bran stearin) were shown to be useful for encapsulation and delivery of iron into foods. This strategy may be a promising approach to reduce iron deficiency, a major nutritional deficiency for people with inadequate food supplies., (© 2018 Institute of Food Technologists®.)

The future of this study was to prepare a natural pesticide which will not harm the environment and yet control pests. Neem gum nano formulation (NGNF), a novel biopesticide prepared from the Neem gum extract (Azadirachta indica) (NGE) was evaluated for its antifeedant, larvicidal and pupicidal activities against Helicoverpa armigera (Hub.) and Spodoptera litura (Fab.) at 100ppm. The NGNF showed significant (100%) antifeedant, larvicidal and pupicidal activities against H. armigera and S. litura. The LC 50 values of 10.20, 12.49 and LC 90 values of 32.68, 36.68ppm on H. armigera and S. litura, respectively at 100ppm. The NGNF treatments showed differences in the activities of detoxifying enzymes, carboxylesterases, glucosidases and glutathione S-transferases in the larval gut. Earthworm toxicity illustrated that 6.25ppm of chemical insecticides (cypermethrin) varied widely in their contact toxicities compared to 100ppm of NGNF and control in both contact filter paper and artificial soil test. The NGNF were characterized and confirmed by FTIR, XRD, SEM and EDX analysis. Ten compounds were identified from the Neem gum extract (NGE) by Gas Chromatography-Mass Spectrometry (GC-MS) analysis. The major compounds were fatty acids like Hexadecanoic acid, oleic acid, and ricinoleic acid. NGNF could be used as an agent to prepare novel bio-pesticides formulations., (Copyright © 2017 Elsevier B.V. All rights reserved.)

Water-in-oil-in-water (W/O/W) double emulsions based on crystallized oils were prepared and the release kinetics of magnesium ions from the internal to the external aqueous phase was investigated at T=4°C, for different crystallized lipophilic matrices. All the emulsions were formulated using the same surface-active species, namely polyglycerol polyricinoleate (oil-soluble) and sodium caseinate (water-soluble). The external aqueous phase was a lactose or glucose solution at approximately the same osmotic pressure as that of the inner droplets, in order to avoid osmotic water transfer phenomena. We investigated two types of crystallized lipophilic systems: one based on blends of cocoa butter and miglyol oil, exploring a solid fat content from 0 to 90% and the other system based on milk fat fractions for which the solid fat content varies between 54 and 86%. For double emulsions based on cocoa butter/miglyol oil, the rate of magnesium release was gradually lowered by increasing the % of fat crystals i.e. cocoa butter, in agreement with a diffusion/permeation mechanism. However for double emulsions based on milk fat fractions, the rate of magnesium release was independent of the % of fat crystals and remains the one at t=0. This difference in diffusion patterns, although the solid content is of the same order, suggests a different distribution of fat crystals within the double globules: a continuous fat network acting as a physical barrier for the diffusion of magnesium for double emulsions based on cocoa butter/miglyol oil and double globule/water interfacial distribution for milk fat fractions based double emulsions, through the formation of a crystalline shell allowing an effective protection of the double globules against diffusion of magnesium to the external aqueous phase., (Copyright © 2017 Elsevier Inc. All rights reserved.)

The structures of micelles and microemulsions consisting of polyglycerol polyricinoleate (PGPR) were investigated by small-angle X-ray scattering (SAXS) and rheological measurements. The SAXS results show that amphiphilic PGPR molecules form stable micelles in glycerol. When vitamin E is added to the PGPR micelles, it is encapsulated in the micelles and forms an emulsion. These micelles are stable towards mechanical shearing up to a shear rate of 1000 s -1 , with shear thinning occurring in the emulsion above 100 s -1 , indicating that the emulsion may undergo break up by shearing, but recovers the structure by releasing shear strain.

An environment-friendly, free of solvent, process for the synthesis of (R)- and (S)-ricinoleic acid amides has been developed. Starting from methyl ricinoleates and pyrrolidine or ethanolamine, the corresponding amides were obtained with yields ranging from 83-88%. Among 12 synthesized derivatives of ricinoleic acid, including the starting methyl esters, amides, and their acetates, nine compounds were obtained and tested for the first time. Studies on ricinoleic acid derivatives cytotoxicity showed that methyl esters were the least cytotoxic compounds and modification of their structure resulted in increasing cytotoxicity of the obtained products against both cancer cells and normal lymphocytes. Both enantiomers of the ethanolamine-derived amides showed the most promising anticancer potential., (© 2017 Wiley Periodicals, Inc.)

We show that the rigidity and microstructure of water-in-oil (W/O) emulsions depend on the ability of oil-soluble emulsifiers to enhance the crystallization of fats on the surface of dispersed aqueous droplets. In test emulsions consisting of hydrogenated soy oil (HSO) in liquid canola oil (CO) and a dispersed aqueous phase representing up to 20wt% of the emulsion, use of glycerol monooleate (GMO) promoted oil-water interfacial crystallization whereas polyglycerol polyricinoleate (PGPR) resulted in HSO crystallization in the continuous phase only. By removing the confounding effects of droplet size and solid fat content, GMO-covered emulsion droplets were shown to behave as active fillers as they interacted with the surrounding fat crystal matrix and increased emulsion rigidity. By contrast, the PGPR-stabilized droplets only weakly associated with the matrix and did not significantly alter emulsion rheology, hence these were inactive fillers. This study shows that by simply changing emulsifier type, it is possible to alter the magnitude of the association between the dispersed droplets and surrounding fat crystals and, by extension, tailor the texture and rigidity of fat crystal-stabilized water-in-oil emulsions., (Copyright © 2017. Published by Elsevier Ltd.)

A stable and bio-compatible w/o nano-emulsion was developed as adjuvant for foot and mouth disease (FMD) vaccine with isopropyl myristate as oil phase, polyglycerol polyricinoleate, and Tween 80 as surfactants. Dissolving Tween 80 in aqueous phase decreased the droplet size and improved stability of the emulsion through narrowing size distribution, increasing viscosity, and reducing the interfacial tension between oil and water. The nano-emulsion was then formulated with inactivated FMD virus and ovalbumin to investigate its potential application as an adjuvant. Compared with commercial ISA-206 adjuvant, the novel w/o nano-emulsion was able to induce both humoral- and cell-mediated immune response.

Poly(anhydride) are unstable and prone to hydrolytic degradation and depolymerisation via anhydride interchange. They are stored at -20°C, packed under inert atmosphere until use. We synthesized a new poly(anhydride) from ricinoleic (RA) and sebacic (SA) acid with alternating ester-anhydride structure that is stable at 25°C for over 18months. The copolymer is also stable in chloroform solution and under γ-irradiation. The polymer hydrolyses through anhydride cleavage lasting ~7days to form oligoesters, which are stable for >30days. The release of gentamycin from the synthesized alternate polymer matrix is sustained compared to the random copolymer., (Copyright © 2016 Elsevier B.V. All rights reserved.)

Estolides of ricinoleic acid (RA) have been used as lubricants and pigment dispersant in many industries. In this paper, functional acid ionic liquids (ILs) were firstly used as catalysts to prepare RA estolides by the esterification of RAs in solvent-free system. Different ILs were used as catalysts for the esterification. Effect of reaction variables (IL amount, reaction temperature and reaction time) on the esterification were also investigated and optimized using response surface methodology (RSM). Among all tested ILs, [BSO 3 HMIM]TS showed the best performance for the esterification. Arrhenius equation for the esterification was lnV 0 =14.897-7558.7/T, and the activation energy (Ea) was 62.84 kJ/mol. A high degree of polymerization with an acid value of 48.0±2.5 mg KOH/g was achieved at the optimized conditions (IL load 12%, reaction temperature 140°C, and reaction time 12 h). The effect of reaction variables on the esterification decreased in the order of catalyst loading of IL > reaction temperature > reaction time.

In the present study, rice bran stearin was used to improve the physical stability and encapsulation efficiency of water-in-oil (W/O) emulsions fabricated from rice bran oil and polyglycerol polyricinoleate ester (PGPR). In the absence of rice bran stearin, the emulsions were highly unstable to phase separation with an oil layer forming on their surfaces. Phase separation was delayed by increasing the PGPR concentration because this reduced the water droplet size. Phase separation could be completely inhibited by replacement of 30 to 45wt% of rice bran oil with rice bran stearin due to the formation of a semi-solid fat crystal network that prevented droplet movement. Moreover, addition of rice bran stearin delayed the release of ferrous sulfate from the W/O emulsions. These results demonstrate that rice bran stearin can be used to improve the stability and encapsulation efficiency of W/O emulsions and reduce the level of PGPR required to stabilize them., (Copyright © 2017 Elsevier Ltd. All rights reserved.)

The gelating abilities of ricinelaidic acid (d-REA), the trans-isomer of ricinoleic acid (d-RA), and a series of its alkylammonium and alkane-α,ω-diammonium salts have been examined in a wide range of organic liquids. The gelation efficiency of the trans acid is much better than that of the cis, although neither is as efficient as is the completely saturated molecular gelator analogue, (R)-12-hydroxystearic acid (d-12HSA). The formation of ammonium salts also improves the gelation ability of d-REA in high polarity liquids. The gelating properties are highly dependent upon the chain length of the alkyl group of the alkylammonium salts, but not very dependent on the chain length of the alkane-α,ω-diammonium salts. Structural insights from Fourier transform infrared spectroscopy and powder X-ray diffraction indicate that the absence or presence of unsaturation, the incorporation of (charged) ammonium centers, and the different chain lengths of the alkylammonium salts lead to different packing arrangements and different strengths of H-bonding interactions within the gel assemblies of the d-REA derivatives. Insights into the relationships among the various systematic structural changes to d-REA and the properties of their aggregated structures, including the gel states, are provided., (© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Ricinoleic acid as the characteristic fatty acid of Secale cornutum oil is a good marker for Secale cornutum impurities in cereal. The presented screening for ricinoleic acid in rye by high-performance thin-layer chromatography with fluorescence detection (HPTLC-FLD) offers a selective and sensitive method for the determination of Secale cornutum and is very different from existing gas chromatographic analyses. Lipid extraction was followed by transesterification and solid-phase extraction cleanup; thereafter, extracts were selectively derivatized with 2-naphthoyl chloride and analyzed by HPTLC-FLD with silica gel plates and cyclohexane/diisopropyl ether/formic acid (86:14:1, v/v/v) as mobile phase. For quantitation, the enhanced fluorescence was scanned at 280/>340 nm. Limits of detection and quantitation of 0.1 and 0.4 mg ricinoleic acid/kg of rye were obtained, which enables the determination of Secale cornutum far below the maximum admitted level. With near-100% recoveries and low standard deviations at relevant spiking levels, reliable results were guaranteed.

A series of novel ricinoleic acid based lipoamino acid derivatives were synthesized from (Z)-methyl-12-aminooctadec-9-enoate and different l-amino acids (glycine, alanine, phenyl alanine, valine, leucine, isoleucine, proline and tryptophan). The structures of all the prepared compounds were characterized by 1 H NMR, 13 C NMR and mass spectral studies. The title compounds were evaluated for their antimicrobial and anti-biofilm activities. Among all the derivatives, compound 7a (Z)-methyl-12-(2-aminoacetamido)octadec-9-enoate exhibited promising antibacterial activity (MIC, 3.9-7.8μg/mL) and compounds 7b (Z)-methyl 12-(2-aminopropanamido)octadec-9-enoate and 7g (Z)-methyl-12-(pyrrolidine-2-carboxamido)octadec-9-enoate exhibited moderate activity (MIC, 7.8-31.2μg/mL) selectively against four different Gram-positive bacterial strains such as Staphylococcus aureus MTCC 96, Bacillus subtilis MTCC 121, S. aureus MLS-16 MTCC 2940, Micrococcus luteus MTCC 2470. These compounds also exhibited excellent antifungal activity against studied fungal strains. Further, the compounds 7a, 7b and 7g were also screened for anti-biofilm activity. Among these lipoamino acid derivatives, compound 7a exhibited good anti-biofilm activity (IC 50 , 1.9-4.1μg/mL) against four Gram-positive bacterial strains., (Copyright © 2016 Elsevier Ltd. All rights reserved.)

The request for new flavourings increases every year. Consumer perception that everything natural is better is causing an increase demand for natural aroma additives. Biotechnology has become a way to get natural products. γ-Decalactone is a peach-like aroma widely used in dairy products, beverages and others food industries. In more recent years, more and more studies and industrial processes were endorsed to cost-effect this compound production. One of the best-known methods to produce γ-decalactone is from ricinoleic acid catalyzed by Yarrowia lipolytica, a generally regarded as safe status yeast. As yet, several factors affecting γ-decalactone production remain to be fully understood and optimized. In this review, we focus on the aromatic compound γ-decalactone and its production by Y. lipolytica. The metabolic pathway of lactone production and degradation are addressed. Critical analysis of novel strategies of bioprocess engineering, metabolic and genetic engineering and other strategies for the enhancement of the aroma productivity are presented.

Castor oil methyl ester is a kind of biodiesel from castor oil. However, in those previous methods for biodiesel preparation using castor oil as feedstock, glycerol was the main by-product, which had a strong blocking effect on the immobilized enzyme activity and affected the mass transfer of reaction system. For avoiding the negative effect of glycerol on the enzymatic esterification, biodiesel was prepared using ricinoleic acid (RA) as acyl donor. Enzyme screening was also studied, and the effects of reaction temperature, molar ratio of ricinoleic acid and methanol, enzyme load, and reaction time, on the preparation of castor methyl ester were also evaluated. Response surface methodology (RSM) was used to optimize the interaction effect of reaction variables (reaction temperature (30-70°C), enzyme load (2-7%; relative to the weight of total substrates), molar ratio of methanol to ricinoleic acid (2:1-10:1), and reaction time (0.5-2.5 h)) on the acid value (AV) and the degree of esterification (DE). Validation of the RSM model was verified by the good agreement between the experimental and the predicted values of AV and DE. The optimum preparation conditions were as follows: reaction temperature, 48.2°C; enzyme load, 5.8%; molar ratio of methanol to ricinoleic acid, 5.56:1; reaction time, 2.36 h. Under these conditions, the AV and DE of the esterification reaction are 10.36±1.05 mgKOH/g and 94.03±0.60%, respectively. The relationship between initial reaction rate and temperature was also established, and the activation energy (Ea) of the enzymatic esterification is 33.87 KJ/mol.

Objective: The overall objective of this work is to determine the percutaneous absorption of chlorpromazine hydrochloride from pluronic lecithin organogels (PLO gels) and verify the suitability of topically applied chlorpromazine hydrochloride PLO gels for use in hospice patients for relieving symptoms such as vomiting and nausea during the end stages of life., Methods: PLO gels of chlorpromazine hydrochloride were prepared using isopropyl palmitate (IPP) or ricinoleic acid (RA) as oil phase. In vitro percutaneous absorption of chlorpromazine hydrochloride was assessed through porcine ear and human abdominal skin. Further, the theoretical steady state plasma concentration (Css) of chlorpromazine was calculated from the flux values., Results: The pH, viscosity, and stability of both PLO gels prepared with IPP and RA were comparable. The thixotropic property of RA PLO gel was found to be better than that of IPP PLO gel. The permeation of chlorpromazine hydrochloride was higher from RA PLO gel than from IPP PLO gel and pure drug solution. Theoretical Css of chlorpromazine from pure drug solution, IPP PLO gel and RA PLO gel were found to be 1.05, 1.20, and 1.50 ng/ml, respectively. PLO gels only marginally increased the flux and theoretical Css of chlorpromazine., Conclusion: From this study, it is clearly evident that PLO gels fail to achieve required systemic levels of chlorpromazine following topical application. Chlorpromazine PLO gel may not be effective in treating nausea and vomiting for hospice patients with swallowing difficulties.