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Phytosterols-induced viscoelasticity of oleogels prepared by using monoglycerides

Bin Sintang MD, Danthine S, Brown A, Van de Walle D, Patel AR, Tavernier I, et al.

Food Res Int, 2017 10;100(Pt 1):832-840.
PMID: 28873756 DOI: 10.1016/j.foodres.2017.07.079

Monoglycerides (MGs) and phytosterols (PS) are known to form firm oleogels with liquid oil. However, the oleogels are prone to undergo polymorphic transition over time that lead to crystals' aggregation thus, compromises physical properties. Thus, we combined MGs with PS to control the crystallization and modify the morphology of the combination oleogels, as both components are reported to interact together. The oleogels were prepared at different ratio combinations and characterized in their rheological, thermal, morphology, and diffraction properties. The results showed that the 8:2 MGP:PS exhibited higher storage modulus (G') than the MGP mono-component. The combination oleogels exhibited effects on the crystallization and polymorphic transition. Consequently, the effects led to change in the morphology of the combination oleogels which was visualized using optical and electron microscope. The resultant effect on the morphology is associated with crystal defect. Due to observable crystals of MGP and PS, it is speculated that the combination oleogels formed a mixed crystal system. This was confirmed with diffraction analysis in which the corresponding peaks from MGP and PS were observed in the combination oleogels. However, the 8:2 oleogel exhibited additional peak at 35.41Å. Ultimately, the 8:2 was the optimum combination observed in our study. Interestingly, this combination is inspired by nature as sterols (phytosterols) are natural component of lipid membrane whilst MGP has properties similar to phospholipids. Hence, the results of our study not only beneficial for oil structuring, but also for the fields of biophysical and pharmaceutical.

Matched MeSH terms: Monoglycerides/chemistry*
Modulating the crystallization of phytosterols with monoglycerides in the binary mixture systems: mixing behavior and eutectic formation

Bin Sintang MD, Danthine S, Khalenkow D, Tavernier I, Tzompa Sosa DA, Julmohammad NB, et al.

Chem Phys Lipids, 2020 08;230:104912.
PMID: 32371001 DOI: 10.1016/j.chemphyslip.2020.104912

Phytosterols (PSs) are insoluble in water and poorly soluble in oil, which hampers their potential as cholesterol level regulator in human. To mitigate this problem, monoglycerides (MGs) were used to modulates the crystallization behavior of PSs. Therefore, the understanding on mixing behavior provides the insight into different aspects of crystallization and the resultant effects. The effects on thermal, morphology, diffraction, and spectroscopy behavior were investigated for binary mixtures of 11 different ratios (100:0 to 0:100 MGs:PSs). The phase behavior of binary mixtures of commercial MGs and PSs exhibited complexity with the formation of eutectic mixtures at 90:10 and 80:20 (MGs:PSs) combinations. These combinations revealed a single melting profile and reduced melting enthalpy, though after a month of storage at 5 °C. Conversely, two separate melting regions were observed in others. Furthermore, powder X-ray diffraction (PXRD) analysis of selected combinations revealed a change in crystalline forms with changes in the peaks located between 18-19° (2θ) and 25-26° (2θ). Accordingly, Raman spectroscopy results revealed changes in intensities and peak shape. Therefore, the change in crystalline forms or behavior correlated well to the change in thermal properties. Overall, the characterizations revealed the formation of eutectic mixtures between MGs and PSs at 90:10 and 80:20 (MGs:PSs) in which MGs modified the crystallization of PSs and changed the crystal forms thus, thermal behaviors. This study provides new insight into the mixing behavior of MGs and PSs which supports other research. Therefore, the results of this study are beneficial for the improvement of formulation of phytosterols in food and pharmaceutical products. Nonetheless, this study reveals a simple technique to alter crystal forms of phytosterols through simple complexation with monoglycerides.

Matched MeSH terms: Monoglycerides
Effect of blending and emulsification on thermal behavior, solid fat content, and microstructure properties of palm oil-based margarine fats

Saadi S, Ariffin AA, Ghazali HM, Miskandar MS, Abdulkarim SM, Boo HC

J Food Sci, 2011 Jan-Feb;76(1):C21-30.
PMID: 21535649 DOI: 10.1111/j.1750-3841.2010.01922.x

The ability of palm oil (PO) to crystallize as beta prime polymorph has made it an attractive option for the production of margarine fat (MF). Palm stearin (PS) expresses similar crystallization behavior and is considered one of the best substitutes of hydrogenated oils due to its capability to impart the required level of plasticity and body to the finished product. Normally, PS is blended with PO to reduce the melting point at body temperature (37 °C). Lipid phase, formulated by PO and PS in different ratios were subjected to an emulsification process and the following analyses were done: triacylglycerols, solid fat content (SFC), and thermal behavior. In addition, the microstructure properties, including size and number of crystals, were determined for experimental MFs (EMFs) and commercial MFs (CMFs). Results showed that blending and emulsification at PS levels over 40 wt% significantly changed the physicochemical and microstructure properties of EMF as compared to CMF, resulting in a desirable dipalmitoyl-oleoyl-glycerol content of less than 36.1%. SFC at 37 °C, crystal size, crystal number, crystallization, and melting enthalpies (ΔH) were 15%, 5.37 μm, 1425 crystal/μm(2), 17.25 J/g, and 57.69J/g, respectively. All data reported indicate that the formation of granular crystals in MFs was dominated by high-melting triacylglycerol namely dipalmitoyl-oleoyl-glycerol, while the small dose of monoacylglycerol that is used as emulsifier slowed crystallization rate. Practical Application: Most of the past studies were focused on thermal behavior of edible oils and some blends of oils and fats. The crystallization of oils and fats are well documented but there is scarce information concerning some mechanism related to crystallization and emulsification. Therefore, this study will help to gather information on the behavior of emulsifier on crystallization regime; also the dominating TAG responsible for primary granular crystal formations, as well as to determine the best level of stearin to impart the required microstructure properties and body to the finished products.

Matched MeSH terms: Monoglycerides/chemistry*
Fulltext Pharmacophore modelling of vanillin derivatives, favipiravir, chloroquine, hydroxychloroquine, monolaurin and tetrodotoxin as MPro inhibitors of severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2)

Law WY, Asaruddin MR, Bhawani SA, Mohamad S

BMC Res Notes, 2020 Nov 11;13(1):527.
PMID: 33176880 DOI: 10.1186/s13104-020-05379-6

OBJECTIVES: The aim of this study was to use Ligand-based pharmacophore modelling approach for four established antiviral drugs, namely remdesivir, lopinavir, ritonavir and hydroxychloroquine for COVID-19 inhibitors as training sets. In this study Twenty vanillin derivatives together with monolaurin and tetrodotoxin were used as test sets to evaluate as potential SARS-CoV-2 inhibitors. The Structure-based pharmacophore modelling approach was also performed using 5RE6, 5REX and 5RFZ in order to analyse the binding site and ligand-protein complex interactions.
RESULTS: The pharmacophore modelling mode of 5RE6 displayed two Hydrogen Bond Acceptors (HBA) and one Hydrophobic (HY) interaction. Besides, the pharmacophore model of 5REX showed two HBA and two HY interactions. Finally, the pharmacophore model of 5RFZ showed three HBA and one HY interaction. Based on ligand-based approach, 20 Schiff-based vanillin derivatives, showed strong MPro inhibition activity. This was due to their good alignment and common features to PDB-5RE6. Similarly, monolaurin and tetrodotoxin displayed some significant activity against SARS-CoV-2. From structure-based approach, vanillin derivatives (1) to (12) displayed some potent MPro inhibition against SARS-CoV-2. Favipiravir, chloroquine and hydroxychloroquine also showed some significant MPro inhibition.

Matched MeSH terms: Monoglycerides/pharmacology; Monoglycerides/chemistry
Fulltext The bioaccessibility of eicosapentaenoic acid was higher from phospholipid food products than from mono- and triacylglycerol food products in a dynamic gastrointestinal model

Domoto N, Koenen ME, Havenaar R, Mikajiri A, Chu BS

Food Sci Nutr, 2013 Nov;1(6):409-15.
PMID: 24804049 DOI: 10.1002/fsn3.58

The bioaccessibility of eicosapentaenoic acid (EPA) in the forms of monoacylglycerol (EPA-MAG), triacylglycerol (EPA-TAG), and phospholipid (EPA-PL) during gastrointestinal passage was compared in this study using a dynamic gastrointestinal model (TIM system). The TIM system simulated the average upper gastrointestinal tract conditions of healthy human adults after intake of a meal (fed state conditions). In this study, the three EPA-rich oils were separately homogenized with full fat milk to obtain oil-in-water emulsions. Plain yogurt was added into the mixture at an emulsion/yogurt ratio of 4:1 (w/w) as the food matrix of the test products. The results show that the test meals containing EPA-PL left the stomach compartment most efficiently in comparison with the gastric emptying of EPA-MAG and EPA-TAG. The PLs also showed a significantly (P < 0.05) higher bioaccessibility of EPA (75-80%) in comparison with MAG (30%) and TAG (38%). The better gastric emptying of EPA-PL was likely related to the more stable emulsion of EPA-PL in the test meal. EPA-PL was delivered within the meal matrix into the duodenum instead of floating on the top of the test meal matrix. EPA-MAG had the highest amount of EPA that did not leave the stomach (68% of the test meal). The results from this work indicate that EPA-PL is a more effective form of EPA for a higher lipid bioaccessibility than MAG and TAG under the test conditions.

Matched MeSH terms: Monoglycerides
Selective glycerol esterification over organomontmorillonite catalysts

Wibowo TY, Ridzuan Zakaria, Ahmad Zuhairi Abdullah

Sains Malaysiana, 2010;39.

Organomontmorillonites were synthesized by grafting cationic surfactants i.e quaternary ammonium compounds into the interlayer space and were characterized using XRD, FTIR and N2 adsorption/ desorption analysis. The organomontmorillonites were applied as catalyst for the esterification of glycerol (GL) with lauric acid (LA). The catalyst which had symmetrical onium salts (tetrabuthylammoniumbromide, TBAB) gave higher activity than that of unsymmetrical onium salts (cetyltrimethylammoniumbromide, CTAB). Over the TBAB-montmorillonite catalyst, glycerol monolaurate was obtained with a selectivity of about 80%, a lauric acid conversion of about 71% and a glycerol monolaurate yield of about 57%.

Matched MeSH terms: Monoglycerides
Fulltext Lipidomic Biomarkers in Polycystic Ovary Syndrome and Endometrial Cancer

Shafiee MN, Ortori CA, Barrett DA, Mongan NP, Abu J, Atiomo W

Int J Mol Sci, 2020 Jul 03;21(13).
PMID: 32635401 DOI: 10.3390/ijms21134753

Women with polycystic ovary syndrome (PCOS) are more likely to develop endometrial cancer (EC). The molecular mechanisms which increase the risk of EC in PCOS are unclear. Derangements in lipid metabolism are associated with EC, but there have been no studies, investigating if this might increase the risk of EC in PCOS. This was a cross-sectional study of 102 women in three groups of 34 (PCOS, EC and controls) at Nottingham University Hospital, UK. All participants had clinical assessments, followed by obtaining plasma and endometrial tissue samples. Lipidomic analyses were performed using liquid chromatography (LC) coupled with high resolution mass spectrometry (HRMS) and the obtained lipid datasets were screened using standard software and databases. Using multivariate data analysis, there were no common markers found for EC and PCOS. However, on univariate analyses, both PCOS and EC endometrial tissue samples showed a significant decrease in monoacylglycerol 24:0 and capric acid compared to controls. Further studies are required to validate these findings and investigate the potential role of monoacylglycerol 24:0 and capric acid in the link between PCOS with EC.

Matched MeSH terms: Monoglycerides/metabolism
Structure-property studies of thermoplastic and thermosetting polyurethanes using palm and soya oils-based polyols

Mohammed IA, Al-Mulla EA, Kadar NK, Ibrahim M

J Oleo Sci, 2013;62(12):1059-72.
PMID: 24292358

Palm and soya oils were converted to monoglycerides via transesterification of triglycerides with glycerol by one step process to produce renewable polyols. Thermoplastic polyurethanes (TPPUs) were prepared from the reaction of the monoglycerides which act as polyol with 4,4'-methylenediphenyldiisocyanate (MDI) whereas, thermosetting polyurethanes (TSPUs) were prepared from the reaction of glycerol, MDI and monoglycerides in one pot. Characterization of the polyurethanes was carried out by FT-IR, (1)H NMR, and iodine value and sol-gel fraction. The TSPUs showed good thermal properties compared to TPPUs as well as TSPUs exhibits good properties in pencil hardness and adhesion, however poorer in flexural and impact strength compared to TPPUs. The higher percentage of cross linked fraction, the higher degree of cross linking occurred, which is due to the higher number of double bond presents in the TSPUs. These were reflected in iodine value test as the highest iodine value of the soya-based thermosetting polyurethanes confirmed the highest degree of cross linking. Polyurethanes based on soya oil showed better properties compared to palm oil. This study is a breakthrough development of polyurethane resins using palm and soya oils as one of the raw materials.

Matched MeSH terms: Monoglycerides
Fulltext Fatty Acid Profile, Phytochemicals, and Other Substances in Canarium odontophyllum Fat Extracted Using Supercritical Carbon Dioxide

Khoo HE, Azlan A, Abd Kadir NAA

Front Chem, 2019;7:5.
PMID: 30766864 DOI: 10.3389/fchem.2019.00005

This study aims to identify potential phenolic compounds, terpenoids, and other phytochemicals, as well as fatty acid profile and peptides in Canarium odontophyllum (CO) oil and oleoresin, extracted using supercritical carbon dioxide. LC-ESI-MS was applied in separation and tentative identification of phytochemicals in CO oil and oleoresin. Based on the results, 11 common fatty acids and their isomers, monoglycerides, diglycerides, as well as other types of lipid, were tentatively identified in the CO oil and oleoresin. The identified fatty acids consisted of saturated fatty acids (C8-C16), monounsaturated fatty acids (C16:1 and C18:1), polyunsaturated fatty acids (C18:2, C18:3, C18:4, and C20:3), and other unclassified fatty acids. The tentatively identified phenolic compounds were phenolic acids, flavonoids, lignans, and a phenolic monoester. Triterpenes, sesquiterpenes, and apocarotenoids were the terpenoids found in CO oil and oleoresin. Besides these typical bioactives, some volatiles, aromatic compounds, peptides, and other known and unknown phytochemicals were also tentatively identified in the oil and oleoresin of CO. Some of these compounds are new compounds identified in CO oil and oleoresin, which are not found in many other fruit oils. Although CO oil and oleoresin contain a small number of phytochemicals, their contribution as antioxidants may prevent several diseases. In this study, we hypothesized that CO oleoresin contains certain types of fatty acids that render its semi-solid together with other chemical components which are not found in CO oil. This is the first study that tentatively identified fatty acids, peptides, and potential phytochemicals in CO oil and oleoresin using LC-ESI-MS.

Matched MeSH terms: Monoglycerides