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Enhanced halophilic lipase secretion by Marinobacter litoralis SW-45 and its potential fatty acid esters release

Musa H, Hafiz Kasim F, Nagoor Gunny AA, Gopinath SCB, Azmier Ahmad M

J Basic Microbiol, 2019 Jan;59(1):87-100.
PMID: 30270443 DOI: 10.1002/jobm.201800382

An approach was made to enhance the halophilic lipase secretion by a newly isolated moderate halophilic Marinobacter litoralis SW-45, through the statistical optimization of Plackett-Burman (PB) experimental design and the Face Centered Central Composite Design (FCCCD). Initially, PB statistical design was used to screen the medium components and process parameters, while the One-factor-at-a-time technique was availed to find the optimum level of significant parameters. It was found that MgSO4 · 7H2 O, NaCl, agitation speed, FeSO4 · 7H2 O, yeast extract and KCl positively influence the halophilic lipase production, whereas temperature, carbon source (maltose), inducer (olive oil), inoculum size, and casein-peptone had a negative effect on enzyme production. The optimum level of halophilic lipase production was obtained at 3.0 g L-1 maltose, 1% (v/v) olive oil, 30 °C growth temperature and 4% inoculum volume (v/v). Further optimization by FCCCD was revealed 1.7 folds improvement in the halophilic lipase production from 0.603 U ml-1 to 1.0307 U ml-1 . Functional and biochemical characterizations displayed that the lipase was significantly active and stable in the pH ranges of 7.0-9.5, temperature (30-50 °C), and NaCl concentration (0-21%). The lipase was maximally active at pH 8.0, 12% (w/v) NaCl, and 50 °C temperature. Besides, M. litoralis SW-45 lipase was found to possess the promising industrial potential to be utilized as a biocatalyst for the esterification.

Matched MeSH terms: Esterification
Fulltext An Improved Nanoemulsion Formulation Containing Kojic Monooleate: Optimization, Characterization and In Vitro Studies

Roselan MA, Ashari SE, Faujan NH, Mohd Faudzi SM, Mohamad R

Molecules, 2020 Jun 04;25(11).
PMID: 32512808 DOI: 10.3390/molecules25112616

Tyrosinase inhibitors have become increasingly important targets for hyperpigmentation disease treatment. Kojic monooleate (KMO), synthesized from the esterification of kojic acid and oleic acid, has shown a better depigmenting effect than kojic acid. In this study, the process parameters include the speed of high shear, the time of high shear and the speed of the stirrer in the production of nanoemulsion containing KMO was optimized using Response Surface Methodology (RSM), as well as evaluated in terms of its physicochemical properties, safety and efficacy. The optimized condition for the formulation of KMO nanoemulsion was 8.04 min (time of high shear), 4905.42 rpm (speed of high shear), and 271.77 rpm (speed of stirrer), which resulted in a droplet size of 103.97 nm. An analysis of variance (ANOVA) showed that the fitness of the quadratic polynomial fit the experimental data with large F-values (148.79) and small p-values (p < 0.0001) and an insignificant lack of fit. The optimized nanoemulsion containing KMO with a pH value of 5.75, showed a high conductivity value (3.98 mS/cm), which indicated that the nanoemulsion containing KMO was identified as an oil-in-water type of nanoemulsion. The nanoemulsion remains stable (no phase separation) under a centrifugation test and displays accelerated stability during storage at 4, 25 and 45 °C over 90 days. The cytotoxicity assay showed that the optimized nanoemulsion was less toxic, with a 50% inhibition of cell viability (IC50) > 500 μg/mL, and that it can inhibit 67.12% of tyrosinase activity. This study reveals that KMO is a promising candidate for the development of a safe cosmetic agent to prevent hyperpigmentation.

Matched MeSH terms: Esterification
Radical scavenging activity of lipophilized products from transesterification of flaxseed oil with cinnamic acid or ferulic acid

Choo WS, Birch EJ, Stewart I

Lipids, 2009 Sep;44(9):807-15.
PMID: 19727883 DOI: 10.1007/s11745-009-3334-2

Lipase-catalyzed transesterification of flaxseed oil with cinnamic acid (CA) or ferulic acid (FA) using an immobilized lipase from Candida antarctica (E.C. 3.1.1.3) was conducted to evaluate whether the lipophilized products provided enhanced antioxidant activity in the oil. Lipase-catalyzed transesterification of flaxseed oil with CA or FA produced a variety of lipophilized products (identified using ESI-MS-MS) such as monocinnamoyl/feruloyl-diacylglycerol, dicinnamoyl-monoacylglycerol and monocinnamoyl-monoacylglycerol. The free radical scavenging activity of the lipophilized products of lipase-catalyzed transesterification of flaxseed oil with CA or FA toward 2,2-diphenyl-1-picrylhydrazyl radical (DPPH.) were both examined in ethanol and ethyl acetate. The polarity of the solvents proved important in determining the radical scavenging activity of the substrates. Unesterified FA showed the highest free radical scavenging activity among all substrates tested while CA had negligible activity. The esterification of CA or FA with flaxseed oil resulted in significant increase and decrease in the radical scavenging activity compared with the native phenolic acid, respectively. Based on the ratio of a substrate to DPPH. concentration, lipophilized FA was a much more efficient free radical scavenger compared to lipophilized CA and was able to provide enhanced antioxidant activity in the flaxseed oil. Lipophilized cinnamic acid did not provide enhanced radical scavenging activity in the flaxseed oil as the presence of natural hydrophilic antioxidants in the oil had much greater radical scavenging activity.

Matched MeSH terms: Esterification
Synthesis of conjugated linoleic acid-rich triacylglycerols by immobilized mutant lipase with excellent capability and recyclability

Lian W, Li D, Zhang L, Wang W, Faiza M, Tan CP, et al.

Enzyme Microb Technol, 2018 Oct;117:56-63.
PMID: 30037552 DOI: 10.1016/j.enzmictec.2018.06.007

Conjugated linoleic acid (CLA)-rich triacylglycerols (TAG) have received significant attention owing to their health promoting properties. In this study, CLA-rich TAG were successfully synthesized by an immobilized mutant lipase (MAS1-H108A)-catalyzed esterification of CLA-rich fatty acids and glycerol under vacuum. MAS1-H108A was first immobilized onto ECR1030 resin. Results showed that the lipase/support ratio of 41 mg/g was suitable for the immobilization and the thermostability of immobilized MAS1-H108A was greatly enhanced. Subsequently, the immobilized MAS1-H108A was employed for the synthesis of CLA-rich TAG and 95.21% TAG with 69.19% CLA was obtained under the optimized conditions. The TAG content (95.21%) obtained by immobilized MAS1-H108A is the reported highest value thus far, which was significantly higher than that (9.26%) obtained by Novozym 435 under the same conditions. Although the TAG content comparable to the results obtained in this study could also be obtained by Novozym 435, the used enzyme amount is approximately 5-fold of the immobilized MAS1-H108A. Additionally, the immobilized MAS1-H108A exhibited excellent recyclability during esterification retaining 95.11% of its initial activity after 10 batches. Overall, such immobilized mutant lipase with superior esterification activity and recyclability has the potential to be used in oils and fats industry.

Matched MeSH terms: Esterification
Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid

El-Boulifi N, Ashari SE, Serrano M, Aracil J, Martínez M

Enzyme Microb Technol, 2014 Feb 5;55:128-32.
PMID: 24411455 DOI: 10.1016/j.enzmictec.2013.10.009

The aim of this work was the synthesis of a novel hydroxyl-fatty acid derivative of kojic acid rich in kojic acid monoricinoleate (KMR) which can be widely used in the cosmetic and food industry. The synthesis of KMR was carried out by lipase-catalysed esterification of ricinoleic and kojic acids in solvent-free system. Three immobilized lipases were tested and the best KMR yields were attained with Lipozyme TL IM and Novozym 435. Since Lipozyme TL IM is the cheapest, it was selected to optimize the reaction conditions. The optimal reaction conditions were 80 °C for the temperature, 1:1 for the alcohol/acid molar ratio, 600 rpm for stirring speed and 7.8% for the catalyst concentration. Under these conditions, the reaction was scaled up in a 5×10⁻³ m³ stirred tank reactor. ¹H-¹³C HMBC-NMR showed that the primary hydroxyl group of kojic acid was regioselectively esterified. The KMR has more lipophilicity than kojic acid and showed antioxidant activity that improves the oxidation stability of biodiesel.

Matched MeSH terms: Esterification
Facile modulation of enantioselectivity of thermophilic Geobacillus zalihae lipase by regulating hydrophobicity of its Q114 oxyanion

Abdul Wahab R, Basri M, Raja Abdul Rahman RN, Salleh AB, Abdul Rahman MB, Leow TC

Enzyme Microb Technol, 2016 Nov;93-94:174-181.
PMID: 27702478 DOI: 10.1016/j.enzmictec.2016.08.020

Site-directed mutagenesis of the oxyanion-containing amino acid Q114 in the recombinant thermophilic T1 lipase previously isolated from Geobacillus zalihae was performed to elucidate its role in the enzyme's enantioselectivity and reactivity. Substitution of Q114 with a hydrophobic methionine to yield mutant Q114M increased enantioselectivity (3.2-fold) and marginally improved reactivity (1.4-fold) of the lipase in catalysing esterification of ibuprofen with oleyl alcohol. The improved catalytic efficiency of Q114L was concomitant with reduced flexibility in the active site while the decreased enantioselectivity of Q114L could be directly attributed to diminished electrostatic repulsion of the substrate carboxylate ion that rendered partial loss in steric hindrance and thus enantioselectivity. The highest E-values for both Q114L (E-value 14.6) and Q114M (E-value 48.5) mutant lipases were attained at 50°C, after 12-16h, with a molar ratio of oleyl alcohol to ibuprofen of 1.5:1 and at 2.0% (w/v) enzyme load without addition of molecular sieves. Pertinently, site-directed mutagenesis on the Q114 oxyanion of T1 resulted in improved enantioselectivity and such approach may be applicable to other lipases of the same family. We demonstrated that electrostatic repulsion phenomena could affect flexibility/rigidity of the enzyme-substrate complex, aspects vital for enzyme activity and enantioselectivity of T1.

Matched MeSH terms: Esterification
Fulltext Palmitic acid in the sn-2 position of dietary triacylglycerols does not affect insulin secretion or glucose homeostasis in healthy men and women

Filippou A, Teng KT, Berry SE, Sanders TA

Eur J Clin Nutr, 2014 Sep;68(9):1036-41.
PMID: 25052227 DOI: 10.1038/ejcn.2014.141

BACKGROUND/OBJECTIVES: Dietary triacylglycerols containing palmitic acid in the sn-2 position might impair insulin release and increase plasma glucose.
SUBJECTS/METHODS: We used a cross-over designed feeding trial in 53 healthy Asian men and women (20-50 years) to test this hypothesis by exchanging 20% energy of palm olein (PO; control) with randomly interesterified PO (IPO) or high oleic acid sunflower oil (HOS). After a 2-week run-in period on PO, participants were fed PO, IPO and HOS for 6 week consecutively in randomly allocated sequences. Fasting (midpoint and endpoint) and postprandial blood at the endpoint following a test meal (3.54 MJ, 14 g protein, 85 g carbohydrate and 50 g fat as PO) were collected for the measurement of C-peptide, insulin, glucose, plasma glucose-dependent insulinotropic polypeptide and glucagon-like peptide-1, lipids and apolipoproteins; pre-specified primary and secondary outcomes were postprandial changes in C-peptide and plasma glucose.
RESULTS: Low density lipoprotein cholesterol was 0.3 mmol/l (95% confidence interval (95% CI)) 0.1, 0.5; P<0.001) lower on HOS than on PO or IPO as predicted, indicating good compliance to the dietary intervention. There were no significant differences (P=0.58) between diets among the 10 male and 31 female completers in the incremental area under the curve (0-2 h) for C-peptide in nmol.120 min/l: GM (95% CI) were PO 220 (196, 245), IPO 212 (190, 235) and HOS 224 (204, 244). Plasma glucose was 8% lower at 2 h on IPO vs PO and HOS (both P<0.05).
CONCLUSION: Palmitic acid in the sn-2 position does not adversely impair insulin secretion and glucose homeostasis.

Matched MeSH terms: Esterification
Fulltext Enhancement of mechanical and thermal properties of oil palm empty fruit bunch fiber poly(butylene adipate-co-terephtalate) biocomposites by matrix esterification using succinic anhydride

Siyamak S, Ibrahim NA, Abdolmohammadi S, Yunus WM, Rahman MZ

Molecules, 2012 Feb 16;17(2):1969-91.
PMID: 22343368 DOI: 10.3390/molecules17021969

In this work, the oil palm empty fruit bunch (EFB) fiber was used as a source of lignocellulosic filler to fabricate a novel type of cost effective biodegradable composite, based on the aliphatic aromatic co-polyester poly(butylene adipate-co-terephtalate) PBAT (Ecoflex™), as a fully biodegradable thermoplastic polymer matrix. The aim of this research was to improve the new biocomposites' performance by chemical modification using succinic anhydride (SAH) as a coupling agent in the presence and absence of dicumyl peroxide (DCP) and benzoyl peroxide (BPO) as initiators. For the composite preparation, several blends were prepared with varying ratios of filler and matrix using the melt blending technique. The composites were prepared at various fiber contents of 10, 20, 30, 40 and 50 (wt %) and characterized. The effects of fiber loading and coupling agent loading on the thermal properties of biodegradable polymer composites were evaluated using thermal gravimetric analysis (TGA). Scanning Electron Microscopy (SEM) was used for morphological studies. The chemical structure of the new biocomposites was also analyzed using the Fourier Transform Infrared (FTIR) spectroscopy technique. The PBAT biocomposite reinforced with 40 (wt %) of EFB fiber showed the best mechanical properties compared to the other PBAT/EFB fiber biocomposites. Biocomposite treatment with 4 (wt %) succinic anhydride (SAH) and 1 (wt %) dicumyl peroxide (DCP) improved both tensile and flexural strength as well as tensile and flexural modulus. The FTIR analyses proved the mechanical test results by presenting the evidence of successful esterification using SAH/DCP in the biocomposites' spectra. The SEM micrograph of the tensile fractured surfaces showed the improvement of fiber-matrix adhesion after using SAH. The TGA results showed that chemical modification using SAH/DCP improved the thermal stability of the PBAT/EFB biocomposite.

Matched MeSH terms: Esterification
Fulltext Topical piroxicam in vitro release and in vivo anti-inflammatory and analgesic effects from palm oil esters-based nanocream

Abdulkarim MF, Abdullah GZ, Chitneni M, Salman IM, Ameer OZ, Yam MF, et al.

Int J Nanomedicine, 2010 Nov 04;5:915-24.
PMID: 21116332 DOI: 10.2147/IJN.S13305

INTRODUCTION: During recent years, there has been growing interest in use of topical vehicle systems to assist in drug permeation through the skin. Drugs of interest are usually those that are problematic when given orally, such as piroxicam, a highly effective anti-inflammatory, anti-pyretic, and analgesic, but with the adverse effect of causing gastrointestinal ulcers. The present study investigated the in vitro and in vivo pharmacodynamic activity of a newly synthesized palm oil esters (POEs)-based nanocream containing piroxicam for topical delivery.
METHODS: A ratio of 25:37:38 of POEs: external phase: surfactants (Tween 80:Span 20, in a ratio 80:20), respectively was selected as the basic composition for the production of a nanocream with ideal properties. Various nanocreams were prepared using phosphate-buffered saline as the external phase at three different pH values. The abilities of these formulae to deliver piroxicam were assessed in vitro using a Franz diffusion cell fitted with a cellulose acetate membrane and full thickness rat skin. These formulae were also evaluated in vivo by comparing their anti-inflammatory and analgesic activities with those of the currently marketed gel.
RESULTS: After eight hours, nearly 100% of drug was transferred through the artificial membrane from the prepared formula F3 (phosphate-buffered saline at pH 7.4 as the external phase) and the marketed gel. The steady-state flux through rat skin of all formulae tested was higher than that of the marketed gel. Pharmacodynamically, nanocream formula F3 exhibited the highest anti- inflammatory and analgesic effects as compared with the other formulae.
CONCLUSION: The nanocream containing the newly synthesized POEs was successful for trans-dermal delivery of piroxicam.

Matched MeSH terms: Esterification
Edible lipids modification processes: A review

Kadhum AA, Shamma MN

Crit Rev Food Sci Nutr, 2017 Jan 02;57(1):48-58.
PMID: 26048727

Lipid is the general name given to fats and oils, which are the basic components of cooking oils, shortening, ghee, margarine, and other edible fats. The chosen term depends on the physical state at ambient temperature; fats are solids and oils are liquids. The chemical properties of the lipids, including degree of saturation, fatty acid chain length, and acylglycerol molecule composition are the basic determinants of physical characteristics such as melting point, cloud point, solid fat content, and thermal behavior. This review will discuss the major lipid modification strategies, hydrogenation, and chemical and enzymatic interesterification, describing the catalysts used mechanisms, kinetics, and impacts on the health-related properties of the final products. Enzymatic interesterification will be emphasized as method that produces a final product with good taste, zero trans fatty acids, and a low number of calories, requires less contact with chemicals, and is cost efficient.

Matched MeSH terms: Esterification
Membrane-lytic actions of sulphonated methyl ester surfactants and implications to bactericidal effect and cytotoxicity

Pan F, Li Z, Gong H, Petkov JT, Lu JR

J Colloid Interface Sci, 2018 Dec 01;531:18-27.
PMID: 30015167 DOI: 10.1016/j.jcis.2018.07.031

Surfactants are multifunctional molecules widely used in personal care and healthcare formulations to cleanse, help disperse active ingredients (e.g., forming emulsions) and stabilise products. With increasing demands on improving biosafety, there is now mounting pressure to understand how different surfactants elicit toxicities at molecular and cellular levels. This work reports the membrane-lytic behaviour of a group of sulphonated methyl ester (SME) surfactants together with representative conventional surfactants. All surfactants displayed the clear rise of lysis of the model lipid bilayer membranes around their CMCs, but the two ionic surfactants SDS and C12TAB even caused measurable lysis below their CMCs, with membrane-lytic actions increasing with monomer concentration. Furthermore, whilst ionic and nonionic surfactants could achieve full membrane lysis once above their CMCs, this ability was weak from the SME surfactants and decreased with increasing the acyl chain length. In contrast to the conventional anionic surfactants such as SDS and SLES, the protein solubilizing capability of the SME surfactants was also low. On the other hand, MTT assays against 3T3 fibroblast cells and human chondrocyte cells revealed high toxicity from SDS and C12TAB against the other surfactants studied, but the difference between SME and the rest of conventional surfactants was small. Similar behaviour was also observed in their bactericidal effect against E. coli and S. aureus. The trend is broadly consistent with their membrane-lytic behaviour, indicating little selectivity in their cytotoxicity and bactericidal action. These results thus reveal different toxicities implicated from different surfactant head groups. Increase in acyl chain length as observed from SME surfactants could help improve surfactant biocompatibility.

Matched MeSH terms: Esterification
Fulltext The Role of Solvent-Accessible Leu-208 of Cold-Active Pseudomonas fluorescens Strain AMS8 Lipase in Interfacial Activation, Substrate Accessibility and Low-Molecular Weight Esterification in the Presence of Toluene

Yaacob N, Ahmad Kamarudin NH, Leow ATC, Salleh AB, Raja Abd Rahman RNZ, Mohamad Ali MS

Molecules, 2017 Aug 12;22(8).
PMID: 28805665 DOI: 10.3390/molecules22081312

The alkaline cold-active lipase from Pseudomonas fluorescens AMS8 undergoes major structural changes when reacted with hydrophobic organic solvents. In toluene, the AMS8 lipase catalytic region is exposed by the moving hydrophobic lid 2 (Glu-148 to Gly-167). Solvent-accessible surface area analysis revealed that Leu-208, which is located next to the nucleophilic Ser-207 has a focal function in influencing substrate accessibility and flexibility of the catalytic pocket. Based on molecular dynamic simulations, it was found that Leu-208 strongly facilitates the lid 2 opening via its side-chain. The KM and Kcat/KM of L208A mutant were substrate dependent as it preferred a smaller-chain ester (pNP-caprylate) as compared to medium (pNP-laurate) or long-chain (pNP-palmitate) esters. In esterification of ethyl hexanoate, L208A promotes a higher ester conversion rate at 20 °C but not at 30 °C, as a 27% decline was observed. Interestingly, the wild-type (WT) lipase's conversion rate was found to increase with a higher temperature. WT lipase AMS8 esterification was higher in toluene as compared to L208A. Hence, the results showed that Leu-208 of AMS8 lipase plays an important role in steering a broad range of substrates into its active site region by regulating the flexibility of this region. Leu-208 is therefore predicted to be crucial for its role in interfacial activation and catalysis in toluene.

Matched MeSH terms: Esterification
Fulltext Characterization of CRISPR Mutants Targeting Genes Modulating Pectin Degradation in Ripening Tomato

Wang D, Samsulrizal NH, Yan C, Allcock NS, Craigon J, Blanco-Ulate B, et al.

Plant Physiol, 2019 02;179(2):544-557.
PMID: 30459263 DOI: 10.1104/pp.18.01187

Tomato (Solanum lycopersicum) is a globally important crop with an economic value in the tens of billions of dollars, and a significant supplier of essential vitamins, minerals, and phytochemicals in the human diet. Shelf life is a key quality trait related to alterations in cuticle properties and remodeling of the fruit cell walls. Studies with transgenic tomato plants undertaken over the last 20 years have indicated that a range of pectin-degrading enzymes are involved in cell wall remodeling. These studies usually involved silencing of only a single gene and it has proved difficult to compare the effects of silencing these genes across the different experimental systems. Here we report the generation of CRISPR-based mutants in the ripening-related genes encoding the pectin-degrading enzymes pectate lyase (PL), polygalacturonase 2a (PG2a), and β-galactanase (TBG4). Comparison of the physiochemical properties of the fruits from a range of PL, PG2a, and TBG4 CRISPR lines demonstrated that only mutations in PL resulted in firmer fruits, although mutations in PG2a and TBG4 influenced fruit color and weight. Pectin localization, distribution, and solubility in the pericarp cells of the CRISPR mutant fruits were investigated using the monoclonal antibody probes LM19 to deesterified homogalacturonan, INRA-RU1 to rhamnogalacturonan I, LM5 to β-1,4-galactan, and LM6 to arabinan epitopes, respectively. The data indicate that PL, PG2a, and TBG4 act on separate cell wall domains and the importance of cellulose microfibril-associated pectin is reflected in its increased occurrence in the different mutant lines.

Matched MeSH terms: Esterification

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