scholarly journals Enzymatic Production of Biologically Active 3-Methoxycinnamoylated Lysophosphatidylcholine via Regioselctive Lipase-Catalyzed Acidolysis

Foods ◽  
2021 ◽  
Vol 11 (1) ◽  
pp. 7
Author(s):  
Marta Okulus ◽  
Magdalena Rychlicka ◽  
Anna Gliszczyńska
Keyword(s):  
Reaction Time ◽  
Design Method ◽  
Reaction Medium ◽  
Egg Yolk ◽  
Major Product ◽  
Biologically Active ◽  
Molar Ratio ◽  
Enzymatic Production ◽  
Egg Yolk Phosphatidylcholine ◽  
Level 3

Enzymatic acidolysis of egg-yolk phosphatidylcholine (PC) with 3-methoxycinnamic acid (3-OMe-CA) was investigated to produce biologically active 3-methoxycinnamoylated phospholipids. Four commercially available lipases were screened for their ability to incorporate 3-OMe-CA into PC. The results showed that Novozym 435 is the most effective biocatalyst for this process, while during the examination of organic solvents, heptane was found propriate reaction medium. The other reaction parameters including the substrate molar ratio, enzyme load and reaction time were designed using an experimental factorial design method. According to three-level-3-factor Box-Behnken model it was shown that all of studied parameters are crucial variables for the maximization of the synthesis of structured PLs. The optimum conditions derived via response surface methodology (RSM) were: 30% of lipase of the total weight of substrates, 1:15 molar ration of PC/3-OMe-CA and reaction time 4 days. The process of acidolysis performed on the increased scale at optimized parameters afforded two products. The major product, 3-methoxycinnamoylated lysophosphatidylcholine (3-OMe-CA-LPC) was isolated in high 48% yield, while 3-methoxycinnamoylated phosphatidylcholine (3-OMe-CA-PC) was produced in trace amount only in 1.2% yield. Obtained results indicate that presented biotechnological method of synthesis of 3-methoxycinnamoylated lysophosphatidylcholine is competitive to the previously reported chemical one.

scholarly journals Interesterification of Egg-Yolk Phosphatidylcholine with p-Methoxycinnamic Acid Catalyzed by Immobilized Lipase B from Candida Antarctica

Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1181
Author(s):  
Magdalena Rychlicka ◽  
Anna Gliszczyńska
Keyword(s):  
Reaction Time ◽  
Design Method ◽  
Immobilized Lipase ◽  
Reaction Medium ◽  
Solvent System ◽  
Novozym 435 ◽  
Molar Ratio ◽  
Binary Solvent ◽  
Methoxycinnamic Acid ◽  
Substrate Molar Ratio

The p-methoxycinnamic acid (p-MCA) is one of the most popular phenylpropanoids, the beneficial impact of which on the human health is well documented in the literature. This compound has shown many valuable activities including anticancer, antidiabetic, and neuro- and hepatoprotective. However, its practical application is limited by its low bioavailability resulting from rapid metabolism in the human body. The latest strategy, aimed at overcoming these limitations, is based on the production of more stability in systemic circulation bioconjugates with phospholipids. Therefore, the aim of this research was to develop the biotechnological method for the synthesis of phospholipid derivatives of p-methoxycinnamic acid, which can play a role of new nutraceuticals. We developed and optimized enzymatic interesterification of phosphatidylcholine (PC) with ethyl p-methoxycinnamate (Ep-MCA). Novozym 435 and a binary solvent system of toluene/chloroform 9:1 (v/v) were found to be the effective biocatalyst and reaction medium for the synthesis of structured p-MCA phospholipids, respectively. The effects of the other reaction parameters, such as substrate molar ratio, enzyme dosage, and reaction time, on the degree of incorporation of p-MCA into PC were evaluated by use of an experimental factorial design method. The results showed that substrate molar ratio and biocatalyst load have significant effects on the synthesis of p-methoxycinnamoylated phospholipids. The optimum conditions were: Reaction time of three days, 30% (w/w) of Novozym 435, and 1/10 substrate molar ratio PC/Ep-MCA. Under these parameters, p-methoxycinnamoylated lysophosphatidylcholine (p-MCA-LPC) and p-methoxycinnamoylated phosphatidylcholine (p-MCA-PC) were obtained in isolated yields of 32% and 3% (w/w), respectively.

scholarly journals Enzymatic Synthesis of O-Methylated Phenophospholipids by Lipase-Catalyzed Acidolysis of Egg-Yolk Phosphatidylcholine with Anisic and Veratric Acids

Catalysts ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 538 ◽  
Author(s):  
Marta Okulus ◽  
Anna Gliszczyńska
Keyword(s):  
Egg Yolk ◽  
Solvent System ◽  
Biologically Active ◽  
Molar Ratio ◽  
Binary Solvent ◽  
Molar Ratios ◽  
Egg Yolk Phosphatidylcholine ◽  
Screening Experiments ◽  
Acidolysis Reaction ◽  
System 1

Lipase-catalyzed acidolysis reactions of egg-yolk phosphatidylcholine (PC) with anisic (ANISA) and veratric (VERA) acids were investigated to develop a biotechnological method for the production of corresponding biologically active O-methylated phenophospholipids. Screening experiments with four commercially available immobilized lipases indicated that the most effective biocatalyst for the incorporation of ANISA into phospholipids was Novozym 435. None of the tested enzymes were able to catalyze the synthesis of PC structured with VERA. The effects of different solvents, substrate molar ratios, temperature, enzyme loading, and time of the reaction on the process of incorporation of ANISA into the phospholipids were evaluated in the next step of the study. The mixture of toluene/chloroform in the ratio 9:1 (v/v) significantly increased the incorporation of ANISA into PC. The acidolysis reaction was carried out using the selected binary solvent system, 1/15 substrate molar ratio PC/ANISA, 30% (w/w) enzyme load, and temperature of 50 °C afforded after 72 h anisoylated lysophosphatidylcholine (ANISA-LPC) and anisoylated phosphatidylcholine (ANISA-PC) in isolated yields of 28.5% and 2.5% (w/w), respectively. This is the first study reporting the production of ANISA-LPC and ANISA-PC via a one-step enzymatic method, which is an environmentally friendly alternative to the chemical synthesis of these biologically active compounds.

scholarly journals Development and Optimization of Lipase-Catalyzed Synthesis of Phospholipids Containing 3,4-Dimethoxycinnamic Acid by Response Surface Methodology

Catalysts ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 588
Author(s):  
Magdalena Rychlicka ◽  
Natalia Niezgoda ◽  
Anna Gliszczyńska
Keyword(s):  
Response Surface Methodology ◽  
Food Additives ◽  
Reaction Medium ◽  
Egg Yolk ◽  
Molar Ratio ◽  
Molar Ratios ◽  
Egg Yolk Phosphatidylcholine ◽  
Potential Applications ◽  
Substrate Molar Ratio ◽  
Enzyme Load

The interesterification reaction of egg-yolk phosphatidylcholine (PC) with ethyl ester of 3,4-dimethoxycinnamic acid (E3,4DMCA) catalyzed by Novozym 435 in hexane as a reaction medium was shown to be an effective method for the synthesis of corresponding structured O-methylated phenophospholipids. The effects of substrate molar ratios, time of the reaction and enzyme load on the process of incorporation of 3,4DMCA into PC were evaluated by using the experimental factorial design of three factors and three levels. The results showed that a substrate molar ratio is a crucial variable for the maximization of the synthesis of 3,4-dimethoxycinnamoylated phospholipids. Under optimized parameters of 1/10 substrate molar ratio PC/E3,4DMCA, enzyme load 30% (w/w), hexane as a medium and incubation time of 3 days, the incorporation of aromatic acid into phospholipid fraction reached 21 mol%. The modified phosphatidylcholine (3,4DMCA-PC) and modified lysophosphatidylcholine (3,4DMCA-LPC) were obtained in isolated yields of 3.5% and 27.5% (w/w), respectively. The developed method of phosphatidylcholine interesterification is the first described in the literature dealing with 3,4DMCA and allows us to obtain new O-methylated phenophospholipids with potential applications as food additives or nutraceuticals with pro-health activity.

scholarly journals The utilization of the mesoporous Ti-SBA-15 catalyst in the epoxidation of allyl alcohol to glycidol and diglycidyl ether in the water medium

2015 ◽  
Vol 17 (4) ◽  
pp. 23-31 ◽  
Author(s):  
Agnieszka Wróblewska ◽  
Edyta Makuch ◽  
Małgorzata Dzięcioł ◽  
Roman Jędrzejewski ◽  
Paweł Kochmański ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Reaction Time ◽  
Allyl Alcohol ◽  
Water Solution ◽  
Reaction Medium ◽  
Diglycidyl Ether ◽  
Molar Ratio ◽  
Water Medium ◽  
Catalyst Content ◽  
Allyl Alcohol Epoxidation

Abstract This work presents the studies on the optimization the process of allyl alcohol epoxidation over the Ti-SBA-15 catalyst. The optimization was carried out in an aqueous medium, wherein water was introduced into the reaction medium with an oxidizing agent (30 wt% aqueous solution of hydrogen peroxide) and it was formed in the reaction medium during the processes. The main investigated technological parameters were: the temperature, the molar ratio of allyl alcohol/hydrogen peroxide, the catalyst content and the reaction time. The main functions the process were: the selectivity of transformation to glycidol in relation to allyl alcohol consumed, the selectivity of transformation to diglycidyl ether in relation to allyl alcohol consumed, the conversion of allyl alcohol and the selectivity of transformation to organic compounds in relation to hydrogen peroxide consumed. The analysis of the layer drawings showed that in water solution it is best to conduct allyl alcohol epoxidation in direction of glycidol (selectivity of glycidol 54 mol%) at: the temperature of 10–17°C, the molar ratio of reactants 0.5–1.9, the catalyst content 2.9–4.0 wt%, the reaction time 2.7–3.0 h and in direction of diglycidyl ether (selectivity of diglycidyl ether 16 mol%) at: the temperature of 18–33°C, the molar ratio of reactants 0.9–1.65, the catalyst content 2.0–3.4 wt%, the reaction time 1.7–2.6 h. The presented method allows to obtain two very valuable intermediates for the organic industry.

Optimization of a Ti-MWW Catalysed Phenol Hydroxylation Process

2012 ◽  
Vol 15 (2) ◽  
Author(s):  
Agnieszka Wróblewska
Keyword(s):  
Hydrogen Peroxide ◽  
Reaction Time ◽  
Organic Compounds ◽  
Design Method ◽  
Uniform Design ◽  
Molar Ratio ◽  
Phenol Hydroxylation ◽  
Statistical Experimental Design ◽  
Experimental Design Method ◽  
Good Substitute

AbstractsAs a result of phenol hydroxylation, two useful products can be received: hydroquinone and pyrocatechol. In this work the hydroxylation of phenol with hydrogen peroxide over the Ti-MWW catalyst has been studied. Optimization studies were performed by application of a statistical experimental design method utilizing a rotatable-uniform design. The influence of five parameters on the course of this process was examined: temperature (120-150°C), molar ratio of phenol/hydrogen peroxide (0.5-1.5), acetonitrile - solvent content (20- 50 wt%), catalyst - Ti-MWW content (8-18 wt%) and reaction time (60-120 min). The process description was based on four response functions: the conversion of phenol to organic compounds, the yield of pyrocatechol, the yield of hydroquinone and the conversion of phenol to tars. The most favourable parameters for the process of phenol hydroxylation were as follows: temperature 147-150°C, molar ratio of phenol/hydrogen peroxide 0.5-0.6, acetonitrile content 21-24 wt%, Ti-MWW content 10.3-10.6, reaction time 221-236 min. In summary, these the most favourable parameters allow one to obtain pyrocatechol with the yield of 18 mol%, hydroquinone with the yield of 20 mol%, at the conversion of phenol to organic compounds 38 mol% in relatively mild and safe conditions. These results also showed that Ti-MWWcatalyst can be a good substitute for TS-1 catalyst.

scholarly journals Effective synthesis of n-butyl salicylate over wash coated cordierite honeycomb by zirconia and its mixed oxides: a kinetic study

2018 ◽  
Vol 53 (1) ◽  
pp. 63-76
Author(s):  
M Shyamsundar ◽  
SZM Shamshuddin
Keyword(s):  
Reaction Time ◽  
Reaction Temperature ◽  
Methyl Salicylate ◽  
Mixed Oxides ◽  
Surface Acidity ◽  
Maximum Yield ◽  
Major Product ◽  
Transesterification Reaction ◽  
Molar Ratio ◽  
Butyl Ether

Cordierite honeycombs were coated with solid acid catalysts such as ZrO2 (Z), Mo(VI)/ZrO2 (MZ) and Pt-SO4 2-/ZrO2 (PSZ) were prepared and characterized for their physico-chemical properties. These catalytic materials were characterized for their total surface acidity, crystallinity, functionality, elemental analysis and morphology by using techniques such as NH3 -TPD, PXRD, FTIR, ICP-OES, SEM and TEM respectively. These honeycomb catalysts were used for the liquid phase transesterification reaction of methyl salicylate (MS) with n-butanol (n-BA). Optimization of reaction conditions such as reaction temperature, reaction time, amount of catalysts and molar ratio of the reactants were carried out to obtain maximum yield of transester (n-butyl salicylate). n-butyl salicylate is obtained as major product and di-butyl ether is obtained as minor product. Highest total transester 70 % obtained by MZ and 80 % n-butyl salicylate and 10 % selectivity of di-butyl ether obtained in the presence of 0.4 g of honeycomb coated catalysts at a molar ratio of MS: n-BA 2:1, reaction temperature 403 K and reaction time 4 h. The energy of activation (16.81 and 14.92 kJ mol-1) and temperature coefficient (1.36 and 1.12) values of the MZ and PSZ were obtained from the kinetic studies. Pre-adsorption studies showed that the transesterification reaction methyl salicylate with n-butyl alcohol over honeycomb catalysts follows Langmuir-Hinshelwood mechanism. A reaction mechanism for transesterification is proposed based on the kinetic data. Reactivation and reusability studies of the honeycomb coated as well as powder form of catalysts up to 6 reaction cycles were also studied.Bangladesh J. Sci. Ind. Res.53(1), 63-76, 2018

Optimization of Biodiesel Production from Transesterification of Waste Cooking Oils Using Alkaline Catalysts

2014 ◽  
Vol 695 ◽  
pp. 289-292
Author(s):  
M.M. Zamberi ◽  
Farid Nasir Ani ◽  
S.N.H. Hassan
Keyword(s):  
Reaction Time ◽  
Catalyst Concentration ◽  
Acid Methyl Ester ◽  
Biodiesel Production ◽  
Molar Ratio ◽  
Waste Vegetable Oil ◽  
Waste Cooking Oils ◽  
Level 3 ◽  
Cooking Oils ◽  
Full Factorial

The transesterification of waste vegetable oil (WVO) with methanol in the presence of potassium hydroxide (KOH) is studied in order to produce biodiesel. All the results were evaluated using central composite design by applying a double 5 level 3 factor full factorial designs. Twenty experiments were replicated under the typical range of parameter conditions coded as x1 for oil molar ratio, x2 as catalyst concentration and x3 for reaction time. The experimental fatty acid methyl ester (FAME) are compared with the predicted FAME using RSM. The optimal predicted FAME production was obtained at 92.60%. It is specified under conditions of molar ratio 4:1 mol/mol, 0.5033 wt% catalyst concentration and reaction time of 60 minutes.

Application of Methylated N-(4-N,N-Dimethylaminocinnamyl) Chitosan for Oral Protein Drug Delivery

2012 ◽  
Vol 506 ◽  
pp. 465-468
Author(s):  
J. Kowapradit ◽  
Theerasak Rojanarata ◽  
Tanasait Ngawhirunpat ◽  
A. Apirakaramwong ◽  
Warayuth Sajomsang ◽  
...  
Keyword(s):  
Drug Delivery ◽  
Entrapment Efficiency ◽  
Egg Yolk ◽  
Molar Ratio ◽  
Protein Drug ◽  
Egg Yolk Phosphatidylcholine ◽  
Model Protein ◽  
Protein Drug Delivery ◽  
Low Cytotoxicity

In the present study, methylated N-(4-N,N-dimethylaminocinnamyl) chitosan (TM65CM50CS) was synthesized and investigated for oral protein drug delivery by combining with liposomes entrapped bovine serum albumin (FITC-BSA), a model protein. FITC-BSA liposomes composed of egg yolk phosphatidylcholine and sodium oleate in molar ratio of 10:2 were prepared by thin film hydration method. The TM65CM50CS coated liposomal FITC-BSA was evaluated for transport of protein and its cytotoxicity in Caco-2 cells. Moreover, the in vitro stability of BSA in TM65CM50CS coated liposomes was also examined by the degradation of protein from pancreatin. The mean particle size and zeta-potential of liposomes were 101+0.02 nm and -27.44+2.02 mV, respectively. Initial FITC-BSA (2.5% w/w) to lipid showed the highest percentage entrapment efficiency (50.13%) and FITC-BSA content (8.08 mg/g of lipid). The results of FITC-BSA transport showed that TM65CM50CS coated FITC-BSA liposomes enhanced protein permeability across Caco-2 cell monolayers with low cytotoxicity. In addition, these liposomes could protect the degradation of protein from pancreatin. Our studies demonstrated that TM65CM50CS coated liposomes have the potential to be used as an oral protein drug delivery.

scholarly journals Lipase Catalyzed Acidolysis for Efficient Synthesis of Phospholipids Enriched with Isomerically Pure cis-9,trans-11 and trans-10,cis-12 Conjugated Linoleic Acid

Catalysts ◽  
2019 ◽  
Vol 9 (12) ◽  
pp. 1012 ◽  
Author(s):  
Natalia Niezgoda ◽  
Anna Gliszczyńska
Keyword(s):  
Linoleic Acid ◽  
Conjugated Linoleic Acid ◽  
Biological Effects ◽  
Reaction System ◽  
Rhizomucor Miehei ◽  
Egg Yolk ◽  
Biologically Active ◽  
Molar Ratio ◽  
Active Compounds ◽  
Cla Isomers

The production of phospholipid (PL) conjugates with biologically active compounds is nowadays an extensively employed approach. This type of phospholipids conjugates could improve bioavailability of many poorly absorbed active compounds such as isomers of conjugated linoleic acid (CLA), which exhibit versatile biological effects. The studies were carried out to elaborate an efficient enzymatic method for the synthesis of phospholipids with pure (>90%) cis-9,trans-11 and trans-10,cis-12 CLA isomers. For this purpose, three commercially available immobilized lipases were examined in respect to specificity towards CLA isomers in acidolysis of egg-yolk phosphatidylcholine (PC). Different incorporation rates were observed for the individual CLA isomers. Under optimal conditions: PC/CLA molar ratio 1:6; Rhizomucor miehei lipase loading 24% wt. based on substrates; heptane; DMF, 5% (v/v); water activity (aw), 0.11; 45 °C; magnetic stirring, 300 rpm; 48 h., effective incorporation (EINC) of CLA isomers into PC reached ca. 50%. The EINC of CLA isomers was elevated for 25–30% only by adding a water mimic (DMF) and reducing aw to 0.11 comparing to the reaction system performed at aw = 0.23. The developed method of phosphatidylcholine acidolysis is the first described in the literature dealing with isometrically pure CLA and allow to obtain very high effective incorporation.

scholarly journals In-Situ Rheological Studies of Cationic Lignin Polymerization in an Acidic Aqueous System

Polymers ◽  
2020 ◽  
Vol 12 (12) ◽  
pp. 2982
Author(s):  
Samira Gharehkhani ◽  
Weijue Gao ◽  
Pedram Fatehi
Keyword(s):  
Molecular Weight ◽  
Reaction Time ◽  
Reaction System ◽  
Reaction Medium ◽  
Molar Ratio ◽  
Process Conditions ◽  
Trimethylammonium Chloride ◽  
Tan Δ ◽  
Lignin Polymerization

The chemistry of lignin polymerization was studied in the past. Insights into the rheological behavior of the lignin polymerization system would provide crucial information required for tailoring lignin polymers with desired properties. The in-situ rheological attributes of lignin polymerization with a cationic monomer, [2-(methacryloyloxy)ethyl] trimethylammonium chloride (METAC), were studied in detail in this work. The influences of process conditions, e.g., temperature, component concentrations, and shear rates, on the viscosity variations of the reaction systems during the polymerization were studied in detail. Temperature, METAC/lignin molar ratio, and shear rate increases led to the enhanced viscosity of the reaction medium and lignin polymer with a higher degree of polymerization. The extended reaction time enhanced the viscosity attributing to the larger molecular weight of the lignin polymer. Additionally, the size of particles in the reaction system dropped as reaction time was extended. The lignin polymer with a larger molecular weight and Rg behaved mainly as a viscose (tan δ > 1 or G″ > G′) material, while the lignin polymer generated with smaller molecular weight and shorter Rg demonstrated strong elastic characteristics with a tan (δ) lower than unity over the frequency range of 0.1−10 rad/s.

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