Novel and efficient solid to solid transphosphatidylation of two phenylalkanols in a biphasic GRAS medium

Casado, Víctor; Reglero, Guillermo; Torres, Carlos F.

doi:10.1016/j.molcatb.2013.10.011

Cited by 9 publications

(13 citation statements)

References 16 publications

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“…Although it has been described that Ca 2+ is a requirement apparently no significant for PLDs from bacteria , previous studies in our group have showed better results in the presence of Ca 2+ ions. Besides, in precipitation‐driven catalysis systems, such as the present study, the addition of specific counter‐ions that form poorly soluble salts with an ionic form of the product of the reaction (and not with the substrates) leads to product salts precipitation from the reaction mixture .…”

Section: Resultscontrasting

confidence: 58%

“…Different ratios of batyl alcohol and phosphatidylcholine (PC) were studied. For this purpose, some other reaction conditions were chosen based on previous publications , namely 1% (w/w of the substrates) enzyme loading, 67 mmol/L of CaCl 2 , a volumetric ratio organic to aqueous phase of 2 to 1, 40°C and 20 h of reaction time. The results are shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…In most of the reported transphosphatidylation reactions, diffusional limitation has been attributed to the heterogeneity of the reaction system . The use of “in situ product removal” technology basically consists of a reaction mixture in which both reactants and products are above their solubility limit in the reaction mixture which improves both downstreaming operations and volumetric productivity . Organic solvents commonly used in these reactions can be hazardous to human health and environment, hence, the use of substances commonly utilized as flavoring agents and with GRAS category is considered as a healthier and safer alternative, as well as a promising strategy to increase the industrial feasibility for these bioprocesses .…”

Section: Introductionmentioning

confidence: 99%

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Novel glyceryl ethers phospholipids produced by solid to solid transphosphatidylation in the presence of a food grade phospholipase D

Arranz-Martínez

Casado

Reglero

et al. 2017

Euro J Lipid Sci & Tech

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Enzymatic transphosphatidylation between batyl alcohol and phospatidylcholine has been investigated. In situ product removal methodology and the utilization of a green biphasic medium consisting of a buffer and an organic phase comprised of generally recognized as safe flavoring additives, have been established as milestones to increase the applicability of the process. Different organic phases (limonene, pinene, ethyl isovalerate, ethyl lactate, ethyl butyrate, hexanal, and cyclopentanone) and one aqueous phase (0.1 M acetate buffer at pH = 5.5) were studied. The relative proportion of organic and aqueous phases was also investigated. Different molar ratios alkylglycerol/phosphatidylcholine (10:1, 5:1, 2:1, 1:1, and 1:2) were also evaluated. Addition of calcium chloride and the reaction temperature have been adjusted in the enzymatic transphosphatidylation. Finally, the percentage of phospholipase D and the molar concentration of the reactants were also optimized. The ratio transphosphatidylation to hydrolysis was evaluated for the different biphasic reaction mixtures tested. The best results (ca. 70% w/w of glyceryl ether phospholipid) were achieved utilizing 5% (w/w) of phospholipase D, equimolar ratio of reactants and limonene/acetate buffer at a volumetric ratio 1:3. The volumetric productivity of the process was then optimized up to 126 mM and scaled‐up to 50 g of reaction mixture with similar results in terms of composition and yield. This study reports a procedure for the production of tailor‐made phospholipids from commercial sources with high volumetric yield. These highly valuable ingredients are intended to be used as both delivery systems and bioactive lipids. Practical applications: Solid to solid transphosphatidylation based on in situ product removal has been developed for the synthesis of a novel glyceryl ether phospholipid, incorporating batyl alcohol into the polar head of the phosphatidylcholine in the presence of a food grade PLD. Enzymatic transphosphatidylation usually reported in the literature utilize very low concentration of phospholipid and a large excess of the other reactant. In this sense, the present study evaluated different molar ratios alkylglycerol/phosphatidylcholine. Besides, regarding novel phospholipid as food for human use, the utilization of toxic organic solvents was avoided in its production, replacing them by GRAS organic solvents. Hence, this procedure readily scalable is intended to be used for obtaining this novel glyceryl ether phospholipid with capabilities to perform as both novel delivery systems and bioactive lipids. In addition, a very simple downstream process for product recovery has been also described. Schematic representation of a solid to solid transphosphatidylation reaction between phosphatidylcholine and batyl alcohol in a biphasic reaction medium comprised of an acetate buffer and an organic solvent generally recognized as safe (limonene).

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Section: Resultscontrasting

confidence: 58%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Novel glyceryl ethers phospholipids produced by solid to solid transphosphatidylation in the presence of a food grade phospholipase D

Arranz-Martínez

Casado

Reglero

et al. 2017

Euro J Lipid Sci & Tech

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“…As a result, a product yield of as high as 90 % was obtained after 12 h, and no by-product formation was observed. The solid-to-solid reactions for transphosphatidylation of PC with tyrosol and hydroxytyrosol were also performed in a biphasic GRAS medium composed of sodium acetate buffer and ethyl butyrate (Casado et al 2014). Ionic liquids, a new class of solvents for enzymatic reactions, have not been investigated for PL modification.…”

Section: Novel Applications To Enzymatic Synthesis Of Plsmentioning

confidence: 99%

Enzymatic synthesis and modification of structured phospholipids: recent advances in enzyme preparation and biocatalytic processes

Hama¹,

Ogino

Kondo

2015

Appl Microbiol Biotechnol

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Phospholipids (PLs) containing specific polar head groups and fatty acids, artificially synthesized from a complex mixture of natural PLs, have considerable industrial applications. The biocatalytic approaches to synthesizing structured PLs are of great interest because the enzymes used show high selectivity and performance under mild conditions, leading to the generation of products that cannot easily be obtained by chemical catalysis. Although the limited supply of phospholipases (e.g., phospholipase D) has thus far been an obstacle to the widespread use of enzymatic processing, recent advances in enzyme preparation have opened up various applications for PL modification. In this review, attempts to increase the productivity and utility of microbial phospholipases and lipases are presented. We also summarize recent developments in enzyme-catalyzed modification of PLs, focusing particularly on the relevant reactions, bioreactor design, and novel proof-of-concept experiments.

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“…Concerning novel derivatives of phenolic compounds, Casado et al have recently synthesized phospholipid derivatives of tyrosol and HT with phosphatidylcholine, where the phenolics were included in the polar head of the phospholipid replacing choline by enzymatic transphosphatidylation (Fig. ).…”

Section: Introductionmentioning

confidence: 99%

Antioxidant activity of phosphatidyl derivatives of hydroxytyrosol in edible oils

Martín

García-Serrano

Casado

et al. 2014

Euro J Lipid Sci & Tech

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A comparative study of the antioxidant activity of hydroxytyrosol (HT) and phosphatidyl derivatives of hydroxytyrosol (PHT) added at increasing concentrations to diverse edible oils (lard oil, refined olive oil, and diacylglycerol‐rich oil) was performed. Antioxidant activity index was estimated as the ratio of induction time in presence of the compounds to induction time in their absence, after oxidation under Rancimat conditions. Tocopherol (TOC) and phosphatydilcholine (PC) were used as reference, and combinations PHT:TOC, PHT:PC, HT:TOC, and PC:TOC were also tested. PHT and HT showed a protective effect as the added concentration of antioxidants increased. However, the protective effect of PHT was superior to HT for olive oil and diacylglycerol oil, and similar to HT for lard oil. The magnitude of the protection of both PHT and HT was higher in lard oil, followed by olive oil and the poorest protection was for diacylglycerol oil. Both HT and PHT were superior to TOC. Furthermore, PC showed a lack of antioxidant activity compared to PHT. A lack of synergism between the combinations of antioxidants was found. Practical applications: Including phosphatidyl derivatives of hydroxytyrosol in edible oils provides two advantages. First, they serve as a source of hydroxytyrosol and second they stabilize the lipid matrix, and in this respect the phosphatidyl derivatives perform better than hydroxytyrosol or tocopherols. A comparative study of the antioxidant activity of hydroxytyrosol (HT) and phosphatidyl derivatives of HT (PHT) added at increasing concentrations to diverse edible oils (lard oil, refined olive oil, and diacylglycerol‐rich oil) was performed. Tocopherol as reference was also tested. PHT might be included in edible oils with the double strategy to offer a source of HT and, at the same, stabilize the own lipid matrix, even in a superior mode than HT or the standard tocopherol. Nevertheless, the particularity of each individual oil would determine the magnitude of the protection.

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Novel and efficient solid to solid transphosphatidylation of two phenylalkanols in a biphasic GRAS medium

Cited by 9 publications

References 16 publications

Novel glyceryl ethers phospholipids produced by solid to solid transphosphatidylation in the presence of a food grade phospholipase D

Novel glyceryl ethers phospholipids produced by solid to solid transphosphatidylation in the presence of a food grade phospholipase D

Enzymatic synthesis and modification of structured phospholipids: recent advances in enzyme preparation and biocatalytic processes

Antioxidant activity of phosphatidyl derivatives of hydroxytyrosol in edible oils

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