Optimization of the Synthesis of Structured Phosphatidylcholine with Medium Chain Fatty Acid

Ochoa‐Flores, Angélica A.; Hernández-Becerra, Josafat A.; Cavazos-Garduño, A.; Vernon‐Carter, E.J.; Garcı́a, Hugo S.

doi:10.5650/jos.ess17087

Cited by 17 publications

(12 citation statements)

References 36 publications

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“…No significant differences in INCLPC was observed between the isomers in case of aw = 0.11 and 0.23. The obtained results are consistent with the literature data, which 14 22.3 ± 0.9 18 14.4 ± 3.7 23 0.33 6.4 ± 0.1 4 24.4 ± 0.8 9 11.8 ± 0.3 6 42.0 ± 0.8 7 36.1 ± 0.5 12 15.5 ± 0.8 16 48.0 ± 0.8 22 18.3 ± 0.8 15 8.7 ± 0.3 19 73.6 ± 3.0 24 1 Results refers to 48 h of the acidolysis reaction. condition are given in Figure 5.…”

Section: Effect Of Water Activitysupporting

confidence: 92%

“…Naturally occurring glycerophospholipids usually composed of saturated fatty acids, such as stearic or palmitic acid in the sn-1 position, while the sn-2 position is occupied by unsaturated acids (i.e., oleic, linoleic, and arachidonic) [14]. Structured phospholipids are the products of such modifications, and the process itself involves rearrangement, addition or replacement of fatty acid residues in the sn-1 or sn-2 position of glycerol backbone with desired fatty acids, for example medium chain saturated acids, to ensure high oxidative stability [15][16][17], polyunsaturated fatty acids (eicosapentaenoic and docosahexaenoic) that possess health-promoting properties [18][19][20] or conjugated fatty acids, such as conjugated linoleic acid (CLA) (Table 1). Amongst the PL modification processes, enzymatic methods are currently becoming the most popular because of many advantages (i.e., regioselectivity, substrate specificity, low temperature, and lack of harsh and harmful chemical reagents).…”

Section: Introductionmentioning

confidence: 99%

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

Niezgoda

Gliszczyńska

2019

Catalysts

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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.

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Section: Effect Of Water Activitysupporting

confidence: 92%

Section: Introductionmentioning

confidence: 99%

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

Niezgoda

Gliszczyńska

2019

Catalysts

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“…Many lipases share amino-acid sequences identical to PLA1 and show phospholipase activity [5]. As shown in Table 3, PLA1 displayed greater catalytic performance in the incorporation of EPA/DHA [54,60,63], medium-chain fatty acids (MCFAs) [56,61], conjugated linolenic acid (CLA) [62,67] and some other fatty acids into PLs via the acidolysis or transesterification reaction (Figure 7). Immobilized PLA1-catalyzed transesterification of PC and DHA/EPA-rich ethyl esters is similar to the lipase-catalyzed transesterification [57].…”

Section: Phospholipase A-mediated the Preparation Of Structured Phosp...mentioning

confidence: 99%

“…To economize the process, PLAs are usually immobilized before being used in catalysis. Resinous materials, such as Duolite A658 [56,62], resin D380 [60], Amberlite XAD 7HP [37,58] and some other supports are the most commonly used and appropriate choices to immobilize PLA. Both the properties of supports (such as pore size, stability, hydrophobicity, electronegativity, etc.)…”

Section: Phospholipase A-mediated the Preparation Of Structured Phosp...mentioning

confidence: 99%

Progress & Prospect of Enzyme-Mediated Structured Phospholipids Preparation

Dai

Liu

2022

Catalysts

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In recent years, structured phospholipids (SPLs), which are modified phospholipids (PLs), have attracted more attention due to their great potential for application in the field of pharmacy, food, cosmetics, and health. SPLs not only possess enhanced chemical, physical and nutritional properties, but also present superior bioavailability in comparison with other lipid forms, such as triacylglycerols, which make SPLs become more competitive carriers to increase the absorption of the specific fatty acids in the body. Compared with chemical-mediated SPLs, the process of enzyme-mediated SPLs has the advantages of high product variety, high substrate selectivity, and mild operation conditions. Both lipases and phospholipases can be used in the enzymatic production of SPLs, and the main reaction type contains esterification, acidolysis, and transesterification. During the preparation, reaction medium, acyl migration, water content/activity, substrates and enzymes, and some other parameters have significant effects on the production and purity of the desired PLs products. In this paper, the progress in enzymatic modification of PLs over the last 20 years is reviewed. Reaction types and characteristic parameters are summarized in detail and the parameters affecting acyl migration are first discussed to give the inspiration to optimize the enzyme-mediated SPLs preparation. To expand the application of enzyme-mediated SPLs in the future, the prospect of further study on SPLs is also proposed at the end of the paper.

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“…Among these, structured phospholipids (SPLs) have achieved considerable attention and have been widely applied in food, pharmaceutical, cosmetic and other chemical industries 4,5 . In particular, medium‐chain structured phospholipids (MCPs), also known as low‐calorie SPLs, are usually produced via substitution of medium‐chain fatty acids (MCFAs) containing six to ten carbon atoms for long‐chain fatty acids (FAs) in native phospholipids (PLs) 6‐8 . The MCFA‐enriched SPLs are regarded as a kind of potential functional PLs for food and medical applications due to their improved nutritional and pharmaceutical functions, emulsification activities, heat stabilities, etc.…”

Section: Introductionmentioning

confidence: 99%

Acidolysis of phospholipids with medium‐chain fatty acids over M‐SBA‐15 (M = Zn, Al) silicas as efficient solid catalysts

et al. 2022

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BACKGROUND Efficient and sustainable production of structured phospholipids (SPLs) enriched in medium‐chain fatty acids (MCFAs) in a heterogeneous manner is crucial for their potential applications in functional foods and drugs. Herein, for the first time, Zn‐ and Al‐incorporated SBA‐15 silicas were prepared by the coprecipitation method and further researched for catalytic synthesis of MCFA‐enriched SPLs through acidolysis reaction of natural phospholipids with capric or caprylic acid. RESULTS The as‐prepared Zn‐ and Al‐incorporated SBA‐15 samples exhibited superior catalytic activities under mild experimental conditions (50 °C, 6 h) to commercial homogeneous Lewis acids and benchmark enzymes. Correspondingly, the capric acid and caprylic acid incorporations were respectively achieved up to ~40.25 ± 0.40% (or 35.08 ± 0.09%) and 37.26 ± 0.38% (or 33.02 ± 0.13%) for Zn‐ (or Al‐) incorporated SBA‐15 catalyst. Moreover, various methods such as scanning electron microscopy with energy‐dispersive X‐ray spectrometry, ultraviolet–visible diffuse reflectance spectroscopy and pyridine–Fourier transform infrared spectroscopy were utilized to characterize the two catalysts in order to elucidate the possible structure–performance relationship. Accordingly, the above‐mentioned satisfactory results are most probably due to the well‐ordered mesostructures and large amounts of active Lewis acid sites existing in the investigated materials. Noticeably, the two catalysts featured good separation and excellent recyclability as well. CONCLUSION The Zn‐ and Al‐incorporated SBA‐15 catalysts studied in this work might shed light on novel, sustainable and economic alternatives for effective SPL production to diminish the applications of conventional homogeneous catalysts and biocatalysts in food industries. © 2022 Society of Chemical Industry.

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Optimization of the Synthesis of Structured Phosphatidylcholine with Medium Chain Fatty Acid

Cited by 17 publications

References 36 publications

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

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

Progress & Prospect of Enzyme-Mediated Structured Phospholipids Preparation

Acidolysis of phospholipids with medium‐chain fatty acids over M‐SBA‐15 (M = Zn, Al) silicas as efficient solid catalysts

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