Acyl migration during deacylation of phospholipids rich in docosahexaenoic acid (DHA): an enzymatic approach for evidence and study

Poisson, Laurent; Devos, Marie; Godet, Stéphanie; Ergan, F.; Pencreach, Gaëlle

doi:10.1007/s10529-009-9932-5

Cited by 23 publications

(12 citation statements)

References 21 publications

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“…4, which also indicated that the extent of acyl migration from sn ‐2 to sn ‐1 on LPC was facilitated by the higher temperature. These results were consistent with previous reports 23, 24.…”

Section: Resultssupporting

confidence: 94%

Enzymatic preparation of L‐α‐glycerylphosphorylcholine in an aqueous medium

Zhang

Liu

Wang

2012

Euro J Lipid Sci & Tech

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L-a-Glycerylphosphorylcholine (L-a-GPC) was successfully prepared from phosphatidylcholine (PC) of food-grade soy lecithin powder using a novel enzymatic reaction in an aqueous medium. 94.5% yield of La-GPC was obtained under the optimal conditions of 558C, 6.67 mg/mL substrate, 2 mM CaCl 2 , and 33.4 U/mL phospholipase A 1 (Lecitase Ultra). L-a-GPC at 98% purity, 73.4% (wt%) recovery, and specific rotation (½a 20 D ) of À2.58 was achieved by silica gel column chromatography. Owing to its excellent catalytic efficiency, low cost, and ready availability, phospholipase A 1 (Lecitase Ultra) provides a very satisfactory option for converting PC to L-a-GPC.Practical applications: L-a-Glycerylphosphorylcholine (L-a-GPC) has been studied recently for its potential use as a supplement that may support neurological functions, but it is only found in trace amounts in nature. The present results indicate that Lecitase Ultra can be used for producing L-a-GPC from aqueous PC and suggest encouraging prospects for practical or industrial applications utilizing its notable catalytic performance, economy, and convenience.

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Section: Resultssupporting

confidence: 94%

Enzymatic preparation of L‐α‐glycerylphosphorylcholine in an aqueous medium

Zhang

Liu

Wang

2012

Euro J Lipid Sci & Tech

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“…Such rearrangement leads to six different lyso PCs consisting of three enantiomeric pairs of positional isomers. This phenomenon was observed by many authors (Adlercreutz & Wehtje, 2001;Poisson, Devos, Godet, Ergan, & Pencreac'h, 2009;Vikbjerg, Mu, & Xu, 2007). In methodology concerning positional analysis of PC, only acyl migration constitutes a serious drawback, which could lead to incorrect final results.…”

Section: Resultsmentioning

confidence: 93%

A simple method for positional analysis of phosphatidylcholine

et al. 2012

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“…Indeed, 2-LPLs are thermodynamically more stable than 1-LPLs and intramolecular acyl migration from the sn2 to the sn1 position was shown to readily occur (Plückthun and Dennis, 1982). In our case, a multi-step enzymatic method was developed to address this issue (Poisson et al, 2009). The LPLs produced by the selective hydrolysis of I. galbana phospholipids with Lipase F AP-15 ® were further hydrolyzed using a phospholipase A2.…”

Section: Lipase-catalyzed Deacylation Of Phospholipidsmentioning

confidence: 94%

Lipase-catalyzed production of lysophospholipids

Mnasri

Hérault

Gauvry

et al. 2017

OCL

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-Lysophospholipids, such as lysophosphatidic acid or lysophosphatidylcholine, are important bioactive lipids, involved in various normal and pathological cellular processes. They also have industrial and pharmaceutical uses such as emulsifiers or components of drug delivery systems. Lipases, which natural substrates are long chain triacylglycerols, are important biocatalysts for organic synthesis mainly due to their broad substrate specificity and their ability to display high catalytic activity in organic media. This paper describes the various lipase-catalyzed reactions implemented for the production of lysophospholipids. They include hydrolysis or alcoholysis of phospholipids and acylation of the glycerophosphoryl moiety. Special emphasis is made on our work dealing with the production of lysophospholipids rich in dososahexaenoic acid, an important dietary polyunsaturated fatty acid via the hydrolysis of phospholipids extracted from the microalga Isochrysis galbana.Keywords: lipase / lysophospholipid / hydrolysis / esterification / docosahexaenoic acid Résumé -Synthèse de lysophospholipides catalysée par des lipases. Les lysophospholipides, comme par exemple l'acide lysophosphatidique ou la lysophosphatidylcholine, sont des médiateurs lipidiques impliqués dans de nombreux processus cellulaires. Ils sont également employés au niveau industriel comme émulsifiants ou dans les formulations galéniques, par exemple. Les lipases, dont les substrats naturels sont les triacylglycérols à longues chaînes, sont des biocatalyseurs très utilisés en synthèse organique, du fait de leur large spécificité de substrats et de leur activité catalytique élevée en milieu organique. Cet article décrit les différentes approches développées pour la synthèse des lysophospholipides mettant en oeuvre les lipases, à savoir l'hydrolyse ou l'alcoolyse de phospholipides et l'acylation de la partie glycerophosphoryle correspondant au lysophospholipide recherché. En particulier, nos travaux, portant sur la synthèse de lysophospholipides riches en acide docosahexaénoique par hydrolyse de phospholipides issus de la microalgue Isochrysis galbana, sont présentés.

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Acyl migration during deacylation of phospholipids rich in docosahexaenoic acid (DHA): an enzymatic approach for evidence and study

Cited by 23 publications

References 21 publications

Enzymatic preparation of L‐α‐glycerylphosphorylcholine in an aqueous medium

Enzymatic preparation of L‐α‐glycerylphosphorylcholine in an aqueous medium

A simple method for positional analysis of phosphatidylcholine

Lipase-catalyzed production of lysophospholipids

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