Lysophosphatidylcholine Synthesis by Lipase-catalyzed Ethanolysis

Yang, Guolong; Yang, Ruoxi; Hu, Jingbo

doi:10.5650/jos.ess14246

Cited by 9 publications

(8 citation statements)

References 15 publications

(7 reference statements)

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“…More recently, Lipozyme TL-IM ® and Novozym 435 ® were shown to catalyze ethanolysis of purified phosphatidylcholine as efficiently as Lipozyme RM-IM ® (Yang et al, 2015). Reaction was carried out either directly in ethanol as in studies mentioned above or in hexane where phosphatidylcholine and ethanol were dissolved.…”

Section: Lipase-catalyzed Alcoholysis Of Phospholipidsmentioning

confidence: 99%

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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Section: Lipase-catalyzed Alcoholysis Of Phospholipidsmentioning

confidence: 99%

Lipase-catalyzed production of lysophospholipids

Mnasri

Hérault

Gauvry

et al. 2017

OCL

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“…1 after CALB reaction. It was estimated that 1/3 of phospholipids were converted to lysophospholipids or phosphatidyl glycerol based on a previous report 11 , although they were not detectable under the HPLC conditions used in this study. Interestingly, phospholipids were hardly detected in the 2-MAG fraction Fig.…”

Section: Hplc Analysis Of Phospholipid Contentsmentioning

confidence: 69%

“…Lipase, however, reacts with FFA and phospholipids as well as with acyl glycerols 10,11 . Thus, CALB could produce FAEE, lysophospholipids or phosphatidyl glycerol from FFA and phospholipids during step 1 of the above procedure, if they are present in the oil applied to the method.…”

Section: Introductionmentioning

confidence: 99%

Effects of Minor Components of Crude Vegetable Oil on the Enzymatic Method to Analyze Positional Fatty Acid Distributions in Triacylglycerols with<i>Candida antarctica</i> Lipase B

et al. 2016

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“…When 12.5 wt% of Novozym® 435 was used, the standard amount applied in current Novozym® 435-mediated processes, < 20 mol% of 1-LPC yield was obtained. Yang et al reported 97.7 % yield of 1-LPC via Novozym® 435 mediated ethanolysis of PC using only 10 wt% of biocatalyst loading [ 18 ]. However, we have not been able reproduce this result.…”

Section: Resultsmentioning

confidence: 99%

Highly efficient preparation of 1-lysophosphatidylcholine via high proportion of Novozym® 435 (lipase B from Candida antarctica)-catalyzed ethanolysis

Yasuda

Yamamoto

2020

Biotechnology Reports

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Highlights 1-Lysophosphatidylcholine was prepared via Novozym® 435 (lipase B from Candida antarctica )-catalyzed ethanolysis. Novozym® 435 showed sn -1 regiospecificity to phosphatidylcholine. The water content of ethanol and high enzyme dose were key determinants of yields. The yield of 1-LPC at optimal reaction conditions was 96.5 ± 0.2 mol%. No acyl migration occurred during the reaction.

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Lysophosphatidylcholine Synthesis by Lipase-catalyzed Ethanolysis

Cited by 9 publications

References 15 publications

Lipase-catalyzed production of lysophospholipids

Lipase-catalyzed production of lysophospholipids

Effects of Minor Components of Crude Vegetable Oil on the Enzymatic Method to Analyze Positional Fatty Acid Distributions in Triacylglycerols with<i>Candida antarctica</i> Lipase B

Highly efficient preparation of 1-lysophosphatidylcholine via high proportion of Novozym® 435 (lipase B from Candida antarctica)-catalyzed ethanolysis

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