Enzymatic hydrolysis of phospholipids from Isochrysis galbana for docosahexaenoic acid enrichment

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

doi:10.1016/j.enzmictec.2005.08.040

Cited by 42 publications

(32 citation statements)

References 37 publications

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“…The time course of the reaction with Lipase F AP-15 ® is shown in Figure 2 (from Devos et al, 2006). It can be seen that DHA ratio among total phospholipid fatty acids increased rapidly, from 50% to around 70% within the first 15 min of reaction, and afterwards more slowly to reach 77% after 3 h of reaction.…”

Section: Lipase-catalyzed Deacylation Of Phospholipidsmentioning

confidence: 99%

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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 Deacylation Of Phospholipidsmentioning

confidence: 99%

“…Indeed, in this microalga, 75% of the DHA contained in total lipids are contained in the phospholipidic fraction and DHA represents 50% of the total fatty acid profile of phospholipids. Moreover, DHA is actually located at the sn2 position of the glycerol backbone (Devos et al, 2006).…”

Section: Lipase-catalyzed Deacylation Of Phospholipidsmentioning

confidence: 99%

Lipase-catalyzed production of lysophospholipids

Mnasri

Hérault

Gauvry

et al. 2017

OCL

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“…Total lipids and fatty acid analyses were carried out respectively by thin layer chromatography (TLC) and gas chromatography (GC) as previously described (Devos et al, 2006). TLC of total lipids carried out by a double development in one dimension (Fig.…”

Section: Lipidsmentioning

confidence: 99%

“…Moreover, it has been reported in literature that medium-chain fatty acids (MCFAs) may improve bioavailability of PUFAs (Lemarié et al, 2016). The production of DHA lysophospholipids as well-tructured phospholipids can be achieved by enzymatic catalysis using more particularly lipases (Devos et al, 2006;Vikbjerg, 2006).…”

Section: Lipidsmentioning

confidence: 99%

“…The phospholipids from I. galbana were submitted to hydrolysis catalyzed by a phospholipase A2 (PLA2). The time course of this reaction clearly showed that DHA was preferentially released so it can be concluded that DHA is mainly located at the sn-2 position (Devos et al, 2006). Starting with this raw material, a selective deacylation can be implemented to produce lysophospholipids rich in DHA (Fig.…”

Section: Lipidsmentioning

confidence: 99%

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Lipids and lipolytic enzymes of the microalga Isochrysis galbana

Hubert

Poisson

Loiseau

et al. 2017

OCL

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-Marine microalgae are now well-known for their ability to produce omega-3 long chain polyunsaturated fatty acids (PUFAs) such as docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA). Among these microalgae, Isochrysis galbana has received increasing interest especially because of its high DHA content and its common use in hatchery to feed fish larvae and clams. Moreover, lipolysis occurring from the biomass harvest stage suggests that I. galbana may contain lipolytic enzymes with potential interesting selectivities. For these reasons, the potential of this microalga for the production of valuable lipids and lipolytic enzymes was investigated. Lipid analysis revealed that DHA is mainly located at the sn-2 position of the phospholipids. Thus, I. galbana was considered as an interesting starting material for the lipase catalyzed production of 1-lyso-2-DHA-phospholipids which are considered as convenient vehicles for the conveyance of DHA to the brain. Lipids from I. galbana can also be used for the enzymecatalyzed production of structured phospholipids containing one DHA and one medium chain fatty acid in order to combine interesting therapeutic and biological benefits. Starting from total RNA extract from I. galbana, coding sequences of putative lipolytic enzymes were obtained by RACE and Nested PCR. The heterologous expression of a sequence designated IgTeCe was implemented. An expression plasmid was constructed by ligating the coding sequence to a plasmid vector and then cloned and expressed in E. coli. Results showed the effective functionality of plasmid construction for the production of a recombinant protein with the expected molecular mass. Moreover, local alignment using BLASTP and biochemical evidences support the hypothesis that the expressed protein is a thioesterase.Keywords: microalgae / v-3 polyunsaturated fatty acids / phospholipids / lipolytic enzymes Résumé -Lipides et enzymes lipolytiques de la microalgue Isochrysis galbana. Les microalgues marines sont maintenant bien connues pour leur aptitude à produire des acides gras à longue chaîne de la série v-3 comme l'acide docosahexahénoïque (DHA) ou eicosapentaénoïque (EPA). Parmi ces microalgues, Isochrysis galbana connaît, ces dernières années, un intérêt croissant du fait d'un contenu lipidique riche en DHA et de son importante utilisation en écloserie pour nourrir les larves de poissons et les bivalves. D'autre part, la lipolyse souvent observée dès l'étape de collecte de la biomasse ainsi que la forte teneur en DHA suggère qu'I. galbana pourrait contenir des enzymes lipolytiques intéressantes en termes de sélectivité. Pour ces différentes raisons, le potentiel de cette microalgue pour la production de lipides d'intérêt et d'enzymes lipolytiques a été étudié. L'analyse des lipides d'I. galbana a tout d'abord révélé que le DHA était majoritairement greffé sur la position sn-2 des phospholipides. Dans ce contexte, les phospholipides d'I. galbana constituent une matière première intéressante pour la production, par voie enzymatique, d...

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Tridocosahexaenoyl glycerol purification from docosahexaenoic acid single cell oil (DHASCO)

Venegas‐Venegas

Guil‐Guerrero

Rincón‐Cervera

et al. 2014

Euro J Lipid Sci & Tech

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Tridocosahexaenoyl glycerol (tri-DHA) has been identified and purified from the commercial oil DHASCO 1 , a natural and renewable source of DHA with 7.48 wt% of tri-DHA, by means of a gravimetric normal-phase chromatographic column and silver nitrate-silica gel as stationary phase. This method allows the purification of a highly enriched tri-DHA fraction from DHASCO 1 (84.4% of the total tri-DHA contained in DHASCO 1 ), and DHA accounting for 79.8% of the total fatty acids of the purified fraction. Subsequently, the whole process was scaled up to 10 times with satisfactory results.Practical applications: This work was conducted to obtain a valuable form of DHA from a natural resource. The whole process, in which the use of unsafe solvents is avoided, has been designed to allow the potential use of the DHA-enriched fraction in the food and pharmaceutical industries as nutritional supplement, as well as for use in laboratory research using animal models.

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Enzymatic hydrolysis of phospholipids from Isochrysis galbana for docosahexaenoic acid enrichment

Cited by 42 publications

References 37 publications

Lipase-catalyzed production of lysophospholipids

Lipase-catalyzed production of lysophospholipids

Lipids and lipolytic enzymes of the microalga Isochrysis galbana

Tridocosahexaenoyl glycerol purification from docosahexaenoic acid single cell oil (DHASCO)

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