Lipase-catalyzed interesterification of egg-yolk phosphatidylcholine and plant oils

Abstract

SUMMARY:The incorporation of polyunsaturated fatty acids into the sn-1 position of egg-yolk phosphatidylcholine (PC) in the process of lipase-catalyzed interesterification was investigated. For this purpose plant oils containing these acids in the triacylglycerol (TAG) form were used as acyl donors and three commercially available immobilized lipases were examined as biocatalysts. In all the experiments the best results were obtained using Novozym 435. After 72 h of the reaction of PC with linseed oil the maximum incorporation of α-linolenic acid into PC was 34%. The result of this reaction was also a reduction in the n-6/n-3 ratio in egg-yolk PC from 24.5 to 0.7. The highest incorporation n-6 PUFAs into PC were obtained with evening primrose oil as the acyl donor, and in this case, 50.7% of n-6 PUFA as the sum of linoleic and γ-linolenic was achieved. The highest content of γ-linolenic acid in modified PC (7.3%) was achieved in the reaction of PC with borage oil. KEYWORDS:Egg-yolk phosphatidylcholine; Interesterification; Lipase; Plant oil; Polyunsaturated fatty acids; Structured phospholipids RESUMEN: Interesterificación de fosfatidilcolina de yema de huevo y aceites vegetales catalizada por lipasas. Se ha investigado la incorporación de ácidos grasos poliinsaturados en la posición sn-1 de fosfatidilcolina de yema de huevo (PC) en el proceso de interesterificación catalizado por lipasas. Para lograr este propósito, fueron examinados aceites vegetales que contienen estos ácidos en la forma de triacilgliceroles (TAG) como donadores de acilo y tres lipasas inmovilizadas disponibles comercialmente. En todos los experimentos los mejores resultados se obtuvieron para Novozym 435. La incorporación máxima de ácido α-linolénico en PC fue del 34% después de 72h de la reacción de PC con aceite de linaza. El resultado de esta reacción fue también la reducción de la relación de n-6/n-3 en PC de yema de huevo de 24.5 a 0.7. La incorporación más alta de n-6 PUFAs en PC se logró para el aceite de onagra como donador de acilo, en este caso se alcanzó el 50.7% de n-6 PUFA, como suma de los ácidos linoleico y γ-linolénico. El mayor contenido de ácido γ-linolénico en PC modificado (7.3%) se logró en la reacción de PC con aceite de borraja.

Production of Structured Phosphatidylcholine with High Content of Myristic Acid by Lipase-Catalyzed Acidolysis and Interesterification

“…In this investigation, Novozym 435 showed less activity, giving 27.5 wt% and 13.5 wt% incorporation of MA into PC in interesterification and acidolysis, respectively. In our previous studies, this lipase was the most efficient in incorporation of α-linolenic acid, punicic acid, and PUFA into PC in the interesterification and acidolysis processes [18,21,27,30]. On the other hand, similar to the results presented here, TLL was less active in interesterification of PC with pomegranate seed oil.…”

“…Four commercially available lipases; Lipozyme ® (RML), Lipozyme TL IM (TLL), Candida antarctica lipase B (Novozym 435) and Candida antarctica lipase A (CALA) were evaluated for their ability to catalyze interesterification and acidolysis between egg-yolk PC and TMA or MA, respectively. Lipozyme ® and Lipozyme TL IM are classified as 1,3-regiospecific lipases [15] the third one is considered as a non-specific enzyme, but in most lipid modifications it shows high selectivity towards the sn-1 position [27,30,31]. The fourth of the lipases (CALA) is reported to show a sn-2-regioselectivity [32,33], although such preference in the structure of triacylglycerols (TAG) is not sufficient to selective synthesis of 1,3-diglycerides or 2-monoglycerides [34].…”

“…In our previous study, we reported on a pioneer method for the production of structured phosphatidylcholine (SPC) using plant oils as the source of natural acyl donors in the form of triacylglycerols. Using this methodology, phospholipids were enriched with unsaturated fatty acids from the n-3 or n-6 family in the process of interesterification with corresponding oil, that is, linseed, safflower, sunflower, borage, and primrose evening oil [27]. The same reaction system with pomegranate seed oil as the acyl donor was applied in the incorporation of conjugated linolenic acid (punicic acid) into egg-yolk phosphatidylcholine (PC) [21].…”

Lipase-Catalyzed Transesterification of Egg-Yolk Phophatidylcholine with Concentrate of n-3 Polyunsaturated Fatty Acids from Cod Liver Oil

“…The modern trend is using natural oils as a sources of triacylglycerols rich in desirable fatty acid in direct-interesterification with phospholipids [ 29 , 30 ]. In our research group, we elaborated the lipase-catalyzed incorporation of different biologically active acids ( n -3 PUFA, n -6 PUFA, or conjugated fatty acids) into PC using natural plant oils as the acyl donors i.e., sunflower oil, linseed oil, pomegranate seed oil [ 31 , 32 ]. The concentrates of CLA obtained from sunflower and safflower oil were also used to produce CLA-enriched PLs [ 33 ].…”