Solvent-free lipase catalysed synthesis of diacylgycerols as low-calorie food ingredients

Problems derived from obesity and overweight have recently promoted the development of fat substitutes and other low-calorie foods. On the one hand, fats with short and medium chain fatty acids are a source of quick energy, easily hydrolyzable and hardly stored as fat. Furthermore, 1,3-diacylglycero...

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Published in:Frontiers in Bioengineering and Biotechnology
Main Author: Luis eVazquez
Format: Article in Journal/Newspaper
Language:English
Published: Frontiers Media S.A. 2016
Subjects:
Online Access:https://doi.org/10.3389/fbioe.2016.00006
https://doaj.org/article/2d5a501861e44807b725bc4e95e17e4f
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author Luis eVazquez
author_facet Luis eVazquez
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collection Directory of Open Access Journals: DOAJ Articles
container_title Frontiers in Bioengineering and Biotechnology
container_volume 4
description Problems derived from obesity and overweight have recently promoted the development of fat substitutes and other low-calorie foods. On the one hand, fats with short and medium chain fatty acids are a source of quick energy, easily hydrolyzable and hardly stored as fat. Furthermore, 1,3-diacylglycerols are not hydrolyzed to 2-monoacylglycerols in the gastrointestinal tract, reducing the formation of chylomicron and lowers the serum level of triacylglycerols by decreasing its re-synthesis in the enterocyte and its metabolism and absorption by the enterocyte are limited in comparison with the TAG, reducing chylomicron formation. In this work these two effects were combined to synthesize short and medium chain 1,3 diacylglycerols, leading to a product with great potential as for their low-calorie properties. Lipase catalysed transesterification reactions were performed between short and medium chain fatty acid ethyl esters and glycerol. Different variables were investigated such as the type of biocatalyst, the molar ratio FAEE:glycerol, the adsorption of glycerol on silica gel or the addition of lecithin. Best reaction conditions were evaluated considering the conversion intopercentage of 1,3-DAG produced and the reaction rate. Except Novozym 435 (Candida antarctica), other lipases required the adsorption of glycerol on silica gel to form acylglycerols. Lipases that gave the best results with adsorption were Novozym 435 and Lipozyme RM IM (Rhizomucor miehei) with 52% and 60.7% of DAG at 32 h, respectively. Because of its specificity for sn-1 and sn-3 positions, lipases leading to a higher proportion of 1,3-DAG vs 1,2-DAG were Lipozyme RM IM (39.8% and 20.9%, respectively) and Lipase PLG (Alcaligenes sp.) (35.9% and 19.3%, respectively). By adding 1% (w/w) of lecithin to the reaction with Novozym 435 and raw glycerol the reaction rate was considerably increased from 41.7% to 52.8% DAG at 24 h.
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spelling ftdoajarticles:oai:doaj.org/article:2d5a501861e44807b725bc4e95e17e4f 2025-01-16T19:17:23+00:00 Solvent-free lipase catalysed synthesis of diacylgycerols as low-calorie food ingredients Luis eVazquez 2016-02-01T00:00:00Z https://doi.org/10.3389/fbioe.2016.00006 https://doaj.org/article/2d5a501861e44807b725bc4e95e17e4f EN eng Frontiers Media S.A. http://journal.frontiersin.org/Journal/10.3389/fbioe.2016.00006/full https://doaj.org/toc/2296-4185 2296-4185 doi:10.3389/fbioe.2016.00006 https://doaj.org/article/2d5a501861e44807b725bc4e95e17e4f Frontiers in Bioengineering and Biotechnology, Vol 4 (2016) Lipase diacylglycerol solvent-free reactions transesterification fatty acid ethyl ester Medium chain fatty acid Biotechnology TP248.13-248.65 article 2016 ftdoajarticles https://doi.org/10.3389/fbioe.2016.00006 2022-12-31T12:05:06Z Problems derived from obesity and overweight have recently promoted the development of fat substitutes and other low-calorie foods. On the one hand, fats with short and medium chain fatty acids are a source of quick energy, easily hydrolyzable and hardly stored as fat. Furthermore, 1,3-diacylglycerols are not hydrolyzed to 2-monoacylglycerols in the gastrointestinal tract, reducing the formation of chylomicron and lowers the serum level of triacylglycerols by decreasing its re-synthesis in the enterocyte and its metabolism and absorption by the enterocyte are limited in comparison with the TAG, reducing chylomicron formation. In this work these two effects were combined to synthesize short and medium chain 1,3 diacylglycerols, leading to a product with great potential as for their low-calorie properties. Lipase catalysed transesterification reactions were performed between short and medium chain fatty acid ethyl esters and glycerol. Different variables were investigated such as the type of biocatalyst, the molar ratio FAEE:glycerol, the adsorption of glycerol on silica gel or the addition of lecithin. Best reaction conditions were evaluated considering the conversion intopercentage of 1,3-DAG produced and the reaction rate. Except Novozym 435 (Candida antarctica), other lipases required the adsorption of glycerol on silica gel to form acylglycerols. Lipases that gave the best results with adsorption were Novozym 435 and Lipozyme RM IM (Rhizomucor miehei) with 52% and 60.7% of DAG at 32 h, respectively. Because of its specificity for sn-1 and sn-3 positions, lipases leading to a higher proportion of 1,3-DAG vs 1,2-DAG were Lipozyme RM IM (39.8% and 20.9%, respectively) and Lipase PLG (Alcaligenes sp.) (35.9% and 19.3%, respectively). By adding 1% (w/w) of lecithin to the reaction with Novozym 435 and raw glycerol the reaction rate was considerably increased from 41.7% to 52.8% DAG at 24 h. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles Frontiers in Bioengineering and Biotechnology 4
spellingShingle Lipase
diacylglycerol
solvent-free reactions
transesterification
fatty acid ethyl ester
Medium chain fatty acid
Biotechnology
TP248.13-248.65
Luis eVazquez
Solvent-free lipase catalysed synthesis of diacylgycerols as low-calorie food ingredients
title Solvent-free lipase catalysed synthesis of diacylgycerols as low-calorie food ingredients
title_full Solvent-free lipase catalysed synthesis of diacylgycerols as low-calorie food ingredients
title_fullStr Solvent-free lipase catalysed synthesis of diacylgycerols as low-calorie food ingredients
title_full_unstemmed Solvent-free lipase catalysed synthesis of diacylgycerols as low-calorie food ingredients
title_short Solvent-free lipase catalysed synthesis of diacylgycerols as low-calorie food ingredients
title_sort solvent-free lipase catalysed synthesis of diacylgycerols as low-calorie food ingredients
topic Lipase
diacylglycerol
solvent-free reactions
transesterification
fatty acid ethyl ester
Medium chain fatty acid
Biotechnology
TP248.13-248.65
topic_facet Lipase
diacylglycerol
solvent-free reactions
transesterification
fatty acid ethyl ester
Medium chain fatty acid
Biotechnology
TP248.13-248.65
url https://doi.org/10.3389/fbioe.2016.00006
https://doaj.org/article/2d5a501861e44807b725bc4e95e17e4f