Co-immobilization of bi-lipases on magnetic nanoparticles as an efficient catalyst for synthesis of functional oil rich in diacylglycerols, phytosterol esters and α-linolenic acid

Yao, Gui-Hong; Wang, Xiujuan; Yang, Minli; Chen, Fengming; Ling, Yun; Liu, Tong; Xing, Shu; Yao, Meiyi; Zhang, Feng

doi:10.1016/j.lwt.2020.109522

Cited by 15 publications

(7 citation statements)

References 31 publications

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“…For phytosterol esters' synthesis, the use of higher log P solvents has been reported as a better choice. Lipases, the main enzymes used in phytosterol esters' synthesis, usually exhibit greater catalytic activity and operational stability in higher log P solvents [67,74,87,92,157]. Zheng et al [95] evaluated solvents with different log P values (n-hexane, isooctane, cyclohexane, and tert-amyl alcohol) for the synthesis of phytosterol linolenate and observed that isooctane, the solvent with the highest log P (log P = 4.5), was the best solvent for the esterification.…”

Section: Effect Of Reaction Mediummentioning

confidence: 99%

Lipases as Effective Green Biocatalysts for Phytosterol Esters’ Production: A Review

et al. 2022

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Lipases are versatile enzymes widely used in the pharmaceutical, cosmetic, and food industries. They are green biocatalysts with a high potential for industrial use compared to traditional chemical methods. In recent years, lipases have been used to synthesize a wide variety of molecules of industrial interest, and extraordinary results have been reported. In this sense, this review describes the important role of lipases in the synthesis of phytosterol esters, which have attracted the scientific community’s attention due to their beneficial effects on health. A systematic search for articles and patents published in the last 20 years with the terms “phytosterol AND esters AND lipase” was carried out using the Scopus, Web of Science, Scielo, and Google Scholar databases, and the results showed that Candida rugosa lipases are the most relevant biocatalysts for the production of phytosterol esters, being used in more than 50% of the studies. The optimal temperature and time for the enzymatic synthesis of phytosterol esters mainly ranged from 30 to 101 °C and from 1 to 72 h. The esterification yield was greater than 90% for most analyzed studies. Therefore, this manuscript presents the new technological approaches and the gaps that need to be filled by future studies so that the enzymatic synthesis of phytosterol esters is widely developed.

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Section: Effect Of Reaction Mediummentioning

confidence: 99%

Lipases as Effective Green Biocatalysts for Phytosterol Esters’ Production: A Review

et al. 2022

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“…Subsequently, some enzymatic systems, such as the presence of organic solvents or a solvent‐free environment, 14,17‐19 the enzymatic method 20‐22 and the reactive mode of a packed‐bed reactor, 23 have been investigated in DAG synthesis to improve esterification activity. The combination lipases possess the advantage of a synergistic effect compared to the individual enzymes, and have been investigated in biodiesel (fatty acid alkyl esters) production of transesterification/esterification 24‐26 and hydrolysis, 27 as well as the synthesis of functional oil 28 . Nevertheless, the DAG yield and 1,3‐selectivity for the combi‐lipase biocatalyst have never been investigated for the enzymatic production of functional food.…”

Section: Introductionmentioning

confidence: 99%

“…The combination lipases possess the advantage of a synergistic effect compared to the individual enzymes, and have been investigated in biodiesel (fatty acid alkyl esters) production of transesterification/esterification [24][25][26] and hydrolysis, 27 as well as the synthesis of functional oil. 28 Nevertheless, the DAG yield and 1,3-selectivity for the combi-lipase biocatalyst have never been investigated for the enzymatic production of functional food.…”

Section: Introductionmentioning

confidence: 99%

Structure‐guided preparation of fuctional oil rich in 1,3‐diacylglycerols and linoleic acid from Camellia oil by combi‐lipase

Huang

Lin²,

Zhang³

et al. 2022

J Sci Food Agric

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Background: Diacylglycerol (DAG)-enriched oil has been attracting attention because of its nutritional benefits and biological functions, although the composition of its various free fatty acids (FFAs) and an unclear relationship between substrate and yield make it difficult to be identified and qualified with respect to its production. In the present study, linoleic acid-enriched diacylglycerol (LA-DAG) was synthesized and enriched from Camellia oil by the esterification process using the combi-lipase Lipozyme TL IM/RM IM system.Results: The relationship between FFA composition and DAG species productivity was revealed. The results showed that heterogeneous FFA with a major constituent (more than 50%) exhibited higher DAG productivity and inhibited triacylglycerol productivity compared to homogeneous constituents. Joint characterization by high-performance liquid chromatography-evaporative light scattering detection, gas chromatography-mass spectrometry and ultra-performance liquid chromatography-heated electrospray ionizationtandem mass spectrometry identified that DAG components contained dilinoleic acid acyl glyceride, linoleyl-oleyl glyceride and dioleic acid acyl glyceride in esterification products. Under the optimum conditions, 60.4% 1,3-DAG and 61.3% LA-DAG in the crude product at 1 h reaction were obtained, and further purified to 81.7% LA-DAG and 94.7% DAG via silica column chromatography. Conclusion:The present study provides a guideline for the identification of DAG species, as well as a structure-guided preparation method of DAG-enriched oils via the cost-effective combi-lipase.

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“…Enzymatic esterification can produce relatively higher DAG content than the enzymatic glycerolysis and partial hydrolysis. Focusing on the functional and nutritional properties of structured DAGs, docosapentaenoic acid (Wang et al, 2018), α-linolenic acid (Bavaro et al, 2020;Liu et al, 2018;Liu et al, 2021;Yao et al, 2020), gallic acid (Zhang et al, 2021), and pinolenic acid (Kim et al, 2018) have been inserted into DAG molecules. For example, Wang et al (2018) synthesized docosapentaenoic acid enriched DAG (48.4%) oil by enzymatic glycerolysis of algae oil and glycerol.…”

Section: Introductionmentioning

confidence: 99%

“…Awadallak et al (2020) proposed a new strategy to produce linseed DAG-rich oil (62.05 wt% DAG) by means of the combined use of glycerolysis and esterification. Yao et al (2020) developed a strategy for a one-pot enzymatic preparation of a functional oil with multifunctional components comprising commercial soybean oil, peanut oil, and rapeseed oil. Three kinds of functional oils were produced with high DAGs, phytosterol esters, and α-linolenic acid content (≥30.09%, ≥15.61% and ≥26.45%, respectively) under optimized conditions.…”

Section: Introductionmentioning

confidence: 99%

Fabrication, characterization, and purification of nutraceutical diacylglycerol components from Camellia oil

Huang

Liu

Huang

et al. 2022

Journal of Food Science

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Converting triacylgycerols (TAGs) from edible oils and fats into structured diacylglycerols (DAGs) is meaningful for reducing obesity. Camellia oil, rich in linoleic acid, has the potential to form structured linoleic acid-1,3-diacylglycerol (LA-1,3-DAG) nutrients in the industry. In this research, the physicochemical properties of modified Camellia oil (MCO) by enzymatic esterification were analyzed by Gas Chromatography-Mass Spectrometry (GC-MS), Differential Scanning Calorimetry (DSC), High Performance Liquid Chromatography-Evaporative Light Scattering Detection (HPLC-ELSD), and Ultra Performance Liquid Chromatography-Tandem Mass Spectrometry (UPLC-MS/MS). The relationship between reaction conditions and the DAG compositions is disclosed using multiple factors. It is found that high constituents of DAG increase the melting and crystallization temperature of MCO, lipase Novozym 435 gives the best yield of targeted nutrients (DAG, 1,3-DAG, LA-DAG), and the mixture of lipases, Lipozyme TL IM and Lipozyme RM IM, shows a synergistic effect in the synthetic process of DAG. Subsequently, MCO containing 65.4% DAG, 54.7% LA-DAG, and 47.6% 1,3-DAG content at optimal conditions (2% enzyme dosage, 4 h reaction time, 2.4:1 substrate molar ratio, 25.8% t-butanol as solvent, 60 • C temperature) has been obtained and purified using silica column to obtain the final DAG oil containing 96.1% DAG, 64.7% 1,3-DAG, and 78.4% LA-DAG. High constituents of structured DAG oil rich in LA-1,3-DAG can be obtained by enzymatic esterification for industrial production.

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Co-immobilization of bi-lipases on magnetic nanoparticles as an efficient catalyst for synthesis of functional oil rich in diacylglycerols, phytosterol esters and α-linolenic acid

Cited by 15 publications

References 31 publications

Lipases as Effective Green Biocatalysts for Phytosterol Esters’ Production: A Review

Lipases as Effective Green Biocatalysts for Phytosterol Esters’ Production: A Review

Structure‐guided preparation of fuctional oil rich in 1,3‐diacylglycerols and linoleic acid from Camellia oil by combi‐lipase

Fabrication, characterization, and purification of nutraceutical diacylglycerol components from Camellia oil

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