Phospholipase A 1 -catalyzed hydrolysis of soy phosphatidylcholine to prepare l -α-glycerylphosphorylcholine in organic-aqueous media

Bang, Hyo Jeong; Kim, In Hwan; Kim, Byung Hee

doi:10.1016/j.foodchem.2015.05.093

Cited by 24 publications

(35 citation statements)

References 12 publications

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“…For the trial involving Novozym 435, the l ‐α‐GPC content in the reaction products obtained after 6 hr reached 100.0 area%, thereby indicating that PC was completely hydrolyzed to l ‐α‐GPC within the 6‐hr reaction. For the trial with Lecitase Ultra, which was used as the biocatalyst for l ‐α‐GPC production in our previous study, the l ‐α‐GPC content in the reaction products obtained at 12 hr was only 6.7 area%, although the reaction products contained 58.4 area% LPC, a partial hydrolysis derivative of PC (data not shown). No l ‐α‐GPC was found in the reaction products obtained using Lipozyme RM IM, Lipozyme TL IM, and C. rugosa lipase after 12 hr of reaction, although the reaction products contained 4.5, 0.2, and 0.1 area% of LPC, respectively (data not shown).…”

Section: Resultsmentioning

confidence: 95%

“…In the former case, an extracting solvent, such as diethyl ether, is used to remove the free fatty acids (FFA) that form during the reaction . The chromatographic method commonly utilizes column chromatography with an ionic or polar stationary phase and organic solvents (e.g., methanol) as a mobile phase to separate l ‐α‐GPC from substances with lower polarities …”

Section: Introductionmentioning

confidence: 99%

“…Recently, we demonstrated that the use of n ‐hexane–water biphasic media in enzymatic reaction systems for hydrolysis of soy PC to produce l ‐α‐GPC drastically increases the productivity because of the enhanced solubility of soy PC in the biphasic media . We used a microbial PLA 1 (in an aqueous solution form) called Lecitase Ultra as the biocatalyst.…”

Section: Introductionmentioning

confidence: 99%

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Enzymatic preparation of food‐grade l‐α‐glycerylphosphorylcholine from soy phosphatidylcholine or fractionated soy lecithin

Kim

Song

Lee

et al. 2019

Biotechnology Progress

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L-α-Glycerylphosphorylcholine (L-α-GPC) is a biosynthetic precursor for the neurotransmitter acetylcholine in humans, making it a useful as a cognitive enhancer for treating patients with stroke and dementia, including Alzheimer's disease. The aim of this study was to prepare L-α-GPC via Novozym 435 (an immobilized Candida antarctica lipase B)-catalyzed hydrolysis of soy phosphatidylcholine or a fractionated soy lecithin, from which triacylglycerols were completely removed, followed by foodgrade solvent extraction of L-α-GPC from the reaction products. The reaction was performed in n-hexane-water biphasic media in a stirred-batch reactor. Phosphatidylcholine was completely hydrolyzed to L-α-GPC under optimal conditions: temperature, 55 C; water content, 100 wt% of the substrate weight; enzyme loading, 10 wt % of the substrate weight; and reaction time of 6 hr (for soy phosphatidylcholine) or 8 hr (for fractionated soy lecithin). Water-soluble fractions of the reaction products containing 98.6 area% L-α-GPC (from soy phosphatidylcholine) or 52.4 area% glycerophosphodiesters, including L-α-GPC (from fractionated soy lecithin), were obtained after phase separation of the media. The resulting products would be suitable for use as food-grade cognitive enhancers because of the use of enzymatic reaction and food-grade solvent extraction. K E Y W O R D Sfood-grade cognitive enhancer, lecithin, L-α-glycerylphosphorylcholine, Novozym 435, phosphatidylcholine

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Section: Resultsmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Enzymatic preparation of food‐grade l‐α‐glycerylphosphorylcholine from soy phosphatidylcholine or fractionated soy lecithin

Kim

Song

Lee

et al. 2019

Biotechnology Progress

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“…Compared with the chemical method, the enzymatic production of GPC has several advantages, including high efficiency, excellent specificity, and environmental friendliness. In studies conducted by Bang et al [15], GPC was successfully prepared through the hydrolysis of soy PC with PLA 1 in a hexane-water biphasic medium. However, the organic Note: The enzyme activity at the optimum temperature and pH was defined as 100%.…”

Section: Gpc Synthesis and Optimisationmentioning

confidence: 99%

“…Several recent studies reported the production of GPC through the hydrolysis of PC using phospholipase A 1 (PLA 1 ) or a combination of lipase and phospholipase A 2 (PLA 2 ) [15][16][17][18]. Therefore, a novel enzymatic procedure utilising PLBs as biocatalysts has been developed for the production of GPC.…”

Section: Introductionmentioning

confidence: 99%

Cloning, expression and characterisation of phospholipase B fromSaccharomyces cerevisiaeand its application in the synthesis ofl-alpha-glycerylphosphorylcholine and peanut oil degumming

Liu

Huang

et al. 2018

Biotechnology & Biotechnological Equipment

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L-alpha-glycerylphosphorylcholine (GPC) has been shown to enhance cognitive performance. Meanwhile, vegetable oils must be refined to remove the impurities for them to be edible. Phospholipase B (PLB), having the ability of hydrolyzing both the sn-1 and sn-2 acyl ester bonds of phospholipids, can produce GPC using PC as substrate and transform the non-hydratable phospholipids into their hydratable forms. The Saccharomyces cerevisiae plb gene, which encodes PLB, was cloned and expressed in Pichia pastoris GS115 to produce recombinant PLB (rPLB). Fermentation optimisation yielded rPLB activity levels as high as 1723 U/mL. rPLB demonstrated maximum enzymatic activity at 40 C and pH 5.5 and was stable at temperatures between 30 and 40 C and pH values between 5.0 and 6.0. rPLB synthesised GPC with a conversion rate of 17% (w/ w) and exhibited high degumming activity towards peanut oil, decreasing the phosphorus content from 91.8 to 3.7 mg/kg within 3 h. This study describes a candidate phospholipase for potential applications involving the modification of phospholipids and vegetable oil degumming.

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Immobilized Talaromyces leycettanus phospholipase A₁ as a reusable biocatalyst for l‐α‐glycerylphosphorylcholine preparation from phosphatidylcholine

Kim,

See

et al. 2024

J Americ Oil Chem Soc

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Abstractl‐α‐Glycerylphosphorylcholine (l‐α‐GPC), a cognitive enhancer, can be prepared via phospholipase A1 (PLA1)‐catalyzed hydrolysis of soy phosphatidylcholine (PC). Quara LowP (QLP), a commercial liquid PLA1 from Talaromyces leycettanus, has not yet been used for the preparation of l‐α‐GPC. This study aimed to establish the optimal conditions for the immobilized QLP‐catalyzed hydrolysis of soy PC to prepare l‐α‐GPC and evaluate the reusability of the enzyme under these conditions. The immobilized QLP was prepared via physical adsorption onto Lewatit VP OC (LVO) 1600. The reaction was performed in n‐hexane–water biphasic media in a stirred‐batch reactor, achieving complete conversion to l‐α‐GPC. Optimal conditions included a temperature of 55°C, a soy PC‐to‐water molar ratio of 1:10, an enzyme loading (based on the protein quantity) of 10 mg/g soy PC, and a reaction time of 12 h. Gradual morphological alterations on the surface of the immobilized QLP, such as the formation of cracks and dents, were observed via scanning electron microscopy over six successive reuse cycles. Nevertheless, the immobilized QLP achieved complete conversion to l‐α‐GPC in its first reuse cycle under the optimal conditions up to the fifth cycle of reuse, with the extension of the reaction time to 60 h. These findings suggest that the LVO 1600‐immobilized QLP is a promising and reusable biocatalyst for the hydrolysis of soy PC to prepare l‐α‐GPC.

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Phospholipase A 1 -catalyzed hydrolysis of soy phosphatidylcholine to prepare l -α-glycerylphosphorylcholine in organic-aqueous media

Cited by 24 publications

References 12 publications

Enzymatic preparation of food‐grade l‐α‐glycerylphosphorylcholine from soy phosphatidylcholine or fractionated soy lecithin

Enzymatic preparation of food‐grade l‐α‐glycerylphosphorylcholine from soy phosphatidylcholine or fractionated soy lecithin

Cloning, expression and characterisation of phospholipase B fromSaccharomyces cerevisiaeand its application in the synthesis ofl-alpha-glycerylphosphorylcholine and peanut oil degumming

Immobilized Talaromyces leycettanus phospholipase A₁ as a reusable biocatalyst for l‐α‐glycerylphosphorylcholine preparation from phosphatidylcholine

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Phospholipase A 1 -catalyzed hydrolysis of soy phosphatidylcholine to prepare l -α-glycerylphosphorylcholine in organic-aqueous media

Cited by 24 publications

References 12 publications

Enzymatic preparation of food‐grade l‐α‐glycerylphosphorylcholine from soy phosphatidylcholine or fractionated soy lecithin

Enzymatic preparation of food‐grade l‐α‐glycerylphosphorylcholine from soy phosphatidylcholine or fractionated soy lecithin

Cloning, expression and characterisation of phospholipase B fromSaccharomyces cerevisiaeand its application in the synthesis ofl-alpha-glycerylphosphorylcholine and peanut oil degumming

Immobilized Talaromyces leycettanus phospholipase A1 as a reusable biocatalyst for l‐α‐glycerylphosphorylcholine preparation from phosphatidylcholine

Contact Info

Product

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Immobilized Talaromyces leycettanus phospholipase A₁ as a reusable biocatalyst for l‐α‐glycerylphosphorylcholine preparation from phosphatidylcholine