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Method for preparing high quality Antarctic krill oil rich in phosphatidylserine containing polyunsaturated double-bonded fatty acyl

A technology of phosphatidylserine and Antarctic krill oil, which is applied in the directions of producing fat, edible oil/fat, and fat oil/fat production, etc., can solve the problems of limited source of raw materials, unfavorable quality, low effective content, etc., and achieves simple and practical reaction, The effect of increasing the content and easy availability of raw materials

Inactive Publication Date: 2012-06-06
张永志
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, the enzymatic preparation of phosphatidylserine from soybean lecithin has been widely used, such as patent CN101230365A, but the product formed by this patent does not contain phosphatidylserine with polyunsaturated double bond long-chain fatty acyl groups
Patent CN101818179A synthesizes phosphatidylserine containing polyunsaturated double-bond fatty acyl groups from ordinary lecithin by two-step enzymatic method. Phospholipids in ordinary lecithin do not contain Omega-3 polyunsaturated fatty acyl groups. The reaction is to use phospholipase A1, A2 or lipase to catalyze fatty acids containing polyunsaturated double bonds and phosphatidylcholine in lecithin to generate phosphatidylcholine containing polyunsaturated double bond fatty acyl groups, and then use phospholipase D to catalyze The reaction of serine and the phosphatidylcholine containing polyunsaturated double-bond fatty acyl finally generates the phosphatidylserine containing polyunsaturated double-bond fatty acyl. The weak point of this invention is: raw material lecithin and polyunsaturated fatty acid It is a complex mixture in which the effective content of phosphatidylcholine and polyunsaturated fatty acid is not high. In the case of no high concentration, the effective content of these two raw materials is generally not more than 50%, while in phospholipase Under the catalysis of A2 or lipase specific to SN2 position, the probability of generating the target product SN2 position is phosphatidylcholine containing polyunsaturated double bond fatty acyl group is very low, which leads to the polyunsaturated double bond contained in the final product. The concentration of phosphatidylserine with bonded fatty acyl groups is lower, which is not conducive to the quality of the final product. If the active ingredient concentration of phosphatidylserine with polyunsaturated double bond fatty acyl groups in the product is to be increased, the production cost will be seriously increased
Patent CN100402656C uses phospholipid extracted from cod liver as raw material, patent CN101157946A uses phospholipid extracted from squid as raw material, adopts phospholipase D enzymatic method to catalyze phosphatidylcholine in cod liver or phosphatidylcholine in squid and L-serine reacts to prepare phosphatidylserine rich in polyunsaturated double-bond fatty acyl groups. Among them, phosphatidylcholine rich in polyunsaturated double-bond fatty acyl groups in cod liver phospholipid and squid phospholipid is the preparation of polyunsaturated double-bond fatty acyl-containing phosphatidylcholine. It is an excellent raw material for phosphatidylserine with fatty acyl groups, but the sources of these two raw materials are limited, which is not conducive to large-scale production

Method used

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  • Method for preparing high quality Antarctic krill oil rich in phosphatidylserine containing polyunsaturated double-bonded fatty acyl
  • Method for preparing high quality Antarctic krill oil rich in phosphatidylserine containing polyunsaturated double-bonded fatty acyl
  • Method for preparing high quality Antarctic krill oil rich in phosphatidylserine containing polyunsaturated double-bonded fatty acyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Example 1: Extraction of phosphatidylcholine rich in polyunsaturated double bond fatty acyl groups.

[0073] Weigh 20 kg of Antarctic krill oil, which contains 19.3% of EPA in phospholipids, 11.5% of DHA, 36.3% of PC, 1.5% of phosphatidylserine, and 40 liters of acetone. Add the above two raw materials to 100 Liter reactor, fill the reactor with nitrogen, under zero degrees Celsius, continuous mechanical stirring, 80

[0074] rpm, react for 2 to 15 hours, end the reaction, filter, freeze-dry the solid to obtain 13 kg of phosphatidylcholine rich in polyunsaturated double bond fatty acyl groups, of which: EPA is 18.3%, DHA is 8.1%, and the content of PC is 47.8%, the content of phosphatidylserine was 2.4%, and the filtrate was concentrated under reduced pressure at 20 degrees Celsius to remove the solvent to obtain 7 kg of red-brown oil.

Embodiment 2

[0075] Example 2: Refined Antarctic krill oil rich in phosphatidylserine

[0076] Weigh 10 kg of Antarctic krill oil, which contains 19.3% of EPA in phospholipids, 11.5% of DHA, 36.3% of PC, 1.5% of phosphatidylserine, 4 to 6 kg of L-serine, 0.1 to 0.8 kg Calcium chloride, 20 liters to 100 liters of water buffer in the range of pH 5.5 to pH 8.5, was added to a 150 liter reactor, under the protection of nitrogen, 0.1 to 1 liter of phospholipase D (about 20,000 to 50 Ten thousand units), within the range of 45-53 degrees Celsius, continuous mechanical stirring, 100rpm, reaction for 2 to 15 hours, stop stirring, end the reaction, add 10 to 50 kg of acetone, and then add 10 to 50 kg of n-heptane, continue mechanical stirring, 30rpm, 0.5 hours later, stop stirring, let stand for layering, take the organic phase, repeat the extraction 2 to 3 times according to the aforementioned method, gather the organic extracts, concentrate under reduced pressure at 20 degrees Celsius to obtain 9.5 ...

Embodiment 3

[0077] Example 3: Phosphatidylserine products rich in polyunsaturated double bond fatty acyl groups

[0078] Weigh 10 kg of Antarctic krill phosphatidylcholine prepared in Example 1. Among them, the phospholipid contains 18.3% of EPA, 8.1% of DHA, 47.8% of PC, 2.4% of phosphatidylserine, and 12 to 20 kg. L-serine, 0.4-1.5 kg calcium chloride, 50 liters to 120 liters of water buffer in the range of pH 5.5 to pH 8.5, added to a 150 liter reactor, under the protection of nitrogen, put in 0.1 to 2 liters of phospholipids Enzyme D 1 million units, within the range of 45-53 degrees Celsius, continuous mechanical stirring, 100rpm, reaction for 2 to 15 hours, to end the reaction, add 10 to 60 kg of ethanol, 10 to 60 kg of n-hexane, continuous mechanical stirring, 30 rpm, 0.5 After hours, stop stirring, let stand for layering, take the organic phase, repeat the extraction according to the aforementioned method for 2 to 4 times, pool the organic extracts, concentrate under reduced pressure...

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Abstract

The invention relates to a method for preparing a high quality Antarctic krill oil rich in phosphatidylserine containing polyunsaturated double-bonded fatty acyl. The method comprises the following steps: 1) carrying out solvent extraction on existing Antarctic krill oil to obtain phosphatidylcholine and oil containing vitamin A, vitamin E and astaxanthin; 2) preparing an enzyme catalysis reaction system, which is an aqueous phase reaction system; 3) adding the reaction system into a reactor, adding phospholipase D and carrying out mechanical agitation continuously; 4) extracting obtained reaction repeatedly and carrying out freeze drying on filtered solid to obtain phosphatidylserine rich in polyunsaturated double-bonded fatty acyl; 5) mixing the obtained phosphatidylserine rich in polyunsaturated double-bonded fatty acyl with the oil obtained in the step 1) to obtain the high quality Antarctic krill oil. The invention also provides a method for preparing phosphatidylcholine rich in polyunsaturated double-bonded fatty acyl from existing Antarctic krill oil and a method for preparing phosphatidylserine rich in polyunsaturated double-bonded fatty acyl.

Description

Technical field: [0001] The invention relates to a method for preparing high-quality Antarctic krill oil rich in phosphatidylserine with polyunsaturated double bond fatty acyl groups, and in particular to a method that uses phosphatidylcholine from Antarctic krill as a raw material and is catalyzed by an enzyme A method for preparing phosphatidylserine rich in polyunsaturated double bond fatty acyl groups and compounding it to obtain high-quality Antarctic krill oil. Background technique: [0002] In the prior art, there are many methods for preparing phosphatidylserine, among which extraction methods and enzyme conversion methods are the main methods. The extraction method is to extract phosphatidylserine from animal phospholipids, mainly using animal brains as raw materials. Patent CN1583766A is to extract phosphatidylserine from animal brain. However, due to mad cow disease and other reasons, the safety of its products has been suspected and has now been eliminated. In rece...

Claims

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Application Information

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IPC IPC(8): C12P7/64C12P13/06C07F9/10
CPCC11B1/10A23D9/04A23D9/013C11B3/003C12P13/06C12P7/6445C12P7/6472
Inventor 张永志王秀兰沈连红梁水英吴萍谢春定
Owner 张永志
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