CN111233727B - Biological preparation method of all-trans free astaxanthin - Google Patents
Biological preparation method of all-trans free astaxanthin Download PDFInfo
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Abstract
The invention belongs to the technical field of biological separation, and particularly relates to a biological preparation method of all-trans free astaxanthin. Collecting poultry eggs fed with the astaxanthin nutrition-enriched feed, separating egg yolks, and performing primary protein alcohol precipitation to obtain an astaxanthin protein compound; and after the first protein alcohol precipitation, performing second protein acid precipitation to obtain all-trans free astaxanthin. According to the invention, natural astaxanthin (ester) is subjected to biotransformation by utilizing laying hens, and two free astaxanthin products, namely an astaxanthin protein compound with high water solubility and all-trans free astaxanthin with high purity are obtained on the basis.
Description
The technical field is as follows:
the invention belongs to the technical field of biological separation, and particularly relates to a biological preparation method of all-trans free astaxanthin.
Background art:
astaxanthin is a naturally occurring carotenoid, has very strong antioxidant activity which is 550 times of that of vitamin E, is the strongest antioxidant found in nature, and can effectively eliminate oxidation products in cells, enhance the cell regeneration function, improve senile dementia, relieve chronic fatigue, improve cardiovascular diseases and the like. The current main sources of natural astaxanthin are marine crustaceans, fish, haematococcus pluvialis, phaffia rhodozyma, but naturally occurring astaxanthin exists in the form of astaxanthin esters and has poor bioavailability compared with free astaxanthin in digestion and absorption. The chemically synthesized astaxanthin is in a free form, so that the biological safety of the chemically synthesized astaxanthin is lower than that of natural astaxanthin, and the chemically synthesized astaxanthin cannot be directly added into food. Natural astaxanthin such as haematococcus pluvialis and the like is more widely used with excellent physiological functions and safety than chemically synthesized astaxanthin, but in order to solve the problem of low bioavailability of natural astaxanthin, it is necessary to convert astaxanthin in esterified form into free form.
At present, the preparation method of free astaxanthin at home and abroad mainly comprises saponification or enzymolysis after organic solvent extraction, and the method for extracting natural astaxanthin from raw materials mainly comprises ultrasonic extraction, supercritical carbon dioxide extraction, organic solvent extraction and the like, wherein the ultrasonic method and the supercritical method have the problems of complicated equipment, high cost and the like; the organic solvent extraction method mainly uses ethyl acetate, dichloromethane, n-hexane and other reagents, and the methods have the problems of large solvent consumption, complex process and the like, and the extracted astaxanthin has poor water solubility. However, in the food industry, there is no efficient enzyme for industrial production, and the saponification method has problems such as oxidative degradation and isomerization of astaxanthin, and thus the astaxanthin is oxidized into astaxanthin, and the structure of astaxanthin is destroyed.
In the astaxanthin nutrition-enriched biological product, the egg yolk of the poultry can enrich a large amount of astaxanthin, and the method is a very good way for biotransformation and utilization of the astaxanthin. In the prior art, as shown in patent 201811525974.6 "a method for producing natural astaxanthin egg yolk oil", astaxanthin enriched in poultry eggs exists in the yolk in an esterified state, namely astaxanthin ester, so that the extraction process mainly comprises the steps of extracting and purifying the egg yolk oil. However, in fact, the natural astaxanthin (ester) is subjected to specific biotransformation by the laying hens, and the existing form of the natural astaxanthin (ester) is changed. After the astaxanthin ester enters the intestinal tract, the ester bonds of fatty acid and astaxanthin are broken through the digestion of digestive enzyme, and the astaxanthin is changed into free astaxanthin which is combined with apolipoprotein in blood and transported to tissues and organs. During yolk formation, lipids accumulate in large amounts and the apolipoprotein transports astaxanthin into the yolk. The vitellin is involved in this process, and is combined with astaxanthin to form a free astaxanthin protein complex, which is then stably present in the yolk. The poultry eggs convert astaxanthin ester into free astaxanthin, so that the source diversity of natural astaxanthin is increased, and a new way is provided for the application of astaxanthin in food raw materials and food.
The natural trans-free astaxanthin is levorotatory astaxanthin, about 5% of haematococcus pluvialis astaxanthin is free astaxanthin, the structure of the natural trans-free astaxanthin is stable and is consistent with that of astaxanthin required in human bodies and animal bodies, the natural trans-free astaxanthin is easy to absorb, and various biological effects of the natural trans-free astaxanthin are exerted to the greatest extent. The astaxanthin synthesized by artificial mixing is only about 25 percent of levorotatory astaxanthin, the antioxidant effect is only one fourth of 100 percent of levorotatory astaxanthin, and the astaxanthin is not suitable for human bodies to take. Therefore, how to extract and obtain high-content all-trans free astaxanthin is a problem to be solved urgently.
The invention content is as follows:
the invention aims to solve the technical problems that the preparation method of free astaxanthin at home and abroad mainly comprises saponification or enzymolysis after organic solvent extraction, and the methods for extracting natural astaxanthin from raw materials mainly comprise ultrasonic extraction, supercritical carbon dioxide extraction, organic solvent extraction and the like, wherein the methods can oxidize astaxanthin into astaxanthin, and the astaxanthin structure is damaged.
In order to solve the problems, the natural astaxanthin (ester) is subjected to biotransformation by utilizing the laying hens, and two free astaxanthin products, namely an astaxanthin protein compound with high water solubility and all-trans free astaxanthin with high purity are obtained on the basis.
The invention is realized by the following technical means, and the biological preparation method of all-trans free astaxanthin is characterized in that poultry eggs fed with astaxanthin nutrition-enriched feed are collected, yolk is separated, and alcohol-soluble protein is removed through first protein alcohol precipitation to obtain an astaxanthin protein compound; removing alcohol insoluble protein by the second protein acid precipitation after the first protein acid precipitation to obtain all-trans free astaxanthin.
Wherein the astaxanthin after biotransformation is mainly enriched in yolk and exists in the form of astaxanthin protein complex after being combined with yolk protein. The main components of the yolk are 17.5% of protein, 32.5% of fat, about 48% of water and 2% of minerals, various vitamins and the like, after primary protein precipitation, alcohol-insoluble protein and minerals are removed in the precipitation, and alcohol-soluble protein, astaxanthin and lipid are remained in the extracting solution. Compared with the extraction method with dichloromethane, the loss rate of astaxanthin is 5.4%.
After the second protein precipitation, alcohol-soluble protein is removed, and the loss rate of astaxanthin is 6.1%.
Further, the first time of precipitating the protein alcohol is to precipitate egg yolk liquid according to a feed-liquid ratio of 1: (5-15) adding absolute ethyl alcohol, stirring and extracting for 1h, stirring, then carrying out 37-40 ℃ warm water bath for 0.5-1 h, centrifuging at the centrifugal speed of 2000-3000 rpm, and collecting clear liquid. The anhydrous ethanol is effective solvent for lipid extraction, and the combined lipid in the yolk can be better dispersed in the ethanol by warm water bath, so that the extraction efficiency is improved.
And further, carrying out reduced pressure concentration on the supernatant obtained after the first protein alcohol precipitation, wherein the concentration temperature is 45-70 ℃, and the vacuum degree is less than-0.1 Mpa, so as to obtain the water-soluble astaxanthin protein compound. And protecting with inert gas during concentration and solvent removal. The astaxanthin protein compound contains 20-40% of protein and 0.025-0.15% of all-trans free astaxanthin, and the astaxanthin and the egg yolk lipoprotein are combined together in a non-covalent bond mode to form the astaxanthin egg yolk lipoprotein compound. Such non-covalent bonding means include hydrogen bonding, van der waals force, weak interaction, etc., and the bonding force is weak. After the pH value in the solution is changed, amino acids in the protein are dissociated to a certain degree, the solubility of the protein is changed, and the non-covalent bond acting force between the astaxanthin is destroyed, so that the astaxanthin and the protein can be separated in a protein acid precipitation mode at the later stage.
And further, the second protein acid precipitation is to introduce the supernatant after the first protein alcohol precipitation into a secondary sedimentation tank, add hydrochloric acid to adjust the pH to 4.0-4.5, and carry out centrifugal sedimentation at the centrifugal speed of 2000-3000 rpm. And then introducing the supernatant obtained after centrifugation into an acid-base pool, adjusting the pH to 7.0 by using NaOH, carrying out centrifugal precipitation at a centrifugal speed of 2000-3000 rpm, and collecting the supernatant. Adding hydrochloric acid to adjust pH value of the solution to be near isoelectric point of alcohol-soluble protein, destroying non-covalent bond acting force between the alcohol-soluble protein and astaxanthin to precipitate protein, precipitating protein, and centrifuging to remove protein. NaOH is added to react with hydrochloric acid to generate NaCl, and the added hydrochloric acid is removed to restore the pH value to the original level.
And further, carrying out reduced pressure concentration on the supernatant obtained after the second protein acid precipitation, wherein the concentration temperature is 45-70 ℃, and the vacuum degree is less than-0.1 Mpa, so as to obtain the free astaxanthin grease. And protecting with inert gas during concentration and solvent removal. The astaxanthin oil contains a large amount of all-trans free astaxanthin, lecithin, fat-soluble vitamins, etc.
Further, when feeding the astaxanthin nutrition fortification feed, adding 5-20% haematococcus pluvialis algae powder into the poultry egg laying basal feed, and uniformly stirring by using a stirrer to fortify the astaxanthin nutrition of poultry eggs. With the prolonging of the feeding period, the color of the egg yolk is deepened, and the content of free astaxanthin is gradually increased. The astaxanthin in the poultry eggs reaches the stable level of 100-600 ug/g egg yolk after being fed for more than 15 days. The haematococcus pluvialis is fed to ensure that the obtained free astaxanthin is all-trans free astaxanthin and has higher and better biological activity.
Further, when egg yolk is separated, the egg yolk rich in astaxanthin is subjected to shelling treatment, the egg white and the egg yolk are separated, and the egg yolk is collected; and putting the yolk into a stirring tank, uniformly stirring, and entering a sedimentation tank of the next step.
The invention has the beneficial effects that:
(1) the invention takes haematococcus pluvialis as a raw material to obtain an astaxanthin biological product, and then extracts and prepares the astaxanthin in poultry eggs, and the obtained astaxanthin is all-trans free astaxanthin grease which has stable structure and is consistent with the structure of the astaxanthin required in human bodies and animal bodies, is beneficial to absorption and can exert various biological effects to the maximum extent.
(2) Astaxanthin is a fat-soluble compound, has low solubility in water, and brings certain difficulties to industrial development and utilization. The astaxanthin protein compound prepared by the preparation method disclosed by the invention is high in water solubility, the solubility of astaxanthin in the astaxanthin protein compound reaches 1.3mg/mL, and the application of astaxanthin in industrial production is increased.
(3) The safety of the astaxanthin is further improved through the biological screening effect of the poultry eggs.
(4) The astaxanthin in haematococcus pluvialis is converted into a free form by the chicken body, so that the bioavailability of the astaxanthin is enhanced. The extraction process has simple steps, the extraction efficiency after two times of precipitation is 89%, the solvent can be recycled, and the cost is low.
Drawings
FIG. 1 is an HPLC chromatogram of an all-trans free astaxanthin standard in example 1 of the present invention;
FIG. 2 is an HPLC chromatogram of an astaxanthin extract in example 2 of the present invention;
FIG. 3 is a standard curve of astaxanthin content versus peak area for HPLC.
The specific implementation mode is as follows:
in order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention are clearly and completely described below, and it is obvious that the described embodiments are a part of the embodiments of the present invention, but not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1:
(1) preparing astaxanthin nutrition biological raw materials: mixing Haematococcus pluvialis wall-broken algae powder and basal feed uniformly in a stirrer at a mixing ratio of 10:90, feeding laying hens for 15 days, and collecting eggs every day.
(2) Collecting poultry eggs, separating yolk and pretreating: removing shell of fowl egg, separating egg white and yolk with egg separator, collecting yolk, stirring about 30g of yolk, and stirring for 3 min.
(3) Collecting clear liquid by primary protein precipitation: adding 150ml of anhydrous ethanol, and extracting under stirring for 1 h. Stirring, extracting, performing 40 deg.C warm water bath for 1 hr, centrifuging in a centrifuge cup at 3000rpm for 3min, and collecting supernatant.
(5) Concentrating the astaxanthin extractive solution under vacuum degree of-0.1 Mpa, and removing solvent. Obtaining an astaxanthin protein compound extract, and detecting the content of all-trans free astaxanthin in the compound extracted from the eggs by high performance liquid chromatography according to the national standard GB T31520-2015 as shown in figure 1, wherein the content is measured to be 0.1%.
Example 2:
(1) obtaining astaxanthin poultry eggs: mixing haematococcus pluvialis non-wall-broken algae powder and laying hen basal feed uniformly in a stirrer at a ratio of 10:90, feeding laying hens for 20 days, and collecting eggs every day.
(2) Egg yolk collection pretreatment: the astaxanthin poultry eggs are subjected to shelling treatment, egg white and egg yolk are separated by an egg separator, the egg yolk is collected and then is put into a stirring tank to be fully and uniformly stirred.
(3) Primary protein precipitation: stirring, adding anhydrous ethanol, and stirring for 1 hr. Stirring for extraction, and extracting in 37 deg.C warm water bath for 1 hr. Centrifuging at 2000rpm for 5min, and collecting supernatant.
(4) Performing secondary protein precipitation on the clear liquid obtained in the step 3) and collecting the clear liquid: and (3) adding hydrochloric acid into the clear liquid obtained in the step (3) to adjust the pH value to 4.0-4.5, adding hydrochloric acid to enable the clear liquid to become turbid, centrifuging at the rotating speed of 3000rpm for 5min, adjusting the pH value of the centrifuged supernatant to 7.0 by using NaOH, stirring and uniformly mixing, centrifuging at the rotating speed of 3000rpm, and collecting the supernatant.
(5) The solvent is removed by concentration. Concentrating the astaxanthin extractive solution under vacuum degree of-0.1 Mpa, and removing solvent. Obtaining an astaxanthin extract, and detecting the content of the astaxanthin in the astaxanthin extract extracted from the eggs by using high performance liquid chromatography according to the national standard GB T31520-2015 as shown in figure 2 to obtain the yolk with the astaxanthin content of 354.9 ug/g.
The foregoing is directed to preferred embodiments of the present invention, other and further embodiments of the invention may be devised without departing from the basic scope thereof, and the scope thereof is determined by the claims that follow. However, any simple modification, equivalent change and modification of the above embodiments according to the technical essence of the present invention are within the protection scope of the technical solution of the present invention.
Claims (8)
1. A biological preparation method of all-trans free astaxanthin is characterized by comprising the following steps: collecting poultry eggs fed with the astaxanthin nutrition-enriched feed, separating egg yolks, and performing primary protein alcohol precipitation to obtain an astaxanthin protein compound; and after the first protein alcohol precipitation, performing second protein acid precipitation to obtain all-trans free astaxanthin.
2. The method for the biological production of all-trans free astaxanthin according to claim 1, characterized in that: the first time of precipitating the protein alcohol is to precipitate egg yolk liquid according to the feed-liquid ratio of 1: (5-15) adding absolute ethyl alcohol, stirring and extracting, carrying out warm water bath after stirring, then centrifuging, and collecting clear liquid.
3. The method for the biological production of all-trans free astaxanthin according to claim 1, characterized in that: and (3) carrying out reduced pressure concentration on the supernatant after the first protein alcohol precipitation to obtain a water-soluble astaxanthin protein compound.
4. The method for the biological production of all-trans free astaxanthin according to claim 1, characterized in that: the second protein acid precipitation is to add hydrochloric acid into the supernatant liquor after the first protein alcohol precipitation to adjust the pH value to 4.0-4.5, and carry out centrifugal precipitation; and then introducing the centrifuged supernatant into an acid-base pool, adjusting the pH to 7.0 by using NaOH, centrifuging and precipitating, and collecting the supernatant.
5. The method for the biological production of all-trans free astaxanthin according to claim 1, characterized in that: and (3) carrying out reduced pressure concentration on the supernatant obtained after the second protein acid precipitation, wherein the concentration temperature is 45-70 ℃, and the vacuum degree is less than-0.1 Mpa, so as to obtain the free astaxanthin grease.
6. A process for the biological production of all-trans free astaxanthin according to claim 3 or 5, characterized in that: and (3) protecting with inert gas during reduced pressure concentration.
7. The method for the biological production of all-trans free astaxanthin according to claim 1, characterized in that: when the astaxanthin nutrition strengthening feed is fed, 5 to 20 percent haematococcus pluvialis powder is added into the egg laying basic feed of poultry, and the mixture is uniformly stirred by a stirrer to strengthen the astaxanthin nutrition of poultry eggs.
8. The method for the biological production of all-trans free astaxanthin according to claim 1, characterized in that: separating egg yolk, removing shell of egg, separating egg white and egg yolk, and collecting egg yolk.
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| CN109258966A (en) * | 2018-11-12 | 2019-01-25 | 中铭生物科技(深圳)有限公司 | A method of improving egg natural astaxanthin content |
| CN109349451A (en) * | 2018-11-12 | 2019-02-19 | 中铭生物科技(深圳)有限公司 | A method of birds, which are fed, with haematococcus pluvialis improves astaxanthin biological conversion ratio |
| CN109456828A (en) * | 2018-12-13 | 2019-03-12 | 中铭生物科技(深圳)有限公司 | A kind of manufacturing method of natural astaxanthin egg oil |
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| CN109998979A (en) * | 2019-04-18 | 2019-07-12 | 中铭生物科技(深圳)有限公司 | A method of adding natural astaxanthin in cosmetics |
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| CN109258966A (en) * | 2018-11-12 | 2019-01-25 | 中铭生物科技(深圳)有限公司 | A method of improving egg natural astaxanthin content |
| CN109349451A (en) * | 2018-11-12 | 2019-02-19 | 中铭生物科技(深圳)有限公司 | A method of birds, which are fed, with haematococcus pluvialis improves astaxanthin biological conversion ratio |
| CN109456828A (en) * | 2018-12-13 | 2019-03-12 | 中铭生物科技(深圳)有限公司 | A kind of manufacturing method of natural astaxanthin egg oil |
| CN109601967A (en) * | 2018-12-13 | 2019-04-12 | 中铭生物科技(深圳)有限公司 | A kind of manufacturing method of high content astaxanthin low fat ratio mayonnaise |
| CN109998979A (en) * | 2019-04-18 | 2019-07-12 | 中铭生物科技(深圳)有限公司 | A method of adding natural astaxanthin in cosmetics |
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