CN111543641A - Method for improving stability and bioavailability of L-selenium-methyl selenocysteine - Google Patents
Method for improving stability and bioavailability of L-selenium-methyl selenocysteine Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002156 mixing Methods 0.000 claims abstract description 83
- 229920001503 Glucan Polymers 0.000 claims abstract description 45
- 239000011259 mixed solution Substances 0.000 claims abstract description 40
- 239000006185 dispersion Substances 0.000 claims abstract description 37
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims abstract description 34
- 235000010445 lecithin Nutrition 0.000 claims abstract description 34
- 239000000787 lecithin Substances 0.000 claims abstract description 34
- 229940067606 lecithin Drugs 0.000 claims abstract description 34
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 33
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 33
- 239000007788 liquid Substances 0.000 claims abstract description 18
- 239000000243 solution Substances 0.000 claims abstract description 18
- 238000004945 emulsification Methods 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000010413 sodium alginate Nutrition 0.000 claims abstract description 11
- 239000000661 sodium alginate Substances 0.000 claims abstract description 11
- 229940005550 sodium alginate Drugs 0.000 claims abstract description 11
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims abstract description 10
- 238000010008 shearing Methods 0.000 claims abstract description 9
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 40
- 238000003756 stirring Methods 0.000 claims description 32
- 235000006708 antioxidants Nutrition 0.000 claims description 31
- 235000012000 cholesterol Nutrition 0.000 claims description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 16
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 8
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 6
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 claims description 6
- 229930003268 Vitamin C Natural products 0.000 claims description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 6
- 235000019154 vitamin C Nutrition 0.000 claims description 6
- 239000011718 vitamin C Substances 0.000 claims description 6
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 229960001701 chloroform Drugs 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000004108 freeze drying Methods 0.000 claims description 4
- 239000005457 ice water Substances 0.000 claims description 4
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 4
- 238000002390 rotary evaporation Methods 0.000 claims description 4
- 229940014800 succinic anhydride Drugs 0.000 claims description 4
- XDSSPSLGNGIIHP-VKHMYHEASA-N Se-methyl-L-selenocysteine Chemical compound C[Se]C[C@H]([NH3+])C([O-])=O XDSSPSLGNGIIHP-VKHMYHEASA-N 0.000 claims description 2
- XDSSPSLGNGIIHP-UHFFFAOYSA-N Se-methyl-L-selenocysteine Natural products C[Se]CC(N)C(O)=O XDSSPSLGNGIIHP-UHFFFAOYSA-N 0.000 claims description 2
- 241001122767 Theaceae Species 0.000 claims description 2
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 claims description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 2
- 235000013824 polyphenols Nutrition 0.000 claims description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 claims 1
- ZKZBPNGNEQAJSX-REOHCLBHSA-N L-selenocysteine Chemical compound [SeH]C[C@H](N)C(O)=O ZKZBPNGNEQAJSX-REOHCLBHSA-N 0.000 claims 1
- 229930182853 L-selenocysteine Natural products 0.000 claims 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims 1
- 229940043253 butylated hydroxyanisole Drugs 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- 239000002861 polymer material Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000005457 optimization Methods 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000011669 selenium Substances 0.000 description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229910052711 selenium Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 239000003623 enhancer Substances 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010410 calcium alginate Nutrition 0.000 description 1
- 239000000648 calcium alginate Substances 0.000 description 1
- 229960002681 calcium alginate Drugs 0.000 description 1
- OKHHGHGGPDJQHR-YMOPUZKJSA-L calcium;(2s,3s,4s,5s,6r)-6-[(2r,3s,4r,5s,6r)-2-carboxy-6-[(2r,3s,4r,5s,6r)-2-carboxylato-4,5,6-trihydroxyoxan-3-yl]oxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate Chemical compound [Ca+2].O[C@@H]1[C@H](O)[C@H](O)O[C@@H](C([O-])=O)[C@H]1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O[C@H]2[C@H]([C@@H](O)[C@H](O)[C@H](O2)C([O-])=O)O)[C@H](C(O)=O)O1 OKHHGHGGPDJQHR-YMOPUZKJSA-L 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/16—Inorganic salts, minerals or trace elements
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- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/015—Inorganic compounds
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- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
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Abstract
The invention discloses a method for improving the stability and bioavailability of L-selenium-methyl selenocysteine, and relates to the technical field of high polymer materials. The preparation method comprises the steps of mixing L-selenium-methyl selenocysteine with water, adding a water-soluble antioxidant and sodium alginate to prepare an L-selenium-methyl selenocysteine mixed solution, then mixing lecithin with an oil-soluble antioxidant, adding modified glucan to prepare a lecithin mixed solution, finally mixing the L-selenium-methyl selenocysteine mixed solution with the lecithin mixed solution, adding a calcium chloride solution, and carrying out high-pressure shearing emulsification treatment to prepare the L-selenium-methyl selenocysteine dispersion solution. The L-selenium-methyl selenocysteine dispersion liquid prepared by the invention has better stability and bioavailability.
Description
Technical Field
The invention relates to the field of high polymer materials, in particular to a method for improving the stability and bioavailability of L-selenium-methyl selenocysteine.
Background
L-selenium-methyl selenocysteine is a novel selenium source food nutrition enhancer. In 2002, the U.S. FDA uses L-selenium-methyl selenocysteine as a dietary supplement of selenium for the first time. China also lists L-selenium-methyl selenocysteine in GB14880 nutrition enhancer list. However, since L-seleno-methylselenocysteine is very easy to absorb moisture and oxidize when exposed to air, it is very important to improve the stability of L-seleno-methylselenocysteine. In addition, since the substance is allowed to be taken in a small amount, in the microgram level, it is required to improve the bioavailability thereof in order to better exert the physiological function thereof.
Disclosure of Invention
The invention aims to provide a method for improving the stability and bioavailability of L-selenium-methyl selenocysteine, so as to solve the problems in the background technology.
In order to achieve the purpose, the invention provides the following technical scheme:
a method for improving the stability and bioavailability of L-selenium-methyl selenocysteine is characterized by mainly comprising the following processing steps:
(1) mixing L-selenium-methyl selenocysteine with water, adding water-soluble antioxidant and sodium alginate, stirring and mixing to obtain L-selenium-methyl selenocysteine mixed solution;
(2) mixing lecithin and oil-soluble antioxidant, adding modified glucan, stirring and mixing to obtain lecithin mixed solution;
(3) mixing the L-selenium-methyl selenocysteine mixed solution obtained in the step (1) with the lecithin mixed solution obtained in the step (2), adding a calcium chloride solution, and performing dispersion treatment to obtain an L-selenium-methyl selenocysteine dispersion solution;
(4) and (4) performing index analysis on the L-selenium-methyl selenocysteine dispersion liquid obtained in the step (3).
As optimization, the method for improving the stability and bioavailability of the L-selenium-methyl selenocysteine mainly comprises the following processing steps:
(1) mixing L-selenium-methyl selenocysteine and water according to the mass ratio of 1: 10-1: 20, mixing in a beaker, adding a water-soluble antioxidant with the mass of 0.1-0.2 time that of the L-selenium-methyl selenocysteine and sodium alginate with the mass of 0.2-0.5 time that of the L-selenium-methyl selenocysteine into the beaker, and stirring and mixing to obtain an L-selenium-methyl selenocysteine mixed solution;
(2) mixing lecithin and an oil-soluble antioxidant according to a mass ratio of 5: 1-20: 1, mixing the materials in a flask, adding modified glucan with the mass of 0.3-0.6 time that of lecithin into the flask, and stirring and mixing to obtain lecithin mixed liquor;
(3) mixing the L-selenium-methyl selenocysteine mixed solution obtained in the step (1) with the lecithin mixed solution obtained in the step (2) according to the mass ratio of 5: 1-20: 1, adding a calcium chloride solution with the mass fraction of 10% and the mass of 0.05 times that of the L-selenium-methyl selenocysteine mixed solution, and dispersing to obtain an L-selenium-methyl selenocysteine dispersion solution;
(4) and (4) performing index analysis on the L-selenium-methyl selenocysteine dispersion liquid obtained in the step (3).
As optimization, the method is characterized in that: the water-soluble antioxidant in the step (1) is any one of vitamin C or tea polyphenol.
Preferably, the oil-soluble antioxidant in the step (2) is any one of 2, 6-di-tert-butyl-4-methylphenol and butyl hydroxy anisole.
Preferably, the preparation method of the modified glucan in the step (2) comprises the following steps of firstly mixing cholesterol and pyridine according to a mass ratio of 1: 100, adding succinic anhydride with the mass being 1 time of that of cholesterol, stirring for reaction, then carrying out reduced pressure distillation to obtain a crude product, mixing the crude product with an ethanol solution with the mass fraction being 90%, filtering at the temperature of 50-80 ℃ to obtain a filtrate, recrystallizing the filtrate in ice water to obtain cholesterol-succinate, and mixing the cholesterol-succinate and trichloromethane according to the mass ratio of 1: 80, adding thionyl chloride which is 10 times of the weight of the cholesterol-succinate, controlling the adding speed of the thionyl chloride to be 5-8 mL/min, stirring for reaction, performing rotary evaporation and concentration to obtain pretreated cholesterol, and mixing the glucan and the dimethyl sulfoxide according to a mass ratio of 1: 250, adding ethylenediamine with the mass of 1-2 times of that of the glucan, stirring and mixing to obtain a glucan solution, and mixing the glucan solution and the pretreated cholesterol according to a mass ratio of 200: 1-300: 1, mixing, controlling the adding speed of the pretreated cholesterol to be 2-3 mL/min, stirring and reacting under the nitrogen atmosphere to obtain a modified glucan compound, dialyzing the modified glucan compound in water for 24 hours, and freeze-drying to obtain the modified glucan.
As optimization, the dispersion treatment in the step (3) is high-pressure shearing emulsification treatment or high-pressure homogeneous micro-jet treatment, and the conditions of the high-pressure shearing emulsification treatment are as follows: the temperature is 20-40 ℃, the pressure is 10-300MPa, the shearing speed is 10-500r/min, and the processing time is 30-3 h; the conditions of the high-pressure homogeneous micro-jet treatment are as follows: the temperature is 20-40 ℃, the pressure is 10-300MPa, and the flow is 50-500 mL/min.
Compared with the prior art, the invention has the beneficial effects that:
modified glucan is added when L-selenium-methyl selenocysteine dispersion liquid is prepared, and sodium alginate is added at the same time, firstly, the modified glucan is added, after the glucan is modified, one end of two ends of the glucan molecular weight is changed into a hydrophilic structure, the other end is changed into a hydrophobic structure, after lecithin mixed liquid is added, when the lecithin mixed liquid is mixed with the L-selenium-methyl selenocysteine mixed liquid, lecithin containing oil-soluble antioxidant is connected to the L-selenium-methyl selenocysteine containing water-soluble antioxidant, so that a vesicle result is formed in a product, and further the stability of the product is greatly improved, secondly, the sodium alginate is also added when the L-selenium-methyl selenocysteine dispersion liquid is prepared, after the sodium alginate is mixed with calcium chloride solution, and a layer of calcium alginate is covered on the surface of the vesicle formed by the modified glucan again, so that the stability of the product is further improved, and the bioavailability of the product is further improved.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and 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.
In order to more clearly illustrate the method of the present invention, the following examples are given, and the following examples are given as follows:
and (3) stability testing: the L-Se-methylselenocysteine dispersions obtained in the examples and the comparative products were tested for their Se content after the same storage time.
And (3) bioavailability test: the L-selenium-methylselenocysteine dispersions obtained in the examples and the comparative product were tested for selenium content at a dosage of 100 mg.
Example 1
A method for improving the stability and bioavailability of L-selenium-methylselenocysteine mainly comprises the following processing steps:
(1) mixing L-selenium-methyl selenocysteine and water according to the mass ratio of 1:15, mixing in a beaker, adding a water-soluble antioxidant with the mass of 0.2 time of that of the L-selenium-methyl selenocysteine and sodium alginate with the mass of 0.3 time of that of the L-selenium-methyl selenocysteine into the beaker, stirring and mixing for 30min under the conditions that the temperature is 45 ℃ and the rotating speed is 300r/min, and obtaining an L-selenium-methyl selenocysteine mixed solution;
(2) mixing lecithin and an oil-soluble antioxidant according to a mass ratio of 10: 1, mixing the materials in a flask, adding modified glucan with the mass of 0.4 time that of lecithin into the flask, and stirring and mixing the materials for 30min at the temperature of 60 ℃ and the rotating speed of 300r/min to obtain lecithin mixed solution;
(3) mixing the L-selenium-methyl selenocysteine mixed solution obtained in the step (1) with the lecithin mixed solution obtained in the step (2) according to the mass ratio of 10: 1, adding a calcium chloride solution with the mass fraction of 10 percent, which is 0.05 times of the mass of the L-selenium-methyl selenocysteine mixed solution, and performing dispersion treatment to obtain an L-selenium-methyl selenocysteine dispersion liquid;
(4) and (4) performing index analysis on the L-selenium-methyl selenocysteine dispersion liquid obtained in the step (3).
As optimization, the method is characterized in that: the water-soluble antioxidant in the step (1) is vitamin C.
Preferably, the oil-soluble antioxidant in the step (2) is 2, 6-di-tert-butyl-4-methylphenol.
Preferably, the preparation method of the modified glucan in the step (2) comprises the following steps of firstly mixing cholesterol and pyridine according to a mass ratio of 1: 100, adding succinic anhydride with the mass being 1 time of that of cholesterol, stirring for reaction, then carrying out reduced pressure distillation to obtain a crude product, mixing the crude product with an ethanol solution with the mass fraction being 90%, filtering at the temperature of 70 ℃ to obtain a filtrate, recrystallizing the filtrate in ice water to obtain cholesterol-succinate, and mixing the cholesterol-succinate and trichloromethane according to the mass ratio of 1: 80, adding thionyl chloride which is 10 times of the weight of the cholesterol-succinate, controlling the adding speed of the thionyl chloride to be 5-8 mL/min, stirring for reaction, performing rotary evaporation and concentration to obtain pretreated cholesterol, and mixing the glucan and the dimethyl sulfoxide according to a mass ratio of 1: 250, adding ethylenediamine with the mass of 1-2 times of that of the glucan, stirring and mixing to obtain a glucan solution, and mixing the glucan solution and the pretreated cholesterol according to a mass ratio of 280: 1, mixing, controlling the adding speed of the pretreated cholesterol to be 3mL/min, stirring and reacting under the nitrogen atmosphere to obtain a modified glucan compound, dialyzing the modified glucan compound in water for 24 hours, and freeze-drying to obtain the modified glucan.
Preferably, the dispersion treatment in the step (3) is high-pressure shear emulsification treatment, and the conditions of the high-pressure shear emulsification treatment are as follows: the temperature is 25 ℃, the pressure is 100MPa, the shearing speed is 400r/min, and the processing time is 10 h.
Example 2
A method for improving the stability and bioavailability of L-selenium-methylselenocysteine mainly comprises the following processing steps:
(1) mixing L-selenium-methyl selenocysteine and water according to the mass ratio of 1:15, mixing in a beaker, adding a water-soluble antioxidant with the mass of 0.2 time that of the L-selenium-methyl selenocysteine into the beaker, stirring and mixing for 30min under the conditions that the temperature is 45 ℃ and the rotating speed is 300r/min, and obtaining L-selenium-methyl selenocysteine mixed solution;
(2) mixing lecithin and an oil-soluble antioxidant according to a mass ratio of 10: 1, mixing the materials in a flask, adding modified glucan with the mass of 0.4 time that of lecithin into the flask, and stirring and mixing the materials for 30min at the temperature of 60 ℃ and the rotating speed of 300r/min to obtain lecithin mixed solution;
(3) mixing the L-selenium-methyl selenocysteine mixed solution obtained in the step (1) with the lecithin mixed solution obtained in the step (2) according to the mass ratio of 10: 1, adding a calcium chloride solution with the mass fraction of 10 percent, which is 0.05 times of the mass of the L-selenium-methyl selenocysteine mixed solution, and performing dispersion treatment to obtain an L-selenium-methyl selenocysteine dispersion liquid;
(4) and (4) performing index analysis on the L-selenium-methyl selenocysteine dispersion liquid obtained in the step (3).
As optimization, the method is characterized in that: the water-soluble antioxidant in the step (1) is vitamin C.
Preferably, the oil-soluble antioxidant in the step (2) is 2, 6-di-tert-butyl-4-methylphenol.
Preferably, the preparation method of the modified glucan in the step (2) comprises the following steps of firstly mixing cholesterol and pyridine according to a mass ratio of 1: 100, adding succinic anhydride with the mass being 1 time of that of cholesterol, stirring for reaction, then carrying out reduced pressure distillation to obtain a crude product, mixing the crude product with an ethanol solution with the mass fraction being 90%, filtering at the temperature of 70 ℃ to obtain a filtrate, recrystallizing the filtrate in ice water to obtain cholesterol-succinate, and mixing the cholesterol-succinate and trichloromethane according to the mass ratio of 1: 80, adding thionyl chloride which is 10 times of the weight of the cholesterol-succinate, controlling the adding speed of the thionyl chloride to be 5-8 mL/min, stirring for reaction, performing rotary evaporation and concentration to obtain pretreated cholesterol, and mixing the glucan and the dimethyl sulfoxide according to a mass ratio of 1: 250, adding ethylenediamine with the mass of 1-2 times of that of the glucan, stirring and mixing to obtain a glucan solution, and mixing the glucan solution and the pretreated cholesterol according to a mass ratio of 280: 1, mixing, controlling the adding speed of the pretreated cholesterol to be 3mL/min, stirring and reacting under the nitrogen atmosphere to obtain a modified glucan compound, dialyzing the modified glucan compound in water for 24 hours, and freeze-drying to obtain the modified glucan.
Preferably, the dispersion treatment in the step (3) is high-pressure shear emulsification treatment, and the conditions of the high-pressure shear emulsification treatment are as follows: the temperature is 25 ℃, the pressure is 100MPa, the shearing speed is 400r/min, and the processing time is 10 h.
Example 3
A method for improving the stability and bioavailability of L-selenium-methylselenocysteine mainly comprises the following processing steps:
(1) mixing L-selenium-methyl selenocysteine and water according to the mass ratio of 1:15, mixing in a beaker, adding a water-soluble antioxidant with the mass of 0.2 time of that of the L-selenium-methyl selenocysteine and sodium alginate with the mass of 0.3 time of that of the L-selenium-methyl selenocysteine into the beaker, stirring and mixing for 30min under the conditions that the temperature is 45 ℃ and the rotating speed is 300r/min, and obtaining an L-selenium-methyl selenocysteine mixed solution;
(2) mixing lecithin and an oil-soluble antioxidant according to a mass ratio of 10: 1, mixing the materials in a flask, stirring and mixing the materials for 30min at the temperature of 60 ℃ and the rotating speed of 300r/min to obtain lecithin mixed solution;
(3) mixing the L-selenium-methyl selenocysteine mixed solution obtained in the step (1) with the lecithin mixed solution obtained in the step (2) according to the mass ratio of 10: 1, adding a calcium chloride solution with the mass fraction of 10 percent, which is 0.05 times of the mass of the L-selenium-methyl selenocysteine mixed solution, and performing dispersion treatment to obtain an L-selenium-methyl selenocysteine dispersion liquid;
(4) and (4) performing index analysis on the L-selenium-methyl selenocysteine dispersion liquid obtained in the step (3).
As optimization, the method is characterized in that: the water-soluble antioxidant in the step (1) is vitamin C.
Preferably, the oil-soluble antioxidant in the step (2) is 2, 6-di-tert-butyl-4-methylphenol.
Preferably, the dispersion treatment in the step (3) is high-pressure shear emulsification treatment, and the conditions of the high-pressure shear emulsification treatment are as follows: the temperature is 25 ℃, the pressure is 100MPa, the shearing speed is 400r/min, and the processing time is 10 h.
Comparative example
A method for improving the stability and bioavailability of L-selenium-methylselenocysteine mainly comprises the following processing steps:
(1) mixing L-selenium-methyl selenocysteine and water according to the mass ratio of 1:15, mixing in a beaker, adding a water-soluble antioxidant with the mass of 0.2 time that of the L-selenium-methyl selenocysteine into the beaker, stirring and mixing for 30min under the conditions that the temperature is 45 ℃ and the rotating speed is 300r/min, and obtaining L-selenium-methyl selenocysteine mixed solution;
(2) mixing lecithin and an oil-soluble antioxidant according to a mass ratio of 10: 1, mixing the materials in a flask, stirring and mixing the materials for 30min at the temperature of 60 ℃ and the rotating speed of 300r/min to obtain lecithin mixed solution;
(3) mixing the L-selenium-methyl selenocysteine mixed solution obtained in the step (1) with the lecithin mixed solution obtained in the step (2) according to the mass ratio of 10: 1, adding a calcium chloride solution with the mass fraction of 10 percent, which is 0.05 times of the mass of the L-selenium-methyl selenocysteine mixed solution, and performing dispersion treatment to obtain an L-selenium-methyl selenocysteine dispersion liquid;
(4) and (4) performing index analysis on the L-selenium-methyl selenocysteine dispersion liquid obtained in the step (3).
As optimization, the method is characterized in that: the water-soluble antioxidant in the step (1) is vitamin C.
Preferably, the oil-soluble antioxidant in the step (2) is 2, 6-di-tert-butyl-4-methylphenol.
Preferably, the dispersion treatment in the step (3) is high-pressure shear emulsification treatment, and the conditions of the high-pressure shear emulsification treatment are as follows: the temperature is 25 ℃, the pressure is 100MPa, the shearing speed is 400r/min, and the processing time is 10 h.
Effect example 1
Table 1 below shows the results of stability performance analysis of the L-selenium-methylselenocysteine dispersions prepared in examples 1 to 3 of the present invention and comparative examples.
TABLE 1
Effect example 2
The following table 2 shows the results of the bioavailability performance analysis of the L-selenium-methylselenocysteine dispersions prepared in examples 1 to 3 of the present invention and the comparative example.
TABLE 2
From the comparison of experimental data of example 1 and comparative example in tables 1 and 2, it can be found that the addition of modified glucan in the preparation of L-selenium-methylselenocysteine dispersion, and the addition of antioxidant in both the aqueous phase and the oil phase, can effectively improve the stability of the product, and from the comparison of example 1 and comparative example 2, it can be found that the addition of sodium alginate can improve the stability of the product to some extent.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.
Claims (6)
1. A method for improving the stability and bioavailability of L-selenium-methyl selenocysteine is characterized by mainly comprising the following processing steps:
(1) mixing L-selenium-methyl selenocysteine with water, adding water-soluble antioxidant and sodium alginate, stirring and mixing to obtain L-selenium-methyl selenocysteine mixed solution;
(2) mixing lecithin and oil-soluble antioxidant, adding modified glucan, stirring and mixing to obtain lecithin mixed solution;
(3) mixing the L-selenium-methyl selenocysteine mixed solution obtained in the step (1) with the lecithin mixed solution obtained in the step (2), adding a calcium chloride solution, and performing dispersion treatment to obtain an L-selenium-methyl selenocysteine dispersion solution;
(4) and (4) performing index analysis on the L-selenium-methyl selenocysteine dispersion liquid obtained in the step (3).
2. The method for improving the stability and bioavailability of L-selenium-methylselenocysteine as claimed in claim 1, which mainly comprises the following steps:
(1) mixing L-selenium-methyl selenocysteine and water according to the mass ratio of 1: 10-1: 20, mixing in a beaker, adding a water-soluble antioxidant with the mass of 0.1-0.2 time that of the L-selenium-methyl selenocysteine and sodium alginate with the mass of 0.2-0.5 time that of the L-selenium-methyl selenocysteine into the beaker, and stirring and mixing to obtain an L-selenium-methyl selenocysteine mixed solution;
(2) mixing lecithin and an oil-soluble antioxidant according to a mass ratio of 5: 1-20: 1, mixing the materials in a flask, adding modified glucan with the mass of 0.3-0.6 time that of lecithin into the flask, and stirring and mixing to obtain lecithin mixed liquor;
(3) mixing the L-selenium-methyl selenocysteine mixed solution obtained in the step (1) with the lecithin mixed solution obtained in the step (2) according to the mass ratio of 5: 1-20: 1, adding a calcium chloride solution with the mass fraction of 10% and the mass of 0.05 times that of the L-selenium-methyl selenocysteine mixed solution, and dispersing to obtain an L-selenium-methyl selenocysteine dispersion solution;
(4) and (4) performing index analysis on the L-selenium-methyl selenocysteine dispersion liquid obtained in the step (3).
3. The method of claim 2, wherein the stability and bioavailability of L-se-methylselenocysteine is increased by: the water-soluble antioxidant in the step (1) is any one of vitamin C or tea polyphenol.
4. The method for improving the stability and bioavailability of L-selenocysteine according to claim 2, wherein the oil-soluble antioxidant in step (2) is any one of 2, 6-di-tert-butyl-4-methylphenol or butylated hydroxyanisole.
5. The method of claim 2, wherein the modified glucan obtained in step (2) is prepared by mixing cholesterol and pyridine in a mass ratio of 1: 100, adding succinic anhydride with the mass being 1 time of that of cholesterol, stirring for reaction, then carrying out reduced pressure distillation to obtain a crude product, mixing the crude product with an ethanol solution with the mass fraction being 90%, filtering at the temperature of 50-80 ℃ to obtain a filtrate, recrystallizing the filtrate in ice water to obtain cholesterol-succinate, and mixing the cholesterol-succinate and trichloromethane according to the mass ratio of 1: 80, adding thionyl chloride which is 10 times of the weight of the cholesterol-succinate, controlling the adding speed of the thionyl chloride to be 5-8 mL/min, stirring for reaction, performing rotary evaporation and concentration to obtain pretreated cholesterol, and mixing the glucan and the dimethyl sulfoxide according to a mass ratio of 1: 250, adding ethylenediamine with the mass of 1-2 times of that of the glucan, stirring and mixing to obtain a glucan solution, and mixing the glucan solution and the pretreated cholesterol according to a mass ratio of 200: 1-300: 1, mixing, controlling the adding speed of the pretreated cholesterol to be 2-3 mL/min, stirring and reacting under the nitrogen atmosphere to obtain a modified glucan compound, dialyzing the modified glucan compound in water for 24 hours, and freeze-drying to obtain the modified glucan.
6. The method for improving the stability and bioavailability of L-selenium-methylselenocysteine as claimed in claim 2, wherein the dispersion treatment in step (3) is high-pressure shear emulsification treatment or high-pressure homogeneous microjet treatment, and the conditions of the high-pressure shear emulsification treatment are as follows: the temperature is 20-40 ℃, the pressure is 10-300MPa, the shearing speed is 10-500r/min, and the processing time is 30-3 h; the conditions of the high-pressure homogeneous micro-jet treatment are as follows: the temperature is 20-40 ℃, the pressure is 10-300MPa, and the flow is 50-500 mL/min.
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