CN115281337A - Method for extracting oxidation-resistant astaxanthin from salmon - Google Patents
Method for extracting oxidation-resistant astaxanthin from salmon Download PDFInfo
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- CN115281337A CN115281337A CN202210930997.5A CN202210930997A CN115281337A CN 115281337 A CN115281337 A CN 115281337A CN 202210930997 A CN202210930997 A CN 202210930997A CN 115281337 A CN115281337 A CN 115281337A
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- 235000013793 astaxanthin Nutrition 0.000 title claims abstract description 122
- 229940022405 astaxanthin Drugs 0.000 title claims abstract description 120
- 239000001168 astaxanthin Substances 0.000 title claims abstract description 120
- JEBFVOLFMLUKLF-IFPLVEIFSA-N Astaxanthin Natural products CC(=C/C=C/C(=C/C=C/C1=C(C)C(=O)C(O)CC1(C)C)/C)C=CC=C(/C)C=CC=C(/C)C=CC2=C(C)C(=O)C(O)CC2(C)C JEBFVOLFMLUKLF-IFPLVEIFSA-N 0.000 title claims abstract description 119
- MQZIGYBFDRPAKN-ZWAPEEGVSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-ZWAPEEGVSA-N 0.000 title claims abstract description 113
- 241000972773 Aulopiformes Species 0.000 title claims abstract description 66
- 235000019515 salmon Nutrition 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 50
- 230000003647 oxidation Effects 0.000 title claims abstract description 14
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 14
- 235000013372 meat Nutrition 0.000 claims abstract description 33
- 238000010438 heat treatment Methods 0.000 claims abstract description 31
- 241000251468 Actinopterygii Species 0.000 claims abstract description 28
- 235000019688 fish Nutrition 0.000 claims abstract description 28
- 238000005470 impregnation Methods 0.000 claims abstract description 20
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 19
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 15
- 235000006708 antioxidants Nutrition 0.000 claims abstract description 15
- 239000008164 mustard oil Substances 0.000 claims abstract description 15
- 230000003197 catalytic effect Effects 0.000 claims abstract description 13
- JDLKFOPOAOFWQN-VIFPVBQESA-N Allicin Natural products C=CCS[S@](=O)CC=C JDLKFOPOAOFWQN-VIFPVBQESA-N 0.000 claims abstract description 11
- JDLKFOPOAOFWQN-UHFFFAOYSA-N allicin Chemical compound C=CCSS(=O)CC=C JDLKFOPOAOFWQN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000010081 allicin Nutrition 0.000 claims abstract description 11
- 238000005520 cutting process Methods 0.000 claims abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 70
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 48
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000741 silica gel Substances 0.000 claims description 16
- 229910002027 silica gel Inorganic materials 0.000 claims description 16
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- 229940079593 drug Drugs 0.000 claims description 2
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- 239000002778 food additive Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 2
- 238000003672 processing method Methods 0.000 claims 1
- OHDRQQURAXLVGJ-HLVWOLMTSA-N azane;(2e)-3-ethyl-2-[(e)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound [NH4+].[NH4+].S/1C2=CC(S([O-])(=O)=O)=CC=C2N(CC)C\1=N/N=C1/SC2=CC(S([O-])(=O)=O)=CC=C2N1CC OHDRQQURAXLVGJ-HLVWOLMTSA-N 0.000 abstract description 24
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 abstract description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 25
- -1 oxidation resistance Chemical compound 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 18
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
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- 238000007664 blowing Methods 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 230000007760 free radical scavenging Effects 0.000 description 8
- 238000002386 leaching Methods 0.000 description 8
- 238000002835 absorbance Methods 0.000 description 7
- 238000002791 soaking Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- MQZIGYBFDRPAKN-UWFIBFSHSA-N astaxanthin Chemical compound C([C@H](O)C(=O)C=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C(=O)[C@@H](O)CC1(C)C MQZIGYBFDRPAKN-UWFIBFSHSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
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- 239000006228 supernatant Substances 0.000 description 3
- 239000012224 working solution Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
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- 238000002156 mixing Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 2
- 230000002000 scavenging effect Effects 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000012864 cross contamination Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
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- 239000012153 distilled water Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
- 210000000663 muscle cell Anatomy 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 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
-
- 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
- A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
- A23L17/20—Fish extracts
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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Abstract
The invention discloses a method for extracting antioxidant astaxanthin from salmon, belonging to the technical field of astaxanthin processing. The method comprises the steps of cutting salmon into blocks, and performing mixed catalytic impregnation treatment in allicin and mustard oil to obtain catalyzed salmon; heating the catalyzed fish meat under a vacuum low-temperature condition; astaxanthin is extracted from the heated fish meat and purified to obtain astaxanthin with excellent oxidation resistance. The astaxanthin extracted by the method can eliminate more than 50 percent of ABTS free radicals and more than 90 percent of superoxide anion free radicals, and has strong oxidation resistance.
Description
Technical Field
The invention belongs to the technical field of astaxanthin processing, and particularly relates to a method for extracting antioxidant astaxanthin from salmon.
Background
The salmon belongs to highly swimming fishes in cold water, has the characteristics of high protein, high unsaturated fatty acid, high nutritional value and the like, contains minerals and vitamins required by a human body, and is delicious in taste. The muscle cells of salmon are rich in astaxanthin, which makes the salmon have a distinct orange-red color.
Astaxanthin is easily isomerized by environmental factors (temperature, ultraviolet rays, catalyst, etc.) due to its active electronic effect, i.e., all-trans astaxanthin is converted into cis-structure astaxanthin. The properties of the cis-structure astaxanthin such as oxidation resistance, anti-inflammation and biological accessibility are superior to those of trans-astaxanthin, 95 percent or more of natural astaxanthin in the salmon body is in a trans-structure, and the oxidation resistance and the biological activity of the natural astaxanthin are lower than those of the cis-structure.
Therefore, it is important to extract astaxanthin rich in cis-structure from salmon to improve the antioxidant properties of astaxanthin.
Disclosure of Invention
In view of the above, the present invention aims to provide a method for extracting astaxanthin rich in cis-structure from salmon, and the astaxanthin prepared by the method has high oxidation resistance, and the ability of the astaxanthin to remove ABTS free radicals and superoxide anion free radicals is significantly improved.
The invention provides a method for extracting antioxidant astaxanthin from salmon, which comprises the following steps:
(1) Cutting salmon into blocks, putting the cut salmon into a mixed solution of allicin and mustard oil, and carrying out vacuum catalytic impregnation to obtain catalyzed salmon meat;
(2) Heating the catalyzed salmon meat under a vacuum low-temperature condition; extracting astaxanthin from heated fish meat, and purifying.
Preferably, the vacuum degree of the vacuum catalytic impregnation in the step (1) is 0.05 Mpa-0.1 Mpa;
the vacuum catalytic impregnation time is 30-40 min.
Preferably, the size of the salmon block is 2cm x 4cm x 1cm-3cm x 7cm x 1cm.
Preferably, the weight percentage of the allicin in the mixed solution of the allicin and the mustard oil is 2-4%.
Preferably, the low-temperature heating time in the step (2) is 10-20 min, and the heating temperature is 50-60 ℃.
Preferably, the astaxanthin is extracted in the step (2) by repeatedly extracting the heated salmon meat with acetone/n-hexane as an extractant until the salmon meat is colorless.
Further preferably, the volume ratio of acetone to n-hexane in the extractant is 1.
Preferably, the astaxanthin purification method in the step (2) is to purify the extracted astaxanthin by using SPE-PAK normal phase silica gel column.
The invention also provides antioxidant astaxanthin, which is characterized by being prepared by the method of any one of claims 1 to 8. The content of the astaxanthin with a cis-structure in the antioxidant astaxanthin is obviously improved, and the occupation ratio is up to 17.4%.
The antioxidant astaxanthin can be used as a food additive and can also be used for preparing antioxidant medicines.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a method for extracting astaxanthin rich in cis-structure from salmon, which takes garlicin and mustard oil as catalysts and carries out immersion catalysis in a vacuum environment, thus improving the immersion rate and the catalysis effect of the catalysts; and then heating under a vacuum low-temperature condition, so that the content of cis-structure astaxanthin in the obtained astaxanthin is obviously improved, namely the oxidation resistance of the astaxanthin extract is improved. The ABTS free radical scavenging capacity of the astaxanthin extracted by the method is more than 50%, and the superoxide anion free radical scavenging capacity is more than 90%.
Meanwhile, in the extraction process of the astaxanthin, the allicin and the mustard oil are used as catalysts, so that the harm of biochemical catalysts and the like to health is avoided, the flavor of the salmon is enriched, and a new way is developed for the extraction process of the astaxanthin.
The preparation process has the advantages of simple operation, mild conditions, low production cost and high equipment utilization rate, and is very suitable for being applied to food production.
Detailed Description
The present invention will be described in detail with reference to the following examples so that the objects, features and advantages thereof will be more clearly understood. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
A method for extracting antioxidant astaxanthin from salmon comprises the following steps:
(1) Cutting salmon into blocks, putting the cut salmon into a mixed solution of allicin and mustard oil, and carrying out vacuum catalytic impregnation to obtain catalyzed salmon meat;
(2) Heating the catalyzed salmon meat under a vacuum low-temperature condition; extracting astaxanthin from heated fish meat, and purifying.
Preferably, the vacuum degree of the vacuum catalytic impregnation in the step (1) is 0.05 Mpa-0.1 Mpa;
the vacuum catalytic impregnation time is 30-40 min.
Preferably, the salmon fillet size is preferably 2 × 4 × 1 to 3cm × 7cm × 1cm, more preferably 2 × 4 × 1 to 2cm × 7cm × 1cm, more preferably 2 × 5 × 1 to 2cm × 6cm × 1cm. The vacuum degree of the immersed salmon block is preferably 0.05 to 0.1Mpa, more preferably 0.06 to 0.09Mpa, and still more preferably 0.07 to 0.08Mpa. The vacuum impregnation time is preferably 30 to 40min, more preferably 33 to 37min, and more preferably 35 to 36min.
The allicin accounts for 2-4% of the mixed liquid in the mixed liquid of the allicin and the mustard oil.
The method for draining the salmon block after catalytic impregnation is not particularly limited, and the drying and crushing scheme well known in the art can be adopted.
The method comprises the steps of heating the salmon chopsticks subjected to catalytic impregnation treatment at low temperature in vacuum, extracting astaxanthin from the heated fish, and purifying.
The time for low-temperature heating in the present invention is preferably 10 to 20min, more preferably 13 to 17min, and most preferably 15min. The heating temperature is preferably 50 to 60 ℃, more preferably 52 to 57 ℃.
The method for extracting astaxanthin in the invention utilizes acetone/n-hexane extraction, and the extraction is repeated until the astaxanthin is colorless.
The method comprises the step of purifying crude astaxanthin obtained after extraction through an SPE-PAK normal phase silica gel column to obtain purified astaxanthin. The eluent of the SPE-PAK normal phase silica gel column is preferably n-hexane and/or acetone.
The antioxidant property of the astaxanthin prepared is also tested in the invention. The detection includes scavenging ABTS radicals and superoxide anion radicals. Experimental results show that the ABTS free radical scavenging capacity of the astaxanthin prepared by the method is more than 50%, and the superoxide anion free radical scavenging capacity is more than 90%.
The method for improving the oxidation resistance of astaxanthin in salmon according to the present invention will be described in detail with reference to the following examples, which should not be construed as limiting the scope of the present invention
Example 1
A method for extracting astaxanthin with high oxidation resistance from salmon comprises the following steps:
(1) Dicing and vacuum impregnation of salmon: placing 2cm by 5cm by 1cm salmon block into a mixed solution of garlicin and mustard oil at a mass ratio of 3%, and catalytically soaking at 0.08Mpa in room temperature for 30min;
(2) Heating at low temperature in vacuum: draining the soaked fish, vacuumizing in a vacuum bag with a vacuum degree of 0.06Mpa (the treatment method can isolate oxygen, prevent the influence of cross contamination of microorganisms and chemicals on food in heating and storage processes, prolong the preservation time), heating at 55 deg.C for 15min, and cooling with running water to room temperature.
(3) Extraction of astaxanthin: weighing 5g of fish meat treated in the step (2), placing the fish meat in 25mL of acetone/n-hexane (1, v/v) mixed extracting solution for extraction, wherein the specific extraction method comprises the steps of homogenizing at the rotating speed of 10000rpm for 1min, centrifuging at the rotating speed of 4000rpm and the temperature of 4 ℃ for 5min, collecting supernate, and repeatedly extracting for 3 times until the supernate is colorless. Drying the extracting solution by using nitrogen, and then adding 3mL of n-hexane for redissolution;
(4) Activating a normal-phase silica gel column: purifying by SPE-PAK normal phase silica gel column, and activating with n-hexane in advance.
(5) Eluting astaxanthin: 3mL of the above-mentioned n-hexane-redissolved solution was sampled and eluted with 5mL of n-hexane to remove nonpolar impurities. Then eluting astaxanthin diester and astaxanthin monoester with n-hexane solution containing 5% and 10% acetone in sequence, and eluting the rest colored part with acetone.
(6) Nitrogen blowing: and collecting and combining the eluates, drying by blowing nitrogen, and redissolving by using ethanol to ensure that the concentration of the astaxanthin is 10mg/mL.
The extracted astaxanthin was subjected to a structural examination, and the relative content of trans-astaxanthin in the astaxanthin was 82.6% and cis-astaxanthin was 17.4%.
The ABTS method is adopted to determine the capability of the extracted astaxanthin to eliminate ABTS free radicals. The ABTS free radical scavenging method specifically comprises the following steps: 3mg ABTS was dissolved in 0.8mL deionized water and mixed and shaken to make ABTS stock solution. 1mgK 2 S 2 O 4 Stock potassium persulfate was prepared by mixing with 1.5mL of deionized water. The 0.2mL of the stock solution of LABTS and 0.2mL of the stock solution of potassium persulfate are mixed to prepare ABTS working solution, and the ABTS working solution is also cultured for 12 hours in a dark environment. Diluting by 30-60 times, and measuring the absorbance at the wavelength of 734nm to make the absorbance at the wavelength of 734nm between 0.7 and 0.8. mu.L of astaxanthin and 300. Mu.L of ABTS working solution were shaken and reacted for 10min in the dark, and the absorbance was measured at A734 nm.
And (3) measuring the capacity of the extracted astaxanthin for scavenging the superoxide anion free radicals by adopting a superoxide anion free radical scavenging method. Taking 4.5mL of 0.05mol/L Tris-HCl buffer solution with pH of 8.2 in a test tube, preheating for 20min in a water bath at 25 ℃, adding 1mL of astaxanthin extracting solution and 0.5mL of 2.5mmol/L pyrogallol, uniformly mixing, accurately reacting for 5min in the water bath at 25 ℃, immediately terminating the reaction by using 0.1mL of 8mol/L HCl, measuring the absorbance (A) value at the wavelength of 320nm, replacing the pyrogallol with 0.5mL of distilled water in a control group, and simultaneously setting a reagent blank tube.
In (A) 0 Refers to the absorbance of the blank, A i Refers to the absorbance, A, of the extract j Refers to the absorbance of the extract without pyrogallol.
The results show that the ABTS clearance of the astaxanthin after vacuum low-temperature treatment is 55.8%, the clearance of the superoxide anion free radical is 94.6%, the ABTS clearance of the astaxanthin without vacuum low-temperature heating is 36.9%, and the clearance of the superoxide anion free radical is 83.7% through calculation.
Example 2
A method for extracting astaxanthin with high oxidation resistance from salmon comprises the following steps:
(1) Dicing and vacuum impregnation of salmon: placing 2cm × 7cm × 1cm salmon block into 2% of mixed solution of garlicin and mustard oil, and catalytically soaking at 0.09Mpa for 35min;
(2) Heating at low temperature in vacuum: draining the fish meat after the soaking, placing into a vacuum bag, vacuumizing to 0.06Mpa, heating at 52 deg.C for 17min, and cooling salmon meat to room temperature with flowing water.
(3) Extracting astaxanthin: weighing 5g of the fish meat treated in the step (2), placing the fish meat into 25mL of acetone/n-hexane (1, v/v) mixed extracting solution for leaching, wherein the specific leaching method comprises the steps of homogenizing and homogenizing at the rotating speed of 10000rpm for 1min, centrifuging at the rotating speed of 4000rpm and at the temperature of 4 ℃ for 5min, collecting supernatant, and repeatedly extracting for 3 times until the fish meat is colorless. Drying the extracting solution by using nitrogen, and adding 3mL of n-hexane for redissolution;
(4) Activating a normal-phase silica gel column: purifying with SPE-PAK normal phase silica gel column, and activating with n-hexane.
(5) Eluting astaxanthin: 3mL of the above-mentioned n-hexane-redissolved solution was sampled and eluted with 5mL of n-hexane to remove nonpolar impurities. Then eluting astaxanthin diester and astaxanthin monoester with n-hexane solution containing 5% and 10% acetone in sequence, and eluting the rest colored part with acetone.
(6) Nitrogen blowing: and collecting and combining the eluates, drying by blowing nitrogen, and redissolving by using ethanol to ensure that the concentration of the astaxanthin is 10mg/mL.
ABTS free radical and superoxide anion free radical scavenging rates of astaxanthin after extraction were measured according to the method of example 1. The results show that the ABTS clearance of astaxanthin after vacuum low-temperature treatment is 52.2%, the clearance of superoxide anion free radicals is 91.4%, the ABTS clearance of astaxanthin without vacuum low-temperature heating is 36.9%, and the clearance of superoxide anion free radicals is 83.7% through calculation.
Example 3
A method for extracting astaxanthin with high oxidation resistance from salmon comprises the following steps:
(1) Dicing and vacuum impregnation of salmon: placing salmon block of 3cm by 5cm by 1cm size into mixed solution of garlicin and mustard oil at a mass ratio of 4%, and performing catalytic impregnation at room temperature of 0.06Mpa for 32min;
(2) Heating at low temperature in vacuum: draining the soaked fish, vacuum-pumping in a vacuum bag with a vacuum degree of 0.06Mpa, heating at 57 deg.C for 12min, and cooling with flowing water to room temperature.
(3) Extracting astaxanthin: weighing 5g of the fish meat treated in the step (2), placing the fish meat into 25mL of acetone/n-hexane (1, v/v) mixed extracting solution for leaching, wherein the specific leaching method comprises the steps of homogenizing and homogenizing at the rotating speed of 10000rpm for 1min, centrifuging at the rotating speed of 4000rpm and at the temperature of 4 ℃ for 5min, collecting supernatant, and repeatedly extracting for 3 times until the fish meat is colorless. Drying the extracting solution by using nitrogen, and adding 3mL of n-hexane for redissolution;
(4) Activating a normal-phase silica gel column: purifying with SPE-PAK normal phase silica gel column, and activating with n-hexane.
(5) Eluting astaxanthin: 3mL of the above-mentioned n-hexane-redissolved solution was sampled and eluted with 5mL of n-hexane to remove nonpolar impurities. Then eluting astaxanthin diester and astaxanthin monoester with n-hexane solution containing 5% and 10% acetone in sequence, and eluting the rest colored part with acetone.
(6) Nitrogen blowing: and collecting and combining the eluates, drying by blowing nitrogen, and redissolving by using ethanol to ensure that the concentration of the astaxanthin is 10mg/mL.
ABTS free radical and superoxide anion free radical scavenging rates of astaxanthin after extraction were measured according to the method of example 1. The results show that the ABTS clearance of the astaxanthin after vacuum low-temperature treatment is 53.7%, the clearance of the superoxide anion free radical is 92.8%, the ABTS clearance of the astaxanthin without vacuum low-temperature heating is 36.9%, and the clearance of the superoxide anion free radical is 83.7% through calculation.
Comparative example 1
A method for extracting astaxanthin from salmon comprises the following steps:
(1) Dicing and vacuum impregnation of salmon: placing 2cm by 5cm by 1cm salmon block into a mixed solution of garlicin and mustard oil at a mass ratio of 3%, and catalytically soaking at 0.08Mpa in room temperature for 35min;
(2) Heating at low temperature in vacuum: draining the soaked fish, vacuum-pumping in a vacuum bag with a vacuum degree of 0.06Mpa, heating at 60 deg.C for 20min, and cooling with flowing water to room temperature.
(3) Extracting astaxanthin: weighing 5g of fish meat treated in the step (2), placing the fish meat into 25mL of acetone solution for leaching, wherein the specific leaching method comprises the steps of homogenizing and homogenizing for 1min at the rotation speed of 10000rpm, centrifuging for 5min at the rotation speed of 4000rpm and the temperature of 4 ℃, collecting supernate, and repeatedly extracting for 3 times until the supernate is colorless. Drying the extracting solution by using nitrogen, and adding 3mL of n-hexane for redissolution;
(4) Activating a normal-phase silica gel column: purifying by SPE-PAK normal phase silica gel column, and activating with n-hexane in advance.
(5) Eluting astaxanthin: 3mL of the above-mentioned n-hexane-redissolved solution was sampled and eluted with 5mL of n-hexane to remove nonpolar impurities. Then eluting astaxanthin diester and astaxanthin monoester with n-hexane solution containing 5% and 10% acetone in sequence, and eluting the rest colored part with acetone.
(6) Nitrogen blowing: and collecting and combining the eluates, drying the eluates with nitrogen, and redissolving the eluates with ethanol to ensure that the concentration of the astaxanthin is 10mg/mL.
ABTS free radical and superoxide anion free radical clearance of astaxanthin after extraction was measured according to the method of example 1. The results show that the removal rate of the ABTS free radicals of the astaxanthin after vacuum low-temperature treatment is 40.2%, the removal rate of the superoxide anion free radicals is 84.3%, the removal rate of the ABTS of the astaxanthin without vacuum low-temperature heating is 36.9%, and the removal rate of the superoxide anion free radicals is 83.7% through calculation.
Comparative example 2
A method for extracting astaxanthin from salmon comprises the following steps:
(1) Dicing and vacuum impregnation of salmon: placing salmon block of 4cm × 7cm × 1cm size into mixed solution of garlicin and mustard oil at a mass ratio of 3%, and catalytically soaking at room temperature of 0.08Mpa for 30min;
(2) Heating at low temperature in vacuum: draining the fish meat after the soaking, placing into a vacuum bag, vacuumizing to 0.06Mpa, heating at 40 deg.C for 10min, and cooling salmon meat to room temperature with flowing water.
(3) Extraction of astaxanthin: weighing 5g of the fish meat treated in the step (2), placing the fish meat into 25mL of acetone/n-hexane (1, v/v) mixed extracting solution for leaching, wherein the specific leaching method comprises the steps of homogenizing and homogenizing at the rotating speed of 10000rpm for 1min, centrifuging at the rotating speed of 4000rpm and at the temperature of 4 ℃ for 5min, collecting supernatant, and repeatedly extracting for 3 times until the fish meat is colorless. Drying the extracting solution by using nitrogen, and adding 3mL of n-hexane for redissolution;
(4) Activating a normal-phase silica gel column: purifying with SPE-PAK normal phase silica gel column, and activating with n-hexane.
(5) Eluting astaxanthin: 3mL of the above-mentioned n-hexane-redissolved solution was sampled and eluted with 5mL of n-hexane to remove nonpolar impurities. Then eluting the astaxanthin diester and the astaxanthin monoester by using n-hexane solution containing 5 percent and 10 percent of acetone in sequence, and eluting the residual colored part by using acetone.
(6) Nitrogen blowing: and collecting and combining the eluates, drying by blowing nitrogen, and redissolving by using ethanol to ensure that the concentration of the astaxanthin is 10mg/mL.
ABTS free radical and superoxide anion free radical clearance of astaxanthin after extraction was measured according to the method of example 1. The results show that the ABTS clearance of the astaxanthin after vacuum low-temperature treatment is 40.8%, the clearance of the superoxide anion free radical is 84.2%, the ABTS clearance of the astaxanthin without vacuum low-temperature heating is 36.9%, and the clearance of the superoxide anion free radical is 83.7% through calculation.
Comparative example 3
A method for extracting astaxanthin from salmon comprises the following steps:
(1) Dicing and vacuum impregnation of salmon: placing salmon block of size 3cm × 5cm × 1cm into mixed solution of garlicin and mustard oil at mass ratio of 1%, and catalytically soaking at room temperature of 0.12Mpa for 25min;
(2) Heating at low temperature in vacuum: draining the soaked fish, vacuum-pumping in a vacuum bag with a vacuum degree of 0.06Mpa, heating at 50 deg.C for 15min, and cooling with flowing water to room temperature.
(3) Extracting astaxanthin: weighing 5g of fish meat treated in the step (2), placing the fish meat in 25mL of acetone/n-hexane (1, v/v) mixed extracting solution for extraction, wherein the specific extraction method comprises the steps of homogenizing at the rotating speed of 10000rpm for 1min, centrifuging at the rotating speed of 4000rpm and the temperature of 4 ℃ for 5min, collecting supernate, and repeatedly extracting for 3 times until the supernate is colorless. Drying the extracting solution by using nitrogen, and then adding 3mL of n-hexane for redissolution;
(4) Activating a normal-phase silica gel column: purifying by SPE-PAK normal phase silica gel column, and activating with n-hexane in advance.
(5) Eluting astaxanthin: 3mL of the above-mentioned n-hexane-redissolved solution was sampled and eluted with 5mL of n-hexane to remove nonpolar impurities. Then eluting the astaxanthin diester and the astaxanthin monoester by using n-hexane solution containing 5 percent and 10 percent of acetone in sequence, and eluting the residual colored part by using acetone.
(6) Nitrogen blowing: and collecting and combining the eluates, drying by blowing nitrogen, and redissolving by using ethanol to ensure that the concentration of the astaxanthin is 10mg/mL.
ABTS free radical and superoxide anion free radical clearance of astaxanthin after extraction was measured according to the method of example 1. The results show that the ABTS clearance of astaxanthin after vacuum low-temperature treatment is 42.3%, the clearance of superoxide anion free radicals is 84.4%, the ABTS clearance of astaxanthin without vacuum low-temperature heating is 36.9%, and the clearance of superoxide anion free radicals is 83.7% through calculation.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (10)
1. A method for extracting antioxidative astaxanthin from salmon is characterized by comprising the following steps:
(1) Cutting salmon into blocks, putting the cut salmon into a mixed solution of allicin and mustard oil, and carrying out vacuum catalytic impregnation to obtain catalyzed salmon meat;
(2) Heating the catalyzed salmon meat under a vacuum low-temperature condition; extracting astaxanthin from the heated fish meat, and purifying.
2. The method for extracting antioxidative astaxanthin from salmon as claimed in claim 1, wherein the degree of vacuum of the vacuum catalytic impregnation in the step (1) is 0.05Mpa to 0.1Mpa;
the time of the vacuum catalytic impregnation is 30-40 min.
3. The method of extracting antioxidant astaxanthin from salmon according to claim 1, wherein the salmon block size is from 2cm x 4cm x 1cm to 3cm x 7cm x 1cm.
4. The method of extracting antioxidant astaxanthin from salmon as claimed in claim 1, wherein the allicin in the mixture of allicin and mustard oil is 2-4% by weight of the mixture.
5. The method for extracting antioxidant astaxanthin from salmon as claimed in claim 1, wherein the time of low temperature heating in step (2) is 10-20 min, and the temperature of heating is 50-60 ℃.
6. The method for improving the oxidation resistance of astaxanthin in salmon as claimed in claim 1, wherein the method for extracting astaxanthin in step (2) is to repeatedly extract the heated salmon meat to colorless by using acetone/n-hexane as an extractant.
7. The processing method for improving the oxidation resistance of the astaxanthin in the salmon as claimed in claim 6, wherein the volume ratio of the acetone to the n-hexane in the extractant is 1.
8. The method for improving the oxidation resistance of astaxanthin in salmon according to claim 1, wherein the astaxanthin purification method in the step (2) is to purify the extracted astaxanthin by using SPE-PAK normal phase silica gel column.
9. An antioxidant astaxanthin, characterized by being produced by the method according to any one of claims 1 to 8.
10. Use of antioxidant astaxanthin according to claim 9 in food additives or in the preparation of antioxidant drugs.
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