CN108420955A - Immobilized acidic ionic liquid extraction method of wheat germ phenol extract - Google Patents
Immobilized acidic ionic liquid extraction method of wheat germ phenol extract Download PDFInfo
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- CN108420955A CN108420955A CN201810089495.8A CN201810089495A CN108420955A CN 108420955 A CN108420955 A CN 108420955A CN 201810089495 A CN201810089495 A CN 201810089495A CN 108420955 A CN108420955 A CN 108420955A
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- 241000209140 Triticum Species 0.000 title claims abstract description 104
- 235000021307 Triticum Nutrition 0.000 title claims abstract description 104
- 238000000605 extraction Methods 0.000 title claims abstract description 29
- 239000011831 acidic ionic liquid Substances 0.000 title claims abstract description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title abstract description 13
- 150000002989 phenols Chemical class 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 17
- 238000002137 ultrasound extraction Methods 0.000 claims abstract description 17
- 102000004190 Enzymes Human genes 0.000 claims abstract description 16
- 108090000790 Enzymes Proteins 0.000 claims abstract description 16
- 239000000843 powder Substances 0.000 claims abstract description 15
- 230000009849 deactivation Effects 0.000 claims abstract description 10
- SZVJSHCCFOBDDC-UHFFFAOYSA-N ferrosoferric oxide Chemical compound O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 claims description 116
- 239000000243 solution Substances 0.000 claims description 41
- 210000001161 mammalian embryo Anatomy 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- 239000007788 liquid Substances 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 150000002500 ions Chemical class 0.000 claims description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002105 nanoparticle Substances 0.000 claims description 21
- 238000003756 stirring Methods 0.000 claims description 21
- 230000002378 acidificating effect Effects 0.000 claims description 19
- 229910052681 coesite Inorganic materials 0.000 claims description 18
- 229910052906 cristobalite Inorganic materials 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052682 stishovite Inorganic materials 0.000 claims description 18
- 229910052905 tridymite Inorganic materials 0.000 claims description 18
- 238000005238 degreasing Methods 0.000 claims description 17
- 239000008367 deionised water Substances 0.000 claims description 16
- 229910021641 deionized water Inorganic materials 0.000 claims description 16
- 239000011259 mixed solution Substances 0.000 claims description 15
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000002604 ultrasonography Methods 0.000 claims description 12
- 238000000227 grinding Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 7
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 claims description 7
- 238000005119 centrifugation Methods 0.000 claims description 6
- 238000000975 co-precipitation Methods 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 238000002390 rotary evaporation Methods 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000006228 supernatant Substances 0.000 claims description 6
- 238000000527 sonication Methods 0.000 claims description 5
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical class CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 claims description 5
- 239000012141 concentrate Substances 0.000 claims description 4
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims description 3
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- 238000004904 shortening Methods 0.000 abstract 1
- 238000009210 therapy by ultrasound Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 14
- 150000001299 aldehydes Chemical class 0.000 description 13
- JMSVCTWVEWCHDZ-UHFFFAOYSA-N syringic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1O JMSVCTWVEWCHDZ-UHFFFAOYSA-N 0.000 description 10
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 8
- PCMORTLOPMLEFB-ONEGZZNKSA-N sinapic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-ONEGZZNKSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 229940074391 gallic acid Drugs 0.000 description 7
- 235000004515 gallic acid Nutrition 0.000 description 7
- 150000007965 phenolic acids Chemical class 0.000 description 6
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 5
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- 229940074360 caffeic acid Drugs 0.000 description 5
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- YIBXWXOYFGZLRU-UHFFFAOYSA-N syringic aldehyde Natural products CC12CCC(C3(CCC(=O)C(C)(C)C3CC=3)C)C=3C1(C)CCC2C1COC(C)(C)C(O)C(O)C1 YIBXWXOYFGZLRU-UHFFFAOYSA-N 0.000 description 5
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 4
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 description 4
- DFYRUELUNQRZTB-UHFFFAOYSA-N Acetovanillone Natural products COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 4
- 235000001785 ferulic acid Nutrition 0.000 description 4
- 229940114124 ferulic acid Drugs 0.000 description 4
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 4
- PCMORTLOPMLEFB-UHFFFAOYSA-N sinapinic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-UHFFFAOYSA-N 0.000 description 4
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical class CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 3
- CWVRJTMFETXNAD-FWCWNIRPSA-N 3-O-Caffeoylquinic acid Natural products O[C@H]1[C@@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-FWCWNIRPSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- PZIRUHCJZBGLDY-UHFFFAOYSA-N Caffeoylquinic acid Natural products CC(CCC(=O)C(C)C1C(=O)CC2C3CC(O)C4CC(O)CCC4(C)C3CCC12C)C(=O)O PZIRUHCJZBGLDY-UHFFFAOYSA-N 0.000 description 3
- 238000013313 FeNO test Methods 0.000 description 3
- CWVRJTMFETXNAD-KLZCAUPSSA-N Neochlorogenin-saeure Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O CWVRJTMFETXNAD-KLZCAUPSSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 240000003152 Rhus chinensis Species 0.000 description 3
- 235000014220 Rhus chinensis Nutrition 0.000 description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 235000001368 chlorogenic acid Nutrition 0.000 description 3
- CWVRJTMFETXNAD-JUHZACGLSA-N chlorogenic acid Chemical compound O[C@@H]1[C@H](O)C[C@@](O)(C(O)=O)C[C@H]1OC(=O)\C=C\C1=CC=C(O)C(O)=C1 CWVRJTMFETXNAD-JUHZACGLSA-N 0.000 description 3
- 229940074393 chlorogenic acid Drugs 0.000 description 3
- FFQSDFBBSXGVKF-KHSQJDLVSA-N chlorogenic acid Natural products O[C@@H]1C[C@](O)(C[C@@H](CC(=O)C=Cc2ccc(O)c(O)c2)[C@@H]1O)C(=O)O FFQSDFBBSXGVKF-KHSQJDLVSA-N 0.000 description 3
- BMRSEYFENKXDIS-KLZCAUPSSA-N cis-3-O-p-coumaroylquinic acid Natural products O[C@H]1C[C@@](O)(C[C@@H](OC(=O)C=Cc2ccc(O)cc2)[C@@H]1O)C(=O)O BMRSEYFENKXDIS-KLZCAUPSSA-N 0.000 description 3
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- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 3
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
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- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 2
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- 229920002488 Hemicellulose Polymers 0.000 description 1
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 description 1
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 description 1
- 101710172711 Structural protein Proteins 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002213 flavones Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000010808 liquid waste Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- -1 trimethoxyl silicon Alkane Chemical class 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/88—Liliopsida (monocotyledons)
- A61K36/899—Poaceae or Gramineae (Grass family), e.g. bamboo, corn or sugar cane
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/10—Preparation or pretreatment of starting material
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/35—Extraction with lipophilic solvents, e.g. Hexane or petrol ether
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/53—Liquid-solid separation, e.g. centrifugation, sedimentation or crystallization
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Medicinal Chemistry (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cosmetics (AREA)
Abstract
The invention provides an immobilized acidic ionic liquid extraction method of a wheat germ phenol extract, which comprises the steps of firstly adopting a microwave enzyme deactivation mode to process fresh wheat germs after the fresh wheat germs are obtained, aiming at inactivating oxidase in the wheat germs so as to avoid the oxidation of wheat germ phenol substances in a solution, adopting an ultramicro crushing method to crush wheat germ cell walls, improving the solubility of wheat germ powder in the solution, improving the hydrolysis efficiency of immobilized acidic ionic liquid, shortening the time of ultrasonic auxiliary extraction, preparing magnetic iron oxide nano particles which are easy to recycle and have high hydrolysis efficiency and are modified with acidic ionic liquid on the surfaces, preprocessing the wheat germs in the solution, aiming at converting bound-state phenol substances into extractable free-state phenols, examining the conditions of ultrasonic extraction of phenols, finally determining the ultrasonic power to be 48-76W, ultrasonic treatment is carried out for 20-30 min at 30-40 deg.C.
Description
Technical field
The present invention is a kind of immobilization acidic ion liquid extraction method of wheat embryo phenols extract, belongs to software user
Method field.
Background technology
Aldehydes matter is the secondary metabolites being widely present in plant, is generally to have anti-oxidant, anticancer, prevent the heart
The bioactive substance of the functions such as vascular diseases, and generally without toxicity.Wheat embryo is the by-product of flour processing, sense of food compared with
Difference, storage period is shorter, but aldehydes matter type is compared with horn of plenty in wheat embryo, such as ferulic acid, p-Coumaric Acid, syringic acid, perfume (or spice)
Oxalic acid, syringic acid, sinapic acid, Quercetin, flavones and gallic acid, carotenoid, tocopherol etc..Therefore from snacks plumule
The phenols extract with bioactive functions is extracted, the depth of wheat embryo resource is contributed to excavate and rationally utilize.
Research shows that the aldehydes matter in plant part exists in the form of three kinds of free state, solvable free state and bound state.
Wherein the aldehydes matter of bound state is substantially mutually tied in the form of glycosidic bond, ester bond, ether glycosidic bond with other substances, such as albumen, carbohydrate
It closes.Research shows that the phenols of free state is often more stronger than the phenols inoxidizability of bound state.The extraction side of common aldehydes matter
Method, if the purpose of acid and alkali hydrolysis method, microwave loss mechanisms, enzymatic isolation method, fermentation method substantially is all the fibre destroyed in plant cell wall
The compact texture for tieing up the formation such as element, hemicellulose, structural proteins, lignin, to discharge the aldehydes matter of bound state.Obviously
Ground, there are inefficient, liquid waste processing is difficult, takes the defects of longer, cost is higher for these extracting methods.For example, soda acid water
Treated that devil liquor recovery is more difficult for solution, and the cost of enzymatic isolation method is excessively high and enzyme is difficult to recycle and reuse, fermentation method
Transformation efficiency is not high.Be easily recycled therefore, it is necessary to developing one kind, reusable, extraction efficiency is high, it is of low cost, have
The extracting method of the plant source aldehydes matter of production application future.
Invention content
In view of the deficienciess of the prior art, it is an object of the present invention to provide a kind of immobilizations of wheat embryo phenols extract
Acidic ionic liquid extraction method, to solve the problems mentioned in the above background technology.
To achieve the goals above, the present invention is to realize by the following technical solutions：A kind of wheat embryo phenols carries
The immobilization acidic ion liquid extraction method for taking object, includes the following steps：
Step 1, enzyme deactivation：Fresh, the mildew and rot rotten wheat embryo of nothing is selected, is laid on microwave tray, at microwave
1-5 min are managed, microwave power is 550-1000 W；
Step 2, degreasing：Defatted wheat germ is obtained using n-hexane pressuring method, defatted wheat germ dries rear ultramicro grinding and obtains degreasing
Wheat germ powder；
Step 3, converting constraint phenols in wheat germ using Fe3O4@SiO2- [MIM] HSO4 becomes free state phenols：By the table of preparation
The magnetic ferroferric oxide nano-particles of acidic ionic liquid are modified in face, i.e. Fe3O4@SiO2- [MIM] HSO4 are with certain mass ratio
It is mixed in deionized water with the defatted wheat germ powder after crushing, is protected from light stirring 5-15 h, after reaction, using electromagnet to mixed
Close the magnetic Fe in solution3O4@SiO2-[MIM]HSO4It is recycled；
Step 4, the ultrasonic extraction of wheat embryo phenols：Isometric absolute ethyl alcohol is poured into the wheat germ solution obtained to step 3,
Mixed solution is under conditions of 10-40 DEG C of temperature, ultrasonic extraction 5-30 min, and ultrasonic power is 48-76 W, and ultrasound mode is super
It is spaced 10 s after 10 s of sonication；
Step 5, dehydration concentration：By the mixed liquor low-temperature centrifugation 10-30 min obtained by above-mentioned steps, the decompression rotation of gained supernatant
Evaporation, concentrate is freeze-dried to obtain powdered extract, as wheat germ phenols extract.
Further, in step 2, the mass ratio of defatted wheat germ and n-hexane is 1:4-1：15, degreasing time 30-120
Min, skimming temp are 5-30 DEG C.
Further, in step 2, the time of defatted wheat germ ultramicro grinding is 5-20 min.
Further, in step 3, the preparations of magnetic ferric oxide nano particles uses coprecipitation, i.e., to containing divalent and
Ferric ion mole is 1.75-2:Alkaline solution is added in 1 salting liquid, adjusts pH within the scope of 11-13, is stirred continuously life
At black floccule, the crystallization 1-5 h under 100-140 DEG C of temperature condition, it is heavy to generate black magnetic iron oxide nano-particle later
It forms sediment, is washed repeatedly using electromagnet adsorption of nanoparticles and with deionized water, magnetic ferric oxide nano grain is obtained after low temperature drying
Son.
Further, in step 3, acidic ionic liquid [MIM] HSO4Preparation process be：1- methylimidazoles are dissolved in anhydrous
In acetonitrile, be slowly added to the concentrated sulfuric acid under the conditions of -10 to 0 DEG C and slowly stir, fully reaction after with toluene wash three times and very
The dry 2-8 h of sky, obtain [MIM] HSO4。
Further, in step 3, Fe3O4@SiO2Synthesis mode be：By Fe3O4It is dissolved in deionized water, is ultrasonically treated mixed
Silester is added dropwise after closing solution and stirs 5-10 h at 30 DEG C, electromagnet is collected product and washed for several times, after dry
Obtain powdered Fe3O4@SiO2。
Further, in step 3, Fe3O4@SiO2-[MIM]HSO4Preparation process be：By 3- r-chloropropyl trimethoxyl silicon
Alkane and Fe3O4@SiO2Toluene is dissolved in and 36 h that flow back, later by acidic ionic liquid obtained [MIM] HSO4It is dissolved in absolute ethyl alcohol
And mix two kinds of solution, mixed liquor is ultrasonically treated 20-60 min, and stands 15-25 h at 40-65 DEG C and obtain Fe3O4@
SiO2-[MIM]HSO4。
Further, in step 3, Fe3O4@SiO2-[MIM]HSO4Mass ratio with defatted wheat germ powder is 1：5-1：50.
Further, in step 4, during ultrasonic extraction, solution temperature is 40-60 DEG C, sonication treatment time 40-
240 min。
Further, the low-temperature centrifugation rotating speed described in step 5 is 4000-12000 r/min, and temperature is 4-10 DEG C, institute
It is 5-20 h to state the rotary evaporation time, and temperature is 50-60 DEG C.
Beneficial effects of the present invention：A kind of immobilization acidic ion liquid extraction of wheat embryo phenols extract of the present invention
Method,（1）After obtaining fresh wheat embryo, handled by the way of microwave deactivating enzyme first, it is therefore intended that in wheat germ
Oxidation enzyme-deactivating, to avoid the oxidation of wheat germ aldehydes matter in the solution.（2）Keep wheat germ thin using the method for ultramicro grinding
Cell wall is broken, improves the dissolubility of wheat germ powder in the solution, improves the hydrolysis efficiency of immobilization acidic ion liquid, and shortens super
The time of sound assisted extraction.(3) surface modification for being prepared for being easily recycled, hydrolysis efficiency is high has the magnetic oxygenated of acidic ionic liquid
Fe nanometer particles in the solution pre-process wheat germ, it is therefore intended that convert the aldehydes matter of bound state to extractible trip
Amorph phenols.（4）Although ultrasound can improve aldehydes matter extraction efficiency, certain phenols, such as caffeic acid be easy compared with
It degrades during the ultrasonic extraction of high-energy, therefore the present invention has investigated the condition of ultrasonic extraction phenols, it is final to determine ultrasonic work(
Rate is 48-76 W, and ultrasonic time 20-30 min, temperature range is 30-40 DEG C.（5）The present invention is reproducible, and operation is more simple
Just, extraction efficiency is high.
Description of the drawings
Upon reading the detailed description of non-limiting embodiments with reference to the following drawings, other feature of the invention, purpose
It will be become more apparent upon with advantage：
Fig. 1 is the Fe measured at room temperature in the embodiment of the present invention 13O4@SiO2-[MIM]HSO4Hysteresis loop；
Fig. 2 is the Fe measured at room temperature in the embodiment of the present invention 23O4@SiO2-[MIM]HSO4Hysteresis loop；
Fig. 3 is the Fe measured at room temperature in the embodiment of the present invention 33O4@SiO2-[MIM]HSO4Hysteresis loop.
Specific implementation mode
To make the technical means, the creative features, the aims and the efficiencies achieved by the present invention be easy to understand, with reference to
Specific implementation mode, the present invention is further explained.
The present invention provides a kind of technical solution：A kind of immobilization acidic ion liquid extraction of wheat embryo phenols extract
Method includes the following steps：
Step 1, enzyme deactivation：Fresh, the mildew and rot rotten wheat embryo of nothing is selected, is laid on microwave tray, at microwave
1-5 min are managed, microwave power is 550-1000 W；
Step 2, degreasing：Defatted wheat germ is obtained using n-hexane pressuring method, defatted wheat germ dries rear ultramicro grinding and obtains degreasing
Wheat germ powder；
Step 3, using Fe3O4@SiO2-[MIM]HSO4Converting constraint phenols in wheat germ becomes free state phenols：By the table of preparation
The magnetic ferroferric oxide nano-particles of acidic ionic liquid, i.e. Fe are modified in face3O4@SiO2-[MIM]HSO4With certain mass ratio
It is mixed in deionized water with the defatted wheat germ powder after crushing, is protected from light stirring 5-15 h, after reaction, using electromagnet to mixed
Close the magnetic Fe in solution3O4@SiO2-[MIM]HSO4It is recycled；
Step 4, the ultrasonic extraction of wheat embryo phenols：Isometric absolute ethyl alcohol is poured into the wheat germ solution obtained to step 3,
Mixed solution is under conditions of 10-40 DEG C of temperature, ultrasonic extraction 5-30 min, and ultrasonic power is 48-76 W, and ultrasound mode is super
It is spaced 10 s after 10 s of sonication；
Step 5, dehydration concentration：By the mixed liquor low-temperature centrifugation 10-30 min obtained by above-mentioned steps, the decompression rotation of gained supernatant
Evaporation, concentrate is freeze-dried to obtain powdered extract, as wheat germ phenols extract.
In step 2, the mass ratio of defatted wheat germ and n-hexane is 1:4-1：15, degreasing time is 30-120 min, degreasing
Temperature is 5-30 DEG C.
In step 2, the time of defatted wheat germ ultramicro grinding is 5-20 min.
In step 3, the preparations of magnetic ferric oxide nano particles uses coprecipitation, i.e., to containing divalent and ferric ion
Mole be 1.75-2:Alkaline solution is added in 1 salting liquid, adjusts pH within the scope of 11-13, it is cotton-shaped to be stirred continuously generation black
Object, the crystallization 1-5 h under 100-140 DEG C of temperature condition, generate black magnetic iron oxide nano-particle precipitation, use electromagnetism later
Iron adsorption of nanoparticles is simultaneously washed with deionized water repeatedly, and magnetic ferric oxide nano particles are obtained after low temperature drying.
In step 3, acidic ionic liquid [MIM] HSO4Preparation process be：1- methylimidazoles are dissolved in anhydrous acetonitrile,
It is slowly added to the concentrated sulfuric acid under the conditions of -10 to 0 DEG C and slowly stirs, fully washed three times with toluene after reaction and is dried in vacuo 2-
8 h obtain [MIM] HSO4。
In step 3, Fe3O4@SiO2Synthesis mode be：By Fe3O4Be dissolved in deionized water, be ultrasonically treated after mixed solution by
It is added dropwise to silester and stirs 5-10 h at 30 DEG C, electromagnet is collected product and washed for several times, is obtained after dry powdered
Fe3O4@SiO2。
In step 3, Fe3O4@SiO2-[MIM]HSO4Preparation process be：By 3- r-chloropropyl trimethoxyl silanes and Fe3O4@
SiO2Toluene is dissolved in and 36 h that flow back, later by acidic ionic liquid obtained [MIM] HSO4It is dissolved in absolute ethyl alcohol and molten by two kinds
Liquid mixes, and mixed liquor is ultrasonically treated 20-60 min, and stands 15-25 h at 40-65 DEG C and obtain Fe3O4@SiO2-[MIM]
HSO4。
In step 3, Fe3O4@SiO2-[MIM]HSO4Mass ratio with defatted wheat germ powder is 1：5-1：50.
In step 4, during ultrasonic extraction, solution temperature is 40-60 DEG C, and sonication treatment time is 40-240 min.
Low-temperature centrifugation rotating speed described in step 5 is 4000-12000 r/min, and temperature is 4-10 DEG C, the rotary evaporation
Time is 5-20 h, and temperature is 50-60 DEG C.
As an embodiment of the present invention：（1）After obtaining fresh wheat embryo, the side of microwave deactivating enzyme is used first
Formula is handled, it is therefore intended that the oxidation enzyme-deactivating in wheat germ, to avoid the oxidation of wheat germ aldehydes matter in the solution.
（2）Keep wheat germ cell wall broken using the method for ultramicro grinding, improves the dissolubility of wheat germ powder in the solution, improve immobilization
The hydrolysis efficiency of acidic ionic liquid, and shorten the time of ultrasound assisted extraction.(3) be prepared for being easily recycled, hydrolysis efficiency it is high
Surface modification has the magnetic ferric oxide nano particles of acidic ionic liquid to be pre-processed in the solution to wheat germ, it is therefore intended that by beam
The aldehydes matter for tiing up state is converted into extractible free state phenols.（4）Although ultrasound can improve aldehydes matter extraction efficiency,
It is certain phenols, such as caffeic acid is easy to degrade during the ultrasonic extraction of higher-energy, therefore the present invention has investigated ultrasound
The condition of phenols is extracted, it is final to determine that ultrasonic power is 48-76 W, ultrasonic time 20-30 min, temperature range 30-40
℃.（5）The present invention is reproducible, and operation is relatively simple, and extraction efficiency is high.
As an embodiment of the present invention：A kind of immobilization acidic ion liquid-ultrasound of wheat embryo phenols extract
Assisted extraction method, includes the following steps：
（1）Microwave deactivating enzyme：Weigh certain quantity of fresh, without rotten wheat embryo, tiling is put into microwave tray, thickness 1-
2 cm.3 min of enzyme deactivation under conditions of 700 W of microwave power, then takes out wheat germ and stands to room temperature；
（2）N-hexane degreasing：It is 1 that 20 g of the wheat germ after enzyme deactivation, which is weighed, according to solid-liquid ratio:5 ratio is mixed with n-hexane, in temperature
Degree is 80 min of degreasing under conditions of 25 DEG C；
（3）Ultramicro grinding：5 min of defatted wheat germ is crushed using micronizer；
（4）Coprecipitation prepares Fe3O4：It is 1.75 to take molar ratio：1 FeSO4·7H2O and FeNO3·9H2O is dissolved in deionized water
In, the ammonium hydroxide of 2 mol/L is added, it is 11 to adjust mixed solution pH, stirs 20 min at 60 DEG C later, it is cotton-shaped to obtain black
Liquid.Mixed solution is moved into 4 h of crystallization in 110 DEG C of autoclaves.After using electromagnet collect magnetic black precipitate,
It is washed with deionized and dries afterwards to get magnetic Fe three times3O4Nano-particle；
（5）Fe3O4@SiO2Preparation：Take 1 g steps（4）Prepared Fe3O4300 ml deionized waters are dissolved in, are ultrasonically treated
10 ml silester are added dropwise after 2 min of solution and stir 5 h at 25 DEG C.Electromagnet collects Fe3O4@SiO2And spend from
Three times, 50 DEG C of 5 h of drying obtain powdered Fe3O4@SiO2 to sub- water washing；
（6）Acidic ionic liquid [MIM] HSO4Synthesis：By 1- methylimidazoles with 1：1 ratio is dissolved in anhydrous acetonitrile, in 0 DEG C of item
Pole is slowly added into the concentrated sulfuric acid and slowly stirs 20 h under part, washs three times and is dried in vacuo 8 h with toluene later, obtain
[MIM]HSO4；
（7）The synthesis of Fe3O4@SiO2- [MIM] HSO4：By 1 ml 3- r-chloropropyl trimethoxyl silanes and 2 g steps（5）Gained
Fe3O4@SiO2 are dissolved in toluene and 36 h that flow back, and 4 mmol [MIM] HSO4 is dissolved in absolute ethyl alcohol later and mixes two kinds of solution
It closes, mixed liquor is ultrasonically treated 0.5 h, and stands 20 h at 65 DEG C and obtain Fe3O4@SiO2- [MIM] HSO4.It is returned from Fig. 1 magnetic hysteresis
Line can be seen that Fe3O4 SiO2- [MIM] HSO4 obtained has superparamagnetism, show under the action of externally-applied magnetic field, be made
Composite material can quickly be separated from solution；
（8）Fe3O4@SiO2-[MIM]HSO4It is free state phenols to convert constraint phenols in wheat germ：By step（7）The surface of preparation
Modify the magnetic ferroferric oxide nano-particles of acidic ionic liquid, i.e. Fe3O4@SiO2-[MIM]HSO4With 1：10 mass ratio
With step（3）Gained defatted wheat germ powder mixes in deionized water, is protected from light stirring 5-15 h.After reaction, using electromagnet
To the magnetic Fe in mixed solution3O4@SiO2-[MIM]HSO4Fully recycled；
（9）The ultrasonic extraction of wheat embryo phenols：To step（8）Isometric absolute ethyl alcohol is added in gained mixed liquor.Mixed solution
Under conditions of 10 DEG C of temperature, it is ultrasonically treated 10 min, ultrasonic power 48W.Ultrasound mode is to be spaced after being ultrasonically treated 10 s
10 s；
（10）Concentration：By step（9）30 min are centrifuged at 5 DEG C of the mixed liquor of gained, gained supernatant depressurizes rotary evaporation, will be dense
Contracting object is freeze-dried to obtain powdered extract, as wheat germ phenols extract；
（11）The quantitative determination of 8 kinds of phenolic acid in extract：Accurately weigh certain mass step（10）It is extract obtained to be dissolved in methanol
And 0.22 μm of filter membrane is crossed, use Syrups by HPLC caffeic acid, chlorogenic acid, ferulic acid, vanillic acid, syringic acid, nutgall
The content of acid, sinapic acid, p-Coumaric Acid.Mobile phase A is acetic acid aqueous solution（1：49, v/v）, Mobile phase B is acetic acid/acetonitrile/water
Solution（2：30：68, v/v）, elution requirement is as follows：0-15 min, B phase 0%；15-30 min, B phases 0-15%；30-40 min, B
Phase 15-25%；40-50 min, B phases 25-50%；50-55 min, B phase 50%；55-60 min, B phases 50-100%；60-70 min,
B phases 100%.The content of each phenolic acid show that data are in table 1 after being compared with standard sample；
（12）The measurement of total phenol content：Accurately weigh certain mass step（10）Gained powdered extract is dissolved in 95% ethanol solution
In, and forint phenol reagent is added and is uniformly mixed, it is protected from light after sodium carbonate liquor mixing is added after standing 5 min and is protected from light standing 40 again
Min records light absorption value and and gallic acid titer control at 760 nm wavelength.The contained milli of every gram of extract of total phenol content
Gram equivalent gallic acid indicates（mg GAE/g DW）.
As an embodiment of the present invention：A kind of immobilization acidic ion liquid-ultrasound of wheat embryo phenols extract
Assisted extraction method, includes the following steps：
（1）Microwave deactivating enzyme：Certain quantity of fresh wheat embryo is weighed, tiling is put into microwave tray, thickness 1-2 cm.Micro-
2.5 min of enzyme deactivation under conditions of 800 W of wave power, then takes out wheat germ and stands to room temperature；
（2）N-hexane degreasing：It is 1 that 10 g of the wheat germ after enzyme deactivation, which is weighed, according to solid-liquid ratio:5 ratio is mixed with n-hexane, in temperature
Degree is 70 min of degreasing under conditions of 15 DEG C；
（3）Ultramicro grinding：6 min of defatted wheat germ is crushed using micronizer；
（4）Coprecipitation prepares Fe3O4：It is 1.8 to take molar ratio：1 FeSO4·7H2O and FeNO3·9H2O is dissolved in deionized water
In, the ammonium hydroxide of 3 mol/L is added, it is 12 to adjust mixed solution pH, stirs 10 min at 30 DEG C later, it is cotton-shaped to obtain black
Liquid.Mixed solution is moved into 2 h of crystallization in 120 DEG C of autoclaves.After using electromagnet collect magnetic black precipitate,
It is washed with deionized and dries afterwards to get magnetic Fe three times3O44Nano-particle；
（5）Fe3O4@SiO2Preparation：Take 1 g steps（4）Prepared Fe3O4300 ml deionized waters are dissolved in, are ultrasonically treated
10 ml silester are added dropwise after 2 min of solution and stir 6 h at 25 DEG C.Electromagnet collects Fe3O4@SiO24And it spends
Three times, 50 DEG C of 4 h of drying obtain powdered Fe to ion water washing3O4@SiO24；
（6）Acidic ionic liquid [MIM] HSO4Synthesis：By 1- methylimidazoles with 1：1 ratio is dissolved in anhydrous acetonitrile, in 0 DEG C of item
Pole is slowly added into the concentrated sulfuric acid and slowly stirs 18 h under part, washs three times and is dried in vacuo 8 h with toluene later, obtain
[MIM]HSO4；
（7）Fe3O4@SiO2-[MIM]HSO4Synthesis：By 1 ml 3- r-chloropropyl trimethoxyl silanes and 2 g steps（5）Gained
Fe3O4@SiO24Toluene is dissolved in and 32 h that flow back, later by 4 mmol [MIM] HSO4It is dissolved in absolute ethyl alcohol and mixes two kinds of solution
It closes, mixed liquor is ultrasonically treated 0.2 h, and stands 20 h at 60 DEG C and obtain Fe3O4@SiO2-[MIM]HSO4.It is returned from Fig. 2 magnetic hysteresis
Line can be seen that Fe obtained3O4@SiO2-[MIM]HSO4With superparamagnetism, show under the action of externally-applied magnetic field, it is obtained
Composite material can be separated quickly from solution；
（8）Fe3O4@SiO2-[MIM]HSO4It is free state phenols to convert constraint phenols in wheat germ：By step（7）The surface of preparation
The magnetic ferroferric oxide nano-particles of acidic ionic liquid are modified, i.e., Fe3O4@SiO2- [MIM] HSO4 is with 1：10 mass ratio
With step（3）Gained defatted wheat germ powder mixes in deionized water, is protected from light stirring 5-15 h.After reaction, using electromagnet
To the magnetic Fe in mixed solution3O4@SiO2-[MIM]HSO4Fully recycled；
（9）The ultrasonic extraction of wheat embryo phenols：To step（8）Isometric absolute ethyl alcohol is added in gained mixed liquor.Mixed solution
Under conditions of 10 DEG C of temperature, it is ultrasonically treated 10 min, ultrasonic power 48W.Ultrasound mode is to be spaced after being ultrasonically treated 10 s
10 s；
（10）Concentration：By step（9）10-30 min are centrifuged at 5 DEG C of the mixed liquor of gained, gained supernatant depressurizes rotary evaporation,
Concentrate is freeze-dried to obtain powdered extract, as wheat germ phenols extract；
（11）The quantitative determination of 8 kinds of phenolic acid in extract：Accurately weigh certain mass step（10）It is extract obtained to be dissolved in methanol
And 0.22 μm of filter membrane is crossed, use Syrups by HPLC caffeic acid, chlorogenic acid, ferulic acid, vanillic acid, syringic acid, nutgall
The content of acid, sinapic acid, p-Coumaric Acid.Mobile phase A is acetic acid aqueous solution（1：49, v/v）, Mobile phase B is acetic acid/acetonitrile/water
Solution（2：30：68, v/v）, elution requirement is as follows：0-15 min, B phase 0%；15-30 min, B phases 0-15%；30-40 min, B
Phase 15-25%；40-50 min, B phases 25-50%；50-55 min, B phase 50%；55-60 min, B phases 50-100%；60-70 min,
B phases 100%.The content of each phenolic acid show that data see attached list 1 after being compared with standard sample；
（12）The measurement of total phenol content：Accurately weigh certain mass step（10）Gained powdered extract is dissolved in 95% ethanol solution
In, and forint phenol reagent is added and is uniformly mixed, it is protected from light after sodium carbonate liquor mixing is added after standing 5 min and is protected from light standing 40 again
Min records light absorption value and and gallic acid titer control at 760 nm wavelength.The contained milli of every gram of extract of total phenol content
Gram equivalent gallic acid indicates（mg GAE/g DW）, data are shown in Table 1.
As an embodiment of the present invention：A kind of immobilization acidic ion liquid-ultrasound of wheat embryo phenols extract
Assisted extraction method, includes the following steps：
（1）Microwave deactivating enzyme：Certain quantity of fresh wheat embryo is weighed, tiling is put into microwave tray, thickness 1-2 cm.Micro-
2 min of enzyme deactivation under conditions of 1000 W of wave power, then takes out wheat germ and stands to room temperature；
（2）N-hexane degreasing：It is 1 that 10 g of the wheat germ after enzyme deactivation, which is weighed, according to solid-liquid ratio:10 ratio is mixed with n-hexane, in temperature
Degree is 60 min of degreasing under conditions of 15 DEG C；
（3）Ultramicro grinding：6 min of defatted wheat germ is crushed using micronizer；
（4）Coprecipitation prepares Fe3O4：It is 2 to take molar ratio：1 FeSO4·7H2O and FeNO3·9H2O is dissolved in deionized water,
The ammonium hydroxide of 3 mol/L is added, it is 13 to adjust mixed solution pH, stirs 5 min at 30 DEG C later, obtains the cotton-shaped liquid of black
Body.Mixed solution is moved into 2 h of crystallization in 110 DEG C of autoclaves.After using electromagnet collect magnetic black precipitate, use
Deionized water washing is dried to get magnetic Fe afterwards three times3O4Nano-particle；
（5）Fe3O4@SiO2Preparation：Take 1 g steps（4）Prepared Fe3O4300 ml deionized waters are dissolved in, are ultrasonically treated
10 ml silester are added dropwise after 1 min of solution and stir 8 h at 25 DEG C.Electromagnet is collected Fe3O4@SiO2 and is spent
Three times, 50 DEG C of 5 h of drying obtain powdered Fe to ion water washing3O4@SiO2；
（6）Acidic ionic liquid [MIM] HSO4Synthesis：By 1- methylimidazoles with 1：1 ratio is dissolved in anhydrous acetonitrile, in 0 DEG C of item
Pole is slowly added into the concentrated sulfuric acid and slowly stirs 16 h under part, washs three times and is dried in vacuo 10 h with toluene later, obtain
[MIM]HSO4；
（7）Fe3O4@SiO2-[MIM]HSO4Synthesis：By 1 ml 3- r-chloropropyl trimethoxyl silanes and 2 g steps（5）Gained
Fe3O4@SiO2 are dissolved in toluene and 30 h that flow back, later by 4 mmol [MIM] HSO4It is dissolved in absolute ethyl alcohol and mixes two kinds of solution
It closes, mixed liquor is ultrasonically treated 30 min, and stands 20 h at 60 DEG C and obtain Fe3O4@SiO2-[MIM]HSO4.It is returned from Fig. 3 magnetic hysteresis
Line can be seen that Fe obtained3O4@SiO2-[MIM]HSO4With superparamagnetism, show under the action of externally-applied magnetic field, it is obtained
Composite material Fe3O4@SiO2-[MIM]HSO4It can quickly be separated from solution；
（8）Fe3O4@SiO2-[MIM]HSO4It is free state phenols to convert constraint phenols in wheat germ：By step（7）The surface of preparation
Modify the magnetic ferroferric oxide nano-particles of acidic ionic liquid, i.e. Fe3O4@SiO2-[MIM]HSO4With 1：5 mass ratio with
Step（3）Gained defatted wheat germ powder mixes in deionized water, is protected from light 6 h of stirring.After reaction, using electromagnet to mixing
Magnetic Fe in solution3O4@SiO2-[MIM]HSO4It is recycled；
（9）The ultrasonic extraction of wheat embryo phenols：To step（8）Isometric absolute ethyl alcohol is added in gained wheat germ solution.Mixing
Solution is ultrasonically treated 15 min under conditions of 8 DEG C of temperature, and ultrasonic power is 76 W.Ultrasound mode is after being ultrasonically treated 10 s
It is spaced 10 s；
（10）Concentration：By step（9）25 min are centrifuged at 5 DEG C of the mixed liquor of gained, gained supernatant depressurizes rotary evaporation, will be dense
Contracting object is freeze-dried to obtain powdered extract, as wheat germ phenols extract；
（11）The quantitative determination of 8 kinds of phenolic acid in extract：Accurately weigh certain mass step（10）It is extract obtained to be dissolved in methanol
And 0.22 μm of filter membrane is crossed, use Syrups by HPLC caffeic acid, chlorogenic acid, ferulic acid, vanillic acid, syringic acid, nutgall
The content of acid, sinapic acid, p-Coumaric Acid.Mobile phase A is acetic acid aqueous solution（1：49, v/v）, Mobile phase B is acetic acid/acetonitrile/water
Solution（2：30：68, v/v）, elution requirement is as follows：0-15 min, B phase 0%；15-30 min, B phases 0-15%；30-40 min, B
Phase 15-25%；40-50 min, B phases 25-50%；50-55 min, B phase 50%；55-60 min, B phases 50-100%；60-70 min,
B phases 100%.The content of each phenolic acid show that data are shown in Table 1 after being compared with standard sample；
（12）The measurement of total phenol content：Accurately weigh certain mass step（10）Gained powdered extract is dissolved in 95% ethanol solution
In, and forint phenol reagent is added and is uniformly mixed, it is protected from light after sodium carbonate liquor mixing is added after standing 5 min and is protected from light standing 40 again
Min records light absorption value and and gallic acid titer control at 760 nm wavelength.The contained milli of every gram of extract of total phenol content
Gram equivalent gallic acid indicates（mg GAE/g DW）, data are shown in Table 1：
Table 1 is material composition table.
The above shows and describes the basic principles and main features of the present invention and the advantages of the present invention, for this field skill
For art personnel, it is clear that invention is not limited to the details of the above exemplary embodiments, and without departing substantially from the present invention spirit or
In the case of essential characteristic, the present invention can be realized in other specific forms.Therefore, in all respects, should all incite somebody to action
Embodiment regards exemplary as, and is non-limiting, the scope of the present invention by appended claims rather than on state
Bright restriction, it is intended that including all changes that come within the meaning and range of equivalency of the claims in the present invention
It is interior.
In addition, it should be understood that although this specification is described in terms of embodiments, but not each embodiment is only wrapped
Containing an independent technical solution, this description of the specification is merely for the sake of clarity, and those skilled in the art should
It considers the specification as a whole, the technical solutions in the various embodiments may also be suitably combined, forms those skilled in the art
The other embodiment being appreciated that.
Claims (10)
1. a kind of immobilization acidic ion liquid extraction method of wheat embryo phenols extract, it is characterised in that：Include the following steps：
Step 1, enzyme deactivation：Fresh, the mildew and rot rotten wheat embryo of nothing is selected, is laid on microwave tray, at microwave
1-5 min are managed, microwave power is 550-1000 W；
Step 2, degreasing：Defatted wheat germ is obtained using n-hexane pressuring method, defatted wheat germ dries rear ultramicro grinding and obtains degreasing
Wheat germ powder；
Step 3, using Fe3O4@SiO2-[MIM]HSO4Converting constraint phenols in wheat germ becomes free state phenols：By the surface of preparation
Modify the magnetic ferroferric oxide nano-particles of acidic ionic liquid, i.e. Fe3O4@SiO2-[MIM]HSO4With certain mass ratio with
Defatted wheat germ powder after crushing mixes in deionized water, is protected from light stirring 5-15 h, after reaction, using electromagnet to mixing
Magnetic Fe in solution3O4@SiO2-[MIM]HSO4It is recycled；
Step 4, the ultrasonic extraction of wheat embryo phenols：Isometric absolute ethyl alcohol is poured into the wheat germ solution obtained to step 3,
Mixed solution is under conditions of 10-40 DEG C of temperature, ultrasonic extraction 5-30 min, and ultrasonic power is 48-76 W, and ultrasound mode is
It is spaced 10 s after being ultrasonically treated 10 s；
Step 5, dehydration concentration：By the mixed liquor low-temperature centrifugation 10-30 min obtained by above-mentioned steps, the decompression rotation of gained supernatant
Evaporation, concentrate is freeze-dried to obtain powdered extract, as wheat germ phenols extract.
2. a kind of immobilization acidic ion liquid extraction method of wheat embryo phenols extract according to claim 1, special
Sign is：In step 2, the mass ratio of defatted wheat germ and n-hexane is 1:4-1：15, degreasing time is 30-120 min, degreasing temperature
Degree is 5-30 DEG C.
3. a kind of immobilization acidic ion liquid extraction method of wheat embryo phenols extract according to claim 1, special
Sign is：In step 2, the time of defatted wheat germ ultramicro grinding is 5-20 min.
4. a kind of immobilization acidic ion liquid extraction method of wheat embryo phenols extract according to claim 1, special
Sign is：In step 3, the preparations of magnetic ferric oxide nano particles uses coprecipitation, i.e., to containing divalent and ferric ion
Mole be 1.75-2:Alkaline solution is added in 1 salting liquid, adjusts pH within the scope of 11-13, it is cotton-shaped to be stirred continuously generation black
Object, the crystallization 1-5 h under 100-140 DEG C of temperature condition, generate black magnetic iron oxide nano-particle precipitation, use electromagnetism later
Iron adsorption of nanoparticles is simultaneously washed with deionized water repeatedly, and magnetic ferric oxide nano particles are obtained after low temperature drying.
5. a kind of immobilization acidic ion liquid extraction method of wheat embryo phenols extract according to claim 1, special
Sign is：In step 3, acidic ionic liquid [MIM] HSO4Preparation process be：1- methylimidazoles are dissolved in anhydrous acetonitrile ,-
It is slowly added to the concentrated sulfuric acid under the conditions of 10 to 0 DEG C and slowly stirs, fully washed three times with toluene after reaction and is dried in vacuo 2-8
H obtains [MIM] HSO4。
6. a kind of immobilization acidic ion liquid extraction method of wheat embryo phenols extract according to claim 1, special
Sign is：In step 3, Fe3O4@SiO2Synthesis mode be：By Fe3O4Be dissolved in deionized water, be ultrasonically treated after mixed solution by
It is added dropwise to silester and stirs 5-10 h at 30 DEG C, electromagnet is collected product and washed for several times, is obtained after dry powdered
Fe3O4@SiO2。
7. a kind of immobilization acidic ion liquid extraction method of wheat embryo phenols extract according to claim 1, special
Sign is：In step 3, Fe3O4@SiO2-[MIM]HSO4Preparation process be：By 3- r-chloropropyl trimethoxyl silanes and Fe3O4@
SiO2Toluene is dissolved in and 36 h that flow back, later by acidic ionic liquid obtained [MIM] HSO4It is dissolved in absolute ethyl alcohol and by two kinds of solution
Mixing, mixed liquor are ultrasonically treated 20-60 min, and stand 15-25 h at 40-65 DEG C and obtain Fe3O4@SiO2-[MIM]HSO4。
8. a kind of immobilization acidic ion liquid extraction method of wheat embryo phenols extract according to claim 1, special
Sign is：In step 3, Fe3O4@SiO2-[MIM]HSO4Mass ratio with defatted wheat germ powder is 1：5-1：50.
9. a kind of immobilization acidic ion liquid extraction method of wheat embryo phenols extract according to claim 1, special
Sign is：In step 4, during ultrasonic extraction, solution temperature is 40-60 DEG C, and sonication treatment time is 40-240 min.
10. a kind of immobilization acidic ion liquid extraction method of wheat embryo phenols extract according to claim 1, special
Sign is：Low-temperature centrifugation rotating speed described in step 5 is 4000-12000 r/min, and temperature is 4-10 DEG C, the rotary evaporation
Time is 5-20 h, and temperature is 50-60 DEG C.
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