CN109369705A - The method for extracting hydriopsis cumingii plasmalogen using titanium-based mesoporous silica gel composite material - Google Patents
The method for extracting hydriopsis cumingii plasmalogen using titanium-based mesoporous silica gel composite material Download PDFInfo
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- CN109369705A CN109369705A CN201811187118.4A CN201811187118A CN109369705A CN 109369705 A CN109369705 A CN 109369705A CN 201811187118 A CN201811187118 A CN 201811187118A CN 109369705 A CN109369705 A CN 109369705A
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- plasmalogen
- mesoporous silica
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 45
- 239000000741 silica gel Substances 0.000 title claims abstract description 45
- 229910002027 silica gel Inorganic materials 0.000 title claims abstract description 45
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 229910052719 titanium Inorganic materials 0.000 title claims abstract description 36
- 239000010936 titanium Substances 0.000 title claims abstract description 36
- 239000002131 composite material Substances 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 48
- 239000000843 powder Substances 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- 150000002632 lipids Chemical class 0.000 claims abstract description 9
- 239000000376 reactant Substances 0.000 claims abstract description 8
- 239000000287 crude extract Substances 0.000 claims abstract description 7
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 20
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 16
- 239000000284 extract Substances 0.000 claims description 14
- 235000019441 ethanol Nutrition 0.000 claims description 13
- 239000004202 carbamide Substances 0.000 claims description 11
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 10
- 239000013505 freshwater Substances 0.000 claims description 10
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 9
- 241000237536 Mytilus edulis Species 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 235000020638 mussel Nutrition 0.000 claims description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 8
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 8
- 235000019253 formic acid Nutrition 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 230000009514 concussion Effects 0.000 claims description 7
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 238000001354 calcination Methods 0.000 claims description 6
- 239000012065 filter cake Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 5
- 238000010828 elution Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000004090 dissolution Methods 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 3
- 210000004907 gland Anatomy 0.000 claims description 3
- 238000001027 hydrothermal synthesis Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical group [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 239000003292 glue Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 abstract description 4
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 230000000052 comparative effect Effects 0.000 description 7
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 210000002569 neuron Anatomy 0.000 description 4
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 description 3
- 206010013786 Dry skin Diseases 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011799 hole material Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
- 241000237519 Bivalvia Species 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- 241000382840 Hyriopsis cumingii Species 0.000 description 1
- 241000238370 Sepia Species 0.000 description 1
- 241000217379 Unionidae Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- -1 acyl inositol Chemical compound 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229940009944 amidoline Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 210000004958 brain cell Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000002366 mineral element Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- BZQFBWGGLXLEPQ-REOHCLBHSA-N phosphoserine Chemical compound OC(=O)[C@@H](N)COP(O)(O)=O BZQFBWGGLXLEPQ-REOHCLBHSA-N 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000020995 raw meat Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 241000894007 species Species 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
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/103—Extraction or purification by physical or chemical treatment of natural phosphatides; Preparation of compositions containing phosphatides of unknown structure
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
- B01J20/103—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate comprising silica
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28054—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
- B01J20/28078—Pore diameter
- B01J20/28083—Pore diameter being in the range 2-50 nm, i.e. mesopores
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Inorganic Chemistry (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
The invention discloses a kind of methods for extracting hydriopsis cumingii plasmalogen using titanium-based mesoporous silica gel composite material, comprising the following steps: hydriopsis cumingii powder A1 is carried out thick rouge extraction;Resulting lipid crude extract B1 is subjected to alkaline reaction, obtains alkaline reactant C1;Prepare titanium-based mesoporous silica gel composite material;Titanium-based mesoporous silica gel composite material is filled in chromatographic column, alkaline reactant C1 is added in chromatographic column, elutes chromatographic column using organic solvent, leacheate is collected, obtains plasmalogen after dry.Extracting method of the invention has plasmalogen yield height, good product purity, using waste resource, conducive to the feature of environmental protection.
Description
Technical field
The present invention relates to hydriopsis cumingii plasmalogen extracting methods, especially a kind of to utilize titanium-based mesoporous silica gel composite material
The method for extracting hydriopsis cumingii plasmalogen.
Background technique
Hydriopsis cumingii (Hyriopsis cumingii Lea) is commonly called as freshwater mussel, pearl freshwater mussel, triangle freshwater mussel, Non-marine Bivalvess software
Animal belongs to Bivalvia, Unionidae, sail freshwater mussel category.Its shell is big and flat, shell surface black or sepia, thick and hard, nearly 20 centimetres long,
Back edge stretches out a sail rear wing upwards afterwards, makes freshwater mussel shape in triangular shape.Hydriopsis cumingii is the distinctive species in China, there is important economy
Value, in fresh water pearl culturing clam the pearl thickness of produced pearl, gloss is strong, quality is splendid.The meat of hydriopsis cumingii is slightly tough, native raw meat
It is highly seasoned to be difficult to eat, it is often abandoned as waste or for feed processing, economic value added is low.Then its is rich in
Protein, lipid, vitamin and inorganic mineral element etc. have preferable processing and utilization space.
Plasmalogen (plasmalogen) is a kind of phosphatide of ether-containing, it is characterized in that ehter bond and sn-2 in the position sn-1
The ester bond of position, wherein the position sn-1 is usually connected to C16:0;The fatty alcohol of C18:0 or C18:1, the position sn-2 multi-connection
Polyunsaturated fatty acids (PUFAs), head multi-connection ethyl alcohol amido or choline base.The study found that the muscle of shellfish and interior
Contain plasmalogen in dirty.Since sn-1 there are the special construction of alkene ehter bond, plasmalogen has compared to common phosphatide
More more fully Physiology and biochemistry is active.With the continuous development of molecular biology, in the pathogenesis to various human diseases
In research with phosphatide group, the various bioactivity of plasmalogen are also constantly found and confirm.Some researches show that acetal phosphorus
Rouge shows a variety of different physiological functions, the generation of plasmalogen in the metabolic process as a kind of special phospholipid molecule
Thank to exception, it will cause a series of disease.Half a century, plasmalogen are constantly proved to have with alzheimer's disease straight
Connect connection.By a large amount of it is demonstrated experimentally that plasmalogen can be with: making that nerve cell is newborn, neuron is prominent, nerve cell is strengthened
Effect, protection brain cell, anti-oxidant, prevention nerve cell apoptosis reduce neuroinflamation, the accumulation of metabolism amyloid beta, are promoted
Memory and study idea improve alzheimer's disease.
Therefore, the plasmalogen in hydriopsis cumingii is studied, to research and development newtype drug and health functional food, improves spinnaker
Freshwater mussel added value is of great significance.
Summary of the invention
Hydriopsis cumingii is extracted using titanium-based mesoporous silica gel composite material the technical problem to be solved in the present invention is to provide a kind of
The method of plasmalogen;Extracting method of the invention has that plasmalogen yield is high, good product purity (91.6%), using discarded
Resource, conducive to environmental protection feature.
Spinnaker is extracted using titanium-based mesoporous silica gel composite material in order to solve the above technical problem, the present invention provides a kind of
The method of freshwater mussel plasmalogen, comprising the following steps:
A, hydriopsis cumingii pre-processes:
It is made rotten shape (using cutmixer) after cleaning decladding, removal capsule gland by hydriopsis cumingii, musculature is taken to clean, it is dry
After powder processed, obtain hydriopsis cumingii powder A1;
B, thick rouge extracts:
It is sufficiently mixed uniformly after organic solvent I is added in hydriopsis cumingii powder A1, stirring (200 ± 40rpm) extraction 2 ±
0.5h;
Then water is added, concussion (acutely concussion) is centrifuged (is centrifuged 20min with 9000rpm) afterwards, removes clear liquid (to solution point
Layer, which moves back, removes clear liquid);Lower clear liquid is dry (being dried under reduced pressure), obtain lipid crude extract B1;
Cold acetone (acetone that pre-cooling is 0 DEG C) is added into lipid crude extract B1, gained is precipitated as phosphatide runic object B2;
Remarks: phosphatide does not dissolve in acetone, and acetone temperature is lower, and phosphatide solubility is poorer;Therefore phosphorus after addition cold acetone
Rouge is precipitated;
C, alkaline reaction:
Organic solvent II is added to the resulting phosphatide runic object B2 of step B, makes phosphatide runic object B2 dissolution (sufficiently dissolution),
The organic solvent II I containing alkaline matter is then added, reacts at room temperature 30 ± 10min;
Extract liquor IV is added in reaction gains, shakes (acutely concussion) centrifugation (20min is centrifuged with 9000rpm) afterwards,
Lower clear liquid is dry (being dried under reduced pressure), it is then redissolved using organic solvent II, obtains alkaline reactant C1;
D, titanium-based mesoporous silica gel composite material is prepared:
Bromide sixteen alkyls pyridine, urea are taken respectively, are uniformly mixed after water is added, it is mixed to continuously add hexamethylene, isopropanol
It closes uniform;(time for adding is 4~6 minutes) tetraethyl orthosilicate is added dropwise in (200 ± 40rpm) under agitation, is mixed
Object D1;Bromide sixteen alkyls pyridine: urea: water: hexamethylene: isopropanol: tetraethyl orthosilicate=6g:3g:130~170mL:
130~170mL:4~6mL:14~16mL amount ratio (the preferably amount ratio of 6g:3g:150mL:150mL:5mL:15mL);
By (about 70 DEG C) 24 ± 2h of reaction of the reflux of mixture D 1;It filters after reaction, gained filter cake first uses ethyl alcohol, Shui Run
It washes, drying is placed on 500 ± 50 DEG C of 4 ± 0.5h of calcining of Muffle furnace, obtains mesoporous silica gel D2;
Four tert-butyl ester of metatitanic acid is added into ethyl alcohol, 60 ± 10 DEG C are heated to after mixing, adds and is given an account of under heat-retaining condition
It is uniformly mixed, stirred to dry (ethyl alcohol is volatilized) after the silica gel D2 of hole, is then allowed to stand in 100 ± 10 DEG C of 12 ± 2h of reaction, obtained anti-
Answer product D3;The mesoporous silica gel D2: ethyl alcohol: four tert-butyl ester=7.5 of metatitanic acid~8.5g:120~160mL:33~37g dosage
Than (the preferably amount ratio of 8g:140mL:35g);
Reaction product D3 is added into hydrothermal reaction kettle and water filters after reaction in 60 ± 10 DEG C of 6 ± 1h of reaction,
Gained filter cake is placed in 500 ± 50 DEG C of 5 ± 0.5h of calcining of Muffle furnace, obtains titanium-based mesoporous silica gel composite material;The reaction product
D3: water=1g/20 ± 5mL;
E, plasmalogen isolates and purifies:
Titanium-based mesoporous silica gel composite material is filled in chromatographic column (chromatographic column of 30mm × 300mm), step C is resulting
Alkaline reactant C1 is added in chromatographic column, first elutes 10 ± 2min of chromatographic column using organic solvent V, reuses organic solvent VI leaching
30 ± 5min of chromatographic column is washed, the corresponding leacheate of organic solvent VI is collected, obtains plasmalogen after dry (being dried under reduced pressure);
The organic solvent V is acetonitrile: water: formic acid: the mixing of ammonium formate=950mL:50mL:1mL:125mg amount ratio
It forms;The organic solvent VI be acetonitrile: water: formic acid: ammonium formate=700mL:300mL:1mL:750mg amount ratio mixing and
At;The flow velocity of the elution is 5mL/min.
Remarks: when the amount of the hydriopsis cumingii powder A1 of step B is 10g, the titanium-based mesoporous silica gel composite material of adapted is 50 ±
10g。
As it is of the invention using titanium-based mesoporous silica gel composite material extract hydriopsis cumingii plasmalogen method improvement,
In the step B:
Organic solvent I is 1,2 dichloroethanes: methanol=1:2 volume ratio mixed liquor, hydriopsis cumingii powder A1 and organic solvent
I solid-liquid ratio is 1g/25 ± 5mL;The dosage of the water is 0.6 ± 0.1 volume times of organic solvent I;The cold acetone temperature
It is 0 DEG C, dosage is 0.2 ± 0.05 volume times of organic solvent I.
As the method for the invention for extracting hydriopsis cumingii plasmalogen using titanium-based mesoporous silica gel composite material into one
Step is improved, in the step C:
Organic solvent II is 1,2 dichloroethanes: methanol=1:1 volume ratio mixed liquor, triangle when dissolution, in step B
Sail freshwater mussel powder A1 and the solid-liquid ratio of organic solvent II are 1g/30 ± 5mL;
Organic solvent II I containing alkaline matter is sodium hydroxide methanol aqueous solution, wherein sodium hydroxide: methanol: water=
The solid-liquid ratio of hydriopsis cumingii powder A1 in 14g:960mL:40mL, the step B and organic solvent II I containing alkaline matter is 1g/5
±1mL;
Extract liquor IV is 1,2 dichloroethanes: water=5:3 volume ratio mixed liquor, hydriopsis cumingii powder A1 and extraction in step B
The solid-liquid ratio for taking liquid IV is 1g/50 ± 5mL;
When redissolution, the solid-liquid ratio of the hydriopsis cumingii powder A1 in step B and organic solvent II is 1g/1 ± 0.1mL.
The present invention passes through lipid coarse extraction, alkaline reaction, titanium-based mesoporous silica gel composite material point using hydriopsis cumingii as raw material
From etc. a series of technological means, prepare the plasmalogen of high-content.Wherein alkaline reaction can effectively decompose phosphatide ester bond, retain tool
There is the plasmalogen of alkene ehter bond.Titanium-based in titanium-based mesoporous silica gel composite material has preferable selection to the phosphate group of phosphatide
Property, while mesoporous silica gel has bigger surface area than common silica gel, so that the load capacity of titanium-based is significantly improved, so that titanium-based is situated between
Hole material silica gel composite has significant separating effect to plasmalogen, and plasmalogen purity can achieve 91.6%, recovery rate
High (plasmalogen 98mg (in terms of 10g hydriopsis cumingii powder A1)).Utilization titanium-based mesoporous silica gel composite material in the present invention extracts
The method of hydriopsis cumingii plasmalogen has superior product quality, added value of product height, using waste resource, conducive to the spy of environmental protection
Point.The present invention provides the methods for extracting hydriopsis cumingii plasmalogen using titanium-based mesoporous silica gel composite material.
Detailed description of the invention
Specific embodiments of the present invention will be described in further detail with reference to the accompanying drawing.
Fig. 1 is the LC Mass of the titanium-based mesoporous silica gel composite material separation resulting plasmalogen of hydriopsis cumingii
Qualification figure.
Specific embodiment
The present invention is described further combined with specific embodiments below, but protection scope of the present invention is not limited in
This:
Acutely concussion is 150~300rpm.
Embodiment 1, it is a kind of using titanium-based mesoporous silica gel composite material extract hydriopsis cumingii plasmalogen method, successively into
Row following steps:
A, hydriopsis cumingii pre-processes:
1kg hydriopsis cumingii is cleaned into decladding, removal capsule gland, takes musculature clean and then gruel is made using cutmixer
Shape is crushed to the sieve that can cross 60 mesh, obtains hydriopsis cumingii powder A1 after 80 DEG C of dryings to moisture content≤0.5% (weight %).
B, thick rouge extracts:
It takes hydriopsis cumingii powder A1 10g and 1,2- dichloroethanes/methyl alcohol mixed liquor (1,2 2 chloroethenes of 250mL is added to it
Alkane: methanol=1:2, v/v) after be sufficiently mixed uniformly, with 200rpm stir extract 2h, then be added 150mL water, acutely shake 10
20min is centrifuged with 9000rpm after minute, is moved back to solution layering and removes clear liquid;Lower clear liquid is dried under reduced pressure (0.08Mpa, 60 DEG C
Dry to constant weight), obtain lipid crude extract B1;
Acetone (as solvent) 50mL that pre-cooling is 0 DEG C is added to lipid crude extract B1, the precipitating of precipitation is that phosphatide is thick
Body object B2.
C, alkaline reaction:
Organic solvent II 300mL is added into the resulting whole phosphatide runic object B2 of step B to sufficiently dissolve phosphatide
Runic object B2 is then added the organic solvent II I that 50mL contains alkaline matter, reacts at room temperature 30min;
500mL extract liquor IV is continuously added in reaction gains, acutely concussion is centrifuged after ten minutes with 9000rpm
Lower clear liquid is dried under reduced pressure (0.08Mpa, 60 DEG C of dryings to constant weight) by 20min, after being redissolved using 10mL organic solvent II, is obtained
Alkaline reactant C1 (C1 product).
Organic solvent II is 1,2 dichloroethanes: methanol=1:1 volume ratio mixed liquor,
Organic solvent II I containing alkaline matter is sodium hydroxide: methanol: water=14g:960mL:40mL amount ratio is matched
Sodium hydroxide methanol aqueous solution obtained by system.
Extract liquor IV is 1,2 dichloroethanes: water=5:3 volume ratio mixed liquor.
D, titanium-based mesoporous silica gel composite material is prepared:
Bromide sixteen alkyls pyridine 6g, urea 3g are taken respectively, are uniformly mixed after 150mL pure water is added, are continuously added 150mL
Hexamethylene, 5mL isopropanol are uniformly mixed;(time for adding is 5 minutes) positive silicon of 15mL is added dropwise under 200rpm stirring condition
Sour tetra-ethyl ester obtains mixture D 1;
For 24 hours in (about 70 DEG C) of reflux reactions by mixture D 1;Filter after reaction, gained filter cake first use ethyl alcohol 50ml,
Water 50ml rinse is placed in 500 DEG C of calcining 4h of Muffle furnace after (that is, after no longer dripping) dry, obtains mesoporous silica gel D2;
Four tert-butyl ester of 35g metatitanic acid is added into 140mL ethyl alcohol, 60 DEG C are heated to after mixing, is continuously added under heat-retaining condition
It is uniformly mixed after 8g mesoporous silica gel D2, insulated and stirred to dry (that is, stirring is volatilized to ethyl alcohol, mixing time is about 10 minutes),
It is then allowed to stand in 100 DEG C of reaction 12h, obtains reaction product D3;
10g reaction product D3 is added into hydrothermal reaction kettle and 200mL water filters after reaction in 60 DEG C of reaction 6h,
Gained filter cake is placed in 500 DEG C of calcining 5h of Muffle furnace, obtains titanium-based mesoporous silica gel composite material.
E, plasmalogen isolates and purifies:
Titanium-based mesoporous silica gel composite material 50g is filled in the chromatographic column of 30mm × 300mm, by the resulting alkalinity of step C
Reactant C1 is added to chromatographic column, then elutes chromatographic column 10min using organic solvent V, reuses organic solvent VI elution
Chromatographic column 30min collects the corresponding leacheate of organic solvent VI, and (0.08Mpa, 60 DEG C of dryings to constant weight) obtain after being dried under reduced pressure
Plasmalogen 98mg (in terms of 10g hydriopsis cumingii powder A1);Being detected plasmalogen purity can achieve 91.6%.
The organic solvent V is acetonitrile: water: formic acid: the mixing of ammonium formate=950mL:50mL:1mL:125mg amount ratio
It forms;The organic solvent VI be acetonitrile: water: formic acid: ammonium formate=700mL:300mL:1mL:750mg amount ratio mixing and
At;The flow velocity when elution is 5mL/min.
Step E isolated plasmalogen passes through LC Mass, and its master is identified after comparing with standard items
Wanting ingredient is phosphatidalcholine, plasmalogen acyl inositol, phosphatidalserine, phosphatidalcholine.Acetal phosphorus
The chromatogram of rouge is as shown in Figure 1.
" titanium-based mesoporous silica gel composite material " in 1 step E of embodiment is changed to " C18 " by comparative example 1, and dosage is constant;Its
It is remaining to be equal to embodiment 1.
Acquired results are as follows: plasmalogen purity is 70%, extracted amount 32mg (in terms of 10g hydriopsis cumingii powder A1).
Comparative example 2-1, by the bromohexadecane base pyrrole in 1 step D of embodiment " preparation titanium-based mesoporous silica gel composite material "
Pyridine: urea: water: hexamethylene: isopropanol: tetraethyl orthosilicate=6g:3g:150mL:150mL:5mL:15mL amount ratio is changed to
Bromide sixteen alkyls pyridine: urea: water: hexamethylene: isopropanol: tetraethyl orthosilicate=7g:2g:150mL:150mL:5mL:
The amount ratio of 15mL;Remaining is equal to embodiment 1.
Acquired results are as follows: plasmalogen purity is 62%, extracted amount 27mg (in terms of 10g hydriopsis cumingii powder A1).
Comparative example 2-2, by the bromohexadecane base pyrrole in 1 step D of embodiment " preparation titanium-based mesoporous silica gel composite material "
Pyridine: urea: water: hexamethylene: isopropanol: tetraethyl orthosilicate=6g:3g:150mL:150mL:5mL:15mL amount ratio is changed to
Bromide sixteen alkyls pyridine: urea: water: hexamethylene: isopropanol: tetraethyl orthosilicate=5g:4g:150mL:150mL:5mL:
The amount ratio of 15mL;Remaining is equal to embodiment 1.
Acquired results are as follows: plasmalogen purity is 51%, extracted amount 30mg (in terms of 10g hydriopsis cumingii powder A1).
Comparative example 2-3, by the bromohexadecane base pyrrole in 1 step D of embodiment " preparation titanium-based mesoporous silica gel composite material "
Pyridine: urea: water: hexamethylene: isopropanol: tetraethyl orthosilicate=6g:3g:150mL:150mL:5mL:15mL amount ratio is changed to
Bromide sixteen alkyls pyridine: urea: water: hexamethylene: isopropanol: tetraethyl orthosilicate=6g:3g:100mL:100mL:6mL:
The amount ratio of 12mL;Remaining is equal to embodiment 1.
Acquired results are as follows: plasmalogen purity is 80.2%, extracted amount 70mg (in terms of 10g hydriopsis cumingii powder A1).
" being statically placed in 100 DEG C of reaction 12h " in 1 step D of embodiment is changed to and " is statically placed in 80 DEG C of reactions by comparative example 3
15h ", remaining is equal to embodiment 1.
Acquired results are as follows: plasmalogen purity is 83%, extracted amount 72mg (in terms of 10g hydriopsis cumingii powder A1).
Comparative example 4, by " the mesoporous silica gel D2: ethyl alcohol: four tert-butyl esters of metatitanic acid=8g:140mL:35g in 1 step D of embodiment
Amount ratio " being changed to " mesoporous silica gel D2: ethyl alcohol: four tert-butyl esters of metatitanic acid=10g:140mL:30g amount ratio ", remaining is equal to
Embodiment 1.
Acquired results are as follows: plasmalogen purity is 73%, extracted amount 65mg (in terms of 10g hydriopsis cumingii powder A1).
Comparative example 5, by 1 step E of embodiment " the organic solvent V be acetonitrile: water: formic acid: ammonium formate=950mL:
The amount ratio of 50mL:1mL:125mg " be changed to " the organic solvent V be acetonitrile: water: formic acid: ammonium formate=500mL:500mL:
The amount ratio of 1mL:250mg ", remaining is equal to embodiment 1.
Acquired results are as follows: acquired results are as follows: plasmalogen purity is 87%, and extracted amount 71mg is (with 10g hydriopsis cumingii powder A1
Meter).
The above list is only a few specific embodiments of the present invention for finally, it should also be noted that.Obviously, this hair
Bright to be not limited to above embodiments, acceptable there are many deformations.Those skilled in the art can be from present disclosure
All deformations for directly exporting or associating, are considered as protection scope of the present invention.
Claims (3)
1. the method for extracting hydriopsis cumingii plasmalogen using titanium-based mesoporous silica gel composite material, it is characterised in that including following step
It is rapid:
A, hydriopsis cumingii pre-processes:
Rotten shape is made after cleaning decladding, removal capsule gland by hydriopsis cumingii, musculature is taken to clean, powder processed after drying obtains spinnaker
Freshwater mussel powder A1;
B, thick rouge extracts:
It is sufficiently mixed uniformly after organic solvent I is added in hydriopsis cumingii powder A1,2 ± 0.5h is extracted in stirring;
Then water is added, is centrifuged after concussion, removes clear liquid;Lower clear liquid is dry, obtain lipid crude extract B1;
Cold acetone is added into lipid crude extract B1, gained is precipitated as phosphatide runic object B2;
C, alkaline reaction:
Organic solvent II is added to the resulting phosphatide runic object B2 of step B, dissolves phosphatide runic object B2;It is then added and contains alkali
Property substance organic solvent II I, react at room temperature 30 ± 10min;
Extract liquor IV is added in reaction gains, is centrifuged after concussion, lower clear liquid is dry, it is then multiple using organic solvent II
It is molten, obtain alkaline reactant C1;
D, titanium-based mesoporous silica gel composite material is prepared:
Bromide sixteen alkyls pyridine, urea are taken respectively, is uniformly mixed after water is added, and continuously add hexamethylene, isopropanol mixing
It is even;Tetraethyl orthosilicate is added dropwise under agitation, obtains mixture D 1;Bromide sixteen alkyls pyridine: urea: water: hexamethylene:
Isopropanol: tetraethyl orthosilicate=6g:3g:130~170mL:130~170mL:4~6mL:14~16mL amount ratio;
By 1 24 ± 2h of back flow reaction of mixture D;Filter after reaction, gained filter cake first uses ethyl alcohol, water rinse, it is dry after in
500 ± 50 DEG C of 4 ± 0.5h of calcining, obtain mesoporous silica gel D2;
Four tert-butyl ester of metatitanic acid is added into ethyl alcohol, 60 ± 10 DEG C are heated to after mixing, the mesoporous silicon is added under heat-retaining condition
It is uniformly mixed, stirred to doing after glue D2, be then allowed to stand in 100 ± 10 DEG C of 12 ± 2h of reaction, obtain reaction product D3;It is described mesoporous
Silica gel D2: ethyl alcohol: four tert-butyl ester=7.5 of metatitanic acid~8.5g:120~160mL:33~37g amount ratio;
Reaction product D3 is added into hydrothermal reaction kettle and water filters, gained after reaction in 60 ± 10 DEG C of 6 ± 1h of reaction
Filter cake obtains titanium-based mesoporous silica gel composite material in 500 ± 50 DEG C of 5 ± 0.5h of calcining;The reaction product D3: water=1g/20
±5mL;
E, plasmalogen isolates and purifies:
Titanium-based mesoporous silica gel composite material is filled in chromatographic column, the resulting alkaline reactant C1 of step C is added in chromatographic column,
10 ± 2min of chromatographic column first is eluted using organic solvent V, organic solvent VI elution 30 ± 5min of chromatographic column is reused, collects organic
The corresponding leacheate of solvent VI obtains plasmalogen after dry;
The organic solvent V is acetonitrile: water: formic acid: ammonium formate=950mL:50mL:1mL:125mg amount ratio mixes;
The organic solvent VI is acetonitrile: water: formic acid: ammonium formate=700mL:300mL:1mL:750mg amount ratio mixes;Institute
The flow velocity for stating elution is 5mL/min.
2. the method according to claim 1 for extracting hydriopsis cumingii plasmalogen using titanium-based mesoporous silica gel composite material,
It is characterized in that in the step B:
Organic solvent I is 1,2 dichloroethanes: methanol=1:2 volume ratio mixed liquor, hydriopsis cumingii powder A1 and organic solvent I
Solid-liquid ratio is 1g/25 ± 5mL;The dosage of the water is 0.6 ± 0.1 volume times of organic solvent I;The cold acetone temperature is 0
DEG C, dosage is 0.2 ± 0.05 volume times of organic solvent I.
3. the method according to claim 1 for extracting hydriopsis cumingii plasmalogen using titanium-based mesoporous silica gel composite material,
It is characterized in that in the step C:
Organic solvent II is 1,2 dichloroethanes: methanol=1:1 volume ratio mixed liquor, hydriopsis cumingii when dissolution, in step B
Powder A1 and the solid-liquid ratio of organic solvent II are 1g/30 ± 5mL;
Organic solvent II I containing alkaline matter is sodium hydroxide methanol aqueous solution, wherein sodium hydroxide: methanol: water=14g:
The solid-liquid ratio of hydriopsis cumingii powder A1 in 960mL:40mL, the step B and organic solvent II I containing alkaline matter be 1g/5 ±
1mL;
Extract liquor IV is 1,2 dichloroethanes: water=5:3 volume ratio mixed liquor, hydriopsis cumingii powder A1 and extract liquor in step B
The solid-liquid ratio of IV is 1g/50 ± 5mL;
When redissolution, the solid-liquid ratio of the hydriopsis cumingii powder A1 in step B and organic solvent II is 1g/1 ± 0.1mL.
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110160471A1 (en) * | 2008-06-20 | 2011-06-30 | Umeda Jimusho Ltd. | Method for production of highly pure phospholipid, and highly pure sphingomyelin and plasmalogen-type glycerophospholipid produced by the method |
CN105911131A (en) * | 2016-06-17 | 2016-08-31 | 浙江工商大学 | Method for detecting lipid molecules in salmon |
CN106083919A (en) * | 2016-06-11 | 2016-11-09 | 浙江工商大学 | Utilize the method that glycol-based silica gel extracts Ophicephalus argus phospholipid |
CN106153763A (en) * | 2016-06-17 | 2016-11-23 | 浙江工商大学 | The hydrophilic chromatographic tandem mass spectrum detection method of phospholipid in the new prawn of cutter volume |
-
2018
- 2018-10-12 CN CN201811187118.4A patent/CN109369705B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110160471A1 (en) * | 2008-06-20 | 2011-06-30 | Umeda Jimusho Ltd. | Method for production of highly pure phospholipid, and highly pure sphingomyelin and plasmalogen-type glycerophospholipid produced by the method |
CN106083919A (en) * | 2016-06-11 | 2016-11-09 | 浙江工商大学 | Utilize the method that glycol-based silica gel extracts Ophicephalus argus phospholipid |
CN105911131A (en) * | 2016-06-17 | 2016-08-31 | 浙江工商大学 | Method for detecting lipid molecules in salmon |
CN106153763A (en) * | 2016-06-17 | 2016-11-23 | 浙江工商大学 | The hydrophilic chromatographic tandem mass spectrum detection method of phospholipid in the new prawn of cutter volume |
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