CN109369705B - Method for extracting hyriopsis cumingii plasmalogen by using titanium-based mesoporous silica gel composite material - Google Patents
Method for extracting hyriopsis cumingii plasmalogen by using titanium-based mesoporous silica gel composite material Download PDFInfo
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- CN109369705B CN109369705B CN201811187118.4A CN201811187118A CN109369705B CN 109369705 B CN109369705 B CN 109369705B CN 201811187118 A CN201811187118 A CN 201811187118A CN 109369705 B CN109369705 B CN 109369705B
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- 241000382840 Hyriopsis cumingii Species 0.000 title claims abstract description 57
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 239000000741 silica gel Substances 0.000 title claims abstract description 46
- 229910002027 silica gel Inorganic materials 0.000 title claims abstract description 46
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 title claims abstract description 35
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- 239000010936 titanium Substances 0.000 title claims abstract description 35
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- 238000000034 method Methods 0.000 title claims abstract description 16
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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 11
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- 238000003756 stirring Methods 0.000 claims description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 10
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- 239000000126 substance Substances 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
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 8
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 3
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- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 claims description 2
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- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
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- 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
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- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 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
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- -1 acetal phospholipid Chemical class 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
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- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
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- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
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- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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- 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 Kinetics & Catalysis (AREA)
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- Engineering & Computer Science (AREA)
- Inorganic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
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- Silicates, Zeolites, And Molecular Sieves (AREA)
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Abstract
The invention discloses a method for extracting hyriopsis cumingii plasmalogen by using a titanium-based mesoporous silica gel composite material, which comprises the following steps: extracting crude fat from hyriopsis cumingii powder A1; carrying out alkaline reaction on the obtained lipid crude extract B1 to obtain an alkaline reactant C1; preparing a titanium-based mesoporous silica gel composite material; filling the titanium-based mesoporous silica gel composite material into a chromatographic column, adding an alkaline reactant C1 into the chromatographic column, leaching the chromatographic column by using an organic solvent, collecting leacheate, and drying to obtain the plasmalogen. The extraction method has the characteristics of high plasmalogen yield, good product purity, utilization of waste resources and contribution to environmental protection.
Description
Technical Field
The invention relates to a method for extracting hyriopsis cumingii plasmalogen, in particular to a method for extracting hyriopsis cumingii plasmalogen by using a titanium-based mesoporous silica gel composite material.
Background
Hyriopsis cumingii (Hyriopsis cumingii Lea) is commonly called freshwater mussel, pearl mussel and Hyriopsis cumingii, and the freshwater bivalves mollusk belongs to Bivalvia, Unionidae and Hyriopsis. The clam is large and flat, the shell surface is black or tan, thick and hard, the length is nearly 20 cm, and the back edge extends upwards to form a sail-shaped back wing, so that the clam is in a triangular shape. The hyriopsis cumingii is a unique species in China, has important economic value, and the pearls produced in the freshwater pearl mussels are thick, strong in luster and excellent in quality. The hyriopsis cumingii has thick and tough meat quality and heavy earthy taste, is difficult to eat, is usually discarded as waste or used for feed processing, and has low economic added value. Then it contains rich protein, lipid, vitamins and inorganic mineral elements, etc., and has better processing and utilizing space.
Plasmalogen is an ether-containing phospholipid characterized by an ether linkage at the sn-1 position and an ester linkage at the sn-2 position, wherein the sn-1 position is typically linked to C16: 0; the fatty alcohol of C18:0 or C18:1 has polyunsaturated fatty acids (PUFAs) connected to the sn-2 position and ethanol amino or choline connected to the head. The research shows that the muscle and the internal organs of the shellfish contain plasmalogen. Because of the special structure of the alkene ether linkage at the sn-1 position, the plasmalogen has more comprehensive physiological and biochemical activities compared with common phospholipids. With the development of molecular biology, various biological activities of plasmalogens have been discovered and confirmed in the research of pathogenesis and phospholipidomics of various human diseases. Research shows that plasmalogen as a special phospholipid molecule shows various different physiological functions in the metabolic process, and abnormal metabolism of plasmalogen can cause a series of diseases. Plasmalogens have been continuously demonstrated to have a direct link to alzheimer's disease for half a century. A large number of experiments prove that the plasmalogen can be used as follows: promoting nerve cell regeneration, promoting neuron protrusion, strengthening nerve cell, protecting brain cell, resisting oxidation, preventing nerve cell apoptosis, reducing neuroinflammation, metabolizing beta amyloid protein accumulation, improving memory and learning ability, and improving Alzheimer's disease.
Therefore, the research on the plasmalogen in the hyriopsis cumingii has important significance for researching novel medicines and health-care functional foods and improving the additional value of the hyriopsis cumingii.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a method for extracting hyriopsis cumingii plasmalogen by using a titanium-based mesoporous silica gel composite material; the extraction method has the characteristics of high plasmalogen yield, good product purity (91.6%), utilization of waste resources and environmental friendliness.
In order to solve the technical problem, the invention provides a method for extracting hyriopsis cumingii acetal phospholipid by using a titanium-based mesoporous silica gel composite material, which comprises the following steps:
A. pretreating hyriopsis cumingii:
cleaning hyriopsis cumingii, removing shell, removing sac gland, cleaning muscle tissue, making into paste (using chopper mixer), drying, and making into powder to obtain hyriopsis cumingii powder A1;
B. extracting crude fat:
adding organic solvent I into hyriopsis cumingii powder A1, mixing, stirring (200 + -40 rpm), and extracting for 2 + -0.5 h;
adding water, shaking (violent shaking), centrifuging (centrifuging at 9000rpm for 20min), and collecting supernatant (after layering solution, collecting supernatant); drying the lower clear liquid (drying under reduced pressure) to obtain a crude lipid extract B1;
adding cold acetone (acetone pre-cooled to 0 deg.C) into the crude lipid extract B1 to obtain precipitate as crude phospholipid B2;
remarking: phospholipids are insoluble in acetone, and the lower the acetone temperature, the poorer the phospholipid solubility; therefore, the phospholipid is separated out after cold acetone is added;
C. alkaline reaction:
adding an organic solvent II into the phospholipid crude product B2 obtained in the step B to dissolve (fully dissolve) the phospholipid crude product B2, then adding an organic solvent III containing alkaline substances, and reacting at room temperature for 30 +/-10 min;
adding the extract IV into the reaction product, shaking (violent shaking), centrifuging (centrifuging at 9000rpm for 20min), drying the lower clear liquid (drying under reduced pressure), and redissolving by using an organic solvent II to obtain an alkaline reactant C1;
D. preparing a titanium-based mesoporous silica gel composite material:
respectively taking bromohexadecyl pyridine and urea, adding water, uniformly mixing, and continuously adding cyclohexane and isopropanol, and uniformly mixing; dropwise adding tetraethyl orthosilicate (the dropwise adding time is 4-6 minutes) under the stirring condition (200 +/-40 rpm) to obtain a mixture D1; bromohexadecylpyridine: urea: water: cyclohexane: isopropyl alcohol: tetraethyl orthosilicate 6 g: 3 g: 130-170 mL: 130-170 mL: 4-6 mL: a dosage ratio of 14 to 16mL (preferably a dosage ratio of 6 g: 3 g: 150 mL: 150 mL: 5 mL: 15 mL);
the mixture D1 is refluxed (about 70 ℃) and reacted for 24 +/-2 h; filtering after the reaction is finished, rinsing the obtained filter cake with ethanol and water, drying, and calcining in a muffle furnace at 500 +/-50 ℃ for 4 +/-0.5 h to obtain mesoporous silica gel D2;
adding tetrabutyl titanate into ethanol, mixing, heating to 60 +/-10 ℃, adding the mesoporous silica gel D2 under the condition of heat preservation, uniformly mixing, stirring until the mixture is dry (the ethanol is volatilized), and standing at 100 +/-10 ℃ for reaction for 12 +/-2 hours to obtain a reaction product D3; the mesoporous silica gel D2: ethanol: 7.5-8.5 g of tetra-tert-butyl titanate: 120-160 mL: a dosage ratio of 33-37 g (preferably 8 g: 140 mL: 35 g);
adding a reaction product D3 and water into a hydrothermal reaction kettle, reacting at 60 +/-10 ℃ for 6 +/-1 h, filtering after the reaction is finished, and calcining the obtained filter cake in a muffle furnace at 500 +/-50 ℃ for 5 +/-0.5 h to obtain the titanium-based mesoporous silica gel composite material; the reaction product D3: water is 1g/20 plus or minus 5 mL;
E. separation and purification of plasmalogen:
filling the titanium-based mesoporous silica gel composite material into a chromatographic column (a chromatographic column with the size of 30mm multiplied by 300 mm), adding the alkaline reactant C1 obtained in the step C into the chromatographic column, firstly leaching the chromatographic column by using an organic solvent V for 10 +/-2 min, then leaching the chromatographic column by using an organic solvent VI for 30 +/-5 min, collecting a leacheate corresponding to the organic solvent VI, and drying (drying under reduced pressure) to obtain the plasmalogen;
the organic solvent V is acetonitrile: water: formic acid: ammonium formate 950 mL: 50mL of: 1mL of: 125mg of the components are mixed according to the dosage ratio; the organic solvent VI is acetonitrile: water: formic acid: ammonium formate 700 mL: 300 mL: 1mL of: 750mg of the components are mixed; the flow rate of the elution is 5 mL/min.
Remarking: and B, when the amount of the hyriopsis cumingii powder A1 in the step B is 10g, the amount of the titanium-based mesoporous silica gel composite material is 50 +/-10 g.
As an improvement of the method for extracting hyriopsis cumingii plasmalogen by using the titanium-based mesoporous silica gel composite material, in the step B:
the organic solvent I is 1,2 dichloroethane: methanol 1: 2, the material-to-liquid ratio of the hyriopsis cumingii powder A1 to the organic solvent I is 1g/25 +/-5 mL; the dosage of the water is 0.6 +/-0.1 volume time of the organic solvent I; the temperature of the cold acetone is 0 ℃, and the dosage of the cold acetone is 0.2 +/-0.05 volume times of that of the organic solvent I.
As a further improvement of the method for extracting hyriopsis cumingii plasmalogen by using the titanium-based mesoporous silica gel composite material, in the step C:
the organic solvent II is 1, 2-dichloroethane: methanol 1: 1 volume ratio of the mixed solution, wherein when the mixed solution is dissolved, the feed-liquid ratio of the hyriopsis cumingii powder A1 to the organic solvent II in the step B is 1g/30 +/-5 mL;
the organic solvent III containing alkaline substances is sodium hydroxide methanol aqueous solution, wherein the ratio of sodium hydroxide: methanol: water 14 g: 960 mL: 40mL, wherein the feed-liquid ratio of the hyriopsis cumingii powder A1 in the step B to the organic solvent III containing the alkaline substance is 1g/5 +/-1 mL;
extract IV was 1,2 dichloroethane: water 5: 3, the feed-liquid ratio of the hyriopsis cumingii powder A1 to the extract liquid IV in the step B is 1g/50 +/-5 mL;
and (3) during re-dissolving, the feed-liquid ratio of the hyriopsis cumingii powder A1 to the organic solvent II in the step B is 1g/1 +/-0.1 mL.
The method takes hyriopsis cumingii as a raw material, and prepares the high-content plasmalogen by a series of technical means such as crude lipid extraction, alkaline reaction, separation of titanium-based mesoporous silica gel composite material and the like. Wherein the alkaline reaction can effectively decompose phospholipid ester bonds and retain plasmalogen with alkene ether bonds. Titanium-based mesoporous silica gel composite material has better selectivity to phosphate groups of phospholipid, and simultaneously mesoporous silica gel has larger surface area than common silica gel, thereby obviously improving the loading capacity of titanium-based, and the titanium-based mesoporous silica gel composite material has obvious separation effect on plasmalogen, the purity of the plasmalogen can reach 91.6%, and the extraction rate is high (98 mg of plasmalogen (calculated by 10g of hyriopsis cumingii powder A1)). The method for extracting hyriopsis cumingii plasmalogen by using the titanium-based mesoporous silica gel composite material has the characteristics of good product quality, high added value of products, utilization of waste resources and contribution to environmental protection. The invention provides a method for extracting hyriopsis cumingii plasmalogen by using a titanium-based mesoporous silica gel composite material.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
FIG. 1 is a liquid chromatography mass spectrometry identification diagram of plasmalogen obtained by separating hyriopsis cumingii from a titanium-based mesoporous silica gel composite material.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
the violent shaking is 150-300 rpm.
Embodiment 1, a method for extracting hyriopsis cumingii plasmalogen by using a titanium-based mesoporous silica gel composite material sequentially comprises the following steps:
A. pretreating hyriopsis cumingii:
cleaning 1kg hyriopsis cumingii, removing shell, removing sac gland, cleaning muscle tissue, making into paste with a chopper mixer, drying at 80 deg.C until water content is less than or equal to 0.5% (wt%), pulverizing to powder, and sieving with 60 mesh sieve to obtain hyriopsis cumingii powder A1.
B. Extracting crude fat:
taking hyriopsis cumingii powder A110 g, adding 250mL of 1, 2-dichloroethane/methanol mixed solution (1,2 dichloroethane: methanol is 1: 2, v/v), fully and uniformly mixing, stirring and extracting at 200rpm for 2h, then adding 150mL of water, violently shaking for 10 minutes, centrifuging at 9000rpm for 20min, and removing clear liquid after the solution is layered; drying the lower clear liquid under reduced pressure (0.08Mpa, 60 deg.C to constant weight) to obtain lipid crude extract B1;
50mL of acetone (as a solvent) precooled to 0 ℃ was added to the crude lipid extract B1, and the precipitated precipitate was phospholipid crude product B2.
C. Alkaline reaction:
adding 300mL of organic solvent II into the total phospholipid crude material B2 obtained in the step B so as to fully dissolve the phospholipid crude material B2, then adding 50mL of organic solvent III containing alkaline substances, and reacting for 30min at room temperature;
500mL of extract IV was added to the reaction mixture, followed by vigorous shaking for 10 minutes, centrifugation at 9000rpm for 20min, drying the supernatant under reduced pressure (0.08MPa, 60 ℃ C. to constant weight), and redissolving in 10mL of organic solvent II to obtain basic reactant C1 (product C1).
The organic solvent II is 1, 2-dichloroethane: methanol 1: 1 volume ratio of the mixed solution,
the organic solvent III containing alkaline substances is sodium hydroxide: methanol: water 14 g: 960 mL: 40mL of the aqueous solution of sodium hydroxide in methanol was prepared.
Extract IV was 1,2 dichloroethane: water 5: 3 volume ratio of the mixed solution.
D. Preparing a titanium-based mesoporous silica gel composite material:
respectively taking 6g of bromohexadecylpyridine and 3g of urea, adding 150mL of pure water, uniformly mixing, and continuously adding 150mL of cyclohexane and 5mL of isopropanol, uniformly mixing; 15mL of tetraethyl orthosilicate was added dropwise (dropwise addition time 5 minutes) with stirring at 200rpm to give a mixture D1;
the mixture D1 was reacted at reflux (about 70 ℃ C.) for 24 h; filtering after the reaction is finished, rinsing the obtained filter cake with 50ml of ethanol and 50ml of water, drying (namely, after water is not dripped), and calcining for 4 hours in a muffle furnace at 500 ℃ to obtain mesoporous silica gel D2;
adding 35g of tetrabutyl titanate into 140mL of ethanol, heating to 60 ℃ after mixing, continuously adding 8g of mesoporous silica gel D2 under the condition of heat preservation, uniformly mixing, stirring at the heat preservation condition until the mixture is dry (namely, stirring until the ethanol is volatilized, and the stirring time is about 10 minutes), and standing at 100 ℃ for reaction for 12 hours to obtain a reaction product D3;
and adding 10g of reaction product D3 and 200mL of water into a hydrothermal reaction kettle, reacting for 6h at 60 ℃, filtering after the reaction is finished, and calcining the obtained filter cake in a muffle furnace for 5h at 500 ℃ to obtain the titanium-based mesoporous silica gel composite material.
E. Separation and purification of plasmalogen:
filling 50g of titanium-based mesoporous silica gel composite material into a chromatography column with the diameter of 30mm multiplied by 300mm, adding an alkaline reactant C1 obtained in the step C into the chromatography column, then leaching the chromatography column for 10min by using an organic solvent V, then leaching the chromatography column for 30min by using an organic solvent VI, collecting a leaching solution corresponding to the organic solvent VI, and drying under reduced pressure (0.08Mpa, drying at 60 ℃ to constant weight) to obtain 98mg of plasmalogen (calculated by 10g of hyriopsis cumingii powder A1); the purity of the plasmalogen can reach 91.6 percent through detection.
The organic solvent V is acetonitrile: water: formic acid: ammonium formate 950 mL: 50mL of: 1mL of: 125mg of the components are mixed according to the dosage ratio; the organic solvent VI is acetonitrile: water: formic acid: ammonium formate 700 mL: 300 mL: 1mL of: 750mg of the components are mixed; the flow rate during rinsing is 5 mL/min.
And E, analyzing the plasmalogen separated in the step E by liquid chromatography mass spectrometry, comparing the plasmalogen with a standard substance, and identifying that the plasmalogen mainly comprises plasmalogen phosphatidylcholine, plasmalogen inositol, plasmalogen phosphatidylserine and plasmalogen phosphatidylcholine. The chromatogram for plasmalogen is shown in FIG. 1.
Comparative example 1, the titanium-based mesoporous silica gel composite material obtained in the step E of the example 1 is changed into C18, and the using amount is not changed; the rest is equivalent to embodiment 1.
The results obtained were: the purity of plasmalogen was 70%, and the extraction amount was 32mg (based on 10g of hyriopsis cumingii powder A1).
Comparative example 2-1, preparation of bromohexadecylpyridine in titanium-based mesoporous silica gel composite material according to step D "of example 1: urea: water: cyclohexane: isopropyl alcohol: tetraethyl orthosilicate 6 g: 3 g: 150mL of: 150mL of: 5mL of: the dosage ratio of 15mL is changed into bromohexadecylpyridine: urea: water: cyclohexane: isopropyl alcohol: tetraethyl orthosilicate 7 g: 2 g: 150mL of: 150mL of: 5mL of: 15mL of the active ingredient; the rest is equivalent to embodiment 1.
The results obtained were: the purity of plasmalogen was 62%, and the extraction amount was 27mg (based on 10g of hyriopsis cumingii powder A1).
Comparative example 2-2, preparation of titanium-based mesoporous silica gel composite material in step D "of example 1, bromohexadecylpyridine: urea: water: cyclohexane: isopropyl alcohol: tetraethyl orthosilicate 6 g: 3 g: 150mL of: 150mL of: 5mL of: the dosage ratio of 15mL is changed into bromohexadecylpyridine: urea: water: cyclohexane: isopropyl alcohol: tetraethyl orthosilicate 5 g: 4 g: 150mL of: 150mL of: 5mL of: 15mL of the active ingredient; the rest is equivalent to embodiment 1.
The results obtained were: the purity of plasmalogen was 51%, and the extraction amount was 30mg (based on 10g of hyriopsis cumingii powder A1).
Comparative examples 2-3, preparation of titanium-based mesoporous silica gel composite material in step D "of example 1, bromohexadecylpyridine: urea: water: cyclohexane: isopropyl alcohol: tetraethyl orthosilicate 6 g: 3 g: 150mL of: 150mL of: 5mL of: the dosage ratio of 15mL is changed into bromohexadecylpyridine: urea: water: cyclohexane: isopropyl alcohol: tetraethyl orthosilicate 6 g: 3 g: 100mL of: 100mL of: 6mL of: the dosage ratio of 12 mL; the rest is equivalent to embodiment 1.
The results obtained were: the purity of plasmalogen was 80.2%, and the extraction amount was 70mg (based on 10g of hyriopsis cumingii powder A1).
Comparative example 3, the "12 h reaction at 100 ℃ still" in step D of example 1 was changed to "15 h reaction at 80 ℃ still", and the rest was the same as in example 1.
The results obtained were: the purity of plasmalogen was 83%, and the extraction amount was 72mg (based on 10g of hyriopsis cumingii powder A1).
Comparative example 4, the "mesoporous silica gel D2 in step D of example 1: ethanol: tetra-tert-butyl titanate 8 g: 140mL of: the dosage ratio of 35g is changed into that of the mesoporous silica gel D2: ethanol: tetra-tert-butyl titanate 10 g: 140mL of: the ratio of 30g used "was otherwise identical to that of example 1.
The results obtained were: the purity of plasmalogen was 73%, and the extraction amount was 65mg (based on 10g of hyriopsis cumingii powder A1).
Comparative example 5, example 1 step E "the organic solvent V was acetonitrile: water: formic acid: ammonium formate 950 mL: 50mL of: 1mL of: 125mg of the organic solvent V is changed into acetonitrile: water: formic acid: ammonium formate 500 mL: 500 mL: 1mL of: 250mg in a ratio ", the remainder was the same as in example 1.
The results obtained were: the results obtained were: the purity of plasmalogen was 87%, and the extraction amount was 71mg (based on 10g of hyriopsis cumingii powder A1).
Finally, it is also noted that the above-mentioned lists merely illustrate a few specific embodiments of the invention. It is obvious that the invention is not limited to the above embodiments, but that many variations are possible. All modifications which can be derived or suggested by a person skilled in the art from the disclosure of the present invention are to be considered within the scope of the invention.
Claims (3)
1. The method for extracting hyriopsis cumingii plasmalogen by using the titanium-based mesoporous silica gel composite material is characterized by comprising the following steps of:
A. pretreating hyriopsis cumingii:
cleaning hyriopsis cumingii, removing shell, removing sac gland, cleaning muscle tissue, making into paste, drying, and making into powder to obtain hyriopsis cumingii powder A1;
B. extracting crude fat:
adding an organic solvent I into hyriopsis cumingii powder A1, fully and uniformly mixing, and stirring and extracting for 2 +/-0.5 h;
then adding water, shaking and centrifuging, and taking down clear liquid; drying the lower clear liquid to obtain a crude lipid extract B1;
adding cold acetone into the crude lipid extract B1 to obtain precipitate as crude phospholipid extract B2;
the organic solvent I is 1,2 dichloroethane: methanol 1: 2 volume ratio of mixed solution;
C. alkaline reaction:
adding an organic solvent II into the phospholipid crude extract B2 obtained in the step B to dissolve the phospholipid crude extract B2; then adding an organic solvent III containing alkaline substances, and reacting at room temperature for 30 +/-10 min;
adding the extract IV into the reaction product, shaking, centrifuging, drying the lower clear liquid, and redissolving by using an organic solvent II to obtain an alkaline reactant C1;
the organic solvent II is 1, 2-dichloroethane: methanol 1: 1 volume ratio of mixed solution;
the organic solvent III containing alkaline substances is sodium hydroxide methanol aqueous solution, wherein the ratio of sodium hydroxide: methanol: water 14 g: 960 mL: 40 mL;
extract IV was 1,2 dichloroethane: water 5: 3 volume ratio of mixed solution;
D. preparing a titanium-based mesoporous silica gel composite material:
respectively taking bromohexadecyl pyridine and urea, adding water, uniformly mixing, and continuously adding cyclohexane and isopropanol, and uniformly mixing; tetraethyl orthosilicate is dropwise added under the stirring condition to obtain a mixture D1; bromohexadecylpyridine: urea: water: cyclohexane: isopropyl alcohol: tetraethyl orthosilicate 6 g: 3 g: 150mL of: 150mL of: 5mL of: 15mL of the active ingredient;
refluxing the mixture D1 for 24 +/-2 h; filtering after the reaction is finished, rinsing the obtained filter cake with ethanol and water, drying, and calcining at 500 +/-50 ℃ for 4 +/-0.5 h to obtain mesoporous silica gel D2;
adding tetrabutyl titanate into ethanol, mixing, heating to 60 +/-10 ℃, adding the mesoporous silica gel D2 under the condition of heat preservation, uniformly mixing, stirring to be dry, standing at 100 +/-10 ℃ and reacting for 12 +/-2 hours to obtain a reaction product D3; the mesoporous silica gel D2: ethanol: tetra-tert-butyl titanate 8 g: 140mL of: the dosage ratio of 35 g;
adding a reaction product D3 and water into a hydrothermal reaction kettle, reacting at 60 +/-10 ℃ for 6 +/-1 h, filtering after the reaction is finished, and calcining the obtained filter cake at 500 +/-50 ℃ for 5 +/-0.5 h to obtain the titanium-based mesoporous silica gel composite material; the reaction product D3: water is 1g/20 plus or minus 5 mL;
E. separation and purification of plasmalogen:
filling the titanium-based mesoporous silica gel composite material into a chromatographic column, adding the alkaline reactant C1 obtained in the step C into the chromatographic column, firstly leaching the chromatographic column for 10 +/-2 min by using an organic solvent V, then leaching the chromatographic column for 30 +/-5 min by using an organic solvent VI, collecting a leacheate corresponding to the organic solvent VI, and drying to obtain plasmalogen;
the organic solvent V is acetonitrile: water: formic acid: ammonium formate 950 mL: 50mL of: 1mL of: 125mg of the components are mixed according to the dosage ratio; the organic solvent VI is acetonitrile: water: formic acid: ammonium formate 700 mL: 300 mL: 1mL of: 750mg of the components are mixed; the flow rate of the elution is 5 mL/min.
2. The method for extracting hyriopsis cumingii plasmalogen by using the titanium-based mesoporous silica gel composite material as claimed in claim 1, wherein in the step B:
the feed-liquid ratio of the hyriopsis cumingii powder A1 to the organic solvent I is 1g/25 +/-5 mL; the dosage of the water is 0.6 +/-0.1 volume time of the organic solvent I; the temperature of the cold acetone is 0 ℃, and the dosage of the cold acetone is 0.2 +/-0.05 volume times of that of the organic solvent I.
3. The method for extracting hyriopsis cumingii plasmalogen by using the titanium-based mesoporous silica gel composite material as claimed in claim 1, wherein in the step C:
when dissolving, the feed-liquid ratio of the hyriopsis cumingii powder A1 to the organic solvent II in the step B is 1g/30 +/-5 mL;
the feed-liquid ratio of the hyriopsis cumingii powder A1 to the organic solvent III containing the alkaline substance in the step B is 1g/5 +/-1 mL;
the feed-liquid ratio of the hyriopsis cumingii powder A1 to the extract liquid IV in the step B is 1g/50 +/-5 mL;
and (3) during re-dissolving, the feed-liquid ratio of the hyriopsis cumingii powder A1 to the organic solvent II in the step B is 1g/1 +/-0.1 mL.
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| 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 |
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| 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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