CN116925157A - Method for extracting quinoa bran saponins by eutectic solvent - Google Patents
Method for extracting quinoa bran saponins by eutectic solvent Download PDFInfo
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- CN116925157A CN116925157A CN202310916691.9A CN202310916691A CN116925157A CN 116925157 A CN116925157 A CN 116925157A CN 202310916691 A CN202310916691 A CN 202310916691A CN 116925157 A CN116925157 A CN 116925157A
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- eutectic solvent
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- 239000002904 solvent Substances 0.000 title claims abstract description 164
- 229930182490 saponin Natural products 0.000 title claims abstract description 153
- 235000017709 saponins Nutrition 0.000 title claims abstract description 153
- 150000007949 saponins Chemical class 0.000 title claims abstract description 152
- 230000005496 eutectics Effects 0.000 title claims abstract description 149
- 240000006162 Chenopodium quinoa Species 0.000 title claims abstract description 102
- 238000000034 method Methods 0.000 title claims abstract description 36
- 238000000605 extraction Methods 0.000 claims abstract description 146
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims abstract description 65
- 238000002414 normal-phase solid-phase extraction Methods 0.000 claims abstract description 23
- 238000010438 heat treatment Methods 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 7
- 238000011084 recovery Methods 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract description 6
- 239000000243 solution Substances 0.000 claims description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 239000007788 liquid Substances 0.000 claims description 30
- 239000000284 extract Substances 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000007864 aqueous solution Substances 0.000 claims description 28
- 239000003085 diluting agent Substances 0.000 claims description 18
- 238000007865 diluting Methods 0.000 claims description 16
- 238000002137 ultrasound extraction Methods 0.000 claims description 12
- 238000004108 freeze drying Methods 0.000 claims description 10
- 238000001035 drying Methods 0.000 claims description 9
- 239000006228 supernatant Substances 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims description 4
- 235000019743 Choline chloride Nutrition 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims description 4
- 229960003178 choline chloride Drugs 0.000 claims description 4
- GLHSTLAMCVIPPF-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;pyrrolidin-2-one Chemical compound O=C1CCCN1.C=CC1=CC=CC=C1C=C GLHSTLAMCVIPPF-UHFFFAOYSA-N 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 claims description 3
- 229960004063 propylene glycol Drugs 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- 229960003237 betaine Drugs 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 235000013772 propylene glycol Nutrition 0.000 claims 1
- 238000004128 high performance liquid chromatography Methods 0.000 abstract description 13
- 238000012360 testing method Methods 0.000 abstract description 13
- 241000196324 Embryophyta Species 0.000 abstract description 8
- 238000013461 design Methods 0.000 abstract description 7
- 238000005457 optimization Methods 0.000 abstract description 7
- 238000012216 screening Methods 0.000 abstract description 6
- ZDGWGNDTQZGISB-UHFFFAOYSA-N acetic acid;perchloric acid Chemical compound CC(O)=O.OCl(=O)(=O)=O ZDGWGNDTQZGISB-UHFFFAOYSA-N 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 238000004737 colorimetric analysis Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 230000000694 effects Effects 0.000 description 14
- 239000000370 acceptor Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000013478 data encryption standard Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 241000282414 Homo sapiens Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- XUDNWQSXPROHLK-OACYRQNASA-N 2-phenyl-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=CC=CC=2)OC2=CC=CC=C2C1=O XUDNWQSXPROHLK-OACYRQNASA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- -1 acetic acid-perchloric acid saponin Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G3/00—Glycosides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
- A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Botany (AREA)
- Health & Medical Sciences (AREA)
- Mycology (AREA)
- General Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Medicines Containing Plant Substances (AREA)
- Steroid Compounds (AREA)
Abstract
The application provides a method for extracting quinoa bran saponins by using a eutectic solvent, which comprises the steps of preparing 42 eutectic solvents by a heating and stirring method, screening out an optimal eutectic solvent by using a vanillin-glacial acetic acid-perchloric acid colorimetric method and a high performance liquid chromatography, taking the optimal eutectic solvent as an extraction solvent, screening out optimal extraction conditions by an optimization test and a Design-Expert13 Design response surface test, and separating and recovering quinoa bran saponins and the eutectic solvent by a solid phase extraction method; compared with the existing extraction method, the extraction process is simple, the extraction solvent is cheap and easy to obtain, the extraction condition is mild, the extraction rate of the saponin is high, the extraction rate is obviously higher than that of the traditional organic solvent, the separation and recovery process is simple, the eutectic solvent can be recovered and reused, the production cost is low, the reaction process is green and environment-friendly and safe, and the method can be widely applied to the technical field of plant saponin extraction.
Description
Technical Field
The application relates to the technical field of plant saponin extraction, in particular to a method for extracting quinoa bran saponins by using a eutectic solvent.
Background
Quinoa is the only food meeting all nutritional value requirements of human beings, and is considered by the united nations grain and agriculture organizations to be the perfect 'full-nutrition food' most suitable for human beings. Quinoa is rich in protein, amino acid, starch, cellulose, mineral matters and the like, the content of saponin and flavonol glycoside in seeds is high, and according to researches, the content of saponin in quinoa seed bran is about 3% -8%. The quinoa bran saponins have wide biological activity, and have the effects of bacteriostasis, antioxidation, antivirus, anti-cytotoxicity, anticancer, immunity enhancement and the like, and a small amount of in vitro experimental researches prove that the quinoa bran saponins have the in vivo lipid-lowering potential, so that the research on the extraction of the quinoa bran saponins has important significance for the development and utilization of bioactive substances in plants.
At present, common extraction solvents for extracting plant saponins are methanol, ethanol and water, and a 70% methanol ultrasonic extraction method and a 70% ethanol ultrasonic extraction method in the traditional extraction method have good extraction effects on plant saponins, but a large amount of organic solvents are needed in the extraction process, and have the defects of high toxicity, easiness in volatilization, easiness in causing environmental pollution and the like, so that the cost, the harm and the environmental friendliness of the extraction process of the plant saponins are high. Therefore, there is a strong need to develop an extraction solvent which is environment-friendly, safe and low in cost.
In 2003, professor Abbott, university of leset, united kingdom, proposed a green solvent: eutectic Solvents (DESs). DESs are eutectic mixtures formed by hydrogen bond bonding of a certain amount of hydrogen bond acceptors and hydrogen bond donors, most commonly choline chloride, and most hydrogen bond acceptors are amides, carboxylic acids, polyols, and the like. DESs have the characteristics of low melting point, low toxicity, low price, easy preparation, recoverability and the like, so that the preparation of the natural eutectic solvent as an extracting agent of bioactive substances in plants accords with the development trend of green chemistry.
Disclosure of Invention
In order to solve the technical problems, the technical scheme adopted by the application is to provide a method for extracting quinoa bran saponins by using a eutectic solvent, so as to solve the technical problems of higher cost, higher hazard and poorer environmental protection of the existing quinoa bran saponins extraction method.
The embodiment of the application provides a method for extracting quinoa bran saponins by using a eutectic solvent, which comprises the following steps:
(1) Preparation of the eutectic solvent: adding a hydrogen bond donor and a hydrogen bond acceptor into a container, heating and stirring to mix, so as to obtain a eutectic solvent;
(2) Extraction of saponin extract: diluting the eutectic solvent to obtain eutectic solvent aqueous solution, adding the quinoa bran into the eutectic solvent aqueous solution, heating for ultrasonic extraction, collecting the solution, and centrifuging the solution to obtain supernatant, namely the saponin extract;
(3) Separation and recovery of saponin and eutectic solvent: diluting the saponin extract to obtain a diluent, extracting and separating the diluent by using a solid phase extraction column, collecting effluent, freeze-drying the effluent, and recovering the eutectic solvent; washing the solid phase extraction column by using an organic solvent, collecting washing liquid, and drying the washing liquid to obtain the solid namely the quinoa bran saponin.
Preferably, in the step (1), the hydrogen bond donor is any one of choline chloride and betaine, the hydrogen bond acceptor is any one of citric acid, urea, glucose, 1, 2-propylene glycol and glycerol, and the molar ratio of the hydrogen bond donor to the hydrogen bond acceptor is 1:0.5-1:4.
Preferably, in the step (1), the heating mode is water bath heating, the heating temperature is 70 ℃, and the heating and stirring are carried out until clear and transparent liquid is formed.
Preferably, in the step (2), the water content of the aqueous solution of the eutectic solvent is 20 to 80% vol.
Preferably, in the step (2), the feed liquid ratio of the quinoa bran to the eutectic solvent aqueous solution is 0.05-0.30 g/mL.
Preferably, in the step (2), the extraction temperature is 15-75 ℃ and the extraction time is 10-110 min.
Preferably, in the step (2), the rotation speed of the centrifugal treatment is 5000r/min, and the time of the centrifugal treatment is 10min.
Preferably, in the step (3), the dilution factor of the diluent is 10 times, and the solid phase extraction column is a polystyrene divinylbenzene pyrrolidone solid phase extraction column.
Preferably, in the step (3), the specific extraction process is as follows: before extraction, the solid phase extraction column is activated by primary water and methanol, then the diluent is placed in the solid phase extraction column for 10min, and the diluent is arranged to pass through the solid phase extraction column at a speed of 1 drop/s.
Preferably, in the step (3), the freeze-drying temperature is-40 ℃ and the freeze-drying time is 6-8 hours; the organic solvent is methanol, the drying temperature is-80 ℃, and the drying time is 4-5 h.
The beneficial effects of the application are as follows: the application provides a method for extracting quinoa bran saponins by using a eutectic solvent, which comprises the steps of preparing 42 eutectic solvents by a heating and stirring method, screening out an optimal eutectic solvent by using a vanillin-glacial acetic acid-perchloric acid colorimetric method and a high performance liquid chromatography, taking the optimal eutectic solvent as an extraction solvent, screening out an optimal extraction condition by an optimization test and a Design-Expert13 Design response surface test, enriching quinoa bran saponins by a solid phase extraction method, and recovering the eutectic solvent for reuse by freeze drying effluent liquid, thereby solving the problem that the eutectic solvent and an extract are not easy to separate; compared with the existing extraction method, the extraction process is simple, the extraction solvent is cheap and easy to obtain, the extraction condition is mild, the extraction rate of the saponin is high, the extraction rate is obviously higher than that of the traditional organic solvent, the separation and recovery process is simple, the eutectic solvent can be recovered and reused, the production cost is low, and the reaction process is environment-friendly and safe.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings that are needed in the embodiments or the description of the prior art will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present application, and that other drawings can be obtained according to these drawings without inventive effort for a person skilled in the art.
FIG. 1 is a graph showing the effect of the eutectic solvent of examples 1 to 16 and 35 to 42 on the extraction yield of quinoa saponins;
FIG. 2 is a graph showing the effect of the eutectic solvent of examples 16, 17 to 34 on the extraction yield of quinoa saponins;
FIG. 3 is a graph showing the effect of eutectic solvents with different water contents on the extraction rate of quinoa saponins;
FIG. 4 is a graph showing the effect of eutectic solvent on the extraction yield of quinoa saponins at different feed/liquid ratios;
FIG. 5 is a graph showing the effect of eutectic solvent on the extraction yield of quinoa saponins at various times of extraction;
FIG. 6 is a graph showing the effect of eutectic solvent on the extraction yield of quinoa saponins at different extraction temperatures.
Detailed Description
In order to make the technical problems, technical schemes and beneficial effects to be solved more clear, the application is further described in detail below with reference to the accompanying drawings and embodiments. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the application. The methods used in the application are all conventional methods unless specified otherwise; the raw materials and devices used, unless otherwise specified, are all conventional commercial products.
1. Eutectic solvent, preparation and optimization thereof
The present application provides a eutectic solvent prepared according to the kinds and molar ratios of hydrogen bond donor and hydrogen bond acceptor of examples 1 to 42 in table 1.
TABLE 1 species and molar ratios of Hydrogen bond donor and Hydrogen bond acceptor of examples 1-42
The present application also provides a method for preparing a eutectic solvent according to the kinds and molar ratios of the hydrogen bond donor and the hydrogen bond acceptor of examples 1 to 42 in table 1, which is specifically as follows:
according to the kinds and mole ratios of the hydrogen bond donor and the hydrogen bond acceptor in examples 1 to 42 in table 1, the corresponding hydrogen bond donor and hydrogen bond acceptor were accurately weighed, and then the hydrogen bond donor and hydrogen bond acceptor were added into a beaker, put into a magnetic stirrer, heated to 70 ℃ in a water bath, stirred and mixed until clear and transparent liquid was formed, and 42 eutectic solvents of examples 1 to 42 as shown in table 1 were obtained.
The application also provides a method for optimizing the eutectic solvent in the embodiment 1 to the embodiment 42 in the table 1, which comprises the following steps:
(1) Primary optimization of eutectic solvents:
the extraction rate of the eutectic solvent of examples 1 to 16 and 35 to 42 to the quinoa bran saponins is measured by using a vanillin-glacial acetic acid-perchloric acid colorimetric method, and the specific steps are as follows:
(1) determination of a standard curve:
accurately weighing 1mg saponin standard Q 1 In a 10mL volumetric flask, methanol is used for volume fixing to obtain a standard saponin solution with the concentration of 0.1 mg/mL; precisely measuring 0mL, 0.8mL, 1mL, 1.5mL, 2.5mL and 3mL standard saponin solutions respectively according to the amount in Table 2, placing in a dry test tube with a plug, evaporating to dryness at 60 ℃, taking out, cooling, sequentially adding 0.2mL 5% vanillin glacial acetic acid solution and 0.8mL perchloric acid in a fume hood, shaking, heating in a water bath at 60 ℃ for 15min, cooling with flowing water for 10min, adding 4mL glacial acetic acid, shaking, standing for 30min to obtain 6 groups of Q 1 A standard solution; 6 groups of Q are respectively measured by adopting an enzyme-labeled instrument 1 The absorbance of the standard solution at 560nm absorption wavelength, the absorbance is taken as an ordinate, the saponin concentration is taken as an abscissa, and a standard curve Y of the saponin concentration and the absorbance is calculated 1 ＝7.251X 1 +0.0622，R 2 = 0.9937; wherein, saponin standard substance Q 1 The structural formula of (2) is shown in the following figure:
TABLE 2Q 1 Content of each component in the standard solution
(2) Extraction of saponin extract:
the eutectic solvents of examples 1 to 16 and 35 to 42 were diluted to obtain an aqueous solution of the eutectic solvent having a water content of 30% vol, and then 0.2g of quinoa bran was added to 4mL of the aqueous solution of the eutectic solvent having a water content of 30% vol (the ratio of quinoa bran to the aqueous solution of the eutectic solvent is 0.05 g/mL), and the mixture was subjected to ultrasonic extraction at 55℃for 55 minutes, and after extraction for 55 minutes, the solution was collected, and centrifuged at 5000r/min for 10 minutes to obtain a supernatant, namely a saponin extract.
(3) Determination of the extraction yield of saponins:
diluting the saponin extract by 20 times to obtain diluent, measuring absorbance of the diluent at 560nm absorption wavelength by using an enzyme-labeled instrument, and passing through a standard curve Y 1 The extraction yield of the corresponding saponins from the quinoa bran saponins by the eutectic solvents of examples 1 to 16 and 35 to 42 was calculated, and the results are shown in fig. 1.
Referring to fig. 1, which is a graph showing the influence of the eutectic solvents of examples 1 to 16 and 35 to 42 on the extraction rate of quinoa saponins, as can be seen from fig. 1, the eutectic solvent DES4 (1:4) prepared in example 16 has the highest extraction rate of quinoa saponins, and thus the eutectic solvent DES4 (1:4) prepared in example 16 is selected as the optimal eutectic solvent.
(2) Secondary optimization of eutectic solvent:
the extraction rate of the eutectic solvent of example 16, example 17 to example 34 on the quinoa bran saponins was measured by high performance liquid chromatography, and the specific steps are as follows:
(1) determination of a standard curve:
methanol is used as solvent to prepare the mixture with the concentration of 10ug/mL,Q of 50ug/mL, 300ug/mL, 500ug/mL, 750ug/mL, 1500ug/mL 1 Standard saponin solution and Q 2 Standard saponin solution, and then measuring Q by high performance liquid chromatography 1 Standard saponin solution and Q 2 And (3) measuring a standard saponin solution by taking peak area integral values corresponding to different concentrations as an ordinate and taking the saponin concentration as an abscissa to obtain a standard curve of the saponin concentration and the peak area integral value: q (Q) 1 Standard curve is Y 2 ＝12208X 2 +734719，R 2 ＝0.989，Q 2 Standard curve is Y 3 ＝329063X 3 +65472，R 2 =0.996; wherein, saponin standard substance Q 2 The structural formula of (2) is shown in the following figure:
(2) extraction of saponin extract:
the eutectic solvents of examples 16 and 17 to 34 were diluted to obtain an aqueous solution of the eutectic solvent having a water content of 30% vol, respectively, then 0.2g of quinoa bran was added to 4mL of the aqueous solution of the eutectic solvent having a water content of 30% vol (the feed liquid ratio of quinoa bran to the aqueous solution of the eutectic solvent was 0.05 g/mL), the temperature was raised to 55℃for ultrasonic extraction, the solutions were collected after extraction for 55 minutes, and the solutions were centrifuged at 5000r/min for 10 minutes to obtain a supernatant, namely a saponin extract.
(3) Determination of the extraction yield of saponins:
diluting the saponin extract 10 times to obtain diluent, measuring the diluent by high performance liquid chromatography to obtain peak area integral value of the diluent, and substituting the peak area integral value into standard curve Y 2 And Y 3 The results of calculating the respective concentration values and taking the sum of the two concentration values as the concentration of the saponins, namely the extraction rates of the eutectic solvents of example 16 and examples 17 to 34 on the saponins of the quinoa bran, are shown in fig. 2.
Referring to fig. 2, which is a graph showing the influence of the eutectic solvents of examples 16 and 17-34 on the extraction rate of quinoa saponins, it can be seen from fig. 2 that the eutectic solvent DES7 (1:1) prepared in example 27 has the highest extraction rate of quinoa saponins, and therefore the eutectic solvent DES7 (1:1) prepared in example 27 is selected as the optimal eutectic solvent.
2. Extraction and optimization of quinoa bran saponins by eutectic solvent
To further confirm the reliability of the eutectic solvent on the extraction effect of quinoa bran saponins, the extraction conditions of the optimal eutectic solvent DES7 (1:1) were tested below.
(1) Water content of eutectic solvent
The application provides a method for extracting quinoa bran saponins by using a eutectic solvent, which comprises the following steps:
(1) extraction of saponin extract:
diluting the optimal eutectic solvent DES7 (1:1) to obtain eutectic solvent aqueous solutions with water contents of 20% vol, 30% vol, 40% vol, 50% vol, 60% vol, 70% vol and 80% vol respectively shown in examples 43-49 in Table 3, adding the quinoa bran into the eutectic solvent aqueous solutions with different water contents in examples 43-49 according to the feed liquid ratio of the quinoa bran to the eutectic solvent aqueous solution of 0.05g/mL, heating to 50 ℃ for ultrasonic extraction, collecting the solutions after extraction for 50min, centrifuging the solutions at a rotation speed of 5000r/min for 10min, and obtaining supernatant, namely the saponin extract of examples 43-49.
TABLE 3 conditions for extracting quinoa bran saponins with the eutectic solvent of examples 43-49
(2) Determination of the extraction yield of saponins:
diluting the saponin extracts of examples 43 to 49 by 10 times to obtain diluted solutions, measuring the diluted solutions by high performance liquid chromatography to obtain peak area integral values of the diluted solutions, and separating the peak area integral valuesIs substituted into standard curve Y 2 And Y 3 Respectively calculating corresponding concentration values, taking the sum of the two concentration values as the concentration of the saponins, namely the extraction rate of the eutectic solvents with different water contents in the examples 43-49 on the quinoa bran saponins, and drawing a corresponding influence relation graph, wherein the result is shown in figure 3.
Referring to fig. 3, which is a graph showing the effect of eutectic solvents with different water contents on the extraction rate of quinoa saponins, it is shown in fig. 3 that when the water content of the eutectic solvents increases from 20% vol to 80% vol, the extraction rate of saponins tends to increase and decrease, and when the water content is 40% vol, the extraction rate of saponins is highest, so that increasing the water content can reduce the viscosity of the eutectic solvents and increase the extraction rate of quinoa saponins, but the water content is too high to affect the formation of hydrogen bonds and thus the extraction of quinoa saponins, so that the water content of the eutectic solvents is preferably 40%.
(2) Feed-to-liquid ratio of quinoa bran to eutectic solvent
The application provides a method for extracting quinoa bran saponins by using a eutectic solvent, which comprises the following steps:
(1) extraction of saponin extract:
diluting the optimal eutectic solvent DES7 (1:1) to obtain an aqueous solution of the eutectic solvent with the water content of 40% vol, adding the quinoa bran into the aqueous solution of the eutectic solvent with the water content of 40% vol according to the feed-liquid ratio of the quinoa bran to the eutectic solvent shown in examples 50-55 in table 4, heating to 50 ℃ for ultrasonic extraction for 50min, collecting the solution, centrifuging the solution at a rotation speed of 5000r/min for 10min, and obtaining supernatant, namely the saponin extract of examples 50-55.
TABLE 4 conditions for extracting quinoa bran saponins with the eutectic solvent of examples 50 to 55
(2) Determination of the extraction yield of saponins:
diluting the saponin extracts of examples 50-55 by 10 times to obtain diluted solutions, measuring the diluted solutions by high performance liquid chromatography to obtain peak area integral values of the diluted solutions, and substituting the peak area integral values into standard curve Y 2 And Y 3 And (3) respectively calculating corresponding concentration values, taking the sum of the two concentration values as the concentration of the saponins, namely the extraction rate of the eutectic solvent on the quinoa bran saponins in different feed-liquid ratios in examples 50-55, and drawing a corresponding influence relation graph, wherein the result is shown in figure 4.
Referring to FIG. 4, which is a graph showing the effect of the eutectic solvent on the extraction rate of the quinoa bran saponins at different feed ratios, it is known from FIG. 4 that when the feed ratio of the quinoa bran to the eutectic solvent is increased from 0.05g/mL to 0.30g/mL, the saponin extraction rate tends to be increased and then decreased, and when the feed ratio is 0.10g/mL, the saponin extraction rate is highest, because the quinoa bran cannot be completely leached into the eutectic solvent at too high feed ratio, thereby affecting the extraction of the quinoa bran saponins by the eutectic solvent, and therefore the feed ratio of the quinoa bran to the eutectic solvent is preferably 0.10g/mL.
(3) Extraction time
The application provides a method for extracting quinoa bran saponins by using a eutectic solvent, which comprises the following steps:
(1) extraction of saponin extract:
diluting the optimal eutectic solvent DES7 (1:1) to obtain an aqueous solution of the eutectic solvent with the water content of 40%vol, adding the quinoa bran into the aqueous solution of the eutectic solvent with the water content of 40%vol according to the feed liquid ratio of the quinoa bran to the aqueous solution of the eutectic solvent of 0.05g/mL, heating to 50 ℃ for ultrasonic extraction, collecting the solution after the ultrasonic extraction is finished according to the extraction time shown in the examples 56-61 in the table 5, centrifuging the solution at the rotation speed of 5000r/min for 10min, and obtaining the supernatant, namely the saponin extract of the examples 56-61.
TABLE 5 conditions for extracting quinoa bran saponins with the eutectic solvent of examples 56-61
(2) Determination of the extraction yield of saponins:
diluting the saponin extracts of examples 56-61 by 10 times to obtain diluted solutions, measuring the diluted solutions by high performance liquid chromatography to obtain peak area integral values of the diluted solutions, and substituting the peak area integral values into the standard curve Y 2 And Y 3 Respectively calculating corresponding concentration values, taking the sum of the two concentration values as the concentration of the saponins, namely the extraction rate of the eutectic solvent on the quinoa bran saponins in different extraction times in examples 56-61, and drawing a corresponding influence relation graph, wherein the result is shown in figure 3.
Referring to fig. 3, the effect of the eutectic solvent on the extraction rate of the quinoa bran saponins at different extraction times is shown in fig. 3, and it is known that when the extraction time is increased from 10min to 110min, the extraction rate of saponins tends to be increased and then slightly decreased, and when the extraction time is 70min, the extraction rate of saponins is the highest, so that the extraction time is preferably 70min in consideration of the cost and the power consumption.
(4) Extraction temperature
The application provides a method for extracting quinoa bran saponins by using a eutectic solvent, which comprises the following steps:
(1) extraction of saponin extract:
diluting the optimal eutectic solvent DES7 (1:1) to obtain an aqueous solution of the eutectic solvent with the water content of 40%vol, adding the quinoa bran into the aqueous solution of the eutectic solvent with the water content of 40%vol according to the feed liquid ratio of the quinoa bran to the aqueous solution of the eutectic solvent of 0.05g/mL, heating for ultrasonic extraction according to the extraction temperature shown in examples 62-66 in table 6, collecting the solution after 20min of extraction, centrifuging the solution at the rotation speed of 5000r/min for 10min, and obtaining supernatant, namely the saponin extract of examples 62-66.
TABLE 6 conditions for extracting quinoa saponins with the eutectic solvent of examples 62 to 66
(2) Determination of the extraction yield of saponins:
diluting the saponin extracts of examples 62-66 by 10 times to obtain diluted solutions, measuring the diluted solutions by high performance liquid chromatography to obtain peak area integral values of the diluted solutions, and substituting the peak area integral values into standard curve Y 2 And Y 3 Respectively calculating corresponding concentration values, taking the sum of the two concentration values as the concentration of the saponins, namely the extraction rate of the eutectic solvent on the quinoa bran saponins at different extraction temperatures in examples 43-49, and drawing a corresponding influence relation graph, wherein the result is shown in fig. 4.
Referring to fig. 4, which is a graph showing the effect of the eutectic solvent on the extraction rate of the quinoa bran saponins at different extraction temperatures, it is understood from fig. 4 that the extraction rate of saponins tends to increase when the extraction temperature is increased from 15 ℃ to 75 ℃ at different extraction temperatures, and thus the extraction temperature is preferably 75 ℃.
(5) Design-Expert13 Design response surface test
The experimental method comprises the following steps: according to the results of examples 50 to 55, 56 to 61 and 62 to 66, three factors and three levels were set, and test design and model fitting were performed using BBD to obtain a temperature (X 4 Temperature, degree centigrade), extraction time (X 5 Min), feed-liquid ratio (X 6 g/mL) as independent variable, with saponin extraction rate (Y) 4 Mg/g) was 17 trials of response variables and experimental data simulated by software Design-Expert13 are shown in tables 7 and 8.
TABLE 7 Star Point design test conditions and results for the extraction yield of saponins
TABLE 8 analysis of variance data statistics for models of saponin extraction yield
Wherein P <0.05, significance is; p <0.01, significance is x; p <0.001, significance is x; the remainder were not significant.
As can be seen from Table 8, the BBD model has an F-value of 8.10, P=0.0058 <0.01, R 2 = 0.9124 > 0.9, which indicates that the established BBD model reaches a significant level, and has statistical significance; the mismatching term represents the probability that the predicted value and the actual value of the model are not fit, the P value of the mismatching term is 0.4907, the mismatching term is not obvious, and the model is properly selected; according to BBD model test analysis, the extraction conditions of the quinoa bran saponins are preferably as follows: the extraction temperature is 74.897 ℃, the extraction time is 89.144min, and the feed-liquid ratio is 0.053g/mL.
The Design-Expert13 Design response surface test shows that the trend of the influence of the extraction temperature, the extraction time, the feed-liquid ratio and the interaction thereof on the extraction rate of the saponin is similar, and the influence significance of each factor is as follows: the feed liquid ratio is more than the extraction temperature and the extraction time.
(6) Extraction solvent
In order to confirm the reliability of the extraction effect of the eutectic solvent on the quinoa bran saponins in a further step, the extraction test of the optimal eutectic solvent DES7 (1:1) and the conventional organic solvents (70% methanol, 70% ethanol, 100% ethanol) was performed under the preferred extraction conditions, the extraction time was selected to be 89min, the extraction temperature was selected to be 75 ℃, and the feed to liquid ratio was selected to be 0.05g/mL, considering the actual operation.
(1) Extraction of saponin extract:
diluting the optimal eutectic solvent DES7 (1:1) to obtain an aqueous solution of the eutectic solvent with the water content of 40%vol, then respectively adding the quinoa bran into the aqueous solution of the eutectic solvent with the water content of 40%vol, 70% methanol, 70% ethanol and 100% ethanol according to the feed liquid ratio of the quinoa bran to the aqueous solution of the eutectic solvent of 0.05g/mL, heating to 75 ℃ for ultrasonic extraction, extracting for 89min, collecting the solution, centrifuging the solution at the rotation speed of 5000r/min for 10min, and obtaining supernatant, namely the saponin extract of examples 67-70.
(2) Determination of the extraction yield of saponins:
diluting the saponin extracts of examples 67-70 by 10 times to obtain diluted solutions, measuring the diluted solutions by high performance liquid chromatography to obtain peak area integral values of the diluted solutions, and substituting the peak area integral values into standard curve Y 2 And Y 3 The respective concentration values were calculated, and the sum of the two concentration values was taken as the saponin concentration, which is the extraction rate of the quinoa bran saponins by the different extraction solvents of examples 67 to 70, and the results are shown in table 9.
TABLE 9 extraction conditions of quinoa bran saponins with different extraction solvents of examples 67-70
As can be seen from table 9, the extraction rate of the eutectic solvent for the quinoa bran saponins is significantly higher than that of the conventional organic solvents (70% methanol, 70% ethanol, 100% ethanol), and therefore the extraction solvent is preferably the eutectic solvent.
In summary, the extraction conditions of the quinoa bran saponins are preferably as follows: the extraction solvent is a eutectic solvent prepared from choline chloride and 1, 2-propylene glycol according to a molar ratio of 1:1, the water content of the eutectic solvent is 40%vol, the feed liquid ratio of quinoa bran to the eutectic solvent is 0.05g/mL, the extraction time is 89min, and the extraction temperature is 75 ℃.
3. Separation and recovery of quinoa bran saponin and eutectic solvent
Extracting and separating the diluent with 10 times of dilution times in the embodiment 43-66 by using a polystyrene divinylbenzene pyrrolidone solid-phase extraction column, activating the solid-phase extraction column by using 12mL of primary water and 12mL of methanol before extraction, then placing the diluent in the solid-phase extraction column for 10min, then arranging the diluent to pass through the solid-phase extraction column at a speed of 1 drop/s, collecting effluent liquid, and freeze-drying the effluent liquid at the temperature of minus 40 ℃ for 6-8 h, thus recovering the eutectic solvent for application; washing the solid phase extraction column by using 12mL of methanol, collecting washing liquid, and drying the washing liquid at the temperature of-80 ℃ for 4-5 hours to obtain solid, namely the quinoa bran saponin.
In summary, the application provides a method for extracting quinoa bran saponins by using a eutectic solvent, which comprises the steps of preparing 42 eutectic solvents by a heating and stirring method, screening out an optimal eutectic solvent by using a vanillin-glacial acetic acid-perchloric acid colorimetric method and a high performance liquid chromatography, taking the optimal eutectic solvent as an extraction solvent, screening out an optimal extraction condition by an optimization test and a Design-Expert13 Design response surface test, enriching quinoa bran saponins by a solid phase extraction method, and recovering the eutectic solvent for reuse by freeze drying effluent liquid, thereby solving the problem that the eutectic solvent and the extract are not easy to separate; compared with the existing extraction method, the extraction process is simple, the extraction solvent is cheap and easy to obtain, the extraction condition is mild, the extraction rate of the saponin is high, the extraction rate is obviously higher than that of the traditional organic solvent, the separation and recovery process is simple, the eutectic solvent can be recovered and reused, the production cost is low, the reaction process is green and environment-friendly and safe, and the method can be widely applied to the technical field of plant saponin extraction.
It should be noted that:
(1) Since the eutectic solvents of examples 17 to 34 themselves undergo a color reaction with the vanillin-glacial acetic acid-perchloric acid saponin developer to affect the detection result of the saponin extraction rate, the application adopts high performance liquid chromatography to detect the extraction rate of the eutectic solvents of examples 17 to 34 on the quinoa bran saponins, and then adopts high performance liquid chromatography to detect the extraction rate of the eutectic solvents DES4 (1:4) of example 16 on the quinoa bran saponins, and compared with the two, the optimal eutectic solvents are screened.
(2) When the solid-phase extraction method is adopted to separate and recycle the eutectic solvent and the quinoa bran Pi Zao glycoside, the freeze-drying time of the eutectic solvent is 6-8 h, the drying time of the quinoa bran saponin is 4-5 h, and the drying time is determined according to actual conditions.
The above embodiments are only for illustrating the technical solution of the present application, and not for limiting the same; although the application has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present application, and are intended to be included in the scope of the present application.
Claims (10)
1. The method for extracting the quinoa bran saponins by using the eutectic solvent is characterized by comprising the following steps of:
(1) Preparation of the eutectic solvent: adding a hydrogen bond donor and a hydrogen bond acceptor into a container, heating and stirring to mix, so as to obtain a eutectic solvent;
(2) Extraction of saponin extract: diluting the eutectic solvent to obtain eutectic solvent aqueous solution, adding the quinoa bran into the eutectic solvent aqueous solution, heating for ultrasonic extraction, collecting the solution, and centrifuging the solution to obtain supernatant, namely the saponin extract;
(3) Separation and recovery of saponin and eutectic solvent: diluting the saponin extract to obtain a diluent, extracting and separating the diluent by using a solid phase extraction column, collecting effluent, freeze-drying the effluent, and recovering the eutectic solvent; washing the solid phase extraction column by using an organic solvent, collecting washing liquid, and drying the washing liquid to obtain the solid namely the quinoa bran saponin.
2. The method for extracting quinoa bran saponins by using eutectic solvent according to claim 1, wherein in the step (1), the hydrogen bond donor is any one of choline chloride and betaine, the hydrogen bond acceptor is any one of citric acid, urea, glucose, 1, 2-propanediol and glycerol, and the molar ratio of the hydrogen bond donor to the hydrogen bond acceptor is 1:0.5-1:4.
3. The method for extracting quinoa bran saponins from quinoa according to claim 1, wherein in step (1), the heating mode is water bath heating, the heating temperature is 70 ℃, and the heating and stirring are carried out until clear and transparent liquid is formed.
4. The method for extracting quinoa bran saponin by using the eutectic solvent according to claim 1, wherein in the step (2), the water content of the aqueous solution of the eutectic solvent is 20-80% vol.
5. The method for extracting quinoa bran saponin by using the eutectic solvent according to claim 1, wherein in the step (2), the feed liquid ratio of the quinoa bran to the aqueous solution of the eutectic solvent is 0.05-0.30 g/mL.
6. The method for extracting quinoa bran saponins with eutectic solvent according to claim 1, wherein in step (2), the extraction temperature is 15-75 ℃, and the extraction time is 10-110 min.
7. The method for extracting quinoa bran saponins by using eutectic solvent according to claim 1, wherein in step (2), the rotation speed of the centrifugation is 5000r/min, and the time of the centrifugation is 10min.
8. The method for extracting quinoa bran saponins from quinoa according to claim 1, wherein in the step (3), the dilution factor of the diluent is 10 times, and the solid phase extraction column is a polystyrene divinylbenzene pyrrolidone solid phase extraction column.
9. The method for extracting quinoa bran saponins by using eutectic solvent as claimed in claim 1, wherein in the step (3), the specific extraction process is as follows: before extraction, the solid phase extraction column is activated by primary water and methanol, then the diluent is placed in the solid phase extraction column for 10min, and the diluent is arranged to pass through the solid phase extraction column at a speed of 1 drop/s.
10. The method for extracting quinoa bran saponins by using eutectic solvent according to claim 1, wherein in the step (3), the freeze drying temperature is-40 ℃, and the freeze drying time is 6-8 hours; the organic solvent is methanol, the drying temperature is-80 ℃, and the drying time is 4-5 h.
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