CN111560407B - Preparation process of water-soluble rutin derivative - Google Patents
Preparation process of water-soluble rutin derivative Download PDFInfo
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- CN111560407B CN111560407B CN202010448587.8A CN202010448587A CN111560407B CN 111560407 B CN111560407 B CN 111560407B CN 202010448587 A CN202010448587 A CN 202010448587A CN 111560407 B CN111560407 B CN 111560407B
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- rutin derivative
- glucosidase
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- SDEKDNPYZOERBP-UHFFFAOYSA-H iron(ii) phosphate Chemical compound [Fe+2].[Fe+2].[Fe+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O SDEKDNPYZOERBP-UHFFFAOYSA-H 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- 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
Abstract
The invention discloses a preparation process of a water-soluble rutin derivative, belonging to the field of chemistry. The preparation process of the water-soluble rutin derivative comprises the following steps: (1) adding a complex enzyme into the plant coarse powder for enzymolysis to obtain an enzymolysis liquid I; wherein, the components of the complex enzyme comprise cellulase, alpha-amylase and refined neutral protease; (2) adding ferrous ammonium gluconate and beta-glucosidase into the enzymatic hydrolysate I, and carrying out enzymolysis to obtain enzymatic hydrolysate II; (3) filtering the enzymolysis liquid II to remove precipitates to obtain a supernatant; (4) filtering the supernatant by a modified polyvinylidene fluoride membrane, and filtering by a nanofiltration membrane to obtain a filtrate; then concentrating the filtrate, and spray drying to obtain the rutin derivative. The rutin derivative obtained by the preparation process has good water solubility, low energy consumption and high extraction rate, is easy for industrial production, and fully utilizes agricultural resources.
Description
Technical Field
The invention relates to a preparation process of a water-soluble rutin derivative, belonging to the field of chemistry.
Background
Rutin is a flavonoid compound existing in plants, is widely used in medicines and health foods, has the effects of resisting bacteria, diminishing inflammation, resisting radiation, regulating the permeation of capillary walls, preventing the fragility of blood vessels, preventing the rupture of blood vessels, stopping bleeding, extremely strong absorption of ultraviolet rays, resisting oxidation and the like, can be used for preventing hypertension cerebral hemorrhage, diabetes, retinal hemorrhage, hemorrhagic purpura and the like, and can also be used as a food antioxidant and a pigment. The main disadvantages of rutin are low water solubility, poor stability and limited membrane permeability, resulting in low bioavailability. Although rutin has various biological activities detectable in many systems in vitro, the factors hindering the biological effects in vivo are still many. In addition, the low water solubility of rutin limits many of its related practical applications. In order to improve absorption in vivo, a great deal of research workers have been devoted to the preparation of rutin derivatives having better water solubility for the food and pharmaceutical fields.
At present, rutin is mainly extracted from sophora japonica and buckwheat at home, but the resources of the two are limited, and the market demand of the rutin cannot be fully met. Furthermore, despite the fact that rutin has various biological activities which can be detected in a plurality of systems in vitro, rutin has low water solubility, poor stability and limited membrane permeability, thus causing low bioavailability. In addition, although the prior art has a plurality of processes for purifying rutin, the water solubility of the rutin is still not improved, and the recrystallization step is complicated and is not environment-friendly.
Disclosure of Invention
In order to solve at least one problem, the invention provides a preparation process of a water-soluble rutin derivative. The invention does not adopt a conventional organic solvent extraction method, avoids the residual hazard of the organic solvent and solves the problem of increased cost caused by removing the organic solvent in the follow-up process.
The first purpose of the invention is to provide a preparation process of a water-soluble rutin derivative, which comprises the following steps:
(1) adding a complex enzyme into the plant coarse powder for enzymolysis to obtain an enzymolysis liquid I; wherein, the components of the complex enzyme comprise cellulase, alpha-amylase and refined neutral protease;
(2) adding ferrous ammonium gluconate and beta-glucosidase into the enzymatic hydrolysate I obtained in the step (1), and carrying out enzymolysis to obtain enzymatic hydrolysate II;
(3) filtering out the precipitate of the enzymolysis liquid II obtained in the step (2) to obtain a supernatant;
(4) filtering the supernatant obtained in the step (3) by a modified polyvinylidene fluoride membrane, and filtering by a nanofiltration membrane to obtain a filtrate; then concentrating the filtrate, and spray drying to obtain the rutin derivative.
In one embodiment of the invention, the mass ratio of the cellulase, the alpha-amylase and the refined neutral protease in the step (1) is (1-2) to (1-3) to (1-4.5).
In one embodiment of the invention, the mass ratio of the cellulase, the alpha-amylase and the refined neutral protease in the step (1) is 1 (1.5-2) to (2-3).
In one embodiment of the present invention, the mass ratio of the cellulase, the α -amylase and the purified neutral protease in step (1) is 1:1.5: 2.
in one embodiment of the invention, the mass of the complex enzyme in the step (1) is 0.1-1.0% of the mass of the plant coarse powder.
In one embodiment of the invention, the mass of the complex enzyme in the step (1) is 0.3-0.6% of the mass of the plant coarse powder.
In an embodiment of the present invention, the conditions of the enzymatic hydrolysis in step (1) are specifically: performing enzymolysis at 35-50 deg.C for 3-7 hr.
In an embodiment of the present invention, the conditions of the enzymatic hydrolysis in step (1) are specifically: enzymolysis at 40 deg.C for 5 h.
In one embodiment of the present invention, the plant coarse powder in step (1) is obtained by picking and pulverizing dried plant stem, leaf and flower of rutaceae myrcia, tobacco leaf, tomato stem, wolfberry leaf, orange peel, buckwheat flower, etc. as raw materials.
In one embodiment of the present invention, the particle size of the plant meal in step (1) is in the range of 15 to 30 mesh.
In one embodiment of the present invention, the mass ratio of the ferrous ammonium gluconate and the β -glucosidase in the step (2) is 1: 1-4.
In one embodiment of the present invention, the mass ratio of the ferrous ammonium gluconate and the β -glucosidase in the step (2) is 1: 3.
in one embodiment of the present invention, the amount of β -glucosidase added in step (2) is 0.1 to 0.4%; namely, the mass of the beta-glucosidase is 0.1-0.4% of the mass of the plant coarse powder.
In one embodiment of the present invention, the amount of β -glucosidase added in step (2) is 0.3%; namely, the mass of the beta-glucosidase is 0.3 percent of the mass of the plant coarse powder.
In an embodiment of the present invention, the conditions of the enzymatic hydrolysis in step (2) are specifically: the enzymolysis temperature is 50-60 deg.C, and the enzymolysis time is 3-7 h.
In an embodiment of the present invention, the conditions of the enzymatic hydrolysis in step (2) are specifically: the enzymolysis temperature is 55 ℃, and the enzymolysis time is 4 h.
In one embodiment of the present invention, the leaching precipitation in the step (3) is specifically: and centrifuging the enzymolysis liquid II on a centrifuge, and removing precipitated solids to obtain a filtrate.
In one embodiment of the present invention, the parameters of the modified polyvinylidene fluoride membrane (modified hydrophilicity) in step (4) are: the parameters are aperture 0.05-5.0 μm and transmembrane pressure 0.1-0.2 Mpa; the parameters of the nanofiltration membrane are as follows: the molecular weight cut-off is 300-500 dalton, and the transmembrane pressure is 1.0-2.0 MPa.
In one embodiment of the present invention, the concentration in step (4) is specifically: the mixture was concentrated to a 60% strength solution.
In one embodiment of the present invention, the spray drying in step (4) is specifically: the concentrated solution was put into a spray dryer to be spray-dried.
In one embodiment of the present invention, the chemical structural formula of the rutin derivative described in step (4) is:
in one embodiment of the invention, the cellulase, the alpha-amylase, the neutral protease and the beta-glucosidase are purchased from Shandong Kete enzyme preparation Co, and the refined neutral protease is obtained by pulping, centrifuging and ultrafiltering the neutral protease; ferrous ammonium gluconate was purchased from Shanghai Michelin Biotech, Inc.
In one embodiment of the invention, the enzyme activity of the cellulase is 18000U/mL, and the enzyme activity of the alpha-amylase is 6000U/g; the enzyme activity of the neutral protease is 50000U/g, and the enzyme activity after refining is 96000U/g; the enzyme activity of the beta-glucosidase is 320U/g.
The second purpose of the invention is to obtain the rutin derivative by the preparation process.
The third purpose of the invention is to apply the rutin derivative in medicines and health-care foods.
The invention has the beneficial effects that:
(1) the rutin derivative obtained by the preparation process has good water solubility, low energy consumption and high extraction rate, is easy for industrial production, and fully utilizes agricultural resources.
(2) The method has simple equipment, convenient and safe operation, and can obtain the rutin derivative with the purity of 90 percent and the water solubility of 0.51 g/mL.
(3) The method can take dry plant stem leaves and flowers such as the leaves of the rutoside, the tobacco leaves, the tomato stems, the leaves of the medlar, the orange peels, the buckwheat flowers and the like as raw materials, fully utilizes agricultural resources, can be directly used for producing the water-soluble rutin derivatives, solves the problems of complicated steps, large use amount of organic solvents and large amount in the existing rutin production process, and is easy for industrial production.
Drawings
Fig. 1 is a flow chart of a preparation process of the water-soluble rutin derivative in example 1.
FIG. 2 is a graph showing the results of measurement of the radical scavenging rates of the water-soluble rutin derivative, BHA (butylhydroxyanisole), BHT (dibutylhydroxybenzene) and TBHQ (t-butylhydroquinone) in example 1.
Fig. 3 is a liquid phase spectrum of the rutin derivative prepared in example 1.
FIG. 4 is a liquid chromatogram of pure rutin product.
Detailed Description
The following description of the preferred embodiments of the present invention is provided for the purpose of better illustrating the invention and is not intended to limit the invention thereto.
Testing of yield: the yield (%) is the mass (g) of the rutin derivative obtained by separation/mass (g) of the raw material of the plant coarse powder multiplied by 100%.
Testing of purity: the obtained rutin derivative is tested by high performance liquid chromatography (the chromatography is Shimadzu LC-20AT high performance liquid chromatography, the chromatography is C18(4.6 x 250mm, 5 μm) column, the mobile phase is 85 (methanol): 15 (0.5% phosphoric acid water solution), the flow rate is 1.0mL/min, the column temperature is 30 ℃, the detection wavelength is 390nm, the sample feeding amount is 20 μ L, the collection time is 15min), and the purity is determined by area normalization.
Testing of Water solubility: taking 10mL of water in a beaker, slowly adding the obtained rutin derivative under vigorous stirring, stopping adding and recording the mass of the added rutin derivative when insoluble substances begin to appear in the solution, and obtaining the rutin derivative through a formula: the water-soluble (g/mL) ═ rutin derivative mass (g)/10mL was calculated.
Testing of anti-radical performance: accurately weighing 1.487g of phenanthroline to be dissolved in 10mL of absolute ethanol, and then diluting the solution to 100mL by using distilled water to obtain 0.0075M phenanthroline solution. 2.078g of ferrous sulfate heptahydrate were weighed out accurately and dissolved in 100mL of distilled water to obtain a 0.0075M ferrous sulfate solution. Taking 1mL of the prepared o-diazaphenanthrene solution and 1mL of the prepared ferrous phosphate solution respectively, adjusting the pH value of the solution to 7.4 by using a phosphoric acid/potassium phosphate system, and measuring the absorbance A of the solution at 510nmBlank space. Then, 1mL of a 0.1% mass fraction hydrogen peroxide solution was added and reacted in a water bath at 37 ℃ for 1 hour, and the absorbance A was measured at 510nmHydrogen peroxide. Preparing hydrogen peroxide-containing solution according to the same steps, then measuring the anti-free radical agent 15.0mg to be measured, reacting in water bath at 37 ℃ for 1h, and measuring the absorbance A of the solution at 510nmSample (I)The clearance of hydroxyl radicals was calculated.
Wherein the clearance rate is (A)Sample (I)-AHydrogen peroxide)/(ABlank space-AHydrogen peroxide)*100％。
Example 1
A preparation process of water-soluble rutin derivative is shown in figure 1, and comprises the following steps:
(1) cleaning and pulverizing dried tomato stems into coarse powder, and sieving with 15-30 mesh sieve to obtain sieved coarse powder for use;
(2) adding 0.6g of complex enzyme (the mass ratio of cellulase to alpha-amylase to refined neutral protease is 1:1.5: 2) into 100g of sieved coarse powder, and performing enzymolysis for 5 hours at 40 ℃ to obtain an enzymolysis liquid I;
(3) adding ferrous ammonium gluconate and beta-glucosidase (the mass ratio of the ferrous ammonium gluconate to the beta-glucosidase is 1: 3) into the enzymatic hydrolysate I obtained in the step (2), wherein the addition amount of the beta-glucosidase is 0.3 percent of the mass of the tomato stem coarse powder, and carrying out enzymolysis for 4 hours at 55 ℃ to obtain enzymatic hydrolysate II;
(4) filtering out the precipitate of the enzymolysis liquid II obtained in the step (3) to obtain a supernatant;
(5) filtering the supernatant obtained in the step (4) by a modified polyvinylidene fluoride membrane (aperture is 0.05-5.0 μm, transmembrane pressure is 0.1-0.2Mpa), filtering by a nanofiltration membrane (molecular weight cut-off is 300-500 Dalton, transmembrane pressure is 1.0-2.0Mpa), concentrating to the concentration of 60%, and spray drying to obtain the rutin derivative.
And (3) carrying out performance test on the obtained rutin derivative, wherein the test result is as follows: the yield of rutin derivative was 3.0%, the purity was 90.1% (calculated by area normalization method in fig. 3, fig. 4 and tables 1 and 2), and the water solubility was 0.51 g/mL.
Table 1 peak table (detector 390nm) of liquid phase spectrum (fig. 3) of rutin derivative of example 1
| Peak number | Retention time | Area of | Purity (concentration) |
| 1 | 1.910 | 1180 | 0.079 |
| 2 | 3.042 | 1269 | 0.085 |
| 3 | 3.246 | 1852 | 0.124 |
| 4 | 3.533 | 2078 | 0.139 |
| 5 | 3.767 | 1791 | 0.120 |
| 6 | 4.354 | 1350148 | 90.107 |
| 7 | 6.078 | 36972 | 2.467 |
| 8 | 9.581 | 103091 | 6.880 |
| Total of | 1498382 |
Table 2 shows the peak value table (390 nm detector) of the liquid chromatogram (FIG. 4) of pure rutin
| Peak number | Retention time | Area of | Purity (concentration) |
| 1 | 1.910 | 1180 | 0.079 |
| 2 | 3.042 | 1269 | 0.085 |
| 3 | 3.246 | 1852 | 0.124 |
| 4 | 3.533 | 2078 | 0.139 |
| 5 | 3.767 | 1791 | 0.120 |
| 6 | 4.354 | 1350148 | 99.454 |
| Total of | 1358319 |
Note: the purities in tables 1 and 2 were calculated by the area normalization method.
Example 2 optimization of Complex enzyme ratio
The rutin derivatives were obtained by adjusting the mass ratio of the cellulase, the α -amylase and the purified neutral protease in example 1 (specifically, the setting is shown in table 3), and keeping the other parameters unchanged. The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 3:
TABLE 3 Performance test results of rutin derivatives obtained by using different ratios of the vitamin enzyme, the alpha-amylase and the refined neutral protease
As can be seen from table 3: the yield, purity and water solubility of rutin derivatives obtained by different proportions of cellulase, alpha-amylase and refined neutral protease are different, when the ratio of the cellulase: alpha-amylase: the mass ratio of the refined neutral protease is 1:1.5:2, the yield can reach 3 percent, the purity reaches 90.1 percent, and the water solubility reaches 0.51 g/mL.
EXAMPLE 3 optimization of the amount of Complex enzyme (cellulase, alpha-Amylase, purified neutral protease) added
The rutin derivative is obtained by adjusting the addition amount of the complex enzyme (cellulase, alpha-amylase, refined neutral protease) in example 1 (the mass of the complex enzyme is the percentage of the mass of the plant coarse powder) (specifically setting as shown in table 4), and keeping other parameters unchanged.
The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 4:
TABLE 4 Performance test results of rutin derivatives obtained with different amounts of complex enzyme
| Amount of Complex enzyme added (%) | Yield (%) | Purity (%) | Water solubility (g/mL) |
| 0.1 | 0.2 | 92.3 | 0.52 |
| 0.3 | 1.0 | 90.1 | 0.49 |
| 0.6 | 3.0 | 90.1 | 0.51 |
| 0.8 | 2.8 | 85.3 | 0.45 |
| 1.0 | 2.8 | 84.7 | 0.45 |
As can be seen from table 4: the yield is gradually increased along with the increase of the using amount of the compound enzyme, but after the using amount of the compound enzyme exceeds 0.6 percent of the mass of the tomato stem coarse powder, the yield tends to be stable and is not increased along with the increase of the using amount of the compound enzyme.
EXAMPLE 4 optimization of enzymatic hydrolysis temperature of Complex enzymes
The enzymolysis temperature of the complex enzyme (cellulase, alpha-amylase, refined neutral protease) in example 1 was adjusted (specifically set as shown in table 5), and other parameters were kept unchanged to obtain rutin derivatives.
The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 5:
TABLE 5 Performance test results of rutin derivatives obtained by different enzymolysis temperatures of the Complex enzymes
| Enzymolysis temperature (DEG C) of Complex enzyme | Yield (%) | Purity (%) | Water solubility (g/mL) |
| 25 | 0.1 | 75.2 | 0.31 |
| 30 | 1.0 | 79.1 | 0.22 |
| 35 | 2.5 | 85.2 | 0.49 |
| 40 | 3.1 | 90.1 | 0.51 |
| 45 | 3.0 | 85.4 | 0.40 |
| 50 | 2.5 | 85.1 | 0.43 |
| 55 | 0.9 | 88.2 | 0.45 |
The optimum temperature of the cellulase is 26-31 ℃; the optimum temperature of the alpha-amylase is about 55 ℃, and the alpha-amylase is inactivated when the temperature exceeds 60 ℃; the optimum temperature of the refined neutral protease is 40-60 ℃, the activity, temperature requirement, enzymolysis efficiency and the like of the three enzymes are comprehensively considered, and the optimum enzymolysis temperature of the complex enzyme is determined to be 40 ℃.
EXAMPLE 5 optimization of enzymatic hydrolysis time of Complex enzymes
The enzymolysis time of the complex enzyme (cellulase, alpha-amylase, refined neutral protease) in example 1 was adjusted (specifically set as shown in table 6), and other parameters were kept unchanged to obtain rutin derivatives.
The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 6:
TABLE 6 rutin derivatives performance test results obtained by different enzymolysis time with complex enzyme
| Enzymolysis time (h) of Complex enzyme | Yield (%) | Purity (%) | Water solubility (g/mL) |
| 3 | 1.5 | 90.2 | 0.50 |
| 4 | 2.3 | 89.7 | 0.49 |
| 5 | 3.0 | 90.1 | 0.51 |
| 6 | 3.0 | 89.9 | 0.50 |
| 7 | 2.9 | 89.7 | 0.51 |
The enzymolysis time mainly affects the yield of the product, and if the enzymolysis time is too short, the enzymolysis is incomplete and the yield is low; however, if the time is too long, the product in the enzymolysis system may be slightly lost, and the consumption is increased. The optimal enzymolysis time is determined to be 5h through the optimization of the enzymolysis time.
Example 6 optimization of ferrous ammonium gluconate to beta-glucosidase ratio
The mass ratio of ferrous ammonium gluconate to beta-glucosidase in example 1 was adjusted (specifically set as in table 7), and the other parameters were kept unchanged to obtain rutin derivatives.
The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 7:
TABLE 7 Performance test results of rutin derivatives obtained from different mass ratios of ferrous ammonium gluconate and beta-glucosidase
Example 7 optimization of the amount of beta-glucosidase added
The rutin derivative was obtained by adjusting the amount of β -glucosidase added in example 1 (i.e., the mass of β -glucosidase is the percentage of plant meal) (specifically, the setting is shown in table 8), and keeping the other parameters unchanged.
The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 8:
TABLE 8 Performance test results of rutin derivatives prepared with different amounts of beta-glucosidase added
Example 8 optimization of enzymatic hydrolysis temperature of beta-glucosidase
The temperature of the beta-glucosidase in example 1 was adjusted (specifically set as shown in table 9), and other parameters were kept unchanged to obtain rutin derivatives.
The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 9:
TABLE 9 Performance test results of rutin derivatives prepared at different enzymatic hydrolysis temperatures of beta-glucosidase
The optimum temperature of the beta-glucosidase is 40-110 ℃. As can be seen from table 9: the optimal enzymolysis temperature of the beta-glucosidase is 55 ℃.
EXAMPLE 9 optimization of the Filter membranes
The modified polyvinylidene fluoride membrane in example 1 was adjusted to a ceramic membrane or a metal membrane (specifically, the settings are shown in table 10), and the other parameters were kept unchanged to obtain a rutin derivative.
The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 10:
TABLE 10 results of performance tests on rutin derivatives prepared with different filters
| Kind of filter membrane | Yield (%) | Purity (%) | Water solubility (g/mL) |
| Ceramic membrane | 1.5 | 80.2 | 0.40 |
| Modified polyvinylidene fluoride membrane | 3.0 | 90.1 | 0.51 |
| Metal film | 2.5 | 85.5 | 0.45 |
The plant raw materials such as stem leaves and flowers contain more components such as pigment, lignin, protein, tannin and the like, after a plurality of times of enzymolysis and purification extraction, the supernatant obtained in the step (4) still contains more impurities such as pigment, tannin and the like, and the impurities are removed by double-membrane filtration of a microfiltration membrane and a nanofiltration membrane in sequence according to the molecular weight and the properties of the impurities.
Through the test of three microfiltration membranes such as ceramic membrane, modified polyvinylidene fluoride membrane, metal membrane and the like, the test results in table 10 show that: the modified polyvinylidene fluoride membrane has the best impurity removal effect.
Example 10
The rutin derivative is prepared by taking the rutabaga leaves, the tobacco leaves, the tomato stems, the wolfberry leaves, the orange peels and the buckwheat flowers as raw materials according to the method in the embodiment 1.
The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 11:
TABLE 11 results of performance test of rutin derivatives prepared from different raw materials
| Kind of raw material | Yield (%) | Purity (%) | Water solubility (g/mL) |
| Rumex leaves | 1.0 | 89.6 | 0.51 |
| Tobacco leaf | 1.5 | 91.2 | 0.51 |
| Tomato stem | 3.0 | 90.1 | 0.51 |
| Chinese wolfberry leaf | 2.4 | 85.2 | 0.47 |
| Orange peel | 0.9 | 90.1 | 0.51 |
| Buckwheat flower | 1.5 | 90.1 | 0.52 |
Comparative example 1
The complex enzyme setting of the embodiment 1 is adjusted to be shown in table 12, and other parameters are consistent with those of the embodiment 1, so that the rutin derivative is obtained.
The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 12:
TABLE 12 results of performance tests on rutin derivatives prepared by different enzymes
Comparative example 2
And (3) adding no ferrous ammonium gluconate, and keeping other parameters consistent with those in the embodiment 1 to obtain the rutin derivative.
The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 13:
TABLE 13 Performance test results of rutin derivatives prepared in the absence or presence of ferrous ammonium gluconate
| Presence or absence of ferrous ammonium gluconate | Yield (%) | Purity (%) | Water solubility (g/mL) |
| Is provided with | 3.0 | 90.1 | 0.51 |
| Is not provided with | 0.5 | 84.1 | 0.43 |
Comparative example 3
After obtaining the enzymolysis liquid II, carrying out recrystallization or column chromatography according to a conventional method without adopting micro-membrane filtration, and keeping other parameters consistent with those of the embodiment 1 to obtain the rutin derivative.
The obtained rutin derivatives were subjected to performance tests, and the test results are shown in table 14:
TABLE 14 Performance test results of rutin derivatives prepared by different post-treatment methods
| Post-processing method | Yield (%) | Purity (%) | Water solubility (g/mL) |
| Column chromatography | 3.6 | 95.0 | 0.61 |
| Recrystallization | 2.1 | 89.5 | 0.50 |
| Micro-membrane filtration | 3.0 | 90.1 | 0.51 |
As can be seen from table 14: the product loss is serious in recrystallization, the column chromatography is high in product purity and yield, but the operation is very complicated, a large amount of solvents and silica gel consumables are consumed, and the consumed time is long. Considering the cost comprehensively, the best post-treatment mode is micro-membrane filtration.
Example 4
During normal physiological activities of the human body, some free radicals are generated, which destroy cellular structures and interfere with normal physiological activities of the human body. Therefore, the intake of some substances capable of removing free radicals is very important for the health maintenance of human bodies, and due to the structural particularity of rutin, rutin has strong anti-free radical performance. The anti-free radical property can be commonly used by o-diazaphenanthrene-Fe2+The measurement was performed by spectrophotometry. The reaction of ferrous iron with hydrogen peroxide can generate hydroxyl radicals which can oxidize phenanthroline to change its absorbance, and the addition of an anti-radical agent can attenuate this change, so that the performance of the anti-radical agent can be evaluated by measuring the change in absorbance.
The water-soluble rutin derivative obtained in example 1 was examined for its anti-radical properties by selecting a control using BHA (butylhydroxyanisole), BHT (dibutylhydroxybenzene), and TBHQ (t-butylhydroquinone) as an anti-radical agent, and the results of the experiments are shown in fig. 2.
As can be seen from fig. 2, among several types of radical scavengers tested, the rutin derivative obtained in example 1 has the highest radical scavenging rate, and thus the rutin derivative prepared in example 1 has the best anti-radical properties.
Although the present invention has been described with reference to the preferred embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (7)
1. A process for preparing a water-soluble rutin derivative, which is characterized by comprising the following steps:
(1) adding a complex enzyme into the plant coarse powder for enzymolysis to obtain an enzymolysis liquid I; wherein, the components of the complex enzyme comprise cellulase, alpha-amylase and refined neutral protease;
(2) adding ferrous ammonium gluconate and beta-glucosidase into the enzymatic hydrolysate I obtained in the step (1), and carrying out enzymolysis to obtain enzymatic hydrolysate II;
(3) filtering out the precipitate of the enzymolysis liquid II obtained in the step (2) to obtain a supernatant;
(4) filtering the supernatant obtained in the step (3) by a modified polyvinylidene fluoride membrane, and filtering by a nanofiltration membrane to obtain a filtrate; then concentrating and spray drying the filtrate to obtain a rutin derivative;
the plant coarse powder in the step (1) is obtained by selecting, cleaning and crushing dry plant stem leaves and flowers of rutabaga leaves, tobacco leaves, tomato stems, medlar leaves, orange peels and buckwheat flowers as raw materials;
the mass ratio of the cellulase, the alpha-amylase and the refined neutral protease in the step (1) is 1:1.5: 2;
the mass ratio of the ferrous ammonium gluconate to the beta-glucosidase in the step (2) is 1: 3;
the molecular weight cut-off of the nanofiltration membrane in the step (4) is 300-500 daltons;
the chemical structural formula of the rutin derivative in the step (4) is as follows:
2. the process as claimed in claim 1, wherein the mass of the complex enzyme in the step (1) is 0.1-1.0% of the mass of the plant meal.
3. The process according to claim 1, wherein the conditions of the enzymatic hydrolysis in step (1) are in particular: performing enzymolysis at 35-50 deg.C for 3-7 hr.
4. The process as claimed in claim 1, wherein the mass of the β -glucosidase in step (2) is 0.1-0.4% of the plant meal.
5. The process of claim 1, wherein the conditions of the enzymolysis in the step (2) are as follows: the enzymolysis temperature is 50-60 deg.C, and the enzymolysis time is 3-7 h.
6. A rutin derivative prepared by the process of any of claims 1-5, wherein the rutin derivative has the chemical formula:
7. the use of the rutin derivative of claim 6 in the preparation of medicaments and health foods.
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