CN115400138B - Method for solubilising hesperetin-7-O-glucoside and solubilised complexes thereof - Google Patents
Method for solubilising hesperetin-7-O-glucoside and solubilised complexes thereof Download PDFInfo
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Abstract
According to the method, a certain proportion of hesperetin-7-O-glucoside and a dissolution increasing auxiliary material naringenin-7-O-glucoside are compounded, a special reaction treatment mode is adopted, and the compound is prepared into a dissolution increasing compound with hydrogen bonds and pi-pi bond intermolecular force connection, wherein the hesperetin-7-O-glucoside and the naringenin-7-O-glucoside are subjected to intermolecular force solidification through ordered arrangement, a hydrophilic sugar chain is outwards formed, a hydrophobic aglycone is inwards-oriented and like a gel structure, and the compound has better water solubility, so that the hesperetin-7-O-glucoside is dissolved in water in a high concentration and stable manner and is not separated out, the application range of the hesperetin-7-O-glucoside is widened, and the bioavailability of the hesperetin-7-O-glucoside is improved.
Description
Technical Field
The invention relates to the technical field of a solubilization method of a compound, in particular to a method for solubilizing hesperetin-7-O-glucoside and a solubilization complex thereof.
Background
hesperetin-7-O-glucoside is a monosaccharide glycoside of a dihydroflavone. The component has pharmacological activity: 1) The effect of treating diabetes is achieved by inhibiting intestinal maltase; 2) By inhibiting HMG-CoA reductase, has cholesterol lowering effect; 3) By inhibiting the growth of helicobacter pylori, the composition has the effect of treating diseases such as gastritis, duodenal ulcer and gastric cancer (Lee, Y.—S..Huh, J..Y..Nam, S.—H..Moon, S..K..Lee, S..B.. Enzymatic bioconversion of citrus hesperidin by Aspergillus sojae naringinase: enhanced solubility of hesperetin-7-O-glucoside with in vitro inhibition of human intestinal maltase, HMG-CoA reduction enzyme, and growth of Helicobacter pyr. Food chem.. 2012.135 (4), 2253-2259 and Veldhuyzen van Zanten, S.J..Sherman, P.M.. Helicobacter pylori infection as acause of gastritis, duodenal ul cer, gastric cancer and nonulcer dyspepsia: asystic overview, CMAJ: can. Med. Assoc. J.. 1994.150): 177-185); 4) Has the effect of preventing and treating osteoporosis (Habauzit, V., nielsen, I. -L., gil-Izquierdo, A., trzeciakiewicz, A., morandC., chee, W., barron, D., lebecque, P., davicco, M. -J., williamson, G., offord, E., coxam, V., horcajada, M. -N., increased bioavailability of hesperetin-7-glucoside compared with hesperidin results in more efficient prevention of bone loss in adult ovariectomised rates, br. J, nutr, 2009.102 (07), 976-984).
Structure of hesperetin-7-O-glucoside
Therefore, the hesperetin-7-O-glucoside has good application prospect in the field of medicines. However, the solubility of hesperetin-7-O-glucoside in aqueous solution is only 0.319mg/ml, so that the bioavailability is too low, and the application of the hesperetin-7-O-glucoside in industry is greatly limited. Namely: the indissolvable nature of hesperetin-7-O-glucoside is a major obstacle for its clinical and industrial application. Thus, it is of great practical importance to find a method for increasing the solubilization of hesperetin-7-O-glucoside in aqueous solutions.
At present, only 1 document report about a method for solubilizing a hesperetin-7-O-glucoside component exists in the prior art. The document reports that the use of 10% ethanol as a solvent can increase the solubility of hesperetin-7-O-glucoside to 0.957 mg/ml (Lee, y.—s., huh, j.—y., nam, s.—h., moon, s.—k., lee, s.—b., enzymatic bioconversion of citrus hesperidin by Aspergillus sojae naringinase: enhanced solubility of hesperetin-7-O-glucoside with in vitro inhibition of human intestinal maltase, HMG-CoA reduction, and growth of Helicobacter pyri. Food chem.. 2012.135 (4), 2253-2259). However, the solubility of the compound is still not high, and the use mode and the use range of the finished product of the hesperetin-7-O-glucoside are limited by ethanol contained in the solubilizing solvent.
Therefore, it is necessary to quickly, simply, efficiently and safely solubilize hesperetin-7-O-glucoside in an aqueous solution to obtain a high concentration hesperetin-7-O-glucoside aqueous solution, and to improve the bioavailability of hesperetin-7-O-glucoside.
Disclosure of Invention
The technical purpose of the invention is as follows: the method for quickly, safely and efficiently solubilizing the hesperetin-7-O-glucoside in the aqueous solution is provided to improve the bioavailability of the hesperetin-7-O-glucoside, and the solubilizing compound of the hesperetin-7-O-glucoside is provided to expand the application range of the solubilizing compound and ensure that the solubilizing compound can be stably dissolved when in use.
The invention adopts the technical proposal for realizing the technical purpose that: a method for solubilizing hesperetin-7-O-glucoside, comprising the steps of:
step one, respectively taking main raw material hesperetin-7-O-glucoside and solubilizing auxiliary material naringenin-7-O-glucoside according to the mass ratio of (7:3) - (2:8), and mixing to prepare a mixed material for later use;
step two, mixing the mixed materials prepared in the step one with water according to the proportion of (3-4) g/L, fully and uniformly mixing, and carrying out heating reflux reaction for 1-2h at the temperature of 80-100 ℃ to prepare a reaction product solution for later use;
and thirdly, filtering the reaction product solution prepared in the second step, and sequentially concentrating and drying the obtained filtrate to obtain a solubilizing compound product capable of realizing the solubilization of the hesperetin-7-O-glucoside.
Further, in the second step, the mixing material and water are mixed in at least one of vibration, stirring and ultrasonic treatment.
Further, the ultrasonic treatment time is 10-30 min.
Further, in the second step, the adding ratio of the mixed material to water is 3.33g/L.
Further, in the third step, the concentration mode is at least one of reduced pressure concentration and molecular distillation.
Further, in the third step, the drying mode is at least one of reduced pressure drying, microwave drying, spray drying, normal pressure drying and freeze drying.
A solubility-increasing compound containing hesperetin-7-O-glucoside is formed by compounding hesperetin-7-O-glucoside and naringenin-7-O-glucoside, and the mass ratio of the hesperetin-7-O-glucoside to the naringenin-7-O-glucoside in the solubility-increasing compound is (7:3) - (2:8).
The invention has the beneficial effects that:
1. the method for solubilizing the hesperetin-7-O-glucoside has the advantages of simple steps and convenient operation, and can prepare the hesperetin-7-O-glucoside with low solubility into a solubilizing compound which can realize stable compounding and better dissolution in high concentration in aqueous solution, so as to improve the bioavailability of the hesperetin-7-O-glucoside and expand the application range and medicinal effect of the hesperetin-7-O-glucoside. The method is simple in operation and low in cost, and is suitable for industrial production.
2. According to the dissolution increasing method, the hesperetin-7-O-glucoside and the dissolution increasing auxiliary material naringenin-7-O-glucoside are compounded in a certain proportion, and a special reaction treatment mode is adopted to prepare the dissolution increasing compound with hydrogen bonds and pi-pi bond intermolecular force connection, wherein the hesperetin-7-O-glucoside and the naringenin-7-O-glucoside are orderly arranged among molecules and are solidified by intermolecular force, so that a solubilization compound structure of a similar micelle structure with a hydrophilic sugar chain facing outwards and a hydrophobic aglycone facing inwards is formed, good water solubility is presented, and the hesperetin-7-O-glucoside is dissolved in water in a high concentration and stable manner, so that an application range of hesperetin-7-O-glucoside and a naringenin-7-O-glucoside aqueous solution with high concentration is widened, and the bioavailability of the hesperetin-7-O-glucoside is improved.
3. When the solubilizing compound provided by the invention is used, the high-concentration clarified liquid, namely the hesperetin-7-O-glucoside aqueous solution, can be obtained only by simple oscillation or stirring type mixing with water, and the solubilizing compound is safe and convenient to use and has a good solubilizing effect.
4. According to the method for solubilizing the hesperetin-7-O-glucoside, the third substance naringenin-7-O-glucoside is added into the solubilizing system, so that the solubilization of the hesperetin-7-O-glucoside in an aqueous solution can be realized rapidly and efficiently, and the solubilizing auxiliary material naringenin-7-O-glucoside cannot influence the material characteristics of the hesperetin-7-O-glucoside, so that the solubilizing compound can be more conveniently, widely and safely applied to the fields of foods, medicines, daily chemical industries and the like, and related products of foods, medicines and daily chemical products can be prepared.
Drawings
FIG. 1 is a structural formula of hesperetin-7-O-glucoside;
FIG. 2 is a structural formula of naringenin-7-O-glucoside;
FIG. 3 is a graph showing the dissolution characteristics of hesperetin-7-O-glucoside in an aqueous solution of a solubilizing complex and an aqueous solution of hesperetin-7-O-glucoside (wherein the dotted line represents the concentration of hesperetin-7-O-glucoside in the aqueous solution of the solubilizing complex; and the solid line represents the concentration of hesperetin-7-O-glucoside in the aqueous solution of hesperetin-7-O-glucoside).
Detailed Description
In order that those skilled in the art will better understand the technical solution of the present invention, the present invention will be further described with reference to specific examples and drawings, but the examples are not intended to be limiting.
The experimental methods and the detection methods described in the following examples are all conventional methods unless otherwise specified; the experimental process is carried out under normal temperature and normal pressure unless indicated; the reagents and materials are commercially available unless otherwise specified.
The method for solubilizing the hesperetin-7-O-glucoside comprises the steps of uniformly mixing the hesperetin-7-O-glucoside and a solubilizing auxiliary material naringenin-7-O-glucoside with water according to the mass ratio of (7:3) - (2:8), heating until the mixture is dissolved, filtering, concentrating, and drying to obtain a solubilizing compound product containing the hesperetin-7-O-glucoside and the naringenin-7-O-glucoside. In the solubilization method, a third substance is added, so that a compound is formed by the solubilization auxiliary material and the substance to be solubilized, the solubility of the hesperetin-7-O-glucoside in a medium is increased, and in the solubilization system, the hesperetin-7-O-glucoside can be stably dissolved and is not separated out. The dissolution-increasing compound product can effectively improve the dissolution effect of the hesperetin-7-O-glucoside in the aqueous solution, improve the bioavailability of the hesperetin-7-O-glucoside and enlarge the application range of the hesperetin-7-O-glucoside.
The dissolving method specifically comprises the following steps:
step one, respectively taking main raw material hesperetin-7-O-glucoside and solubilizing auxiliary material naringenin-7-O-glucoside according to the mass ratio of (7:3) - (2:8), and mixing to prepare a mixed material for later use;
mixing the mixed material prepared in the first step with water according to the proportion of (3-4) g/L, preferably 3.33g/L, wherein the mixing mode is oscillation, stirring or ultrasonic treatment, when the ultrasonic treatment is adopted, the treatment time is 10-30 min, after fully and uniformly mixing, heating and refluxing reaction is carried out for 1-2h at the temperature of 80-100 ℃ to prepare a reaction product solution for later use;
and thirdly, filtering the reaction product solution prepared in the second step, and sequentially concentrating and drying the obtained filtrate in at least one of decompression concentration and molecular distillation, wherein the drying mode is at least one of decompression drying, microwave drying, spray drying, normal pressure drying and freeze drying, so as to obtain a solubilizing compound product capable of realizing the solubilization of the hesperetin-7-O-glucoside.
The hesperetin-7-O-glucoside and naringenin-7-O-glucoside solubilizing compound prepared by the invention can be dissolved by adding a proper amount of water through shaking or short-time ultrasonic treatment, and the hesperetin-7-O-glucoside and naringenin-7-O-glucoside cluster polymer has better water solubility, so that the hesperetin-7-O-glucoside and naringenin-7-O-glucoside cluster polymer can be more conveniently and widely applied to the fields of food, medicine, daily chemical industry and the like so as to prepare related products of food, medicine and daily chemical industry.
Example 1
The method for solubilizing the hesperetin-7-O-glucoside comprises the following steps:
taking the hesperetin-7-O-glucoside 700 mg and the naringenin-7-O-glucoside 300 mg, placing the hesperetin-7-O-glucoside and the naringenin-7-O-glucoside into a 500 ml round bottom flask, adding distilled water 300 ml, carrying out ultrasonic treatment for 10 minutes, heating and refluxing for 80 minutes at 100 ℃ after uniformly mixing, filtering the obtained solution, concentrating the obtained filtrate under reduced pressure, and freeze-drying to obtain a solubilizing compound product capable of realizing solubilization of the hesperetin-7-O-glucoside.
Example 2
The method for solubilizing the hesperetin-7-O-glucoside comprises the following steps:
taking 500 mg of hesperetin-7-O-glucoside and 500 mg of naringenin-7-O-glucoside, placing in a 500 ml round bottom flask, adding 300 ml of distilled water, carrying out ultrasonic treatment for 20 minutes, uniformly mixing, heating and refluxing for 100 minutes at 90 ℃, filtering the obtained solution, concentrating the obtained filtrate under reduced pressure, and freeze-drying to obtain a solubilizing compound product capable of realizing solubilization of the hesperetin-7-O-glucoside.
Example 3
The method for solubilizing the hesperetin-7-O-glucoside comprises the following steps:
taking hesperetin-7-O-glucoside 200 mg and naringenin-7-O-glucoside 800 mg, placing into a 500 ml round bottom flask, adding distilled water 300 ml, carrying out ultrasonic treatment for 30 minutes, uniformly mixing, heating and refluxing at 80 ℃ for 60 minutes, filtering the obtained solution, concentrating the obtained filtrate under reduced pressure, and drying under reduced pressure to obtain a solubilizing compound product capable of realizing solubilization of hesperetin-7-O-glucoside.
Example 4
The method for solubilizing the hesperetin-7-O-glucoside comprises the following steps:
taking 600 mg of hesperetin-7-O-glucoside and 400 mg of naringenin-7-O-glucoside, placing into a 500 ml round bottom flask, adding 300 ml of distilled water, stirring and mixing for 30 minutes, heating and refluxing for 120 minutes at 80 ℃ after uniform mixing, filtering the obtained solution, molecular distilling the obtained filtrate, and spray drying to obtain a solubilizing compound product capable of realizing solubilization of hesperetin-7-O-glucoside.
Test verification
Investigation of the solubilization Effect of hesperetin-7-O-glucoside in the solubilization Complex product:
(1) Preparation of sample solution
Taking the solubilizing compound 100 mg prepared in the embodiment 1, adding distilled water 10ml, and shaking to obtain a sample solution. The content of hesperetin-7-O-glucoside in the sample was measured by high performance liquid chromatography.
(2) Preparation of standard substance solution
Taking 2.0mg of hesperetin-7-O-glucoside standard substance, placing into a 10ml volumetric flask, adding a proper amount of methanol, performing ultrasonic dissolution, fixing the volume to a scale by using the methanol, filtering by using a 0.45 mu m microporous filter membrane, and taking a subsequent filtrate to obtain a standard substance solution.
(3) Preparation of sample solution
A. And (3) taking 50 mu L of the sample solution obtained in the step (1), placing the sample solution into a 10ml volumetric flask, adding a proper amount of methanol, shaking for dissolving, fixing the volume to a scale by using the methanol, filtering by using a 0.45 mu m microporous filter membrane, and taking a subsequent filtrate to obtain the sample solution I.
B. Taking hesperetin-7-O-glucoside 50 mg, placing into a 50ml volumetric flask, adding water to scale, weighing, performing ultrasonic treatment for 30min, supplementing to original weight, shaking uniformly (the solution is in a turbid state and is in a supersaturated state), filtering with a 0.45 μm microporous filter membrane, and collecting the subsequent filtrate to obtain a sample solution II.
(4) Conditions of liquid chromatography
Chromatographic column Thermo C18 chromatographic column (4.6 mm X250 mm,5 μm); mobile phase: methanol-3% phosphoric acid in water (20:80); flow rate: 1.0 mL.min -1 The method comprises the steps of carrying out a first treatment on the surface of the Detection wavelength: 280nm; sample injection amount: 10.0 Mu L.
(5) Measurement of samples
And (3) precisely sucking 10 mu L of each of the standard solution, the test solution I and the test solution II prepared in the step (2), injecting into a liquid chromatograph, and analyzing according to chromatographic conditions. And calculating the content of the hesperetin-7-O-glucoside by adopting an external standard one-point method.
(6) Results of
The measurement is as follows: the concentration of hesperetin-7-O-glucoside in the aqueous solution of the solubilization complex in example 1 was 6.8.+ -. 0.25 mg/ml, and the saturated solubility in the aqueous solution of hesperetin-7-O-glucoside was 0.45.+ -. 0.06 mg/ml.
Stability investigation of hesperetin-7-O-glucoside in solubilizing complex product:
1. preparation of sample solutions
Taking the solubilizing compound 100 mg prepared in the embodiment 1, adding distilled water 10ml, and shaking to obtain a sample solution.
2. Preparation of standard substance solution
Taking 2.0mg of hesperetin-7-O-glucoside standard substance, placing into a 10ml volumetric flask, adding a proper amount of methanol, performing ultrasonic dissolution, fixing the volume to a scale by using the methanol, filtering by using a 0.45 mu m microporous filter membrane, and taking a subsequent filtrate to obtain a standard substance solution.
3. Preparation of test sample solution
A. And (2) sampling 50 mu L of the sample solution in the step (1) every 2 hours after the preparation, placing the sample solution in a 10ml volumetric flask, adding a proper amount of methanol, shaking for dissolving, fixing the volume to a scale by using the methanol, filtering by using a microporous filter membrane with the size of 0.45 mu m, and taking a subsequent filtrate to obtain the sample solution III.
B. Taking hesperetin-7-O-glucoside 50 mg, placing into a 50ml volumetric flask, adding water to scale, weighing, performing ultrasonic treatment for 30min, supplementing to original weight, and shaking uniformly (at this time, the solution is in a turbid state and is in a supersaturated state) to obtain hesperetin-7-O-glucoside aqueous solution. And (3) sampling 1mL of the hesperetin-7-O-glucoside water solution every 2 hours after the preparation of the hesperetin-7-O-glucoside water solution is finished, filtering the solution by using a 0.45 mu m microporous filter membrane, and taking a subsequent filtrate to obtain the sample solution IV.
4. Conditions of liquid chromatography
Chromatographic column Thermo C18 chromatographic column (4.6 mm X250 mm,5 μm); mobile phase: methanol-3% phosphoric acid in water (20:80); flow rate: 1.0 mL.min -1 The method comprises the steps of carrying out a first treatment on the surface of the Detection wavelength: 280nm; sample injection amount: 10.0 Mu L.
5. Sample measurement
And (3) precisely sucking the standard substance solution, each sample solution III and each sample solution IV prepared in the step (2), respectively, injecting 10 mu L of each sample solution into a liquid chromatograph, and analyzing according to chromatographic conditions. And calculating the content of the hesperetin-7-O-glucoside by adopting an external standard one-point method.
6. Results
The measurement is as follows: the concentration of hesperetin-7-O-glucoside in the aqueous solution of the solubilization complex of example 1 was stable for 12 hours as measured, during which time the solution system remained transparent without precipitate formation. The saturated concentration of the aqueous solution of hesperetin-7-O-glucoside was stable within 12 hours. The results are shown in FIG. 3.
The test results show that the solubility-increasing compound can greatly improve the solubility of the hesperetin-7-O-glucoside in the aqueous solution, and the hesperetin-7-O-glucoside can stably exist in the aqueous solution for a long time.
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.
Claims (6)
1. A method for solubilising hesperetin-7-O-glucoside, characterized in that it comprises the steps of:
step one, respectively taking main raw material hesperetin-7-O-glucoside and solubilizing auxiliary material naringenin-7-O-glucoside according to the mass ratio of (7:3) - (2:8), and mixing to prepare a mixed material for later use;
step two, mixing the mixed materials prepared in the step one with water according to the proportion of (3-4) g/L, fully and uniformly mixing, and carrying out heating reflux reaction for 1-2h at the temperature of 80-100 ℃ to prepare a reaction product solution for later use;
and thirdly, filtering the reaction product solution prepared in the second step, and sequentially concentrating and drying the obtained filtrate to obtain a solubilizing compound product capable of realizing the solubilization of the hesperetin-7-O-glucoside.
2. The method for solubilizing hesperetin-7-O-glucoside according to claim 1, wherein: in the second step, the mode of mixing the ingredients with water is at least one of vibration, stirring and ultrasonic treatment.
3. The method for solubilizing hesperetin-7-O-glucoside according to claim 2, characterized in that: the ultrasonic treatment time is 10-30 min.
4. The method for solubilizing hesperetin-7-O-glucoside according to claim 1, wherein: in the second step, the adding ratio of the mixed material and water is 3.33g/L.
5. The method for solubilizing hesperetin-7-O-glucoside according to claim 1, wherein: in the third step, the concentration mode is at least one of reduced pressure concentration and molecular distillation.
6. The method for solubilizing hesperetin-7-O-glucoside according to claim 1, wherein: in the third step, the drying mode is at least one of reduced pressure drying, microwave drying, spray drying, normal pressure drying and freeze drying.
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| CN1816537A (en) * | 2003-07-02 | 2006-08-09 | 不二制油株式会社 | Flavonoid solubilizing agent and method of solubilizing flavonoid |
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| JP2016190803A (en) * | 2015-03-31 | 2016-11-10 | 公立大学法人大阪府立大学 | Solubilizing agents |
| CN107595867A (en) * | 2017-08-24 | 2018-01-19 | 吉林大学 | A kind of method for preparing naringenin, hesperetin and its single glucoside mixture |
| CN112142808A (en) * | 2020-09-15 | 2020-12-29 | 河南科技大学 | Neohesperidin-naringin cluster polymer and preparation method and application thereof |
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| 姜华等.新橙皮苷对柚皮苷增溶作用及其机制的初步考.《中国药学杂志》.2021,第56卷(第6期),第487页右栏部分. * |
| 糖苷酶对橙皮苷和柚皮苷的酶解作用研究;郑美瑜;陆胜民;陈剑兵;夏其乐;;中国食品学报(第04期);第141-146页 * |
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