CN112390837B - Method for extracting narirutin from immature bitter orange - Google Patents
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Abstract
The invention discloses a preparation method for extracting narirutin from immature bitter orange serving as a raw material. Selecting fructus Aurantii Immaturus material with diameter of 1.5cm or less. Extracting with alkaline methanol or ethanol, filtering the extractive solution to adjust pH, concentrating, and filtering. And (3) enabling the filtrate to pass through a macroporous resin column, separating inorganic compounds such as salt and the like, and further separating by using a cation resin column to obtain a narirutin crude product and a synephrine byproduct. Heating the crude product of the narirutin in water to dissolve, and separating by a polyamide column. The high-content narirutin product can be obtained.
Description
Technical Field
The invention belongs to the field of plant extraction, and particularly discloses a method for extracting narirutin from immature bitter oranges.
Background
Immature bitter orange, named as traditional Chinese medicine. Is dried young fruit of Citrus aurantium L. And its cultivar or Citrus sinensis Osbeck of Rutaceae. Immature bitter orange is usually in the form of spherical granules, and commercially available immature bitter orange is usually in the form of whole granules and sliced granules. The diameter is 0.5-2.5cm, the epicarp is dark green or dark brown green, has granular protrusions and wrinkles, and has obvious style vestige or fruit stalk mark. The pericarp in the section is slightly raised, yellow white or yellow brown, the thickness is 0.3-1.2 cm, 1-2 rows of oil chambers are arranged at the edge, and the pulp sac is brown. Is hard and hard. Fragrant smell, bitter and slightly sour taste. The sliced immature bitter orange has longer fruit development time and lower content of effective components relative to the whole immature bitter orange, so the method does not adopt the sliced immature bitter orange as a raw material.
Immature bitter orange contains a plurality of components with economic value, wherein hesperidin and synephrine are two main components. Hesperidin (glycoside), a flavonoid substance widely present in citrus fruits, has a chemical structure of dihydroflavonoxyglycoside and is weakly acidic. Hesperidin has effects of maintaining osmotic pressure, enhancing capillary toughness, shortening bleeding time, reducing cholesterol, etc., is clinically used for auxiliary treatment of cardiovascular system diseases, can be used for cultivating various medicines for preventing arteriosclerosis and myocardial infarction, and is one of main raw materials of adult medicine "Maitong". In application, hesperidin can be used for synthesizing diosmin. Diosmin is a drug for enhancing venous tonicity and a vascular protective agent. First, for the venous system, the product is passed through a prolongation. The time during which epinephrine acts on the vein wall to cause contraction, thereby increasing the venous tone; for microcirculation system, the product can reduce capillary permeability and enhance resistance; for lymphatic system, the product can increase lymphatic drainage speed and lymphatic vessel contraction, improve lymphatic return, and relieve edema.
The pharmacological action of synephrine mainly shows that the synephrine is an adrenoreceptor stimulant and has certain excitation action on cardiac receptors; can contract blood vessels, raise blood pressure, dilate bronchus and trachea; the synephrine also has certain weight-losing and anti-depression effects, is mainly used for treating bronchial asthma, hypotension collapse, shock postural hypotension indigestion and gastroptosis, and the like in clinic by using chemical book, is a pure natural stimulant, has no side effect or positive reaction, and is widely used in the industries of medicines, foods, beverages and the like.
In addition to hesperidin and synephrine, the immature bitter orange also contains narirutin which has the activities of resisting inflammation, virus, cancer, mutation, allergy, ulcer, pain and blood pressure, can reduce blood cholesterol, reduce the formation of thrombus, improve local microcirculation and nutrition supply and can be used for producing medicaments for preventing and treating cardiovascular and cerebrovascular diseases. In the existing immature bitter orange extraction process, most enterprises only extract and develop hesperidin, but hardly extract synephrine and narirutin, thereby causing great waste.
Disclosure of Invention
In order to solve the problems, the invention provides a method for comprehensively developing an extract of immature bitter orange, which can extract synephrine and narirutin with high concentration besides hesperidin.
The technical scheme of the invention is as follows:
a method for extracting narirutin from immature bitter orange comprises the following steps:
selecting immature bitter orange raw materials with the diameter of less than 1.5cm, crushing, then selecting alkaline methanol or ethanol solution with proper concentration, extracting at a certain temperature, adjusting the pH value of the extracting solution to a certain range, concentrating, filtering to remove hesperidin crystals, then passing the filtrate through a macroporous resin column, separating salt from the filtrate, eluting by using ethanol water solution, concentrating the eluent to one fourth of the original volume, loading the eluent into a cation chromatographic column, collecting the effluent, concentrating and drying to obtain a crude product of the narirutin; dissolving the crude product of the narirutin in hot water at a certain temperature, filtering, cooling the filtrate, adding ethanol for regulating and dissolving, passing through a polyamide column, and obtaining the high-content narirutin by a gradient elution method and a mobile phone gradient elution method.
Preferably, the method for extracting the narirutin from the immature bitter orange comprises the following steps:
(1) Pretreatment of immature bitter orange raw materials: soaking fructus Aurantii Immaturus in water, pulverizing fructus Aurantii Immaturus into incomplete granules, and washing with a small amount of water;
(2) And (3) alkaline alcohol extraction: adding an alkaline alcohol solution into the raw materials obtained in the step (1), stirring and extracting or performing ultrasonic countercurrent extraction, adjusting the pH of the extracting solution to a certain range, concentrating the extracting solution to crystallize, and filtering.
(3) Adding a certain amount of water into the filtrate obtained in the step (2) for dilution, putting the filtrate into a macroporous resin column, eluting with water, and removing the water eluent. Then eluting with ethanol solution, concentrating the ethanol solution eluent to one fourth of the original volume, and adding water to dilute the solution;
(4) Passing the solution obtained in the step (3) through a cation resin column, collecting effluent liquid, concentrating and drying, collecting ammonia water eluent, and concentrating to obtain a synephrine byproduct with high content;
(5) Adding the concentrated powder of the effluent obtained in the step (4) into hot water at a certain temperature, dissolving, filtering, cooling the filtrate, adding a small amount of ethanol solution, loading into a polyamide resin column, performing gradient elution by using ethanol, collecting eluent with the concentration of 60-70% of ethanol, concentrating and drying to obtain a high-content narirutin product;
Preferably, the pretreatment conditions of the immature bitter orange raw material comprise: selecting fructus Aurantii Immaturus raw material (preferably 1.2 cm) with diameter less than 1.5cm, soaking fructus Aurantii Immaturus in water to completely soak, pulverizing fructus Aurantii Immaturus into granules, and washing with 5BV water.
Preferably: in the alkaline solution extraction step: the alkaline alcohol solution is 70-80% methanol or ethanol water (preferably 80% methanol solution) added with 1% sodium hydroxide (w/v). The extraction time with stirring is 2 hours, and the volume of the solution is 12 to 15 times of the volume of the raw material (hereinafter, the BV is equivalent to several times of the volume of the raw material, for example, 3BV represents a solution of three times of the volume of the raw material) (preferably 15 BV). The ultrasonic countercurrent extraction flow rate is 8-10BV/h (preferably 10 BV), and the ultrasonic power is 45kHz. The adjusting range of the pH value is 5.5-6.0 (preferably 5.70) (multiple experiments determine that the narirutin is difficult to precipitate and the hesperidin is more precipitated in the range). The concentration condition of the filtrate is 65-75 ℃ (preferably 70 ℃), and the pressure is-0.06 MPa to-0.08 MPa (preferably-0.08 MPa). After concentrating to one fourth of the original volume, standing for 3 hours and filtering.
Preferably, in the step (3): the volume of water added is 3-5BV (relative to the volume of the ethanol concentrate) (preferably 5 BV), and the macroporous resin column is selected from the commonly used D101 macroporous resins. The flow rate of the upper column is 1-2BV per hour (relative to the volume of the macroporous resin column) (preferably 1.5 BV/h), the flow rate of water elution is 1-1.5BV/h (preferably 1 BV/h), the washing times of water is 8-10BV (preferably 10 BV), the flow rate of ethanol elution is 0.5-1BV/h (preferably 1 BV/h), the washing times of ethanol elution is 10-12BV (preferably 12 BV), and the concentration of the ethanol solution is 80-90% (preferably 80%). Concentrating the ethanol eluate under 65-75 deg.C (preferably 70 deg.C) under-0.06 MPa to-0.08 MPa (preferably-0.08 MPa), and adding 8-10BV water to dilute the solution (preferably 10 BV) when concentrating to one fourth of the original volume.
Preferably, in the step (4), the cation resin column is LS-T28, the column loading speed is 1-2BV/h (preferably 1.5 BV/h), the water washing speed is 1-1.5BV (preferably 1.5 BV/h), the water washing times are 10-15BV (preferably 12 BV), and the elution flow rate is 0.5-1BV (preferably 0.8 BV/h). The eluent is 5% ammonia water solution, and the eluting time is 10-12BV (preferably 12 BV). The concentration condition of the eluent is 75-80 deg.C (preferably 80 deg.C), and the pressure is-0.06 MPa to-0.08 MPa (preferably-0.08 MPa). Concentrating, and vacuum drying to obtain synephrine byproduct.
Preferably: in the step (5): the concentration condition of the extract in the last step is 75-80 deg.C (preferably 80 deg.C), and the pressure is-0.06 MPa to-0.08 MPa (preferably-0.08 MPa). Concentrating, drying, adding 80-90 deg.C hot water (preferably 90 deg.C), adding 6-8BV (preferably 6 BV), dissolving narirutin, filtering, adding high concentration ethanol solution into the filtrate to adjust ethanol concentration to 20-30% (preferably 25%), loading into polyamide resin column at flow rate of 1-1.5BV/h (preferably 1.5 BV/h), eluting with 60-70% ethanol (preferably 70%), eluting with volume of 10-15BV (preferably 10 BV), eluting with flow rate of 1.5-2BV/h (preferably 1.5 BV/h), concentrating the eluate at 75-80 deg.C and pressure of-0.06 MPa to-0.08 MPa (preferably-0.08 MPa); concentrating, and vacuum drying to obtain high-content narirutin product.
Compared with the prior art, the invention has the beneficial effects that:
the method aims at solving the problems that most enterprises only extract and develop the hesperidin in the existing immature bitter orange extraction process, a small part of enterprises can extract synephrine, but the narirutin is hardly extracted; the narirutin has great development space as a product with potential medical value; the method focuses on the development of the narirutin, can ensure that the hesperidin can be completely extracted while obtaining high-content narirutin, and can also obtain relatively pure synephrine; therefore, the extraction method disclosed by the invention greatly increases the utilization rate of the raw materials, so that the whole immature bitter orange product line can have higher risk resistance, and the product competitiveness of enterprises is enhanced.
The concrete advantages include:
1. the separation effect is obvious, and the utilization rate of raw materials is high. The method uses the immature bitter oranges to extract the narirutin in the immature bitter oranges, can obtain two effective components of hesperidin and synephrine while extracting the narirutin, and can greatly strengthen the immature bitter orange product line.
2. The production process is green and environment-friendly, and all the used solvents have small pollution to the environment. In the invention, no obvious harmful substance is generated, the environmental pollution is less, and most of the solution can be safely and cleanly treated.
3. Although the production cost is higher than that of only extracting hesperidin, the whole benefit is far higher than that of only extracting hesperidin due to the fact that the content of immature bitter orange is completely extracted, meanwhile, the site utilization rate is high, and the production cost is reduced on the other hand.
Drawings
FIG. 1 is a process flow diagram of the present invention.
FIG. 2 is an HPLC profile of the synephrine standard of example 1;
FIG. 3 is an HPLC chromatogram of the synephrine prepared in example 1;
FIG. 4 is an HPLC profile of the narirutin standard of example 1;
FIG. 5 is a narirutin HPLC profile prepared in example 1.
Detailed Description
The technical solution of the present invention will be further described in detail with reference to specific embodiments. The following examples are merely illustrative and explanatory of the present invention and should not be construed as limiting the scope of the invention. All the technologies realized based on the above-mentioned contents of the present invention are covered in the protection scope of the present invention.
Unless otherwise indicated, the raw materials and reagents used in the following examples are all commercially available products or can be prepared by known methods.
The overall flow is shown in fig. 1, and specifically as follows:
1: pretreatment of immature bitter orange raw materials: soaking fructus Aurantii Immaturus in water, pulverizing fructus Aurantii Immaturus into incomplete granules, and washing with a small amount of water;
Preferably, the pretreatment conditions of the immature bitter orange raw material comprise: selecting fructus Aurantii Immaturus material (preferably 1.2 cm) with diameter less than 1.5cm, soaking fructus Aurantii Immaturus in water to completely soak, pulverizing fructus Aurantii Immaturus into granules, and washing with 5BV water.
2: and (3) extracting with alkaline alcohol: adding an alkaline alcohol solution into the raw materials obtained in the step (1), stirring and extracting or performing ultrasonic countercurrent extraction, adjusting the pH of the extracting solution to a certain range, concentrating the extracting solution to crystallize, and filtering.
Preferably: the alkaline solution extraction step comprises: the alkaline alcohol solution is 70-80% methanol or ethanol water (preferably 80% methanol solution) added with 1% sodium hydroxide (w/v). The extraction time with stirring is 2 hours, and the volume of the solution is 12 to 15 times of the volume of the raw material (hereinafter, the BV is equivalent to several times of the volume of the raw material, for example, 3BV represents a solution of three times of the volume of the raw material) (preferably 15 BV). The ultrasonic countercurrent extraction flow rate is 8-10BV/h (preferably 10 BV), and the ultrasonic power is 45kHz. The adjusting range of the pH value is 5.5-6.0 (preferably 5.70) (the fact that the narirutin is difficult to separate out and the hesperidin is more separated out in the range is determined through a plurality of experiments). The concentration condition of the filtrate is 65-75 ℃ (preferably 70 ℃), and the pressure is-0.06 MPa to-0.08 MPa (preferably-0.08 MPa). After concentrating to one fourth of the original volume, the mixture was left for 3 hours and then filtered.
3: and (3) adding a certain amount of water into the filtrate obtained in the step (2) for dilution, putting the filtrate into a macroporous resin column, eluting the filtrate with water, and removing the water eluent. Then eluting with ethanol solution, concentrating the ethanol solution eluent to one fourth of the original volume, and adding water to dilute the solution;
preferably, in the step (3): the volume of water added is 3-5BV (relative to the volume of the ethanol concentrate) (preferably 5 BV), and the macroporous resin column is selected from the commonly used D101 macroporous resins. The flow rate of the upper column is 1-2BV per hour (relative to the volume of the macroporous resin column) (preferably 1.5 BV/h), the flow rate of water elution is 1-1.5BV/h (preferably 1 BV/h), the washing times of water is 8-10BV (preferably 10 BV), the flow rate of ethanol elution is 0.5-1BV/h (preferably 1 BV/h), the washing times of ethanol elution is 10-12BV (preferably 12 BV), and the concentration of the ethanol solution is 80-90% (preferably 80%). Concentrating the ethanol eluate under 65-75 deg.C (preferably 70 deg.C) under-0.06 MPa to-0.08 MPa (preferably-0.08 MPa), and adding 8-10BV water to dilute the solution (preferably 10 BV) when concentrating to one fourth of the original volume.
4: passing the solution obtained in the step (3) through a cation resin column, collecting effluent, concentrating and drying the water washing solution, collecting ammonia water eluate, and concentrating to obtain a synephrine byproduct with high content;
Preferably, in the step (4), the cation resin column is LS-T28, the column loading speed is 1-2BV/h (preferably 1.5 BV/h), the water washing speed is 1-1.5BV (preferably 1.5 BV/h), the water washing times are 10-15BV (preferably 12 BV), and the elution flow rate is 0.5-1BV (preferably 0.8 BV/h). The eluent is 5% ammonia water solution, and the eluting time is 10-12BV (preferably 12 BV). The concentration condition of the eluent is 75-80 deg.C (preferably 80 deg.C), and the pressure is-0.06 MPa to-0.08 MPa (preferably-0.08 MPa). Concentrating, and vacuum drying to obtain synephrine byproduct.
5: adding the concentrated powder of the effluent liquid obtained in the step (4) into hot water at a certain temperature, dissolving, filtering, cooling the filtrate, adding a small amount of ethanol solution, loading into a polyamide resin column, performing gradient elution by using ethanol, collecting eluent with the concentration of 60-70% of ethanol, concentrating and drying to obtain a narirutin product with high content;
preferably: in the step (5): the concentration condition of the extract in the last step is 75-80 deg.C (preferably 80 deg.C), and the pressure is-0.06 MPa to-0.08 MPa (preferably-0.08 MPa). Concentrating, drying, adding 80-90 deg.C hot water (preferably 90 deg.C), adding 6-8BV (preferably 6 BV), dissolving narirutin, filtering, adding high concentration ethanol solution into the filtrate to adjust ethanol concentration to 20-30% (preferably 25%), loading into polyamide resin column at flow rate of 1-1.5BV/h (preferably 1.5 BV/h), eluting with 60-70% ethanol (preferably 70%), eluting with volume of 10-15BV (preferably 10 BV), eluting with flow rate of 1.5-2BV/h (preferably 1.5 BV/h), concentrating the eluate at 75-80 deg.C (preferably 80 deg.C) and pressure of-0.06 MPa to-0.08 MPa (preferably-0.08 MPa). Concentrating, and vacuum drying to obtain high-content narirutin product.
Example 1
The specific process flow for comprehensively preparing the extract of immature bitter orange serving as a raw material is as follows
The raw material sources are as follows: the content of narirutin in immature bitter orange produced by Jiangxi Jian is 1.37%, the content of hesperidin is 23.45%, and the content of synephrine is 0.92% through HPLC detection.
(1) Pretreatment of immature bitter orange
Selecting 100kg of immature bitter orange raw material with the diameter less than 1.5cm, adding water, soaking overnight to completely soak the immature bitter orange raw material, crushing the immature bitter orange raw material into particles, and washing the raw material with 500kg of water.
(2) Extraction with aqueous alkali
Adding the raw material obtained in the step (1) into an extraction tank filled with 1500kg of 1% sodium hydroxide 80% methanol solution, stirring and extracting for 2h, and filtering. Adjusting the pH of the filtrate to 5.70, adding into a concentration tank, adjusting the concentration temperature to 70 deg.C, and controlling the pressure to-0.08 MPa. Concentrating until about 400kg of hesperidin remains, transferring into a crystallizing tank, standing for 3 hr, filtering, and crystallizing to obtain hesperidin product.
(3) Separation with macroporous resin
Diluting the filtrate obtained in the previous step with 1200kg of water, and introducing into a macroporous resin column with model D101, diameter of 30cm, height of 3m, and column volume of 0.21m 3 Total 10, total column volume 2.1m 3 The flow rate of the upper column is controlled to be 3m 3 H, the water washing flow rate is controlled to be 3m 3 The washing amount is 2400kg water, and the ethanol elution flow rate is controlled at 2m 3 And/h, controlling the amount of ethanol elution to be 2400kg, controlling the ethanol concentration to be 80%, after the elution is finished, concentrating the ethanol eluent, controlling the concentration temperature to be 70 ℃, controlling the pressure to be-0.08 MPa, concentrating to be one fourth of the source problem set, and adding 6000kg of water diluted solution when the concentration is about 600 kg.
(4) Separation by cation resin column
Adding the diluted solution into a cationic resin column (LS-T28, single column diameter of 30cm, height of 3m, 5 groups in total), total column volume of 1m3, and column loading speed of 1.5m 3 H, the flow rate of water washing is controlled to be 1.5m 3 The water washing amount is 1200kg per hour, and the water washing liquid and effluent liquid are collected. Eluting with 5% ammonia water at 0.8m 3 H, elution volume 1200kg. Concentrating the eluate at 80 deg.C under-0.08 MPa, and vacuum drying to obtain synephrine byproduct.
(5) Separation on polyamide resin column
Mixing the effluent obtained from the last step of cation resin with water, concentrating at 80 deg.C under-0.08 MPa, concentrating, drying, adding 6kg of 90 deg.C hot water, slightly stirring, filtering, adding 2kg of ethanol into the filtrate to adjust ethanol concentration to 25%, loading into polyamide resin column with polyamide mesh number of 100-150 mesh, diameter of 10cm, column height of 80cm, 2 groups, total column volume of 12.6L, column flow rate of 18L/h, ethanol eluate concentration of 70%, elution flow rate of 18L/h, and elution solution of 120kg. Collecting eluate, concentrating at 80 deg.C under-0.08 MPa, and concentrating and drying to obtain high-content narirutin product.
(6) Results
After the implementation of the process, three products of narirutin, hesperidin and synephrine are obtained, (wherein the figure 2 is an HPLC (high performance liquid chromatography) map of a synephrine standard substance, and the figure 4 is an HPLC map of the narirutin standard substance) to obtain 1.26kg of the narirutin, and the content of the narirutin is determined by an HPLC method, as shown in the figure 5, the content of the narirutin reaches 98.20%, the total yield of the narirutin is 90.13%, which indicates that the process has a good extraction effect on the narirutin. Wherein 23.28kg of hesperidin is obtained, the content is 91.20%, the total yield of hesperidin is 90.53%, and the method has good extraction effect on hesperidin and is obviously higher than other hesperidin extraction methods. A total of 1.76kg of synephrine was obtained, as shown in FIG. 3, at a content of 45.12% and a synephrine yield of 86.31%, which is high relative to the easily degradable nature of synephrine.
The foregoing is only a preferred embodiment of the present invention. However, the present invention is not limited to the above embodiment. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (1)
1. A method for extracting narirutin from immature bitter oranges is characterized by comprising the following steps:
(1) Pretreatment of immature bitter orange raw materials: selecting immature bitter orange raw materials with the diameter less than 1.5cm, adding water to soak the immature bitter oranges completely for grinding, grinding the immature bitter oranges into granules, and washing the raw materials with 5BV of water;
(2) And (3) alkaline alcohol extraction: adding an alkaline alcohol solution into the raw material obtained in the step (1), stirring and extracting or performing ultrasonic countercurrent extraction, adjusting the pH value of the extracting solution to a certain range, concentrating the extracting solution to crystallize, and filtering the precipitated crystals, namely hesperidin crystals;
(3) Adding a certain amount of water into the filtrate obtained in the step (2) for dilution, putting the filtrate into a macroporous resin column, eluting with water, and removing water eluent; then eluting with ethanol solution, concentrating the ethanol solution eluent to one fourth of the original volume, and adding water to dilute the solution;
(4) Passing the solution obtained in the step (3) through a cation resin column, washing with water, collecting effluent, concentrating and drying, eluting with ammonia water eluent, collecting ammonia water eluent, and concentrating to obtain a synephrine byproduct;
(5) Adding the concentrated powder of the effluent obtained in the step (4) into hot water at a certain temperature, dissolving, filtering, cooling the filtrate, adding a small amount of ethanol solution, loading into a polyamide resin column, performing gradient elution with ethanol, collecting the eluent with the ethanol concentration of 60-70%, concentrating and drying to obtain a narirutin product;
In the step (2): the alkaline alcohol solution is 70-80% methanol or ethanol water solution added with 1% sodium hydroxide in w/v; the stirring extraction time is 2 hours, and the volume of the solution is 12-15 times of that of the raw materials; the ultrasonic countercurrent extraction flow rate is 8-10BV/h, and the ultrasonic power is 45kHz; the adjusting range of the pH value is 5.5-6.0; concentrating the filtrate at 65-75 deg.C under-0.06 MPa to-0.08 MPa; concentrating to one fourth of the original volume, standing for 3 hours, and filtering;
in the step (3): the volume of the added water is 3-5BV, and the macroporous resin column is D101 macroporous resin; the flow rate of column loading is 1-2BV/h, the water elution flow rate is 1-1.5BV/h, the washing times of water is 8-10BV, the ethanol elution flow rate is 0.5-1BV/h, the washing times of ethanol is 10-12BV, and the concentration of ethanol solution is 80-90%; concentrating the ethanol eluate under the conditions of 65-75 deg.C and-0.06 MPa-0.08 MPa to one-fourth of the original volume, and adding 8-10BV water to dilute the solution;
in the step (4): the cation resin column is selected from LS-T28 cation resin column, the column loading speed is 1-2BV/h, the water washing speed is 1-1.5BV/h, and the water washing time is 10-15BV; the flow rate of ammonia water elution is 0.5-1BV/h, the ammonia water eluent is 5% ammonia water solution, and the elution time of the ammonia water is 10-12BV; the concentration condition of the ammonia water eluent is 75-80 ℃, and the pressure is-0.06 MPa to-0.08 MPa; concentrating, and vacuum drying to obtain synephrine byproduct;
In the step (5): the concentration condition of the effluent liquid in the last step is 75-80 ℃, and the pressure is-0.06 MPa to-0.08 MPa; concentrating, drying, adding 80-90 deg.C hot water to dissolve narirutin, filtering, and adjusting the filtrate with high concentration ethanol solution to final ethanol concentration of 20-30%; loading into polyamide resin column, eluting with 60-70% ethanol at flow rate of 1.5-1.5 BV/h and 10-15BV times, concentrating the eluate at 75-80 deg.C under pressure of-0.06 MPa to-0.08 MPa; concentrating, and vacuum drying to obtain narirutin product.
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| US20100159100A1 (en) * | 2008-12-19 | 2010-06-24 | Olivier Buysschaert | Flavonoid-rich citrus extract and compositions thereof |
| CN102106918B (en) * | 2011-02-22 | 2012-03-28 | 中国中医科学院中医基础理论研究所 | Method for simultaneously preparing volatile oil, total flavones and total alkaloids from immature bitter oranges |
| CN106220698A (en) * | 2016-07-19 | 2016-12-14 | 江西海富生物工程有限公司 | A kind of method of separating high-purity Hesperidin, neohesperidin, naringin and Neosynephrine from Fructus Aurantii Immaturus |
| CN110423258B (en) * | 2019-09-02 | 2021-06-22 | 成都蜀西制药有限公司 | Method for simultaneously extracting hesperidin, synephrine and polymethoxylated flavone from immature bitter oranges |
| CN111150765B (en) * | 2020-01-17 | 2021-12-24 | 华南农业大学 | Fingered citron flavone extract and separation and purification method thereof |
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