CN112047846A - Method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using ultrasonic-assisted aqueous two-phase system - Google Patents
Method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using ultrasonic-assisted aqueous two-phase system Download PDFInfo
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Abstract
The invention provides a method for extracting synephrine, naringin and neohesperidin in immature bitter oranges by an ultrasonic-assisted aqueous two-phase system, which comprises the steps of crushing and sieving dried immature bitter oranges to obtain immature bitter orange powder; mixing the immature bitter orange powder and the ethanol/inorganic salt aqueous two-phase system according to the mass ratio of the ethanol/inorganic salt aqueous two-phase system to the immature bitter orange powder of (10-60): 1, carrying out ultrasonic extraction at 20-70 ℃ for 10-60 min, centrifuging, collecting an upper phase, and removing solid medicine residues to obtain an extracting solution containing synephrine, naringin and neohesperidin. The method can effectively improve the extraction rate and the extraction efficiency of synephrine, naringin and neohesperidin in the immature bitter orange, and has the advantages of simple extraction process, short extraction time, easy recycling of organic solvent and mild extraction conditions.
Description
Technical Field
The invention belongs to the field of extraction of active ingredients of medicinal plants, and relates to a method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using an ultrasonic-assisted aqueous two-phase system.
Background
The fructus Aurantii Immaturus is Rutaceae plant Citrus aurantium L. and its cultivar or dried young fruit of Citrus sinensis Osbeck. Zhi Shi prefers warm and moist climate and is mainly produced in Sichuan, Jiangxi, Fujian and Jiangsu provinces. Hard texture, fragrant smell, bitter taste, slight acidity and slight cold nature, enter spleen and stomach channels, have the functions of breaking qi and removing food retention, reducing phlegm and dispersing mass, and are used for stagnation and stagnation, mass and distending pain, diarrhea and diarrhea, constipation, phlegm stagnation and qi obstruction, thoracic obstruction, chest stagnation and viscera prolapse. The fructus Aurantii Immaturus contains flavone, alkaloid and volatile oil as main ingredients, and has effects of promoting gastrointestinal motility, resisting cancer, oxidation and bacteria, resisting inflammation, tonifying heart, increasing blood pressure and reducing weight.
Synephrine (synephrine) is a main alkaloid in immature bitter oranges, has the effects of improving metabolism, oxidizing fat and losing weight, can also enhance cardiac blood output and improve left ventricular pressure and arterial blood pressure, and is widely applied to the fields of medicines, foods and the like. Naringin and neohesperidin are two main flavonoid components in immature bitter orange, naringin has the activities of antioxidation, anti-inflammation, blood fat reduction, blood sugar reduction, cancer resistance and the like, neohesperidin has the activities of antianaphylaxis, nervous system protection, blood fat reduction and the like, can be used as a flavoring agent for diabetics, and is widely applied to the fields of food, medicine and the like.
In the prior art, the method mainly extracts naringin, neohesperidin and other general flavones and synephrine in the fruit by hot water or organic solvent extraction, and has the defects of low extraction rate and low extraction efficiency to be improved. Therefore, there is a need to develop new methods for extracting synephrine, naringin and neohesperidin from citrus aurantium to improve the extraction rate and efficiency, so as to fully utilize the values of synephrine, naringin and neohesperidin in citrus aurantium.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using an ultrasonic-assisted aqueous two-phase system so as to improve the extraction rate and the extraction efficiency of the synephrine, naringin and neohesperidin in the immature bitter oranges.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using an ultrasonic-assisted aqueous two-phase system comprises the following steps:
(1) crushing the dried immature bitter oranges, and sieving the crushed immature bitter oranges by a sieve of 40-200 meshes to obtain immature bitter orange powder;
(2) mixing the immature bitter orange powder and the ethanol/inorganic salt aqueous two-phase system according to the mass ratio of the ethanol/inorganic salt aqueous two-phase system to the immature bitter orange powder of (10-60): 1, carrying out ultrasonic extraction at 20-70 ℃ for 10-60 min, centrifuging, collecting an upper phase, and removing solid medicine residues to obtain an extracting solution containing synephrine, naringin and neohesperidin;
the inorganic salt in the ethanol/inorganic salt double-aqueous phase system is sodium citrate, disodium hydrogen phosphate, ammonium sulfate, dipotassium hydrogen phosphate or potassium carbonate, the mass fraction of the inorganic salt in the ethanol/inorganic salt double-aqueous phase system is 15-25%, and the mass fraction of the ethanol is 25-35%.
In the technical scheme of the method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using the ultrasonic-assisted aqueous two-phase system, the extraction in the step (2) is preferably carried out under the condition that the power is 80-150W.
In the technical scheme of the method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using the ultrasonic-assisted aqueous two-phase system, in the ethanol/inorganic salt aqueous phase system, the mass fraction of inorganic salt is preferably 15-21%, and the mass fraction of ethanol is preferably 25-33%. More preferably, the inorganic salt in the ethanol/inorganic salt aqueous phase system is potassium carbonate. Further preferably, when the inorganic salt in the ethanol/inorganic salt aqueous phase system is potassium carbonate, the mass fraction of the inorganic salt in the ethanol/inorganic salt aqueous phase system is 19-21%, and the mass fraction of the ethanol is 27-33%.
In the technical scheme of the method for extracting synephrine, naringin and neohesperidin from immature bitter oranges through an ultrasonic-assisted aqueous two-phase system, in the step (2), the immature bitter orange powder and the ethanol/inorganic salt aqueous two-phase system are preferably mixed according to the mass ratio of the ethanol/inorganic salt aqueous two-phase system to the immature bitter orange powder of (20-40): 1.
In the technical scheme of the method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using the ultrasonic-assisted aqueous two-phase system, ultrasonic extraction is preferably performed at 30-50 ℃ in the step (2) for 20-40 min.
In the technical scheme of the method for extracting synephrine, naringin and neohesperidin from immature bitter oranges through an ultrasonic-assisted aqueous two-phase system, dried immature bitter oranges are preferably crushed in the step (1) and sieved by a 100-140-mesh sieve to obtain immature bitter orange powder.
Compared with the prior art, the invention has the following beneficial technical effects:
1. the invention provides a method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using an ultrasonic-assisted aqueous two-phase system. Compared with the traditional ultrasonic-assisted solvent extraction mode, the method effectively improves the extraction rate and extraction efficiency of synephrine, naringin and neohesperidin in the immature bitter orange, and the obtained extracting solution has less impurity content.
2. The method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using the ultrasonic-assisted aqueous two-phase system has the advantages of simple process, short extraction time, easy recycling of organic solvents, mild extraction conditions and contribution to popularization and application in practice.
Drawings
FIG. 1 is an HPLC chart of the target product in samples obtained by different extraction methods, wherein (a) is an HPLC chart of synephrine (synephrine) in each sample, and (b) is an HPLC chart of naringin (naringin) and neohesperidin (neohesperidin) in each sample.
FIG. 2 shows the extraction yields of target products from samples obtained by different extraction methods.
Detailed Description
The method for extracting synephrine, naringin and neohesperidin from immature bitter orange by using an ultrasonic-assisted aqueous two-phase system provided by the invention is further explained by the following embodiments. It should be noted that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention, and those skilled in the art can make certain insubstantial modifications and adaptations of the present invention based on the above disclosure and still fall within the scope of the present invention.
In the following examples and comparative examples, immature bitter oranges used were dried young fruits of lime. The extraction rate (mg/g) of the target product is equal to the mass (mg) of the target product in the upper phase/the mass (g) of the immature bitter orange powder.
Comparative example 1
In the comparative example, synephrine, naringin and neohesperidin in immature bitter orange are extracted by 95% ethanol through ultrasound, and the steps are as follows:
(1) pulverizing dried fructus Aurantii Immaturus, and sieving with 120 mesh sieve to obtain fructus Aurantii Immaturus powder.
(2) Adding the immature bitter orange powder into 95% ethanol according to the mass ratio of 95% ethanol to immature bitter orange powder of 45:1, fully mixing, placing in a water bath at 49 ℃ for ultrasonic extraction for 30min under the power of 80W, centrifuging at the rotating speed of 3000rpm for 15min, collecting 95% ethanol extract, and removing solid medicine residues to obtain the extract containing synephrine, naringin and neohesperidin.
The content of synephrine, naringin and neohesperidin in the extracting solution is detected by HPLC, the corresponding HPLC map and the extraction rate of a target product are shown in figures 1-2, and the result shows that: the extraction rate of synephrine is 6.46mg/g, the extraction rate of naringin is 3.71mg/g, the extraction rate of neohesperidin is 3.36mg/g, and the total extraction rate of three target products is 13.54 mg/g.
Comparative example 2
In the comparative example, synephrine, naringin and neohesperidin in immature bitter orange are extracted by 50% ethanol with ultrasound, and the steps are as follows:
(1) pulverizing dried fructus Aurantii Immaturus, and sieving with 120 mesh sieve to obtain fructus Aurantii Immaturus powder.
(2) Adding the immature bitter orange powder into 50% ethanol according to the mass ratio of the 50% ethanol to the immature bitter orange powder of 45:1, fully mixing, placing in a water bath at 49 ℃ for ultrasonic extraction for 30min under the power of 80W, centrifuging at the rotating speed of 3000rpm for 15min, collecting 50% ethanol extract, and removing solid medicine residues to obtain the extract containing synephrine, naringin and neohesperidin.
The content of synephrine, naringin and neohesperidin in the extracting solution is detected by HPLC, the corresponding HPLC map and the extraction rate of a target product are shown in figures 1-2, and the result shows that: the extraction rate of synephrine is 13.55mg/g, the extraction rate of naringin is 8.51mg/g, the extraction rate of neohesperidin is 9.32mg/g, and the total extraction rate of three target products is 31.38 mg/g.
Comparative example 3
In the comparative example, synephrine, naringin and neohesperidin in immature bitter orange are ultrasonically extracted by deionized water, and the steps are as follows:
(1) pulverizing dried fructus Aurantii Immaturus, and sieving with 120 mesh sieve to obtain fructus Aurantii Immaturus powder.
(2) Adding the immature bitter orange powder into deionized water according to the mass ratio of the deionized water to the immature bitter orange powder of 45:1, fully mixing, placing in a water bath at 49 ℃ for ultrasonic extraction for 30min under the power of 80W, centrifuging for 15min at the rotating speed of 3000rpm, collecting water extract, and removing solid medicine residues to obtain an extracting solution containing synephrine, naringin and neohesperidin.
The content of synephrine, naringin and neohesperidin in the extracting solution is detected by HPLC, the corresponding HPLC map and the extraction rate of a target product are shown in figures 1-2, and the result shows that: the extraction rate of synephrine is 10.68mg/g, the extraction rate of naringin is 2.82mg/g, the extraction rate of neohesperidin is 2.38mg/g, and the total extraction rate of three target products is 15.88 mg/g.
Example 1
In this embodiment, a method for extracting synephrine, naringin, and neohesperidin from citrus aurantium by using an ultrasound-assisted aqueous two-phase system (ATPS) is provided, which includes the following steps:
(1) pulverizing dried fructus Aurantii Immaturus, and sieving with 120 mesh sieve to obtain fructus Aurantii Immaturus powder.
(2) According to ethanol/K2CO3The weight ratio of the aqueous two-phase system to the immature bitter orange powder is 45:12CO3Mixing the two aqueous phase systems, and ultrasonically extracting in water bath at 49 deg.C under 80W power for 30min, centrifuging at 3000rpm for 15min, collecting upper phase (alcohol-enriched phase), and removing solid residue to obtain extractive solution containing synephrine, naringin and neohesperidin;
the ethanol/K2CO3In aqueous two-phase system, K2CO3The mass fraction of the ethanol is 20.6 percent, the mass fraction of the ethanol is 27 percent, and taking 100g of a two-aqueous phase system as an example, the preparation method comprises the following steps: 20.6g K2CO3Dissolving in 52.4g water, and adding 27g anhydrous ethanol.
The content of synephrine, naringin and neohesperidin in the extracting solution is detected by HPLC, the corresponding HPLC map and the extraction rate of a target product are shown in figures 1-2, and the result shows that: the extraction rate of synephrine is 11.17mg/g, the extraction rate of naringin is 7.39mg/g, the extraction rate of neohesperidin is 89.27mg/g, and the total extraction rate of three target products is 107.83 mg/g.
In combination with comparative examples 1-3 and example 1, it can be seen that under the same conditions of liquid-solid ratio, extraction temperature, extraction time and ultrasonic power, ethanol/K is adopted in the invention2CO3The method has the advantages that the total extraction rate of the synephrine, the naringin and the neohesperidin in the immature bitter oranges can be remarkably improved by simultaneously extracting the synephrine, the naringin and the neohesperidin in the immature bitter oranges in an aqueous two-phase system, and the total extraction rate of the synephrine, the naringin and the neohesperidin in the immature bitter oranges is improved to 107.83mg/g from 13.54-31.38 mg/g in comparative examples 1-3.
Example 2
In this embodiment, a method for extracting synephrine, naringin and neohesperidin from citrus aurantium by using an ultrasonic-assisted aqueous two-phase system is provided, which includes the following steps:
(1) pulverizing dried fructus Aurantii Immaturus, and sieving with 120 mesh sieve to obtain fructus Aurantii Immaturus powder.
(2) According to ethanol/K2CO3The weight ratio of the aqueous two-phase system to the immature bitter orange powder is 40:12CO3Mixing two aqueous phase systems, ultrasonic extracting in 30 deg.C water bath under 80W for 20min, centrifuging at 3000rpm for 15min, collecting upper phase (alcohol-rich phase), and removing solid residue to obtain extractive solution containing synephrine, naringin and neohesperidin；
The ethanol/K2CO3In aqueous two-phase system, K2CO3The mass fraction of the ethanol is 19 percent, the mass fraction of the ethanol is 33 percent, and the preparation method is as follows by taking 100g of a two-aqueous phase system as an example: 19g K2CO3Adding 48g of water for dissolving, and then adding 33g of absolute ethyl alcohol to obtain the finished product.
The content of synephrine, naringin and neohesperidin in the extracting solution is detected by HPLC, and the result shows that: the extraction rate of synephrine is 4.93mg/g, the extraction rate of naringin is 4.66mg/g, the extraction rate of neohesperidin is 55.53mg/g, and the total extraction rate of three target products is 65.12 mg/g.
Example 3
In this embodiment, a method for extracting synephrine, naringin and neohesperidin from citrus aurantium by using an ultrasonic-assisted aqueous two-phase system is provided, which includes the following steps:
(1) pulverizing dried fructus Aurantii Immaturus, and sieving with 120 mesh sieve to obtain fructus Aurantii Immaturus powder.
(2) According to ethanol/K2CO3The weight ratio of the aqueous two-phase system to the immature bitter orange powder is 40:12CO3Mixing the two aqueous phase systems, performing ultrasonic extraction in 50 deg.C water bath at 80W power for 20min, centrifuging at 3000rpm for 15min, collecting upper phase (alcohol-rich phase), and removing solid residue to obtain extractive solution containing synephrine, naringin and neohesperidin;
the ethanol/K2CO3In aqueous two-phase system, K2CO3The mass fraction of the ethanol is 19 percent, the mass fraction of the ethanol is 33 percent, and the preparation method is as follows by taking 100g of a two-aqueous phase system as an example: 19g K2CO3Adding 48g of water for dissolving, and then adding 33g of absolute ethyl alcohol to obtain the finished product.
The content of synephrine, naringin and neohesperidin in the extracting solution is detected by HPLC, and the result shows that: the extraction rate of synephrine is 8.77mg/g, the extraction rate of naringin is 5.74mg/g, the extraction rate of neohesperidin is 74.98mg/g, and the total extraction rate of three target products is 89.49 mg/g.
Example 4
In this embodiment, a method for extracting synephrine, naringin and neohesperidin from citrus aurantium by using an ultrasonic-assisted aqueous two-phase system is provided, which includes the following steps:
(1) pulverizing dried fructus Aurantii Immaturus, and sieving with 120 mesh sieve to obtain fructus Aurantii Immaturus powder.
(2) According to ethanol/K2CO3The weight ratio of the aqueous two-phase system to the immature bitter orange powder is 40:12CO3Mixing the two aqueous phase systems, performing ultrasonic extraction in 50 deg.C water bath at 80W power for 30min, centrifuging at 3000rpm for 15min, collecting upper phase (alcohol-rich phase), and removing solid residue to obtain extractive solution containing synephrine, naringin and neohesperidin;
the ethanol/K2CO3In aqueous two-phase system, K2CO3The mass fraction of the ethanol is 19 percent, the mass fraction of the ethanol is 33 percent, and the preparation method is as follows by taking 100g of a two-aqueous phase system as an example: 19g K2CO3Adding 48g of water for dissolving, and then adding 33g of absolute ethyl alcohol to obtain the finished product.
The content of synephrine, naringin and neohesperidin in the extracting solution is detected by HPLC, and the result shows that: the extraction rate of synephrine is 11.21mg/g, the extraction rate of naringin is 6.96mg/g, the extraction rate of neohesperidin is 85.93mg/g, and the total extraction rate of the three target products is 104.1 mg/g.
Claims (8)
1. The method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using an ultrasonic-assisted aqueous two-phase system is characterized by comprising the following steps:
(1) crushing the dried immature bitter oranges, and sieving the crushed immature bitter oranges by a sieve of 40-200 meshes to obtain immature bitter orange powder;
(2) mixing the immature bitter orange powder and the ethanol/inorganic salt aqueous two-phase system according to the mass ratio of the ethanol/inorganic salt aqueous two-phase system to the immature bitter orange powder of (10-60): 1, carrying out ultrasonic extraction at 20-70 ℃ for 10-60 min, centrifuging, collecting an upper phase, and removing solid medicine residues to obtain an extracting solution containing synephrine, naringin and neohesperidin;
the inorganic salt in the ethanol/inorganic salt double-aqueous phase system is sodium citrate, disodium hydrogen phosphate, ammonium sulfate, dipotassium hydrogen phosphate or potassium carbonate, the mass fraction of the inorganic salt in the ethanol/inorganic salt double-aqueous phase system is 15-25%, and the mass fraction of the ethanol is 25-35%.
2. The method for extracting synephrine, naringin and neohesperidin from immature bitter oranges in an ultrasonic-assisted aqueous two-phase system according to claim 1, wherein the extraction in the step (2) is carried out under the condition that the power is 80-150W.
3. The method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using the ultrasonic-assisted aqueous two-phase system according to claim 1, wherein in the ethanol/inorganic salt aqueous phase system, the mass fraction of inorganic salt is 15-21%, and the mass fraction of ethanol is 25-33%.
4. The method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using the ultrasonic-assisted aqueous two-phase system according to claim 3, wherein the inorganic salt in the ethanol/inorganic salt aqueous phase system is potassium carbonate.
5. The method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using the ultrasonic-assisted aqueous two-phase system according to claim 4, wherein in the ethanol/inorganic salt aqueous phase system, the mass fraction of inorganic salt is 19-21%, and the mass fraction of ethanol is 27-33%.
6. The method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using the ultrasonic-assisted aqueous two-phase system according to any one of claims 1 to 5, wherein the immature bitter orange powder and the ethanol/inorganic salt aqueous two-phase system are mixed in the step (2) according to the mass ratio of the ethanol/inorganic salt aqueous two-phase system to the immature bitter orange powder of (20-40): 1.
7. The method for extracting synephrine, naringin and neohesperidin from immature bitter oranges in an ultrasonic-assisted aqueous two-phase system according to any one of claims 1 to 5, wherein the ultrasonic extraction in the step (2) is performed at 30-50 ℃ for 20-40 min.
8. The method for extracting synephrine, naringin and neohesperidin from immature bitter oranges in an ultrasonic-assisted aqueous two-phase system according to any one of claims 1 to 5, wherein the dried immature bitter oranges are crushed in the step (1) and sieved by a 100-140-mesh sieve to obtain immature bitter orange powder.
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