CN102718668A - Method for extracting synephrine and hesperidin from citrus aurantium - Google Patents
Method for extracting synephrine and hesperidin from citrus aurantium Download PDFInfo
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- CN102718668A CN102718668A CN2012102245930A CN201210224593A CN102718668A CN 102718668 A CN102718668 A CN 102718668A CN 2012102245930 A CN2012102245930 A CN 2012102245930A CN 201210224593 A CN201210224593 A CN 201210224593A CN 102718668 A CN102718668 A CN 102718668A
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Abstract
The invention discloses a method for extracting synephrine and hesperidin from citrus aurantium, and relates to a method for producing and processing traditional Chinese medicine. The method comprises the following steps of: step 1, washing and crushing a citrus aurantium raw material into citrus aurantium granules; adding an acid solution for soaking the citrus aurantium granules, then carrying out percolation and extracting extract, concentrating the extract under the reduced pressure to obtain extractum, and drying the extractum under the reduced pressure to obtain synephrine; step 2, adding a weak base solution into the leached citrus aurantium granules which are extracted after being soaked by the acid solution, carrying out decoction and removing impurities, then adding a mixed solvent of sodium hydroxide and calcium chloride into the citrus aurantium granules, and extracting to obtain extract; step 3, adding hydrochloric acid into the extract for neutralization until the pH value is 3-7, standing still and crystallizating; and step 4, collecting crystalline, and drying to obtain the hesperidin. Compared with the prior art, the method can be used for extracting two components without using an organic solvent, so that the production cost is reduced, the production technology is simplified, the synephrine yield is more than 15%, the content of the synephrine is more than 10%, the hesperidin yield reaches more than 27%, and the content of the hesperidin is more than 96%; and therefore, the method is suitable for industrialized mass production.
Description
Technical field
The present invention relates to a kind of Chinese medicine production, manufacture field, particularly a kind of method of from the dried immature fruit of citron orange, extracting synephrine and hesperidine.
Background technology
The dried immature fruit of citron orange is a conventional Chinese medicine, is the dry young fruit of rutaceae bitter orange and cultivated variety thereof or sweet orange, has regulating qi-flowing for strengthening spleen, the effects such as diffusing ruffian of reducing phlegm.Synephrine is one of composition in the dried immature fruit of citron orange; Has vasoconstriction; The effect of rising blood pressure and expansion trachea and bronchus has shock, improves the effect that newly becomes metabolism, fat-reducing, is a kind of natural stimulant; Ypotension when being used to treat bronchial asthma and operation and anesthesia clinically, collapse and shock etc.Hesperidine is kept the normal osmotic pressure of blood vessel, lowers the fragility of blood vessel, shortens bleeding time, prevents effects such as arteriosclerosis, is widely used in medical fields such as hypertension therapeutic, also can be used for foodstuff additive.
Existing documents and materials record is from the dried immature fruit of citron orange, to extract single component at present mostly, is that CN1318538A adopts the water extraction synephrine like publication number, and this water extraction synephrine extraction yield is low, and content is low.Publication number CN1587272A is with high-load naringin of high speed adverse current chromatogram separation and purification and hesperidine etc., and equipment requirements is high on the one hand, and what extract on the other hand is mixture but not single product.And these process for extracting or be to extract synephrine, or be to extract hesperidine, not having a kind of technology is can obtain synephrine and hesperidine simultaneously.
Material and term explanation
Among hydrochloric acid-the present invention, hydrochloric acid is commercially available technical grade.
Among sodium hydrogencarbonate-the present invention, sodium hydrogencarbonate is commercially available technical grade.
Among sodium hydroxide-the present invention, sodium hydroxide is commercially available technical grade.
Among calcium chloride-the present invention, calcium chloride is commercially available technical grade.
Among diafiltration-the present invention; Diafiltration is meant diafiltration, in the filtration operation process, when being processed material through film; Because film is to small molecules in the material and the selective permeation between the macromolecular components; Small molecules then sees through film along with solvent and is constantly removed, and has improved the separating size of being cut component and seeing through component, thereby has reached the purpose that material is purified.
Among the dried immature fruit of citron orange-the present invention, the dried immature fruit of citron orange is meant the commercially available dry young fruit of rutaceae bitter orange and cultivated variety or sweet orange.
Among synephrine-the present invention, the English Synephrine of synephrine, Latin Fructus aurantii Immaturus, molecular formula C9H13NO2, molecular weight are 167.20.
Among hesperidine-the present invention, hesperidine is meant English Hesperidin, Latin Citrus aurantium L, and molecular formula C28H34O15, molecular weight are 610.55.
Among concentration %-the present invention, do not have outside the special instruction, concentration % is a mass percent.
Summary of the invention
The object of the invention just is to provide a kind of method of from the dried immature fruit of citron orange, extracting synephrine and hesperidine, and the method for synephrine and hesperidine of should from the dried immature fruit of citron orange, extracting has been extracted two kinds of composition synephrines and hesperidine respectively.
Technical scheme of the present invention is: a kind of method of from the dried immature fruit of citron orange, extracting synephrine and hesperidine; May further comprise the steps: step 1, be ground into dried immature fruit of citron orange grain after dried immature fruit of citron orange raw material cleaned; Add acid solution immersion back percolating extract and get extracting solution; The extracting solution concentrating under reduced pressure gets medicinal extract, and the medicinal extract drying under reduced pressure obtains synephrine; After dried immature fruit of citron orange grain adds weak caustic solution and decocts impurity elimination after the lixiviate after step 2, the acid solution soaking and extracting, after the impurity elimination in the dried immature fruit of citron orange grain hydro-oxidation sodium and calcium chloride mixed solvent extract extracting solution; Step 3, extracting solution add hydrochloric acid and are neutralized to pH value 3-7, leave standstill crystallization; Step 4, collection xln, the dry hesperidine that gets.
As preferably, said acid solution is a hydrochloric acid soln, and this hydrochloric acid soln strength of solution is 0.06m ~ 0.08M.
As preferably, said concentrating under reduced pressure condition is a vacuum degree control-0.07~-0.08Mpa, temperature is below 80 ℃.
As preferably, said medicinal extract specific gravity control is 1.1~1.2.
As preferably, said weak caustic solution is a sodium hydrogen carbonate solution, and this sodium hydrogen carbonate solution concentration is 0.5%.
As preferably, said decoction number of times is 3 times.
As preferably, said sodium hydroxide and calcium chloride mixed solvent are sodium hydroxide and 0.5% calcium chloride of 0.15M.
Compared with prior art; Beneficial effect of the present invention is: from dried immature fruit of citron orange raw material, extract single component for to extract synephrine and hesperidine respectively from same raw material because the present invention changes; Not not with an organic solvent, reduce production cost on the one hand, simplified production technique.The synephrine yield is greater than 15% on the other hand, and content is greater than 10%, and the Hesperidin yield can reach more than 27%, and content is applicable to industrialized production greater than 96%.
Description of drawings
Fig. 1 is a process flow sheet of the present invention.
Embodiment
To combine accompanying drawing that the present invention is described further below.
The method of from the dried immature fruit of citron orange, extracting synephrine and hesperidine as shown in Figure 1 may further comprise the steps:
Step 1, be ground into dried immature fruit of citron orange grain after dried immature fruit of citron orange raw material cleaned, add acid solution and soak the back percolating extract and get extracting solution, the extracting solution concentrating under reduced pressure gets medicinal extract, and the medicinal extract drying under reduced pressure obtains synephrine.
After dried immature fruit of citron orange grain adds weak caustic solution and decocts impurity elimination after the lixiviate after step 2, the acid solution soaking and extracting, after the impurity elimination in the dried immature fruit of citron orange grain hydro-oxidation sodium and calcium chloride mixed solvent extract extracting solution.
Step 3, extracting solution add hydrochloric acid and are neutralized to pH value 3~7, leave standstill crystallization.The concentration of hydrochloric acid that neutralization is used is 31%.
Step 4, collection xln, the dry hesperidine that gets.
Embodiment 1:
1) get and be ground into dried immature fruit of citron orange grain after the 1000kg dried immature fruit of citron orange cleans with tap water, drop in the extractor, the hydrochloric acid soln that adds 5000L 0.08M leaves standstill and soaked 1 hour, and percolating extract was extracted 6 hours then, the collection extracting solution.
2) with 1) extracting solution concentrating under reduced pressure after filtering gets medicinal extract, and the medicinal extract specific gravity control is 1.1~1.2.Concentrate vacuum degree control-0.07~-0.08Mpa, temperature is below 80 ℃.
3) with 2) pulverize behind the medicinal extract drying under reduced pressure of gained the synephrine product.
4) with 1) dried immature fruit of citron orange grain after the lixiviate after hydrochloric acid soln extracts, add the sodium hydrogen carbonate solution of 4000L 0.5%, be heated to and boil, protect and boiled the decoction liquor of draining 30 minutes.
5) 4) decoct in the dried immature fruit of citron orange grain after the impurity elimination, add the sodium hydroxide and the calcium chloride mixing solutions percolating extract of 75kg of 15000L 0.15M, the collection extracting solution, the extraction temperature is a normal temperature, 12 hours extraction times.
6) with 5) extracting solution add hydrochloric acid and transfer pH value to 7, left standstill crystallization 1 hour.
7) with 6) leave standstill crystallization, the supernatant clear liquid gets into recovery system, the crystal that collecting precipitation gets off, the dry hesperidine that gets.
The synephrine of gained and hesperidine see the following form one.
Embodiment 2:
1) get and be ground into dried immature fruit of citron orange grain after the 1000kg dried immature fruit of citron orange cleans with tap water, drop in the extractor, the hydrochloric acid soln that adds 7000L 0.07M leaves standstill and soaked 2 hours, and percolating extract was extracted 7 hours then, the collection extracting solution.
2) with 1) extracting solution concentrating under reduced pressure after filtering gets medicinal extract, and the medicinal extract specific gravity control is 1.1~1.2.Concentrate the vacuum tightness control-0.07~-0.08Mpa, temperature is below 80 ℃.
3) with 2) gained medicinal extract drying under reduced pressure gets synephrine.
4) with 1) dried immature fruit of citron orange grain after hydrochloric acid soln extracts, add the sodium hydrogen carbonate solution of 4000L 0.6%, be heated to and boil, protect and boiled the decoction liquor of draining 30 minutes.Decoct three (promptly add the sodium hydrogen carbonate solution of 4000L 0.6% at every turn, be heated to and boil, protect and boiled the decoction liquor of draining 30 minutes) impurity eliminations altogether with quadrat method.
5) 4) decoct in the dried immature fruit of citron orange grain after the impurity elimination, add the sodium hydroxide and the calcium chloride mixing solutions percolating extract of 56kg of 14000L 0.2M, the collection extracting solution, the extraction temperature is a normal temperature, 13 hours extraction times.
6) with 5) extracting solution add hydrochloric acid and transfer pH value to 6.8, left standstill crystallization 2 hours.
7) with 6) leave standstill crystallization.The supernatant clear liquid gets into recovery system, the crystal that collecting precipitation gets off, the dry hesperidine that gets.
The synephrine of gained and hesperidine see the following form one.
Embodiment 3:
1) get and be ground into dried immature fruit of citron orange grain after the 1000kg dried immature fruit of citron orange cleans with tap water, drop in the extractor, the hydrochloric acid soln that adds 11000L 0.06M leaves standstill and soaked 4 hours, and percolating extract, is collected extracting solution at 7 hours extraction times then.
2) with 1) extracting solution concentrating under reduced pressure after filtering gets medicinal extract, and the medicinal extract specific gravity control is 1.1~1.2.Concentrate the vacuum tightness control-0.07~-0.08Mpa, temperature is below 80 ℃.
3) with 2) gained medicinal extract drying under reduced pressure gets synephrine.
4) with 1) dried immature fruit of citron orange grain after the lixiviate after hydrochloric acid soln extracts, add the sodium hydrogen carbonate solution of 4000L 0.4%, be heated to and boil, protect and boiled the decoction liquor of draining 30 minutes.Decoct secondary (promptly add the sodium hydrogen carbonate solution of 4000L 0.6% at every turn, be heated to and boil, protect and boiled the decoction liquor of draining 30 minutes) impurity elimination altogether with quadrat method.
5) 4) decoct in the dried immature fruit of citron orange grain after the impurity elimination, add the sodium hydroxide and the calcium chloride mixing solutions percolating extract of 56kg of 15000L 0.15M, the collection extracting solution, the extraction temperature is a normal temperature, 12 hours extraction times.
6) with 5) extracting solution add hydrochloric acid and transfer pH value to 7, left standstill crystallization 1 hour.
7) with 6) supernatant clear liquid after leaving standstill gets into recovery system, the crystal that collecting precipitation gets off, dry hesperidine.
The synephrine of gained and hesperidine see the following form one.
In the last table one, the weight=synephrine of drying back gained or the weight of hesperidine.
In the last table one, weight/dried immature fruit of citron orange weight * 100% of the synephrine (hesperidine) of yield=drying back gained.
In the last table one, the synephrine (hesperidine) * 100% of the pure synephrine wherein (pure hesperidine) that the synephrine (hesperidine) of content=drying back gained records with HPLC/drying back gained.
Claims (7)
1. method of from the dried immature fruit of citron orange, extracting synephrine and hesperidine is characterized in that may further comprise the steps:
Step 1, be ground into dried immature fruit of citron orange grain after dried immature fruit of citron orange raw material cleaned, add acid solution and soak the back percolating extract and get extracting solution, the extracting solution concentrating under reduced pressure gets medicinal extract, and the medicinal extract drying under reduced pressure obtains synephrine;
After dried immature fruit of citron orange grain adds weak caustic solution and decocts impurity elimination after the lixiviate after step 2, the acid solution soaking and extracting, after the impurity elimination in the dried immature fruit of citron orange grain hydro-oxidation sodium and calcium chloride mixed solvent extract extracting solution;
Step 3, extracting solution add hydrochloric acid and are neutralized to pH value 3~7, leave standstill crystallization;
Step 4, collection xln, the dry hesperidine that gets.
2. the method for from the dried immature fruit of citron orange, extracting synephrine and hesperidine according to claim 1, it is characterized in that: said acid solution is a hydrochloric acid soln, this hydrochloric acid soln strength of solution is 0.06M~0.08M.
3. the method for from the dried immature fruit of citron orange, extracting synephrine and hesperidine according to claim 1 is characterized in that: said concentrating under reduced pressure condition is a vacuum degree control-0.07~-0.08Mpa, temperature is below 80 ℃.
4. the method for from the dried immature fruit of citron orange, extracting synephrine and hesperidine according to claim 3, it is characterized in that: said medicinal extract specific gravity control is 1.1~1.2.
5. the method for from the dried immature fruit of citron orange, extracting synephrine and hesperidine according to claim 1, it is characterized in that: said weak caustic solution is a sodium hydrogen carbonate solution, this sodium hydrogen carbonate solution concentration is 0.5%.
6. the method for from the dried immature fruit of citron orange, extracting synephrine and hesperidine according to claim 5, it is characterized in that: said decoction number of times is 3 times.
7. the method for from the dried immature fruit of citron orange, extracting synephrine and hesperidine according to claim 1, it is characterized in that: said sodium hydroxide and calcium chloride mixed solvent are sodium hydroxide and 0.5% calcium chloride of 0.15M.
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103172685A (en) * | 2013-01-30 | 2013-06-26 | 向华 | Method for extracting hesperidin and synephrine from immature bitter oranges |
CN103387501A (en) * | 2013-07-13 | 2013-11-13 | 湖南鑫利生物科技有限公司 | Method for preparing high-purity L-synephrine |
CN104098634A (en) * | 2014-06-30 | 2014-10-15 | 四川新华康生物科技有限公司 | Technology for jointly extracting synephrine, hesperidin and PMFs (polymethoxy latednavones) from fructus aurantii immaturus |
CN104230871A (en) * | 2014-09-19 | 2014-12-24 | 成都绿拓生物科技有限公司 | Method for separating polymethoxylated flavones, hesperidin and synephrine from immature bitter orange |
CN104628800A (en) * | 2014-12-25 | 2015-05-20 | 李玉山 | Collaborative and clean extraction technology for hesperidin and synephrine in immature bitter oranges |
CN105481920A (en) * | 2015-12-08 | 2016-04-13 | 桂林三宝生物科技有限公司 | Method for extracting hesperidin, neohesperidin and synephrine |
CN105541645A (en) * | 2016-03-03 | 2016-05-04 | 湖南省农产品加工研究所 | Method for extracting synephrine in immature bitter oranges |
CN106278912A (en) * | 2016-08-03 | 2017-01-04 | 绵阳迪澳药业有限公司 | Crystallization process is utilized to prepare the production technology of high-purity Neosynephrine |
CN111393310A (en) * | 2020-04-24 | 2020-07-10 | 永州华茂生物科技有限责任公司 | Extraction method of immature bitter orange extract |
CN112047846A (en) * | 2020-10-13 | 2020-12-08 | 四川大学 | Method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using ultrasonic-assisted aqueous two-phase system |
CN114181271A (en) * | 2021-12-16 | 2022-03-15 | 宁波杰顺生物科技有限公司 | Hesperidin extract and preparation method thereof |
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Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103172685A (en) * | 2013-01-30 | 2013-06-26 | 向华 | Method for extracting hesperidin and synephrine from immature bitter oranges |
CN103172685B (en) * | 2013-01-30 | 2015-05-13 | 花垣恒远植物生化有限责任公司 | Method for extracting hesperidin and synephrine from immature bitter oranges |
CN103387501B (en) * | 2013-07-13 | 2015-06-03 | 湖南鑫利生物科技有限公司 | Method for preparing high-purity L-synephrine |
CN103387501A (en) * | 2013-07-13 | 2013-11-13 | 湖南鑫利生物科技有限公司 | Method for preparing high-purity L-synephrine |
CN104098634A (en) * | 2014-06-30 | 2014-10-15 | 四川新华康生物科技有限公司 | Technology for jointly extracting synephrine, hesperidin and PMFs (polymethoxy latednavones) from fructus aurantii immaturus |
CN104230871A (en) * | 2014-09-19 | 2014-12-24 | 成都绿拓生物科技有限公司 | Method for separating polymethoxylated flavones, hesperidin and synephrine from immature bitter orange |
CN104628800A (en) * | 2014-12-25 | 2015-05-20 | 李玉山 | Collaborative and clean extraction technology for hesperidin and synephrine in immature bitter oranges |
CN105481920A (en) * | 2015-12-08 | 2016-04-13 | 桂林三宝生物科技有限公司 | Method for extracting hesperidin, neohesperidin and synephrine |
CN105481920B (en) * | 2015-12-08 | 2018-11-23 | 周治德 | A method of extracting aurantiamarin, neohesperidin and synephrine |
CN105541645A (en) * | 2016-03-03 | 2016-05-04 | 湖南省农产品加工研究所 | Method for extracting synephrine in immature bitter oranges |
CN106278912A (en) * | 2016-08-03 | 2017-01-04 | 绵阳迪澳药业有限公司 | Crystallization process is utilized to prepare the production technology of high-purity Neosynephrine |
CN111393310A (en) * | 2020-04-24 | 2020-07-10 | 永州华茂生物科技有限责任公司 | Extraction method of immature bitter orange extract |
CN112047846A (en) * | 2020-10-13 | 2020-12-08 | 四川大学 | Method for extracting synephrine, naringin and neohesperidin from immature bitter oranges by using ultrasonic-assisted aqueous two-phase system |
CN114181271A (en) * | 2021-12-16 | 2022-03-15 | 宁波杰顺生物科技有限公司 | Hesperidin extract and preparation method thereof |
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