CN102432575B - Method for extracting high-purity hesperetin from immature bitter orange - Google Patents
Method for extracting high-purity hesperetin from immature bitter orange Download PDFInfo
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- CN102432575B CN102432575B CN201210017544.XA CN201210017544A CN102432575B CN 102432575 B CN102432575 B CN 102432575B CN 201210017544 A CN201210017544 A CN 201210017544A CN 102432575 B CN102432575 B CN 102432575B
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Abstract
The invention discloses a method for extracting high-purity hesperetin from immature bitter orange, which comprises the following steps: 1. pulverizing immature bitter orange, extracting with alcohol solvent under reflux three times, filtering, merging the three filtrates, and concentrating; 2. adding inorganic acid into the concentrated solution for hydrolysis, naturally cooling to room temperature, filtering, washing the filter residues, and centrifugalizing to obtain a crude hesperetin product; and 3. dissolving the crude hesperetin product in ethanol, adding activated carbon to decolorize under reflux, filtering, concentrating, crystallizing, filtering, and drying the filtered solid matter to obtain the hesperetin crystals of which the mass purity is not lower than 95%.By using the immature bitter orange as the raw material for extraction, hydrolysis and refinement, compared with the traditional technique of extracting hesperetin from hesperidin, the invention reduces the intermediate links, lowers the production loss, enhances the production yield of hesperetin, lowers the production cost, and eliminates the hesperidin refinement, drying and other links in the original production process, thereby greatly shortening the production cycle.
Description
Technical field
The invention belongs to the extractive technique field of effective ingredients in plant, be specifically related to a kind of method of extracting high purity Hesperitin from the dried immature fruit of citron orange.
Background technology
Hesperitin (Hesperetin) is a class natural flavone compounds, is extensively present in the botanical components such as fruit, flowers, food.Hesperitin has biology and pharmacologically active widely, is applied to multiple fields such as organic chemistry, medical science, agronomy, food.Modern medicine study shows that Hesperitin has that anti-oxidant, anti-inflammatory, antiviral, stomach invigorating, antibechic, protection are cardiovascular, neuroprotective, protect a series of effects such as liver, Hesperitin has anti-inflammatory action can reduce the generation of sebum, effectively suppress the growth of acne, be used for Acne treatment; Hesperitin has the osteoblastic effect of protection as biological anti-oxidant, can be as the auxiliary agent of Regular Insulin, be used for the treatment of the concurrent diabetes osteopathy of type i diabetes; The a series of Hesperitin ethers that synthesize with Hesperitin or ester derivative can effectively reduce the cholesterol level in feeding hypercholesterolemia experimental mouse blood plasma.It is mainly derived from Hesperidin (Hesperidin) hydrolysis at present, be mainly to utilize acid to be hydrolyzed Hesperidin, also useful enzyme process is hydrolyzed, but take Hesperidin as raw material production Hesperitin production cost higher, middle-chain is more, and the production cycle is longer.
Summary of the invention
Technical problem to be solved by this invention is for above-mentioned the deficiencies in the prior art, and a kind of method of extracting high purity Hesperitin from the dried immature fruit of citron orange is provided.The method is extracted hydrolysis take the dried immature fruit of citron orange as raw material refining, compare traditional technique of extracting Hesperitin take Hesperidin as raw material and reduced middle-chain, reduced production loss, improved the production yield of Hesperitin, reduced production cost, delete the links such as refining, be dried to Hesperidin in original production simultaneously, greatly reduced the production cycle.
For solving the problems of the technologies described above, the technical solution used in the present invention is: a kind of method of extracting high purity Hesperitin from the dried immature fruit of citron orange, it is characterized in that, and the method comprises the following steps:
Step 1, the dried immature fruit of citron orange is pulverized after by alcoholic solvent refluxing extraction three times, the alcoholic solvent consumption of refluxing extraction is 5～20 times of dried immature fruit of citron orange quality for the first time, reflux extracting time is 1 hour～2 hours, the alcoholic solvent consumption of refluxing extraction is 5～20 times of dried immature fruit of citron orange quality for the second time, reflux extracting time is 1 hour～2 hours, the alcoholic solvent consumption of refluxing extraction is 5～20 times of dried immature fruit of citron orange quality for the third time, reflux extracting time is 1 hour～2 hours, after filtering, merge three filtrates, it is 1.0～1.06 concentrated solution that the filtrate decompression of merging is concentrated into proportion;
Step 2, in concentrated solution described in step 1, add mineral acid to obtain mixing solutions, it by mixing solutions, in temperature, is the Water Under solution 3 hours～10 hours of 90 ℃～120 ℃, after naturally cooling to room temperature, filter, the filter residue that filtration is obtained is the rear centrifugal supernatant liquor of removing of soft water washing of 80 ℃～100 ℃ by temperature, repeated washing and centrifugal 1～3 time, obtain Hesperitin crude product; In described mixing solutions, the mass concentration of mineral acid is 3%～5%;
Step 3, by the crude product of Hesperitin described in step 2, by mass concentration, be more than 85% dissolve with ethanol, to dissolve after solution in add gac reflux decolour 1 hour～2 hours, then by the solution after decolouring, in temperature, be to filter under the condition of 50 ℃～80 ℃, filtrate after filtering is concentrated into 1/4 of filtrate volume, again the filtrate after concentrated is placed in to crystallization and filtration under normal temperature, by dry the solid matter after filtering, obtain quality purity and be not less than 96% Hesperitin crystallization.
A kind of above-mentioned method of extracting high purity Hesperitin from the dried immature fruit of citron orange, alcoholic solvent described in step 1 is methyl alcohol or ethanol.
A kind of above-mentioned method of extracting high purity Hesperitin from the dried immature fruit of citron orange, the mass concentration of described methyl alcohol is not less than 85%.
A kind of above-mentioned method of extracting high purity Hesperitin from the dried immature fruit of citron orange, the mass concentration of described ethanol is not less than 85%.
A kind of above-mentioned method of extracting high purity Hesperitin from the dried immature fruit of citron orange, mineral acid described in step 2 is sulfuric acid or hydrochloric acid.
A kind of above-mentioned method of extracting high purity Hesperitin from the dried immature fruit of citron orange, described in step 2, soft water hardness is not more than 17.1mg/L.
A kind of above-mentioned method of extracting high purity Hesperitin from the dried immature fruit of citron orange, the consumption of ethanol described in step 3 is 8～15 times of Hesperitin crude product quality, the consumption of described gac is 0.5%～1% of ethanol consumption by mass percentage.
The present invention compared with prior art has the following advantages:
1, of the present invention simple for process, with short production cycle, production unit is less demanding, is easy to realize the suitability for industrialized production of Hesperitin.
2, adopt method of the present invention, the product yield obtaining is high, and quality product purity is not less than 96%, and every Oranoleptic indicator of the Hesperitin of extraction all can reach market demands.
3, the present invention is with low cost, and the solvent cost of employing is low, simultaneously environmentally safe.
4, it is refining that the present invention extracts hydrolysis take the dried immature fruit of citron orange as raw material, compare traditional technique of extracting Hesperitin take Hesperidin as raw material and reduced middle-chain, reduced production loss, improved the production yield of Hesperitin, reduced production cost, delete the links such as refining, be dried to Hesperidin in original production simultaneously, greatly reduced the production cycle.
Below by embodiment, technical solution of the present invention is described in further detail.
Embodiment
Embodiment 1
Step 1, the alcohol reflux that is 85% by mass concentration after the 1kg dried immature fruit of citron orange is pulverized three times, the ethanol consumption of three refluxing extraction is 20 times of dried immature fruit of citron orange quality, reflux extracting time is 2 hours, after filtering, merge three filtrates, it is 1.02 concentrated solution that the filtrate decompression of merging is concentrated into proportion;
Step 2, in concentrated solution described in step 1, add sulfuric acid (or hydrochloric acid) to obtain mixing solutions, it by mixing solutions, in temperature, is the Water Under solution 5 hours of 98 ℃, after naturally cooling to room temperature, filter, the filter residue temperature that filtration is obtained is 80 ℃, hardness is not more than the rear centrifugal supernatant liquor of removing of soft water washing of 17.1mg/L, repeated washing and centrifugal 3 times, obtain Hesperitin crude product; The mass concentration of sulfuric acid in described mixing solutions (or hydrochloric acid) is 5%;
Step 3, the dissolve with ethanol that is 95% by mass concentration by the crude product of Hesperitin described in step 2, the consumption of ethanol is 10 times of Hesperitin crude product quality, then to the gac reflux decolour 2 hours that adds ethanol quality 1% in the solution after dissolving, then in temperature, be to filter under 50 ℃ of conditions, filtrate after filtering is concentrated into 1/4 of filtrate volume, finally the filtrate after concentrated is placed in to crystallization and filtration under normal temperature, by dry the solid matter after filtering, obtain the faint yellow Hesperitin crystallization of 62g, through HPLC, detecting Hesperitin quality purity is 96.5%.
The present embodiment extracts hydrolysis take the dried immature fruit of citron orange as raw material refining, compare traditional technique of extracting Hesperitin take Hesperidin as raw material and reduced middle-chain, reduced production loss, improved the production yield of Hesperitin, reduced production cost, delete the links such as refining, be dried to Hesperidin in original production simultaneously, greatly reduced the production cycle.
Embodiment 2
Step 1, the alcohol reflux that is 95% by mass concentration after the 1kg dried immature fruit of citron orange is pulverized three times, the ethanol consumption of three refluxing extraction is 10 times of dried immature fruit of citron orange quality, reflux extracting time is 1 hour, after filtering, merge three filtrates, it is 1.0 concentrated solution that the filtrate decompression of merging is concentrated into proportion;
Step 2, in concentrated solution described in step 1, add sulfuric acid (or hydrochloric acid) to obtain mixing solutions, it by mixing solutions, in temperature, is the Water Under solution 3 hours of 120 ℃, after naturally cooling to room temperature, filter, the filter residue temperature that filtration is obtained is 100 ℃, hardness is not more than the rear centrifugal supernatant liquor of removing of soft water washing of 17.1mg/L, obtains Hesperitin crude product; The mass concentration of sulfuric acid in described mixing solutions (or hydrochloric acid) is 3%;
Step 3, the dissolve with ethanol that is 90% by mass concentration by the crude product of Hesperitin described in step 2, the consumption of ethanol is 8 times of Hesperitin crude product quality, then to the gac reflux decolour 1 hour that adds ethanol quality 0.5% in the solution after dissolving, then in temperature, be to filter under 80 ℃ of conditions, filtrate after filtering is concentrated into 1/4 of filtrate volume, finally the filtrate after concentrated is placed in to crystallization and filtration under normal temperature, by dry the solid matter after filtering, obtain the faint yellow Hesperitin crystallization of 54g, through HPLC, detecting Hesperitin quality purity is 96%.
The present embodiment extracts hydrolysis take the dried immature fruit of citron orange as raw material refining, compare traditional technique of extracting Hesperitin take Hesperidin as raw material and reduced middle-chain, reduced production loss, improved the production yield of Hesperitin, reduced production cost, delete the links such as refining, be dried to Hesperidin in original production simultaneously, greatly reduced the production cycle.
Embodiment 3
Step 1, the methanol eddy that is 85% by mass concentration afterwards by the pulverizing of the 10kg dried immature fruit of citron orange extract three times, the methanol usage of refluxing extraction is 5 times of dried immature fruit of citron orange quality for the first time, reflux extracting time is 1.5 hours, the methanol usage of refluxing extraction is 8 times of dried immature fruit of citron orange quality for the second time, reflux extracting time is 2 hours, the methanol usage of refluxing extraction is 10 times of dried immature fruit of citron orange quality for the third time, reflux extracting time is 1 hour, after filtering, merge three filtrates, it is 1.06 concentrated solution that the filtrate decompression of merging is concentrated into proportion;
Step 2, in concentrated solution described in step 1, add hydrochloric acid (or sulfuric acid) to obtain mixing solutions, it by mixing solutions, in temperature, is the Water Under solution 10 hours of 90 ℃, after naturally cooling to room temperature, filter, the filter residue temperature that filtration is obtained is 90 ℃, hardness is not more than the rear centrifugal supernatant liquor of removing of soft water washing of 17.1mg/L, repeated washing and centrifugal 2 times, obtain Hesperitin crude product; The mass concentration of hydrochloric acid in described mixing solutions (or sulfuric acid) is 4%;
Step 3, the dissolve with ethanol that is 85% by mass concentration by the crude product of Hesperitin described in step 2, the consumption of ethanol is 15 times of Hesperitin crude product quality, then to the gac reflux decolour 1.5 hours that adds ethanol quality 0.8% in the solution after dissolving, then in temperature, be to filter under 70 ℃ of conditions, filtrate after filtering is concentrated into 1/4 of filtrate volume, finally the filtrate after concentrated is placed in to crystallization and filtration under normal temperature, by dry the solid matter after filtering, obtain the faint yellow Hesperitin crystallization of 753g, through HPLC, detecting Hesperitin quality purity is 96.2%.
The present embodiment extracts hydrolysis take the dried immature fruit of citron orange as raw material refining, compare traditional technique of extracting Hesperitin take Hesperidin as raw material and reduced middle-chain, reduced production loss, improved the production yield of Hesperitin, reduced production cost, delete the links such as refining, be dried to Hesperidin in original production simultaneously, greatly reduced the production cycle.
Embodiment 4
Step 1, the methanol eddy that is 90% by mass concentration afterwards by the pulverizing of the 10kg dried immature fruit of citron orange extract three times, the methanol usage of refluxing extraction is 20 times of dried immature fruit of citron orange quality for the first time, reflux extracting time is 2 hours, the methanol usage of refluxing extraction is 5 times of dried immature fruit of citron orange quality for the second time, reflux extracting time is 1.5 hours, the methanol usage of refluxing extraction is 5 times of dried immature fruit of citron orange quality for the third time, reflux extracting time is 1.5 hours, after filtering, merge three filtrates, it is 1.04 concentrated solution that the filtrate decompression of merging is concentrated into proportion;
Step 2, in concentrated solution described in step 1, add sulfuric acid (or hydrochloric acid) to obtain mixing solutions, it by mixing solutions, in temperature, is the Water Under solution 6 hours of 100 ℃, after naturally cooling to room temperature, filter, the filter residue temperature that filtration is obtained is 95 ℃, hardness is not more than the rear centrifugal supernatant liquor of removing of soft water washing of 17.1mg/L, repeated washing and centrifugal 1 time, obtain Hesperitin crude product; The mass concentration of sulfuric acid in described mixing solutions (or hydrochloric acid) is 4%;
Step 3, the dissolve with ethanol that is 95% by mass concentration by the crude product of Hesperitin described in step 2, the consumption of ethanol is 12 times of Hesperitin crude product quality, then to the gac reflux decolour 2 hours that adds ethanol quality 1% in the solution after dissolving, then in temperature, be to filter under 60 ℃ of conditions, filtrate after filtering is concentrated into 1/4 of filtrate volume, finally the filtrate after concentrated is placed in to crystallization and filtration under normal temperature, by dry the solid matter after filtering, obtain the faint yellow Hesperitin crystallization of 802g, through HPLC, detecting Hesperitin quality purity is 96.7%.
The present embodiment extracts hydrolysis take the dried immature fruit of citron orange as raw material refining, compare traditional technique of extracting Hesperitin take Hesperidin as raw material and reduced middle-chain, reduced production loss, improved the production yield of Hesperitin, reduced production cost, delete the links such as refining, be dried to Hesperidin in original production simultaneously, greatly reduced the production cycle.
The above; it is only preferred embodiment of the present invention; not the present invention is done to any restriction, every any simple modification of above embodiment being done according to invention technical spirit, change and equivalent structure change, and all still belong in the protection domain of technical solution of the present invention.
Claims (5)
1. a method of extracting high purity Hesperitin from the dried immature fruit of citron orange, is characterized in that, the method comprises the following steps:
Step 1, the dried immature fruit of citron orange is pulverized after by alcoholic solvent refluxing extraction three times, the alcoholic solvent consumption of refluxing extraction is 5～20 times of dried immature fruit of citron orange quality for the first time, reflux extracting time is 1 hour～2 hours, the alcoholic solvent consumption of refluxing extraction is 5～20 times of dried immature fruit of citron orange quality for the second time, reflux extracting time is 1 hour～2 hours, the alcoholic solvent consumption of refluxing extraction is 5～20 times of dried immature fruit of citron orange quality for the third time, reflux extracting time is 1 hour～2 hours, after filtering, merge three filtrates, it is 1.0～1.06 concentrated solution that the filtrate decompression of merging is concentrated into proportion;
Step 2, in concentrated solution described in step 1, add mineral acid to obtain mixing solutions, it by mixing solutions, in temperature, is the Water Under solution 3 hours～10 hours of 90 ℃～120 ℃, after naturally cooling to room temperature, filter, the filter residue that filtration is obtained is the rear centrifugal supernatant liquor of removing of soft water washing of 80 ℃～100 ℃ by temperature, repeated washing and centrifugal 1～3 time, obtain Hesperitin crude product; In described mixing solutions, the mass concentration of mineral acid is 3%～5%; Described mineral acid is sulfuric acid or hydrochloric acid;
Step 3, by the crude product of Hesperitin described in step 2, by mass concentration, be more than 85% dissolve with ethanol, to dissolve after solution in add gac reflux decolour 1 hour～2 hours, then by the solution after decolouring, in temperature, be to filter under the condition of 50 ℃～80 ℃, filtrate after filtering is concentrated into 1/4 of filtrate volume, again the filtrate after concentrated is placed in to crystallization and filtration under normal temperature, by dry the solid matter after filtering, obtain quality purity and be not less than 96% Hesperitin crystallization; The consumption of described ethanol is 8～15 times of Hesperitin crude product quality, and the consumption of described gac is 0.5%～1% of ethanol consumption.
2. a kind of method of extracting high purity Hesperitin from the dried immature fruit of citron orange according to claim 1, is characterized in that, alcoholic solvent described in step 1 is methyl alcohol or ethanol.
3. a kind of method of extracting high purity Hesperitin from the dried immature fruit of citron orange according to claim 2, is characterized in that, the mass concentration of described methyl alcohol is not less than 85%.
4. a kind of method of extracting high purity Hesperitin from the dried immature fruit of citron orange according to claim 2, is characterized in that, the mass concentration of described ethanol is not less than 85%.
5. a kind of method of extracting high purity Hesperitin from the dried immature fruit of citron orange according to claim 1, is characterized in that, described in step 2, soft water hardness is not more than 17.1mg/L.
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| CN104327031A (en) * | 2014-10-17 | 2015-02-04 | 南通海天生物科技有限公司 | Process for extraction and separation of hesperetin from orange peel |
| CN105837646A (en) * | 2015-01-16 | 2016-08-10 | 刘力 | Flavonoid new chemical entity, composition and use |
| 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 |
| CN113651791B (en) * | 2021-09-01 | 2023-03-24 | 湖南华诚生物资源股份有限公司 | Method for separating hesperetin from immature bitter orange |
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| CN1748740A (en) * | 2004-09-17 | 2006-03-22 | 王英锋 | Imature bitter orange total flavone and its preparing mthod for its preparation and quality control method |
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| JPS51105069A (en) * | 1975-03-11 | 1976-09-17 | Meiji Seika Co | HESUPERECHINNOSEIZOHOHO |
| KR100771081B1 (en) * | 2006-05-29 | 2007-10-29 | 한국생명공학연구원 | Method of preparation of neohesperidin dihydrochalcone from citrus |
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| CN1748740A (en) * | 2004-09-17 | 2006-03-22 | 王英锋 | Imature bitter orange total flavone and its preparing mthod for its preparation and quality control method |
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Denomination of invention: A kind of method for extracting high-purity hesperetin from Fructus Aurantii Effective date of registration: 20220913 Granted publication date: 20140423 Pledgee: Xi'an innovation financing Company limited by guarantee Pledgor: XI'AN XIAOCAO BOTANICAL DEVELOPMENT Co.,Ltd. Registration number: Y2022610000591 |
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