CN103601775A - Method for extracting hesperidin from orange peels - Google Patents
Method for extracting hesperidin from orange peels Download PDFInfo
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- CN103601775A CN103601775A CN201310617376.2A CN201310617376A CN103601775A CN 103601775 A CN103601775 A CN 103601775A CN 201310617376 A CN201310617376 A CN 201310617376A CN 103601775 A CN103601775 A CN 103601775A
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Abstract
The invention discloses a method for extracting hesperidin from orange peels. The method comprises the following steps of carrying out alcohol extraction, subjecting an alcohol extraction solution to macroporous resin column chromatography, carrying out eluate crystallization and recrystallization, and also a step of removing impurities through water extraction before the extraction step, wherein the step of removing impurities through water extraction before the extraction step specifically comprises the substeps of adding water to the orange peels and extracting for 1-3 hours under the condition of normal temperature, and then filtering and collecting the orange peels before the next alcohol extraction step. The method disclosed by the invention is characterized in that through the operations of firstly extracting the orange peels by using water and abandoning the water extract, excessive water soluble impurities in the orange peels can be removed and the load of the subsequent purification step is greatly reduced, and in the meantime, the hesperidin content and yield of the product obtained through extraction by using lower alcohol subsequently are higher than those of a product obtained through direct extraction by using the lower alcohol without removing impurities.
Description
Technical field
The present invention relates to the extracting method of activeconstituents in plant, be specifically related to extract the method for Hesperidin from peel of Citrus reticulata Blanco.
Background technology
Hesperidin is also hesperidine, has the osmotic pressure of maintaining, strengthens capillary vessel toughness, shortens the bleeding time and reduce the effects such as cholesterol, clinically for the assisting therapy of cardiovascular system diseases, can cultivate the multiple medicine that prevents arteriosclerosis and myocardial infarction.
Hesperidin is extensively present in rutaceae, and wherein in the plant pericarp of Citrus, content is the highest.Oranges and tangerines are the main large class fruit of south China, and south is used for outlet, eats or be processed into can raw.Cannery is when cooing oranges and tangerines can, and peel of Citrus reticulata Blanco is often dropped; And in peel of Citrus reticulata Blanco, contain a large amount of Hesperidins, and reclaim peel of Citrus reticulata Blanco and can make full use of resource for deep processing or extraction Hesperidin, increase the benefit.The method of extracting at present Hesperidin from peel of Citrus reticulata Blanco or other raw material that contains Hesperidin is solvent mainly with low-carbon alcohol greatly, adopts backflow, microwave, the mode such as ultrasonic to extract, or sinks method with alkaline extraction acid.As the publication number patent of invention that is CN102718668A, a kind of method of extracting synephrine and hesperidine from the dried immature fruit of citron orange is disclosed, it is to take the dried immature fruit of citron orange as raw material, with after acid extraction synephrine, the dregs of a decoction decoct removal of impurities with weak base, then with sodium hydroxide and calcium chloride mixed solution, extract, then extracting solution adjusts pH to 3～7 crystallization to obtain hesperidine.But it is not high that the method obtains the yield of hesperidine.Publication number is the patent of invention of CN103172685A, a kind of technique of extracting hesperidine and synephrine from the dried immature fruit of citron orange is disclosed, the ethanolic soln refluxing extraction that first dried immature fruit of citron orange is contained to alkali through petroleum ether degreasing, use, the concentrated upper KLFC-150 macroporous resin column absorption of extracting solution, use ethanol stepwise elution, elutriant condensing crystal makes hesperidine sterling again.The method can obtain higher hesperidine yield and higher purity, but it need to use organic solvent sherwood oil, and operator healthy had to certain harm.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of method of extracting Hesperidin from peel of Citrus reticulata Blanco.The method can obtain higher Hesperidin yield, and in products obtained therefrom, the content of Hesperidin is higher; The reagent toxicity adopting in whole method is low, little to human health damage.
The method of extracting Hesperidin from peel of Citrus reticulata Blanco of the present invention, comprise alcohol extracting, macroporous resin column chromatography on alcohol extract, the step of elutriant crystallization and recrystallization, unlike the prior art: the step that also comprised water extraction removal of impurities before extraction step, specifically peel of Citrus reticulata Blanco is added to water lixiviate 1～3h under normal temperature condition, filter, collect the alcohol extracting operation that peel of Citrus reticulata Blanco carries out next step.By peel of Citrus reticulata Blanco first by flooding and discard the operation of water extraction liquid, can remove water-soluble impurity too much in peel of Citrus reticulata Blanco, greatly reduced the burden of postorder purification procedures, made the follow-up product that extracts gained by low-carbon alcohol than the removal of impurity not simultaneously and directly by low-carbon alcohol, extract that the content of hesperidin of products obtained therefrom is higher, yield is higher.
The above-mentioned method of extracting Hesperidin from peel of Citrus reticulata Blanco, specifically comprises the following steps:
1) take peel of Citrus reticulata Blanco as raw material, add water lixiviate 1～3h under normal temperature condition, filter, discard filtrate, collect peel of Citrus reticulata Blanco;
2) by step 1) peel of Citrus reticulata Blanco of gained extracts by the low-carbon alcohol of 60～80v/v%, collects extracting solution;
3) extracting solution is concentrated into the medicinal extract without alcohol taste, crosses nonpolar or low-pole macroporous resin column after dilute with water, first washes resin column to effluent liquid with water and clarifies, and then uses the low-carbon alcohol wash-out of 60～80v/v%, collects the alcohol eluen containing target component;
4) alcohol eluen is concentrated, standing crystallization, collects coarse crystal;
5) coarse crystal dissolves by 50～65v/v% low-carbon alcohol, adds activated carbon decolorizing, filters, and cooling recrystallization, collects crystal, dry, obtains Hesperidin.
In aforesaid method,
Step 1), in, the add-on of water is generally 5～8 times of raw material weight.Described normal temperature refers to the scope of 10～30 ℃.
Step 2) in, the operation of extracting by low-carbon alcohol is same as the prior art, can be refluxing extraction, supersound extraction or microwave extraction, preferably adopt refluxing extraction, the number of times of refluxing extraction is generally 1～3 time, each 1～2h that extracts, while extracting, the add-on of low-carbon alcohol is generally 5～10 times of raw material weight at every turn.
Step 3), in, the model of described nonpolar or low-pole macroporous resin is HPD-100, D-101, LX-21 or AB-8 etc.In the process of wash-out, adopting thin-layer chromatography (TLC) to follow the tracks of detects.In this step, after conventionally with the water that is equivalent to 4～8 times of medicinal extract, medicinal extract being diluted after nonpolar or low-pole macroporous resin column.
Step 4), in, normally alcohol eluen is concentrated into medicinal extract (15～20 Baume) and carries out standing crystallization.
Step 5), in, the consumption of gac (g) is generally 0.3～0.5% of the solvent volume (mL) used in recrystallization process.
In aforesaid method, described low-carbon alcohol is methyl alcohol or ethanol.
Compared with prior art, feature of the present invention is:
1, by peel of Citrus reticulata Blanco first by flooding and discard the operation of water extraction liquid, can remove water-soluble impurity too much in peel of Citrus reticulata Blanco, greatly reduce the burden of postorder purification procedures, made the follow-up product that extracts gained by low-carbon alcohol than the removal of impurity not and directly by low-carbon alcohol, to extract the content of hesperidin of products obtained therefrom higher simultaneously.
2, after alcohol extract concentration and recovery alcohol, dilute with water enters purification with macroreticular resin, can remove most of impurity, is convenient to follow-up crystallization operation, makes yield higher.
Embodiment
With specific embodiment, the invention will be further described below, but the present invention is not limited to these embodiment.
The concentration of the methyl alcohol described in following embodiment or ethanol is volumetric concentration.
Peel of Citrus reticulata Blanco described in following embodiment is dried peel of Citrus reticulata Blanco.
Embodiment 1
1) particle that is 0.2～0.5cm by peel of Citrus reticulata Blanco coarse reduction to diameter or filament shape, as raw material for standby; After testing, in raw material, the content of Hesperidin is 3.1% (HPLC method, lower same);
2) take 200kg raw material and be placed in extractor, add the aqueous solution of 5 times of raw material weights, room temperature condition stirs and extracts 2h, filters, and discards aqueous extract, leaves peel of Citrus reticulata Blanco;
3), to 60% ethanol that adds 5 times of raw material weights in extractor, refluxing extraction 2h, filters, and collects filtrate; Filter residue adds 60% ethanol of 5 times of raw material weights again, and refluxing extraction 2h filters, and collects filtrate; Merging filtrate, obtains extracting solution;
4) extracting solution concentration and recovery ethanol, obtains the medicinal extract without alcohol taste, thin up, enter HPD-100 macroporous adsorbent resin column chromatography, first wash resin column with water until effluent liquid is limpid, then use 65% ethanol elution, thin-layer chromatography is followed the tracks of and is detected, and collects the alcohol eluen containing target component;
5) by the alcohol eluen vacuum concentration of collecting to medicinal extract (15 Baume), cooling standing crystallization, filters, and collects crystal;
6) by step 5) the 50% ethanol heating for dissolving for coarse crystal of collecting, add activated carbon decolorizing, remove by filter gac, filtrate lets cool standing crystallization, filters, and collects and obtains white crystal, crystal vacuum-drying, obtain amorphous powder crystal 4.69kg, through HPLC, surveying content of hesperidin is 96.23% (HPLC method, lower same).
Comparative example 1
1) particle that is 0.2～0.5cm by peel of Citrus reticulata Blanco coarse reduction to diameter or filament shape, as raw material for standby; After testing, in raw material, the content of Hesperidin is 3.1%;
2) take 200kg raw material and be placed in extractor, to 60% ethanol that adds 5 times of raw material weights in extractor, refluxing extraction 2h, filters, and collects filtrate; Filter residue adds 60% ethanol of 5 times of raw material weights again, and refluxing extraction 2h filters, and collects filtrate; Merging filtrate, obtains extracting solution;
3) extracting solution concentration and recovery ethanol, obtains the medicinal extract without alcohol taste, thin up, enter HPD-100 macroporous adsorbent resin column chromatography, first wash resin column with water until effluent liquid is limpid, then use 65% ethanol elution, thin-layer chromatography is followed the tracks of and is detected, and collects the alcohol eluen containing target component;
4) by the alcohol eluen vacuum concentration of collecting to medicinal extract (15 Baume), cooling standing crystallization, filters, and collects crystal;
5) by step 4) the 50% ethanol heating for dissolving for coarse crystal of collecting, add activated carbon decolorizing, remove by filter gac, filtrate lets cool standing crystallization, filters, and collects and obtains white crystal, crystal vacuum-drying, obtains amorphous powder crystal 4.02kg, and through HPLC, surveying content of hesperidin is 94.71%.
Embodiment 2
1) particle that is 0.2～0.5cm by peel of Citrus reticulata Blanco coarse reduction to diameter or filament shape, as raw material for standby; After testing, in raw material, the content of Hesperidin is 3.4%;
2) take 300kg raw material and be placed in extractor, add the water of 7 times of raw material weights, room temperature condition stirs and extracts 1.5h, filters, and discards aqueous extract, leaves peel of Citrus reticulata Blanco;
3), to 75% methanol-water that adds 6 times of raw material weights in extractor, refluxing extraction 2h, filters, and collects filtrate; Filter residue adds 75% methyl alcohol of 6 times of raw material weights again, and refluxing extraction 2h filters, and collects filtrate; Merging filtrate, obtains extracting solution;
4) extracting solution concentration and recovery methyl alcohol, obtains the medicinal extract without alcohol taste, thin up, enter D-101 macroporous adsorbent resin column chromatography, first wash resin column with water until effluent liquid is limpid, then use 80% methanol-eluted fractions, thin-layer chromatography is followed the tracks of and is detected, and collects the alcohol eluen containing target component;
5) by the alcohol eluen vacuum concentration of collecting to medicinal extract (17 Baume), cooling standing crystallization, filters, and collects crystal;
6) by step 5) the 60% methanol solution heating for dissolving for coarse crystal of collecting, add activated carbon decolorizing, remove by filter gac, filtrate lets cool standing crystallization, filter, collect and obtain white crystal, crystal vacuum-drying, obtain amorphous powder crystal 7.97kg, through HPLC, surveying content of hesperidin is 97.62%.
Embodiment 3
1) particle that is 0.2～0.5cm by peel of Citrus reticulata Blanco coarse reduction to diameter or filament shape, as raw material for standby; After testing, in raw material, the content of Hesperidin is 2.7%;
2) take 150kg raw material and be placed in extractor, add the water of 6 times of raw material weights, normal temperature condition stirs and extracts 1h, filters, and discards aqueous extract, leaves peel of Citrus reticulata Blanco;
3) to 70% ethanol that adds 5 times of raw material weights in extractor, insulation refluxing extraction 2h, filters, and collects filtrate, and peel of Citrus reticulata Blanco adds 70% ethanol of 5 times of raw material weights again, and insulation refluxing extraction 2h, filters, and collects filtrate, and merging filtrate, obtains extracting solution;
4) extracting solution concentration and recovery ethanol, obtains the medicinal extract without alcohol taste, thin up, enter LX-21 macroporous adsorbent resin column chromatography, first wash resin column with water until effluent liquid is limpid, then the ethanol elution that is 70% by volumetric concentration, thin-layer chromatography is followed the tracks of and is detected, and collects the alcohol eluen containing target component;
5) by the alcohol eluen vacuum concentration of collecting to medicinal extract (16 Baume), cooling standing crystallization, filters, and collects crystal;
6) by step 5) the 55% ethanolic soln heating for dissolving for coarse crystal of collecting, add activated carbon decolorizing, remove by filter gac, filtrate lets cool standing crystallization, filter, collect and obtain white crystal, crystal vacuum-drying, obtain amorphous powder crystal 3.04kg, through HPLC, surveying content of hesperidin is 95.81%.
Embodiment 4
1) particle that is 0.2～0.5cm by peel of Citrus reticulata Blanco coarse reduction to diameter or filament shape, as raw material for standby; After testing, in raw material, the content of Hesperidin is 2.9%;
2) take 200kg raw material and be placed in extractor, add the water of 8 times of raw material weights, normal temperature condition stirs and extracts 2h, filters, and discards aqueous extract, leaves peel of Citrus reticulata Blanco;
3) to 80% ethanol that adds 10 times of raw material weights in extractor, insulation refluxing extraction 2h, filters, and filtrate is extracting solution;
4) extracting solution concentration and recovery ethanol, obtains the medicinal extract without alcohol taste, thin up, enter AB-8 macroporous adsorbent resin column chromatography, first wash resin column with water until effluent liquid is limpid, then the ethanol elution that is 65% by volumetric concentration, thin-layer chromatography is followed the tracks of and is detected, and collects the alcohol eluen containing target component;
5) by the alcohol eluen vacuum concentration of collecting to medicinal extract (20 Baume), cooling standing crystallization, filters, and collects crystal;
6) by step 5) the 60% ethanolic soln heating for dissolving for coarse crystal of collecting, add activated carbon decolorizing, remove by filter gac, filtrate lets cool standing crystallization, filter, collect and obtain white crystal, crystal vacuum-drying, obtain amorphous powder crystal 4.39kg, through HPLC, surveying content of hesperidin is 95.22%.
Claims (5)
1. from peel of Citrus reticulata Blanco, extract the method for Hesperidin, comprise alcohol extracting, macroporous resin column chromatography on alcohol extract, the step of elutriant crystallization and recrystallization, it is characterized in that: the step that also comprised water extraction removal of impurities before extraction step, specifically peel of Citrus reticulata Blanco is added to water lixiviate 1～3h under normal temperature condition, filter, collect the alcohol extracting operation that peel of Citrus reticulata Blanco carries out next step.
2. the method for extracting Hesperidin from peel of Citrus reticulata Blanco according to claim 1, is characterized in that: specifically comprise the following steps:
1) take peel of Citrus reticulata Blanco as raw material, add water lixiviate 1～3h under normal temperature condition, filter, discard filtrate, collect peel of Citrus reticulata Blanco;
2) by step 1) peel of Citrus reticulata Blanco of gained extracts by the low-carbon alcohol of 60～80v/v%, collects extracting solution;
3) extracting solution is concentrated into the medicinal extract without alcohol taste, crosses nonpolar or low-pole macroporous resin column after dilute with water, first washes resin column to effluent liquid with water and clarifies, and then uses the low-carbon alcohol wash-out of 60～80v/v%, collects the alcohol eluen containing target component;
4) alcohol eluen is concentrated, standing crystallization, collects coarse crystal;
5) coarse crystal dissolves by 50～65v/v% low-carbon alcohol, adds activated carbon decolorizing, filters, and cooling recrystallization, collects crystal, dry, obtains Hesperidin.
3. the method for extracting Hesperidin from peel of Citrus reticulata Blanco according to claim 2, is characterized in that: described low-carbon alcohol is methyl alcohol or ethanol.
4. the method for extracting Hesperidin from peel of Citrus reticulata Blanco according to claim 2, is characterized in that: step 1) in, the add-on of water is raw material weight 5～8 times.
5. the method for extracting Hesperidin from peel of Citrus reticulata Blanco according to claim 2, is characterized in that: step 3) in, the model of described nonpolar or low-pole macroporous resin is HPD-100, D-101, LX-21 or AB-8.
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Cited By (9)
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| CN104958582A (en) * | 2015-06-09 | 2015-10-07 | 徐蒙蒙 | Lophatherum gracile extract product, preparation containing extract product, and use of extract product |
| CN105294792A (en) * | 2014-07-11 | 2016-02-03 | 漳州开发区欧中农业技术研发有限公司 | Method for extraction and purification of hesperidin from tangelo peel |
| CN105418705A (en) * | 2015-12-08 | 2016-03-23 | 桂林三宝生物科技有限公司 | Method for extracting hesperidin and neohesperidin from citrus peels and fruits |
| 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 |
| CN105497622A (en) * | 2015-12-24 | 2016-04-20 | 杭州研谱科技有限公司 | Method for extracting tricin from corn bracts |
| CN105837646A (en) * | 2015-01-16 | 2016-08-10 | 刘力 | Flavonoid new chemical entity, composition and use |
| CN106146582A (en) * | 2016-07-18 | 2016-11-23 | 唐翔 | A kind of method using micro-cutting to help interaction technology assisted extraction Hesperidin |
| CN109180747A (en) * | 2018-11-26 | 2019-01-11 | 张家界继源科技有限公司 | A kind of extracting method of aurantiamarin |
| CN115558003A (en) * | 2022-09-30 | 2023-01-03 | 台州学院 | Method for extracting citrus essential oil and hesperidin from citrus peel |
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Cited By (13)
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| CN105294792A (en) * | 2014-07-11 | 2016-02-03 | 漳州开发区欧中农业技术研发有限公司 | Method for extraction and purification of hesperidin from tangelo peel |
| CN105294792B (en) * | 2014-07-11 | 2019-12-13 | 漳州开发区欧中农业技术研发有限公司 | Method for extracting and purifying hesperidin from citrus grandis pericarp |
| CN105837646A (en) * | 2015-01-16 | 2016-08-10 | 刘力 | Flavonoid new chemical entity, composition and use |
| CN104958582A (en) * | 2015-06-09 | 2015-10-07 | 徐蒙蒙 | Lophatherum gracile extract product, preparation containing extract product, and use of extract product |
| CN105418705A (en) * | 2015-12-08 | 2016-03-23 | 桂林三宝生物科技有限公司 | Method for extracting hesperidin and neohesperidin from citrus peels and fruits |
| 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 |
| CN105418705B (en) * | 2015-12-08 | 2018-11-02 | 周治德 | The method that aurantiamarin and neohesperidin are extracted from orange peel, fruit |
| CN105481920B (en) * | 2015-12-08 | 2018-11-23 | 周治德 | A method of extracting aurantiamarin, neohesperidin and synephrine |
| CN105497622B (en) * | 2015-12-24 | 2019-08-09 | 杭州研谱科技有限公司 | A method of extracting Tricin from corn bract |
| CN105497622A (en) * | 2015-12-24 | 2016-04-20 | 杭州研谱科技有限公司 | Method for extracting tricin from corn bracts |
| CN106146582A (en) * | 2016-07-18 | 2016-11-23 | 唐翔 | A kind of method using micro-cutting to help interaction technology assisted extraction Hesperidin |
| CN109180747A (en) * | 2018-11-26 | 2019-01-11 | 张家界继源科技有限公司 | A kind of extracting method of aurantiamarin |
| CN115558003A (en) * | 2022-09-30 | 2023-01-03 | 台州学院 | Method for extracting citrus essential oil and hesperidin from citrus peel |
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Application publication date: 20140226 |