CN101265283A - Method for extracting hesperidin and naringin - Google Patents
Method for extracting hesperidin and naringin Download PDFInfo
- Publication number
- CN101265283A CN101265283A CNA2008100364981A CN200810036498A CN101265283A CN 101265283 A CN101265283 A CN 101265283A CN A2008100364981 A CNA2008100364981 A CN A2008100364981A CN 200810036498 A CN200810036498 A CN 200810036498A CN 101265283 A CN101265283 A CN 101265283A
- Authority
- CN
- China
- Prior art keywords
- naringin
- extraction
- hesperidin
- sample
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Landscapes
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
Abstract
The invention relates to a method for extracting hesperidin and naringin by microwave-assisted extraction (MAE), which belongs to the field of analytical chemistry. The method includes quantitatively weighing sample, extracting hesperidin and naringin from the sample in mixed solvent of water and organic solvent in a microwave-assisted extraction device by selecting microwave power and extraction time through MAE, centrifuging, collecting the supernatant, diluting, and analyzing and measuring the content of hesperidin and naringin by HPLC. The method is simple and rapid, and has less sample usage amount, good repeatability, and high recovery rate. The method in combination with the HPLC can be used for accurately measuring the content of hesperidin and naringin in fruit juice, fresh fruit and Chinese traditional medicine, and evaluating quality thereof.
Description
Technical field
The invention belongs to the analytical chemistry field, relate to the method for extracting Hesperidin and naringin, be specifically related to a kind of method of utilizing the microwave auxiliary extraction technology to extract Hesperidin and naringin.
Background technology
Hesperidin (Hesperidin) is a kind of bulk drug that extracts from the dried immature fruit of citron orange, belong to vitamin drug, can reduce the fragility and the permeability of capillary vessel, the assisting therapy that is used for essential hypertension and capillary hemorrhage illness, reduction has improvement effect (strengthening ascorbic effect) to capillary resistance, has anti-inflammatory, antivirus action, is the medicine of treatment hypertension and myocardial infarction, being used as the raw material of pharmacy in the medicine industry, is one of main composition of Chinese patent medicine Maitong; Naringin (Naringin) is a kind of flavanone compounds.Naringin shows various biological activity and pharmacological action, has antibiotic, anti-inflammatory, anticancer, spasmolysis and choleretic effect, also can be used as the spice additive in the food.Epidemiological study shows that often edible shaddock class can play the effect of excellent protection blood vessel, prevention coronary heart disease.
Known Hesperidin is present in the various plants, and (Chinese medicine dried orange peel) content is especially abundant in the pericarp of rue family citrus plant, has the effect that regulating qi-flowing for strengthening spleen, clearing damp reduce phlegm, and the traditional Chinese medical science is usually used in treating illnesss such as chest gastral cavity turgor, the few vomiting and diarrhoea of food, coughing with a lot of sputum; Naringin mainly is present in rutaceae natsudaidai, from shaddock, recklessly the fruit of shaddock, also be herbal medicine Rhizome of Fortune's Drynaria, the dried immature fruit of citron orange, Fructus Aurantii, tangerine main effective constituent.The fruit juice kind reaches the hundreds of kind in the market, and wherein major part is an orange juice class drink.This area judges that one of main standard of orange juice drink quality is the content of its fresh orange-juice, and one of main standard of judging Fructus Citri grandis juice drink quality is the content of its grape-fruit juice.Therefore, the extraction and analysis of Hesperidin and naringin can be used for estimating the quality of fruit juice, new orange shaddock class fruit and Chinese medicine.
Microwave auxiliary extraction (MAE) is a technology of extracting the soluble material in the plant with micro-wave energy, mainly carries out in organic solvent.Microwave has very strong penetration power, can simultaneously evenly, promptly add heat energy in material inside and outside and make cell rupture, and effective constituent freely flows out in the born of the same parents, and it is dissolved to be delivered to surrounding medium.Compare with traditional extraction technology, MAE has advantages such as extraction yield height, extraction time is short, amount of samples is few.
At present, the method that being used to of existing report extracted Hesperidin and naringin only is organic solvent extraction method or ultrasonic extraction, there is following defective in described method: big, the consuming time length of consumption of organic solvent, extraction efficiency are low, the described method of simple use is difficult to Hesperidin in fruit juice, fruit or the Chinese medicine and naringin are extracted fully, is unfavorable for further content analysis and mensuration.Therefore this area need be set up one fast, and is simple, and efficient, reliable extracting method is convenient to the content of Hesperidin in the different media and naringin is carried out compartment analysis.
Summary of the invention
The objective of the invention is to overcome the defective of prior art, the extracting method of a kind of Hesperidin and naringin is provided, relate to the method for from solid-state or semi-solid state or liquid testing sample, extracting Hesperidin and naringin.Especially from pericarp, pulp and the Chinese medicine of fruit juice, fresh fruit, extract the method for Hesperidin and naringin.
Hesperidin and naringin in pericarp, pulp or the Chinese medicine of present method employing microwave auxiliary extraction technology extraction fruit juice, fresh fruit, easy, fast, amount of samples is few, extraction efficiency height, favorable reproducibility, rate of recovery height.
Present method combines with high performance liquid chromatography, can accurately measure the content of Hesperidin and naringin, estimates the quality of fruit juice, fruit and Chinese medicine from certain angle.
Hesperidin of the present invention and naringin have the structural formula of Fig. 1.
Purpose of the present invention is achieved through the following technical solutions:
Sample is blended with pulverizer, the quantitative sampling product, put into reactor, after adding the extraction solvent, reactor is positioned in the microwave-assisted extraction device, selected extracts solvent, microwave power and after the extraction time, utilize MAE to extract Hesperidin and naringin in the sample, the extraction back is centrifugal, takes out supernatant liquor.
The described extraction solvent of the inventive method is the mixed solvent that water and organic solvent are formed, wherein water: the proportional range of organic solvent is 80: 20～20: 80.Described organic solvent is selected from methyl-sulphoxide, methyl alcohol, ethanol or acetonitrile.
The inventive method is according to the difference of survey product, adopt the corresponding consumption (envelope-bulk to weight ratio or volume volume ratio) that extracts solvent: when sample is solid-state or semi-solid state, during as Chinese medicine, fruit pericarp or pulp, the consumption (mL) that extracts solvent is 5-20 a times of sample size (g); When sample is liquid, during as fruit juice, the consumption (mL) that extracts solvent be sample size (mL) 2-10 doubly.
The influence factor of microwave auxiliary extraction of the present invention (MAE) extraction efficiency has the solvent types of extraction, volume, microwave power and microwave time.
In the method for said extracted Hesperidin of the present invention and naringin composition, the microwave power of use is 100～1000 watts.
In the method for said extracted Hesperidin of the present invention and naringin composition, the extraction time of use is 1～10 minute.
The screening that the present invention carries out influence factor by following test is definite,
1) selection of extraction solvent species:
Because water is microwave absorption best in the microwave extracting, therefore in the process of extracting solvent species optimization, the present invention selects the mixed solvent of organic solvent and water for use.Present method has been selected 50% methanol aqueous solution respectively for use, 40%, 50%, 55%, 60% the DMSO aqueous solution is as extracting solvent, under the identical situation of other experiment conditions, Determination of Hesperidin Content in extraction and the analytic sample, the result shows, the extraction yield of the DMSO aqueous solution during as solvent is far longer than methanol aqueous solution, wherein, 50% DMSO extraction with aqueous solution rate is better than 40%, 55% and 60% (Fig. 2), the preferred 50%DMSO aqueous solution of extraction solvent of the present invention.
2) selection of extraction quantity of solvent:
Extract Hesperidin in the Chinese medicine, take by weighing the about 1g of sample size and place reactor, use 5ml respectively, 10ml, the 50%DMSO aqueous solution of 20ml carries out microwave extraction, and the result shows, the extraction yield of the extraction solvent of 5ml and 10ml does not have obvious difference, when wherein adopting the 5ml solvent, sample segment zoom caking occurs; The phenomenon that solution is gone out prolong can occur when the solvent of 20ml carries out microwave, preferably extracting quantity of solvent is 10ml, is 10 times of sample size;
Extract Hesperidin and naringin in pulp and the pericarp, take by weighing about 1g pulp or pericarp and place reactor, the result shows that the amount of preferably extracting solvent is 5mL, is 5 times of sample size;
Extract Hesperidin and naringin in the fruit juice, measure the 1mL sample and place reactor, the result shows that the amount of preferably extracting solvent is 5mL, is 5 times of sample size.
3) microwave power and the selection of microwave time:
The result of Hesperidin shows in the said extracted Chinese medicine, and preferred extraction conditions is: extract power 400W, 3 minutes extraction times;
The result of Hesperidin and naringin shows in said extracted fruit juice, pulp or the pericarp, and preferred extraction conditions is: extract power 500W, 3 minutes extraction times;
After having compared microwave auxiliary extraction and supersound process extraction fruit juice and Chinese medicine sample respectively, Determination of Hesperidin Content with HPLC mensuration, the result shows, extract by microwave auxiliary extraction and to obtain Determination of Hesperidin Content and be higher than ultrasonic extraction (Fig. 3) far away, proof microwave extracting extraction yield height, and required time is short, and is with the obvious advantage.
The method that the present invention extracts Hesperidin and naringin composition is easy, accurate, reliable, and fast, amount of samples is few, the extraction efficiency height, and the extraction time is short, favorable reproducibility, rate of recovery height.This law combines with high performance liquid chromatography, can be used for accurately measuring the content of Hesperidin and naringin in fruit juice, fruit and the Chinese medicine, estimates their quality from certain angle.
Description of drawings
Fig. 1 is the structural formula of Hesperidin and naringin.
Fig. 2 is different the extraction under the solvent condition, the extracted amount disparity map of Hesperidin,
Wherein, 50% the DMSO aqueous solution is as extracting solvent, and its extraction yield is better than 40%, 55% and 60%.
Fig. 3 is the comparison diagram that ultrasonic extraction and microwave extraction method extract content of hesperidin in the fruit juice,
Wherein, extract by microwave auxiliary extraction and obtain Determination of Hesperidin Content and be higher than ultrasonic extraction far away.
Fig. 4 is a Determination of Hesperidin Content disparity map in the different brands fruit juice,
Wherein, Determination of Hesperidin Content is the highest in the NongFuGuoYuan board fruit juice, is about 0.4mg/ml, illustrates that the content of its raw material fresh orange-juice is the highest.
Fig. 5 is the content difference figure of naringin in the different brands fruit juice,
Wherein, the content of naringin is higher than the beauty-fruit board in the full board Fructus Citri grandis juice of distinguishing the flavor of, and is about 0.065mg/ml, and the content of its raw material grape-fruit juice is higher.
Embodiment
Embodiment 1 MAE-HPLC analyzes Determination of Hesperidin Content in the different brands orange juice
Instrument and material:
Instrument: Tianjin, island CL-10 type liquid chromatograph, comprise SPD-10A UV-detector and CTO-10A column oven, 20 μ L hand sampling systems, chromatographic working station, LWMC-205 type power-adjustable microwave chemical reactor, Millipore Direct-Q pure water generator.
Material: various brands orange juice drink.Methyl alcohol (Merck, chromatographically pure), trifluoroacetic acid and methyl-sulphoxide are analytical pure, and the deionization pure water is made by Millipore Direct-Q pure water generator, and the Hesperidin standard substance derive from Nat'l Pharmaceutical ﹠ Biological Products Control Institute.
Sample pre-treatments:
Respectively get 1ml fruit juice in the 50ml round-bottomed flask, add the 5ml 50%DMSO aqueous solution, jolting, at power is under the condition of 500W, and microwave extracting is after 3 minutes, and the centrifuging and taking supernatant liquid filtering dilutes the back sample introduction, get measurement result, show: Determination of Hesperidin Content is the highest in the NongFuGuoYuan board fruit juice, is about 0.4mg/ml, and the content the highest (Fig. 4) of its raw material fresh orange-juice is described.
Average recovery:
The accurate fruit juice 1ml that draws, the certain density quality control standard solution of the accurate adding of difference carries out microwave extracting according to sample preparation methods then, gets filtrate dilution back sample introduction and carries out the HPLC analysis, and average recovery rate is respectively: (99.81 ± 1.56) % (n=3).
Repeated experiment:
The accurate fruit juice 1ml that draws carries out microwave extracting according to sample preparation methods, gets filtrate dilution back sample introduction and carries out the HPLC analysis, and replication three times, RSD are 3.15%.
The content of Hesperidin and naringin in the embodiment 2 MAE-HPLC analysis grapefruit juice
Instrument and material:
Instrument: Tianjin, island CL-10 type liquid chromatograph, comprise SPD-10A UV-detector and CTO-10A column oven, 20 μ L hand sampling systems, chromatographic working station, LWMC-205 type power-adjustable microwave chemical reactor, Millipore Direct-Q pure water generator.
Material: the grapefruit orange juice mixing drink of 2 kinds of brands.Methyl alcohol (Merck, chromatographically pure), trifluoroacetic acid and methyl-sulphoxide are analytical pure, and the deionization pure water is made by Millipore Direct-Q pure water generator, and the Hesperidin standard substance derive from Nat'l Pharmaceutical ﹠ Biological Products Control Institute.
Sample pre-treatments:
Respectively get 1ml fruit juice in the 50ml round-bottomed flask, add the 5ml 50%DMSO aqueous solution, jolting.At power is under the condition of 500W, and microwave extracting is after 3 minutes, and the centrifuging and taking supernatant liquid filtering dilutes the back sample introduction, get measurement result, show that the content of naringin is higher than the beauty-fruit board in the full board Fructus Citri grandis juice of distinguishing the flavor of, be about 0.065mg/ml, the content of its raw material grape-fruit juice higher (Fig. 5).
Embodiment 3 MAE analyze content of hesperidin in the Chinese medicinal materials dried orange peel
Instrument and material:
Instrument: Tianjin, island CL-10 type liquid chromatograph, comprise SPD-10A UV-detector and CTO-10A column oven, 20 μ L hand sampling systems, chromatographic working station, LWMC-205 type power-adjustable microwave chemical reactor, Millipore Direct-Q pure water generator.
Material: the Chinese medicine dried orange peel (place of origin: Shanghai), methyl alcohol (Merck, chromatographically pure), trifluoroacetic acid and methyl-sulphoxide are analytical pure, the deionization pure water is made by Millipore Direct-Q pure water generator, and the Hesperidin standard substance derive from Nat'l Pharmaceutical ﹠ Biological Products Control Institute's (purity＞99%).
Sample pre-treatments:
Precision takes by weighing the about 1g of Dried Tangerine Peel, puts in the 50ml round-bottomed flask, adds the 10ml 50%DMSO aqueous solution, and microwave auxiliary extraction (power 400W) 3min is put coldly, and high speed centrifugation (10000rpm) 10min gets supernatant liquid filtering, gets 20 μ l sample introductions after the dilution.
Average recovery:
Precision takes by weighing the about 1.00g of dried orange peel sample, accurate respectively adding 100 μ L concentration are 14 μ g/ml quality control standard solution, carry out microwave extracting according to sample preparation methods then, get filtrate dilution back sample introduction and carry out the HPLC analysis, average recovery rate is respectively: (101.68 ± 0.21) % (n=3).
Repeatability and sample determination result:
Precision takes by weighing the about 1.00g of dried orange peel sample, carries out microwave extracting according to sample preparation methods, and get filtrate dilution back sample introduction and carry out the HPLC analysis, replication three times, Determination of Hesperidin Content is in the Chinese medicine dried orange peel: (54.10 ± 1.17) mg/g, RSD are 2.16%.With content of hesperidin close (being about 4% in the document) in the Chinese medicine dried orange peel of bibliographical information, reliable results.
Claims (7)
1, a kind of method of extracting Hesperidin and naringin is characterized in that by following step:
1) get testing sample, add and extract solvent, described extraction solvent is the mixed solvent that water and organic solvent are formed, and wherein, the ratio of water and organic solvent is 80: 20～20: 80;
2) be positioned over and carry out microwave extracting in the microwave-assisted extraction device, wherein, microwave power is 100～1000 watts, and the extraction time is 1～10 minute;
3) the extraction back is centrifugal, takes out supernatant liquor.
2, the extracting method of Hesperidin according to claim 1 and naringin is characterized in that: the organic solvent of described step 1 is selected from methyl-sulphoxide, methyl alcohol, ethanol or acetonitrile.
3, the extracting method of Hesperidin according to claim 1 and naringin is characterized in that described extraction solvent is 50% the methyl-sulphoxide aqueous solution.
4, the extracting method of Hesperidin according to claim 1 and naringin is characterized in that described testing sample is solid-state or semi-solid state or liquid state, and the 5-20 that described extraction solvent load solid-state or the semi-solid state sample is a sample size doubly; The consumption of the extraction solvent of described liquid sample is a sample size) 2-10 doubly.
5, the extracting method of Hesperidin according to claim 4 and naringin is characterized in that described solid-state or semi-solid state sample is selected from Chinese medicine, fruit pericarp or pulp; Described liquid sample is selected from fruit juice.
6, the extracting method of Hesperidin according to claim 5 and naringin is characterized in that the extraction conditions of described Chinese medicine sample is: extract power 400W, 3 minutes extraction times.
7, the extracting method of Hesperidin according to claim 5 and naringin is characterized in that: the extraction conditions of described fruit juice, pulp and pericarp is: extract power 500W, 3 minutes extraction times.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100364981A CN101265283A (en) | 2008-04-22 | 2008-04-22 | Method for extracting hesperidin and naringin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100364981A CN101265283A (en) | 2008-04-22 | 2008-04-22 | Method for extracting hesperidin and naringin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101265283A true CN101265283A (en) | 2008-09-17 |
Family
ID=39987994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008100364981A Pending CN101265283A (en) | 2008-04-22 | 2008-04-22 | Method for extracting hesperidin and naringin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101265283A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101704867B (en) * | 2009-11-03 | 2012-02-01 | 国家海洋局第三海洋研究所 | Method for preparing naringin or hesperidin |
| CN102524786A (en) * | 2012-02-10 | 2012-07-04 | 中南林业科技大学 | Processing method of nutritional buccal tablets of orange peels |
| CN103113438A (en) * | 2013-01-30 | 2013-05-22 | 唐忠海 | Method for extracting hesperidin and orange peel uranidin from orange peel |
| CN103961442A (en) * | 2014-04-30 | 2014-08-06 | 桂林军供生化技术开发有限公司 | Method for extracting pomelo polyphenols from pomelo peel |
| CN107137524A (en) * | 2017-04-20 | 2017-09-08 | 广东暨晴生物医药科技有限公司 | A kind of compound essential oil refreshed the mind and preparation method thereof |
| CN107349214A (en) * | 2017-07-28 | 2017-11-17 | 广东工业大学 | A kind of pharmaceutical composition and its application |
| CN111869751A (en) * | 2020-06-24 | 2020-11-03 | 阜阳天祥食品科技有限公司 | Blended edible oil and preparation method thereof |
-
2008
- 2008-04-22 CN CNA2008100364981A patent/CN101265283A/en active Pending
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101704867B (en) * | 2009-11-03 | 2012-02-01 | 国家海洋局第三海洋研究所 | Method for preparing naringin or hesperidin |
| CN102524786A (en) * | 2012-02-10 | 2012-07-04 | 中南林业科技大学 | Processing method of nutritional buccal tablets of orange peels |
| CN102524786B (en) * | 2012-02-10 | 2013-01-16 | 中南林业科技大学 | Processing method of nutritional buccal tablets of orange peels |
| CN103113438A (en) * | 2013-01-30 | 2013-05-22 | 唐忠海 | Method for extracting hesperidin and orange peel uranidin from orange peel |
| CN103113438B (en) * | 2013-01-30 | 2016-01-06 | 吉首大学 | A kind of method from Extracting Hesperidin from Orange Peel and Yellow Pigment in Tangerine Peel |
| CN103961442A (en) * | 2014-04-30 | 2014-08-06 | 桂林军供生化技术开发有限公司 | Method for extracting pomelo polyphenols from pomelo peel |
| CN107137524A (en) * | 2017-04-20 | 2017-09-08 | 广东暨晴生物医药科技有限公司 | A kind of compound essential oil refreshed the mind and preparation method thereof |
| CN107349214A (en) * | 2017-07-28 | 2017-11-17 | 广东工业大学 | A kind of pharmaceutical composition and its application |
| CN107349214B (en) * | 2017-07-28 | 2020-07-10 | 广东工业大学 | Pharmaceutical composition and application thereof |
| CN111869751A (en) * | 2020-06-24 | 2020-11-03 | 阜阳天祥食品科技有限公司 | Blended edible oil and preparation method thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101265283A (en) | Method for extracting hesperidin and naringin | |
| del Campo et al. | Quantitative determination of caffeine, formic acid, trigonelline and 5-(hydroxymethyl) furfural in soluble coffees by 1H NMR spectrometry | |
| CN107843677A (en) | Radix paeoniae rubrathe reference extract and its preparation method and application | |
| CN105203657A (en) | Spina date seed reference extract and preparation method and application thereof | |
| CN105651899A (en) | Method for high-sensitivity detection of aflatoxin and application of aflatoxin | |
| CN105699500A (en) | A method of measuring contents of seven components in a Huoxiangzhengqi dripping pill through ultra-high performance liquid chromatography | |
| CN104330482B (en) | A kind of HPLC of utilization measures the method for 17 kinds of characteristic components in Folium Camelliae sinensis simultaneously | |
| CN105486766A (en) | Method for determining content of three antioxidation active compositions in honeysuckle flower and plant thereof by employing HPLC | |
| CN101810696B (en) | Total triterpenoids of apples and method for preparing same | |
| CN108037200B (en) | Quality detection method of kidney nourishing and tranquilizing pills | |
| CN104181269B (en) | The method of Bee Pollen is differentiated based on Kaempferol 3-O-β-D-Glucose-(2 → 1)-β-D-Glucose glycosides | |
| CN108828111A (en) | The content assaying method of diet polyphenol in a kind of walnut kernel | |
| CN103822888B (en) | Catch up with the quality determining method of yellow grass | |
| CN101169394A (en) | Cosmetic product clindamycinum high efficiency liquid chromatography detection method | |
| CN103512975A (en) | Method for analyzing contents of effective substances in Cordyceps martialis fruiting body and residue by HPLC | |
| CN103808751A (en) | Method for identifying lonicera japonica medicinal material or derivatives of lonicera japonica medicinal material | |
| CN103983714B (en) | A kind of method measuring cumarin and safrole content in tobacco product | |
| CN105628825A (en) | Method for measuring contents of four main monosaccharides and disaccharides in honey on basis of UPC2-ELSD | |
| CN106093264A (en) | A kind of assay method of Fructus Fragariae Ananssae Xanthophyll Cycle Components | |
| CN104849372A (en) | Method for measuring formaldehyde content in vegetables and fruits | |
| CN104280497A (en) | Method for detecting quality of two flavones in fructus aurantii | |
| CN114487231A (en) | HPLC synchronous determination method and application of twelve ginsenosides in panax notoginseng stems and leaves | |
| CN101549081B (en) | Method of quality control for smilax china | |
| CN100518798C (en) | Dispersible tablet with gastrodia tuber for treating headache, and its testing method | |
| CN109709226A (en) | A method of trans-resveratrol content in measurement peanut dry seeds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Open date: 20080917 |