CN102827220A - Method for separating rutin, hyperoside, isoquercitrin and quercetin from lotus leaves - Google Patents
Method for separating rutin, hyperoside, isoquercitrin and quercetin from lotus leaves Download PDFInfo
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Abstract
The invention relates to the technical field of traditional Chinese medicine, especially to a method for separating rutin, hyperoside, isoquercitrin and quercetin from lotus leaves. The method for separating the rutin, the hyperoside, the isoquercitrin and the quercetin from the lotus leaf comprises separating components in the lotus leaves powder by using a column chromatography method for a gradient elution for 65 to 75 minutes with a flow rate of 0.6 to 0.8 ml/min under a temperature of 28 to 32 DEG C and a pH value of 3.5 to 4.5, wherein a stationary phase of the column chromatography is C18, a mobile phase A is a phosphatic buffer with a pH value of 3.5 to 4.5, a mobile phase B is acetonitrile, and the outflow components are successively the rutin, the hyperoside, the isoquercitrin and the quercetin according to a time sequence; respectively recovering eluents containing the rutin, the hyperoside, the isoquercitrin and the quercetin; and finally removing solvents with reduced pressure distillation to obtain the rutin, the hyperoside, the isoquercitrin and the quercetin. The method not only can separate the rutin, the hyperoside, the isoquercitrin and the quercetin, but also is high is separation efficiency.
Description
Technical field
The present invention relates to technical field of traditional Chinese medicines, relate in particular to a kind of method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin.
Background technology
Lotus leaf is the dry leave of water lily plant lotus (Nelumbo nucifera Gaertn); Have another name called lotus leaf, lotus root leaf; Most of areas has plantation more in China, is widely used in food and medicine, is the kind of second batch of Ministry of Health regulation " be food be again medicine ".Traditional medicine is thought, the lotus leaf bitter is flat, returns liver, spleen, stomach warp; Effect with clearing away summer-heat and eliminating dampness, sending up the lucid YANG, cooling blood for hemostasis is according to Compendium of Material Medica record " the lotus leaf clothes, make us thin bad ", " hair tonic vigour, benefit helps taste; puckery essence is turbid, the hemostasis that looses, detumescence pain, a variola ".Modern medicine study proves, contains a large amount of flavonoid compounds in the lotus leaf, has reducing blood-fat, treatment atherosclerosis, antimitotic, effect such as antibacterial.
At present, the existing report of the mensuration of flavones content adopts flavonoid contents such as ultraviolet spectrometry range method mensuration total flavones or high effective liquid chromatography for measuring Quercetin, rutin more in the lotus leaf.
The isoquercitrin of the certain content of tool in the lotus leaf, but because flavonoid compound structural similitudies such as isoquercitrin and rutin, Quercetin, ordinary method is difficult to effectively separate.
CN100367976 (2008-2-13) provide a kind of Herba Hyperici perforati extract and preparation method, wherein relates to the peak area of isoquercitrin and the fingerprint atlas detection method of Herba Hyperici perforati extract, yet this method is also inapplicable for from lotus leaf, separating.
" pharmaceutical analysis impurity " 2010; 30 Yuan Li spring; That Liu Bin, Shi Renbing disclose is a kind of " the HPLC method is measured the content of Quercetin 3-galactoside and isoquercitrin in the different commercially available lotus leaf medicinal materials ", yet this method is the routine analysis method of purification; Separation efficiency is not high, and is difficult to respectively Quercetin, rutin, Quercetin 3-galactoside and isoquercitrin separated.
Summary of the invention
The purpose of this invention is to provide the high a kind of method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin of a kind of separation efficiency.
Above-mentioned technical purpose of the present invention is achieved through following technical scheme: a kind of method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin; Comprise and adopt column chromatography method to split the component in the Lotus Leaf; And the stationary phase that column chromatography uses is C18; Mobile phase A is the phosphate buffered saline buffer of pH value 3.5-4.5, and Mobile phase B is an acetonitrile, under column temperature 28-32 ℃, the condition of pH value 3.5-4.5, presses the current gradient wash-out 65-75min of 0.6-0.8ml/min; Said condition of gradient elution is: at 0-45min, the volume ratio of said mobile phase A and Mobile phase B is (90-95)/(5-10); At 46-55min, the volume ratio of said mobile phase A and Mobile phase B is (80-85)/(15-20); At 56-65min, the volume ratio of said mobile phase A and Mobile phase B is (68-72)/(28-32); At 66-75min, the volume ratio of said mobile phase A and Mobile phase B is (90-95)/(5-10); Reclaim the elutriant that contains rutin, Quercetin 3-galactoside, isoquercitrin, Quercetin respectively, obtain rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin after last underpressure distillation removes solvent.
Rutin, Quercetin 3-galactoside, isoquercitrin, Quercetin differ a glucosyl respectively, and the fixed proportion wash-out is difficult to separate, particularly rutin and isoquercitrin; RT is very approaching; Cause mixing easily,, finally realized effective separation through above-mentioned gradient separations method of the present invention; And the separation efficiency of rutin, Quercetin 3-galactoside, isoquercitrin, Quercetin reaches respectively more than 98.5%, and separation efficiency is higher.
As preferably, said phosphate buffered saline buffer is that the sodium hydroxide solution of phosphoric acid solution and the 8-12% of 0.15-0.25% is mixed to pH value 3.5-4.5 and is prepared from.
More preferably, the compound method of said phosphate buffered saline buffer is: the sodium hydroxide solution of phosphoric acid solution titration to 10% with 0.2%, add air through stirring simultaneously in titration, and be mixed to pH value 4.0 and be prepared from.
As preferably, the pH value of phosphate buffered saline buffer is 4.0.
As preferably, at 0-45min, the volume ratio of said mobile phase A and Mobile phase B is 92/8.
As preferably, at 46-55min, the volume ratio of said mobile phase A and Mobile phase B is 82/18.
As preferably, at 56-65min, the volume ratio of said mobile phase A and Mobile phase B is 70/30.
As preferably, at 66-75min, the volume ratio of said mobile phase A and Mobile phase B is 92/8.
As preferably, said Lotus Leaf uses earlier massfraction to be the dissolve with methanol solution of 75-85% ultrasonic 28-35min also, and then adds the dissolve with methanol solution after-filtration of 75-85%, gets the treat parting liquid of filtrating as said column chromatography.
More preferably, the first use of said Lotus Leaf massfraction is 80% dissolve with methanol solution and ultrasonic 30min, and then adds 80% dissolve with methanol solution after-filtration, gets the treat parting liquid of filtrating as said column chromatography.
Description of drawings
Fig. 1 is the color atlas of the embodiment of the invention one;
Fig. 2 is the color atlas of control substance of Rutin;
Fig. 3 is the color atlas of Quercetin 3-galactoside reference substance;
Fig. 4 is the color atlas of isoquercitrin reference substance;
Fig. 5 is the color atlas of Quercetin reference substance;
Among the figure, I-rutin; II-Quercetin 3-galactoside; III-isoquercitrin; IV-Quercetin.
Embodiment
Embodiment one
1 instrument and reagent
Agilent 1100 type high performance liquid chromatographs; Isoquercitrin reference substance (lot number is 10391, and purity is 93.0%, German HWI ANALYTIK company); Quercetin reference substance (lot number is 100081-200406, Nat'l Pharmaceutical & Biological Products Control Institute); Control substance of Rutin (lot number is 100080-200707, Nat'l Pharmaceutical & Biological Products Control Institute); Acetonitrile (chromatographically pure, German Merck company); Water is ultrapure water; The former powder of lotus leaf (sieve is plucked, dries, pulverizes, crossed in self-control, South Pacific lakeside No. 5); All the other reagent are analytical pure.
2 methods and result
2.1 chromatographic condition
Chromatographic column: 30 ℃ of Agilent C18 post (250mm * 4.6mm, 5 μ m) column temperatures.Mobile phase A: pH4.0 phosphate buffered saline buffer (0.2% phosphoric acid solution is regulated pH value to 4.0 with 10% sodium hydroxide solution); Mobile phase B: acetonitrile; Gradient elution sees table 1 for details.UV-detector detects, and detects wavelength 356nm.Sample size: 5 μ l.Theoretical plate number is not less than 2500 in isoquercitrin.
The compound method of phosphate buffered saline buffer is: the sodium hydroxide solution of phosphoric acid solution titration to 10% with 0.2%, add air through stirring simultaneously in titration, and be mixed to pH value 4.0 and be prepared from.
Under column temperature 28-32 ℃, the condition of pH value 3.5-4.5, press the current gradient wash-out 65-75min of 0.6-0.8ml/min; Effusive component is followed successively by rutin, Quercetin 3-galactoside, isoquercitrin, Quercetin according to time order and function; Reclaim the elutriant that contains rutin, Quercetin 3-galactoside, isoquercitrin, Quercetin respectively, obtain rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin after last underpressure distillation removes solvent.
Rutin yield is 96.8%, and purity reaches 90%; Radix Hyperici Monogyni (Herba Hyperici Monogyni)
GlycosidesYield is 97.6%, and purity reaches 88%; The isoquercitrin yield is 99.1%, and purity reaches 92%; The Quercetin yield is 98.1%, and purity reaches 91%.
Table 1 embodiment one gradient elution table
2.2 formulations prepared from solutions
Get the former powder 0.25g of lotus leaf, add 80% methyl alcohol 30ml, ultrasonic 30min adds 80% methyl alcohol to 50ml, shakes up, and filters, and gets filtrating as need testing solution (treating parting liquid).
Get isoquercitrin reference substance 0.00513g, add 80% methanol solution and be diluted to 50ml, mixing is made recovery test liquid; Fetch yield experimental liquid 5.00ml and put the 25ml measuring bottle, add 80% methyl alcohol to scale, mixing is as reference substance solution.
Get control substance of Rutin 0.00253g, add 80% methanol solution and be diluted to 100ml, mixing; Get Quercetin reference substance 0.00283g, add 80% methanol solution and be diluted to 100ml, mixing; As specificity experimental control liquid.
The same rutin of specificity experimental control liquid making method of Quercetin 3-galactoside, Quercetin.
2.3 methodological study
Specificity test: get reference substance solution, need testing solution, each 5 μ l of specificity experimental control liquid respectively, measure by above-mentioned chromatographic condition.The former powder collection of illustrative plates of lotus leaf sees Fig. 1 for details, and specificity test collection of illustrative plates sees Fig. 2, Fig. 3, Fig. 4 and Fig. 5 for details.
The result shows that there is chromatographic peak in place identical with the reference substance solution chromatographic retention in the need testing solution chromatogram, and specificity experimental control liquid effectively separates with the reference substance solution chromatogram under this chromatographic condition.
Linear relationship is investigated: by above-mentioned chromatographic condition; Reference substance solution sample size 2 μ l, 4 μ l, 8 μ l, 14 μ l, 20 μ l measure peak area, make typical curve with sample size (X) and peak area (Y); Get regression equation Y=48.82X-1.119; R=0.9990 (n=5), result show that the isoquercitrin sample size is good with the peak area linear relationship in 0.0382ng-0.382ng scope.
The precision test: the accurate isoquercitrin reference substance solution 10 μ l that draw, repeat sample introduction 6 times.The RSD=1.6% of results peaks area (n=6).
Replica test: take by weighing 6 parts in the former powder of lotus leaf (about 0.25g), prepare need testing solution in accordance with the law, measure by above-mentioned chromatographic condition.The RSD=0.56% of isoquercitrin content (n=6) as a result.
Stability test: get same need testing solution, respectively 0.5,2,4,8,12h measures.Peak area RSD=1.7% (n=6) shows that need testing solution is good at 12 hours internal stabilities.
The application of sample recovery test: get the former powder of lotus leaf (content 3.727mg/g) of known content, the accurate respectively isoquercitrin recovery test liquid that adds is an amount of, and press need testing solution preparation method preparation and measure content, calculate recovery rate, the result sees table 2.
Table 2 isoquercitrin application of sample recovery test result (n=6)
2.4 sample determination
Other gets 3 batches of former powder samples of lotus leaf, presses need testing solution preparation method operation, by 2.1 following chromatographic condition sample introductions, calculates content with external standard method.The result is: 3.567mg/g, 4.087mg/g, 2.908mg/g.
Embodiment two
With embodiment one, different is in different time, and the volume ratio of mobile phase A and Mobile phase B is that condition of gradient elution is seen table 3.Wherein phosphate buffered saline buffer is that the sodium hydroxide solution of 0.15% phosphoric acid solution and 8% is mixed to pH value 3.5 and is prepared from.Lotus Leaf elder generation use massfraction is 75% dissolve with methanol solution and ultrasonic 28min, and then adds 85% dissolve with methanol solution after-filtration, gets the treat parting liquid of filtrating as said column chromatography.
Recording rutin yield is 96.5%, and purity reaches 90.5%; The Quercetin 3-galactoside yield is 97.3%, and purity reaches 89%; The isoquercitrin yield is 99%, and purity reaches 92.3%; The Quercetin yield is 98.4%, and purity reaches 90.4%.
Table 3 embodiment two gradient elution tables
Embodiment three
With embodiment one, different is in different time, and the volume ratio of mobile phase A and Mobile phase B is that condition of gradient elution is seen table 4.
Recording rutin yield is 96.2%, and purity reaches 89.9%; The Quercetin 3-galactoside yield is 97.1%, and purity reaches 89.4%; The isoquercitrin yield is 98.9%, and purity reaches 91.8%; The Quercetin yield is 97.8%, and purity reaches 90.1%.
Table 4 embodiment three gradient elution tables
The comparative example one
With embodiment one.Different is chromatographic condition: chromatographic column: C
18Chromatographic column; Moving phase: acetonitrile-0.1% formic acid water (13:87); Flow velocity 1.0ml/min; Detect wavelength: 255nm; Column temperature: 34 ℃.
This method only can be separated Quercetin 3-galactoside and isoquercitrin.Recording the Quercetin 3-galactoside yield is 96.1%, purity 80%; The isoquercitrin yield is 98.8%, purity 75%.
The comparative example two
With embodiment two, different is by under the condition of 20 ℃ of column temperatures, pH value 6 by the 1.2ml/min gradient elution, elution requirement is seen table 5.
Table 5 comparative example two gradient elution tables
Recording rutin yield is 86.2%, and purity reaches 80.9%; The Quercetin 3-galactoside yield is 92.5%, and purity reaches 85.4%; The isoquercitrin yield is 94.9%, and purity reaches 81.8%; The Quercetin yield is 82.8%, and purity reaches 80%.
This specific embodiment only is to explanation of the present invention; It is not a limitation of the present invention; Those skilled in the art can make the modification that does not have creative contribution to present embodiment as required after reading this specification sheets, but as long as in claim scope of the present invention, all receive the protection of patent law.
Claims (10)
1. the method for from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin; Comprise and adopt column chromatography method to split the component in the Lotus Leaf; It is characterized in that: the stationary phase that said column chromatography uses is C18; Mobile phase A is the phosphate buffered saline buffer of pH value 3.5-4.5, and Mobile phase B is an acetonitrile, under column temperature 28-32 ℃, the condition of pH value 3.5-4.5, presses the current gradient wash-out 65-75min of 0.6-0.8ml/min; Said condition of gradient elution is: at 0-45min, the volume ratio of said mobile phase A and Mobile phase B is (90-95)/(5-10); At 46-55min, the volume ratio of said mobile phase A and Mobile phase B is (80-85)/(15-20); At 56-65min, the volume ratio of said mobile phase A and Mobile phase B is (68-72)/(28-32); At 66-75min, the volume ratio of said mobile phase A and Mobile phase B is (90-95)/(5-10); Reclaim the elutriant that contains rutin, Quercetin 3-galactoside, isoquercitrin, Quercetin respectively, obtain rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin after last underpressure distillation removes solvent.
2. method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin according to claim 1 is characterized in that: said phosphate buffered saline buffer is that the sodium hydroxide solution of phosphoric acid solution and the 8-12% of 0.15-0.25% is mixed to pH value 3.5-4.5 and is prepared from.
3. method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin according to claim 2; It is characterized in that: the compound method of said phosphate buffered saline buffer is: the sodium hydroxide solution of the phosphoric acid solution titration to 10% with 0.2%; Add air through stirring simultaneously in titration, be mixed to pH value 4.0 and be prepared from.
4. method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin according to claim 1 is characterized in that: the pH value of said phosphate buffered saline buffer is 4.0.
5. method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin according to claim 3 is characterized in that: at 0-45min, the volume ratio of said mobile phase A and Mobile phase B is 92/8.
6. method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin according to claim 3 is characterized in that: at 46-55min, the volume ratio of said mobile phase A and Mobile phase B is 82/18.
7. method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin according to claim 3 is characterized in that: at 56-65min, the volume ratio of said mobile phase A and Mobile phase B is 70/30.
8. method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin according to claim 3 is characterized in that: at 66-75min, the volume ratio of said mobile phase A and Mobile phase B is 92/8.
9. according to each described method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin of claim 5-8; It is characterized in that: said Lotus Leaf uses earlier dissolve with methanol solution and the ultrasonic 28-35min of massfraction as 75-85%; And then add the dissolve with methanol solution after-filtration of 75-85wt%, get the treat parting liquid of filtrating as said column chromatography.
10. method of from lotus leaf, separating rutin, Quercetin 3-galactoside, isoquercitrin and Quercetin according to claim 9; It is characterized in that: the first use of said Lotus Leaf massfraction is 80% dissolve with methanol solution and ultrasonic 30min; And then add the dissolve with methanol solution after-filtration of 80wt%, get the treat parting liquid of filtrating as said column chromatography.
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CN107522683A (en) * | 2017-07-17 | 2017-12-29 | 长沙爱扬医药科技有限公司 | A kind of method that OPC and Hyperoside are extracted from lotus pod |
CN110658295A (en) * | 2019-10-23 | 2020-01-07 | 葵花药业集团(襄阳)隆中有限公司 | Method for measuring fingerprint spectrum of lotus leaf decoction pieces in Erdong decoction formula |
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CN114235974A (en) * | 2021-11-05 | 2022-03-25 | 武汉人福创新药物研发中心有限公司 | Method for detecting rutin, isoquercitrin and rosmarinic acid content in herba Hedyotidis Diffusae or its extract |
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CN114235974B (en) * | 2021-11-05 | 2024-05-31 | 新疆维吾尔药业有限责任公司 | Method for detecting rutin, isoquercitrin and rosmarinic acid content in herba Hedyotidis Diffusae or extract thereof |
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CN114235974A (en) * | 2021-11-05 | 2022-03-25 | 武汉人福创新药物研发中心有限公司 | Method for detecting rutin, isoquercitrin and rosmarinic acid content in herba Hedyotidis Diffusae or its extract |
CN114235974B (en) * | 2021-11-05 | 2024-05-31 | 新疆维吾尔药业有限责任公司 | Method for detecting rutin, isoquercitrin and rosmarinic acid content in herba Hedyotidis Diffusae or extract thereof |
CN114441687A (en) * | 2022-02-17 | 2022-05-06 | 山东福瑞达生物股份有限公司 | Fingerprint spectrum construction method and application of antioxidant lotus leaf extract |
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