CN107619422A - A kind of method for preparing the O glucuronides of high-purity gossypitrin 8 - Google Patents
A kind of method for preparing the O glucuronides of high-purity gossypitrin 8 Download PDFInfo
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- CN107619422A CN107619422A CN201711024508.5A CN201711024508A CN107619422A CN 107619422 A CN107619422 A CN 107619422A CN 201711024508 A CN201711024508 A CN 201711024508A CN 107619422 A CN107619422 A CN 107619422A
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Abstract
The present invention relates to one kind from Golden flower extract solution, using metal zinc ion and Flavonoid substances complex scheme, the method for obtaining the O glucuronides of high-purity gossypitrin 8.Belong to metal complex preparation, native compound extraction and separation field.Method is as follows:Microwave radiation technology alcohol water extracts Golden flower;In the basic conditions, the O glucuronides of gossypitrin 8 in Golden flower are made to form stable comple with zinc salt;Add and be complexed stronger ethylenediamine tetra-acetic acid (EDTA) with zinc salt, it is complexed the O glucuronide complex compounds solution of zinc salt gossypitrin 8, the high O glucuronides of free state gossypitrin 8 of purity are converted into, increase substantially the concentration of the O glucuronides of gossypitrin 8 in solution.This method can quickly, safely, effectively isolate and purify the O glucuronides of gossypitrin 8 from Golden flower, help to realize the industrial production of the O glucuronides of gossypitrin 8.
Description
Technical field
The present invention relates to one kind from Golden flower extract solution, using metal zinc ion and Flavonoid substances complex scheme,
The method for obtaining high-purity gossypitrin -8-O- glucuronides.Belong to metal complex preparation, native compound extraction and
Separation field.
Background technology
Golden flower (Hibiscus Manihot L.) alias vegetable Furong, wild lotus, glutinous dry or wych-elm skin, are annual grass
This Malvaceae (Malvaceae) gumbo platymiscium, it is a kind of wild rare flowers in imminent danger being grown between the gap of remote mountains precipice.Golden flower
First recorded in Ming Dynasty constitution ancestor between change year《Shuande mansion will》, but because modern domestic documents and materials have no way of searching, until 2003
Xingtai area is again found to, its most edible, medicinal, nutrition and beauty treatment weight reducing etc. in individual abelmoschus plant more than 200
Healthcare function (Chinese drug evaluation, 2015,32,90-92).Existing patent report Golden flower can be further processed into high-class healthy
Product, cosmetics and medicine.At present in each version《Pharmacopoeia of People's Republic of China》And have no and record in Ministry of Public Health's medicine ministry standard,
But some pharmacological researches prove that it has good antalgic and inflammation relieving, anti-oxidant, reducing blood lipid, immunological regulation, suppression tumour cell etc.
Act on (fine chemistry industry, 2016,33,890-895.), there is higher medical value and vast potential for future development.
Golden flower has the good reputation of " plant giant panda ", containing various plants bioactive substance, mainly there is flavonoid
Thing, vitamin E, unrighted acid, dietary fiber and trace element etc..These nutriments are needed by human but can not
Voluntarily synthesize, it is necessary to taken in by diet, in recent years, flower of JINHUAKUI is closed as the important sources of extraction Flavonoid substances by each side
Note.Research shows that gossypitrin -8-O- glucuronides are content highest flavone compound in flower of JINHUAKUI, are golden flower
One of main active of sunflower (Journal of chromatographic science, 2009,47,206-210),
It has good anti-inflammatory activity and neurocyte protection as a kind of flavonoid drugs typically containing 6 hydroxyls
Effect (Computational biology and chemistry, 2016,64,353-358).Clinic can be used for as one kind
The diseases such as anti-senile dementia, tumor disease and angiocarpy potential drug (Neuroscience letters 2009,461,
172–176).Gossypitrin -8-O- glucuronides structural formula is as shown in following formula I:
The isolation and purification method of flavones mainly has solvent extraction, membrane separation process, Amberlyst process, column chromatography etc. at present
Method (Chinese measuring technology, 2007,33,22-25), but these methods are present that purification process is cumbersome, cost is too high, production is all
Phase is long, is difficult to the problems such as industrial production, limits the application of Golden flower flavones.We can with metal salt using flavone compound
Form the characteristic of stable comple, develop it is a kind of it is quick, safe, feasible, efficiently separate purifying gossypitrin -8-O- glucose
The method of aldehydic acid glycosides.Such complex compound is advantageous to human body to transporting and absorbing inside respective metal salt, it is also possible to help
Flavone compound is taken in, is a kind of medicine with huge potentiality to be exploited, is worth further it is carefully studied and opened
Hair utilizes.Therefore, the extraction raw material by the use of Golden flower as gossypitrin -8-O- glucuronides, directly enhances Golden flower
Comprehensive utilization value and economic benefit so that Golden flower in the industries such as medicine, food or health products have preferably application
Prospect.At present from Golden flower prepare high-purity gossypitrin -8-O- glucuronides there is not been reported.
The present invention forms stable comple from Golden flower extract solution using flavone compound in Golden flower and zinc salt
Characteristic, gossypitrin -8-O- glucuronides are separated from Golden flower extract solution.Complex compound sediment is separated
Afterwards, the stronger complexing agent EDTA of effect is complexed than flavone compound by adding, the flavones of complex state is converted into purity height
Free state flavones, obtain the gossypitrin -8-O- glucuronides of high-purity.
The content of the invention
The purpose of the present invention is can to form the characteristic of stable comple, exploitation one with metal zinc salt using flavone compound
Quick, safe, the feasible method that purifying gossypitrin -8-O- glucuronides are efficiently separated from Golden flower of kind.
The purpose of the present invention is realized by following technical scheme:
It is a kind of from Golden flower extract solution, using zinc salt and Flavonoid substances complex scheme, acquisition high-purity gossypitrin-
The method of 8-O- glucuronides, its step are as follows:
A. precision weighs 5.0g and dries flower of JINHUAKUI corase meal, is 400W in power, and under conditions of 80 DEG C of temperature, microwave carries
15min is taken, is filtered after being cooled to room temperature, obtains Golden flower residue and supernatant, supernatant is collected, is determined with 70% ethanol solution
Hold in 250mL volumetric flasks and produce sample solution;
B. Golden flower sample solution is weighed, it is 8.5-11.5 to adjust pH value with alkaline solution, and alkaline solution used may be selected
Finite concentration sodium hydroxide solution, potassium hydroxide solution, sodium carbonate liquor, ammoniacal liquor etc..Certain mass concentration zinc salt is added, it is used
Zinc sulfate, zinc acetate, zinc chloride etc. may be selected in zinc salt, and addition ensures that the mass ratio of Golden flower sample and zinc salt is 1/0.5-1/
5.After addition, the complex reaction time is 1-12h.Complex reaction temperature is 10-70 DEG C, centrifuges the heavy of complex reaction generation
Form sediment;
C. the ethanol of the dissociation agent ethylenediamine tetra-acetic acid (EDTA) and 10%-70% of certain mass is added in above-mentioned precipitation
Solution carries out solution complex reaction, preferably 50% ethanol solution, and addition ensures that zinc salt and EDTA mass ratio are 1/1-1/
5, preferably 1/1.After addition, ultrasonic 0.5-4h, preferably 0.5h.The precipitation generated after solution complex reaction is centrifuged, is collected
Supernatant, concentration, obtains high-purity gossypitrin -8-O- glucuronides.
High-purity gossypitrin -8-O- the glucuronides of extract solution and preparation to Golden flower are through high performance liquid chromatography point
Analysis obtains analysis result, and chromatogram is shown in accompanying drawing.The chromatographic condition used for:Waters HPLC high performance liquid chromatographs, chromatographic column
For COSMOSIL C18 (4.6mm × 200mm, 5 μm), mobile phase be the formic acid solution of acetonitrile -0.1% gradient elution (0min, 15:
85v/v;18min, 16:84v/v;26min, 20:80v/v;35min, 40:60v/v;40min, 40:60v/v), flow velocity is
1.0m L/min, Detection wavelength 360nm, the μ L of sample size 10, column temperature is room temperature.
The present invention achieves following useful achievement:
1st, Golden flower extract solution need not be further processed, is directly added into zinc solution, make zinc salt by adjusting pH
Be complexed with gossypitrin -8-O- glucuronides in extract solution, simplify processing step, save the operating time, reduce manpower and
Consumption of the energy etc., improves preparation efficiency and economic benefit;
2nd, the cost using zinc salts such as zinc sulfate is low, nontoxic, and degree of danger reduces, and also allows for returning for Extraction solvent
Receive;
3rd, the stronger complexing agent EDTA of effect is complexed than flavone compound by adding, the flavones of complex state is converted into
The high free state flavones of purity, increase substantially the concentration of gossypitrin -8-O- glucuronides in organic solution.By foregoing
Combination operation, it is easy to purify the large-scale industrial production of gossypitrin -8-O- glucuronides.
Brief description of the drawings
Fig. 1 is the HPLC spectrograms of gossypitrin -8-O- glucuronides in not purified Golden flower extract solution.
Fig. 2 is the HPLC spectrograms of gossypitrin -8-O- glucuronides in the sample for handle purifying by complex compound.
Embodiment:
Flavonoid substances are extracted from Golden flower to one kind of the present invention with specific embodiment below in conjunction with the accompanying drawings, prepared
The method of high-purity gossypitrin -8-O- glucuronides further illustrates, so that those skilled in the art becomes more apparent upon this
Invention, but the present invention is not limited with this.
Embodiment 1:
A. precision weighs 5.0g and dries flower of JINHUAKUI corase meal, is 400W in power, and under conditions of 80 DEG C of temperature, microwave carries
15min is taken, is filtered after being cooled to room temperature, obtains Golden flower residue and supernatant, supernatant is collected, is determined with 70% ethanol solution
Hold in 250mL volumetric flasks and produce sample solution;
B. 10mL Golden flower sample solutions are measured, is 9.5 with sodium hydroxide solution regulation pH value, adds certain mass concentration
Zinc sulfate, addition ensure that the mass ratio of Golden flower sample and zinc sulfate is 1/0.5.After addition, the complex reaction time is 3h, network
It is 30 DEG C to close reaction temperature, and precipitation is generated after centrifuging complex reaction;
C. the dissociation agent ethylenediamine tetra-acetic acid (EDTA) and 50% ethanol solution of certain mass are added in above-mentioned precipitation
Solution complex reaction is carried out, addition ensures that zinc sulfate and EDTA mass ratio are 1/1.After addition, ultrasonic 0.5h, solution is centrifuged
The precipitation generated after complex reaction, supernatant is collected, concentration, obtains high-purity gossypitrin -8-O- glucuronides, purity reaches
82.16%.
Embodiment 2:
A. precision weighs 5.0g and dries flower of JINHUAKUI corase meal, is 400W in power, and under conditions of 80 DEG C of temperature, microwave carries
15min is taken, is filtered after being cooled to room temperature, obtains Golden flower residue and supernatant, supernatant is collected, is determined with 70% ethanol solution
Hold in 250mL volumetric flasks and produce sample solution;
B. 10mL Golden flower sample solutions are measured, is 11.5 with sodium carbonate liquor regulation pH value, adds certain mass concentration
Zinc chloride, addition ensure that the mass ratio of Golden flower sample and zinc chloride is 1/0.5.After addition, the complex reaction time is 12h.
Complex reaction temperature is 70 DEG C, and precipitation is generated after centrifuging complex reaction;
C. the dissociation agent ethylenediamine tetra-acetic acid (EDTA) and 30% ethanol solution of certain mass are added in above-mentioned precipitation
Solution complex reaction is carried out, addition ensures that zinc chloride and EDTA mass ratio are 1/5.After addition, ultrasonic 4h, decomplexing is centrifuged
The precipitation generated after reaction is closed, supernatant is collected, concentration, obtains high-purity gossypitrin -8-O- glucuronides, purity reaches
73.79%.
Embodiment 3:
A. precision weighs 5.0g and dries flower of JINHUAKUI corase meal, is 400W in power, and under conditions of 80 DEG C of temperature, microwave carries
15min is taken, is filtered after being cooled to room temperature, obtains Golden flower residue and supernatant, supernatant is collected, is determined with 70% ethanol solution
Hold in 250mL volumetric flasks and produce sample solution;
B. 10mL Golden flower sample solutions are measured, is 11.5 with potassium hydroxide solution regulation pH value, it is dense to add certain mass
Zinc acetate is spent, addition ensures that the mass ratio of Golden flower sample and zinc acetate is 1/5.After addition, the complex reaction time is 1h.Network
It is 10 DEG C to close reaction temperature, and precipitation is generated after centrifuging complex reaction;
C. the dissociation agent ethylenediamine tetra-acetic acid (EDTA) and 10% ethanol solution of certain mass are added in above-mentioned precipitation
Solution complex reaction is carried out, addition ensures that zinc acetate and EDTA mass ratio are 1/5.After addition, ultrasonic 1h, decomplexing is centrifuged
The precipitation generated after reaction is closed, supernatant is collected, concentration, obtains high-purity gossypitrin -8-O- glucuronides, purity reaches
71.43%.
Embodiment 4:
A. precision weighs 5.0g and dries flower of JINHUAKUI corase meal, is 400W in power, and under conditions of 80 DEG C of temperature, microwave carries
15min is taken, is filtered after being cooled to room temperature, obtains Golden flower residue and supernatant, supernatant is collected, is determined with 70% ethanol solution
Hold in 250mL volumetric flasks and produce sample solution;
B. 10mL Golden flower sample solutions are measured, is 9.5 with ammoniacal liquor regulation pH value, adds certain mass concentration sulphuric acid zinc,
Addition ensures that the mass ratio of Golden flower sample and zinc sulfate is 1/0.5.After addition, the complex reaction time is 5h.Complex reaction
Temperature is 50 DEG C, and precipitation is generated after centrifuging complex reaction;
C. the dissociation agent ethylenediamine tetra-acetic acid (EDTA) and 70% ethanol solution of certain mass are added in above-mentioned precipitation
Solution complex reaction is carried out, addition ensures that zinc sulfate and EDTA mass ratio are 1/1.After addition, ultrasonic 4h, decomplexing is centrifuged
The precipitation generated after reaction is closed, supernatant is collected, concentration, obtains high-purity gossypitrin -8-O- glucuronides, purity reaches
75.72%.
Embodiment 5:
A. precision weighs 5.0g and dries flower of JINHUAKUI corase meal, is 400W in power, and under conditions of 80 DEG C of temperature, microwave carries
15min is taken, is filtered after being cooled to room temperature, obtains Golden flower residue and supernatant, supernatant is collected, is determined with 70% ethanol solution
Hold in 250mL volumetric flasks and produce sample solution;
B. 10mL Golden flower sample solutions are measured, is 10.5 with sodium hydroxide regulation pH value, adds certain mass concentration sulphur
Sour zinc, addition ensure that the mass ratio of Golden flower sample and zinc sulfate is 1/1.After addition, the complex reaction time is 5h.Complexing is anti-
It is 50 DEG C to answer temperature, and precipitation is generated after centrifuging complex reaction;
C. the dissociation agent ethylenediamine tetra-acetic acid (EDTA) and 50% ethanol solution of certain mass are added in above-mentioned precipitation
Solution complex reaction is carried out, addition ensures that zinc sulfate and EDTA mass ratio are 1/1.After addition, ultrasonic 1h, decomplexing is centrifuged
The precipitation generated after reaction is closed, supernatant is collected, concentration, obtains high-purity gossypitrin -8-O- glucuronides, purity reaches
77.54%.
Embodiment 6:
A. precision weighs 5.0g and dries flower of JINHUAKUI corase meal, is 400W in power, and under conditions of 80 DEG C of temperature, microwave carries
15min is taken, is filtered after being cooled to room temperature, obtains Golden flower residue and supernatant, supernatant is collected, is determined with 70% ethanol solution
Hold in 250mL volumetric flasks and produce sample solution;
B. 10mL Golden flower sample solutions are measured, is 8.5 with sodium hydroxide regulation pH value, adds certain mass concentration sulphuric acid
Zinc, addition ensure that the mass ratio of Golden flower sample and zinc sulfate is 1/2.After addition, the complex reaction time is 7h.Complex reaction
Temperature is 50 DEG C, and precipitation is generated after centrifuging complex reaction;
C. the dissociation agent ethylenediamine tetra-acetic acid (EDTA) and 50% ethanol solution of certain mass are added in above-mentioned precipitation
Solution complex reaction is carried out, addition ensures that zinc sulfate and EDTA mass ratio are 1/2.After addition, ultrasonic 1h, decomplexing is centrifuged
The precipitation generated after reaction is closed, supernatant is collected, concentration, obtains high-purity gossypitrin -8-O- glucuronides, purity reaches
65.49%.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and
Within principle, any modification, equivalent substitution and improvements made etc., it should be included in the scope of the protection.
Claims (9)
- A kind of 1. method for preparing high-purity gossypitrin -8-O- glucuronides, it is characterised in that:A. precision weighs 5.0g and dries flower of JINHUAKUI corase meal, is 400W in power, under conditions of 80 DEG C of temperature, Microwave Extraction 15min, filtered after being cooled to room temperature, obtain Golden flower residue and supernatant, supernatant is collected, with 70% ethanol solution constant volume Sample solution is produced into 250mL volumetric flasks;B. Golden flower sample solution is weighed, it is 8.5-11.5 to adjust pH value with alkaline solution, and alkaline solution used may be selected certain Sodium hydroxide solution, potassium hydroxide solution, sodium carbonate liquor, ammoniacal liquor etc.;Add finite concentration zinc solution, zinc salt used Zinc sulfate, zinc acetate, zinc chloride etc. may be selected, addition ensures that the mass ratio of Golden flower sample and zinc salt is 1/0.5-1/5.Add After adding, the complex reaction time is 1-12h;Complex reaction temperature is 10-70 DEG C, centrifuges the precipitation of complex reaction generation;C. the dissociation agent ethylenediamine tetra-acetic acid (EDTA) of addition certain mass and 10%-70% ethanol are molten in above-mentioned precipitation Liquid carries out solution complex reaction, and addition ensures that zinc salt and EDTA mass ratio are 1/1-1/5.After addition, ultrasonic 0.5-4h;Centrifugation The precipitation generated after separation solution complex reaction, collects supernatant, concentration, obtains high-purity gossypitrin -8-O- glucuronides.
- 2. a kind of method for preparing high-purity gossypitrin -8-O- glucuronides according to claim 1, its feature exist In:Finite concentration sodium hydroxide solution, potassium hydroxide solution, sodium carbonate liquor, ammoniacal liquor etc., preferably hydrogen may be selected in alkaline solution Sodium hydroxide solution;Regulation pH value is 8.5-11.5, preferably 9.5.
- 3. a kind of method for preparing high-purity gossypitrin -8-O- glucuronides according to claim 1, its feature exist In:Zinc sulfate, zinc acetate, zinc chloride etc., preferably zinc sulfate may be selected in zinc salt used in complex reaction.
- 4. a kind of method for preparing high-purity gossypitrin -8-O- glucuronides according to claim 1, its feature exist In:The mass ratio of Golden flower sample and zinc salt is 1/0.5-1/5 in complex reaction, preferably 1/1.
- 5. a kind of method for preparing high-purity gossypitrin -8-O- glucuronides according to claim 1, its feature exist In:The complex reaction time is 1-12h, preferably 3h.
- 6. a kind of method for preparing high-purity gossypitrin -8-O- glucuronides according to claim 1, its feature exist In:Complex reaction temperature is 10-70 DEG C, preferably 30 DEG C.
- 7. a kind of method for preparing high-purity gossypitrin -8-O- glucuronides according to claim 1, its feature exist In:Solve the ethanol solution that solvent used in complex reaction is 10%-70%, preferably 50% ethanol solution.
- 8. a kind of method for preparing high-purity gossypitrin -8-O- glucuronides according to claim 1, its feature exist In:Zinc salt and EDTA mass ratio are 1/1-1/5 in solution complex reaction, preferably 1/1.
- 9. a kind of method for preparing high-purity gossypitrin -8-O- glucuronides according to claim 1, its feature exist In:Solve ultrasonic 0.5-4h, preferably 0.5h in complex reaction.
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CN111437311A (en) * | 2020-01-17 | 2020-07-24 | 杭州师范大学 | Method for extracting flavonoids from pharbitis seed peels |
CN111437311B (en) * | 2020-01-17 | 2022-03-22 | 杭州师范大学 | Method for extracting flavonoids from pharbitis seed peels |
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