CN108484697A - The extraction of ursin and separation method in a kind of leaf of pear tree - Google Patents

The extraction of ursin and separation method in a kind of leaf of pear tree Download PDF

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Publication number
CN108484697A
CN108484697A CN201810569730.1A CN201810569730A CN108484697A CN 108484697 A CN108484697 A CN 108484697A CN 201810569730 A CN201810569730 A CN 201810569730A CN 108484697 A CN108484697 A CN 108484697A
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ursin
leaf
extraction
pear tree
ethanol water
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CN108484697B (en
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陈科猛
雷建都
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Anhui Long Run Tang Biotechnology Co Ltd
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Anhui Long Run Tang Biotechnology Co Ltd
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20Carbocyclic rings
    • C07H15/203Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00Processes for the preparation of sugar derivatives
    • C07H1/06Separation; Purification
    • C07H1/08Separation; Purification from natural products

Abstract

The invention belongs to the extracting methods of ursin, and in particular to the extraction of ursin and separation method in a kind of leaf of pear tree, including:(1) leaf of pear tree is collected, is crushed to after air-drying powdered;(2) it is added to after mixing powdered leaf of pear tree with ethanol water A in sub-critical extraction device, it is passed through nitrogen discharge oxygen, it is heated to 110~180 DEG C, control pressure is 0.5~5.0Mpa, extract 5~40min, feed liquid is taken out after cooling, supernatant is collected by centrifugation, and is concentrated by evaporation to obtain concentrate;(3) concentrate is pumped into the chromatographic column equipped with 8 fillers of metal-organic framework materials ZIF, is eluted using ethanol water B, eluent is concentrated by evaporation, is spray-dried to obtain ursin;Aqueous solution of the present invention to contain a small amount of ethyl alcohol realizes the high efficiency extraction of ursin using sub-critical extraction technology as solvent;The organic solvent that the technique consumes is few, and it is high to extract yield;The adsorbing separation of ursin is carried out using metal-organic framework materials ZIF 8, the step of separation is few, and the purity of obtained ursin is high.

Description

The extraction of ursin and separation method in a kind of leaf of pear tree
Technical field
The invention belongs to the extracting method technical fields of ursin, and in particular in a kind of leaf of pear tree the extraction of ursin with Separation method.
Background technology
Leaf of pear tree is the leaf of rose family Pyrus L pear tree, civil for treating snake bite, urethritis, cystitis, urine Cough, asthma etc. caused by road calculus and tracheitis.China's pear tree cultivated area is very big, and leaf of pear tree is as the pair in the production of fruit pears Product has a large amount of leaf of pear tree burned or is discarded every year, if can extract the active ingredient in leaf of pear tree, realizes The utilization of its high added value will turn waste into wealth, and more incomes are created for orchard worker.Contain ursin in leaf of pear tree, it is a kind of With anti-inflammatory, antibacterial, antibechic, eliminating the phlegm, antiasthmatic effect substance.Ursin can by inhibiting the activity of internal tyrosinase, The generation for preventing melanin, to reduce Skin pigmentation, dispelling stain and freckle, therefore, ursin is domestic and international at present Main active substances in skin-lightening cosmetic.
In the prior art, about the extraction of ursin in leaf of pear tree it has been reported that mainly using traditional organic molten Agent extracting method such as extracts ursin with ethyl alcohol multi-reflow, and this method extraction time is long, and ethyl alcohol recycling is difficult.In addition, black bearberry The method that the separation of glycosides mostly uses two steps or multistep macroporous resin adsorption or column chromatography, the inefficiency of separation, it tends to be difficult to full Foot requires.
Invention content
It is an object of the invention to overcome deficiency in the prior art, improve in a kind of leaf of pear tree the extraction of ursin with point From method, the added value of leaf of pear tree is improved, the high efficiency extraction of ursin is realized and detaches.
To achieve the goals above, the present invention is achieved by the following scheme:
The extraction of ursin and separation method, include the following steps in a kind of leaf of pear tree:
(1) leaf of pear tree is collected, is crushed to after air-drying powdered;
(2) by powdered leaf of pear tree and ethanol water A by weight 1:(5~30) subcritical carry is added to after mixing It taking in device, is passed through nitrogen discharge oxygen, is then heated to 110~180 DEG C, control pressure is 0.5~5.0Mpa, extraction 5~ 40min, it is then rapid cooling, feed liquid is taken out, supernatant is collected after centrifugation, supernatant is concentrated by evaporation to obtain concentrate;
(3) concentrate in step (2) is pumped into the chromatographic column equipped with metal-organic framework materials ZIF-8 fillers, is adopted It is eluted, the eluent being collected into is concentrated by evaporation, spray drying obtains black bearberry with the ethanol water B of 2~6 times of column volumes Glycosides;
The volume fraction of ethyl alcohol is 3~8% in the ethanol water A;The volume of ethyl alcohol point in the ethanol water B Number is 60~90%.
Preferably, in step (2), the mass ratio of powdered leaf of pear tree and ethanol water A are 1: 15.
Preferably, in step (2), Extracting temperature of the control leaf of pear tree in sub-critical extraction device be 140 DEG C, Pressure is 1.5Mpa, extraction time 10min.
Preferably, the volume fraction of ethyl alcohol is 5% in the ethanol water A;Second in the ethanol water B The volume fraction of alcohol is 75%.
Preferably, in step (3), the dosage of the ethanol water B is 3 times of column volumes.
In the present invention, the preparation method of the metal-organic framework materials ZIF-8 fillers is:5g 2-methylimidazoles is molten 2-methylimidazole solution, 2g Zn (NO are configured in 40mL methanol3)2·6H2O is dissolved in the mixed liquor of 40mL methanol and 20mL water In be configured to Zn (NO3)2·6H2O solution;Above-mentioned 2-methylimidazole solution is added to the Zn (NO3)2·6H2In O solution, It is stirred to react more than for 24 hours at a temperature of 20~60 DEG C, obtains white ZIF-8 dispersion liquids, collect to obtain nanometer through high speed centrifugation Grade ZIF-8 particles, then washs 3 times with methanol solution, then in vacuum degree are 0.45Mpa, and temperature is under 45 DEG C of vacuum condition Drying obtains solid powdery ZIF-8.
Compared with prior art, the present invention has the following technical effects:
1, in the present invention, the aqueous solution to contain a small amount of ethyl alcohol realizes pear tree as solvent using sub-critical extraction technology The high efficiency extraction of ursin in leaf;The organic solvent that the extraction process consumes is few, does not easily cause environmental pollution, and extract yield Height, extraction time are short;
2, in the present invention, the adsorbing separation of ursin is carried out using metal-organic framework materials ZIF-8, the step of separation Few, easy to operate, the purity of obtained ursin is high.
Description of the drawings
Fig. 1 is influence of the temperature to ursin recovery rate;
Fig. 2 is influence of the extraction time to ursin recovery rate;
Fig. 3 is influence of the liquid-solid ratio to ursin recovery rate;
Fig. 4 is the influence for extracting pressure to ursin recovery rate.
Specific implementation mode
In order to make the technical means, the creative features, the aims and the efficiencies achieved by the present invention be easy to understand, tie below Specific embodiment is closed, the present invention is furture elucidated.
In order to improve the added value of leaf of pear tree, avoid leaf of pear tree burned or the environmental pollution caused by discarded, the present invention The extraction of ursin and separation method in a kind of leaf of pear tree are provided, having evaded the when of extracting ursin in the prior art needs to use The drawbacks of a large amount of organic solvents, alleviates the pollution of environment, has saved the consumption of resource.
The extraction includes the following steps with separation method:
(1) leaf of pear tree is collected, is crushed to after air-drying powdered;
(2) by powdered leaf of pear tree and ethanol water A by weight 1:(5~30) subcritical carry is added to after mixing It taking in device, is passed through nitrogen discharge oxygen, is then heated to 110~180 DEG C, control pressure is 0.5~5.0Mpa, extraction 5~ 40min is then rapidly cooled to room temperature using cooling water, takes out feed liquid, supernatant is collected after centrifugation, supernatant is concentrated by evaporation Obtain concentrate;
(3) concentrate in step (2) is pumped into the chromatographic column equipped with metal-organic framework materials ZIF-8 fillers, is adopted It is eluted, the eluent being collected into is concentrated by evaporation, spray drying obtains black bearberry with the ethanol water B of 2~6 times of column volumes Glycosides;
The volume fraction of ethyl alcohol is 3~8% in the ethanol water A;The volume of ethyl alcohol point in the ethanol water B Number is 60~90%.
Leaf of pear tree of the present invention is the leaf of pear tree, and a large amount of pear tree can be obtained during producing fruit pears Leaf is collected, and impurities removing washes away foreign matter, dries;Meanwhile in order to ensure the efficiency of extraction, collection being obtained Leaf of pear tree carry out break process, so that it is adequately contacted with the organic solvent for extracting ursin.
In the present invention, using extractant of the water of a small amount of ethyl alcohol as leaf of pear tree powder is contained, in sub-critical extraction device In, ursin can quickly be precipitated, and be dissolved in the aqueous solution of ethyl alcohol, feed liquid is centrifuged further to filter Except the leaf of pear tree disintegrating slag in feed liquid, obtained supernatant is then evaporated concentration, to improve the concentration of ursin.
It is described using in the chromatographic column equipped with metal-organic framework materials ZIF-8 fillers in separation phase in the present invention ZIF-8 have abundant pore structure, the ursin of small molecule can be adsorbed, so that it is guaranteed that ursin effectively point From.
Further, according to the present invention, the mass ratio of powdered leaf of pear tree and ethanol water A should be controlled in suitable model In enclosing, if the ratio of powdered leaf of pear tree is excessive, i.e., solid phase is excessive during sub-critical extraction, then is difficult to realize adequately carry It takes, and the ratio of ethanol water A is excessive, then sexual valence is relatively low, causes the waste of ethanol water A and being stranded for later separation It is difficult.In the present invention, it is preferred that the mass ratio of the powdered leaf of pear tree and ethanol water A are 1:15.
In the present invention, the technological parameter of the sub-critical extraction device, i.e., when temperature, pressure in extraction process and extraction Between setting can select in a wider scope, in order to obtain best recovery rate, it is preferred that control leaf of pear tree subcritical Extracting temperature in extraction element is 140 DEG C, pressure 1.5Mpa, extraction time 10min.
Further, according to the present invention, the volume fraction of the ethyl alcohol in the ethanol water A can be in wider range Interior selection, in order to ensure best extraction efficiency, the volume fraction of ethyl alcohol is 5% in the ethanol water A.
Further, according to the present invention, the volume fraction of the ethyl alcohol in the ethanol water B can be in wider range Interior selection, in order to ensure best elution efficiency, the volume fraction of ethyl alcohol is 75% in the ethanol water B.
Further, the dosage of the ethanol water B is 3 times of column volumes.
Heretofore described column volume refers to after ZIF-8 fillers are packed into chromatographic column, from the bottom plate of column to ZIF-8 fillers The volume of deposition surface.
In the present invention, in order to reduce column pressure, the ZIF-8 is fitted into unsuitable excessively high, the height of the height in chromatographic column Degree is preferably 3~5cm.
In step (3) of the present invention, the spray drying specifically uses pressure spray dryer method, and pressure, which controls, is 100~250kg/cm2, at 130~180 DEG C, leaving air temp is controlled at 60~80 DEG C for inlet air temperature control.
The purpose of heretofore described evaporation and concentration is to reduce the volume of pending liquid, improves the efficiency of processing, described Be concentrated by evaporation use is art technology conventional technology, and this will not be repeated here by the present invention.
Below by way of specific embodiment to the excellent of the extraction of ursin in leaf of pear tree provided by the invention and separation method Point is described further.
Ursin in the present invention is carried out using high performance liquid chromatography, mass spectrum, infrared spectrum and nuclear magnetic resonance H spectrums and C spectrums Confirmation.
Embodiment 1
The extraction of ursin and separation method in a kind of leaf of pear tree:
(1) leaf of pear tree is collected, is crushed to after air-drying powdered;
(2) 10g leaf of pear tree powder is weighed, is added in the ethanol water A that 150g volume fractions are 5%, is then added sub- In critical extraction element, it is passed through nitrogen discharge oxygen, heating after extracting 10min, then uses cold at 140 DEG C, 1.5Mpa But water is rapidly cooled to room temperature, takes out feed liquid, supernatant is collected by centrifugation, evaporation and concentration obtains concentrate;
(3) concentrate in step (2) is pumped into the chromatographic column equipped with metal-organic framework materials ZIF-8 fillers, so It uses the volume fraction of 3 times of column volumes for 75% ethanol water B elutions afterwards, collects eluent, be evaporated concentration, spraying It is dry, the ursin after being detached.
The recovery rate of ursin is calculated, the recovery rate is the ratio that extraction gained ursin accounts for ursin total amount in raw material Example;The purity of isolated ursin is tested, and above-mentioned test result is recorded in table 1.
The assay method of ursin total amount is in raw material, using the leaf of pear tree of same batch as raw material, using methanol as solvent, Refluxing extraction 3h repeats extraction 3 times to leaf of pear tree, merges extracting solution, measures the content of wherein ursin, raw material is calculated with this The total amount of middle ursin.
Embodiment 2
The extraction of ursin and separation method in a kind of leaf of pear tree:
(1) leaf of pear tree is collected, is crushed to after air-drying powdered;
(2) 15g leaf of pear tree powder is weighed, is added in the ethanol water A that 450g volume fractions are 8%, is then added sub- In critical extraction element, it is passed through nitrogen discharge oxygen, heating, at 180 DEG C, 5Mpa, after extracting 40min, then using cooling Water is rapidly cooled to room temperature, takes out feed liquid, supernatant is collected by centrifugation, evaporation and concentration obtains concentrate;
(3) concentrate in step (2) is pumped into the chromatographic column equipped with metal-organic framework materials ZIF-8 fillers, so It uses the volume fraction of 6 times of column volumes for 90% ethanol water B elutions afterwards, collects eluent, be evaporated concentration, spraying It is dry, the ursin after being detached.
The purity of the ursin obtained after the recovery rate of calculating ursin and separation, and test result is recorded in table 1.
Embodiment 3
The extraction of ursin and separation method in a kind of leaf of pear tree:
(1) leaf of pear tree is collected, is crushed to after air-drying powdered;
(2) 20g leaf of pear tree powder is weighed, is added in the ethanol water A that 100g volume fractions are 3%, is then added sub- In critical extraction element, it is passed through nitrogen discharge oxygen, heating, at 110 DEG C, 0.5Mpa, after extracting 5min, then using cooling Water is rapidly cooled to room temperature, takes out feed liquid, supernatant is collected by centrifugation, evaporation and concentration obtains concentrate;
(3) concentrate in step (2) is pumped into the chromatographic column equipped with metal-organic framework materials ZIF-8 fillers, so It uses the volume fraction of 5 times of column volumes for 60% ethanol water B elutions afterwards, collects eluent, be evaporated concentration, spraying It is dry, the ursin after being detached.
The purity of the ursin obtained after the recovery rate of calculating ursin and separation, and test result is recorded in table 1.
Embodiment 4
The extraction of ursin and separation method in a kind of leaf of pear tree:
(1) leaf of pear tree is collected, is crushed to after air-drying powdered;
(2) 40g leaf of pear tree powder is weighed, is added in the ethanol water A that 800g volume fractions are 7%, is then added sub- In critical extraction element, it is passed through nitrogen discharge oxygen, heating after extracting 20min, then uses cold at 130 DEG C, 1.5Mpa But water is rapidly cooled to room temperature, takes out feed liquid, supernatant is collected by centrifugation, evaporation and concentration obtains concentrate;
(3) concentrate in step (2) is pumped into the chromatographic column equipped with metal-organic framework materials ZIF-8 fillers, so It uses the volume fraction of 4 times of column volumes for 70% ethanol water B elutions afterwards, collects eluent, be evaporated concentration, spraying It is dry, the ursin after being detached.
The purity of the ursin obtained after the recovery rate of calculating ursin and separation, and test result is recorded in table 1.
Embodiment 5
The extraction of ursin and separation method in a kind of leaf of pear tree:
(1) leaf of pear tree is collected, is crushed to after air-drying powdered;
(2) 25g leaf of pear tree powder is weighed, is added in the ethanol water A that 625g volume fractions are 4%, is then added sub- In critical extraction element, it is passed through nitrogen discharge oxygen, heating after extracting 25min, then uses cold at 150 DEG C, 1.2Mpa But water is rapidly cooled to room temperature, takes out feed liquid, supernatant is collected by centrifugation, evaporation and concentration obtains concentrate;
(3) concentrate in step (2) is pumped into the chromatographic column equipped with metal-organic framework materials ZIF-8 fillers, so It uses the volume fraction of 3.5 times of column volumes for 80% ethanol water B elutions afterwards, collects eluent, be evaporated concentration, spray Mist is dried, the ursin after being detached.
The purity of the ursin obtained after the recovery rate of calculating ursin and separation, and test result is recorded in table 1.
Embodiment 6
The extraction of ursin and separation method in a kind of leaf of pear tree:
(1) leaf of pear tree is collected, is crushed to after air-drying powdered;
(2) 50g leaf of pear tree powder is weighed, is added in the ethanol water A that 500g volume fractions are 5%, is then added sub- In critical extraction element, it is passed through nitrogen discharge oxygen, heating after extracting 12min, then uses cold at 160 DEG C, 3.5Mpa But water is rapidly cooled to room temperature, takes out feed liquid, supernatant is collected by centrifugation, evaporation and concentration obtains concentrate;
(3) concentrate in step (2) is pumped into the chromatographic column equipped with metal-organic framework materials ZIF-8 fillers, so It uses the volume fraction of 2.5 times of column volumes for 85% ethanol water B elutions afterwards, collects eluent, be evaporated concentration, spray Mist is dried, the ursin after being detached.
The purity of the ursin obtained after the recovery rate of calculating ursin and separation, and test result is recorded in table 1.
Table 1:
The extraction of ursin and separation method in leaf of pear tree provided by the invention, using 5% ethanol water as Extraction solvent, It is 15 in liquid-solid ratio:1,140 DEG C of temperature, pressure 1.5Mpa, extraction time 10min extraction conditions under obtained ursin carry Take rate highest, the purity highest of the ursin of acquisition.
Further to study the extraction of ursin and separation method in leaf of pear tree provided by the invention, the present invention passes through experiment To the extraction conditions of ursin in leaf of pear tree, includes the optimization of extraction time, Extracting temperature, extraction pressure and liquid-solid ratio, obtain To the extraction conditions of optimization, preferable yield is obtained.
Extracting temperature is studied in leaf of pear tree when the influence of ursin recovery rate, fixed extraction pressure, time and liquid-solid ratio, Transformation temperature extracts experiment, obtains preferable Extracting temperature;Then, under preferable Extracting temperature, fixed extraction pressure and liquid Gu ratio, transformation period extract experiment, obtain preferable extraction time;It is fixed in the preferable Extracting temperature of gained, under the time Pressure changes liquid-solid ratio, extracts experiment, obtain preferable liquid-solid ratio;It is finally solid in the preferred temperature of acquisition, time, liquid Than under the conditions of, change pressure extracts experiment, obtains preferably extracting pressure, can be obtained preferable extraction conditions in this way.Specifically Experimental result it is as shown in Figs 1-4.
The basic principles and main features and the features of the present invention of the present invention have been shown and described above.The technology of the industry Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this The principle of invention, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these changes Change and improvement is both fallen in the range of claimed invention.The scope of protection of present invention is by appended claims And its equivalent thereof.

Claims (5)

1. the extraction of ursin and separation method in a kind of leaf of pear tree, it is characterised in that:Include the following steps:
(1) leaf of pear tree is collected, is crushed to after air-drying powdered;
(2) by powdered leaf of pear tree and ethanol water A by weight 1:(5~30) sub-critical extraction dress is added to after mixing In setting, it being passed through nitrogen discharge oxygen, is then heated to 110~180 DEG C, control pressure is 0.5~5.0Mpa, extraction 5~ 40min, it is then rapid cooling, feed liquid is taken out, supernatant is collected after centrifugation, supernatant is concentrated by evaporation to obtain concentrate;
(3) concentrate in step (2) is pumped into the chromatographic column equipped with metal-organic framework materials ZIF-8 fillers, using 2~ The ethanol water B of 6 times of column volumes is eluted, and the eluent being collected into is concentrated by evaporation, spray drying obtains ursin;
The volume fraction of ethyl alcohol is 3~8% in the ethanol water A;The volume fraction of ethyl alcohol is in the ethanol water B 60~90%.
2. the extraction of ursin and separation method in leaf of pear tree according to claim 1, it is characterised in that:In step (2), The mass ratio of powdered leaf of pear tree and ethanol water A are 1:15.
3. the extraction of ursin and separation method in leaf of pear tree according to claim 1, it is characterised in that:In step (2), Control Extracting temperature of the leaf of pear tree in sub-critical extraction device be 140 DEG C, pressure 1.5Mpa, extraction time 10min.
4. the extraction of ursin and separation method in leaf of pear tree according to claim 1, it is characterised in that:The ethanol water The volume fraction of ethyl alcohol is 5% in solution A;The volume fraction of ethyl alcohol is 75% in the ethanol water B.
5. the extraction of ursin and separation method in leaf of pear tree according to claim 1, it is characterised in that:In step (3), The dosage of the ethanol water B is 3 times of column volumes.
CN201810569730.1A 2018-06-05 2018-06-05 Extraction and separation method of arbutin in pear leaves Active CN108484697B (en)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01269498A (en) * 1988-04-22 1989-10-26 Shiseido Co Ltd Production of arbutin
KR20110033535A (en) * 2009-09-25 2011-03-31 전남대학교산학협력단 Isolation method of arbutin in high purity from extract of pear peel and arbutin isolated thereby
CN103989590A (en) * 2014-04-30 2014-08-20 吴雪琴 Arbutin herbal essence preparation method and product thereof
CN107098942A (en) * 2017-05-02 2017-08-29 江苏大学 A kind of method of kaempferia galamga glycosides in Subcritical Water Extraction radish leaves

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH01269498A (en) * 1988-04-22 1989-10-26 Shiseido Co Ltd Production of arbutin
KR20110033535A (en) * 2009-09-25 2011-03-31 전남대학교산학협력단 Isolation method of arbutin in high purity from extract of pear peel and arbutin isolated thereby
CN103989590A (en) * 2014-04-30 2014-08-20 吴雪琴 Arbutin herbal essence preparation method and product thereof
CN107098942A (en) * 2017-05-02 2017-08-29 江苏大学 A kind of method of kaempferia galamga glycosides in Subcritical Water Extraction radish leaves

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