CN102453735A - Method for obtaining icaritin from icariin by adopting naringinase - Google Patents
Method for obtaining icaritin from icariin by adopting naringinase Download PDFInfo
- Publication number
- CN102453735A CN102453735A CN2010105177936A CN201010517793A CN102453735A CN 102453735 A CN102453735 A CN 102453735A CN 2010105177936 A CN2010105177936 A CN 2010105177936A CN 201010517793 A CN201010517793 A CN 201010517793A CN 102453735 A CN102453735 A CN 102453735A
- Authority
- CN
- China
- Prior art keywords
- icarin
- reaction
- icariin
- naringinase
- epimedium aglucone
- 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
- TZJALUIVHRYQQB-UHFFFAOYSA-N icariine Natural products C1=CC(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(C)O2)O)C(=O)C2=C(O)C=C(OC3C(C(O)C(O)C(CO)O3)O)C(CC=C(C)C)=C2O1 TZJALUIVHRYQQB-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title claims abstract description 17
- 108010001078 naringinase Proteins 0.000 title claims abstract description 15
- TZJALUIVHRYQQB-XFDQAQKOSA-N Icariin Natural products O(C)c1ccc(C2=C(O[C@H]3[C@@H](O)[C@H](O)[C@@H](O)[C@H](C)O3)C(=O)c3c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O4)c(C/C=C(\C)/C)c3O2)cc1 TZJALUIVHRYQQB-XFDQAQKOSA-N 0.000 title abstract 6
- TZJALUIVHRYQQB-XLRXWWTNSA-N icariin Chemical compound C1=CC(OC)=CC=C1C1=C(O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)C(=O)C2=C(O)C=C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)C(CC=C(C)C)=C2O1 TZJALUIVHRYQQB-XLRXWWTNSA-N 0.000 title abstract 6
- TUUXBSASAQJECY-UHFFFAOYSA-N 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)chromen-4-one Chemical compound C1=CC(OC)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C(CC=C(C)C)=C2O1 TUUXBSASAQJECY-UHFFFAOYSA-N 0.000 title abstract 4
- CTGVBHDTGZUEJZ-UHFFFAOYSA-N Noricaritin Natural products CC(C)(O)CCC1=C(O)C=C(O)C(C(C=2O)=O)=C1OC=2C1=CC=C(O)C=C1 CTGVBHDTGZUEJZ-UHFFFAOYSA-N 0.000 title abstract 2
- 230000035484 reaction time Effects 0.000 claims abstract 2
- 241000893536 Epimedium Species 0.000 claims description 32
- 235000018905 epimedium Nutrition 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 108010047754 beta-Glucosidase Proteins 0.000 claims description 2
- 102000006995 beta-Glucosidase Human genes 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 23
- 238000006911 enzymatic reaction Methods 0.000 abstract description 7
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 abstract description 6
- 230000009471 action Effects 0.000 abstract description 2
- 125000003147 glycosyl group Chemical group 0.000 abstract description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 230000007246 mechanism Effects 0.000 description 6
- 238000004451 qualitative analysis Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RHQQHZQUAMFINJ-GKWSUJDHSA-N 1-[(3s,5s,8s,9s,10s,11s,13s,14s,17s)-3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CC[C@H]21 RHQQHZQUAMFINJ-GKWSUJDHSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001720 carbohydrates Chemical class 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000003810 ethyl acetate extraction Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- -1 cyclic monophosphate Chemical class 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 108010006464 Hemolysin Proteins Proteins 0.000 description 1
- 108010017842 Telomerase Proteins 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 210000000750 endocrine system Anatomy 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000001456 gonadotroph Effects 0.000 description 1
- 239000003228 hemolysin Substances 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000036581 peripheral resistance Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000013404 process transfer Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
Images
Landscapes
- Enzymes And Modification Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
A method for converting icariin into icaritin by biological enzyme reaction to improve its bioactivity is provided. Under the action of naringinase, the reaction is carried out in 30 to 70 percent ethanol water solution. The reaction temperature is 40-70 ℃, and the reaction time is 1-30 hours. The glycosyl on the hydroxyl of icariin is cut off and converted into icariin aglycon with higher pharmacological activity. The invention also improves the processability of icariin and can expand the practical application range of icariin.
Description
Technical field
The present invention relates to utilize icarin to transfer a kind of method of epimedium aglucone to, relate in particular to and utilize the naringinase reaction to obtain the method for epimedium aglucone.
Background technology
Icarin (Icratin) molecular formula is C
33H
40O
15, chemical structural formula is suc as formula shown in the I.Faint yellow needle crystal.
(formula I)
Icarin derives from natural product.Natural active matter icarin and epimedium aglucone have very great development and are worth.Icarin and epimedium aglucone purposes are the treatment of clinical cardiovascular disorder more at present.
The icarin tool obviously suppresses myocardial contraction, reduces the climbing speed of left ventricular pressure, shows that it can reduce MCO, reduces Peripheral resistance simultaneously, alleviates cardiac afterload, and cardiovascular disordeies such as myocardial ischemia and irregular pulse are had the improvement effect.
Icarin has obvious effect to endocrine system.Can obviously promote also has promoter action in the generation of basal secretion and cyclic monophosphate of testosterone, shows as gonadotropic Effect.
Icarin can promote the lymphopoiesis of antigen activates, improves serum hemolysin antibody and generates level.Can obviously suppress telomerase activation, the leukemia cell is all had the differentiation of more significantly inducing and suppresses proliferation function.
But in medical practice, the molecular structure of natural icarin is not active optimal state, needs after being converted into aglycon under the effect of entero-bacte enzyme system, just to be absorbed and brings into play drug effect.
The external biological enzyme process transfers icarin to epimedium aglucone, and the tool specificity is good, pollution-free and transformation efficiency advantages of higher.
At high price (about 40,000 yuans of lg epimedium aglucone), how high reactivity monomer epimedium aglucone further improves its output in industry be the field that the utmost point has Research Significance.Acetone, the butanone etc. of using extract the toxic organic solvent of body more in the method for existing production epimedium aglucone or low glycosyl icarin.And intravital aglycon of natural phant or problem such as the content of low Aglycone is not high, and yield is low.Transfer icarin (about 5,000 yuans of lg icarin) to epimedium aglucone (about 40,000 yuans of lg epimedium aglucone) with biological enzyme; Can avoid the use of the deleterious organic solvent extraction process of body; Easy to operate, reaction temperature and; Can obtain extremely pure aglycon, can be applicable to the industrial mass production of epimedium aglucone.
Thereby learn if change icarin into epimedium aglucone or low sugar icarin, not only improve physiologically active and using value, also promote suitability for industrialized production.
Adding through enzyme is not high or not have the structural transformation of the composition of physiologically active be the high reactivity molecular structure with some physiologically actives, not only improves the physiologically active and the using value of extract, and reducing production costs also promotes suitability for industrialized production.Because epimedium aglucone is easier to absorb with respect to icarin, and the pharmacologically active of aglycon is higher than glycosides.
Summary of the invention
The objective of the invention is biological activity and using value, propose a kind of method that icarin is changed into epimedium aglucone with enzyme reaction in order to improve icarin.
Technical scheme of the present invention is following: a kind of icarin is changed into the method for epimedium aglucone, it is characterized in that this method comprises the steps:
1) icarin is joined in the 30%-70% ethanol system, regulate pH (4-8), system reaches certain temperature (40-70 ℃), stirs temperature control reaction down 30 hours;
2) 2) in above-mentioned reaction system, add naringinase, (standard vigor 475AGUPg),
For containing a kind of enzyme of beta-glucosidase.
Enzyme according to the invention is preferably naringinase.
On the basis of technique scheme, technical program of the present invention also lies in: said concentration of ethanol is 30%.
The invention provides a kind of application naringinase reaction makes icarin change epimedium aglucone into to improve its bioactive method.Under the effect of enzyme, the glycosyl on the icarin hydroxyl is scaled off the epimedium aglucone that becomes higher market price.The present invention can significantly improve the pharmacologically active of icarin, makes it in laboratory study, be easy to effectively use and supply raw materials as the exploitation of Herba Epimedii Chinese patent medicine preparation; And improve the transformation efficiency that icarin changes into aglycon, the production epimedium aglucone is provided, or reduce the difficulty of extracting; Can enlarge simultaneously the processibility and the practical ranges of icarin.
Description of drawings
Figure one uses the acetic acid ethyl acetate extract analytical results for icarin changes the glycosides product.Among the figure: 1 is the icarin standard substance; 2 is epimedium aglucone.
Figure two uses the acetic acid ethyl acetate extract analytical results for icarin changes the glycosides product.Use chloroform: methyl alcohol: water=7.5: 2.5: 0.25 launches for moving phase, under the 245nm UV-light, carries out the TLC qualitative analysis, and among the figure: 1 is the icarin standard substance; 2 is epimedium aglucone.
Embodiment
Instance 1: in the 1000mL triangular flask; Add 10mg icarin standard substance and 400ml30% aqueous ethanolic solution, with 1M NaOH solution adjust pH to 4.0, system reaches 50 ℃ of certain temperatures; The back adds 0.5g naringinase (standard vigor 475AGUPg); At last, under 50 ℃, 200rpm, stirring reaction 30 hours.After reaction finishes; Use and remove carbohydrate and zymoprotein impurity with the ethyl acetate extraction of equal volume, extraction liquid with the G silica-gel plate (100mm * 25mm), chloroform: methyl alcohol=8: 2 is that moving phase is launched; Under the 245nm UV-light, observe and send out and carry out qualitative analysis, result (1.R as shown in Figure 1 with TLC
F icarin standard substance=0.50,2.R
The f epimedium aglucone=0.8), reaction product R
fValue 0.8 is much larger than standard substance R
fValue 0.5 shows through enzyme reaction and has produced the epimedium aglucone of polarity less than icarin that reaction mechanism can be represented with following chemical equation:
Reaction mechanism can be represented with following chemical equation:
Instance 2: in the 1000ml triangular flask; Add 10mg icarin standard substance and 400ml40% aqueous ethanolic solution, with 1M NaOH solution adjust pH to 4.0, system reaches 50 ℃ of certain temperatures; The back adds 0.5g naringinase (standard vigor 475AGUPg); At last, under 50 ℃, 200rpm, stirring reaction 30 hours.After reaction finishes; Use and remove carbohydrate and zymoprotein impurity with the ethyl acetate extraction of equal volume; Extraction liquid is with G silica-gel plate (100mm * 25mm); Chloroform: methyl alcohol: water=7.5: 2.5: 0.25 is that moving phase is launched, observation and send out with TLC and to carry out qualitative analysis, result (R as shown in Figure 2 under the 245nm UV-light
F icarin standard substance=0.42,2.R
The f epimedium aglucone=0.8) reaction product R
fValue 0.8 is much larger than standard substance R
fValue 0.42 shows through enzyme reaction and has produced the epimedium aglucone of polarity less than icarin that reaction mechanism is identical with instance 1.
Instance 3: in the 1000ml triangular flask; Add 10mg icarin standard substance and 400ml30% aqueous ethanolic solution, with 1M NaOH solution adjust pH to 6.0, system reaches 60 ℃ of certain temperatures; The back adds 0.5g naringinase (standard vigor 475AGUPg); At last, under 60 ℃, 200rpm, stirring reaction 30 hours.After reaction finishes; Use and remove carbohydrate and zymoprotein impurity with the ethyl acetate extraction of equal volume; Extraction liquid is with G silica-gel plate (100mm * 25mm); Chloroform: methyl alcohol: water=7.5: 2.5: 0.25 is that moving phase is launched, observation and send out with TLC and to carry out qualitative analysis, result (R as shown in Figure 2 under the 245nm UV-light
F icarin standard substance=0.42,2.R
The f epimedium aglucone=0.8) reaction product R
fValue 0.8 is much larger than standard substance R
fValue 0.42 shows through enzyme reaction and has produced the epimedium aglucone of polarity less than icarin that reaction mechanism is identical with instance 1.
Instance 4: in the 1000ml triangular flask; Add 10mg icarin standard substance and 400ml30% aqueous ethanolic solution, with 1M NaOH solution adjust pH to 5.0, system reaches 50 ℃ of certain temperatures; The back adds 0.5g naringinase (standard vigor 475AGUPg); At last, under 50 ℃, 200rpm, stirring reaction 30 hours.After reaction finishes, use and remove carbohydrate and zymoprotein impurity with the ethyl acetate extraction of equal volume.(100mm * 25mm), chloroform: methyl alcohol=8: 2 is that moving phase is launched to extraction liquid, observation and send out with TLC and to carry out qualitative analysis, result (1.R as shown in Figure 1 under the 245nm UV-light with the G silica-gel plate
F icarin standard substance=0.50,2.R
The f epimedium aglucone=0.8), reaction product R
fValue 0.8 is much larger than standard substance R
fValue 0.5 shows through enzyme reaction and has produced the epimedium aglucone of polarity less than icarin that reaction mechanism is identical with instance 1.
Instance 5: in the 1000ml triangular flask; Add 10mg icarin standard substance and 400ml20% aqueous ethanolic solution, with 1M NaOH solution adjust pH to 6.0, system reaches 50 ℃ of certain temperatures; The back adds 0.5g naringinase (standard vigor 475AGUPg); At last, under 50 ℃, 200rpm, stirring reaction 30 hours.After reaction finishes, use and remove carbohydrate and zymoprotein impurity with the ethyl acetate extraction of equal volume.(100mm * 25mm), chloroform: methyl alcohol=8: 2 is that moving phase is launched to extraction liquid, observation and send out with TLC and to carry out qualitative analysis, result (1.R as shown in Figure 1 under the 245nm UV-light with the G silica-gel plate
F icarin standard substance=0.50,2.R
The f epimedium aglucone=0.8), reaction product R
fValue 0.8 is much larger than standard substance R
fValue 0.5 shows through enzyme reaction and has produced the epimedium aglucone of polarity less than icarin that reaction mechanism is identical with instance 1.
Claims (4)
1. a method that generates epimedium aglucone is characterized in that this method comprises the steps:
1) the icarin standard substance are joined in the 30%-70% ethanol, the pH value is 4-8, and system temperature is 40 ℃ to 70 ℃;
2) in above-mentioned system, add naringinase, the reaction times is 30 o'clock hours.
2. according to the described method of claim 1, it is characterized in that naringinase is made up of β-rhamnosidase and beta-glucosidase.Naringinase (standard vigor 475AGUPg).
3. according to the described method of claim 1, it is characterized in that: temperature is 50 ℃.
4. according to claim 1,2,3 described methods, it is characterized in that: said pH value is 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105177936A CN102453735A (en) | 2010-10-15 | 2010-10-15 | Method for obtaining icaritin from icariin by adopting naringinase |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010105177936A CN102453735A (en) | 2010-10-15 | 2010-10-15 | Method for obtaining icaritin from icariin by adopting naringinase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102453735A true CN102453735A (en) | 2012-05-16 |
Family
ID=46037432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010105177936A Pending CN102453735A (en) | 2010-10-15 | 2010-10-15 | Method for obtaining icaritin from icariin by adopting naringinase |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102453735A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104561178A (en) * | 2014-06-19 | 2015-04-29 | 山东大学（威海） | Method for obtaining anhydroicaritin from icariin by adopting naringinase |
| CN110699263A (en) * | 2019-10-29 | 2020-01-17 | 浙江工业大学 | Aspergillus niger YH-6 and application thereof in improving content of icaritin in epimedium |
| CN111117963A (en) * | 2019-12-30 | 2020-05-08 | 河北北方学院附属第一医院 | Compositions for reducing the effects of anesthetics on nerve cells |
| CN112226395A (en) * | 2020-09-10 | 2021-01-15 | 广西大学 | Escherichia coli engineering bacterium and method for producing icariin through whole-cell catalysis of escherichia coli engineering bacterium |
| CN113355373A (en) * | 2021-06-29 | 2021-09-07 | 劲牌持正堂药业有限公司 | Preparation method of low polycyclic aromatic hydrocarbon icaritin |
-
2010
- 2010-10-15 CN CN2010105177936A patent/CN102453735A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104561178A (en) * | 2014-06-19 | 2015-04-29 | 山东大学（威海） | Method for obtaining anhydroicaritin from icariin by adopting naringinase |
| CN110699263A (en) * | 2019-10-29 | 2020-01-17 | 浙江工业大学 | Aspergillus niger YH-6 and application thereof in improving content of icaritin in epimedium |
| CN111117963A (en) * | 2019-12-30 | 2020-05-08 | 河北北方学院附属第一医院 | Compositions for reducing the effects of anesthetics on nerve cells |
| CN112226395A (en) * | 2020-09-10 | 2021-01-15 | 广西大学 | Escherichia coli engineering bacterium and method for producing icariin through whole-cell catalysis of escherichia coli engineering bacterium |
| CN112226395B (en) * | 2020-09-10 | 2022-07-05 | 广西大学 | Escherichia coli engineering bacterium and method for producing icariin through whole-cell catalysis of escherichia coli engineering bacterium |
| CN113355373A (en) * | 2021-06-29 | 2021-09-07 | 劲牌持正堂药业有限公司 | Preparation method of low polycyclic aromatic hydrocarbon icaritin |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104561178A (en) | Method for obtaining anhydroicaritin from icariin by adopting naringinase | |
| CN102453735A (en) | Method for obtaining icaritin from icariin by adopting naringinase | |
| CN101225119B (en) | Porphyra yezoensis polysaccharide and protein synchronous ultrasonic auxiliary extraction method | |
| CN105648021A (en) | Preparation method for rare ginsenoside C-K and F1 and four kinds of isomer ginsengenin | |
| CN1982438A (en) | Bacillus and production of monodesmosidic panasaponin and aglucon therewith | |
| CN102311985A (en) | Preparation method of baohuoside I | |
| CN105732381A (en) | Compounds from antrodia camphorata, method for preparing the same and use thereof | |
| CN106520896A (en) | Method for preparing dexamethasone intermediate product through one-step microbial fermentation and transformation | |
| CN103193854B (en) | The separation and purification of betulin and the biological and chemical method for transformation of betulinic acid | |
| CN102311984A (en) | Method of preparing Baohuoside I from epimedium | |
| CN104817609A (en) | Notoginsenoside compound with liver cancer-resistant activity and its preparation method and use | |
| CN102453736A (en) | Method for preparing quercetin by enzyme reaction of hyperoside | |
| CN104262443B (en) | The preparation method and application of polyhydroxy sterol class monomeric compound | |
| CN103214543B (en) | New Crategolic acid derivative, its preparation method and the application in antitumor drug thereof | |
| CN102295677B (en) | In the salicornia europaeal of North America, triterpenoid saponin and its production and use falls in one | |
| CN103204894A (en) | Novel corosolic acid derivative, preparation method thereof and application thereof in preparing diabetes medicaments | |
| CN104370931A (en) | New flavone compound as well as preparation method and application thereof | |
| CN103965279A (en) | Novel ginsenoside acid degradation compound as well as preparation method and medical application thereof | |
| CN101508965B (en) | Process of preparing 20(S)-ginsenoside Rh1 with streptomycete fermentation of pseudo-ginseng saponin | |
| CN101693913A (en) | Process for preparing rusco monoglycosides high-efficiently | |
| CN110117630A (en) | A kind of method that preparation phenethyl caffeate glucosides was applied and was used in the glycosylation of dextransucrase | |
| CN108864130B (en) | Enmein derivative and preparation method and application thereof | |
| CN106749492A (en) | A kind of steroid saponin compound and its preparation method and application | |
| CN104693263B (en) | A kind of arasaponin compound with anti-tumor activity and preparation method and application | |
| CN103882075A (en) | Process for obtaining ginkgolide B by utilizing tremella aurantialba strains to transform ginkgo biloba extracts |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20120516 |