CN1702174A - Method for improving polarity of flavonoid glycoside - Google Patents
Method for improving polarity of flavonoid glycoside Download PDFInfo
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- CN1702174A CN1702174A CN 200510068343 CN200510068343A CN1702174A CN 1702174 A CN1702174 A CN 1702174A CN 200510068343 CN200510068343 CN 200510068343 CN 200510068343 A CN200510068343 A CN 200510068343A CN 1702174 A CN1702174 A CN 1702174A
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- quercetin
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- flavonoid glycoside
- flavone
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- 238000000034 method Methods 0.000 title claims abstract description 29
- 229930182486 flavonoid glycoside Natural products 0.000 title claims abstract description 17
- 150000007955 flavonoid glycosides Chemical class 0.000 title claims abstract description 17
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims abstract description 69
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims abstract description 64
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims abstract description 36
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims abstract description 36
- 235000005875 quercetin Nutrition 0.000 claims abstract description 36
- 229960001285 quercetin Drugs 0.000 claims abstract description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229930003944 flavone Natural products 0.000 claims abstract description 21
- 235000011949 flavones Nutrition 0.000 claims abstract description 21
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 claims abstract description 20
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- 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 3
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- FDRQPMVGJOQVTL-UHFFFAOYSA-N quercetin rutinoside Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 FDRQPMVGJOQVTL-UHFFFAOYSA-N 0.000 description 9
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Abstract
The present invention discloses a method for improving polarity of flavonoid glycoside reacting flavone aglycon, glucosyltransferase and sugarsubstrate in ethanol water solution with 0-90% thickness. The weight volume ratio of said flavone aglycon and ethanol water solution is 0.03-0.07g/100ml. said reacting temperature is 20-90 DEG C, the reacting time is 1-30 hours. The invention can apparently improve the water-solubility of flavone aglycon such as quercetin and naphthol, which are easily dissolved by polar solvent such as water or ethanol in industry production, the quercetin glucoside and the naphthol glucoside as medical production, comparing with the quercetin and naphthol, are easily to be used by organism; the invention also can improve the extracting ratio of flavonoid in natural product which reduces the ethanol using quantity in the extracting process; in addition, the invention also can improve the processability of total flavone and pure total flavone product, mean time expand its practical application range.
Description
Technical field
The present invention relates to a kind of raising compound polar method, particularly relate to a kind of method that improves polarity of flavonoid glycoside.
Background technology
Flavone aglycone is a kind of main existence form of flavonoid compound (Flavonoid compounds).
Quercetin (Quercetin) and kaempferol (Kaempferol) are the representative substances of Flavone aglycone, and they all are to be the fat-soluble cpds of basic structure with C6-C3-C6, and polarity is low, only is dissolved in non-polar solvents such as ethyl acetate, chloroform, ether.At present, Quercetin and kaempferol are mainly derived from the extraction of natural product.
The molecular formula of Quercetin is C
15H
10O
5, its chemical structural formula is suc as formula shown in the I, and it and derivative thereof have multiple physiologically active, as have anticancer, antiviral, pharmacological action such as treatment cardiovascular disorder etc.They are widely distributed in vegitabilia, and wherein Quercetin extensively is present in the flower, leaf, fruit of plant.Medicinal plant such as sophora flower, Leafy twigs of Oriental Arborvitae, Rhizoma Alpiniae Officinarum, Flos Farfarae, loranthus parasiticus and pseudo-ginseng all contain Quercetin, and especially the content of Quercetin is the highest in buckwheat, sea-buckthorn, hawthorn and the onion.Chinese scholars is for the extraction of Quercetin and derivative thereof, pure system, pharmacology and clinically carried out a large amount of research.In actual applications, Quercetin is many is used with glycoside form such as rutin, Quercitroside, Quercetin 3-galactoside etc.From the angle of pharmacokinetics, the Quercetin glycosides is absorbed than Quercetin is easier in vivo, also demonstrates same physiologically active in pharmacological research.Acetone, the butanone of using extract as solvent more in the existing method of producing Quercetin, but these organic solvents can produce deleterious effect to body, and use it for suitability for industrialized production and can produce problems such as security is low, seriously polluted, cost height.For fear of using to the deleterious organic solvent of body, in the leaching process of beverage and pharmaceuticals many with pure water as solvent.But because natural Quercetin polarity is low, need to use 60% above aqueous solution of alcohol in actual applications, cause the ethanol consumption big, the production cost height.
(formula I)
The molecular formula of kaempferol is C
15H
10O
6Its chemical structural formula is suc as formula shown in the II, it and derivative thereof are widely distributed in vegitabilia, and have pharmacological action such as antisepsis and anti-inflammation, and a lot of Chinese medicines such as South Dodder Seed Chinese Dodder Seed, Herba Hyperici perforati, Chinese toon, stamen nelumbini, rhizoma sparganic, hawthorn, Semen Descurainiae and Herba Erigerontis all contain kaempferol.Because the polarity of kaempferol is lower, in ethanol water solvent, be difficult to dissolving, in actual production, the polarity of kaempferol is the bigger the better.
(formula II)
Therefore, for the range of application that enlarges Flavone aglycones such as Quercetin, kaempferol and the utilising efficiency in body thereof, press for its polar method of a kind of raising.
Summary of the invention
The purpose of this invention is to provide a kind of method that improves polarity of flavonoid glycoside.
The method of raising polarity of flavonoid glycoside provided by the present invention is that Flavone aglycone, transglucosidase and glycosyl substrate are reacted in concentration is the aqueous ethanolic solution of 0%-90%.
The source of described Flavone aglycone is widely, can be purifying, can be chemosynthesis, also can be the natural product that contains Flavone aglycone.
The weightmeasurement ratio of described Flavone aglycone and aqueous ethanolic solution is/100 milliliters of 0.03-0.07 grams.
The pH value of described aqueous ethanolic solution is 2-9, and concentration of ethanol is preferably 40%.
Described temperature of reaction is 20-90 ℃, and the reaction times is 1-30 hour.
Described transglucosidase can be any one transglucosidase, is preferably glucuroide, more preferably spirizyme plus glucuroide, suhong475 glucuroide.The final concentration 1600-1900IU/100mL of transglucosidase in the described aqueous ethanolic solution.
The ratio of weight and number of described Flavone aglycone and glycosyl substrate is 1: 4.5-5.
Described glycosyl substrate can be dextrin, starch or maltose.
The present invention is particularly useful for Quercetin, kaempferol and the natural product that contains Quercetin or kaempferol.
The invention provides a kind of application transglucosidase reaction makes Flavone aglycone monomers such as Quercetin, kaempferol change corresponding flavonoid glycoside into to improve its polar method.Under the effect of transglucosidase, glycosyl is transferred on the oh group of Flavone aglycone in the glycosyl substrate, thereby produces polarity enhanced glycoside material.The present invention can significantly improve the water-soluble of Flavone aglycones such as Quercetin and kaempferol, make its in industrial production easily by water or ethanol isopolarity dissolution with solvents, Quercetin glycosides as pharmaceutical prod is compared with Quercetin, kaempferol with the kaempferol glycosides, is easilier utilized by body; Also can improve the extraction yield of Flavonoid substances in the natural product, thereby reduce the ethanol consumption in its leaching process; In addition, the present invention has also improved the workability of total flavones and true yellow ketone goods, can enlarge its practical ranges simultaneously.
Description of drawings
Fig. 1 changes glycosides product acetic acid ethyl acetate extract analytical results for Quercetin
Fig. 2 changes glycosides product acetic acid ethyl acetate extract analytical results for kaempferol
Embodiment
Method therefor is ordinary method if no special instructions among the following embodiment.
The polarity of embodiment 1, raising Quercetin
In the 1000mL triangular flask, add 0.025g Quercetin, 0.1125g maltose and 50mL 30% aqueous ethanolic solution, with 1N NaOH solution adjust pH to 6.0, add penicillium decumbens glucoside enzyme solution (6.23IU/mL) 0.5mL then, at last, under 50 ℃, 200rpm, stirring reaction 30 hours.After reaction finishes, ethyl acetate extraction reaction product (with the positive contrast of rutin) with equal volume, (10cm * 20cm), benzene: ethyl acetate: acetone: acetate=10: 8: 2: 2 is that moving phase is launched to extraction liquid with the GF254 silica-gel plate, observe fluorescence and carry out qualitative and quantitative analysis with the TLC method under the 365nm ultraviolet lamp, the result is (1.R as shown in Figure 1
The f Quercetin=0.68,
2.R
The f Quercetin changes the glycosides product=0.30,3.R
The f rutin=0.01), show by changeing the glycosides reaction to have produced the Quercetin glycosides of polarity that it is easily dissolved by water or ethanol isopolarity solvent, and reaction mechanism can be represented with following chemical equation in industrial production greater than Quercetin:
The polarity of embodiment 2, raising kaempferol
In the 1000mL triangular flask, add 0.015g kaempferol, 0.072g maltose and 50mL 60% aqueous ethanolic solution, with 1N NaOH solution adjust pH to 9.0, add spirizyme plus glucuroide (standard vigor 400AGU/g) 2.0mL then, under 30 ℃, 200rpm, stirring reaction 1 hour.After reaction finishes, ethyl acetate extraction (with the positive contrast of rutin) with equal volume, (10cm * 20cm), benzene: ethyl acetate: acetone: acetate=10: 8: 2:2 is that moving phase is launched to extraction liquid with the GF254 silica-gel plate, observe fluorescence and carry out qualitative and quantitative analysis with the TLC method under the 365nm ultraviolet lamp, the result is (1.R as shown in Figure 2
The f kaempferol=0.87,2.R
The f kaempferol changes the glycosides product=0.10,3.R
The f rutin=0.01), show after changeing the glycosides reaction to have produced the kaempferol glycosides of polarity that it is easily dissolved by water or ethanol isopolarity solvent, and reaction mechanism can be represented with following chemical equation in industrial production greater than kaempferol:
The polarity of embodiment 3, raising Quercetin
In the 1000mL triangular flask, add 0.025g Quercetin, 0.125g maltose and 50mL 30% aqueous ethanolic solution, with 1N NaOH solution adjust pH to 2.0, add suhong475 glucuroide (standard vigor 475AGU/g) 0.5mL then, at 90 ℃, under the 200rpm, stirring reaction 30 hours.After reaction finishes, with equal volume ethyl acetate extraction (with the positive contrast of rutin), (10cm * 20cm), benzene: ethyl acetate: acetone: acetate=10: 8: 2: 2 is that moving phase is launched to extraction liquid with the GF254 silica-gel plate, observe fluorescence and carry out qualitative and quantitative analysis with the TLC method under the 365nm ultraviolet lamp, the result is (1.R as shown in Figure 1
The f Quercetin=0.68,2.R
The f Quercetin changes the glycosides product=0.30,3.R
The f rutin=0.01), shows by changeing the glycosides reaction to have produced the Quercetin glycosides of polarity that it is easily dissolved by water or ethanol isopolarity solvent, and reaction mechanism is identical with embodiment 1 in industrial production greater than Quercetin.
The polarity of embodiment 4, raising kaempferol
In the 1000mL triangular flask, add 0.035g kaempferol, 0.168g maltose and 50mL 10% aqueous ethanolic solution,, add suhong475 glucuroide (standard vigor 475AGU/g) 0.5mL then with 1N NaOH solution adjust pH to 6.0, under 50 ℃, 200rpm, stirring reaction 20 hours.After reaction finishes, with equal volume ethyl acetate extraction (with the positive contrast of rutin), (10cm * 20cm), benzene: ethyl acetate: acetone: acetate=10: 8: 2: 2 is that moving phase is launched to extraction liquid with the GF254 silica-gel plate, observe fluorescence and carry out qualitative and quantitative analysis with the TLC method under the 365nm ultraviolet lamp, the result is (1.R as shown in Figure 2
The f kaempferol=0.87,2.R
The f kaempferol changes the glycosides product=0.10,3.R
The f rutin=0.01), shows after changeing the glycosides reaction to have produced the kaempferol glycosides of polarity that it is easily dissolved by water or ethanol isopolarity solvent, and reaction mechanism is identical with embodiment 2 in industrial production greater than kaempferol.
Claims (10)
1, a kind of method that improves polarity of flavonoid glycoside is that Flavone aglycone, transglucosidase and glycosyl substrate are reacted in concentration is the aqueous ethanolic solution of 0%-90%.
2, the method for raising polarity of flavonoid glycoside according to claim 1 is characterized in that: the weightmeasurement ratio of described Flavone aglycone and aqueous ethanolic solution is/100 milliliters of 0.03-0.07 grams.
3, the method for raising polarity of flavonoid glycoside according to claim 1 is characterized in that: the pH value of described aqueous ethanolic solution is 2-9, and concentration of ethanol is 40%.
4, the method for raising polarity of flavonoid glycoside according to claim 1 is characterized in that: described temperature of reaction is 20-90 ℃, and the reaction times is 1-30 hour.
5, the method for raising polarity of flavonoid glycoside according to claim 1 is characterized in that: described transglucosidase is a glucuroide.
6, the method for raising polarity of flavonoid glycoside according to claim 5 is characterized in that: described glucuroide is spirizyme plus glucuroide, suhong475 glucuroide.
7, according to the method for the arbitrary described raising polarity of flavonoid glycoside of claim 1-6, it is characterized in that: the final concentration of transglucosidase is 1600-1900IU/100mL in the described aqueous ethanolic solution.
8, according to the method for the arbitrary described raising polarity of flavonoid glycoside of claim 1-6, it is characterized in that: the ratio of weight and number of described Flavone aglycone and glycosyl substrate is 1: 4.5-5.
9, according to the method for the arbitrary described raising polarity of flavonoid glycoside of claim 1-6, it is characterized in that: described glycosyl substrate is dextrin, starch or maltose.
10, according to the method for the arbitrary described raising polarity of flavonoid glycoside of claim 1-6, it is characterized in that: described Flavone aglycone is Quercetin or kaempferol.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250979A (en) * | 2011-04-12 | 2011-11-23 | 安康中科麦迪森天然药业有限公司 | Method for extracting and separating kaempferol from Ligustrum sinense branches and leaves |
| CN102489038A (en) * | 2011-11-29 | 2012-06-13 | 华东理工大学 | Method for extracting flavones in Chinese herbal medicine by surfactant cooperated supersonic wave-enzymatic hydrolysis |
| CN105086002A (en) * | 2015-08-11 | 2015-11-25 | 华南理工大学 | Spirochete-dextrin quercetin clathrate compound and preparing method thereof |
| US20210299033A1 (en) * | 2020-03-26 | 2021-09-30 | Johnson & Johnson Consumer Inc. | Compositions comprising carum carvi and rosmarinus officinalis extracts and methods of using same |
| CN114041598A (en) * | 2021-11-26 | 2022-02-15 | 江南大学 | Processing method for improving quality and enhancing efficiency of fat-soluble plant compound and application |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3916682B2 (en) * | 1995-09-25 | 2007-05-16 | ユニチカ株式会社 | Method for producing glycoside |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102250979A (en) * | 2011-04-12 | 2011-11-23 | 安康中科麦迪森天然药业有限公司 | Method for extracting and separating kaempferol from Ligustrum sinense branches and leaves |
| CN102250979B (en) * | 2011-04-12 | 2013-01-02 | 安康中科麦迪森天然药业有限公司 | Method for extracting and separating kaempferol from Ligustrum sinense branches and leaves |
| CN102489038A (en) * | 2011-11-29 | 2012-06-13 | 华东理工大学 | Method for extracting flavones in Chinese herbal medicine by surfactant cooperated supersonic wave-enzymatic hydrolysis |
| CN102489038B (en) * | 2011-11-29 | 2014-09-24 | 华东理工大学 | Method for extracting flavones in Chinese herbal medicine by surfactant cooperated supersonic wave-enzymatic hydrolysis |
| CN105086002A (en) * | 2015-08-11 | 2015-11-25 | 华南理工大学 | Spirochete-dextrin quercetin clathrate compound and preparing method thereof |
| US20210299033A1 (en) * | 2020-03-26 | 2021-09-30 | Johnson & Johnson Consumer Inc. | Compositions comprising carum carvi and rosmarinus officinalis extracts and methods of using same |
| CN114041598A (en) * | 2021-11-26 | 2022-02-15 | 江南大学 | Processing method for improving quality and enhancing efficiency of fat-soluble plant compound and application |
| CN114041598B (en) * | 2021-11-26 | 2023-03-28 | 江南大学 | Processing method for improving quality and enhancing efficiency of fat-soluble plant compound and application |
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