CN102876746A - Method of ionic liquid cosolvent effect reinforced enzymatic synthesis of isoquercitrin - Google Patents
Method of ionic liquid cosolvent effect reinforced enzymatic synthesis of isoquercitrin Download PDFInfo
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- CN102876746A CN102876746A CN2012103832852A CN201210383285A CN102876746A CN 102876746 A CN102876746 A CN 102876746A CN 2012103832852 A CN2012103832852 A CN 2012103832852A CN 201210383285 A CN201210383285 A CN 201210383285A CN 102876746 A CN102876746 A CN 102876746A
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Abstract
The invention relates to a method of ionic liquid cosolvent effect reinforced enzymatic synthesis of isoquercitrin. The method comprises a reaction system for synthesizing isoquercitrin by hydrolyzing rutin with a hesperidin enzyme or a naringin enzyme. The reaction system comprises a rutin mother liquid prepared by a disodium hydrogen phosphate-citrate buffer solution and a hesperidin enzyme liquid or a naringin enzyme liquid. The reaction system contains an ionic liquid formed by cations and anions. In the ionic liquid cosolvent system, the prepared isoquercitrin by hydrolyzing rutin under enzyme catalysis has increased reaction rate and higher yield than that in a conventional aqueous solution system, so that the ionic liquid cosolvent system provides a novel reaction medium for the production of isoquercitrin. The method is simple in operation and mild in reaction conditions, is environment-friendly, and has good application prospects.
Description
Technical field
The invention belongs to enzyme process synthesised food additive agent field, be specifically related to the method that a kind of ionic liquid co-solvent effect is strengthened the synthetic isoquercitrin of enzymatic.
Background technology
Prior art: isoquercitrin (Isoquercitrin), it is Quercetin-3-O-β-D-Glucose glycosides (Quercetin-3-glucose), that very rare a kind of of occurring in nature has significant oxidation-resistance, the bioactive flavonoid compound such as antitumor, it is the gourmet food additive competitively developed of each large medicine food company in the world, ancillary drug or effective ingredient, also be the synthesis material (Toxicology of Multifunction foodstuff additive EMIQ (Enzymatically Modified Isoquercitrin) in the world, 2010,268 (3): 213-218).Separation and Extraction isoquercitrin from natural phant, these class methods need to be used a large amount of organic solvents usually, and time and effort consuming, and production efficiency is low.A large amount of acid waste water serious environment pollutions that acid hydrolysis produces, and Quercetin and isoquercitrin and deposit in the rutin acid hydrolysis process, this has also increased cost (African Journal of Biotechnology, 2011,10 (8): 1460-1466) of later stage separation and purification.The enzymically hydrolyse technique of the directed synthetic isoquercitrin of the bio-transformation rutin of setting up at present (Journal ofMolecular Catalysis B:Enzymatic, 2012,81:34-42) be the production technique of the tool prospect of the preparation isoquercitrin of generally acknowledging.Thereby the speed and the efficient that improve the Glycosylase enzymatic reaction are one of gordian techniquies that improves rutin transformation efficiency and isoquercitrin yield.
Ionic liquid (Ionic Liquids, ILs) is to be made of positively charged ion and electronegative ion, is liquid state between-100 ℃ and 200 ℃.ILs has the unexistent advantages of conventional solvent such as vapour pressure is little, solvability good, non-volatile.Ionic liquid has very strong plasticity-, namely can make up the polarity that different zwitterions comes the adaptive response substrate, thereby the solvability of raising substrate and enzyme ' s reaction speeding (Journal of Molecular Catalysis B:Enzymatic, 2010,65:68-72).Thermophilic protease in ionic liquid, have higher thermostability (BiotechnologyProgress, 2000,16:1129-1131), under 80 ℃ of conditions, at ionic liquid [BMIM] [PF
6] behind the water-bath 20h, enzymic activity has increased 20%(Green Chemistry, 2002,4:147-151).Lipase is through ionic liquid [Bmim] [PF
6], [Emim] [Tf
2N], [Bmim] [BF
4] and [Emim] [BF
4] after the processing, activity increases respectively 1.81,1.66,1.56 and 1.6 times of (Journal ofMolecular Catalysis B:Enzymatic, 2007,45 (3-4): 118-121).Negatively charged ion in the ionic liquid is to affect the important factor that enzyme is lived, [NO
3], [CF
3CO
2], [CH
3CO
2] geometric ratio [PF
6] have a higher nucleophilicity, so that they can be better in lipase positively charged site be combined, thereby the conformation that affects enzyme affects the activity of enzyme (Journal of the American Chemical Society, 2003,125 (14): 4125-4131).Reported among the patent US2008299623A1 that in enzymic catalytic reaction the reaction medium that contains ionic liquid can improve the substrate solvability, improved activity and the selectivity of enzyme, reduced the generation of product inhibition and side reaction.Lipase CALB is at ionic liquid [EMIM] [BF
4] in the esterification of catalysis glucose have very high selectivity, at [MOEMIM] [BF
4] in be swift in response, and the solubleness of glucose can reach 5g/L 55 ℃ the time, be in the acetone more than 100 times (Current Opinion in Biotechnology, 2003,14:432-437).Beta-galactosidase enzymes catalyzing N-acetylglucosamine is produced in the reaction of lactose, because the competitive secondary hydrolysis of product N-acetyl lactosamine is suppressed productive rate.This reaction is at [MMIm] [MeSO
4]/water (V/V25: when carrying out 75), productive rate reaches 58%, and when carrying out in water-buffer solution system, productive rate only is 30%(Biotechnology and bioengineering, and 2006,95 (6): 1093-1100).Yet, there is not yet with ionic liquid and make the report that cosolvent is strengthened the synthetic isoquercitrin of enzymatic.
In traditional reaction system take aqueous buffer solution as medium, the solubleness of rutin is low, and enzymatic reaction efficient is poor.In this patent, in traditional reactant aqueous solution system, add ionic liquid, be conducive to improve substrate solubleness, improve enzymatic reaction efficient, and easy and simple to handle, environmentally friendly.
Summary of the invention
The technical problem that solves: for the deficiencies in the prior art, the invention provides the method that a kind of ionic liquid co-solvent effect is strengthened the synthetic isoquercitrin of enzymatic, the method can improve the reaction efficiency of the synthetic isoquercitrin of enzymatic hydrolysis rutin widely.
Technical scheme: the ionic liquid co-solvent effect is strengthened the method for the synthetic isoquercitrin of enzymatic, the reaction system that comprises the synthetic isoquercitrin of hesperidinase or naringinase hydrolyzing rutin, comprise in this reaction system with Sodium phosphate dibasic-citrate buffer solution preparation rutin mother liquor, and hesperidinase liquid or naringinase liquid, in this reaction system, contain ionic liquid, described ionic liquid is formed by positively charged ion and negatively charged ion cooperation, cation type is [Emim], [Bmim], [TOMA], [Hmim], [Nmim] or [EMPY], and anionic type is [BF
4], [PF
6], [Tf
2N], [HSO
4], [TfO] or [C
4F
9SO
3], the zwitterion ratio is 1: 1, the concentration of rutin was 0.26-0.97g/L after the rutin mother liquor mixed with ionic liquid, pH is 3-10, add by volume the ionic liquid of 5-50%, the rutin mother liquor of 45-90% and hesperidinase liquid or the naringinase liquid of 5-45% in the reaction system, range of reaction temperature is 20-60 ℃, and the vibration rotating speed is 50-300r/min, and reaction time range is 1-40h.
The concentration of rutin was 0.72g/L after the rutin mother liquor of damping fluid preparation mixed with ionic liquid.
Rutin mother liquor and the mixed pH of ionic liquid of damping fluid preparation are 5.
Add by volume 10% ionic liquid, 72% rutin mother liquor and 18% hesperidinase liquid in the reaction system.
The range of reaction temperature of reaction system is 40 ℃.
The vibration rotating speed of reaction system is 120r/min.
The reaction time range of reaction system is 7h.
HPLC detected and shows that the yield of isoquercitrin will be higher than the yield of buffer solution system under the same reaction conditions in the ionic liquid cosolvent system after reaction finished.
Beneficial effect:
The enzymatic hydrolysis rutin prepares isoquercitrin in the ionic liquid cosolvent system, and speed of reaction increases, and efficiency of pcr product is higher than traditional water solution system, and therefore, the ionic liquid cosolvent system provides new reaction medium for the production of isoquercitrin.The method is simple to operate, and reaction conditions is gentle, and is environmentally friendly, has a good application prospect.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used for explanation the present invention and be not used in and limit the scope of the invention.Should be understood that in addition that after having read the content that the present invention lectures those skilled in the art can make any change and revise the present invention, these equivalent form of values fall within the described claims limited range of the application equally.
Use the HPLC method to detect simultaneously rutin and isoquercitrin, chromatographic condition in the embodiment of the invention: Alltima C
18(250 * 4.6mm, 5 μ m), moving phase: 0.02% phosphoric acid-acetonitrile (80: 20, V/V); Detect wavelength: 360nm; Flow velocity: 1.0mL/min; Sample size: 20 μ L.Use the HPLC method to detect Quercetin, chromatographic condition: Alltima C
18(250 * 4.6mm, 5 μ m), moving phase: 0.5mol/LpH4.0 Ammoniom-Acetate damping fluid-acetonitrile (73: 27, V/V); Detect wavelength: 360nm; Flow velocity: 1.0mL/min; Sample size: 20 μ L.
Wherein, the method for calculation of rutin transformation efficiency, isoquercitrin mole yield and Quercetin mole yield are as follows:
Take by weighing 0.1g hesperidinase or naringinase, be dissolved in water, be settled to 10mL, get hesperidinase liquid or the naringinase liquid of 0.01g/mL.
Embodiment 1
With the rutin mother liquor of the 0.26g/L of Sodium phosphate dibasic-citrate buffer solution preparation pH=3.0, with ionic liquid [the Emim] [BF of volume ratio 5%
4], the zwitterion ratio is that the hesperidinase liquid of 1: 1,90% rutin mother liquor and 5% consists of reaction system, under 60 ℃ of conditions, and 300r/min oscillatory reaction 1h.After reaction finished, HPLC detected rutin, isoquercitrin and Quercetin.Rutin transformation efficiency, isoquercitrin mole yield and Quercetin mole yield are respectively 30%, 23% and 0.5%, compare with the buffer solution system under the similarity condition, and isoquercitrin mole yield has improved 0.8%.
Embodiment 2
With the rutin mother liquor of the 0.41g/L of Sodium phosphate dibasic-citrate buffer solution preparation pH=10.0, with ionic liquid [the Bmim] [BF of volume ratio 50%
4], the zwitterion ratio is that the hesperidinase liquid of 1: 1,45% rutin mother liquor and 5% consists of reaction system, under 20 ℃ of conditions, and 50r/min oscillatory reaction 40h.After reaction finished, HPLC detected rutin, isoquercitrin and Quercetin.Rutin transformation efficiency, isoquercitrin mole yield and Quercetin mole yield are respectively 30%, 15% and 1%, compare with the buffer solution system under the similarity condition, and isoquercitrin mole yield has improved 2%.
Embodiment 3
With the rutin mother liquor of the 0.82g/L of Sodium phosphate dibasic-citrate buffer solution preparation pH=5.0, with ionic liquid [the Emim] [BF of volume ratio 10%
4], the zwitterion ratio is that the hesperidinase liquid of 1: 1,72% rutin mother liquor and 18% consists of reaction system, under 40 ℃ of conditions, and 120r/min oscillatory reaction 7h.After reaction finished, HPLC detected rutin, isoquercitrin and Quercetin.Rutin transformation efficiency, isoquercitrin mole yield and Quercetin mole yield are respectively 94%, 96% and 11%, compare with the buffer solution system under the similarity condition, and isoquercitrin mole yield has improved 89%.
Embodiment 4
With the rutin mother liquor of the 0.29g/L of Sodium phosphate dibasic-citrate buffer solution preparation pH=7.0, with ionic liquid [the Bmim] [Tf of volume ratio 50%
2N], the zwitterion ratio is that the hesperidinase liquid of 1: 1,40% rutin mother liquor and 10% consists of reaction system, under 40 ℃ of conditions, 120r/min oscillatory reaction 24h.After reaction finished, HPLC detected rutin, isoquercitrin and Quercetin.Rutin transformation efficiency, isoquercitrin mole yield and Quercetin mole yield are respectively 98%, 53% and 2%, compare with the buffer solution system under the similarity condition, and isoquercitrin mole yield has improved 5%.
Embodiment 5
With the rutin mother liquor of the 0.97g/L of glycine-sodium hydrate buffer solution preparation pH=9.0, with ionic liquid [the Bmim] [BF of volume ratio 10%
4], the zwitterion ratio is that the hesperidinase liquid of 1: 1,72% rutin mother liquor and 18% consists of reaction system, under 40 ℃ of conditions, and 120r/min oscillatory reaction 12h.After reaction finished, HPLC detected rutin, isoquercitrin and Quercetin.Rutin transformation efficiency, isoquercitrin mole yield and Quercetin mole yield are respectively 98%, 99% and 2%, compare with the buffer solution system under the similarity condition, and isoquercitrin mole yield has improved 60%.
Embodiment 6
With the rutin mother liquor of the 0.29g/L of Sodium phosphate dibasic-citrate buffer solution preparation pH=7.0, with ionic liquid [the Emim] [BF of volume ratio 5%
4], the zwitterion ratio is that the hesperidinase liquid of 1: 1,50% rutin mother liquor and 45% consists of reaction system, under 30 ℃ of conditions, and 50r/min oscillatory reaction 40h.After reaction finished, HPLC detected rutin, isoquercitrin and Quercetin.Rutin transformation efficiency, isoquercitrin mole yield and Quercetin mole yield are respectively 82%, 48% and 10%, compare with the buffer solution system under the similarity condition, and isoquercitrin mole yield has improved 3%.
Embodiment 7
With the rutin mother liquor of the 0.29g/L of Sodium phosphate dibasic-citrate buffer solution preparation pH=7.0, with ionic liquid [the Emim] [BF of volume ratio 5%
4], the zwitterion ratio is that the naringinase liquid of 1: 1,50% rutin mother liquor and 45% consists of reaction system, under 30 ℃ of conditions, and 120r/min oscillatory reaction 40h.After reaction finished, HPLC detected rutin, isoquercitrin and Quercetin.Rutin transformation efficiency, isoquercitrin mole yield and Quercetin mole yield are respectively 65%, 37% and 9%, compare with the buffer solution system under the similarity condition, and isoquercitrin mole yield has improved 2%.
Claims (7)
1. the ionic liquid co-solvent effect is strengthened the method for the synthetic isoquercitrin of enzymatic, the reaction system that comprises the synthetic isoquercitrin of hesperidinase or naringinase hydrolyzing rutin, comprise in this reaction system with Sodium phosphate dibasic-citrate buffer solution preparation rutin mother liquor, and hesperidinase liquid or naringinase liquid, it is characterized in that in this reaction system, containing ionic liquid, described ionic liquid is formed by positively charged ion and negatively charged ion cooperation, cation type is [Emim], [Bmim], [TOMA], [Hmim], [Nmim] or [EMPY], and anionic type is [BF
4], [PF
6], [Tf
2N], [HSO
4], [TfO] or [C
4F
9SO
3], the zwitterion ratio is 1: 1, the concentration of rutin was 0.26-0.97g/L after the rutin mother liquor mixed with ionic liquid, pH is 3-10, add by volume the ionic liquid of 5-50%, the rutin mother liquor of 45-90% and hesperidinase liquid or the naringinase liquid of 5-45% in the reaction system, range of reaction temperature is 20-60 ℃, and the vibration rotating speed is 50-300r/min, and reaction time range is 1-40h.
2. ionic liquid co-solvent effect according to claim 1 is strengthened the method for the synthetic isoquercitrin of enzymatic, and the rutin mother liquor that it is characterized in that the damping fluid preparation mixes with ionic liquid afterwards that the concentration of rutin is 0.72g/L.
3. ionic liquid co-solvent effect according to claim 1 is strengthened the method for the synthetic isoquercitrin of enzymatic, it is characterized in that rutin mother liquor and the mixed pH of ionic liquid of damping fluid preparation is 5.
4. ionic liquid co-solvent effect according to claim 1 is strengthened the method for the synthetic isoquercitrin of enzymatic, it is characterized in that adding by volume in the reaction system 10% ionic liquid, 72% rutin mother liquor and 18% hesperidinase liquid.
5. ionic liquid co-solvent effect according to claim 1 is strengthened the method for the synthetic isoquercitrin of enzymatic, and the range of reaction temperature that it is characterized in that reaction system is 40 ℃.
6. ionic liquid co-solvent effect according to claim 1 is strengthened the method for the synthetic isoquercitrin of enzymatic, and the vibration rotating speed that it is characterized in that reaction system is 120r/min.
7. ionic liquid co-solvent effect according to claim 1 is strengthened the method for the synthetic isoquercitrin of enzymatic, and the reaction time range that it is characterized in that reaction system is 7h.
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Cited By (8)
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|---|---|---|---|---|
| CN103613623A (en) * | 2013-11-28 | 2014-03-05 | 江苏科技大学 | Application of multistage solvent extraction method in enzymatic synthesis of isoquercitrin |
| CN103627756A (en) * | 2013-11-26 | 2014-03-12 | 江苏科技大学 | Method for enzymatic synthesis of isoquercitrin by using continuous-flow tubular microreactor |
| CN103667403A (en) * | 2013-12-17 | 2014-03-26 | 江苏科技大学 | Segmented flow microreaction technology for enzymatic synthesis of isoquercitrin in biphasic system |
| CN105969826A (en) * | 2016-06-17 | 2016-09-28 | 江苏科技大学 | Method for synthesizing isoquercitrin with nano-particle immobilized enzyme special for microreactor |
| CN106086123A (en) * | 2016-06-17 | 2016-11-09 | 江苏科技大学 | A kind of application ionic liquid improves the water miscible method of flavone compound |
| CN106119319A (en) * | 2016-08-25 | 2016-11-16 | 江苏科技大学 | Recombinant alpha L rhamnoside enzyme extract is catalyzed the method for directionally hydrolyzing flavonoid glycoside in micro passage reaction |
| CN108467419A (en) * | 2018-03-23 | 2018-08-31 | 四川天添生物科技应用有限公司 | A method of synthesizing isoquercitrin with rutin |
| CN112111537A (en) * | 2020-09-15 | 2020-12-22 | 陕西嘉禾生物科技股份有限公司 | Semi-synthesis method of isoquercetin |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103627756A (en) * | 2013-11-26 | 2014-03-12 | 江苏科技大学 | Method for enzymatic synthesis of isoquercitrin by using continuous-flow tubular microreactor |
| CN103613623A (en) * | 2013-11-28 | 2014-03-05 | 江苏科技大学 | Application of multistage solvent extraction method in enzymatic synthesis of isoquercitrin |
| CN103613623B (en) * | 2013-11-28 | 2016-05-11 | 江苏科技大学 | The application of multiple-stage solvent extraction in the synthetic isoquercitrin of enzymatic |
| CN103667403A (en) * | 2013-12-17 | 2014-03-26 | 江苏科技大学 | Segmented flow microreaction technology for enzymatic synthesis of isoquercitrin in biphasic system |
| CN105969826A (en) * | 2016-06-17 | 2016-09-28 | 江苏科技大学 | Method for synthesizing isoquercitrin with nano-particle immobilized enzyme special for microreactor |
| CN106086123A (en) * | 2016-06-17 | 2016-11-09 | 江苏科技大学 | A kind of application ionic liquid improves the water miscible method of flavone compound |
| CN106086123B (en) * | 2016-06-17 | 2019-09-27 | 江苏科技大学 | A kind of application ionic liquid raising water-soluble method of flavone compound |
| CN105969826B (en) * | 2016-06-17 | 2019-09-27 | 江苏科技大学 | A kind of method of microreactor special-purpose nanometer particle immobilised enzymes synthesis isoquercitrin |
| CN106119319A (en) * | 2016-08-25 | 2016-11-16 | 江苏科技大学 | Recombinant alpha L rhamnoside enzyme extract is catalyzed the method for directionally hydrolyzing flavonoid glycoside in micro passage reaction |
| CN106119319B (en) * | 2016-08-25 | 2019-09-27 | 江苏科技大学 | Recombinate method of the alpha-L-Rhamnosidase crude extract for being catalyzed directionally hydrolyzing flavonoid glycoside in micro passage reaction |
| CN108467419A (en) * | 2018-03-23 | 2018-08-31 | 四川天添生物科技应用有限公司 | A method of synthesizing isoquercitrin with rutin |
| CN112111537A (en) * | 2020-09-15 | 2020-12-22 | 陕西嘉禾生物科技股份有限公司 | Semi-synthesis method of isoquercetin |
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