CN106086123B - A kind of application ionic liquid raising water-soluble method of flavone compound - Google Patents
A kind of application ionic liquid raising water-soluble method of flavone compound Download PDFInfo
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Abstract
A kind of application ionic liquid raising water-soluble method of flavone compound, belongs to food additives biological processing field.By the way that a certain proportion of [Bmim] [BF is added into flavone compound aqueous solution4] ionic liquid, and it is greatly improved so as to heating water bath or ultrasonic wave added means the water solubility of flavone compound.This method is easy to operate, mild condition, improves production efficiency of the flavone compound as reaction substrate when, increases productivity, increase the operation strategies of flavone compound.
Description
Technical field
The invention belongs to food additives biological processing fields, and in particular to a kind of application ionic liquid raising flavonoids
Close the water-soluble method of object.
Background technique
The prior art: flavone compound (Flavonoids) is that one kind is present in nature, has 2- phenyl chromogen
The compound of ketone (Flavone) structure.There is a ketone carbonyl group in their molecules, oxygen atom on first has alkalinity, can be with
Strong acid is at salt, and hydroxy derivatives have a yellow more, therefore also known as flavone or flavones.The main representative substance of flavone compound is
Rutin (Rutin), scutellarin (Baicalein) etc., wherein rutin is the precursor substance of a variety of rare natural products, such as different Mongolian oak
Skin glycosides, Quercetin etc..Isoquercitrin (Isoquercitrin) is very rare in a kind of nature but has significant anti-oxidant
The flavonoids effective constituent of the bioactivity such as property, antitumor, and new type functional food additive EMIQ in the world in recent years
Synthesis material (Toxicology, 2010,268 (3): 213- of (Enzymatically modified isoquercitrin)
218), nature content is extremely low, the selective hydrolysis for the rutin that needs to rely on.The solubility of rutin in aqueous solution is bigger, water
The yield that isoquercitrin is obtained after solution reaction is higher.The water-soluble for how improving flavone compound is studied thus with important
Meaning.
104059045 A of patent CN has invented a kind of water solubility α-naphthalene yellow acetol derivative and preparation method thereof, mainly adopts
The aminocarboxylic acid ester that fatty alcohol is replaced with hydrogen and halogen improves prepared α-naphthalene yellow acetol derivative water solubility, makes it
The prevention of human malignant tumor can be preferably used for.A kind of other days of preciousness of flavone compound derivative such as isoquercitrin-
Right product needs to be made using Flavonoid substances rutin, but rutin is due to having hydroxyl in structure, so that its water-soluble pole
It is low, it is less or be substantially insoluble in water.Rutin can be properly increased by using Glycine-NaOH buffer solution (pH 9.0)
Solubility in the solution, highest rutin solution concentration reach 0.78g/L, improve compared to solubility 0.08g/L in pure water
Nearly 10 times (Bioresource Technology, 2013,128:156-163).It is subsequent to continue to solution ratio before the reaction
It optimizes, after the solution temperature time is adjusted, rutin solubility is greatly increased, and can reach 2g/L, substantially increases production
The yield of object isoquercitrin reduces costs (Scientific Reports, 2015,5:8682).But with new function
The increase of property food additives EMIQ (Enzymatically modified isoquercitrin) demand, i.e. isoquercitrin
The rapidly increase of demand, this requires the efficiency of synthesis isoquercitrin and yield to greatly increase, to meet the market demand；
Seek thus improve reaction substrate rutin solubility be to solve the problems, such as a kind of this cheapest method, with this derive to how
The water-soluble critical issue of flavone compound is greatly improved, that widens chromocor compound uses field.
Ionic liquid (or ionic liquid) refers to the liquid being composed entirely of ions.Largely research shows that ionic liquid
Body has the advantages that ionic liquid is tasteless, non-ignitable, and vapour pressure is extremely low, therefore can be used in high vacuum system, while can subtract
Few problem of environmental pollution generated by volatilization；Ionic liquid can be such that reaction carries out under homogeneous phase condition, while can reduce equipment
Volume；Can operating temperature range it is wide (- 40~300 DEG C), there is good thermal stability and chemical stability, easily and other materials
Separation, can recycle；It can express the acidity of Lewis, Franklin acid, and acid strength is adjustable.Patent CN
101933104 A report a kind of side that liquid-liquid extraction, liquid-solid extraction or liquid-gas extraction are carried out using magnetic ionic liquids
Method, to the separation of extract based on the interaction between spe medium and magnetic field.103896844 A of patent CN discloses one
Class biocompatible ions liquid and its preparation method and application.Such ionic liquid may be used as the medium of biocatalytic reaction.
Lipase is dissolved in such biological ion liquid [CmOHMIM] [CnOHSO3] after show quite high catalytic activity, illustrate this from
Sub- liquid has preferable biocompatibility, can be applied to biological chemical field and Western medicine preparation technical field.Ionic liquid is made
It is a kind of suitable media applications in enzymatic reaction, compared with traditional organic solvent medium, ionic liquid can not only lead to
Cross the mass transfer for influencing reaction system and thermodynamics of reactions balance, moreover it is possible to entire to influence by the stability and the selectivity that influence enzyme
Reaction process.During reaction, the technologies such as ionic liquid and microwave, ultrasound, which combine, can be improved reaction rate, improve
Reaction efficiency.Beta galactosidase is catalyzed in the reaction of N-Acetyl-D-glucosamine production lactose, due to product N- acetyl lactosamine
Competitive second level hydrolysis be suppressed yield.This reaction is in [MMIm] [MeSO4When being carried out in]/water (V/V 25:75), produce
For rate up to 58%, and when carrying out in water-buffer solution system, yield is only 30% (Biotechnology and
Bioengineering,2006,95(6):1093-1100).Thus provable ionic liquid is played in whole system to Guan Chong
The effect wanted.
The preparation of new type functional food additive EMIQ (Enzymatically modified isoquercitrin)
A large amount of substrate rutin is needed to prepare, and solubility is extremely low in water for the preferable rutin of alcohol-soluble, enzymatic catalysis synthesis needs again
The vigor to guarantee enzyme is carried out in aqueous solution, thus needs to find a kind of raising rutin water solubility, i.e. flavone compound
The method of solubility.And ionic liquid 1- butyl -3- methyl-imidazoles tetrafluoroborate ([Bmim] [BF4]), it can it increases greatly
Add its solubility in water, for a large amount of lifes for treasuring natural products isoquercitrin (or new type functional food additive EMIQ)
Object, which catalyzes and synthesizes, provides solid theoretical method.
Summary of the invention
The technical issues of solution: being directed to deficiency described in the prior art, applies ionic liquid the present invention provides a kind of
Improve the water-soluble method of flavone compound, to improve the water solubility of chromocor compound in water, expand its application range and
Field.
Technical solution: a kind of application ionic liquid raising water-soluble method of flavone compound, the ionic liquid of selection
For [Bmim] [BF4]。
Above-mentioned selected flavone compound is rutin, and the method dissolved by heating can shake heating for water-bath, surpass
Sound heating water bath or microwave radiation heating, used heating temperature are 15~50 DEG C.
The solution for dissolving flavone compound is Glycine-NaOH buffer, and pH range is 8~10.
Above-mentioned ionic liquid and the volume mass of rutin ratio (μ L:mg) range are 1:10~1:50, dissolution time needs 1~
10min。
The utility model has the advantages that ionic liquid is added when dissolving rutin can be big during using rutin enzyme' s catalysis isoquercitrin
It is big to shorten dissolution time, the solubility of rutin is improved, to improve the yield of isoquercitrin.Derived with this to flavonoid
Object improves the operation strategies after water solubility.This method dissolves flavone compound mild condition, environmentally friendly and survivable
The bioactivity of flavone compound, is easy to industrial applications.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
The measuring method that detection rutin is used in the embodiment of the present invention is high performance liquid chromatography, chromatographic condition: Alltima
C18(250mm × 4.6mm, 5 μm), mobile phase: 0.02% phosphoric acid-acetonitrile (80:20, v/v)；Detection wavelength: 360nm；Flow velocity:
1.0mL/min；Sample volume: 20 μ L.
Wherein, the calculation method of rutin solubility are as follows:
Embodiment 1
Prepare the rutin solution of 0.1,0.2,0.5,1.0,2.0,3.0,4.0,5.0g/L respectively with the buffer of pH 8.0,
It is divided into experimental group 1,2,3 ... and control group 1,2,3 ..., experimental group is according to ionic liquid and the volume mass of rutin ratio (μ L:mg)
Be set as 1:10, also 8.0 buffer of pH is added according to the volume mass of rutin ratio (μ L:mg) 1:10 in control group, by experimental group and
Control group is put into 15 DEG C of ultrasonic water baths simultaneously after heating for dissolving 1min, takes out each experimental group and control sample, process is subsequent
HPLC detects the content of rutin in each solution after processing, it is found that the solubility of experimental group all higher than control group, and calculates hair
The solubility of existing rutin solution can reach 2.804g/L.It the results are shown in Table one.
One HPLC test experience group of table and control group rutin solution concentration
Embodiment 2
Prepare 0.1 respectively with the buffer of pH 10.0,0.2,0.5,1.0,2.0,3.0,4.0, the rutin of 5.0g/L it is molten
Liquid, is divided into experimental group 1,2,3 ... and control group 1,2,3 ..., experimental group according to ionic liquid and the volume mass of rutin ratio (μ L:
Mg it) is set as 1:50, control group is also added 10.0 buffer of pH according to the volume mass of rutin ratio (μ L:mg) 1:50, will test
Group and control group are put into 50 DEG C of ultrasonic water baths simultaneously after heating for dissolving 10min, are taken out each experimental group and control sample, are passed through
The content for detecting rutin in each solution after processing with HPLC, find the solubility of experimental group all higher than control group, preparation
The rutin of 3.0g/L is all dissolved, and the solubility for calculating discovery rutin solution can reach 3.6g/L, and experimental result is shown in Table two.
Two HPLC test experience group of table and control group rutin solution concentration
Embodiment 3
Prepare the rutin solution of 0.1,0.2,0.5,1.0,2.0,3.0,4.0,5.0g/L respectively with the buffer of pH 9.0,
It is divided into experimental group 1,2,3 ... and control group 1,2,3 ..., experimental group is according to ionic liquid and the volume mass of rutin ratio (μ L:mg)
Be set as 1:25, also 9.0 buffer of pH is added according to the volume mass of rutin ratio (μ L:mg) 1:25 in control group, by experimental group and
Control group is put into 50 DEG C of ultrasonic water baths simultaneously after heating for dissolving 5min, each experimental group and control sample is taken out, by processing
HPLC detects the content of rutin in each solution afterwards, find the solubility of experimental group all higher than control group, the 4.0g/L's of preparation
Rutin is all dissolved, and the solubility for calculating discovery rutin solution can reach 4.2g/L, and experimental result is shown in Table three.
Three HPLC test experience group of table and control group rutin solution concentration
Claims (1)
1. a kind of application ionic liquid improves the water-soluble method of flavone compound, it is characterised in that ionic liquid [Bmim]
[BF4] with the volume mass ratio of rutin (μL:mg it) is set as 1:25, dissolves by heating 5min in 50 DEG C of ultrasonic water baths.
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Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108236678B (en) * | 2017-11-30 | 2020-12-08 | 浙江科技学院 | Method for extracting and preparing bamboo leaf flavone by using ionic liquid |
| CN108079048A (en) * | 2017-12-29 | 2018-05-29 | 广西汇智生产力促进中心有限公司 | The method that general flavone is extracted in Canton love-pea vine |
| 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 |
| CN110818667A (en) * | 2019-10-22 | 2020-02-21 | 西安医学院 | Method for extracting flavone from pomegranate waste based on ionic liquid and semi-bionic enzymatic method |
| CN113101371A (en) * | 2021-04-07 | 2021-07-13 | 中国科学院大学温州研究院(温州生物材料与工程研究所) | Solubilization method of hydrophobic drug based on cation-pi effect |
| CN116422002B (en) * | 2023-01-13 | 2023-10-20 | 完美（广东）日用品有限公司 | Aloe extract and preparation method and application thereof |
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| CN102876746A (en) * | 2012-10-11 | 2013-01-16 | 江苏科技大学 | Method of ionic liquid cosolvent effect reinforced enzymatic synthesis of isoquercitrin |
| 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 |
| CN104450833A (en) * | 2014-11-19 | 2015-03-25 | 江苏大学 | Low-temperature microwave field intensified enzymatic synthesis method for isoquercitrin |
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| CN102876746A (en) * | 2012-10-11 | 2013-01-16 | 江苏科技大学 | Method of ionic liquid cosolvent effect reinforced enzymatic synthesis of isoquercitrin |
| 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 |
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