CN105669821B - Preparation method of glycyrrhetinic acid monoglucuronide - Google Patents
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Abstract
Belonging to the technical field of biochemical engineering, the invention discloses a preparation method of glycyrrhetinic acid monoglucuronide. The preparation method includes: taking licorice as the raw material, firstly preparing an extracted solution of glycyrrhetinic acid monoglucuronide, then performing clarification treatment, further conducting separation and purification, and finally drying the purified glycyrrhetinic acid monoglucuronide so as to obtain glycyrrhetinic acid monoglucuronide. The preparation method performs pretreatment on licorice through an external physical field, the process is scientific and reasonable, green and environmental protection, the operation is simple and practicable, and can realize continuous production. The glycyrrhetinic acid monoglucuronide prepared by the method has the characteristics of low cost, high production efficiency, high purity, easy popularization and high added value, can be used as a food additive and drug precursor, and provides raw material for the food and pharmaceutical industries.
Description
Technical field
The invention belongs to technical field of biochemical industry, and in particular to a kind of preparation side of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide
Method.
Background technology
Radix Glycyrrhizae (Glycyrrhizauralensis), another name Herba Hedyotis cantonensis root, Radix Glycyrrhizae, state old, Herba Hedyotis cantonensis, sweet root etc., are us
One of conventional Chinese herbal medicine of state's tradition, is that pulse family (Leguminosae) Glycyrrhiza (GlycyrrhizaLinn) perennial herb is planted
Thing.Radix Glycyrrhizae flat property and sweet taste, has functions that to invigorate the spleen and benefit qi, clearing heat and detoxicating, expelling phlegm and arresting coughing, relieving spasm to stop pain, coordinating the drug actions of a prescription, with pole
Wide clinical value.
Glycyrrhizic acid (GL) is the main active substances in Radix Glycyrrhizae, with certain pharmacologically active, such as protection liver, antiviral
With anticancer etc..Glycyrrhizic acid has higher sugariness, and its sugariness is 170-200 times of sucrose, is used as in food service industry sweet
Taste agent.Additionally, glycyrrhizic acid also serves as precursor compound, for the synthesis of other compounds.For example, glycyrrhizic acid removing grape alditol
Acid, generates enoxolone and Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, and reaction equation is shown in Fig. 1.
Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide (GAMG) has similar biology living as the derivative of glycyrrhizic acid to glycyrrhizic acid
Property, but its bioavilability is higher than glycyrrhizic acid.The sugariness of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide is 5 times of glycyrrhizic acid, and is had
The delayed characteristic of sweet sense, has humidification to fragrance, has masking effect to peculiar smell, is a kind of new natural sweetener.Therefore,
Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide is with a wide range of applications, it should it is developed and is utilized.
At present, mainly there are two methods, respectively chemical method using glycyrrhizic acid production Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide
And bioconversion method.Chinese patent (A of publication number CN 103788167) discloses a kind of high-purity list glucuronic acid Radix Glycyrrhizae
The preparation method of hypo acid.The method obtains thick Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide with licorice extract as raw material by acidolysis, and leads to
Cross semipreparative high performance liquid chromatography and be prepared and obtain high-purity GAMG.Although product purity prepared by the method is very high,
Industrialized production difficult to realize.It is single that Chinese patent (A of publication number CN 102367463) discloses a kind of indirect fed-batch fermentation production
The method of glucuronic acid enoxolone, the method can effectively improve GAMG fermentation yields, but the cycle of early stage induction producing enzyme compared with
It is long.Chinese patent (A of publication number CN 103509843) is disclosed with glycyrrhizic acid as substrate, with generation specific glucose aldehydic acid
The bacterial strain of glycosides enzyme is catalyst, with macroreticular resin as separating medium, removes product release substrate, realizes fermentation, feed supplement and product
Detached process.Although the method significantly improves substrate utilization ratio and efficiency of pcr product, complex operation, process is wayward.
In sum, chemical method conversion is by acid, alkali effect, the glucuronic acid of hydrolysis removing glycyrrhizic acid, so as to generate
Enoxolone and Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, but this method environmental pollution is more serious, and also strong acid and strong base is to Radix Glycyrrhizae
Sour structure can also produce certain destruction, so as to cause target product yield to decline.Biotransformation method, due to preparation condition
Complicated with technology, relatively costly, the cycle is long, it is more difficult to realize industrialization.
The content of the invention
The present invention is directed to the deficiencies in the prior art, there is provided a kind of preparation side of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide
Method.
To achieve these goals, the technical scheme that the present invention takes is as follows：
A kind of preparation method of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, comprises the following steps：
(1) preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract,
(2) clarifying treatment,
(3) separation, purification process,
(4) dried process,
Wherein, the concrete operations of step (1) are：Using steam blasting coupling microwaves assisted extraction method to the list in Radix Glycyrrhizae
Glucuronic acid enoxolone is extracted, and obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract.
A kind of concrete operations of the preparation method of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide are：
(1) preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract：Using steam blasting coupling microwaves assisted extraction method
Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide in Radix Glycyrrhizae is extracted, Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract is obtained；
(2) clarifying treatment：To the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract that obtains Jing after centrifugal treating, single grape is obtained
Uronic acid enoxolone clarified solution；
(3) separation, purification process：Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide is clarified using high speed adverse current chromatogram or macroreticular resin
Liquid is isolated and purified, and collection obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent；
(4) dried process：Place is dried to Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent using vacuum freeze-drying method
Reason, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide.
Steam blasting coupling microwaves assisted extraction concretely comprises the following steps described in step (1)：
(1) pretreatment of Radix Glycyrrhizae：Radix Glycyrrhizae is soaked using acid solution, the solid-to-liquid ratio of immersion is 1:1-3:1, immersion temperature
Spend for 50 DEG C -70 DEG C, soak time is 3-5h；
(2) steam blasting：Steam explosion treatment is carried out to the Radix Glycyrrhizae after immersion, steam blasting condition is：Pressure is 6-
10MPa, blasting time is 5-15min；
(3) microwave radiation exaraction：Microwave radiation exaraction is carried out to the Radix Glycyrrhizae after steam blasting, liquid-solid ratio during extraction is
30:1-50:1, extraction time is 10-60min, and Extracting temperature is 60-70 DEG C, and microwave power is 300W-600W, and speed of agitator is
100-250rpm。
Step (1) acid solution is acetic acid, nitric acid or sulfuric acid, and the concentration of the acid solution is 3-8%.
The condition of centrifugation is described in step (2)：Rotating speed is 3600-4200rpm/min, and centrifugation time is 5-15min.
The solvent system that step (3) high speed adverse current chromatogram is isolated and purified is：N-hexane:Methyl alcohol:Ethyl acetate:Water=
0.5:3:3:5 or 0:2:3:5；
The type of elution that step (3) high speed adverse current chromatogram is isolated and purified is：First done and flowed with fix phase, lower phase of phase
Dynamic phase, reversal connection reversion, rotating speed is 600-800r/min, and flow velocity is 1-2mL/min, elutes 4-6h；Then mobile phase is changed to
Phase, while being changed into just connect rotating forward, rotating speed is 600-800r/min, and flow velocity is 1-2mL/min, elutes 3-5h；
Or mobile phase is done using fix phase, upper phase of lower phase, and rotating forward is just being connect, rotating speed is 600-800r/min, and flow velocity is 1-
2mL/min, elutes 8-10h.
Macroreticular resin described in step (3) is EXA50, EXA45, SP825 or SP207；
The condition that step (3) macroreticular resin is isolated and purified is：Resin content is 17-42mg/mL, and adsorption time is
5-10h, then using the aqueous solution and 30%-90% ethanol of pH8-12 carries out separation parsing successively.
Drying time described in step (4) is 24-36h.
Beneficial effects of the present invention are：The method is pre-processed by additional physical field to Radix Glycyrrhizae, craft science rationally,
Environmental protection, operation is simple, can realize continuous prodution；The Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide prepared using the method
Low cost, production efficiency is high, and purity is high, it is easy to promote, with compared with high added value, can serve as food additives and prodrug
Material, for food and medicine industry raw material is provided.
Description of the drawings
Fig. 1 is Radix Glycyrrhizae acid hydrolytic reaction approach figure.
Fig. 2 for Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide standard items liquid phase spectrogram (on) with the preparation method prepare after purification
Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide liquid phase spectrogram (under).
Specific embodiment
With reference to the accompanying drawings and examples the present invention will be further described, and below example facilitates a better understanding of this
Invention, but do not limit the present invention.Experimental technique in following embodiments, if no special instructions, is conventional method；Used
Material, reagent etc., if no special instructions, commercially obtain.Embodiment 1：
1. the preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract：Radix Glycyrrhizae is soaked initially with 5% acetic acid solution,
Liquid-solid ratio is 3:1, soaking temperature is 60 DEG C, and soak time is 4h；Radix Glycyrrhizae after immersion is drained away the water, steam explosion process is carried out,
Pressure is 10MPa, and blasting time is 10min；After steam explosion pretreatment terminates, microwave radiation exaraction is carried out to Radix Glycyrrhizae, extract is solid
Than 30:1, extraction time is 30min, and temperature is 60 DEG C, and microwave power is 300W, and speed of agitator is 150rpm, and extraction terminates
To Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract.
2. clarifying treatment：The Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract for obtaining is carried out into centrifugal treating, centrifugal rotational speed
4200rpm/min, centrifugation time is 15min, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clarified solution, and precipitation is discarded.
3. separate, purification process：Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clarified solution is separated using high speed adverse current chromatogram
Purifying, solvent system used is n-hexane:Methyl alcohol:Ethyl acetate:Water=0:2:3:5；Type of elution is first to be consolidated with phase
Determine phase, lower phase and do mobile phase, reversal connection is inverted, and rotating speed is 700r/min, and flow velocity is 2mL/min, and elution time is 6h, then will stream
Dynamic phase is changed to phase, while being changed into just connect rotating forward, rotating speed is 600r/min, and flow velocity is 1.5mL/min, and elution time is 3h,
Collection obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent.
4. dried process：Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent to obtaining is carried out using vacuum freeze drying mode
It is dried, drying time is 36h, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide prepared by this condition
Conversion ratio is 23.12%, purity 62.12%, Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide liquid phase spectrogram after purification and single grape alditol
The liquid phase spectrogram of sour enoxolone standard items is as shown in Figure 2.
Embodiment 2：
1. the preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract：Radix Glycyrrhizae is soaked initially with 5% sulfuric acid solution,
Liquid-solid ratio is 3:1, soaking temperature is 60 DEG C, and soak time is 4h；Radix Glycyrrhizae after immersion is drained away the water, steam explosion process is carried out,
Pressure is 10MPa, and blasting time is 10min；After steam explosion pretreatment terminates, microwave radiation exaraction is carried out to Radix Glycyrrhizae, extract is solid
Than 30:1, extraction time is 30min, and temperature is 60 DEG C, and microwave power is 300W, and speed of agitator is 150rpm, and extraction terminates
To Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract.
2. clarifying treatment：The Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract for obtaining is carried out into centrifugal treating, centrifugal rotational speed
4200rpm/min, centrifugation time is 15min, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clarified solution, and precipitation is discarded.
3. separate, purification process：Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clarified solution I is separated using high speed adverse current chromatogram
Purifying, solvent system used is n-hexane:Methyl alcohol:Ethyl acetate:Water=0.5:3:3:5；Type of elution fixes for lower phase
Phase, upper phase do mobile phase, are just connecing rotating forward, and rotating speed is 700r/min, and flow velocity is 2mL/min, and elution time is 10h, and collection is obtained
Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent.
4. dried process：Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent to obtaining is carried out using vacuum freeze drying mode
It is dried, drying time is 36h, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide prepared by this condition
Conversion ratio is 21.75%, and purity is 60.82%.
Embodiment 3：
1. the preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract：Radix Glycyrrhizae is soaked initially with 5% sulfuric acid, liquid is solid
Than for 2:1, soaking temperature is 70 DEG C, and soak time is 3h；Radix Glycyrrhizae after immersion is drained away the water, steam explosion process, pressure is carried out
For 10MPa, blasting time is 15min；After steam explosion pretreatment terminates, microwave radiation exaraction is carried out to Radix Glycyrrhizae, extract liquid-solid ratio 50:
1, extraction time is 60min, and temperature is 70 DEG C, and microwave power is 600W, and speed of agitator is 250rpm, extracts end and obtains single Portugal
Grape uronic acid enoxolone extract.
2. clarifying treatment：The Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract for obtaining is carried out into centrifugal treating, centrifugal rotational speed
3600rpm/min, centrifugation time is 15min, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clarified solution, and precipitation is discarded.
3. separate, purification process：Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clarified solution is isolated and purified using macroreticular resin,
From macroreticular resin be EXA45, resin content is 42mg/mL, adsorption time 7h, from pH is successively then 12 water-soluble
Liquid, 90% ethanol carries out separation parsing, and collection obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent.
4. dried process：Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent to obtaining is carried out using vacuum freeze drying mode
It is dried, drying time is 36h, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide prepared by this condition
Conversion ratio is 19.12%, purity 58.78%.
Embodiment 4：
1. the preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract：Radix Glycyrrhizae is soaked initially with 5% salpeter solution,
Liquid-solid ratio is 2:1, soaking temperature is 50 DEG C, and soak time is 3h；Radix Glycyrrhizae after immersion is drained away the water, steam explosion process is carried out,
Pressure is 8MPa, and blasting time is 15min；After steam explosion pretreatment terminates, microwave radiation exaraction is carried out to Radix Glycyrrhizae, extract liquid-solid ratio
30:1, extraction time is 60min, and temperature is 60 DEG C, and microwave power is 300W, and speed of agitator is 200rpm, extracts end and obtains
Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract.
2. clarifying treatment：The Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract for obtaining is carried out into centrifugal treating, centrifugal rotational speed
4200rpm/min, centrifugation time is 10min, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clarified solution, and precipitation is discarded.
3. separate, purification process：Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clarified solution is isolated and purified using macroreticular resin,
From macroreticular resin be EXA50, resin content is 17mg/mL, adsorption time 5h, from pH is successively then 11 water-soluble
Liquid, 70% ethanol carries out separation parsing, and collection obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent.
4. dried process：Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent to obtaining is carried out using vacuum freeze drying mode
It is dried, drying time is 36h, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide prepared by this condition
Conversion ratio is 18.72%, purity 51.78%.
Claims (9)
1. a kind of preparation method of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, comprises the following steps：
(1) preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract,
(2) clarifying treatment,
(3) separation, purification process,
(4) dried process,
Characterized in that, the concrete operations of step (1) are：
1) pretreatment of Radix Glycyrrhizae：Radix Glycyrrhizae is soaked using acid solution, the solid-to-liquid ratio of immersion is 1:1-3:1, soaking temperature is
50 DEG C -70 DEG C, soak time is 3-5h；
2) steam blasting：Steam explosion treatment is carried out to the Radix Glycyrrhizae after immersion, steam blasting condition is：Pressure is 6-10MPa, quick-fried
The broken time is 5-15min；
3) microwave radiation exaraction：Microwave radiation exaraction is carried out to the Radix Glycyrrhizae after steam blasting, liquid-solid ratio during extraction is 30:1-
50:1, extraction time is 10-60min, and Extracting temperature is 60-70 DEG C, and microwave power is 300W-600W, and speed of agitator is 100-
250rpm, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract；
The concrete operations of step (3) are：Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide is clarified using high speed adverse current chromatogram or macroreticular resin
Liquid is isolated and purified, and collection obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent.
2. a kind of preparation method of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 1, it is characterised in that step
And (4) concrete operations are (2)：
(2) clarifying treatment：To the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extract that obtains Jing after centrifugal treating, single grape alditol is obtained
Sour enoxolone clarified solution；
(4) dried process：Process is dried to Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent using vacuum freeze-drying method, is obtained
To Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide.
3. the preparation method of a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 1, it is characterised in that step 1)
The acid solution is acetic acid, nitric acid or sulfuric acid, and the concentration of the acid solution is 3-8%.
4. a kind of preparation method of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 2, it is characterised in that step
(2) condition of centrifugation is described in：Rotating speed is 3600-4200rpm/min, and centrifugation time is 5-15min.
5. a kind of preparation method of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 1, it is characterised in that step
(3) solvent system that the high speed adverse current chromatogram is isolated and purified is：N-hexane:Methyl alcohol:Ethyl acetate:Water=0.5:3:3:5 or
0:2:3:5。
6. a kind of preparation method of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 1, it is characterised in that step
(3) type of elution that the high speed adverse current chromatogram is isolated and purified is：First mobile phase is done with fix phase, lower phase of phase, reversal connection is anti-
Turn, rotating speed is 600-800r/min, and flow velocity is 1-2mL/min, elute 4-6h；Then mobile phase is changed to into upper phase, while transformation
Just to connect rotating forward, rotating speed is 600-800r/min, and flow velocity is 1-2mL/min, elutes 3-5h；
Or mobile phase is done using fix phase, upper phase of lower phase, and rotating forward is just being connect, rotating speed is 600-800r/min, and flow velocity is 1-2mL/
Min, elutes 8-10h.
7. a kind of preparation method of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 1, it is characterised in that step
(3) macroreticular resin described in is EXA50, EXA45, SP825 or SP207.
8. a kind of preparation method of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 1, it is characterised in that step
(3) condition that the macroreticular resin is isolated and purified is：Resin content is 17-42mg/mL, and adsorption time is 5-10h, Ran Houyi
The aqueous solution and 30%-90% ethanol of secondary employing pH8-12 carries out separation parsing.
9. a kind of preparation method of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 2, it is characterised in that step
(4) drying time described in is 24-36h.
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| CN106591071A (en) * | 2016-12-23 | 2017-04-26 | 江苏耐雀生物工程技术有限公司 | Healthcare baijiu and preparation method thereof |
| CN106636290B (en) * | 2017-02-03 | 2020-06-09 | 江南大学 | Method for producing glycyrrhetinic acid monoglucuronide through fermentation and application |
| CN108640963A (en) * | 2018-06-01 | 2018-10-12 | 天津科技大学 | A kind of method of steam explosion thermochemical method conversion glycyrrhizic acid |
| CN113295798A (en) * | 2021-05-28 | 2021-08-24 | 浙江树人学院（浙江树人大学） | Sample chromatographic analysis method based on measurement of sample component retention time |
| CN113913489A (en) * | 2021-11-24 | 2022-01-11 | 洛阳蓝斯利科技有限公司 | Preparation method of monoglucuronic acid 24-hydroxy-glycyrrhetinic acid |
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