CN105669821A - Preparation method of glycyrrhetinic acid monoglucuronide - Google Patents
Preparation method of glycyrrhetinic acid monoglucuronide Download PDFInfo
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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, the preparation method being specifically related to a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide.
Background technology
Radix Glycyrrhizae (Glycyrrhizauralensis), another name Herba Hedyotis cantonensis root, Radix Glycyrrhizae, state are old, Herba Hedyotis cantonensis, sweet root etc., it is one of conventional Chinese herbal medicine of China's tradition, for pulse family (Leguminosae) Glycyrrhiza (GlycyrrhizaLinn) herbaceos perennial. The flat sweet in the mouth of Radix Glycyrrhizae property, has effect of invigorating the spleen and replenishing QI, heat-clearing and toxic substances removing, expelling phlegm for arresting cough, relieving spasm to stop pain, coordinating the actions of various ingredients in a prescription, has extremely wide clinical value.
Glycyrrhizic acid (GL) is the main active substances in Radix Glycyrrhizae, has certain pharmacologically active, such as the liver protecting, antiviral and anticancer etc. Glycyrrhizic acid has higher sugariness, and its sugariness is 170-200 times of sucrose, is used as sweeting agent in food service industry. Additionally, glycyrrhizic acid also serves as precursor compound, for the synthesis of other compounds. Such as, glycyrrhizic acid elimination glucuronic acid, generate enoxolone and Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, reaction equation is shown in Fig. 1.
Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide (GAMG), as the derivant of glycyrrhizic acid, has similar biological activity, but its bioavailability is higher than glycyrrhizic acid to glycyrrhizic acid. The sugariness of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide is 5 times of glycyrrhizic acid, and has the characteristic that sweet sense is delayed, fragrance is had potentiation, abnormal flavour is had masking effect, is a kind of novel natural sweetener. Therefore, Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide is with a wide range of applications, it should it is developed and utilizes.
At present, utilizing glycyrrhizic acid to produce Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide mainly has two kinds of methods, respectively chemical method and bioconversion method. The preparation method that Chinese patent (publication number CN103788167A) discloses a kind of high-purity Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide. This method, with Radix Glycyrrhizae extract for raw material, obtains thick Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide by acidolysis, and is prepared by semipreparative high performance liquid chromatography and obtains high-purity GAMG. Although product purity prepared by the method is significantly high, but is difficulty with industrialized production. Chinese patent (publication number CN102367463A) discloses a kind of method that indirect fed-batch fermentation produces Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, and this method can be effectively improved GAMG fermentation yield, but the cycle that enzyme is produced in early stage induction is longer.Chinese patent (publication number CN103509843A) discloses with glycyrrhizic acid for substrate, it is catalyst with the bacterial strain of generation specific glucose aldehyde neuraminidase, with macroporous resin for separating medium, remove product release substrate, it is achieved the process that fermentation, feed supplement separate with product. Although the method significantly improves substrate utilization ratio and efficiency of pcr product, but complicated operation, process is wayward.
In sum, chemical method converts by acid, alkali effect, the glucuronic acid of hydrolysis elimination glycyrrhizic acid, thus generating enoxolone and Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, but this method environmental pollution is comparatively serious, and glycyrrhizic acid structure also can be produced certain destruction by strong acid and strong base, thus causing that target product yield declines. Biotransformation method, owing to preparation condition and Technology are complicated, relatively costly, the cycle is long, it is more difficult to realize industrialization.
Summary of the invention
The present invention is directed to the deficiencies in the prior art, it is provided that the preparation method of a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide.
To achieve these goals, the technical scheme that the present invention takes is as follows:
The preparation method of a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, comprises the following steps:
(1) preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution,
(2) clarifying treatment,
(3) separation, purification process,
(4) dried,
Wherein, the concrete operations of step (1) are: adopt steam explosion coupling microwaves assisted extraction method that the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide in Radix Glycyrrhizae is extracted, obtain Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution.
The concrete operations of the preparation method of described a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide are:
(1) preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution: adopt steam explosion coupling microwaves assisted extraction method that the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide in Radix Glycyrrhizae is extracted, obtain Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution;
(2) clarifying treatment: after the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution obtained is processed by centrifugation, obtain Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor;
(3) separation, purification process: utilize high speed adverse current chromatogram or macroporous resin that Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor is easily separated purification, collect and obtain Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent;
(4) dried: adopt vacuum freeze-drying method that Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent is dried process, obtain Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide.
Concretely comprising the following steps of steam explosion coupling microwaves assisted extraction described in step (1):
(1) pretreatment of Radix Glycyrrhizae: adopting acid solution that Radix Glycyrrhizae is soaked, the solid-to-liquid ratio of immersion is 1:1-3:1, and soaking temperature is 50 DEG C-70 DEG C, and soak time is 3-5h;
(2) steam explosion: the Radix Glycyrrhizae after soaking is carried out Steam explosion treatment, and steam explosion condition is: pressure is 6-10MPa, and blasting time is 5-15min;
(3) microwave radiation exaraction: the Radix Glycyrrhizae after steam explosion is carried out microwave radiation exaraction, liquid-solid ratio during extraction is 30:1-50:1, and extraction time is 10-60min, and Extracting temperature is 60-70 DEG C, microwave power is 300W-600W, and speed of agitator is 100-250rpm.
Step (1) described acid solution is acetic acid, nitric acid or sulphuric acid, and the concentration of described acid solution is 3-8%.
Condition centrifugal described in step (2) is: rotating speed is 3600-4200rpm/min, and centrifugation time is 5-15min.
The solvent system of the described high speed adverse current chromatogram separation purification of step (3) is: normal hexane: methanol: ethyl acetate: water=0.5:3:3:5 or 0:2:3:5;
The type of elution of step (3) described high speed adverse current chromatogram separation purification is: first doing mobile phase by fix phase, lower phase of phase, reversal connection is reversed, and rotating speed is 600-800r/min, and flow velocity is 1-2mL/min, eluting 4-6h; Then mobile phase being changed to upper phase, is changed to positive simultaneously and connects rotating forward, rotating speed is 600-800r/min, and flow velocity is 1-2mL/min, eluting 3-5h;
Or fix mutually under adopting phase, upper phase do mobile phase, just connecing rotating forward, rotating speed is 600-800r/min, and flow velocity is 1-2mL/min, eluting 8-10h.
Macroporous resin described in step (3) is EXA50, EXA45, SP825 or SP207;
The condition of the described macroporous resin separation purification of step (3) is: resin content is 17-42mg/mL, and adsorption time is 5-10h, then adopts the aqueous solution of pH8-12 and 30%-90% ethanol to be easily separated parsing successively.
Drying time described in step (4) is 24-36h.
The invention have the benefit that Radix Glycyrrhizae is carried out pretreatment by additional physical field by the method, craft science is reasonable, environmental protection, and operation is simple, it is possible to realizes continuous prodution; Adopting Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide cost prepared by the method low, production efficiency is high, and purity is high, it is easy to promotes, has relatively high added value, it is possible to as food additive and prodrug material, provides raw material for food and medicine industry.
Accompanying drawing explanation
Fig. 1 is glycyrrhizic acid hydrolysis approach figure.
Fig. 2 be Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide standard substance liquid phase spectrogram (on) with described preparation method prepare the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide after purification liquid phase spectrogram (under).
Detailed description of the invention
Below in conjunction with drawings and Examples, the present invention will be further described, and below example is easy to be more fully understood that the present invention, but does not limit the present invention. Experimental technique in following embodiment, if no special instructions, is conventional method; Used material, reagent etc., if no special instructions, all commercially obtain. Embodiment 1:
1. the preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution: Radix Glycyrrhizae is soaked initially with 5% acetic acid solution, liquid-solid ratio is 3:1, and soaking temperature is 60 DEG C, and soak time is 4h; Being drained away the water by Radix Glycyrrhizae after soaking, carry out steam explosion process, pressure is 10MPa, and blasting time is 10min; After steam explosion pretreatment terminates, Radix Glycyrrhizae carrying out microwave radiation exaraction, extract liquid-solid ratio 30:1, extraction time is 30min, and temperature is 60 DEG C, and microwave power is 300W, and speed of agitator is 150rpm, extracts end and obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution.
2. clarifying treatment: being centrifuged the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution obtained processing, centrifugal rotational speed 4200rpm/min, centrifugation time is 15min, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor, and precipitation discards.
3. separation, purification process: utilizing high speed adverse current chromatogram that Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor is easily separated purification, solvent system used is normal hexane: methanol: ethyl acetate: water=0:2:3:5; Type of elution is for first doing mobile phase by fix phase, lower phase of phase, reversal connection is reversed, rotating speed is 700r/min, and flow velocity is 2mL/min, and elution time is 6h, then mobile phase is changed to upper phase, being changed to positive simultaneously and connect rotating forward, rotating speed is 600r/min, and flow velocity is 1.5mL/min, elution time is 3h, collects and obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent.
4. dried: adopt vacuum lyophilization mode to be dried the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent obtained, drying time is 36h, obtain Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide conversion ratio prepared by this condition is 23.12%, the liquid phase spectrogram of purity 62.12%, the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide liquid phase spectrogram after purification and Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide standard substance is as shown in Figure 2.
Embodiment 2:
1. the preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution: Radix Glycyrrhizae is soaked initially with 5% sulfuric acid solution, liquid-solid ratio is 3:1, and soaking temperature is 60 DEG C, and soak time is 4h; Being drained away the water by Radix Glycyrrhizae after soaking, carry out steam explosion process, pressure is 10MPa, and blasting time is 10min; After steam explosion pretreatment terminates, Radix Glycyrrhizae carrying out microwave radiation exaraction, extract liquid-solid ratio 30:1, extraction time is 30min, and temperature is 60 DEG C, and microwave power is 300W, and speed of agitator is 150rpm, extracts end and obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution.
2. clarifying treatment: being centrifuged the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution obtained processing, centrifugal rotational speed 4200rpm/min, centrifugation time is 15min, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor, and precipitation discards.
3. separation, purification process: utilizing high speed adverse current chromatogram that Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor I is easily separated purification, solvent system used is normal hexane: methanol: ethyl acetate: water=0.5:3:3:5; Type of elution is that fix phase, upper phase of lower phase does mobile phase, is just connecing rotating forward, and rotating speed is 700r/min, and flow velocity is 2mL/min, and elution time is 10h, collects and obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent.
4. dried: adopt vacuum lyophilization mode to be dried the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent obtained, drying time is 36h, obtaining Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide conversion ratio prepared by this condition is 21.75%, and purity is 60.82%.
Embodiment 3:
1. the preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution: Radix Glycyrrhizae is soaked initially with 5% sulphuric acid, liquid-solid ratio is 2:1, and soaking temperature is 70 DEG C, and soak time is 3h; Being drained away the water by Radix Glycyrrhizae after soaking, carry out steam explosion process, pressure is 10MPa, and blasting time is 15min; After steam explosion pretreatment terminates, Radix Glycyrrhizae carrying out microwave radiation exaraction, 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 Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution.
2. clarifying treatment: being centrifuged the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution obtained processing, centrifugal rotational speed 3600rpm/min, centrifugation time is 15min, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor, and precipitation discards.
3. separation, purification process: adopt macroporous resin that Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor is easily separated purification, the macroporous resin selected is EXA45, resin content is 42mg/mL, adsorption time 7h, then selecting pH successively is 12 aqueous solutions, 90% ethanol is easily separated parsing, collects and obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent.
4. dried: adopt vacuum lyophilization mode to be dried the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent obtained, drying time is 36h, obtaining Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide conversion ratio prepared by this condition is 19.12%, purity 58.78%.
Embodiment 4:
1. the preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution: Radix Glycyrrhizae is soaked initially with 5% salpeter solution, liquid-solid ratio is 2:1, and soaking temperature is 50 DEG C, and soak time is 3h; Being drained away the water by Radix Glycyrrhizae after soaking, carry out steam explosion process, pressure is 8MPa, and blasting time is 15min;After steam explosion pretreatment terminates, Radix Glycyrrhizae carrying out microwave radiation exaraction, 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 extracting solution.
2. clarifying treatment: being centrifuged the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution obtained processing, centrifugal rotational speed 4200rpm/min, centrifugation time is 10min, obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor, and precipitation discards.
3. separation, purification process: adopt macroporous resin that Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor is easily separated purification, the macroporous resin selected is EXA50, resin content is 17mg/mL, adsorption time 5h, then selecting pH successively is 11 aqueous solutions, 70% ethanol is easily separated parsing, collects and obtains Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent.
4. dried: adopt vacuum lyophilization mode to be dried the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent obtained, drying time is 36h, obtaining Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide conversion ratio prepared by this condition is 18.72%, purity 51.78%.
Claims (10)
1. a preparation method for Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide, comprises the following steps:
(1) preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution,
(2) clarifying treatment,
(3) separation, purification process,
(4) dried,
It is characterized in that, the concrete operations of step (1) are: adopt steam explosion coupling microwaves assisted extraction method that the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide in Radix Glycyrrhizae is extracted, obtain Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution.
2. the preparation method of a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 1, it is characterised in that concrete operations are:
(1) preparation of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution: adopt steam explosion coupling microwaves assisted extraction method that the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide in Radix Glycyrrhizae is extracted, obtain Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution;
(2) clarifying treatment: after the Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide extracting solution obtained is processed by centrifugation, obtain Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor;
(3) separation, purification process: utilize high speed adverse current chromatogram or macroporous resin that Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide clear liquor is easily separated purification, collect and obtain Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent;
(4) dried: adopt vacuum freeze-drying method that Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide eluent is dried process, obtain 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 any one of claim 1-2, it is characterised in that concretely comprising the following steps of steam explosion coupling microwaves assisted extraction described in step (1):
(1) pretreatment of Radix Glycyrrhizae: adopting acid solution that Radix Glycyrrhizae is soaked, the solid-to-liquid ratio of immersion is 1:1-3:1, and soaking temperature is 50 DEG C-70 DEG C, and soak time is 3-5h;
(2) steam explosion: the Radix Glycyrrhizae after soaking is carried out Steam explosion treatment, and steam explosion condition is: pressure is 6-10MPa, and blasting time is 5-15min;
(3) microwave radiation exaraction: the Radix Glycyrrhizae after steam explosion is carried out microwave radiation exaraction, liquid-solid ratio during extraction is 30:1-50:1, and extraction time is 10-60min, and Extracting temperature is 60-70 DEG C, microwave power is 300W-600W, and speed of agitator is 100-250rpm.
4. the preparation method of a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 3, it is characterised in that step (1) described acid solution is acetic acid, nitric acid or sulphuric acid, the concentration of described acid solution is 3-8%.
5. the preparation method of a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 2, it is characterised in that condition centrifugal described in step (2) is: rotating speed is 3600-4200rpm/min, and centrifugation time is 5-15min.
6. the preparation method of a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 2, it is characterized in that, the solvent system of the described high speed adverse current chromatogram separation purification of step (3) is: normal hexane: methanol: ethyl acetate: water=0.5:3:3:5 or 0:2:3:5.
7. the preparation method of a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 2, it is characterized in that, the type of elution of step (3) described high speed adverse current chromatogram separation purification is: first do mobile phase by fix phase, lower phase of phase, reversal connection is reversed, rotating speed is 600-800r/min, flow velocity is 1-2mL/min, eluting 4-6h; Then mobile phase being changed to upper phase, is changed to positive simultaneously and connects rotating forward, rotating speed is 600-800r/min, and flow velocity is 1-2mL/min, eluting 3-5h;
Or fix mutually under adopting phase, upper phase do mobile phase, just connecing rotating forward, rotating speed is 600-800r/min, and flow velocity is 1-2mL/min, eluting 8-10h.
8. the preparation method of a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 2, it is characterised in that the macroporous resin described in step (3) is EXA50, EXA45, SP825 or SP207.
9. the preparation method of a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 2, it is characterized in that, the condition of the described macroporous resin separation purification of step (3) is: resin content is 17-42mg/mL, adsorption time is 5-10h, then adopts the aqueous solution of pH8-12 and 30%-90% ethanol to be easily separated parsing successively.
10. the preparation method of a kind of Glycyrrhetic acid 3-O-mono-BETA-D-glucuronide according to claim 2, it is characterised in that the drying time described in step (4) is 24-36h.
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| CN106636290A (en) * | 2017-02-03 | 2017-05-10 | 江南大学 | Method for producing glycyrrhetinic acid monoglucuronide by 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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| 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 |
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| 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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