CN113861253A - Preparation method and application of genipin nucleotide monomer - Google Patents
Preparation method and application of genipin nucleotide monomer Download PDFInfo
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Abstract
The invention discloses a preparation method and application of a genipin acid monomer. The preparation method of the genipin acid monomer comprises the following steps: s101, adding eucommia ulmoides powder into a natural eutectic solvent for extraction to obtain a crude geniposide extraction solution; s102, adsorbing a crude geniposide extraction solution by using a special adsorbent purification method, removing a filtrate, washing with water, eluting with an ethanol solution, collecting an eluent, and drying the eluent to obtain a GPA active site; s103, preparing and separating the GPA active site, and concentrating and drying the collected GPA fraction under reduced pressure to obtain the geniposidic acid monomer. The genipin acid monomer prepared by the preparation method provided by the invention has high purity, and the method is simple and easy to realize.
Description
Technical Field
The invention relates to the technical field of plant extraction and preparation, in particular to a preparation method and application of a genipin acid monomer.
Background
Eucommia ulmoides (Eucommia ulmoides Oliver) is a plant of Eucommia of Eucommiaceae, is a unique and precious nourishing medicinal material in China, has the functions of tonifying liver and kidney, strengthening bones and muscles and preventing miscarriage, and is mainly distributed in provinces such as Sichuan, Guizhou, Jiangxi and Hubei in China. Therefore, the eucommia ulmoides has higher scientific research value, health care and medical value and economic development value.
The biological active components of eucommia bark include lignin, iridoid, flavonoid, polysaccharide, phenylpropanoid and the like, and the contained geniposidic acid has pharmacological actions of reducing blood pressure, resisting tumor, resisting oxidation, resisting aging and the like, and is one of the important active components of eucommia bark. Because the product has strong antihypertensive effect and better effect than pinoresinol diglucoside, the product is applied as a common health product additive in Japan, and the antioxidant, antitumor and other biological effects are also verified by related scientific research, however, the anti-aging effect of geniposide is still rarely researched at present, and the research report on the preparation identification and biological activity of geniposide monomer is not seen yet.
Preliminary research finds that the anti-aging effect of the geniposide monomer extracted from eucommia ulmoides is superior to that of other characteristic components of eucommia ulmoides, and in recent years, the aging of the world population is more and more serious, the proportion of the population over 65 years old in China to the population in the whole country in 2019 is 12.6%, the proportion of the population over 60 years old is 18.1%, and China is one of the countries with serious aging of the world population at present, so that the development of the anti-aging substance has wide market prospect and important social significance.
Disclosure of Invention
The invention aims to provide a preparation method and application of a geniposidic acid monomer aiming at the defects and shortcomings of the prior art, the geniposidic acid monomer is prepared by utilizing a natural low cosolvent to obtain a crude extract of the geniposidic acid, the geniposidic acid is enriched and purified by a special adsorbent purification method to obtain a GPA active site, and finally the geniposidic acid monomer with the purity of 90-95% is obtained by a preparative chromatographic separation technology.
In order to achieve the purpose, the invention adopts the technical scheme that: a preparation method of genipin nucleotide monomers comprises the following steps:
s101, adding eucommia bark powder into a natural eutectic solvent according to the material-liquid ratio of 1:1-1:100g/mL, and extracting at the temperature of 20-80 ℃ and the power of 50-500W for 10-90min to obtain 85-90% crude geniposide extraction liquid;
s102, adsorbing the crude geniposide extraction liquid obtained in the step S101 by using a special adsorbent purification method, discarding filtrate, washing with distilled water at 20-75 ℃, eluting with a solvent, collecting eluent, and drying the eluent to obtain GPA (geniposide) active sites with the content of 85-88%;
s103, carrying out preparative chromatographic separation on the GPA active site obtained in the step S102, and concentrating and drying the collected GPA fraction under reduced pressure to obtain the geniposide monomer with the purity of 90-95%. The extraction manner of step S101 is ultrasonic extraction.
Preferably, the natural eutectic solvent consists of betaine, L-lactic acid and distilled water in a ratio of the amount of the substances of 1: 1: 3-10.
Preferably, the step S101 specifically includes: adding eucommia ulmoides powder into a natural eutectic solvent according to the material-liquid ratio of 1:10-40g/mL, uniformly mixing, and performing ultrasonic extraction at 30-50 ℃ and 500W under 300-.
Preferably, the adsorbent in step S102 is a special adsorbent HG-2, and the amount of the adsorbent added is 1g per 1-2mL of the crude geniposide extract.
Further preferably, after the adsorbent fully adsorbs the crude geniposidic acid extract in step S102, the filtrate is discarded, and the filtrate is washed with distilled water at 20-75 ℃, and then eluted by the solvent, the specific steps of: after the geniposide crude extraction liquid is fully adsorbed by the special adsorbent HG-2, the filtrate is discarded, and the geniposide crude extraction liquid is washed for 3 to 6 times by distilled water with the temperature of 30 to 50 ℃ and then eluted by a solvent.
Further preferably, the solvent is selected from one of ethyl acetate, methanol and ethanol solution, and the volume fraction of the ethanol solution is 70-80%.
Preferably, the mobile phase for preparing GPA in step S103 has pH value of 2.0-4.0, phiBThe value is 0.15-0.28.
The invention also protects the genipin acid monomer prepared by the preparation method. The genipin monomer prepared by the preparation method has the purity as high as 90-95%.
The invention also protects the application of the geniposide acid monomer in preparing anti-inflammatory preparations or anti-aging preparations.
The activity determination method of the genipin acid monomer comprises the following steps: establishing a HUVEC oxidative damage model, diluting the genipin monomer into different concentrations, and respectively carrying out antioxidant detection, anti-inflammatory detection and anti-aging detection.
The antioxidant detection experiment specifically comprises the following steps of detecting cell supernatant lactate dehydrogenase: detection using Lactate Dehydrogenase (LDH) kit; and (3) detection of MDA content: detecting by using an MDA detection kit; and (3) detection of glutathione content: detecting by using a GSH detection kit; detection of intracellular reactive oxygen species levels: detecting the content of active oxygen in cells by using a DCFH-DA fluorescent probe; the anti-inflammatory detection adopts an ELISA method to detect the expression of protein; the anti-aging assay was analyzed by SA- β -galactosidase staining.
Compared with the prior art, the invention has the beneficial effects that: the method comprises the steps of preparing a crude extract of geniposidic acid by using a natural low cosolvent, enriching and purifying the geniposidic acid by using a solvent extraction method or a special adsorbent purification method to obtain a GPA active site, and finally obtaining a geniposidic acid monomer with the purity of 90-95% by using a preparative chromatographic separation technology; the geniposide monomer has good anti-aging activity and anti-inflammatory activity.
Drawings
FIG. 1 is a flow chart of the process for preparing genipin acid monomers according to the present invention;
FIG. 2 shows GPA monomer pair H2O2Influence profile of induced HUVEC injury;
FIG. 3 is a graph of the antioxidant effect of GPA monomers;
FIG. 4 is a graph of the anti-inflammatory effects of GPA monomers;
figure 5 is a graph of the anti-aging effect of GPA monomers, in which: a: a control group; b: h2O2Group (d); c: h2O2+ GPA experimental group.
Detailed Description
The following examples are further illustrative of the present invention and are not intended to be limiting thereof. The equipment and reagents used in the present invention are, unless otherwise specified, conventional commercial products in the art. Extractant BT-1, analytically pure, purchased from fine chemical research institute of south of Hunan, CAS number: 71-36-3. Adsorbent HG-2, analytically pure, available from miuiou chemical reagents ltd, department of tianjin, CAS No.: 64365-11-3. Ethyl acetate, analytical grade, available from Maxlin reagents, Inc. CAS number 141-78-6. Methanol, analytical grade, available from mclin reagents ltd, CAS No.: 67-56-1.
Example 1
As shown in fig. 1, a preparation method of geniposide monomer with anti-aging activity comprises the following steps:
s101, cleaning fresh eucommia ulmoides bark, naturally drying, drying in a vacuum oven at 50 ℃ for 24 hours, crushing by a crusher, and screening by a screen to obtain eucommia ulmoides bark powder; mixing 1g of eucommia bark powder with 10mL of natural eutectic solvent, wherein the natural eutectic solvent is prepared by mixing betaine, L-lactic acid and distilled water in a mass ratio of 1: 1: 4, mixing uniformly, carrying out ultrasonic treatment for 30min under the conditions that the temperature is 50 ℃ and the power is 300W, centrifuging for 10min at 4000r/min, and taking supernatant to obtain 89.7 percent of crude geniposide extraction liquid;
s102, adding 50g of special adsorbent HG-2 into 80mL of crude geniposide extraction liquid, fully adsorbing until the mixture is saturated, filtering, discarding filtrate, washing for 4 times (washing off impurities such as saccharides and inorganic salts) with distilled water at 35 ℃, then eluting for 4 times with ethanol with the volume fraction of 80%, collecting eluent, and drying concentrated solution to obtain GPA active sites with the content of 87.8%;
s103, carrying out preparative separation on the obtained GPA active site, wherein the pH value of a preparative chromatographic mobile phase is 2.8 and phiBThe value is 0.28, the collected GPA fraction is decompressed and concentrated, and vacuum freeze drying is carried out, so that the geniposide monomer with the purity of 93 percent is obtained. The structural characterization data is as follows:1H NMR(400MHz)δ1H NMR(D2 O,400MHz):7.16(IH,s,H-3),5.87(IH,s,H-7),5.34(1H,d,J＝6.2Hz,H-1),4.82(1H,d,J＝8.2Hz,H-1"),4.31(1H,d,J＝14.6Hz,H-10b),4.26(1H,d,J＝14.6Hz,H-10a),3.24(IH,q.J＝8.0Hz,H-5),2.30(1H,t,J＝6.2Hz,H-9),2.80(1H,d,J＝16.4Hz,H-6b),2.14(1H,d,J＝16.4Hz,H-6a)；13C NMR(D2at 0,100MHz, delta 178.5(C-11),149.8(C-3),143.9(C-8),131.8(C-7),120.6(C-4),101.2(C-1),98.6(C-1'),78.9(C-3'),78.4(C-5'),75.5(C-2'),72.2(C-4'),63.3(C-6)'), 62.3(C-10), 49.1(C-9), 40.8(C-6), 37.4 (C-5). And the reference (Guarnaccia R, Madyastha K M, Tegtmeyer E, et al. Geniposidic acid, an iridoid glucoside from Genipoa americana [ J]Tetrahedron Letters,1972,13(50): 5125-.
Example 2
The same as example 1, except that:
and S102, adding 50g of special adsorbent HG-2 into 80mL of crude geniposide extraction liquid, fully adsorbing until the mixture is saturated, filtering, removing filtrate, washing for 4 times (washing out impurities such as saccharides and inorganic salts) with distilled water at 35 ℃, eluting for 4 times with ethyl acetate, collecting eluent, and drying concentrated solution to obtain the GPA active site with the content of 65%.
Example 3
The same as example 1, except that:
step S102, taking 50g of special adsorbent HG-2, adding the special adsorbent HG-2 into 80mL of crude geniposide extraction liquid, fully adsorbing until the mixture is saturated, filtering, discarding filtrate, washing for 4 times (washing off impurities such as saccharides and inorganic salts) by using distilled water at 35 ℃, then eluting for 4 times by using methanol, collecting eluent, and drying concentrated solution to obtain GPA active site with the content of 81.2%.
Example 4
The same as example 1, except that:
step S102, taking 50g of special adsorbent HG-2, adding the special adsorbent HG-2 into 50mL of crude geniposide extraction liquid, fully adsorbing until the mixture is saturated, filtering, discarding filtrate, washing for 4 times (washing out impurities such as saccharides and inorganic salts) by using distilled water at 35 ℃, then eluting for 4 times by using 80% ethanol, collecting eluent, and drying concentrated solution to obtain GPA active site with the content of 60.8%.
Example 5
The same as example 1, except that:
step S102, taking 50g of special adsorbent HG-2, adding the special adsorbent HG-2 into 100mL of crude geniposide extraction liquid, fully adsorbing until the mixture is saturated, filtering, discarding filtrate, washing for 4 times (washing out impurities such as saccharides and inorganic salts) by using distilled water at 35 ℃, then eluting for 4 times by using ethanol solution with volume fraction of 80%, collecting eluent, and drying concentrated solution to obtain GPA active site with content of 75.3%.
Example 6
The same as example 1, except that:
step S102, taking 50g of special adsorbent HG-2, adding the special adsorbent HG-2 into 80mL of crude geniposidic acid extraction liquid, fully adsorbing until the mixture is saturated, filtering, discarding filtrate, washing for 4 times (washing out impurities such as saccharides and inorganic salts) by using distilled water at 35 ℃, then eluting for 2 times by using ethanol solution with volume fraction of 80%, collecting eluent, and drying concentrated solution to obtain GPA active site with content of 70.9%.
Example 7
The same as example 1, except that:
step S102, taking 50g of special adsorbent HG-2, adding the special adsorbent HG-2 into 80mL of crude geniposidic acid extraction liquid, fully adsorbing until the mixture is saturated, filtering, discarding filtrate, washing for 4 times (washing out impurities such as saccharides and inorganic salts) by using distilled water at 35 ℃, then eluting for 3 times by using 80% ethanol, collecting eluent, and drying concentrated solution to obtain GPA active sites with the content of 81.2%.
Comparative example 1
The only difference from example 1 is: the extraction methods for preparing the crude extraction liquid of the geniposide acid are different.
A preparation method of geniposide monomer with anti-aging activity comprises the following steps:
step S101, taking 5Kg of eucommia bark powder, placing the eucommia bark powder into a 100L multipurpose extraction tank, adding 60L of 80% ethanol solution by volume fraction, extracting for 3 times at 70 ℃ for 0.5 hour each time, combining the extracting solutions, filtering, and recovering the solvent under reduced pressure to obtain 88.6% of crude geniposide extracting solution;
the operations of S102 and S103 are the same as those of example 1.
Comparative example 2
The only difference from example 1 is: the purification method of the crude extraction liquid of the geniposide acid is different.
A preparation method of geniposide monomer with anti-aging activity comprises the following steps:
s101, the same procedure as in example 1 was repeated.
S102, extracting a crude geniposide extraction solution by adopting a solvent extraction method, wherein an extracting agent is BT-1, the pH value of a water phase is 3, and the ratio of the extracting agent to the water phase is 1: 3, extracting for 15min for 2 times, combining the extraction liquid for 2 times, recovering the organic solvent (which can be repeatedly used) under reduced pressure, and drying the concentrated solution to obtain GPA active site with the content of 80.5%;
s103, the operation is the same as in example 1.
Comparative example 3
The only difference from example 1 is: the purification method of the crude extraction liquid of the geniposide acid is different.
A preparation method of geniposide monomer with anti-aging activity comprises the following steps:
s101, the same procedure as in example 1 was repeated.
S102, purifying a crude geniposide acid extract by adopting a macroporous resin method, clarifying and ultrafiltering the crude geniposide acid extract, adjusting the pH value to 3 by using citric acid, adsorbing by using XAD-6 type macroporous adsorption resin, eluting by using 1BV of distilled water to remove impurities, wherein the elution rate is 2.5 BV/h; eluting with 3BV 6% ethanol water solution at an elution rate of 3BV/h, collecting the eluate, and drying the concentrated solution to obtain GPA active site with a content of 30%.
S103, the operation is the same as in example 1.
Experimental example 1
A method for determining genipin nucleotide monomers with anti-aging activity, comprising:
the genipin monomer with the purity of 93 percent prepared in example 1 is diluted into different concentrations to be tested.
1. The method comprises the following steps:
as shown in fig. 2, three groups are set for the experiment, respectively: blank group (group A), H2O2Group (B) and Experimental group (H)2O2+ GPA, where GPA (3.125uM) + H2O2(100uM)) (group C). Wherein, the antioxidant experiment: detection of lactate dehydrogenase in cell supernatants: detection using Lactate Dehydrogenase (LDH) kit; and (3) detection of MDA content: detecting by using an MDA detection kit; and (3) detection of glutathione content: detecting by using a GSH detection kit; intracellular reactive oxygen species content: and detecting the content of active oxygen in the cells by using a DCFH-DA fluorescent probe. Anti-inflammatory experiments: the expression of the protein was detected by ELISA. Anti-aging experiments: analysis was performed by SA- β -galactosidase staining.
2. The experimental results are as follows:
as shown in fig. 3, the oxidation resistance experiment shows that: the geniposide can reduce the content of LDH, MDA and ROS, increase the content of GSH-Px in cells and play a better role in antioxidation.
As shown in fig. 4, anti-inflammatory experiments showed that: the active ingredient geniposide can inhibit the increase of the concentration of NF-kappa B, ICAM-1 in oxidative damage cells and has better anti-inflammatory effect.
As shown in fig. 5, the anti-aging experiment showed that: the SA-beta-gal staining analysis shows that the geniposidic acid has the functions of protecting cells and relieving aging caused by cell oxidative damage.
The above examples are only preferred embodiments of the present invention, and it should be noted that the above preferred embodiments should not be considered as limiting the present invention, and the protection scope of the present invention should be subject to the scope defined by the claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and these modifications and adaptations should be considered within the scope of the invention.
Claims (9)
1. A preparation method of genipin acid monomer is characterized by comprising the following steps:
s101, adding eucommia bark powder into a natural eutectic solvent according to the material-liquid ratio of 1:1-1:100g/mL, and extracting at the temperature of 20-80 ℃ and the power of 50-500W for 10-90min to obtain a crude geniposide extraction solution;
s102, adsorbing the crude geniposide extraction liquid obtained in the step S101 by using a special adsorbent purification method, discarding filtrate, washing with distilled water at 20-75 ℃, eluting with a solvent, collecting eluent, and drying the eluent to obtain GPA active sites with the content of 85-88%;
s103, carrying out preparative chromatographic separation on the GPA active site obtained in the step S102, and concentrating and drying the collected GPA fraction under reduced pressure to obtain the geniposide monomer.
2. The method for preparing geniposide monomer according to claim 1, wherein the natural eutectic solvent is prepared from betaine, L-lactic acid and distilled water in a ratio of 1: 1: 3-10.
3. The method for preparing geniposide monomer according to claim 1, wherein step S101 comprises the following steps: adding eucommia ulmoides powder into a natural eutectic solvent according to the material-liquid ratio of 1:10-40g/mL, uniformly mixing, and performing ultrasonic extraction at 30-50 ℃ and 500W for 30-60min to obtain a crude geniposide extraction solution.
4. The method for preparing geniposide monomer according to claim 1, wherein the adsorbent in step S102 is a special adsorbent HG-2, and the amount of adsorbent added is 1g per 1-2mL of crude geniposide extract.
5. The method for preparing geniposide acid monomers according to claim 4, wherein in step S102, the adsorbent fully adsorbs geniposide acid crude extract, then the filtrate is discarded, and the filtrate is washed with distilled water at 20-75 ℃, and then the specific steps of eluting with solvent are as follows: after the geniposide crude extraction liquid is fully adsorbed by the special adsorbent HG-2, the filtrate is discarded, and the geniposide crude extraction liquid is washed for 3 to 6 times by distilled water with the temperature of 30 to 50 ℃ and then eluted by a solvent.
6. The method for preparing geniposide monomer according to claim 5, wherein the solvent is one selected from ethyl acetate, methanol and ethanol solution, and the volume fraction of the ethanol solution is 70-80%.
7. The method of claim 1, wherein the mobile phase for preparing GPA in step S103 has pH of 2.0-4.0 and phiBThe value is 0.15-0.28.
8. The geniposide monomer prepared by the preparation method of claim 1.
9. Use of the geniposide monomer of claim 8 in the preparation of an anti-inflammatory or anti-aging formulation.
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| CN114702537A (en) * | 2022-04-29 | 2022-07-05 | 中国农业科学院麻类研究所 | Method for separating geniposide and aucubin |
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