CN118044612A - Preparation method of ginsenoside ester health product - Google Patents
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- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 claims abstract description 8
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- 238000010828 elution Methods 0.000 claims description 6
- OENLNEZGRPNQDR-UHFFFAOYSA-N n,n-di(propan-2-yl)hexan-1-amine Chemical compound CCCCCCN(C(C)C)C(C)C OENLNEZGRPNQDR-UHFFFAOYSA-N 0.000 claims description 5
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- CKUVNOCSBYYHIS-LGYUXIIVSA-N 20(R)-Ginsenoside Rh2 Natural products O([C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1)[C@@H]1C(C)(C)[C@H]2[C@@](C)([C@H]3[C@](C)([C@@]4(C)[C@H]([C@H](O)C3)[C@@H]([C@](O)(CC/C=C(\C)/C)C)CC4)CC2)CC1 CKUVNOCSBYYHIS-LGYUXIIVSA-N 0.000 description 15
- CKUVNOCSBYYHIS-IRFFNABBSA-N (20S)-ginsenoside Rh2 Chemical compound O([C@H]1CC[C@]2(C)[C@H]3C[C@@H](O)[C@H]4[C@@]([C@@]3(CC[C@H]2C1(C)C)C)(C)CC[C@@H]4[C@@](C)(O)CCC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O CKUVNOCSBYYHIS-IRFFNABBSA-N 0.000 description 14
- 230000000694 effects Effects 0.000 description 10
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a preparation method of a ginsenoside ester health product, belonging to the field of health foods. The invention uses immobilized glucosidase to enzymolyze the total ginsenoside liquid to obtain rare ginsenoside, then carries out esterification reaction on rare ginsenoside and octanoyl chloride to synthesize rare ginsenoside esterified substance, and finally obtains the ginsenoside esterified substance health care product with selenium preparation. According to the invention, the rare ginsenoside is esterified and selenium is added, so that the absorption rate of the rare ginsenoside in the human body is improved in a synergistic way, the immunity is obviously enhanced, and the tumor inhibition rate is improved.
Description
Technical Field
The invention belongs to the field of health-care food, and in particular relates to a preparation method of a ginsenoside ester health-care product.
Background
Ginseng has both medicinal and edible value and has been in China for over two thousand years. Various researches have found that ginsenoside has various effects of resisting tumor, resisting inflammation, reducing blood sugar, resisting depression, regulating immunity, etc., and ginsenoside is the main active ingredient of ginseng, and various technologies are available for extracting ginsenoside from ginseng.
At present, the traditional extraction and separation methods, such as a reflux method, a solvent extraction method, a percolation method and the like, are mainly adopted to extract and enrich the rare ginsenoside in the pseudo-ginseng, and have the problems of small recovery rate, low enrichment factor and high cost of the target extract, and the chemical structure of the rare ginsenoside is easy to change. The enzymatic conversion of ginsenoside has strong selectivity, high catalytic efficiency and clear catalytic process, and can improve the substrate concentration and the catalytic efficiency of the enzyme by means of recombinase, enzyme structure modification, metabolic engineering and the like, thereby shortening the processing time and reducing the production cost. The rare ginsenoside and the common ginsenoside are different by 1-3 glycosyl molecules, so that the ginsenoside conversion is generally realized by glycosidase hydrolysis.
At present, a great deal of researches on the anti-tumor action mechanism, the extraction and separation process, the clinical application and the like of ginsenoside are carried out in China, and related ginsenoside products are already available, however, the human body absorption and utilization rate of all ginseng health care products in the market at present is low, the effect of the ginsenoside is greatly reduced, and the invention is especially provided in view of the fact.
Disclosure of Invention
Aiming at the problems in the background art, the invention aims to provide a preparation method of a ginsenoside ester health product, which has the technical effects of improving the absorptivity of rare ginsenoside in human bodies and improving the tumor inhibition rate (for example, liver cancer).
In order to achieve the above purpose, the present invention adopts the following technical scheme:
the invention provides a preparation method of a ginsenoside ester health product, which comprises the following steps:
Step one, performing enzymolysis on the total ginsenoside liquid by using immobilized glucosidase to obtain rare ginsenoside;
Dissolving the obtained rare ginsenoside in dichloromethane, adding N, N-diisopropylhexylamine and octanoyl chloride for reaction, washing with water after the reaction is finished, collecting dichloromethane layer solution, performing gradient elution, detecting eluent by thin-layer chromatography, and drying to obtain rare ginsenoside esterified substance;
and thirdly, mixing the obtained rare ginsenoside ester with a selenium preparation to obtain the ginsenoside ester health product.
Preferably, the immobilized glucosidase in the first step is Bgp 1. BglPm.
Preferably, the enzymolysis conditions in the first step are as follows: the pH value is 8.0, the temperature is 25 ℃, and the enzymolysis time is 4 hours.
Preferably, in the second step, the ratio of rare ginsenoside to dichloromethane is 1:50, and the ratio of N, N-diisopropylhexylamine to octanoyl chloride is 20:11.
Preferably, in the second step, N-diisopropylhexylamine and octanoyl chloride are slowly added in sequence under the ice bath condition, and the mixed solution is subjected to oscillation reaction for 1h at the temperature of 10-15 ℃.
Preferably, the step two gradient elution and eluent thin layer chromatography detection are specifically as follows: and (3) subjecting the dichloromethane layer solution to silica gel column chromatography, and performing gradient elution by using dichloromethane-methanol as an eluent, wherein the volume ratio of the dichloromethane to the methanol is 100:1, 80:1, 60:1, 40:1, 20:1 and 10:1, collecting the eluent of 40:1-10:1, collecting 10mL of eluent into a container, sequentially detecting by using thin layer chromatography, and collecting products with consistent rf values.
Preferably, the third step is to prepare the ginsenoside ester health care product according to the mixing proportion of 27% of rare ginsenoside ester, 0.016% of selenium and the balance of auxiliary materials.
Preferably, the auxiliary material is a mixture of medlar and mulberry; the ginsenoside ester health product is in the form of enteric capsule.
Compared with the prior art, the invention has the beneficial effects that:
1. by esterifying rare ginsenoside, the obtained rare ginsenoside esterified product has improved absorptivity of rare ginsenoside in human body, and improved tumor inhibiting rate (such as liver cancer).
2. Selenium is added in the formula, and is an essential element in a human body, and the selenium and the rare ginsenoside ester have synergistic effect on tumor inhibition, so that the tumor inhibition rate (for example, liver cancer) of the rare ginsenoside ester is improved, and the immunity enhancing effect is remarkably improved.
Drawings
FIG. 1 is a flow chart of the process for preparing the ginsenoside ester health product.
Fig. 2 is a graph of in vitro liver tumor inhibition of the ginsenoside ester health product provided by the embodiment of the invention.
Fig. 3 is an in vitro liver tumor inhibition weight chart of the ginsenoside ester health product provided by the embodiment of the invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be clearly and completely described in the following examples. The specific conditions are not noted in the examples and are carried out according to conventional conditions or conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
Example 1
Taking rare ginsenoside Rh2 as an example:
1. Taking 5mL of total ginsenoside solution, placing in a test tube, performing enzymolysis with immobilized glucosidase Bgp and immobilized glucosidase BglPm at pH of 8.0 and temperature of 25deg.C for 4 hr, converting into ginsenoside Rh2 with conversion rate of 68.32%, evaporating, and air drying to obtain ginsenoside Rh2 powder.
2. 1.246G of ginsenoside Rh2 powder is weighed and placed in a 250mL conical flask with a plug, 100mL of dichloromethane is used for dissolution, 516mg of N, N-diisopropylhexylamine is added under ice bath, 358mg of octanoyl chloride is slowly added, the mixed solution is subjected to oscillation reaction for 1h at 10-15 ℃, the reaction system is washed 3 times with 100mL of water each time after the reaction is completed, and a dichloromethane layer solution is collected. Firstly adding 100-200 meshes of silica gel (2 g of silica gel is added into 1g of dichloromethane solution) with 2 times of the amount into dichloromethane solution, stirring and concentrating, and then filling the mixture into a column by using 300-400 meshes of silica gel; after loading, the sample was rinsed with dichloromethane-methanol 100:1 (1 column volume), followed by sequentially 80:1, 60:1, 40:1, 20:1, 10:1, each gradient rinsed with one column volume of solvent. The eluent is collected in a ratio of 40:1 to 10:1, and each 10mL is collected in a test tube. The product of each test tube was examined by thin layer chromatography, and the product having consistent rf values was collected and dried to obtain 410mg of white powder (ginsenoside Rh2 caprylic acid monoester, rh 2-O).
3. Pulverizing and sieving dried ginsenoside Rh2 caprylic acid monoester, and making into enteric capsule of ginsenoside health product 0.125g according to the mixture ratio of ginsenoside Rh2 caprylic acid monoester 27%, selenium 0.016% and adjuvants fructus Lycii and Mori fructus.
Example 2 comparison of human absorption Rate of ginsenoside Rh2 and ginsenoside Rh2 esterified product
The membrane-spanning transport experiments of Caco2 monolayer cells were carried out using ginsenoside Rh2 and ginsenoside Rh2 ester obtained in the above examples, respectively, and the experimental data obtained are shown in Table 1:
TABLE 1
Note that: different letters in the same column represent significant differences (P < 0.05).
Typically compounds have Papp values of less than 1X 10cm/s, between 1X 10 -6 and 1X 10 -5 cm/s and greater than 1X 10 - 5 cm/s are considered to have lower (< 30%), moderate (30% -70%) and higher (> 70%) absorption in vivo. According to this standard, rh2 has a Papp value of less than 1×10 -6 cm/s in Caco2 monolayer cells, and Rh2 is presumed to be poorly absorbed in the human intestinal tract, conforming to the absorption efficiency 16.2% shown in previous studies, while Rh2-O has a moderate absorption, and has an absorption efficiency of 30% -70% in humans.
Example 3 comparison of tumor inhibition ratio of ginsenoside Rh2 and ginsenoside Rh2 esterified product
Anti-tumor experiments of Caco2 monolayer cells were performed using ginsenoside Rh2 and ginsenoside Rh2 ester obtained in the above examples (H22 mouse hepatoma cells are taken as an example):
Taking human liver cancer cell Hep G2 as a research object, examining in vitro anti-tumor effects of Rh2 and Rh2-O, and describing relative mechanisms of Rh2 and Rh2-O induced Hep G2 apoptosis from the cellular molecular level by using techniques such as flow cytometry, western blot, Q-PCR, fluorescent staining and the like; h22 tumor-bearing mice are constructed as models, and a negative control group (distilled water), a positive control group (25 mg/kg cyclophosphamide), a Rh2 group (5 mg/kg, 10 mg/kg) and a Rh2-O (5 mg/kg, 10 mg/kg) are established to study the in vivo antitumor effect and mechanism of Rh2 and Rh 2-O.
Rh2-O has better effect on inhibiting growth of Hep G2 cells and better ability to induce apoptosis of Hep G2 cells than Rh2 (P < 0.05). Rh2-O treated Hep G2 cells had an IC 50 of 20.15. Mu.M for 24h, which was approximately half of the IC 50 of Rh 2. The tumor inhibition rate of Rh2-O is 50.6%, the tumor inhibition effect is obviously better than Rh2 (28.2%) (P < 0.05), and the immunity can be obviously improved.
EXAMPLE 4 comparison of tumor inhibition rates of selenium and ginsenoside Rh2 esters alone and in combination
Taking a human liver cancer cell Hep G2 as a research object, examining the in vitro anti-tumor effect of selenium and Rh2-O, and describing the related mechanism of Rh2 and Rh2-O induced Hep G2 apoptosis from the cellular molecular level by using technologies such as flow cytometry, western blot, Q-PCR, fluorescent staining and the like; h22 tumor-bearing mice are constructed as models, negative control groups (distilled water), selenium and Rh2-O groups (3 mg/kg selenium and Rh 2-O20 mg/kg), selenium groups (3 mg/kg) and Rh2-O (20 mg/kg) groups are established, and the in vitro anti-tumor effects of selenium and Rh2-O are studied, and the results are shown in figures 2 and 3.
As can be seen from FIGS. 2 and 3, the combined use of selenium and Rh2-O has a tumor diameter of < 2mm, a weight of 0.01g, a tumor diameter of 4mm in the group of Rh2-O, a weight of 0.03g, a tumor diameter of 6mm in the group of Rh2-O, a tumor diameter of 0.06g in the group of selenium alone, and a tumor diameter of 14mm in the group of blank and a weight of 0.21g; it can be seen that the combination of selenium and Rh2-O further enhances the growth inhibition effect on Hep G2 cells and the ability to induce apoptosis of Hep G2 cells.
The embodiments described above represent only a few preferred embodiments of the present invention, which are described in more detail and are not intended to limit the present invention. It should be noted that various changes and modifications can be made to the present invention by those skilled in the art, and any modifications, equivalent substitutions, improvements, etc. which are within the spirit and principle of the present invention are included in the scope of the present invention.
Claims (8)
1. A preparation method of a ginsenoside ester health product is characterized by comprising the following steps:
Step one, performing enzymolysis on the total ginsenoside liquid by using immobilized glucosidase to obtain rare ginsenoside;
Dissolving the obtained rare ginsenoside in dichloromethane, adding N, N-diisopropylhexylamine and octanoyl chloride for reaction, washing with water after the reaction is finished, collecting dichloromethane layer solution, performing gradient elution, detecting eluent by thin-layer chromatography, and drying to obtain rare ginsenoside esterified substance;
and thirdly, mixing the obtained rare ginsenoside ester with a selenium preparation to obtain the ginsenoside ester health product.
2. The method for preparing a health product of ginsenoside esters according to claim 1, wherein the immobilized glucosidase in the first step is Bgp, bglPm.
3. The method for preparing a ginsenoside ester health product according to claim 1, wherein the enzymolysis conditions in the first step are as follows: the pH value is 8.0, the temperature is 25 ℃, and the enzymolysis time is 4 hours.
4. The method for preparing a ginsenoside ester health product according to claim 1, wherein the ratio of rare ginsenoside to dichloromethane in the second step is 1:50, and the ratio of N, N-diisopropylhexylamine to octanoyl chloride is 20:11.
5. The method for preparing a ginsenoside ester health product according to claim 1, wherein in the second step, N-diisopropylhexylamine and octanoyl chloride are slowly added in sequence under ice bath condition, and the mixed solution is subjected to shake reaction for 1h at 10-15 ℃.
6. The method for preparing the ginsenoside ester health product according to claim 1, wherein the step two is gradient elution and eluent thin layer chromatography detection specifically comprises: and (3) subjecting the dichloromethane layer solution to silica gel column chromatography, and performing gradient elution by using dichloromethane-methanol as an eluent, wherein the volume ratio of the dichloromethane to the methanol is 100:1, 80:1, 60:1, 40:1, 20:1 and 10:1, collecting the eluent of 40:1-10:1, collecting 10mL of eluent into a container, sequentially detecting by using thin layer chromatography, and collecting products with consistent rf values.
7. The method for preparing a ginsenoside ester health product according to claim 1, wherein the ginsenoside ester health product is prepared by mixing 27% of rare ginsenoside ester, 0.016% of selenium and the balance of auxiliary materials.
8. The method for preparing a ginsenoside ester health product according to claim 7, wherein the auxiliary material is a mixture of medlar and mulberry; the ginsenoside ester health product is in the form of enteric capsule.
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