CN116854761A - Rare ginsenoside pentamer and preparation method thereof - Google Patents
Rare ginsenoside pentamer and preparation method thereof Download PDFInfo
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- 229930182494 ginsenoside Natural products 0.000 title claims abstract description 69
- 229940089161 ginsenoside Drugs 0.000 title claims abstract description 68
- 238000002360 preparation method Methods 0.000 title claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 33
- 239000002994 raw material Substances 0.000 claims abstract description 26
- 238000000354 decomposition reaction Methods 0.000 claims abstract description 24
- 241000228212 Aspergillus Species 0.000 claims abstract description 18
- 108010059820 Polygalacturonase Proteins 0.000 claims abstract description 17
- 108010093305 exopolygalacturonase Proteins 0.000 claims abstract description 17
- 108090000790 Enzymes Proteins 0.000 claims abstract description 16
- 102000004190 Enzymes Human genes 0.000 claims abstract description 16
- 229940088598 enzyme Drugs 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 102100026189 Beta-galactosidase Human genes 0.000 claims abstract description 8
- 108010059881 Lactase Proteins 0.000 claims abstract description 8
- 108010005774 beta-Galactosidase Proteins 0.000 claims abstract description 8
- 229940116108 lactase Drugs 0.000 claims abstract description 8
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 24
- 229930182490 saponin Natural products 0.000 claims description 21
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- SYFJYASKXNAXKC-UHFFFAOYSA-N Panaxadiol Natural products CC1(C)CCCC(O1)C2CCC3(C)C2C(O)CC4C5(C)CCC(O)C(C)(C)C5CCC34C SYFJYASKXNAXKC-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
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- 241000196324 Embryophyta Species 0.000 description 2
- PHLXREOMFNVWOH-YAGNRYSRSA-N Ginsenoside Rh3 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]4C(\C)=C/CC=C(C)C)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O PHLXREOMFNVWOH-YAGNRYSRSA-N 0.000 description 2
- 241000180649 Panax notoginseng Species 0.000 description 2
- 235000003143 Panax notoginseng Nutrition 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- SWIROVJVGRGSPO-UHFFFAOYSA-N Ginsenoside F2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O SWIROVJVGRGSPO-UHFFFAOYSA-N 0.000 description 1
- AVTXSAWPGCSYFO-UHFFFAOYSA-N Ginsenoside Ia Natural products C1CC(C2(CC(O)C3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O AVTXSAWPGCSYFO-UHFFFAOYSA-N 0.000 description 1
- 241000186660 Lactobacillus Species 0.000 description 1
- 235000002789 Panax ginseng Nutrition 0.000 description 1
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- 238000010521 absorption reaction Methods 0.000 description 1
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
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- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- SWIROVJVGRGSPO-JBVRGBGGSA-N ginsenoside F2 Chemical compound O([C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O SWIROVJVGRGSPO-JBVRGBGGSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229940039696 lactobacillus Drugs 0.000 description 1
- 238000000874 microwave-assisted extraction Methods 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
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- 239000011347 resin Substances 0.000 description 1
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- 238000001179 sorption measurement Methods 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P33/00—Preparation of steroids
- C12P33/20—Preparation of steroids containing heterocyclic rings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
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Abstract
The invention discloses a rare ginsenoside pentad and a preparation method thereof, comprising the following steps: mixing the preparation raw materials with a solvent, a first acid and a decomposing enzyme to obtain a hydrolysis reaction system, and carrying out a decomposition reaction on the hydrolysis reaction system to obtain a first decomposition product, wherein the decomposing enzyme comprises aspergillus pectinase and/or lactase; mixing and reacting the first decomposition product with a second acid to obtain a second reaction system, wherein the second reaction system reacts at 80-110 ℃ to obtain a product containing rare ginsenoside pentad. The prepared product has various activities including anticancer, antifatigue, antivirus, anti-inflammatory, antidiabetic, anti-liver cirrhosis, antihypertensive, hypolipemic, uvioresistant, anti-skin aging and whitening effects, and particularly has remarkable inhibition effect on various types of cancers, so that the product can be used for preparing anticancer supplements and cosmetic whitening products in functional food and pharmaceutical industries.
Description
Technical Field
The invention belongs to the field of ginsenoside preparation, and in particular relates to a rare ginsenoside pentad and a preparation method thereof.
Background
The rare ginsenoside is taken as a trace component in the red ginseng, and is gradually perceived by masses of national people due to unique activity, and the monose ginsenoside 20 (S) -Rh2, 20 (R) -Rh2 and Rk2, (Z) -Rh3, (E) -Rh3 has more advantages in terms of bioavailability and absorption from the aspects of activity (anticancer, anti-fatigue, antiviral, anti-inflammatory, antidiabetic, anti-liver cirrhosis, antihypertensive, hypolipemic, uvioresistant, anti-skin aging, whitening and the like, and particularly has remarkable inhibition effect on various types of cancers).
The existing methods for preparing ginsenoside include microwave extraction method, supercritical fluid extraction method, enzymolysis method and the like, however, because ginsenoside has various types of Rb2, rc, rd, K compounds, mc compounds, O compounds and the like, the existing methods are rarely directed to the methods for preparing specific types of ginsenoside.
Disclosure of Invention
The invention mainly aims to provide a rare ginsenoside pentad and a preparation method thereof, and aims to solve the problem that the prior art cannot obtain ginsenoside 20 (S) -Rh2, 20 (R) -Rh2 and Rk2, (Z) -Rh3 and (E) -Rh3 in a targeted manner.
In order to achieve the above purpose, the invention provides a preparation method of rare ginsenoside pentad, comprising the following steps:
step S1, mixing a preparation raw material, a solvent, a first acid and a decomposing enzyme to obtain a hydrolysis reaction system, and carrying out a decomposition reaction to obtain a first decomposition product, wherein the decomposing enzyme comprises aspergillus pectinase and/or lactase, and the preparation raw material contains panaxadiol saponins;
and step S2, mixing the first decomposition product with a second acid to obtain a second reaction system, and reacting the second reaction system at 80-110 ℃ to obtain a product containing rare ginsenoside pentads.
Optionally, the solvent comprises water;
optionally, the panaxadiol saponin contains at least one of Rb1, rb2, and Rc.
Optionally, the first acid comprises lactic acid and/or citric acid; and/or the number of the groups of groups,
the second acid comprises lactic acid and/or citric acid.
Optionally, in the hydrolysis reaction system, the content of the preparation raw materials is 8 g/L-12 g/L; and/or the number of the groups of groups,
in the hydrolysis reaction system, the mass ratio of the preparation raw material, the first acid and the decomposing enzyme is (8-12): (0.8-1.2): 1.
optionally, the temperature of the decomposition reaction is 35-40 ℃; and/or the number of the groups of groups,
the time of the decomposition reaction is 10 to 20 hours.
Optionally, the mass ratio of the second acid to the first acid is (3-5): 1.
Optionally, after the step S2, the method further includes:
and step S3, purifying the product containing the rare ginsenoside pentad to obtain a ginsenoside monosaccharide pentad finished product.
Optionally, the step S3 includes: and (3) carrying out solid-liquid separation on the product containing the rare ginsenoside pentad, collecting solid, adding a purification solvent into the solid for dissolution, and concentrating to obtain a ginsenoside monosaccharide pentad finished product.
The invention also provides a rare ginsenoside pentad, which is prepared by adopting the preparation method of the rare ginsenoside pentad, and comprises at least one of 20 (S) -Rh2, 20 (R) -Rh2, rk2, (Z) -Rh3 and (E) -Rh 3.
According to the invention, the ginsenoside-containing diol saponin is degraded by adopting acid, enzyme and heat, so that the preparation methods of 20 (S) -Rh2, 20 (R) -Rh2, rk2, (Z) -Rh3 and (E) -Rh3 are specifically obtained, and the yield is relatively high; meanwhile, the one-pot method is adopted for operation, the method is simple, the cost is low, and the industrial popularization is good.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings that are required in the embodiments or the description of the prior art will be briefly described, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and other related drawings can be obtained according to the drawings without inventive effort for a person skilled in the art.
FIG. 1 is a flow chart showing an embodiment of a method for preparing a rare ginsenoside pentad according to the present invention;
FIG. 2 is a chromatographic chart of the product of example 1 of the present invention.
The achievement of the objects, functional features and advantages of the present invention will be further described with reference to the accompanying drawings, in conjunction with the embodiments.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention more clear, the technical solutions of the embodiments of the present invention will be clearly and completely described below. It will be apparent that the described embodiments are only some, but not all, embodiments of the invention.
The specific conditions were not specified in the examples, and the examples were conducted under the conventional conditions or the conditions recommended by the manufacturer. The reagents or apparatus used were conventional products commercially available without the manufacturer's attention. In addition, the meaning of "and/or" as it appears throughout includes three parallel schemes, for example "A and/or B", including the A scheme, or the B scheme, or the scheme where A and B are satisfied simultaneously. In addition, the technical solutions of the embodiments may be combined with each other, but it is necessary to base that the technical solutions can be realized by those skilled in the art, and when the technical solutions are contradictory or cannot be realized, the combination of the technical solutions should be regarded as not exist and not within the protection scope of the present invention. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
The existing extraction method of ginsenoside has no specific extraction method of 20 (S) -Rh2, 20 (R) -Rh2 and Rk2, (Z) -Rh3 and (E) -Rh 3.
To obtain the above-mentioned products, the inventors of the present invention first studied a method for obtaining specific ginsenoside, and patent application No. 201680062008.8 describes that ginsenoside F2, mc compound and O compound are selectively produced from refined ginsenoside (panaxadiol-containing saponin) using ginsenoside obtained specifically by aspergillus pectinase, and the patent does not obtain 20 (S) -Rh2, 20 (R) -Rh2 and Rk2, (Z) -Rh3, (E) -Rh3 as the main products, although specific transformation and production are achieved.
For this reason, the present invention provides a method for preparing a rare ginsenoside pentad, referring to fig. 1, fig. 1 is a flowchart of an embodiment of the method for preparing a rare ginsenoside pentad of the present invention, the method for preparing a rare ginsenoside pentad comprises the following steps:
step S1, mixing a preparation raw material with a solvent, a first acid and a decomposing enzyme to obtain a hydrolysis reaction system, and performing a decomposition reaction on the hydrolysis reaction system to obtain a first decomposition product, wherein the decomposing enzyme comprises aspergillus pectinase and/or lactase, and the preparation raw material contains panaxadiol saponins;
and step S2, mixing the first decomposition product with a second acid to obtain a second reaction system, and reacting the second reaction system at 80-110 ℃ to obtain a product containing rare ginsenoside pentads.
The inventor researches the team to find that, on the premise of taking panaxadiol saponins as raw materials, the panaxadiol saponins are subjected to enzymolysis under the acidic condition and then are subjected to reaction under the high-temperature condition, so that not only are the preparation methods of 20 (S) -Rh2, 20 (R) -Rh2, rk2, (Z) -Rh3 and (E) -Rh3 specifically obtained, but also the high yield is achieved; meanwhile, the one-pot method is adopted for operation, the method is simple, the cost is low, the industrial popularization is good, the one-pot method is an organic synthesis method, the multi-step reaction in the one-pot method reaction can be started from relatively simple and easily obtained raw materials, molecules with complex structures can be directly obtained without intermediate separation, and the method is economically and environmentally friendly.
It should be noted that, in the case where the reaction materials can be dissolved, the choice of solvent is not limited, and in some embodiments, the solvent includes water; when water is used as a solvent, the subsequent separation of the product can be facilitated.
The panaxadiol saponin contains at least one of Rb1, rb2 and Rc, specifically, the chemical structural formula of Rb1 is shown as follows:
the chemical structural formula of Rb2 is shown below:
the chemical structural formula of Rc is shown below:
in the invention, the raw materials for preparing the panaxadiol saponin can be commercial raw materials or can be prepared by the existing method, and the self-preparation method comprises the following steps: extracting plant materials, and separating by a macroporous adsorption resin according to a conventional method to obtain glycol-type saponin;
the plant material comprises at least one of ginseng flower stem and leaf, american ginseng flower stem and leaf, notoginseng flower stem and leaf, ginseng tail root and notoginseng fibrous root.
In some embodiments, the lytic enzyme comprises an aspergillus pectinase. The research team of the invention discovers that when aspergillus pectinase is adopted, the conversion efficiency can be further improved, and the yield of the target product can be improved.
In some embodiments, the first acid comprises lactic acid and/or citric acid; the addition of the first acid not only controls the enzymatic activity of the lytic enzyme, but also performs preliminary decomposition together with the lytic enzyme.
In some embodiments, the second acid comprises lactic acid and/or citric acid. The addition of the second acid can not only be matched with a high-temperature environment to inactivate the decomposing enzyme, but also decompose the product of preliminary decomposition again to obtain the target product.
In the hydrolysis reaction system, the content of the panaxadiol type saponin can be adjusted according to practical situations, and in some embodiments, the content of the preparation raw material in the hydrolysis reaction system is 8g/L to 12g/L. In a preferred embodiment, the content of the preparation raw material in the first reaction system is 10g/L.
In the hydrolysis reaction system, the mass ratio of the preparation raw material, the first acid and the decomposing enzyme may be adjusted according to actual conditions, and in some embodiments, the mass ratio of the preparation raw material, the first acid and the decomposing enzyme in the hydrolysis reaction system is (8-12): (0.8-1.2): 1. in a preferred embodiment, the mass ratio of the panaxadiol saponin, the first acid and the degrading enzyme is 10:1:1.
the mass ratio of the second acid to the first acid may be adjusted according to the specific situation, and in some embodiments, the mass ratio of the second acid to the first acid is (3-5): 1. In a preferred embodiment, the mass ratio of the second acid to the first acid is 4:1.
It should be noted that the temperature of the decomposition reaction may be adjusted according to the specific situation, and in some embodiments, the temperature of the decomposition reaction is between 35 ℃ and 42 ℃; in the above temperature range, the conversion efficiency of the enzyme can be improved. In a preferred embodiment, the decomposition reaction temperature is 40 ℃.
The time of the decomposition reaction may be adjusted according to the specific situation, and in some embodiments, the time of the decomposition reaction is 10 hours to 20 hours. The reaction time can be set to be complete. In a preferred embodiment the time for the decomposition reaction is 12 hours.
In some embodiments, after the step S2, the method further includes:
and step S3, purifying the product containing the rare ginsenoside pentad to obtain a rare ginsenoside pentad finished product. The target product with higher purity can be obtained by purifying the product; specifically, the step S3 includes: and (3) carrying out solid-liquid separation on the product containing the rare ginsenoside pentad, collecting solid, adding a purification solvent into the solid for dissolution, and concentrating to obtain a rare ginsenoside pentad finished product. In a preferred embodiment, the purification solvent comprises ethanol, thereby increasing the yield and purity of the desired product.
In addition, the invention also provides a rare ginsenoside pentad which is prepared by adopting the preparation method of the rare ginsenoside pentad, wherein the rare ginsenoside pentad comprises at least one of 20 (S) -Rh2 (CAS: 7821-33-2), 20 (R) -Rh2 (CAS: 112246-15-8), rk2 (CAS: 364779-14-6), Z) -Rh3 (CAS number: 105558-26-7) and E) -Rh3 (CAS number: 166040-90-0);
the prepared product has various activities including anticancer, antifatigue, antivirus, anti-inflammatory, antidiabetic, anti-liver cirrhosis, antihypertensive, hypolipemic, uvioresistant, anti-skin aging and whitening effects, and particularly has remarkable inhibition effect on various types of cancers, so that the product can be used for preparing anticancer supplements and cosmetic whitening products in functional food and pharmaceutical industries.
The following technical solutions of the present invention will be described in further detail with reference to specific examples and drawings, and it should be understood that the following examples are only for explaining the present invention and are not intended to limit the present invention.
In the present invention, the following are some of the reaction materials:
the preparation method of the panaxadiol saponin raw material comprises the following steps: adding 70% (v/v) ethanol into 10L of ginseng per kilogram for 5 years or less, extracting at 70deg.C for 1 hr, filtering, repeatedly extracting with 10L of 70% (v/v) ethanol per kilogram of filter residue, filtering, mixing filtrates, concentrating under reduced pressure, drying, dissolving each kilogram of dried material in 50L of water, sequentially washing with water, 30% (v/v) ethanol, eluting with 80% (v/v) ethanol, concentrating under increased pressure, and drying to obtain panaxadiol type saponin raw material.
Aspergillus pectinase: noveXin pectase Pectinex UItra CLEAR
Lactase: noveven lactase Lactobacillus Pure 7500L
Example 1
The embodiment provides a preparation method of rare ginsenoside pentad, which comprises the following operation steps:
100g of ginsenoside diol saponin raw material is dissolved in 10L of water, 10g of lactic acid and 10g of aspergillus pectinase are respectively added, the temperature is kept at 40 ℃ for 12h, TLC tracking is carried out, then 40g of lactic acid is added, the temperature is increased to boiling reflux for 12h, the precipitate is cooled and collected, dissolved in ethanol, filtered, concentrated under reduced pressure and dried, and 72g of product is obtained.
Example 2
The embodiment provides a preparation method of rare ginsenoside pentad, which comprises the following operation steps:
50kg of ginsenoside diol saponin raw material is dissolved in 5000L of water, 5kg of citric acid and 5kg of aspergillus pectinase are respectively added, the temperature is kept at 40 ℃ for 12 hours, TLC tracking is carried out, then 20kg of citric acid is added, the temperature is increased to boiling reflux for 12 hours, cooling is carried out, precipitation is collected, ethanol is dissolved, filtering and reduced pressure concentration are carried out, and 35.2kg of product is obtained after drying.
Example 3
The embodiment provides a preparation method of rare ginsenoside pentad, which comprises the following operation steps:
80g of ginsenoside diol saponin raw material is dissolved in 10L of water, 10g of lactic acid and 8g of aspergillus pectinase are respectively added, the temperature is kept at 35 ℃ for 20 hours, TLC tracking is carried out, then 32g of lactic acid is added and reacted for 14 hours at 80 ℃, the precipitate is cooled and collected, dissolved in ethanol, filtered, concentrated under reduced pressure and dried, and 54.4g of product is obtained.
Example 4
The embodiment provides a preparation method of rare ginsenoside pentad, which comprises the following operation steps:
120g of ginsenoside diol saponin raw material is dissolved in 10L of water, 9.6g of lactic acid, 8g of aspergillus pectinase and 4g of lactase are respectively added, the temperature is kept at 37 ℃ for 10 hours, TLC tracking is carried out, then 28.8g of lactic acid is added and reacted for 13 hours at 90 ℃, the precipitate is cooled and collected, dissolved in ethanol, filtered, concentrated under reduced pressure and dried, and 80.5g of product is obtained.
Example 5
The embodiment provides a preparation method of rare ginsenoside pentad, which comprises the following operation steps:
100g of ginsenoside diol saponin raw material is dissolved in 10L of water, 12g of lactic acid and 10 aspergillus pectase are respectively added, the temperature is maintained at 37 ℃ for 12h, TLC tracking is carried out, 36g of lactic acid is added, the temperature is increased to boiling reflux for 12h, the precipitate is cooled and collected, dissolved in ethanol, filtered, concentrated under reduced pressure, and 70.1g of product is obtained after drying.
Example 6
The present example provides a process for the preparation of a rare ginsenoside pentad, which is substantially the same as in example 1, except that all of the aspergillus pectinase is replaced by lactase, resulting in a product of 59.6g in mass.
Comparative example 1
The comparative example provides a process for preparing ginsenoside, which comprises the same steps as in example 1, except that lactic acid is not added, and the ginsenoside is directly heated to boiling and then refluxed.
Comparative example 2
This comparative example provides a process for preparing ginsenosides, which is operated in the same manner as in example 1, except that the treatment is performed without adding Aspergillus pectinase.
Test examples
Chromatographic analysis was performed on examples 1 to 6 and comparative examples 1 to 2, and the detection method was as follows:
ODS chromatographic column (4.6 mmid. Times.250 mm,5 μm), mobile phase acetonitrile-water (52:48), gradient elution, flow rate 1mL/min, detection wavelength 203nm, column temperature 35 ℃; the results of the tests show that the main products of examples 1 to 6 are the pentamers: 20 The main contents of (S) -Rh2, 20 (R) -Rh2, rk2, (Z) -Rh3, and (E) -Rh3 are shown in Table 1, and the chromatographic detection results of example 1 are shown in FIG. 2.
Table 1 chromatographic test results for examples 1 to 6 and comparative examples 1 to 2
| Content of pentad substance (%) | |
| Example 1 | Greater than 36 |
| Example 2 | Greater than 36 |
| Example 3 | Greater than 36 |
| Example 4 | Greater than 36 |
| Example 5 | Greater than 36 |
| Example 6 | More than 28 and less than 36 |
| Comparative example 1 | Less than 5 |
| Comparative example 2 | Less than 5 |
As can be seen from the above table, examples 1 to 6, which are treated with aspergillus pectinase, give 20 (S) -Rh2, 20 (R) -Rh2, rk2, (Z) -Rh3, (E) -Rh 3) with a content of more than 28% after the subsequent high temperature step in which an acid was added, and the examples 1 to 6, which are treated with aspergillus pectinase, are compared with comparative example 2, and the schemes of examples 1 to 6 are adopted:
furthermore, the research team of the present invention found that the yield and purity of the target substance was further improved and the content of the target product was increased to 36% when the treatment was performed with aspergillus pectinase.
The foregoing is merely a preferred embodiment of the present invention and is not intended to limit the scope of the present invention, but various modifications and variations will be apparent to those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (10)
1. The preparation method of the rare ginsenoside pentad is characterized by comprising the following steps of:
step S1, mixing a preparation raw material with a solvent, a first acid and a decomposing enzyme to obtain a hydrolysis reaction system, and performing a decomposition reaction on the hydrolysis reaction system to obtain a first decomposition product, wherein the decomposing enzyme comprises aspergillus pectinase and/or lactase, and the preparation raw material contains panaxadiol saponins;
and step S2, mixing the first decomposition product with a second acid to obtain a second reaction system, and reacting the second reaction system at 80-110 ℃ to obtain a product containing rare ginsenoside pentads.
2. The method of preparing a rare ginsenoside pentad of claim 1, wherein the solvent comprises water.
3. The method for preparing a rare ginsenoside pentad of claim 1, wherein the panaxadiol saponin comprises at least one of Rb1, rb2, and Rc.
4. The method of preparing a rare ginsenoside pentad of claim 1, wherein the first acid comprises lactic acid and/or citric acid; and/or the number of the groups of groups,
the second acid comprises lactic acid and/or citric acid.
5. The method for producing a rare ginsenoside pentad according to claim 1, wherein the content of the raw material for production is 8g/L to 12g/L in the hydrolysis reaction system; and/or the number of the groups of groups,
in the hydrolysis reaction system, the mass ratio of the preparation raw material, the first acid and the decomposing enzyme is (8-12): (0.8-1.2): 1.
6. the method for preparing a rare ginsenoside pentad according to claim 1, wherein the temperature of the decomposition reaction is 35-40 ℃; and/or the number of the groups of groups,
the time of the decomposition reaction is 10 to 20 hours.
7. The method of producing a rare ginsenoside pentad according to claim 1, wherein the mass ratio of the second acid to the first acid is (3 to 5): 1.
8. The method for preparing a rare ginsenoside pentad of claim 1, further comprising, after the step S2:
and step S3, purifying the product containing the rare ginsenoside pentad to obtain a ginsenoside monosaccharide pentad finished product.
9. The method of preparing a rare ginsenoside pentad of claim 8, wherein step S3 comprises: and (3) carrying out solid-liquid separation on the product containing the rare ginsenoside pentad, collecting solid, adding a purification solvent into the solid for dissolution, and concentrating to obtain a ginsenoside monosaccharide pentad finished product.
10. A rare ginsenoside pentad prepared by the preparation method of the rare ginsenoside pentad according to any one of claims 1 to 9, wherein the rare ginsenoside pentad comprises at least one of 20 (S) -Rh2, 20 (R) -Rh2, rk2, (Z) -Rh3, and (E) -Rh 3.
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| KR20170001037A (en) * | 2015-06-25 | 2017-01-04 | 서울대학교산학협력단 | The method for preparing panax ginseng extract with increased contents of selective dammaranes, and a pharmaceutical compositions of the same for prevention or treatment of sarcopenia-related diseases |
| CN109022529A (en) * | 2018-08-17 | 2018-12-18 | 吉林农业大学 | A kind of preparation method of ginsenoside enzymatic hydrolysis product |
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|---|---|---|---|---|
| KR20170001037A (en) * | 2015-06-25 | 2017-01-04 | 서울대학교산학협력단 | The method for preparing panax ginseng extract with increased contents of selective dammaranes, and a pharmaceutical compositions of the same for prevention or treatment of sarcopenia-related diseases |
| CN109022529A (en) * | 2018-08-17 | 2018-12-18 | 吉林农业大学 | A kind of preparation method of ginsenoside enzymatic hydrolysis product |
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