CN114592028B - Method for preparing notoginsenoside Fd and esculin XIII - Google Patents

Method for preparing notoginsenoside Fd and esculin XIII Download PDF

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CN114592028B
CN114592028B CN202011417616.0A CN202011417616A CN114592028B CN 114592028 B CN114592028 B CN 114592028B CN 202011417616 A CN202011417616 A CN 202011417616A CN 114592028 B CN114592028 B CN 114592028B
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esculin
notoginsenoside
xiii
cellulase
ginsenoside
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CN114592028A (en
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谢海峰
马素敏
潘萌
胡云岭
谢期林
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Chengdu Biopurify Ltd
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Abstract

The invention relates to a method for preparing notoginsenoside Fd and esculin XIII, belonging to the technical field of traditional Chinese medicines. The invention solves the technical problem of providing a method for preparing notoginsenoside Fd and esculin XIII with low cost. The method comprises the following steps: a. adjusting the pH value of the ginsenoside Rb3 solution to 4.5-5.0, and then adding cellulase for hydrolysis to obtain hydrolysate, wherein the concentration of the ginsenoside Rb3 solution is 1-100 g/L, and the concentration of the cellulase is 1-50000U/mL; b. separating and purifying the hydrolysate to obtain notoginsenoside Fd and esculin XIII. The method has simple process and low cost, provides a new way for preparing the notoginsenoside Fd and the esculin XIII, and has wide application prospect.

Description

Method for preparing notoginsenoside Fd and esculin XIII
Technical Field
The invention relates to a method for preparing notoginsenoside Fd and esculin XIII, belonging to the technical field of traditional Chinese medicines.
Background
The pseudo-ginseng leaves are palm-shaped compound leaves, 3-4 sheets of rotifer tops are grown, the length of leaf stems is 5-11.5 cm, and no hair exists on the surfaces; the leaf is in a shape of a line, and the growth of the leaf is less than 2cm. The main cultivation area is in the hundreds of colors of mountain, inkstone, guangnan, thalamus and Guangxi of Yunnan, and has high yield, high quality and famous people in the middle and outer areas.
The "Ben Cao gang mu" refers to the stem and leaf of Notoginseng radix "treating fracture, traumatic hemorrhage, stopping when applied, and dissipating the residual work at night when the bruises and the like. Recent researches show that the stem and leaf of pseudo-ginseng can also be used for medicine, and has small toxic and side effects. The notoginseng leaf contains more than 20 saponin components, which are reported. Pharmacological studies show that the active component of the stem and leaf total saponins of the stem and leaf of the pseudo-ginseng has similar effects on blood systems, cardiovascular systems, nervous systems and metabolic systems as pseudo-ginseng root saponins. Notoginseng radix saponin Fd, also called gypenoside IX, esculin IX, is a pure compound extracted from Notoginseng radix. Animal experiments show that notoginsenoside Fd can inhibit the proliferation of reactive astrocytes caused by pro-inflammatory mediators, thereby improving serious disorders. This new finding paves the way for clinical application of notoginsenoside Fd in alleviating astrocyte-mediated neuroinflammation. Esculin XIII, also known as gypenoside M, ginsenoside Mx, has excellent antioxidant capacity, and can increase expression of cytoprotective antioxidants by enhancing nuclear accumulation of Nrf 2; UVB-induced inhibition of NF- κB expression is reduced, thereby reducing over-release of inflammatory cytokines. Esculin XIII is a promising natural cosmetic ingredient for the prevention and treatment of UVB-induced skin lesions.
The main products of the stem and leaf of the pseudo-ginseng in the market are tea electuary, cosmetics, nourishment and the like, and the crude extract is used as the raw material, so that the resource utilization rate is low, and the technical level of the product is not high. The pharmacological activity of rare ginsenoside is attracting more and more attention, but the content of natural plant is extremely low, the source is limited, and the separation is difficult. Experiments prove that the content of notoginsenoside Fd and esculin XIII in the extract of the stem and leaf of the pseudo-ginseng is less than 0.5 percent. The enzymatic conversion method can prepare rare ginsenoside through hydrolyzing side chain glycosyl, and the enzymatic hydrolysis method hydrolyzes ginsenoside Rb3 in the stem and leaf of pseudo-ginseng to prepare pseudo-ginseng saponin Fd and esculin XIII, so that the production efficiency is high, the national policy requirements of low energy consumption, low pollution and high efficiency are met, and the comprehensive utilization of plant resources is facilitated.
At present, specific enzymes are adopted for enzymatic hydrolysis of ginsenoside, for example, chinese patent application No. 202010653370.0 discloses a beta-glucosidase, a coding gene thereof, expression and application thereof, and specific amino acid sequence enzymes are adopted for conversion of natural compounds such as ginsenoside Rb1, ginsenoside Rb2 and the like under proper conditions, so that the glucose group connected on ginsenoside C20 is removed. The Chinese patent application No. 201911117100.1 discloses a recombinant beta-glucosidase CB-3B and application thereof in the production of ginsenoside Rg 3. The Chinese patent application No. 201510036363.5 discloses a process for preparing panaxadiol saponins by biotransformation by recombinant glycoside hydrolase.
As can be seen, enzymes for hydrolyzing ginsenoside Rb3 are generally prepared by specific genetic engineering methods, which are costly and have not been found.
Disclosure of Invention
Aiming at the defects, the invention solves the technical problem of providing a method for preparing notoginsenoside Fd and esculin XIII with lower cost.
The invention relates to a method for preparing notoginsenoside Fd and esculin XIII, which is characterized by comprising the following steps:
a. hydrolysis: adjusting the pH value of the ginsenoside Rb3 solution to 4.5-5.0, and then adding cellulase for hydrolysis to obtain hydrolysate, wherein the concentration of the ginsenoside Rb3 solution is 1-100 g/L, and the concentration of the cellulase is 1-50000U/mL;
b. and (3) separating and purifying: separating and purifying the hydrolysate to obtain notoginsenoside Fd and esculin XIII.
In one embodiment of the present invention, in the step a, the concentration of the ginsenoside Rb3 solution is 2-50 g/L.
In one embodiment of the invention, in the step a, the concentration of the ginsenoside Rb3 solution is 2-10 g/L.
In some embodiments of the invention, the concentration of cellulase is 10 to 10000U/mL. In some embodiments of the invention, the concentration of cellulase is 10 to 4500U/mL.
In some embodiments of the invention, in step a, the time of hydrolysis is from 2 to 240 hours. In preferred embodiments of the invention, in step a, the time of hydrolysis is 72 to 120 hours.
In some embodiments of the invention, the cellulase is at least one of a novelin cellulase, a huff cellulase, a Su Kehan pectinase, a Xia Cheng cellulase, a tennincellulase, and a sirolimus cellulase.
In some embodiments of the present invention, in step a, the preparation method of the ginsenoside Rb3 solution comprises: dissolving Notoginseng radix stem and leaf, notoginseng radix stem and leaf extract or ginsenoside Rb3 with purity of above 50% in solvent to obtain ginsenoside Rb3 solution. The purity of the invention is weight percent.
As one embodiment of the invention, the solvent is water and an organic solvent, and the volume ratio of the organic solvent to the water is 0-0.25:1.
In some embodiments of the invention, the organic solvent is a lower alcohol or acetone.
In some embodiments of the invention, in step b, the separation and purification is performed using a gel column chromatography method, a silica gel column chromatography method, or an HPLC purification method.
Compared with the prior art, the invention has the following beneficial effects:
in the method, the existing cellulase is adopted as hydrolase to hydrolyze ginsenoside Rb3, thus obtaining notoginsenoside Fd and esculin XIII. The process is simple and the cost is low.
The method can improve the content of esculin XIII in the Rb3 raw material of 50% of the market from <0.5% to more than 25%, and improve the content of notoginsenoside Fd from < 0.2% to more than 25%. Through separation and purification, the purity of the notoginsenoside Fd and the purity of the esculin XIII can reach more than 98 percent. The method provides a new way for preparing the notoginsenoside Fd and the esculin XIII, and has wide application prospect.
Drawings
FIG. 1 is an HPLC chart of a raw material with purity of 98% Rb3 before and after hydrolysis in example 1, wherein FIG. A is an HPLC chart of a raw material with purity of 98% Rb3 before hydrolysis, and FIG. B is an HPLC chart after hydrolysis, wherein notoginsenoside Fd is circled.
Fig. 2 is an HPLC diagram of the raw material of the purity 98% rb3 before and after hydrolysis in example 2, wherein fig. a is an HPLC diagram of the raw material of the purity 98% rb3 before hydrolysis, and fig. B is an HPLC diagram after hydrolysis, and esculin XIII is encircled.
FIG. 3 is an HPLC chart of the purified notoginsenoside Fd.
Fig. 4 is an HPLC diagram of purified esculin XIII.
FIG. 5 shows a nuclear magnetic resonance spectrum (C-spectrum) of the purified notoginsenoside Fd. FIGS. 5a, 5b, 5c and 5d are partial enlarged views of nuclear magnetic patterns of purified notoginsenoside Fd.
FIG. 6 shows the nuclear magnetic pattern (C-pattern) of the purified esculin XIII. Fig. 6a, 6b, 6c and 6d are all partial enlarged views of the nuclear magnetic patterns of the purified esculin XIII.
FIG. 7 is a mass spectrum of the purified notoginsenoside Fd.
FIG. 8 is a mass spectrum of the purified esculin XIII.
Detailed Description
The invention relates to a method for preparing notoginsenoside Fd and esculin XIII, which is characterized by comprising the following steps:
a. hydrolysis: adjusting the pH value of the ginsenoside Rb3 solution to 4.5-5.0, and then adding cellulase for hydrolysis to obtain hydrolysate, wherein the concentration of the ginsenoside Rb3 solution is 1-100 g/L, and the concentration of the cellulase is 1-50000U/mL;
b. and (3) separating and purifying: separating and purifying the hydrolysate to obtain notoginsenoside Fd and esculin XIII.
In the method, the existing cellulase is adopted as hydrolase to hydrolyze ginsenoside Rb3, thus obtaining notoginsenoside Fd and esculin XIII. The process is simple and the cost is low.
Wherein the structure of ginsenoside Rb3 is shown in formula I, the structure of notoginsenoside Fd is shown in formula II, and the structure of esculin XIII is shown in formula III.
From the structural formula it can be seen that: notoginseng radix saponin Fd has one glucose less than ginsenoside Rb3, and esculin XIII has two glucose groups less than ginsenoside Rb 3. Theoretically, the glycosyl group of ginsenoside Rb3 can be reduced by glycosyl hydrolase, acid or alkali hydrolysis. A large number of experiments show that the ginsenoside Rb3 is not strong in targeting property by adopting acid or alkali hydrolysis, protopanaxadiol is easy to obtain, the yields of the product notoginsenoside Fd and esculin XIII are low, and the requirement of industrial production is difficult to meet. Enzyme hydrolysis is gradually used in industrial production due to its high efficiency and low pollution. The existing enzyme-directed hydrolysis is mostly realized by enzyme research and molecular structure optimization and adopts the specific enzyme of target gene expression of specific fragments. Through a large number of experiments, the inventor of the present invention found that the cellulase is adopted, and the dosage, substrate concentration, solvent composition, etc. of the cellulase are adjusted, so that the glucose group at the C3 position can be directionally hydrolyzed, and the notoginsenoside Fd and the esculin XIII are obtained.
Wherein, when the step a is hydrolyzed, if the concentration of ginsenoside Rb3 is too high, intermolecular hydrogen bonds can be formed in the solution, which hinders the enzyme hydrolysis efficiency; if the concentration of ginsenoside Rb3 is too low, the yields of notoginsenoside Fd and esculin XIII are low, the concentration cost is increased, and the concentration of ginsenoside Rb3 in the solution is preferably 1-100 g/L. In one specific embodiment, the concentration of the ginsenoside Rb3 solution is 2-50 g/L. In one specific embodiment, the concentration of the ginsenoside Rb3 solution is 2-10 g/L. In a specific embodiment of the invention, the concentration of the ginsenoside Rb3 solution is 2-5 g/L. In specific embodiments of the present invention, the concentration of ginsenoside Rb3 solution may be 2g/L, 2.5g/L, 5g/L, 7g/L, 8.5g/L, 10g/L, etc.
The concentration of the cellulase can influence the enzymolysis reaction, and the concentration of the cellulase is the initial concentration. Wherein, the enzyme amount of the cellulase for hydrolyzing 1wt% of the beta-glucan solution to generate 1ug of glucose in 1min under the condition of the optimal pH value and temperature is 1 cellulase activity unit U. Because the solubility of the cellulase is limited, excessive cellulose is added, so that waste is caused; if the concentration of cellulase is too low, the hydrolysis efficiency is low, and in some embodiments of the present invention, the concentration of cellulase is 10 to 10000U/mL. In some embodiments of the invention, the concentration of cellulase is 10 to 4500U/mL.
The hydrolysis time affects the conversion of the substrate and in some embodiments of the invention, the hydrolysis time is 2 to 240 hours. In preferred embodiments of the invention, the time of hydrolysis is 72 to 120 hours.
In some embodiments of the invention, the cellulase is at least one of a novelin cellulase, a huff cellulase, a Su Kehan pectinase, a Xia Cheng cellulase, a tennincellulase, and a sirolimus cellulase.
In the step a, the ginsenoside Rb3 solution can be prepared by a conventional method. In some embodiments of the present invention, the ginsenoside Rb3 solution is prepared by the following method: dissolving Notoginseng radix stem and leaf, notoginseng radix stem and leaf extract or ginsenoside Rb3 with purity of above 50% in solvent to obtain ginsenoside Rb3 solution.
In the method, the raw materials can be fresh leaves of the stem and leaf of the pseudo-ginseng, the extract of the stem and leaf of the pseudo-ginseng, the raw materials with Rb3 of 50% sold in the market or the high-purity raw materials with Rb3 more than 98%. Wherein, the water extract or the lower alcohol solution extract of the stem and leaf of the pseudo-ginseng is suitable for the invention, i.e. the stem and leaf extract of the pseudo-ginseng is the water extract or the lower alcohol solution extract.
The solvent may be a conventional aqueous solvent such as water, a mixture of water and an organic solvent, or a buffer solution in which water is compatible with the pH of the enzymatic hydrolysis.
As an embodiment of the present invention, the solvent is water or an organic solvent. Since ginsenoside Rb3 has limited solubility in water and poor solubility at higher concentration, a certain ratio of organic solvent is added, and the added type and the added amount of the organic solvent are based on the condition that the catalytic effect of enzyme is not affected, and the volume ratio of the organic solvent to the water is 0-0.25:1.
Common organic solvents are suitable for use in the present invention. In some embodiments of the invention, the organic solvent is a lower alcohol or acetone. In the present invention, the lower alcohol is methanol, ethanol, or the like.
And b, separating and purifying the hydrolysate in the step a to obtain the notoginsenoside Fd and the esculin XIII. In the step b, conventional separation and purification methods can be adopted, such as: separating and purifying by gel column chromatography, silica gel column chromatography and HPLC to obtain high purity Notoginseng radix saponin Fd and esculin XIII.
The following describes the invention in more detail with reference to examples, which are not intended to limit the invention thereto.
The conversion in the examples was calculated using the following method:
conversion (%) = (weight of ginsenoside Rb3 before hydrolysis-weight of ginsenoside Rb3 in the product after hydrolysis)/weight of ginsenoside Rb3 before hydrolysis×100%
Example 1
2g of a sample with 98% of ginsenoside Rb3 purity is weighed, and an HPLC chart of the sample is shown in FIG. 1.1L of water is dissolved, hydrochloric acid is added to adjust the pH value to 4.8, novelin cellulase is added, and the initial concentration of cellulase is 10U/mL. After 110h of reaction, the conversion rate of ginsenoside Rb3 is 85.2%, and the HPLC chart of the hydrolyzed product is shown in FIG. 1. Determining that the Fd percentage content of notoginsenoside in the product is 56.7%, and storing 750mg of the product after separation and purification, wherein the purity of the product is 98%; the esculin XIII content is 8.9%, 84.8mg is separated and purified for storage, and the purity of the product is 98%. HPLC of purified notoginsenoside Fd is shown in FIG. 3, HPLC of purified esculin XIII is shown in FIG. 4, nuclear magnetic spectrum (C spectrum) of purified notoginsenoside Fd is shown in FIG. 5, nuclear magnetic spectrum (C spectrum) of purified esculin XIII is shown in FIG. 6, mass spectrum of purified esculin Fd is shown in FIG. 7, and mass spectrum of purified esculin XIII is shown in FIG. 8.
Example 2
10g of a sample of ginsenoside Rb3 with purity of 98% is weighed, and the HPLC diagram of the sample is shown in FIG. 2.5L of water is dissolved, hydrochloric acid is added to adjust the pH value to 5.0, xia Cheng cellulase is added, and the initial concentration of the cellulase is 40U/mL. After 72 hours of reaction, the conversion rate of ginsenoside Rb3 is 83.5%, and the HPLC chart of the hydrolyzed product is shown in FIG. 2. Determining the Fd percentage content of notoginsenoside in the product to be 12%, and storing 0.79g after separation and purification, wherein the purity of the product is 98%; the percentage content of the esculin XIII is 55.3 percent, 3.04g of the product is separated and purified for warehousing, and the purity of the product is 98 percent. The characterization spectra are similar to those of figures 3-8.
Example 3
100g of a sample with the ginsenoside Rb3 purity of 50% (the percentage content of notoginsenoside Fd and esculin XIII in the sample is less than 0.5%) is weighed, 10L of water is dissolved, hydrochloric acid is added to adjust the pH value to 4.6, and the mixture of the Sabdariella and the Tian-Ye cellulase is added after the mixture is compounded according to the mass ratio of 1:1, wherein the total concentration of the initial cellulase is 4030U/mL. After 72 hours of reaction, the conversion rate of ginsenoside Rb3 is 82.3 percent, the content of notoginsenoside Fd in the product is measured to be 26.7 percent, 8.3g of the product is separated and purified and put in storage, and the purity of the product is 98 percent; the content of the esculin XIII is 45.3 percent, and 11.9g of the esculin is separated and purified for warehousing, and the purity of the esculin is 98 percent. The characterization spectra are similar to those of figures 3-8.
Example 4
Weighing 1000g of a sample with the ginsenoside Rb3 purity of 50% (the percentage content of notoginsenoside Fd and esculin XIII in the sample is less than 0.5%), dissolving in 200L of water, adding hydrochloric acid to adjust the pH value to 4.8, adding Su Kehan pectase and Saenocellulase after compounding according to the mass ratio of 3:1, and the total concentration of the initial cellulase is 350U/mL. After 72 hours of reaction, the conversion rate of ginsenoside Rb3 is 81.7%, the content of notoginsenoside Fd in the product is determined to be 38.5%, 133.2g of the product is separated and purified and put in storage, and the purity of the product is 98%; the content of the esculin XIII is 37.4 percent, 108.8g of the product is separated and purified for warehousing, and the purity of the product is 98 percent. The characterization spectra are similar to those of figures 3-8.

Claims (11)

1. A method for preparing notoginsenoside Fd and esculin XIII, comprising the steps of:
a. hydrolysis: adjusting the pH value of the ginsenoside Rb3 solution to 4.5-5.0, and then adding cellulase for hydrolysis to obtain hydrolysate, wherein the concentration of the ginsenoside Rb3 solution is 1-100 g/L, and the concentration of the cellulase is 1-50000U/mL;
b. and (3) separating and purifying: separating and purifying the hydrolysate to obtain notoginsenoside Fd and esculin XIII;
the cellulase is at least one of NoveXin cellulase, hui's wall cellulase, xia Cheng cellulase, tian Ye cellulase and Sau's Novo cellulase.
2. A process for preparing notoginsenoside Fd and esculin XIII according to claim 1, characterized in that: in the step a, the concentration of the ginsenoside Rb3 solution is 2-50 g/L.
3. The method for preparing notoginsenoside Fd and esculin XIII according to claim 2, wherein: in the step a, the concentration of the ginsenoside Rb3 solution is 2-10 g/L.
4. A process for preparing notoginsenoside Fd and esculin XIII according to claim 1, characterized in that: in the step a, the concentration of the cellulase is 10-10000U/mL.
5. A process for preparing notoginsenoside Fd and esculin XIII according to claim 4, wherein: in the step a, the concentration of the cellulase is 10-4500U/mL.
6. A process for preparing notoginsenoside Fd and esculin XIII according to claim 1, characterized in that: in the step a, the hydrolysis time is 2-240 h.
7. A process for preparing notoginsenoside Fd and esculin XIII according to claim 6, wherein: in the step a, the hydrolysis time is 72-120 h.
8. A process for preparing notoginsenoside Fd and esculin XIII according to claim 1, characterized in that: in the step a, the preparation method of the ginsenoside Rb3 solution comprises the following steps: dissolving Notoginseng radix stem and leaf, notoginseng radix stem and leaf extract or ginsenoside Rb3 with purity of above 50% in solvent to obtain ginsenoside Rb3 solution.
9. A process for preparing notoginsenoside Fd and esculin XIII according to claim 8, wherein: the solvent is water and an organic solvent, and the volume ratio of the organic solvent to the water is 0-0.25:1.
10. A process for preparing notoginsenoside Fd and esculin XIII according to claim 9, characterized in that: the organic solvent is lower alcohol or acetone.
11. A process for preparing notoginsenoside Fd and esculin XIII according to claim 1, characterized in that: in the step b, the separation and purification are carried out by adopting a gel column chromatography method, a silica gel column chromatography method or an HPLC purification method.
CN202011417616.0A 2020-12-07 2020-12-07 Method for preparing notoginsenoside Fd and esculin XIII Active CN114592028B (en)

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