CN114592028A - Method for preparing notoginsenoside Fd and esculin XIII - Google Patents

Method for preparing notoginsenoside Fd and esculin XIII Download PDF

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CN114592028A
CN114592028A CN202011417616.0A CN202011417616A CN114592028A CN 114592028 A CN114592028 A CN 114592028A CN 202011417616 A CN202011417616 A CN 202011417616A CN 114592028 A CN114592028 A CN 114592028A
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notoginsenoside
esculin
cellulase
ginsenoside
xiii
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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 aims to provide 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 a 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 lower 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 pieces of stems grow in a wheel, the leaf stems are 5-11.5 cm long, and no hair exists on the surface; the shape of the leaf supporting line is linear, the cluster grows, and the growth is less than 2 cm. The main cultivation areas are all the colors of the Yunnan Wenshan, the inkstone, the Guannan, the hillside and the Guangxi, and have high yield and high quality.
From Ben Cao gang mu, it is said that the stem and leaf of Panax notoginseng "treat fracture and traumatic bleeding, and stop when applying it, while swelling and swelling will be treated by the same root after the night. Recent research shows that the stem and leaf of notoginseng can be used as medicine with less toxic side effect. The leaves of notoginseng contain a plurality of saponin components, and more than 20 types are reported. Pharmacological research shows that the active component of the stem and leaf of notoginseng is the total saponin of the stem and leaf of notoginseng, which has similar action to the saponin of notoginseng root in blood system, cardiovascular system, nervous system and metabolic system. Notoginsenoside Fd, also known as gypenoside IX and esculin IX, is a pure compound extracted from Notoginseng radix. Animal experiments show that the notoginsenoside Fd can inhibit reactive astrocyte proliferation caused by proinflammatory mediators, thereby improving serious obstacles. This new discovery paves the way for the clinical application of notoginsenoside Fd in the reduction of astrocyte-mediated neuroinflammation. Esculin XIII (also called gypenoside M and ginsenoside Mx) has excellent antioxidant capacity and can improve the expression of cytoprotective antioxidant by enhancing the nuclear accumulation of Nrf 2; the inhibition of NF-kB expression induced by UVB is reduced, so that the excessive release of inflammatory cytokines is reduced. Esculin XIII is a promising natural cosmetic ingredient for the prevention and treatment of UVB-induced skin damage.
The main products of the stems and leaves of the pseudo-ginseng in the market are tea granules, cosmetics, nutriments and the like, and the crude extracts of the pseudo-ginseng are used as raw materials, so that the resource utilization rate is low, and the product technology level is not high. The pharmacological activity of rare ginsenoside is more and more concerned, but the content of natural plant is very low, the source is limited, and the isolation is difficult. The content of notoginsenoside Fd and esculin XIII in the stem and leaf extract of Panax notoginseng is less than 0.5%. The enzymatic conversion method can prepare rare ginsenoside by hydrolyzing side chain glycosyl, and the enzymatic hydrolysis method can prepare notoginsenoside Fd and esculin XIII by hydrolyzing ginsenoside Rb3 in stem and leaf of Panax notoginseng, 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, enzymatic hydrolysis of ginsenosides adopts specific enzymes, for example, Chinese patent application No. 202010653370.0 discloses a beta-glucosidase, its coding gene and its expression and application, which adopts specific amino acid sequence enzyme to convert natural compounds such as ginsenoside Rb1 and ginsenoside Rb2 under appropriate conditions to remove glucosyl group connected to ginsenoside C20. The Chinese invention patent with the application number of 201911117100.1 discloses a recombinant beta-glucosidase CB-3B and application thereof in producing ginsenoside Rg 3. The Chinese patent with application number of 201510036363.5 discloses a process for preparing panaxadiol saponins by biotransformation of recombinant glycoside hydrolase.
Therefore, the enzyme for hydrolyzing ginsenoside is generally prepared by a specific genetic engineering method, the cost is high, and the enzyme for hydrolyzing ginsenoside Rb3 is not found.
Disclosure of Invention
Aiming at the defects, the technical problem to be solved by the invention is to provide a method for preparing notoginsenoside Fd and esculin XIII with low cost.
The invention discloses 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 a 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. separation and purification: separating and purifying the hydrolysate to obtain notoginsenoside Fd and esculin XIII.
In one embodiment of the invention, in the step a, the concentration of the ginsenoside Rb3 solution is 2-50 g/L.
In a specific 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 the cellulase is 10 to 10000U/mL. In some embodiments of the invention, the concentration of the cellulase is 10-4500U/mL.
In some embodiments of the present invention, in step a, the hydrolysis time is 2 to 240 hours. In some preferred embodiments of the present invention, in step a, the hydrolysis time is 72 to 120 hours.
In some embodiments of the invention, the cellulase is at least one of a novacin cellulase, a hebetel cellulase, a sukohamaca cellulase, a xiasheng cellulase, a tianye cellulase, and a carnot 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 more than 50% with solvent to obtain ginsenoside Rb3 solution. The purity of the invention is in weight percent.
In one embodiment of the present invention, the solvent is water and an organic solvent, and the volume ratio of the organic solvent to the water is 0 to 0.25: 1.
In some embodiments of the invention, the organic solvent is a lower alcohol or acetone.
In some embodiments of the present invention, in step b, the separation and purification are performed by gel column chromatography, silica gel column chromatography or HPLC purification.
Compared with the prior art, the invention has the following beneficial effects:
the method of the invention adopts the existing cellulase as hydrolase to hydrolyze the ginsenoside Rb3 to obtain the notoginsenoside Fd and the esculin XIII. The process is simple and the cost is low.
The method can improve the content of esculin XIII in 50% of Rb3 raw materials sold in the market from less than 0.5% to more than 25%, and improve the content of notoginsenoside Fd from less than 0.2% to more than 25%. Through separation and purification, the purity of the notoginsenoside Fd and the esculin XIII can reach more than 98 percent. The method provides a new way for preparing notoginsenoside Fd and esculin XIII, and has wide application prospect.
Drawings
Fig. 1 is an HPLC diagram of 98% purity Rb3 starting material before and after hydrolysis in example 1, wherein a is an HPLC diagram of 98% purity Rb3 starting material before hydrolysis, and B is an HPLC diagram after hydrolysis, in which notoginsenoside Fd is circled.
FIG. 2 is an HPLC chart of 98% Rb3 raw material before and after hydrolysis in example 2, wherein, the chart A is an HPLC chart of 98% Rb3 raw material before hydrolysis, the chart B is an HPLC chart after hydrolysis, and esculin XIII is encircled in the chart.
FIG. 3 is an HPLC chart of purified notoginsenoside Fd.
FIG. 4 is an HPLC chart of purified esculin XIII.
Fig. 5 is a nuclear magnetic spectrum (C spectrum) of purified notoginsenoside Fd. Fig. 5a, 5b, 5c and 5d are enlarged views of nuclear magnetic spectra of purified notoginsenoside Fd.
FIG. 6 is a nuclear magnetic spectrum (C spectrum) of purified esculin XIII. FIGS. 6a, 6b, 6c and 6d are enlarged views of nuclear magnetic spectra of purified esculin XIII.
Fig. 7 is a mass spectrum of purified notoginsenoside Fd.
FIG. 8 is a mass spectrum of purified esculin XIII.
Detailed Description
The invention discloses 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 a 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. separation and purification: separating and purifying the hydrolysate to obtain notoginsenoside Fd and esculin XIII.
The method of the invention adopts the existing cellulase as hydrolase to hydrolyze the ginsenoside Rb3 to obtain the 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.
As can be seen from the structural formula: notoginsenoside Fd has one less glucose than ginsenoside Rb3, and esculin XIII has two less glucose than ginsenoside Rb 3. In theory, glycosyl hydrolysis, acid or base hydrolysis may be used to reduce the glycosyl groups of ginsenoside Rb 3. A large number of experiments show that the ginsenoside Rb3 is hydrolyzed by acid or alkali, the target property is not strong, protopanaxadiol is easy to obtain, the yields of the products of notoginsenoside Fd and esculin XIII are low, and the requirements of industrial production are difficult to meet. The 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 adopting a specific fragment of target gene expression specific enzyme through enzymology research and molecular structure optimization. Through a large number of experiments, the inventor of the invention finds that the glucose group at C3 can be directionally hydrolyzed by adopting cellulase and adjusting the dosage, the substrate concentration, the solvent composition and the like, thereby obtaining the notoginsenoside Fd and the esculin XIII.
Figure BDA0002820683580000041
Wherein, when the ginsenoside Rb3 concentration is too high during the hydrolysis in the step a, intermolecular hydrogen bonds are formed in the solution, and the enzyme hydrolysis efficiency is hindered; if the concentration of the ginsenoside Rb3 is too low, the yield of the notoginsenoside Fd and the esculin XIII is low, the concentration cost is increased, and the concentration of the ginsenoside Rb3 in the solution is proper to be 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 invention, the concentration of the ginsenoside Rb3 solution can be 2g/L, 2.5g/L, 5g/L, 7g/L, 8.5g/L, 10g/L, and the like.
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 1 wt% of 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, the waste can be caused by excessive addition; and if the concentration of the cellulase is too low, the hydrolysis efficiency is low, and in some embodiments of the invention, the concentration of the cellulase is 10-10000U/mL. In some embodiments of the invention, the concentration of cellulase is 10-4500U/mL.
The hydrolysis time affects the conversion rate of the substrate, and in some embodiments of the invention, the hydrolysis time is 2-240 hours. In some preferred embodiments of the present invention, the hydrolysis time is 72 to 120 hours.
In some embodiments of the invention, the cellulase is at least one of a novacin cellulase, a hebetel cellulase, a sukohamaca cellulase, a xiasheng cellulase, a tianye cellulase, and a carnot cellulase.
In step a, the ginsenoside Rb3 solution can be prepared by a conventional method. In some embodiments of the invention, the ginsenoside Rb3 solution is prepared using the following method: dissolving Notoginseng radix stem and leaf, Notoginseng radix stem and leaf extract or ginsenoside Rb3 with purity of more than 50% with solvent to obtain ginsenoside Rb3 solution.
The raw materials of the method can be fresh leaves of stems and leaves of panax notoginseng, extracts of stems and leaves of panax notoginseng, commercially available raw materials with 50 percent of Rb3 or high-purity raw materials with Rb3 of more than 98 percent. Wherein, the water extract or the lower alcohol solution extract of the stem and leaf of the pseudo-ginseng is suitable for the invention, namely the water extract or the lower alcohol solution extract of the stem and leaf of the pseudo-ginseng.
The solvent may be a conventional aqueous solvent, such as water, a mixture of water and an organic solvent, or a buffer in which water is compatible with the pH of the enzymatic hydrolysis.
In one embodiment of the present invention, the solvent is water and an organic solvent. Because the solubility of the ginsenoside Rb3 in water is limited, and the solubility is poor when the concentration is higher, a certain ratio of organic solvent is added, the type and the addition amount of the organic solvent are based on the condition that the catalytic effect of the enzyme is not influenced, and the volume ratio of the organic solvent to the water is 0-0.25: 1.
The usual organic solvents are suitable for 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 obtained in the step a to obtain notoginsenoside Fd and esculin XIII. Conventional separation and purification methods can be adopted in the step b, such as: separating and purifying by gel column chromatography, silica gel column chromatography, HPLC purification method, etc. to obtain high purity notoginsenoside Fd and esculin XIII product.
The following examples are provided to further illustrate the embodiments of the present invention and are not intended to limit the scope of the present invention.
The conversion in the examples was calculated as follows:
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% purity of ginsenoside Rb3 was weighed, and the HPLC chart of this sample is shown in FIG. 1. Dissolving in 1L of water, adding hydrochloric acid to adjust pH value to 4.8, adding Novoxil cellulase, and the initial cellulase concentration is 10U/mL. After 110h reaction, the conversion rate of ginsenoside Rb3 was 85.2%, and the HPLC chart of the hydrolyzed product is shown in FIG. 1. Determining that the percentage content of notoginsenoside Fd in the product is 56.7%, and separating and purifying to obtain 750mg of product, and warehousing the product, wherein the purity of the product is 98%; the percent content of the esculin XIII is 8.9 percent, 84.8mg of the esculin XIII is separated and purified and then put in storage, and the purity of the product is 98 percent. The HPLC chart of the purified notoginsenoside Fd is shown in figure 3, the HPLC chart of the purified esculin XIII is shown in figure 4, the nuclear magnetic spectrum (C spectrum) of the purified notoginsenoside Fd is shown in figure 5, the nuclear magnetic spectrum (C spectrum) of the purified esculin XIII is shown in figure 6, the mass spectrum of the purified notoginsenoside Fd is shown in figure 7, and the mass spectrum of the purified esculin XIII is shown in figure 8.
Example 2
10g of a sample of ginsenoside Rb3 with 98% purity was weighed out and the HPLC chart of this sample is shown in FIG. 2. Dissolving with 5L of water, adding hydrochloric acid to adjust pH value to 5.0, and adding Xiasang cellulase with initial cellulase concentration of 40U/mL. After 72 hours of reaction, the conversion rate of ginsenoside Rb3 was 83.5%, and the HPLC chart of the hydrolyzed product is shown in FIG. 2. Determining the percentage content of notoginsenoside Fd in the product to be 12%, and separating and purifying to obtain 0.79g of notoginsenoside Fd which is put in a warehouse, wherein the purity of the product is 98%; the percent content of esculin XIII is 55.3%, and 3.04g of product is separated and purified and put in storage, and the purity of the product is 98%. The characteristic spectrum is similar to that of figures 3-8.
Example 3
100g of a sample with 50% of ginsenoside Rb3 purity (the contents of notoginsenoside Fd and esculin XIII in the sample are both less than 0.5%) is weighed, 10L of water is dissolved, hydrochloric acid is added to adjust the pH value to 4.6, Hemarthria wallichiana cellulase and Tianye cellulase are added after being compounded according to the mass ratio of 1:1, and the total concentration of the initial cellulase is 4030U/mL. After 72 hours of reaction, the conversion rate of the ginsenoside Rb3 is 82.3 percent, the percentage content of notoginsenoside Fd in the product is determined to be 26.7 percent, 8.3g of notoginsenoside Fd is separated and purified and then put in a warehouse, and the purity of the product is 98 percent; the percent content of esculin XIII is 45.3%, 11.9g of product is separated and purified and put in storage, and the purity of the product is 98%. The characteristic spectrum is similar to that of figures 3-8.
Example 4
Weighing 1000g of a sample with 50% of ginsenoside Rb3 (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 the mixture of hecohuo fruit cellulase and Senao cellulase in a mass ratio of 3:1, and adding the mixture of the original cellulase with the total concentration of 350U/mL. After 72 hours of reaction, the conversion rate of the ginsenoside Rb3 is 81.7 percent, the percentage content of notoginsenoside Fd in the product is determined to be 38.5 percent, 133.2g of notoginsenoside Fd is separated and purified and then put in a warehouse, and the purity of the product is 98 percent; the percent content of esculin XIII is 37.4%, 108.8g of the product is separated and purified and then put in storage, and the purity of the product is 98%. The characteristic spectrum is similar to that of figures 3-8.

Claims (9)

1. A method for preparing notoginsenoside Fd and esculin XIII 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 a 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. separation and purification: separating and purifying the hydrolysate to obtain notoginsenoside Fd and esculin XIII.
2. The method for preparing notoginsenoside Fd and esculin XIII according to claim 1, wherein: in the step a, the concentration of the ginsenoside Rb3 solution is 2-50 g/L; preferably, the concentration of the ginsenoside Rb3 solution is 2-10 g/L.
3. The method for preparing notoginsenoside Fd and esculin XIII according to claim 1, wherein: in the step a, the concentration of the cellulase is 10-10000U/mL; preferably, the concentration of the cellulase is 10-4500U/mL.
4. The method for preparing notoginsenoside Fd and esculin XIII according to claim 1, wherein: in the step a, the hydrolysis time is 2-240 hours, preferably 72-120 hours.
5. The method for preparing notoginsenoside Fd and esculin XIII according to claim 1, wherein: in the step a, the cellulase is at least one of Novoxil cellulase, Heshi wall cellulase, Lithocarpus scovifolius pectinase, Xiasangsheng cellulase, Tianye cellulase and Xeno cellulase.
6. The method for preparing notoginsenoside Fd and esculin XIII according to claim 1, wherein: 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 more than 50% with solvent to obtain ginsenoside Rb3 solution.
7. The method for producing notoginsenoside Fd and esculin XIII according to claim 6, 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.
8. The method for producing notoginsenoside Fd and esculin XIII according to claim 7, wherein: the organic solvent is lower alcohol or acetone.
9. The method for preparing notoginsenoside Fd and esculin XIII according to claim 1, wherein: and b, separating and purifying by adopting a gel column chromatography method, a silica gel column chromatography method or an HPLC (high performance liquid chromatography) purification method.
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