CN102559828B - Method for preparing astragaloside IV by converting total saponins of astragalus by microorganisms - Google Patents
Method for preparing astragaloside IV by converting total saponins of astragalus by microorganisms Download PDFInfo
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- CN102559828B CN102559828B CN201010615265.4A CN201010615265A CN102559828B CN 102559828 B CN102559828 B CN 102559828B CN 201010615265 A CN201010615265 A CN 201010615265A CN 102559828 B CN102559828 B CN 102559828B
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- astragaloside
- total saponins
- radix astragali
- cyclosiversioside
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Abstract
The invention discloses a method for preparing astragaloside IV by converting total saponins of astragalus by microorganisms, which comprises the following steps of: preparing bacteria, mould and yeast into bacterium suspension or spore suspension and inoculating the bacterium suspension or the spore suspension into a seed culture medium to form seed solution; then inoculating the seed solution into a fermentation medium to carry out culturing; after the seed solution grows well, adding the total saponins of astragalus to carry out conversion; carrying out scanning and analysis by a TLC (Thin Layer Chromatography) to convert other astragaloside into the astragaloside IV, so that the amount of the astragaloside IV is improved by over four times; and extracting the conversion solution by an organic solvent and separating and purifying the conversion solution by macroporous resin to obtain a pure product of the astragaloside IV. According to the method disclosed by the invention, the defects of damage to the saponins, serious pollution, poor purposiveness and the like in the process of hydrolyzing the total saponins of astragalus by a chemical method can be overcome and the problem of enzyme instability in the process of hydrolyzing the total saponins of astragalus by an enzyme method can be solved. The method has the advantages of no pollution, strong specificity and high conversion rate. The purity of the prepared astragaloside IV can reach over 99.9 percent.
Description
Technical field
The present invention relates to a kind of microbial transformation and prepare the method for Cyclosiversioside F; especially ethanoyl and a glycosyl in the microbial hydrolytic Radix Astragali total saponins that utilization contains deacetylase and Glycosylase, prepare the method for Cyclosiversioside F to improve the microbial transformation Radix Astragali total saponins of Astragaloside content.
Background technology
The Radix Astragali (Radix Astragali) is one of conventional Chinese medicine, is leguminous plants Radix Astragali
astragalus membranaceus(Fischer) Bunge and Radix Astagali
a. membranaceus(Fisch.) Bunge var.
mongholicus(Bunge) dry root of P. K. Hsiao.Cyclosiversioside F (Astragalosides IV, ASI) is from the Radix Astragali, to separate a kind of saponins compound with multiple pharmacologically active obtaining, and is the index components of formulation of astragalus root quality evalution.Studies show that Cyclosiversioside F all has pharmacological action widely in cardiovascular, immune, neural, digestion, uropoiesis, circulation and endocrine system etc., it is reported, Cyclosiversioside F can alleviate the hemato encephalic barrier perviousness increase that cerebral ischemia re-pouring causes; Ischemic brain injury is had to provide protection; By regulating the expression performance antitumour activity of oncogene; Diabetic mice is had to hypoglycemic activity; There is strong anti-hepatitis B virus activities; Can effectively suppress or reverse the hepatic fibrosis of the mouse model of PS induction; Its Chinese medicine preparation is developed to the treatment of myocardial protective agent for coronary heart disease and angina pectoris.But practice show, Cyclosiversioside F content in the Radix Astragali is extremely low, and be subject to the place of production and seasonal effect larger, be generally about 0.04%, extract separation difficulty.
Radix Astragali total saponins (Astragalosides, AST) is the main effective constituent of the Radix Astragali, accounts for the 2-3% of Radix Astragali dry weight.AST is a series of ring A Er front yard alkane type triterpenoid glycosides, and its chemical structure is as figure below:
| ? | R1 | R2 | R3 |
| astragaloside IV | β-D-xylp | β-D-glcp | H |
| astragaloside I | β-D-xylp(2’3’-di-OAc) | β-D-glcp | H |
| astragaloside II | β-D-xylp(2’-OAc) | β-D-glcp | H |
| astragaloside VI | β-D-xylp-2’-β-D-glcp | β-D-glcp | H |
| astragaloside VII | β-D-xylp | β-D-glcp | β-D-glcp |
| Acetylastragaloside I | β-D-xylp(2’3’4'-tri-OAc) | β-D-glcp | H |
| isoastragaloside I | β-D-xylp(2'4'-di-OAc) | β-D-glcp | H |
| isoastragaloside II | β-D-xylp(3’-OAc) | β-D-glcp | H |
| agroastragaloside III | β-D-xylp(2’3’-di-OAc) | β-D-glcp | H |
| agroastragaloside IV | β-D-xylp(2’-OAc) | β-D-glcp | β-D-glcp |
| Cycloglobiceposide A | β-D-xylp(2’-OAc) | β-D-glcp(6’-OAc) | H |
Different Radix Astragali saponin structural difference are mainly 3-, the glycosyl kind of 6-and 25-position and the difference of quantity, the i.e. ASI wherein of Cyclosiversioside F.Analyze from structure that unnecessary ethanoyl is removed in the hydrolysis of other Radix Astragali saponins or glycosyl all can be converted into Cyclosiversioside F.The main content that adopts chemical method and enzyme process Radix Astragali total saponins to be hydrolyzed to improve Cyclosiversioside F, increases the extraction yield that extracts Cyclosiversioside F from Chinese medicinal materials at present.
The content that how to improve Cyclosiversioside F is just causing the concern about investigator.
Summary of the invention
The object of the invention is the technical problem that Astragaloside content is low, separation and Extraction is difficult existing in prior art for solving, a kind of method of preparing Cyclosiversioside F by microbial transformation Radix Astragali total saponins is provided, especially utilizing other saponin(es in microbial transformation Radix Astragali total saponins is Cyclosiversioside F, and from microbial fermentation solution the method for separation and purification Cyclosiversioside F.
The inventive method can improve Astragaloside content, for solving the source of Cyclosiversioside F, further develops Chinese medicine astragalus and lays the foundation.
Particularly, the method for preparing Cyclosiversioside F by microbial transformation Radix Astragali total saponins of the present invention, is characterized in that, it comprises step:
Microbial strains is made to bacteria suspension or spore suspension, be inoculated in seed culture medium, 28 DEG C, 220 rpm cultivate 24 ~ 48 h obtain seed liquor, again seed liquor is inoculated in fermention medium, 28 DEG C, 220 rpm cultivation 24 ~ 48 h, drop into Radix Astragali total saponins, under the same terms, transform 48 ~ 96 h, obtain conversion fluid; Other Radix Astragali saponins of TLC scanning analysis are converted into Cyclosiversioside F, and the amount of Cyclosiversioside F is improved more than 3 times.
In the present invention, the conversion fluid obtaining, can be by organic solvent extraction and macroporous resin separation and purification Cyclosiversioside F, optimum means of purification is first to adopt alcohol immersion, use again n-butanol extraction, gained medicinal extract adopts the separation and purification of D101 macroporous resin again, after ethyl acetate extraction, obtains purity astragaloside.In embodiments of the invention, by 95% industrial alcohol soaked overnight for above-mentioned fermented liquid, thalline and precipitation are removed in centrifuging, and rotary evaporation, to without ethanol taste, is used twice of n-butanol extraction.Merge organic layer, be spin-dried for, propyl carbinol reclaims.Gained medicinal extract redissolves with methyl alcohol, filters, and removes precipitation.After filtrate is spin-dried for, with the separation and purification of D101 macroporous resin, first with the pre-eccysis sugar of distilled water, wash away a large amount of pigments with the 2%KOH aqueous solution again, then use successively 19% ethanol, 23.75% ethanol, 47.5% ethanol and 57% ethanol elution, TLC follows the tracks of detection, merge containing Cyclosiversioside F component rotary evaporation, extremely without ethanol, remaining liq is extracted with ethyl acetate once, being spin-dried for after ethyl acetate remaining in water layer is adularescent Precipitation, centrifugal 10 min of 10000 r/min, obtain purity astragaloside, the rate of recovery reaches more than 82%, Cyclosiversioside F chromatographic purity reaches 99.9%.
In the present invention, described microorganism is selected from bacterium, mould or yeast; Preferred absidia corymbifera in embodiments of the invention (
absidia corymbifera, purchased from Shanghai City Industry Wei Biological Research Institute).
In the present invention, ethanoyl and glycosyl in the microbial hydrolytic Radix Astragali total saponins that described microbial transformation Cyclosiversioside F mainly contains deacetylase and Glycosylase by utilization, improve Astragaloside content.
In the present invention, described Radix Astragali total saponins, its composition comprises all or part of Radix Astragali saponin monomer, as astragaloside I, II, VI, VII, isoastragaloside I, II, acetylastragaloside I, agroastragaloside III, IV, Cycloglobiceposide A etc.
Feature of the present invention is using microbe method for transformation, other Radix Astragali saponins in Radix Astragali total saponins are converted into Cyclosiversioside F, in described microbial transformation, utilize the substrate for enzymatic activity producing in microbial metabolism to carry out chemical reaction, because its regio-and stereo-selectivity is strong, can carry out multistep enzymatic reaction simultaneously, reaction conditions gentleness, easy and simple to handle, cost be compared with low, the few industrial production that is suitable for of public hazards.Present method can overcome the shortcomings such as chemical method hydrolysis for astragalus total saponins existence saponin(e is destroyed reaches, seriously polluted, purpose is poor, and enzyme instability problem in enzymatic hydrolysis Radix Astragali total saponins process.Have advantages of pollution-free, specificity is strong, transformation efficiency is high, the Cyclosiversioside F purity of preparation is more than 99.9%.
The present invention is in order to check the practicality of prepared Cyclosiversioside F, and adopting ethanol and propylene glycol, as non-aqueous solvent and solubility promoter, described Cyclosiversioside F is made to 1 mg/mL specification is the astragaloside injection of 2 mL.
In described injection liquid, preferred ingredient is: as non-aqueous solvent and solubility promoter, Cyclosiversioside F 1 g, ethanol 200 mL, propylene glycol 200 mL, glucose 100 g, supply water for injection to 1000 mL by ethanol and propylene glycol.
The Cyclosiversioside F that the present invention makes, can also make pharmaceutically acceptable preparation, as tablet, injection, suppository, external preparation etc.Can be for the treatment of cardiovascular disorder, cerebrovascular disease, anticancer, antiviral, diabetes etc.
The invention provides the therepic use of described astragaloside injection at aspects such as cardiovascular and cerebrovascular diseases, antiviral and diabetes.Be particularly useful for the treatment of viral myocarditis.
Brief description of the drawings
Fig. 1 is fermented liquid TLC analysis chart in the present invention,
Wherein, the 1st, Radix Astragali total saponins, the 2nd, fermented liquid, the 3rd, contrast (bacterium liquid does not feed intake), the 4th, Cyclosiversioside F standard substance;
Fig. 2 is the each step TLC analysis chart of Cyclosiversioside F separation and purification in the present invention,
Wherein, the 1st, raw material Radix Astragali total saponins, the 2nd, fermented liquid n-butanol extract, the 3rd, after macroporous resin separates, the 4th, the purity astragaloside obtaining, the 5th, Cyclosiversioside F standard substance;
Fig. 3 is the each step HPLC chromatographic purity of Cyclosiversioside F separation and purification analysis chart in the present invention,
Wherein, A is n-butanol extract (chromatographic purity 35.9%), and B is that D101 macroporous resin separates (chromatographic purity 61.98%), and C is purity astragaloside (chromatographic purity 99.9%).
Embodiment
Embodiment 1: utilize
absidia corymbiferatransform Radix Astragali total saponins and prepare Cyclosiversioside F
Two absidia corymbiferas (
absidia corymbifera) test tube slant, add 50 mL sterilized waters and make spore suspension, be inoculated in the 250 mL shaking flasks that (every bottle of 1 mL) be equipped with 50 mL liquid nutrient mediums, liquid nutrient medium is potato culture (200 g potatos, 1 L that adds water, boil half an hour, remove by filter residue, in filtrate, add 20 g glucose, natural pH).28 DEG C, 220 rpm, cultivate 24 h, obtain seed liquor.250 mL seed liquor are inoculated in the 5 L fermentation flasks that 1 L aforesaid liquid substratum is housed, 28 DEG C, 220 rpm, cultivate 24 h, drop into crude product Radix Astragali total saponins (concentration that feeds intake 10 g/L), transform 72 h under the same terms.Fermented liquid TLC analytical results is shown in Fig. 1,
absidia corymbiferaother Radix Astragali saponins in Radix Astragali total saponins can be converted into Cyclosiversioside F.
Fermented liquid adds 1 L 95% industrial alcohol soaked overnight, and thalline and some precipitations are removed in centrifuging, rotary evaporation to 300 mL left and right (without ethanol taste), with 100 mL n-butanol extractions once, 50 mL propyl carbinols extract once again.Merge organic layer, be spin-dried for, propyl carbinol reclaims.Gained medicinal extract redissolves with methyl alcohol, filters, and removes precipitation, and filtrate is spin-dried for for subsequent use.In TLC scanning analysis filtrate, Astragaloside content is 129.8 mg, and it is 35.9% that HPLC analyzes chromatographic purity.In raw material Radix Astragali total saponins, Astragaloside content is 34.5 mg, and after microbial transformation, the amount of Cyclosiversioside F improves approximately 3 times.
Above-mentioned filtrate is used D101 macroporous resin (j20 * 250mm) separation and purification, loading flow velocity 0.6ml/min, first use the pre-eccysis sugar of 5 BV distilled water, wash away a large amount of pigments with the 5 BV 2%KOH aqueous solution again, then use successively 4BV 19% ethanol, 2BV 23.75% ethanol, 2BV 47.5% ethanol and 10BV 57% ethanol elution, TLC follows the tracks of detection, merge 47.5% cut and 57% cut rotary evaporation, extremely without ethanol, the about 340ml of remaining liq, carry out thin layer scanning and obtain Cyclosiversioside F 126.6 mg, the rate of recovery 97.5%, chromatographic purity is 61.98%.
Aforesaid liquid extracts once by 40ml ethyl acetate, is spin-dried for ethyl acetate remaining in water layer, adularescent Precipitation in water, and centrifugal 10 min of 10000 r/min, obtain Cyclosiversioside F white solid 107.6 mg, the rate of recovery 82.9%, chromatographic purity 99.9%.
The each step TLC of separation and purification analyzes and sees Fig. 2, and Fig. 3 is shown in the analysis of HPLC chromatographic purity.
Embodiment 2: astragaloside injection preparation
Prescription: Cyclosiversioside F 1.0 g
Glucose 100 g
Water for injection complements to 1000 mL
Preparation method: the Cyclosiversioside F of getting recipe quantity, at 40 DEG C, be dissolved in the ethanol of recipe quantity and the mixing solutions of propylene glycol, stir and add part water for injection, add again the glucose of recipe quantity, after dissolving completely, supply water for injection to 1000 mL, 0.22 μ m strainer filters, embedding, sterilizing, obtains 200 of 2 mL specification astragaloside injections.
1 experiment purpose adopts coxsackie B
3virus (CVB
3) infect the murine viral myocarditis model causing, astragaloside injection prepared by the evaluation the present invention therapeutic action to viral myocarditis, provides experimental basis for treating viral myocarditis new drug development and clinical application.
Cyclosiversioside F is divided into two dosage groups by 2 experimental techniques, and 50 of Balb/c mouse are divided into 4 groups at random.Normal group (5): do not give Cyclosiversioside F, not virus inoculation, only gives equivalent solvent; Virus control group (15): every intraperitoneal inoculation 0.1 mL CVB
3virus liquid (TCID
50=10
-7.5, 10
5doubly dilution); Administration group I---high dosage (15): the same method inoculation CVB
3virus liquid, tail vein injection astragaloside injection 3 mg/kg on the same day, successive administration 7 d, observe 15 d; Administration group II---low dosage (15): with administration group I method, tail vein injection astragaloside injection, dosage is 1 mg/kg.
Adopt the dosage grouping of above-mentioned test, successive administration 7 d, observe after 15 d, the M & M of more each papova myocarditis mouse, and dissect mouse, calculate cardiac index, record heart change degree, do pathological section, inverted phase contrast microscope is observed heart change.
3 experimental results
3.1 impacts on mice with viral myocarditis M & M
The mental status, diet, hair color and the death condition of the each treated animal of observed and recorded during administration (raising).Result shows that two dosage groups of medicine of the present invention all can significantly reduce by coxsackie B
3virus (CVB
3) infect the M & M of the mice with viral myocarditis causing, in table 1.
The impact of table 1 medicine of the present invention on mice with viral myocarditis M & M
| Group | Number of animals (only) | Sickness rate (number of cases) | Mortality ratio (number of cases) |
| Normal group | 5 | 0（0） | 0（0） |
| |
15 | 86.67%（13） | 33.33%（5） |
| High |
15 | 40.0%（6） | 6.67%（1） |
| Low |
15 | 53.33%(8) | 13.33%（2） |
Note: adopt chi square test, administration group compares with virus group.
3.2 impacts on mice with viral myocarditis cardiac index
Test the 15th day, mouse is all dissected.Before dissection, take Mouse Weight, after dissection, take again its cardiac weight, be calculated as follows cardiac index:
Cardiac index=heart weight/body weight
Animal by virus infection after, food ration reduce, weight loss, and heart therefore expand, there is fibrosis and become weight, so can weigh with cardiac index the lesion degree of heart, cardiac index is larger, heart change is more serious.
Result shows that the high dose group of medicine of the present invention can significantly reduce by coxsackie B
3virus (CVB
3) infect the cardiac index of the mice with viral myocarditis causing, in table 2.
The impact of table 2 medicine of the present invention on mice with viral myocarditis cardiac index
| Group | Cardiac index (× 10 -3） |
| Normal group | 4.66±0.72 |
| Virus control group | 6.53±1.21 |
| High dosage administration group | 5.47±0.83** |
| Low dosage administration group | 6.24±0.94 |
Note: administration group compares with virus group, * * P<0.01.
3.3 impacts on the apparent lesion degree of mice with viral myocarditis heart
Test the 15th day, mouse is all dissected.The heart change degree that record is observed, mainly determines from size and the heart degree of expanding of patch shape pathology, is divided into 0 ,+, ++, +++, ++++Pyatyi, lesion degree increases the weight of successively.
Result shows that two dosage groups of medicine of the present invention all can significantly reduce by coxsackie B
3virus (CVB
3) infect the apparent lesion degree of heart of the mice with viral myocarditis causing, as shown in table 3.
The impact of table 3 medicine of the present invention on the apparent lesion degree of mice with viral myocarditis heart
| ? | 0 | + | ++ | +++ | ++++ | Mean value |
| Control group | 5 | 0 | 0 | 0 | 0 | 0 |
| Virus group | 0 | 2 | 6 | 4 | 3 | 2.4 |
| High dosage administration group | 9 | 3 | 2 | 1 | 0 | 0.7** |
| Low |
4 | 3 | 7 | 1 | 0 | 1.3** |
Note: administration group compares with virus group, * * P<0.01.
3.4 impacts on myocardial tissue of mice with viral myocarditis cellular infiltration and degree of necrosis
Test the 15th day, mouse is all dissected.Take out heart, put in formalin solution, observe after doing pathological section under inverted phase contrast microscope, each sample is observed 5 high power fields, and record infiltrates and and downright bad situation.Each visual field, pathology 0 ~ 25% is designated as 1,25% ~ 50% and is designated as 2,50% ~ 75% and is designated as 3,75% ~ 100% and is designated as 4.
Result shows that two dosage groups of medicine of the present invention all can significantly improve by coxsackie B
3virus (CVB
3) infect the heart change situation of the mice with viral myocarditis that causes.
The impact of table 4 medicine of the present invention on myocardial tissue of mice with viral myocarditis cellular infiltration and degree of necrosis
| Group | Infiltrate | Downright bad |
| Normal group | 0 | 0 |
| Virus control group | 1.9±0.61 | 2.2±0.43 |
| High dosage administration group | 0.7±0.55** | 1.3±0.58** |
| Low dosage administration group | 1.1±0.72** | 1.6±0.41** |
Note: administration group compares with virus group, * * P<0.01.
Claims (3)
1. a method of preparing Cyclosiversioside F by microbial transformation Radix Astragali total saponins, is characterized in that, it comprises step:
Microbial strains is made to bacteria suspension or spore suspension, be inoculated in seed culture medium, 28 DEG C, 220rpm are cultivated 24～48h and are obtained seed liquor, again seed liquor is inoculated in fermention medium, 28 DEG C, 220rpm are cultivated 24～48h, drop into Radix Astragali total saponins, under the same terms, transform 48～96h, obtain conversion fluid; Conversion fluid obtains purity astragaloside by organic solvent extraction and macroporous resin separation and purification;
Described Radix Astragali total saponins, its composition comprises Radix Astragali saponin monomer: astragaloside I, II, VI, VII, isoastragaloside I, II, acetylastragaloside I, agroastragaloside III, IV and/or Cycloglobiceposide A;
Described microorganism is absidia corymbifera (Absidia corymbifera).
2. by method claimed in claim 1, it is characterized in that, described microbial transformation Cyclosiversioside F is ethanoyl and the glycosyl in the microbial hydrolytic Radix Astragali total saponins by containing deacetylase and Glycosylase, improves Astragaloside content.
3. by method claimed in claim 1, it is characterized in that, described conversion fluid, by organic solvent extraction and macroporous resin separation and purification Cyclosiversioside F, or first adopt alcohol immersion, use n-butanol extraction, gained medicinal extract adopts the separation and purification of D101 macroporous resin more again, after ethyl acetate extraction, obtains purity astragaloside.
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| CN103305572B (en) * | 2013-05-31 | 2014-12-24 | 西昌丹阳生物科技有限责任公司 | Method for producing baohuoside I through herba epimdii |
| CN104711312B (en) * | 2015-03-15 | 2018-02-23 | 北京化工大学 | The method that Astragaloside IV is prepared using Trichoderma viride |
| CN105481934A (en) * | 2015-12-02 | 2016-04-13 | 上海景峰制药有限公司 | Astragaloside bulk drug and preparation method thereof |
| CN105541954A (en) * | 2015-12-02 | 2016-05-04 | 上海景峰制药有限公司 | Radix astragali extract with high purity astragaloside |
| CN105861614B (en) * | 2016-05-12 | 2020-08-04 | 中国农业科学院农业资源与农业区划研究所 | Application of aspergillus niger in preparation of astragaloside |
| CN111705097A (en) * | 2020-06-30 | 2020-09-25 | 山东康裕生物科技有限公司 | Purification process of radix astragali for animal feed additive |
| CN112057499A (en) * | 2020-08-20 | 2020-12-11 | 武汉自在生物科技有限公司 | Preparation method of antitumor drug |
| CN114748490B (en) * | 2022-04-24 | 2023-12-12 | 南方科技大学 | Pharmaceutical composition for treating premature ovarian failure, application and preparation method thereof |
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| CN1923211A (en) * | 2005-09-02 | 2007-03-07 | 天津药物研究院 | Astragaloside injection and preparation thereof |
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| CN1923211A (en) * | 2005-09-02 | 2007-03-07 | 天津药物研究院 | Astragaloside injection and preparation thereof |
| CN101130802A (en) * | 2007-07-30 | 2008-02-27 | 金凤燮 | Method for preparing astragaloside iv by enzymic hydrolysis for astragalus saponin glycosyl |
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