CN115216511B - Method for preparing rare saponin by fermenting and converting notoginsenoside R1 with lactobacillus plantarum - Google Patents
Method for preparing rare saponin by fermenting and converting notoginsenoside R1 with lactobacillus plantarum Download PDFInfo
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Abstract
The invention discloses a method for preparing rare saponin by fermenting and converting panax notoginseng saponins R1 by lactobacillus plantarum, relates to the technical field of probiotic fermentation, and provides a method for preparing rare saponin. The invention relates to lactobacillus plantarum (A)Lactiplantibacillus plantarum) S165, preserving in China center for type culture Collection, with the preservation address: wuhan university in Wuhan City, china, the preservation date: 2022, 06/02, accession No.: CCTCC NO: M2022783. Used for preparing rare saponin. The invention screens 1 strain of lactobacillus new strain which can convert notoginsenoside R1 into notoginsenoside T5 and isomers thereof by fermentation, and the method has the advantages of safety, high efficiency, low cost and the like. The prepared rare saponin has wide application and wide application prospect. The invention is applied to the field of saponin preparation.
Description
Technical Field
The invention relates to the technical field of probiotic fermentation, in particular to a method for preparing rare saponin by fermenting and converting notoginsenoside R1 with lactobacillus plantarum.
Background
Notoginseng radixPanax notoginseng(Burk.) F.H. Chen is a plant of Araliaceae, uses dry root and rhizome as medicine, is called Shangeng and jin Bu, is a traditional precious Chinese medicine in China, and has the functions of nourishing, strengthening, enriching blood, reducing swelling, easing pain, stopping bleeding, dispersing nodules and the like. The saponin is Notoginseng radixThe three saponins with the highest contents are respectively notoginsenoside R1, ginsenoside Re and ginsenoside Rg1. Pharmacological research shows that the saponins have good pharmacological activity for preventing and treating cardiovascular and cerebrovascular diseases, and in addition, have the functions of reducing blood fat, reducing blood sugar, reducing blood pressure, resisting inflammation, resisting fatigue, resisting anoxia, resisting aging, improving the immunity of the organism and the like.
At present, a lot of researches on structural transformation methods of saponin components in pseudo-ginseng roots are carried out, wherein the methods comprise acid hydrolysis, microwave-assisted degradation and the like, the transformation specificity of the methods is low, the reaction is severe, and a reaction solution causes a lot of pollution to the environment and is not beneficial to industrial production. The ginsenoside Rh1 and ginsenoside Rg can be obtained from the experiment by the scholars performing biotransformation on the panax notoginseng root total saponins by using microorganisms such as bacteria and fungi, such as aspergillus niger, streptomyces and eurotium cristatum 3 Rare ginsenosides such as ginsenoside CK and the like, but the safety of the strains is uncertain, wherein pathogenic bacteria harmful to human bodies are not lacked, and the safety of the product is obviously reduced.
At present, reports of preparing rare saponins, in particular notoginsenoside T5 and isomers thereof by adopting lactobacillus fermentation and transformation are lacked.
Disclosure of Invention
The invention aims to provide a method for preparing notoginsenoside T5 and isomers thereof by fermenting and converting notoginsenoside R1 by using lactobacillus plantarum, so that the method can obtain high-content rare notoginsenoside T5 and isomers thereof by taking the notoginsenoside R1 extracted from pseudo-ginseng roots as a raw material.
The invention relates to a method for preparing rare saponin by fermenting and converting notoginsenoside R1 with lactobacillus plantarum, which comprises the following steps:
step one, preparation of bacterial suspension
Mixing Lactobacillus plantarum (A)Lactiplantibacillus plantarum) S165, inoculating the strain in a liquid MRS culture medium, standing and culturing for 16-25 h at the temperature of 37-45 ℃, and then centrifugally collecting bacterial precipitates; sterilizing water suspension precipitation to make viable count 1.0 × 10 9 ～1.0×10 10 CFU/mL to obtain a bacterial suspension;
step two,
Inoculating 10-30mL of the bacterial suspension obtained in the first step into each 1L of liquid fermentation medium, and standing and fermenting for 7-14 days at the temperature of 37-42 ℃; after fermentation, concentrating the fermentation product under reduced pressure, freeze drying, extracting the dried product with methanol, centrifuging, recovering solvent from the supernatant under reduced pressure, and freeze drying to obtain notoginsenoside T5 and its isomer;
the liquid fermentation culture medium consists of glucose with the concentration of 20-50 g/L, yeast extract powder with the concentration of 10-30 g/L and notoginsenoside R1 with the concentration of 1-5g/L, and the pH is =6.0-7.0;
the Lactobacillus plantarum (A), (B)Lactiplantibacillus plantarum) S165, preserving in China center for type culture Collection, with the preservation address: wuhan university in Wuhan City, china, the preservation date: 2022, 06/02, accession No.: CCTCC NO: M2022783.
Further, the centrifugation conditions in step one are: centrifuging at 4000-8000 rpm for 5-10 min.
Further, the decompression concentration of the fermentation product in the second step is decompression concentration at 70 ℃.
Further, the centrifugation in the second step is performed for 15min at the temperature of 4 ℃ and the rotation speed of 10000 rpm.
The lactobacillus plantarum of the invention is lactobacillus plantarum (A)Lactiplantibacillus plantarum) S165, preserving in China center for type culture Collection, with the preservation address: wuhan university in Wuhan City, china, the preservation date: 2022, 06/02, accession No.: CCTCC NO: M2022783.
The lactobacillus plantarum is used for preparing notoginsenoside T5 and isomers thereof.
Further, the lactobacillus plantarum is used for preparing notoginsenoside T5 and isomers thereof, and the preparation of the notoginsenoside T5 and the isomers thereof is obtained by fermenting and converting notoginsenoside R1 into notoginsenoside T5 and isomers thereof.
The microbial inoculum obtained by the lactobacillus plantarum and used for preparing the notoginsenoside T5 and the isomers thereof is provided.
Lactic acid bacteria are a safe food-grade microorganism, and secondary metabolites such as glucosidase, rhamnosidase and xylosidase can be produced in the growth process, and the metabolites can be degraded by cutting off various glycosidic bonds of ginsenoside, so that the purpose of changing the chemical structure of the ginsenoside is achieved. And because different types of glycosidases metabolized by different lactic acid bacteria have different specificities for structural modification of ginsenoside, and obvious structure-activity relationship exists between rare saponin with different chemical compositions and biological activity. Based on the research findings, the invention obtains a lactobacillus plantarum strain through screeningLactiplantibacillus plantarum) S16, and the application of the compound in fermentation conversion research of notoginsenoside achieves remarkable effect.
The invention has the following beneficial effects:
lactobacillus plantarum (A) of the present inventionLactiplantibacillus plantarum) S165 has the characteristic of high yield of beta-glucosidase, so that the notoginsenoside R1 can be effectively converted into notoginsenoside T5 and isomers thereof through fermentation and conversion.
The invention screens and obtains 1 new lactobacillus strain which can ferment and convert notoginsenoside R1 into notoginsenoside T5 (NG-T5) and isomers (NG-T5 isomer), identifies the strain, determines the process for preparing rare notoginsenoside by fermenting and converting the strain, and identifies the converted rare notoginsenoside by an HPLC method and an LC/MC method. The method has the advantages of safety, high efficiency, low cost, etc. The prepared rare notoginsenoside has wide application and wide application prospect.
Drawings
FIG. 1 is HPLC chromatogram of notoginsenoside R1 standard;
FIG. 2 is HPLC chromatogram of notoginsenoside T5 standard;
FIG. 3 is an HPLC chromatogram of notoginsenoside T5 (NG-T5) and its isomer (NG-T5 isomer) produced by fermenting notoginsenoside R1 with Lactobacillus plantarum; in the figure, a is a notoginsenoside T5 (NG-T5) peak, b is a notoginsenoside T5 isomer (NG-T5 isomer) peak;
FIG. 4 is a schematic diagram of the biotransformation synthesis route of rare notoginsenoside.
Detailed Description
For the purpose of promoting a clear understanding of the objects, aspects and advantages of the embodiments of the invention, reference will now be made in detail to the embodiments of the present disclosure, and it will be apparent to one skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope of the disclosure.
The exemplary embodiments and descriptions of the present invention are provided to explain the present invention and should not be interpreted as limiting the present invention.
EXAMPLE 1 isolation, identification and preservation of the Strain
1. Isolation of the Strain
Samples and sources for isolation of strains: and 6, collecting northeast naturally fermented pickled Chinese cabbage samples in 2018 in 6 months. Grinding the collected sample, diluting in gradient, coating on lactobacillus selective solid culture medium plate, culturing at 37 deg.C for 48h, picking typical colony (milky white, round, neat edge, convex, opaque, and smooth surface), streak-culturing MRS agar plate, and separating to obtain pure colony. Inoculating the pure cultured strain to a liquid MRS culture medium for culture, and adding 60% glycerol for refrigerator preservation at-80 ℃. Among them, 1 strain of Lactobacillus was designated as S165.
2. Identification of strains
Physiological and biochemical identification results of S165: gram staining is positive, catalase test is negative, benzidine test is negative, indole test is negative, and acetyl methyl methanol test is positive; starch is not hydrolyzed, gelatin is not liquefied, hydrogen sulfide is not generated, and acid and gas are not generated by fermenting glucose; an immotile bacillus; can grow at 15 ℃ and 45 ℃, and the optimal growth temperature is 37-42 ℃; the pH is suitably 5.0 to 7.0; tolerates 6.5% NaCl; s165 grows in a uniform turbid manner in a liquid MRS culture medium, and thalli are white and precipitated after being placed for a long time.
In the above table, "+" indicates that the strain is a positive reaction; "-" indicates that the strain was negative.
Amplifying and comparing 16S rDNA gene sequences. Extracting genome DNA by a CTAB method, respectively designing 16S rDNA primers according to conserved regions of gene sequences, carrying out PCR amplification and product sequencing, and carrying out homology comparison analysis on the obtained 16S rDNA sequences of the strains and sequence information of known strains in a GenBank database through BLAST to identify the strains to be detected; the species were classified based on the 16S rDNA sequence homology of more than 99%. Homology analysis of the 16S rDNA sequence with the GenBank database (GenBank accession: GENBANK/AJ 965482) by BLAST program revealed that S165 has a homology of more than 99% to Lactobacillus plantarum.
From the above results, the strain S165 was identified as Lactobacillus plantarum (Lactiplantibacillus plantarum）。
3. Preservation of the Strain
The Lactobacillus plantarum (A) of the present inventionLactiplantibacillus plantarum) S165, which has been preserved in China Center for Type Culture Collection (CCTCC) at 06/02/2022, addresses: wuhan university in Wuhan City, china, preservation date: 2022, 06/02, accession No.: CCTCC NO: M2022783.
Example 2 Lactobacillus plantarum: (Lactiplantibacillus plantarum) Detection of S165 glycosidase Activity
Lactobacillus plantarum (A), (B), (C)Lactiplantibacillus plantarum) S165 is inoculated in a liquid MRS culture medium, is subjected to static culture for 169h at 37 ℃, is centrifuged for 8min at 6000rpm at 4 ℃, and is collected to be used as a sample for enzyme activity detection.
And (3) measuring the hydrolysis rate of p-nitrobenzene-beta-D-glucoside (pNPG) by using an enzyme analysis kit. 5mM pNPG was prepared using 100mM PBS (pH 7.0), and 500. Mu.L of each was pipetted and added to 5mL of the sample, and after incubation at 37 ℃ for 30min, the reaction was stopped by adding 250. Mu.L of cold 0.2M sodium carbonate (4 ℃), centrifuged at 14000 Xg for 30min with an Eppendorf centrifuge, and filtered through a 0.45 μ M membrane filter. The amount of p-nitrophenol released was measured with a spectrophotometer at 420 nm. The ability to produce 1. Mu. Mol of p-nitrophenol from substrate hydrolysis per ml per minute is defined as one unit of enzyme activity.
TABLE 2 Lactobacillus plantarum: (Lactiplantibacillus plantarum) S165 glycosidase Activity
Example 3 preparation of rare saponins of the invention
1. Lactobacillus plantarum (A), (B), (C)Lactiplantibacillus plantarum) Preparation of S165 bacterial suspension
Lactobacillus plantarum: (A)Lactiplantibacillus plantarum) S165 (hereinafter, all are referred to as S165) is inoculated in a liquid MRS medium (purchased), kept stand and cultured at 37 ℃ for 169h, centrifuged at 6000rpm for 8min at 4 ℃, thallus precipitate is collected, suspended by a fermentation sterilization medium aqueous solution, and the viable count is adjusted to 1.0 multiplied by 10 9 CFU/ml, obtaining S165 bacterial suspension.
Notoginsenoside R1 (HPLC ≥ 98%) was purchased from Chengdu Egyang method Biotechnology limited.
The fermentation conversion method comprises the following steps: the liquid fermentation culture medium comprises 30g/L glucose, 10g/L yeast extract powder, pH6.6, and sterilizing at 121 deg.C for 15min. Adding 1g/L notoginsenoside R1 in liquid culture medium, inoculating 10ml/L Lactobacillus plantarum suspension, standing at 37 deg.C, and fermenting for 14 days. After the fermentation, the fermentation product was concentrated at low temperature (70 ℃) under reduced pressure, freeze-dried, the dried product was extracted with methanol, centrifuged (10000rpm, 15min,4 ℃), and the supernatant was subjected to pressure reduction to recover the solvent, followed by freeze-drying.
Example 4 identification of rare Saponin T5 of Panax notoginseng of the present invention
1. Detecting rare notoginsenoside by HPLC:
lyophilizing the fermentation broth of notoginsenoside R1, dissolving in methanol, filtering with 0.22 μm microporous membrane, and analyzing with chromatography.
HPLC chromatographic method: the chromatographic column is an Agilent pursuit5 SB-C18 chromatographic column, the sample volume is 20 mu L, the flow rate is 1mL/min, the column temperature is 30 ℃, and the detection wavelength is 203nm. The mobile phase is A: water, B: acetonitrile, 0 to 40min, 18 to 21% (B); 40 to 42min 21 to 26 percent (B); 42 to 46min 26 to 32% (B); 46 to 66min 32 to 34 percent (B); 66 to 71min 34 to 38% (B); 71 to 77.70min 38.0 to 49.1 percent (B); 77.70 to 82min 49.1 percent (B); 82 to 83min 49.1 to 50.6 percent (B); 83 to 88min 50.6 to 59.6 percent (B); 88 to 89.80min 59.6 to 65.0% (B); 89.80 to 97min 65% (B); 97 to 102min 65 to 75 percent (B); 102 to 110min, 75 to 85 percent (B); 110 to 115min 85 percent (B); 115 to 125min 85 to 18 percent (B); 125 to 130min 18.0 percent (B).
Notoginsenoside R1 and T5 standard are shown in figures 1 and 2 respectively. HPLC chromatogram of notoginsenoside T5 (NG-T5) and its isomer (NG-T5 isomer) generated after fermentation of notoginsenoside R1 is shown in FIG. 3. The rare notoginsenoside biotransformation synthesis route is shown in figure 4, notoginsenoside R1 is hydrolyzed under the action of glucosidase generated by lactobacillus plantarum S165 to generate notoginsenoside R2, and then notoginsenoside T5 (NG-T5) and an isomer (NG-T5 isomer) thereof are further transformed. The retention time of notoginsenoside T5 (NG-T5) under the HPLC chromatographic condition is consistent with that of a standard product, the molecular weights of compounds are 751.46 as the result of mass spectrometry analysis of notoginsenoside T5 (NG-T5) and isomers (NG-T5 isomer), and the results confirm that notoginsenoside R1 is fermented and converted by lactobacillus plantarum S165 to generate rare saponin notoginsenoside T5 (NG-T5) and isomers (NG-T5 isomer).
Claims (8)
1. A method for preparing rare saponin by fermenting and converting notoginsenoside R1 by lactobacillus plantarum is characterized in that the rare saponin is notoginsenoside T5 and isomers thereof, and the method specifically comprises the following steps:
step one, preparation of bacterial suspension
Mixing Lactobacillus plantarum (A)Lactiplantibacillus plantarum) S165, inoculating the strain in a liquid MRS culture medium, standing and culturing for 16-25 h at the temperature of 37-45 ℃, and then centrifugally collecting bacterial precipitates; sterilizing water suspension precipitation to make viable count 1.0 × 10 9 ～1.0×10 10 CFU/mL to obtain bacterial suspension;
step two, inoculating 10-30mL of the bacterial suspension in the step one into each 1L of liquid fermentation medium, and standing and fermenting for 7-14 days at the temperature of 37-42 ℃; after fermentation, concentrating the fermentation product under reduced pressure, freeze drying, extracting the dried product with methanol, centrifuging, recovering solvent from the supernatant under reduced pressure, and freeze drying to obtain notoginsenoside T5 and its isomer;
the chemical structural formula of the notoginsenoside T5 is as follows:
the chemical structural formula of the notoginsenoside T5 isomer is as follows:
the liquid fermentation culture medium consists of glucose with the concentration of 20-50 g/L, yeast extract powder with the concentration of 10-30 g/L and notoginsenoside R1 with the concentration of 1-5g/L, and the pH is =6.0-7.0; the lactobacillus plantarum (A), (B), (C)Lactiplantibacillus plantarum) S165, preserving in China center for type culture Collection, with the preservation address: wuhan university in Wuhan City, china, the preservation date: 2022, 06/02, accession No.: CCTCC NO: M2022783.
2. The method for preparing rare saponin by fermenting and transforming notoginsenoside R1 by lactobacillus plantarum according to claim 1, wherein the centrifugation conditions in the first step are as follows: centrifuging at 4000-8000 rpm for 5-10 min.
3. The method for preparing rare saponins by fermenting and transforming notoginsenoside R1 by using Lactobacillus plantarum according to claim 1, wherein the reduced pressure concentration of the fermentation product in the second step is reduced pressure concentration at 70 ℃.
4. The method for preparing rare saponin by fermenting and transforming notoginsenoside R1 with lactobacillus plantarum as claimed in claim 1, wherein the centrifugation in step two is performed at 10000rpm at 4 ℃ for 15min.
5. A plant lactobacillus is characterized in that the plant lactobacillus is plant lactobacillus (Lactobacillus plantarum) ((Lactiplantibacillus plantarum) S165, preserving in China center for type culture Collection, with the preservation address: wuhan university in Wuhan City, china, the preservation date: 2022, 06/02, accession No.: CCTCC NO: M2022783.
6. The use of a Lactobacillus plantarum strain according to claim 5, characterized in that the Lactobacillus plantarum strain is used for the preparation of notoginsenoside T5 and its isomers;
the chemical structural formula of the notoginsenoside T5 is as follows:
the chemical structural formula of the notoginsenoside T5 isomer is as follows:
7. the application of the lactobacillus plantarum as claimed in claim 5, characterized in that the lactobacillus plantarum is used for preparing notoginsenoside T5 and isomers thereof, and the preparation of notoginsenoside T5 and isomers thereof is obtained by converting notoginsenoside R1 into notoginsenoside T5 and isomers thereof through fermentation;
the chemical structural formula of the notoginsenoside T5 is as follows:
the chemical structural formula of the notoginsenoside T5 isomer is as follows:
8. a microbial inoculum obtained from the lactobacillus plantarum strain of claim 5 for the preparation of notoginsenoside T5 and its isomers; the chemical structural formula of the notoginsenoside T5 is as follows:
the chemical structural formula of the notoginsenoside T5 isomer is as follows:
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| CN101244105A (en) * | 2008-03-04 | 2008-08-20 | 文山壮族苗族自治州三七科学技术研究所 | Pseudo-ginseng standard extract P1237, its pharmaceutical combination, its preparing method and its uses |
| CN115029279A (en) * | 2022-06-27 | 2022-09-09 | 吉林省农业科学院 | Lactobacillus plantarum MB11 and application thereof in biotransformation preparation of rare ginsenoside |
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| CN101244105A (en) * | 2008-03-04 | 2008-08-20 | 文山壮族苗族自治州三七科学技术研究所 | Pseudo-ginseng standard extract P1237, its pharmaceutical combination, its preparing method and its uses |
| CN115029279A (en) * | 2022-06-27 | 2022-09-09 | 吉林省农业科学院 | Lactobacillus plantarum MB11 and application thereof in biotransformation preparation of rare ginsenoside |
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| In vitro biotransformation of red ginseng extract by human intestinalmicroflora: Metabolites identification and metabolic profile profileelucidation using LC–Q-TOF/MS;Huai-You Wang等;《Journal of Pharmaceutical and Biomedical Analysis》;20140611;第98卷;第296-306页 * |
| 三七中皂苷成分及其药理作用的研究进展;王莹等;《中草药》;20150531;第46卷(第09期);第1381-1392页 * |
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