CN108624533B - Method for separating and purifying phenyl lactic acid from lactobacillus plantarum - Google Patents
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Abstract
The invention discloses a method for separating and purifying phenyl lactic acid from lactobacillus plantarum, and belongs to the technical field of food biology. The lactobacillus plantarum ZJ316 disclosed by the invention is preserved in China center for type culture Collection with the preservation number of CCTCC NO: M208077. According to the invention, lactobacillus plantarum ZJ316 is taken as a target strain, and the content of phenyllactic acid in the fermentation supernatant of the MRS liquid culture medium is determined to be 108.87mg/mL (0.66mmol/L) by high performance liquid chromatography without any condition optimization, and the purity of the purified phenyllactic acid is up to 98.14%. The mass percentage range of the L-phenyl lactic acid is 92-98% by utilizing chiral chromatographic column-high performance liquid analysis. The product obtained by the invention is safe and reliable, can effectively inhibit food-borne pathogenic bacteria and putrefying bacteria, and can be applied to medicinal intermediates, food additives, cosmetics and the like.
Description
Technical Field
The invention belongs to the technical field of food biology, and particularly relates to a food with a preservation number of CCTCC NO: a method for separating and purifying phenyl lactic acid from fermentation supernatant of Lactobacillus plantarum ZJ316(Lactobacillus plantarum ZJ316) strain M208077.
Background
In the development of the food industry, antibacterial agents are essential in preventing spoilage of foods and extending the shelf life of foods. The variety and the number of the chemical synthetic antibacterial agents, particularly the non-food chemical antibacterial agents are multiplied, and the development of the food industry is promoted, and meanwhile, the serious food safety hidden danger is buried. Long-term research shows that some artificial preservatives have carcinogenicity and teratogenicity and are easy to cause food poisoning. The development of broad-spectrum, highly effective, safe, stable, natural antimicrobial agents is an inevitable requirement for the development of the food industry.
Food grade microorganismsLactic acid bacteria, a type of traditional fermentation strains, can ferment and metabolize to produce a variety of antibacterial substances, such as organic acids, bacteriocins, Rochelidon, hydrogen peroxide, and the like. Wherein the organic acid phenyl lactic acid is a novel natural antibacterial agent with molecular weight of 166Da and molecular formula of C9H10O3The second carbon atom in the molecular structure is a chiral carbon atom. The phenyl lactic acid has the characteristics of high water solubility, high stability, no damage after being kept at 121 ℃ for 20min and the like.
At present, only one bacteriocin of Nisin is commercially applied, and the application range is greatly limited due to the narrow antibacterial spectrum and the inhibition of partial gram-positive bacteria. Related researches show that the phenyllactic acid can effectively inhibit food-borne pathogenic bacteria and putrefying bacteria, such as escherichia coli, listeria monocytogenes, staphylococcus aureus, bacillus subtilis, salmonella, aspergillus niger, penicillium and the like. Compared with most of cationic antibacterial peptides, the phenyl lactic acid has high safety and wide antibacterial range, so that the phenyl lactic acid has good development and application prospects.
At present, researchers have separated and purified phenyl lactic acid from lactobacillus brevis, pseudomonas, geotrichum candidum, lactobacillus plantarum, fischer tropsch bacillus and the like, and the separation and purification methods are different and mainly comprise main solid phase extraction, thin layer chromatography, capillary electrophoresis, chiral column high performance liquid chromatography and the like. The invention discovers that the lactobacillus plantarum ZJ316 strain has the function of producing the phenyllactic acid, establishes the high performance liquid chromatography for separating and purifying the phenyllactic acid and measuring the enantiomer, and has great significance for screening, qualitative and quantitative measuring the phenyllactic acid producing strain.
Disclosure of Invention
The invention aims to establish a method for quickly and efficiently separating and purifying phenyllactic acid from the fermentation supernatant of lactobacillus plantarum ZJ316 and measure the broad-spectrum antibacterial effect of the phenyllactic acid.
The above object of the present invention is achieved by the following technical solutions:
lactobacillus plantarum ZJ316, deposited in the chinese type culture collection, address: the preservation number of the Wuhan university in Wuhan, China is CCTCC NO: M208077, and the preservation date is 2008, 5 months and 23 days.
The lactobacillus plantarum ZJ316 strain is activated and fermented in an MRS culture medium at the culture temperature of 37 ℃ for 24 hours. The fermentation broth was centrifuged and the supernatant was stored at 4 ℃.
The supernatant obtained by fermenting Lactobacillus plantarum ZJ316 is penetrated by XAD-2 macroporous resin, filtered by a membrane (0.22 μm), and subjected to two times of high performance liquid chromatography for separation and purification, wherein the model of the high performance liquid chromatography column is YMC-Pack ODS-AQ 150 × 20mm L.D., and the mobile phase is 0.05% trifluoroacetic acid/water and 0.05% trifluoroacetic acid/methanol (v/v).
The content of the phenyllactic acid in the fermentation supernatant of the lactobacillus plantarum ZJ316 is detected by analyzing a series of phenyllactic acid standard samples (Sigma company) with concentration gradients by utilizing high performance liquid chromatography (the type of a chromatographic column is YMC-Pack ODS-AQ 150 multiplied by 4.6mm L.D.) and establishing a linear relation of peak area-retention time to obtain a regression equation. The content of the phenyllactic acid in the fermentation supernatant of the lactobacillus plantarum ZJ316 is determined to be 108.87mg/mL, and the purity of the phenyllactic acid obtained by separation and purification is 98.14%.
Choose to race the road
IG (IG00CE-UC058) (0.46cm i.d. × 25cm L × 5 μm) chiral column, isocratic eluting with n-hexane/ethanol/trifluoroacetic acid (92/8/0.1 (v/v/v)) as mobile phase. The retention time of D/L type-phenyllactic acid in the phenyllactic acid is 11.288min and 12.309min respectively.
And respectively measuring the broad spectrum bacteriostasis and the minimum bacteriostasis concentration (MIC) of the phenyl lactic acid obtained by purification by an oxford cup method and a 96-well plate micro method. The results show that the phenyl lactic acid produced by the lactobacillus plantarum has an antibacterial effect on various pathogenic bacteria and putrefying bacteria and has a broad-spectrum antibacterial property.
The invention has the advantages that: the lactobacillus plantarum ZJ316 strain is determined to have the function of producing the phenyllactic acid, a method for separating and purifying the phenyllactic acid and determining the enantiomer thereof by high performance liquid chromatography is established, the broad-spectrum antibacterial property of the phenyllactic acid is determined, and the method has great significance for screening, qualitative and quantitative determination of the phenyllactic acid producing strain.
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FIG. 1 first HPLC elution chromatogram;
FIG. 2 Secondary HPLC elution chromatogram;
FIG. 3 shows the purity of phenyllactic acid separated and purified by HPLC;
FIG. 4 is a standard curve of peak area-retention time for the phenyl lactic acid standard;
FIG. 5 enantiomeric ratio (a) in the production of phenyllactic acid by Lactobacillus plantarum ZJ 316: chromatogram of sample introduction of D-phenyllactic acid standard substance; (b) the method comprises the following steps A chromatogram of equal proportion mixed sample injection of a D-phenyllactic acid standard substance and an L-phenyllactic acid standard substance; (c) the method comprises the following steps Chromatogram of sample injection of separation and purification of phenyllactic acid.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1: lactobacillus plantarum ZJ316 strain activation and fermentation supernatant preparation
Activating lactobacillus plantarum ZJ316 strain: taking out the strain from-80 deg.C, thawing at 4 deg.C, streaking in MRS solid culture medium, and standing at 37 deg.C for 24 hr; and selecting a single colony, performing static culture at 37 ℃ in an MRS liquid culture medium for 24h, and performing continuous passage twice to obtain a seed solution. Inoculating the seed liquid into a fermentation medium (MRS liquid) according to the inoculum size of 2% of the volume fraction, performing amplification culture, and performing static culture at 37 ℃ for 24h to obtain a fermentation liquid. The fermentation broth was centrifuged at 8000rpm for 15min (4 ℃) to obtain a supernatant which was stored at 4 ℃ until use.
Example 2: separation and purification of phenyllactic acid in fermentation supernatant of lactobacillus plantarum ZJ316
The centrifuged supernatant was adsorbed by XAD-2 macroporous resin, and the flow-through solution was collected and filtered through a microporous membrane (0.22 μm). The filtrate is separated and purified twice continuously by high performance liquid chromatography. First separation preparative HPLC conditions: column model YMC-Pack ODS-AQ 150X 20mm L.D., mobile phase: 0.05% trifluoroacetic acid/water (a) and 0.05% trifluoroacetic acid/methanol (B), uv detection conditions: detector model Waters 2998, detector wavelength: 215nm, column temperature: 25 ℃, flow rate: 4mL/min, sample size: 5 mL. Gradient elution method: 0. the volume ratio of eluent A/B at 5min, 25 min, 30 min, 40 min and 46 min is 95:5, 5:95, 95:5 and 95:5 respectively. Wherein the chromatographic peak with retention time of 24.854min is crude phenyllactic acid peak, and the high performance liquid chromatogram is shown in figure 1.
And (3) separating and purifying conditions of secondary high performance liquid chromatography: column model YMC-Pack ODS-AQ 150X 20mm L.D., mobile phase: 0.05% trifluoroacetic acid/water (a) and 0.05% trifluoroacetic acid/methanol (B), uv detection conditions: detector model Waters 2998, detector wavelength: 215nm, column temperature: 25 ℃, flow rate: 5mL/min, sample size: 5 mL. Gradient elution method: 0. the volume ratio of eluent A/B of 20min, 35 min, 40 min, 46 min and 50 min is respectively 80:20, 60:40, 5:95, 80:20 and 80: 20. Wherein the chromatographic peak with retention time of 24.918min is phenyllactic acid pure peak, and the high performance liquid chromatogram is shown in figure 2.
Example 3: yield and separation purity of phenyllactic acid in supernatant of lactobacillus plantarum ZJ316
Purity of phenyllactic acid (see fig. 3), analytical high performance liquid chromatography conditions: the model of the chromatographic column is YMC-Pack ODS-AQ 150 multiplied by 4.6mm L.D., and the ultraviolet detection conditions are as follows: detector model Waters 2498, detector wavelength: 215nm, column temperature: 25 ℃, flow rate: 0.8mL/min, sample size: 50 μ L. The mobile phase and gradient elution method are the same as the separation and purification by secondary high performance liquid chromatography in example 2.
A series of concentration gradients (0, 0.05mg/mL, 0.10mg/mL, 0.25mg/mL, 0.50mg/mL, 0.75mg/mL) of phenyllactic acid standards (purchased from Sigma) were assayed in the same manner. Standard curves of peak retention time and peak area were established and calculated to obtain a regression equation (see fig. 4).
Example 4: enantiomeric ratio of phenyllactic acid in supernatant of Lactobacillus plantarum ZJ316
Analysis of chiral molecules in the production of phenyllactic acid by fermentation of lactobacillus plantarum ZJ316 (see fig. 5), liquid chromatograph LC-20A (shimadzu, japan), chiral column model:track for competition
IG (IG00CE-UC058) (0.46cm i.d. × 25cm L × 5 μm), mobile phase: n-hexane/ethanol/trifluoroacetic acid (92/8/0.1 (v/v/v)), a column temperature of 25 ℃, an ultraviolet detection wavelength of 215nm, and a flow rate of 1.0 mL/min. The sample size was 5. mu.L, and the elution was performed isocratically for 20 min.
Example 5: broad spectrum bacteriostatic activity of purified phenyllactic acid in lactobacillus plantarum ZJ316 fermentation supernatant
And (3) carrying out broad-spectrum antibacterial activity determination on the purified phenyllactic acid by adopting an oxford cup method. The effect of the bacteriostatic substance on the indicator bacterium is measured according to the size of the bacteriostatic circle displayed by the Oxford cup method. And (3) determining the minimum inhibitory concentration of the phenyllactic acid by adopting a 96-well plate micro-method. Add 100. mu.L of indicator bacteria (starting OD) to 96-well plates in sequence6000.05), phenyl lactic acid was added to the corresponding 96-well plate in a volume of 50 μ Ι _, resulting in a final concentration gradient of phenyl lactic acid: 0.50mg/mL, 1.00mg/mL, 1.25mg/mL, 1.5mg/mL, 1.75mg/mL, 2.00mg/mL, 2.50mg/mL, 3.00mg/mL, 3.50mg/mL, 4.00 mg/mL. Culturing 96-well plate under proper indicator bacteria culture condition, and measuring OD every 1 hr with enzyme labeling instrument600The value is obtained. And starting OD600Value comparison, OD 24 hours of culture600The concentration of phenyllactic acid under this condition was defined as the Minimum Inhibitory Concentration (MIC) of phenyllactic acid against the indicator bacteria without increasing the value.
The results show that the phenyl lactic acid produced by the lactobacillus plantarum has an antibacterial effect on various pathogenic bacteria and spoilage bacteria (see table 1) and has a broad-spectrum antibacterial property.
TABLE 1 antibacterial effect of Lactobacillus plantarum ZJ316 producing phenyllactic acid on indicator bacteria and its minimum inhibitory concentration
Note: diameter of zone of inhibition (mm): "+ + + +", d >16.00, "+ +" 14.00< d <16.00, "+": d <14.00, "-": no antibacterial effect, "/": and (5) not testing.
Claims (5)
1. A method for separating and purifying phenyl lactic acid from lactobacillus plantarum, wherein the lactobacillus plantarum is preserved in China center for type culture Collection with the preservation number of CCTCC NO: m208077, which is characterized in that the mass percentage range of L-phenyllactic acid in the separated and purified phenyllactic acid is 92% -98%;
the method comprises the following steps:
activating lactobacillus plantarum to grow a single colony, obtaining seed liquid from the single colony, obtaining fermentation liquid according to the seed liquid, and centrifuging the fermentation liquid to obtain supernatant;
separating and purifying the fermentation supernatant by high performance liquid chromatography to obtain phenyllactic acid;
the separation and purification method comprises the following steps:
collecting the fermented supernatant, adsorbing with XAD-2 macroporous resin, and collecting the penetrating liquid;
taking 0.05% trifluoroacetic acid/water (A) and 0.05% trifluoroacetic acid/methanol (B) (v/v) as mobile phases, and performing two times of high performance liquid chromatography gradient elution by using a YMC-Pack ODS-AQ 150 × 4.6mm L.D. type chromatographic column, and separating and purifying to obtain the phenyllactic acid; the first high performance liquid chromatography gradient elution method comprises the following steps: 0. the volume ratio of eluent A/B for 5min, 25 min, 30 min, 40 min and 46 min is respectively 95:5, 5:95, 95:5 and 95:5, and the flow rate is 4.0 mL/min; the secondary high performance liquid chromatography gradient elution method comprises the following steps: 0. the volume ratio of eluent A/B of 20min, 35 min, 40 min, 46 min and 50 min is respectively 80:20, 60:40, 5:95, 80:20 and 80:20, and the flow rate is 5.0 mL/min;
isocratically eluting for 20min by chiral chromatographic column-high performance liquid chromatography to obtain the ratio of L-phenyllactic acid and D-phenyllactic acid in phenyllactic acid; the mobile phase is n-hexane/ethanol/trifluoroacetic acid (92/8/0.1 (v/v/v)), and the chiral chromatographic column model is Daseluo
IG00 CE-UC0580.46cm I.D. times 25cm L times 5 μm, the flow rate is 1.0 mL/min.
2. The method of claim 1, wherein the activated lactobacillus plantarum grows a single colony specifically as follows: streaking lactobacillus plantarum on an MRS solid culture medium, culturing at 37 ℃ for 24h, and growing a single colony of lactobacillus plantarum, wherein the MRS solid culture medium is prepared from the following components: 20g of anhydrous glucose, 801 mL/L of Tween-801, 0.2g of magnesium sulfate heptahydrate, 0.05g of manganese sulfate, 10g of tryptone, 5g of yeast extract, 2g of dipotassium phosphate, 2g of triammonium citrate, 10g of beef extract, 5g of anhydrous sodium acetate, 15g of agar, pH 7.0, supplementing ultrapure water to 1000mL, and sterilizing at 121 ℃ for 15 min.
3. The method of claim 1, wherein said obtaining a seed fluid from a single colony is specifically: selecting a single colony grown out, placing the single colony in an MRS liquid culture medium, and carrying out continuous passage for 2 times to obtain a seed liquid, wherein the MRS liquid culture medium is prepared from the following components: 20g of anhydrous glucose, 801 mL/L of Tween-801, 0.2g of magnesium sulfate heptahydrate, 0.05g of manganese sulfate, 10g of tryptone, 5g of yeast extract, 2g of dipotassium phosphate, 2g of triammonium citrate, 10g of beef extract, 5g of anhydrous sodium acetate, pH 7.0, supplementing ultrapure water to 1000mL, and sterilizing at 121 ℃ for 15 min.
4. The method according to claim 1, wherein the obtaining of the fermentation broth from the seed liquid is in particular: inoculating the seed liquid into MRS liquid according to the inoculum size of 2% of the volume fraction, and performing static culture at 37 ℃ for 24h to obtain fermentation liquid.
5. The method of claim 1, wherein the conditions for centrifuging the fermentation broth are 8000rpm, 15min, 4 ℃.
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| CN110205267A (en) * | 2019-05-31 | 2019-09-06 | 上海应用技术大学 | The lactobacillus plantarum of one plant of bacteriocinogeny and its application |
| CN111264817B (en) * | 2019-12-24 | 2023-02-21 | 浙江工商大学 | Application of direct vat set lactobacillus starter in preserved szechuan pickle pickling |
| CN111197015B (en) * | 2019-12-24 | 2022-06-10 | 浙江工商大学 | Direct vat set lactic acid bacteria starter and preparation method thereof |
| CN114657083A (en) * | 2019-12-24 | 2022-06-24 | 顾青 | Lactic acid bacteria fermented milk |
| CN114044750B (en) * | 2021-08-06 | 2022-09-23 | 浙江工商大学 | Method for purifying indole-3-lactic acid in plant lactobacillus fermentation supernatant |
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