CN111088167A - Extraction process of xanthone in penicillium oxalicum and application of xanthone as antioxidant - Google Patents
Extraction process of xanthone in penicillium oxalicum and application of xanthone as antioxidant Download PDFInfo
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Abstract
The invention discloses penicillium oxalicum (A)Penicillium oxalicum) Secondary metabolite 2,2 ', 6' -trihydroxyA separation and extraction process of the 4-methyl-6-methoxyl-acyl-diphenyl ketone and antioxidation. Experiments prove that the application of the 2,2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-diphenyl ketone obtained by separating and extracting the penicillium oxalicum secondary metabolite as an antioxidant reagent provides a new choice for developing a new antioxidant, and has good economic and social benefits.
Description
Technical Field
The invention relates to a method for separating and extracting xanthone from Penicillium oxalicum (Penicillium oxalicum) secondary metabolite and application of xanthone as an antioxidant agent.
Background
In normal metabolic activity, organisms generate various free radicals due to incomplete oxidation, the free radicals have strong oxidizing capability and are normally cleared by endogenous protection mechanisms of the organisms, but once the organisms face adversity stress, the oxidative stress of the organisms induces excessive free radicals to be formed in the organisms, so that the organisms are guided to age and die.
"Antioxidant" (Antioxidant) generally refers to an abbreviation for Antioxidant free radical, which stops or slows down the oxidation reaction of a target substance by supplying hydrogen protons that are bound to the free radical to undergo an oxidation reaction by itself to scavenge the free radical or convert the free radical into an inert compound. The antioxidant can prevent free radicals of organism from abstracting oxygen atoms from cells and other tissues, and prevent the damage of the free radicals to normal cell tissues, thereby improving the capability of the organism to resist adversity stress and the anti-aging capability, and further playing a role in preventing diseases related to oxidative stress.
At present, the extraction and separation of natural antioxidant products are difficult points, and a series of problems that an extraction process damages a material structure, an extract is toxic, has residues and is not easy to separate, the separation and extraction speed is low, the efficiency is low, the cost is high and the like generally exist.
Disclosure of Invention
One of the objectives of the present invention is to provide a method for separating and extracting xanthone from the metabolite of Penicillium oxalicum (Penicillium oxalicum), wherein the xanthone has a certain antioxidant effect and a relatively high yield (about 0.75mg/L), and can be used for preparing antioxidant, thereby providing a new choice for developing new antioxidant.
The Penicillium oxalicum (Penicillium oxalicum) is an endophytic fungus obtained from leaves of cypress blossoms (Myricarialaxiflora), is preserved in China Center for Type Culture Collection (CCTCC) in 2017 at 1 month and 11 days, is classified and named as Penicillium oxalicum SY-15, and has the preservation number of CCTCC No: m2017025. The preservation address is China, Wuhan and Wuhan university.
The method takes a fermentation liquor ester phase crude extract of Penicillium oxalicum (Penicillium oxalicum) as a main active site, and obtains a ketone compound through a series of separation and purification processes such as rotary evaporation, thin-plate chromatography (TLC), column chromatography, High Performance Liquid Chromatography (HPLC), and the like, and the structure of the ketone compound is 2,2, 6-trihydroxy-4-methyl-6-methoxy-acyl-diphenyl ketone identified by Bopu analysis. The specific process comprises the following steps:
activating strains: taking a penicillium oxalicum strain, inoculating the penicillium oxalicum strain into a PDA solid plate culture medium, and carrying out activated culture;
culturing: inoculating the activated penicillium oxalicum strains to a PDA liquid culture medium, and carrying out constant-temperature shaking table culture to obtain penicillium oxalicum suspension;
separation and extraction: filtering the cultured penicillium oxalicum bacterial suspension, removing thalli, extracting supernatant with ethyl acetate, concentrating extract at 30-45 ℃ under reduced pressure to obtain concentrated solution, freeze-drying the concentrated solution, performing thin-plate chromatography (TLC), performing column chromatography, and performing High Performance Liquid Chromatography (HPLC), wherein the extract is the xanthone, has a chemical formula of 2,2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-diphenyl ketone, and has a structural formula as follows:
the obtained 2,2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-diphenyl ketone is light yellow powder.
The invention aims to provide a research for an antioxidant, and the active ingredient of the research is 2,2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-diphenyl ketone. Antioxidant tests show that the DPPH free radical clearance rate is 80.67%, the total antioxidant capacity is 70.66U/mL, and the reducing power of potassium ferricyanide is 1.43.
Drawings
FIG. 1 is a HPLC analysis chart of the present invention.
FIG. 2 is a carbon spectrum of 2,2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-diphenyl ketone as xanthone of the present invention.
FIG. 3 is a hydrogen spectrum of 2,2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-diphenyl ketone as xanthone oxide of the present invention.
FIG. 4 is a graph showing the effect of heteroanthrone 2,2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-benzophenone of the present invention on the growth activity protection of Saccharomyces cerevisiae BY4742 under oxidative stress of menadione, wherein A is BY4742 direct culture, B is menadione added with oxidant, C is menadione added with oxidant and glutathione, and D is menadione added with oxidant and heteroanthrone antioxidant.
FIG. 5 is a graph showing the protective effect of the rhodoxanthin 2,2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-benzophenone on the saccharomyces cerevisiae BY4742 under the oxidative stress of menadione in different concentration gradients, wherein A is 1mg/mL of the rhodoxanthin, B is 3mg/mL of the rhodoxanthin, and C is 3mg/mL of the rhodoxanthin.
Detailed Description
Example 1: activated culture of Penicillium oxalicum (Penicillium oxalicum)
Activating strains: taking Penicillium oxalicum stored in a refrigerator at 4 ℃, picking up a small amount of strains, inoculating the strains into a PDA (fresh potato 200g/L, sucrose 20g/L, agar 20g/L, pH7.2-7.5, sterilizing at 121 ℃ for 20min) solid plate culture medium, and culturing at 28 ℃ in an incubator for 7 days.
And (3) strain culture: the activated strain sample is inoculated to 200ml LPDA (fresh potato 200g/L, sucrose 20g/L, pH7.2-7.5, 121 ℃ sterilization 20min) liquid culture medium, and cultured for 7 days in a shaking table at a constant temperature of 28 ℃ and 120 r/min.
Preliminary separation and extraction of metabolite of Penicillium oxalicum (Penicillium oxalicum):
filtering the cultured strain with vacuum filtration device, discarding thallus, extracting the supernatant with equal volume of ethyl acetate for three times, mixing the extractive solutions, concentrating the extractive solution at 40 deg.C under reduced pressure to obtain concentrated solution, and freeze drying the concentrated solution to obtain crude extract. Thin plate chromatography (TLC) for crude extract
(ultraviolet 254nm) and column chromatography, eluting with petroleum ether/acetone at a volume ratio of 1:3 to obtain metabolite, measuring antioxidant activity by T-AOC method to 94.23U/mL, and storing in refrigerator at 4 deg.C.
Example 2: separation and extraction of 2,2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-diphenyl ketone as xanthone oxide
HPLC (high performance liquid chromatography): the metabolite stored at 4 ℃ in example 1 was taken to prepare a solution with a concentration of 1mg/mL for further use, 50. mu.L of the solution was subjected to sample injection analysis (method chromatography conditions: C18(4.6 mm. times.250 mm,5 μm) chromatographic column, wavelength 210nm, mobile phases: A: water, B: acetonitrile (gradient elution), column temperature 35 ℃, total flow rate 1.0m L/min, sample injection amount 20. mu.L), and peak enrichment with a peak time of 18.5min was selected.
B, performing Pop analysis: after enriching, concentrating, freeze-drying collected samples, adopting various classical chromatographic purification techniques, Bopu's chemical techniques and physicochemical properties, separating to obtain a peak of 18.5min in HPLC, and identifying the structure as 2,2 ', 6 ' -trihydroxy-4-methyl-6-methoxy-acyl-diphenyl ketone (called as heteroanthrone for short).
Example 3: in vitro antioxidant activity analysis of xanthone-2, 2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-diphenyl ketone
The xanthone is prepared into a 1mg/mL solution by using methanol as a solvent, the antioxidant capacity of the solution is respectively measured by a DPPH (1, 1-diphenyl-2-trinitrophenylhydrazine) free radical scavenging method, a T-AOC kit and a Potassium Ferricyanide (PF) reduction force measuring method, the steps are repeated for 3 times, and glutathione with the same concentration is used as a positive control. The result shows that the scavenging rate of free radicals of the xanthone oxide reaches 80.67 percent, the antioxidant activity of the xanthone oxide is 70.66U/mL measured by a T-AOC method, the light absorption value of the xanthone oxide measured by the reduction force of potassium ferricyanide is 1.43, the difference between the xanthone oxide and the antioxidant glutathione is very small, and the xanthone oxide has strong antioxidant capacity.
The results of the antioxidant activity measurement are shown in Table 1
TABLE 1 measurement results of antioxidant Activity
Antioxidant activity method determination reference is as follows
Determination of antioxidant Activity by DPPH method
The determination principle is as follows: DPPH free radical has single electron, and has a strong absorption at 517nm, and its alcoholic solution is purple. In the presence of the radical scavenger, the purple color gradually disappears as the radical scavenger can pair with the DPPH singlet electron and cause its singlet electron to be absorbed. The lighter the purple color of the DPPH alcoholic solution, the more radical scavengerClearance rateThe larger, the stronger its antioxidant capacity is indicated. Therefore, the removal rate of DPPH free radicals of the sample can be rapidly and quantitatively analyzed according to the change of the purple color of the DPPH alcoholic solution.
The experimental procedure was as follows:
(1) preparing 30 mu g/mL alcoholic solution of DPPH by using absolute ethyl alcohol, and storing at-20 ℃ in the dark for later use.
(2) 3.8mL of 30. mu.g/mL DPPH alcohol solution was mixed with 0.2mL of the sample solution, and the mixture was reacted for 90min at room temperature in the absence of light.
(3) After the reaction, the OD value was measured at 517nm with a spectrophotometer.
The DPPH clearance calculation formula is as follows:
clearance rate ═ 1-Ai/Ac]×100％(AiFor absorbance values with addition of antioxidants, AcAbsorbance of blank control tube).
Determination of antioxidant Activity by T-AOC kit
The principle of the kit is as follows: uses many substances which can resist oxidation in the body and can convert Fe3+For reduction to Fe2+And is of Fe2+Can form stable complex with phenanthroline substances, and the oxidation resistance of the antioxidant substances can be measured by the colorimetry of a spectrophotometer. The protective oxidation of this system is mainly through three routes: (1) eliminating active oxygen and free radical to avoid initiating lipidPeroxidation of biomass; (2) blocking peroxide chains and decomposing peroxide; (3) removing the metal ions which play a catalytic role. The absorbance was measured by zeroing with double distilled water and measuring the absorbance at 520nm, and the order of adding the reagents is shown in Table 3.
Meanwhile, Vc solution with corresponding concentration is used as a positive control, and the method is the same as the above method, and distilled water is used as a blank control. Three replicates per group were made.
Defining: the calculation formula for each 0.01 increase in the absorbance (OD) of the reaction system per ml at 37 ℃ is as follows:
ODU: measuring the tube absorbance value;
ODC: comparing the absorbance value of the tube;
n: dilution ratio of the reaction system (total volume of reaction solution/sampling amount);
n: samples were diluted multiple before testing.
TABLE 2 reagent compositions and formulations
Note: and preparing a reagent II by application: 120mL of double distilled water is added into each powder for full dissolution (the powder is difficult to dissolve, if the dissolution needs to be accelerated, the powder can be dissolved in water bath at 37 ℃).
Preparing a reagent three-application solution: the stock solution is taken before use and diluted by diluent 1:19, and the stock solution is prepared as it is.
TABLE 3 sequence of addition of reagents
Note: a sample volume (reference value 0.1mL)
3. Method for measuring reduction force of potassium ferricyanide
The principle is as follows: because the antioxidant substance can reduce potassium ferricyanide into potassium ferrocyanide, the potassium ferrocyanide can react with ferric trichloride to generate Prussian blue, and the maximum absorption light is at 700 nm. Therefore, the antioxidant activity can be measured by a spectrophotometer, and the higher the absorbance value is, the higher the antioxidant activity is.
Adding 1mL of sample solution, 2.5mL of phosphate buffer solution with pH value of 6.6 and 2.5mL of 1% potassium ferricyanide solution into each test tube, reacting in a water bath kettle at 50 ℃ for 20min, adding 2.5mL of 10% trichloroacetic acid solution and 0.5mL of 0.1% ferric trichloride solution, mixing uniformly, and measuring the light absorption value at 700 nm. Meanwhile, Vc solution with corresponding concentration is used as a positive control, and distilled water is used as a blank control. Three replicates per group were made.
Example 4: analysis of in vivo antioxidant Activity of Heteroxanthrone-2, 2 ', 6' -Trihydroxyl-4-methyl-6-methoxy-acyl-Diphenyl methanone
Activation of Saccharomyces cerevisiae (Saccharomyces cerevisiae) BY 4742: the Saccharomyces cerevisiae BY4742 preserved at-80 ℃ is inoculated in YPD solid culture medium (yeast extract 10g/L, peptone 20g/L, glucose 20g/L, agar 20g/L, pH7.2-7.5, sterilized at 121 ℃ for 20min) and activated and cultured in an incubator at 28 ℃ for 24 h.
Culture of Saccharomyces cerevisiae (Saccharomyces cerevisiae) BY 4742: inoculating activated Saccharomyces cerevisiae BY4742 to 200ml LYPD liquid culture medium (yeast extract 10g/L, peptone 20g/L, glucose 20g/L, pH7.2-7.5, sterilizing at 121 deg.C for 20min), and shake culturing at 28 deg.C and 120r/min for 12h to obtain seed fermentation liquid. 100uL of seed yeast fermentation broth is transferred and inoculated in 200mLYPD liquid culture medium, and is cultured for 12h in a constant temperature shaking table at 28 ℃ and 120 r/min.
Oxidative damage protection assay for xanthone-2, 2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-benzophenone against Saccharomyces cerevisiae (Saccharomyces cerevisiae) BY 4742: menadione is selected as an oxidant to be prepared into a solution of 1mg/mL for standby, glutathione is weighed to be prepared into a solution of 3mg/mL for standby, and xanthone is prepared into a solution of 3mg/mL for standby. The cultured 4 flasks of Saccharomyces cerevisiae BY4742 were marked for ABCD. A is naturally growing yeast, B is yeast under oxidative stress of receiving an oxidant menadione, C is yeast under oxidative stress with antioxidant glutathione added, and D is yeast with oxidation stress with heteroanthrone added.
Culturing in shaking bed at 28 deg.C and 120r/min for 3 hr, spreading on YPD solid culture medium (yeast extract 10g/L, peptone 20g/L, glucose 20g/L, agar 20g/L, pH7.2-7.5, sterilized at 121 deg.C for 20min), culturing in 28 deg.C incubator for 24 hr, and observing growth state. The amounts and concentrations of the specific added substances are shown in table 3:
table 4 shows the amounts and concentrations of the substances added
FIG. 4 result AB shows that the number of yeast is obviously reduced after the yeast is subjected to menadione oxidative stress, ABD can see that the yeast activity can be obviously improved by adding heteroanthrone into the yeast subjected to oxidative stress to improve the growth condition of the yeast, and the number of the live yeast is not much different from that of the yeast grown in the natural condition. CD shows that the xanthone and the positive control glutathione can effectively resist the oxidative stress of menadione and improve the survival quantity of yeast. In conclusion, the obtained xanthone has obvious effect of effectively resisting oxidative stress.
Determination of oxidative damage protection effect of variegated concentrations of xanthone-2, 2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-benzophenone on oxidative stress of menadione in Saccharomyces cerevisiae BY 4742: selecting menadione as oxidant, preparing into 1mg/mL solution for standby, weighing xanthone, using methanol as solvent to prepare into 1mg/mL, 3mg/mL and 6mg/mL solutions for standby, taking cultured Saccharomyces cerevisiae BY4742 as marked ABC, simultaneously adding same amount of oxidizing agent menadione, respectively adding same amount of xanthone with different concentrations, placing at 28 ℃, culturing for 3h in 120r/min constant temperature shaking table, taking out strain fermentation liquor, diluting to 10-3Taking 5uL, inoculating to YPD solid medium (yeast extract 10g/L, peptone 20g/L, glucose 20g/L, agar 20g/L, pH7.2-7.5, sterilizing at 121 deg.C for 20min)And culturing in a medium 28 ℃ incubator for 24h, repeating six groups, and observing the growth condition of the medium 28 ℃ incubator. The amounts and concentrations of the specific added substances are shown in table 5:
TABLE 5 addition amounts and concentrations of the respective raw materials
The results of Saccharomyces cerevisiae BY4742 after oxidative stress with menadione at the same concentration and dose are shown in FIG. 5.
The results in FIG. 5 show that: after the Saccharomyces cerevisiae (Saccharomyces cerevisiae) of three groups ABC are subjected to oxidative stress under the same conditions, the oxidation damage protection effects of the xanthones with different concentrations are obviously different, the concentration of the xanthone of the three groups ABC is in direct proportion to the growth condition of the Saccharomyces cerevisiae (Saccharomyces cerevisiae) from low to high, the group A has larger difference compared with the group C, the number of strains of the group C with better growth vigor is relatively more, and therefore, the higher the concentration of the xanthone is, the better the oxidation damage protection effect of the Saccharomyces cerevisiae (Saccharomyces cerevisiae) BY4742 is.
Claims (3)
1. The extraction process of xanthone in penicillium oxalicum is characterized by comprising the following steps of:
activating strains: taking a penicillium oxalicum strain, inoculating the penicillium oxalicum strain into a PDA solid plate culture medium, and carrying out activated culture;
culturing: inoculating the activated penicillium oxalicum strains to a PDA liquid culture medium, and carrying out constant-temperature shaking table culture to obtain penicillium oxalicum suspension;
separation and extraction: filtering the cultured penicillium oxalicum bacterial suspension, removing thalli, extracting supernatant with ethyl acetate, concentrating extract at 30-45 ℃ under reduced pressure to obtain concentrated solution, freeze-drying the concentrated solution, performing thin-plate chromatography (TLC), performing column chromatography, and performing High Performance Liquid Chromatography (HPLC) to obtain extract, namely xanthone with a chemical formula of 2,2 ', 6' -trihydroxy-4-methyl-6-methoxy-acyl-diphenyl ketone, wherein the structural formula is as follows:
2. the process for extracting xanthone from Penicillium oxalicum, according to claim 1, wherein the Penicillium oxalicum is an endophytic fungus obtained from leaves of the branches of the phellodendron sieboldii, is deposited in the China center for type culture Collection on 1/11/2017, is classified and named as Penicillium oxyalicum SY-15 with the preservation number of CCTCC M: 2017025, the preservation address is China, Wuhan university.
3. Use of the extracted xanthone of claim 1 or 2 as an antioxidant.
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| CN112741829A (en) * | 2020-08-11 | 2021-05-04 | 黑龙江中医药大学 | Application of aspergillus fumigatus benzophenone I in preparation of antioxidant drugs |
| CN113455541A (en) * | 2021-06-21 | 2021-10-01 | 三峡大学 | Citrus preservative |
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| CN106929430A (en) * | 2017-02-10 | 2017-07-07 | 三峡大学 | One plant of penicillium oxalicum SY 15 with strong anti-oxidation and its application |
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| CN106929430A (en) * | 2017-02-10 | 2017-07-07 | 三峡大学 | One plant of penicillium oxalicum SY 15 with strong anti-oxidation and its application |
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| BING LIU等: "ISOLATION OF A NEW COMPOUND FROM Penicillium oxalicum", 《CHEMISTRY OF NATURAL COMPOUNDS》 * |
| BING LIU等: "New compound with DNA Topo I inhibitory activity purified from Penicillium oxalicum HSY05", 《NATURAL PRODUCT RESEARCH》 * |
| ZHENG NIU等: "Cytotoxic Polyketides from a Deep-Sea Sediment Derived Fungus Diaporthe phaseolorum FS431", 《MOLECULES》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112741829A (en) * | 2020-08-11 | 2021-05-04 | 黑龙江中医药大学 | Application of aspergillus fumigatus benzophenone I in preparation of antioxidant drugs |
| CN113455541A (en) * | 2021-06-21 | 2021-10-01 | 三峡大学 | Citrus preservative |
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