CN109045020A - The purposes of Aspergillus terreus secondary metabolite extract - Google Patents
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Abstract
The invention discloses Aspergillus terreus secondary metabolite extracts as the purposes for removing free radical biological agent.The preparation step of secondary metabolite extract are as follows: epigenetic modification adjusting control agent TSA, niacinamide, two peptide are added into fungi culture medium, fermented and cultured, extractive fermentation liquid, mycelium are distinguished with the acetone-water of ethyl acetate, 80%, fermented concentrate is purified through column chromatography, high performance liquid chromatography separation, obtains secondary metabolite extract.Have the beneficial effect that the present invention apparently modifies A terreus using epigenetic modification adjusting control agent TSA, a kind of isolated secondary metabolite extract.A terreus secondary metabolite extract produced by the present invention has stronger antioxidant activity, can develop the purposes for removing free radical biological agent for potential preparation, can be applied to pharmaceuticals, cosmetics and field of food.
Description
Technical field
The present invention relates to technical field of pharmaceuticals, remove free radical biological agent more particularly, to a kind of can be used as
The Preparation method and use of Aspergillus terreus secondary metabolite extract.
Background technique
The probability for obtaining noval chemical compound from the microorganism of land in recent years is greatly reduced, and marine-derived microorganism is due to it
Living environment is special, in addition to it can produce metabolite similar with land, can also generate special newization of some structures sometimes
Close object, it is shown that huge exploitation prospect.Aspergillus fungi is all the important strain of natural products circle research all the time
Its secondary metabolite structure novel skeleton is changeable, in addition to conventional steroidal, sequiterpene, and other than the common structures type such as anthraquinone,
Contain toward contact: alkaloids, a variety of skeletons such as peptides, polyketone class, sesterterpene.The compound of these structure novels is often
Also contain cell toxicant, antibacterial, the various actives such as antiviral become one of the important sources of marine drug lead compound, cause
The extensive concern of scholar in the industry.
Oxygen radical is a kind of harmful substance, referred to as " killers of good health and a long life ".Excessive active oxygen is free in human body
Base can destroy human body cell and tissue, cause a variety of diseases, such as heart disease, senile dementia, Parkinson's disease and tumour.This
Outside, the solar irradiation in external environment, air pollution, smoking, pesticide etc. can all make human body generate more active oxygen radicals,
Cause aging and illness.For removing machine interior free yl, we tackle oxygen radical using anti-oxidation method.But at present
Natural antioxidant oxidability is not strong enough, and there are also side effects, and anti-oxidation medicine, Chang Yinwei molecular weight are too big, cannot be very
Good is received by human body, causes antioxidant effect bad.Therefore, it is strong and be easily absorbed by the body anti-to find a kind of oxidation resistance
Oxidant is emphasis concerned by people.
The prior art such as Authorization Notice No. is the Chinese invention patent of CN101234951B, discloses a kind of biphenyl class chemical combination
Object and its preparation method and application, preparation step include the seed liquor and fermentation liquid of aspergillus clavato-nanica BYY-1, biphenyl compound
Extraction, the purification of biphenyl compound, the biphenyl compound derive from mangrove endophytic fungus secondary metabolite, be nothing
Color acicular crystal has bioactivity, inoxidizability and cancer inhibitor cell ability.
Summary of the invention
The purpose of the present invention is to provide Aspergillus terreus secondary metabolite extracts to remove free radical
Purposes in biological agent, secondary metabolite are to modify Aspergillus through epigenetic modification adjusting control agent TSA
Terreus fermentation, then abstraction purification obtains.
The present invention in view of the above technology in the problem of mentioning, the technical solution taken are as follows:
Present invention strain by Qingdao Stone old man bathing beach Enteromorpha sample total epiphytic fungi, pass through chemistry and biology
Method screens gained jointly.
Secondary metabolite is removing the purposes in free radical biological agent, wherein secondary metabolite is shown in Formulas I
Compound, its stereoisomer or pharmaceutically accessible salt, chemical structural formula are as follows:
The preparation method of Aspergillus terreus secondary metabolite extract includes the following steps:
Strain fermentation: adding epigenetic modification adjusting control agent TSA, niacinamide, two peptide into fungi culture medium, and stirring is equal
It is even, it stands, fermented and cultured；
Secondary metabolite extraction: with silk by mycelium and separation of fermentative broth；Fermentation liquid is extracted with ethyl acetate, decompression
Concentration, obtains fermentation liquid extract；80% acetone-water, 2- methylalanine and calcium citrate is added in mycelium, impregnates, tissue
Broken instrument is broken, ultrasonic extraction 30min, filters to obtain clear liquid, and ethyl acetate extraction is concentrated under reduced pressure, obtains fermentation mycelium extract；
Merge fermentation liquid extract and fermentation mycelium extract, obtains final fermentation, extraction object；
Isolate and purify: final fermentation, extraction object successively uses silica gel column chromatography, Sephadex LH-20 column chromatography, RP-18 anti-
The Aspergillus terreus cometabolism production that phase silica gel column chromatography, high performance liquid chromatography are isolated and purified to get purifying
Object.
Preferably, fermented incubation time is 30 days in strain fermentation step.
Preferably, in strain fermentation step, final concentration of 5-25 μM of epigenetic modification adjusting control agent TSA.
Preferably, the additive amount of niacinamide is 0.05-0.1%, and two peptide additive amount is in strain fermentation step
0.05-0.15%；Niacinamide, two peptide are added in fungi culture medium, can improve the component of fermentation medium, change culture medium
Interior nutrient environment improves culture medium nutrition, promotes the mitotic rate of mycelial cell, realizes mycelium secondary metabolite
The quick raising of middle monomeric compound fermentation level, meanwhile, it acts synergistically, promotes with histon deacetylase (HDAC) inhibitor TSA
TSA carries out epigenetic modification regulation in conjunction with the active site of mycelial cell access, to mycelial cell, promotes fungi time
The generation and growth of grade metabolite, increase the yield of mycelium secondary metabolite；
Preferably, the additive amount of 2- methylalanine is the 1- of culture medium quality in secondary metabolite extraction step
3%, the additive amount of calcium citrate is the 0.5-1.5% of culture medium quality；2- methylalanine and calcium citrate collective effect, pole
The earth infiltration mycelial cell wall, destroys mycelial cell wall by chemical affinities such as hydrogen bond, Van der Waals force, electrostatic attractions
Structure changes cell wall permeability, is broken its molecular structure, broken hole occurs, then the mechanical effect of synergistic supersonic wave, cavitation
Effect and fuel factor promote release, diffusion and the dissolution of substance in mycelial cell, improve the extraction yield of mycelium extract.
Preferably, in purification procedures, silica gel column chromatography, Sephadex LH-20 column chromatography, RP-18 reverse phase silica gel
Column chromatography, high performance liquid chromatography eluant, eluent successively are as follows: petroleum ether-methylene chloride-methanol, methylene chloride-methanol, methanol-water,
Methanol-water.
Compared with the prior art, the advantages of the present invention are as follows: the present invention is modified by epigenetic modification adjusting control agent TSA and is made
Aspergillus terreus secondary metabolite；The present invention adds niacinamide, two peptide in the medium, with epigenetic
It modifies adjusting control agent TSA and generates cooperative gain effect, promote Aspergillus terreus to generate diversified cometabolism and produce
Object；The present invention is in mycelium extraction process, addition 2- methylalanine and calcium citrate, the mechanism of synergistic supersonic wave,
Cavitation destroys cell wall, accelerates intracellular organic matter release, improves fermentation material extraction yield；The present invention is from Aspergillus
Terreus secondary metabolite extract has stronger antioxidant activity, can remove free radical biological agent as preparation
Purposes.
Specific embodiment
The present invention program is described further below by embodiment:
Embodiment 1:
The purposes of Aspergillus terreus secondary metabolite extract, made secondary metabolite are shown in Formulas I
Compound, its stereoisomer or pharmaceutically accessible salt, chemical structural formula are as follows:
The purposes of Aspergillus terreus secondary metabolite extract, the secondary metabolite extract
Preparation method includes strain fermentation, secondary metabolite extraction and isolates and purifies, specific steps are as follows:
Strain fermentation: the addition epigenetic modification adjusting control agent TSA into fungi culture medium, final concentration of 15 μM,
0.05% niacinamide, 0.1% two peptide, stir evenly, and stand, fermented and cultured 30 days, a common fermentation 60L；Niacinamide, two peptide
It is added in fungi culture medium, the component of fermentation medium can be improved, change nutrient environment in culture medium, improves culture medium battalion
It supports, promotes the mitotic rate of mycelial cell, realize monomeric compound fermentation level in mycelium secondary metabolite
Quickly improve, meanwhile, it acts synergistically with histon deacetylase (HDAC) inhibitor TSA, promotes the work of TSA and mycelial cell access
Property site combine, to mycelial cell carry out epigenetic modification regulation, promote fungal secondary metabolite generation and growth,
Increase the yield of mycelium secondary metabolite；
Secondary metabolite extraction: after fermentation, with silk by mycelium and separation of fermentative broth；The bodies such as fermentation liquid addition
Long-pending ethyl acetate stirring extraction 3 times, ethyl acetate is concentrated under reduced pressure, fermentation liquid extract is obtained；The third of 80% is added in mycelium
Ketone-water, 2%2- methylalanine, 1% calcium citrate impregnate, and are crushed instrument with the ultrasonic tissue of power 800W, with ultrasonic 3s,
30min is then extracted by mycelium ultrasonication 45 times every the method for 3s, clear liquid is obtained with filtered on buchner funnel, depressurizes dense
Contracting is added isometric ethyl acetate and extracts 3 times, obtains fermentation mycelium extract；Merge fermentation liquid extract and fermented hypha
Body extract obtains final fermentation, extraction object；2- methylalanine and calcium citrate collective effect, greatly infiltration mycelial cell
Wall destroys mycelial cell wall construction by chemical affinities such as hydrogen bond, Van der Waals force, electrostatic attractions, it is logical to change cell wall
Permeability is broken its molecular structure, broken hole occurs, then the mechanical effect of synergistic supersonic wave, cavitation effect and fuel factor, promotes
The release, diffusion and dissolution of substance in mycelial cell improve the extraction yield of mycelium extract；
It isolates and purifies: final fermentation, extraction object is eluted with silica gel column chromatography, eluant, eluent selects petroleum ether-dichloromethane
Alkane-methanol；It is separated again with Sephadex LH-20 column chromatography, eluant, eluent is methylene chloride-methanol；Again with anti-with RP-18
Phase silica gel column chromatography is separated, and eluant, eluent is methanol-water；It is separated, is obtained from A.terreus times with high performance liquid chromatography again
The noval chemical compound of separation and Extraction in grade metabolite.
Embodiment 2:
The purposes of Aspergillus terreus secondary metabolite extract, made secondary metabolite are shown in Formulas I
Compound, its stereoisomer or pharmaceutically accessible salt, chemical structural formula are as follows:
The purposes of Aspergillus terreus secondary metabolite extract, the secondary metabolite extract
Preparation method includes strain fermentation, secondary metabolite extraction and isolates and purifies, specific steps are as follows:
Strain fermentation: the addition epigenetic modification adjusting control agent TSA into fungi culture medium, final concentration of 10 μM, 008%
Niacinamide, 0.1% two peptide, stir evenly, and stand, fermented and cultured 30 days, a common fermentation 60L；
Secondary metabolite extraction: after fermentation, with silk by mycelium and separation of fermentative broth；The bodies such as fermentation liquid addition
Long-pending ethyl acetate stirring extraction 3 times, ethyl acetate is concentrated under reduced pressure, fermentation liquid extract is obtained；The third of 80% is added in mycelium
Ketone-water, 2%2- methylalanine, 1% calcium citrate impregnate, and are crushed instrument with the ultrasonic tissue of power 800W, with ultrasonic 3s,
30min is then extracted by mycelium ultrasonication 45 times every the method for 3s, clear liquid is obtained with filtered on buchner funnel, depressurizes dense
Contracting is added isometric ethyl acetate and extracts 3 times, obtains fermentation mycelium extract；Merge fermentation liquid extract and fermented hypha
Body extract obtains final fermentation, extraction object；
It isolates and purifies: final fermentation, extraction object is eluted with silica gel column chromatography, eluant, eluent selects petroleum ether-dichloromethane
Alkane-methanol；It is separated again with Sephadex LH-20 column chromatography, eluant, eluent is methylene chloride-methanol；Again with anti-with RP-18
Phase silica gel column chromatography is separated, and eluant, eluent is methanol-water；It is separated, is obtained from A.terreus times with high performance liquid chromatography again
The noval chemical compound of separation and Extraction in grade metabolite.
Embodiment 3:
The purposes of Aspergillus terreus secondary metabolite extract, made secondary metabolite are shown in Formulas I
Compound, its stereoisomer or pharmaceutically accessible salt, chemical structural formula are as follows:
The purposes of Aspergillus terreus secondary metabolite extract, the secondary metabolite extract
Preparation method includes strain fermentation, secondary metabolite extraction and isolates and purifies, specific steps are as follows:
Strain fermentation: the addition epigenetic modification adjusting control agent TSA into fungi culture medium, final concentration of 10 μM, 0.1%
Niacinamide, 0.15% two peptide, stir evenly, and stand, fermented and cultured 30 days, a common fermentation 60L；
Secondary metabolite extraction: after fermentation, with silk by mycelium and separation of fermentative broth；The bodies such as fermentation liquid addition
Long-pending ethyl acetate stirring extraction 3 times, ethyl acetate is concentrated under reduced pressure, fermentation liquid extract is obtained；The third of 80% is added in mycelium
Ketone-water, 3%2- methylalanine, 15% calcium citrate impregnate, and are crushed instrument with the ultrasonic tissue of power 800W, with ultrasonic 3s,
Then the method for interval 3s extracts 30min for mycelium ultrasonication 45 times, obtain clear liquid with filtered on buchner funnel, depressurize dense
Contracting is added isometric ethyl acetate and extracts 3 times, obtains fermentation mycelium extract；Merge fermentation liquid extract and fermented hypha
Body extract obtains final fermentation, extraction object；
It isolates and purifies: final fermentation, extraction object is eluted with silica gel column chromatography, eluant, eluent selects petroleum ether-dichloromethane
Alkane-methanol；It is separated again with Sephadex LH-20 column chromatography, eluant, eluent is methylene chloride-methanol；Again with anti-with RP-18
Phase silica gel column chromatography is separated, and eluant, eluent is methanol-water；It is separated, is obtained from A.terreus times with high performance liquid chromatography again
The noval chemical compound of separation and Extraction in grade metabolite.
Comparative example 1:
Niacinamide, two peptide are not added in strain fermentation preparation step, rest part and embodiment 2 are completely the same.
Comparative example 2:
Epigenetic modification adjusting control agent TSA, rest part and embodiment 2 complete one are not added in strain fermentation preparation step
It causes.
Comparative example 3:
2- methylalanine, calcium citrate are not added in secondary metabolite extraction step, remaining and embodiment 2 complete one
It causes.
Embodiment 4:
Embodiment 2 is set as test group, comparative example 1, comparative example 2 and comparative example 3 are set to control group 1,2 and of control group
Control group 3 compares the weight of final fermentation, extraction object and secondary metabolite extract obtained, the results are shown in Table 1.
The weight of the final fermentation, extraction object of table 1 and Aspergillus terreus secondary metabolite extract
As shown in Table 1, test group and the final fermentation, extraction object weight of control group 3 are higher than control group 1, control group 2, explanation
The addition of niacinamide, two peptide, epigenetic modification adjusting control agent TSA can be improved the fermentation journey of Aspergillus terreus
Degree makes it generate more secondary metabolites；The weight of the secondary metabolite extract of test group is higher than control group 1, right
According to group 2, control group 3, illustrate that the addition of 2- methylalanine and calcium citrate can be improved mycelial extraction yield, control group 2
Secondary metabolite extract be 0, illustrate that the regulation of epigenetic modification adjusting control agent TSA makes Aspergillus terreus
Generate secondary metabolite extract.
Embodiment 5:
Scavenging ability of DPPH free radical test:
The secondary metabolite that secondary metabolite extract prepared by embodiment 2 is formulated as concentration 10mg/mL is extracted
Object solution；
Butylated hydroxytoluene (BHT) is configured to the BHT solution of concentration 10mg/mL；
1,1- diphenyl -2- picryl hydrazine is dissolved in ethyl alcohol, being configured to concentration is 1.5 × 10-4The DPPH ethanol solution of M；
Take the DPPH ethanol solution of 2500 μ L secondary metabolite extract solution, the BHT with the 500 above-mentioned preparations of μ L respectively
Solution concussion is uniformly mixed, and room temperature, which is protected from light, stands 30min, respectively as test group and control group；Utilize ultraviolet/vis spectroscopy light
Degree instrument measures the light absorption value of the test group and control group at wavelength 517nm.
Remove ABTS+Free radical aptitude tests
Secondary metabolite extract prepared by embodiment 2 is formulated as to the secondary metabolite extract of concentration 1mg/mL
Solution；
Butylated hydroxyanisol (BHA) is configured to the BHA solution of concentration 1mg/mL；
By the deionized water of 250 μ L, 500 μM of the hydrogenperoxide steam generator of 250 μ L, 250 μ L 1000 μM of ABTS solution
It with the peroxidase of the 8.8U/mL of 250 μ L, is uniformly mixed, is generated after 10min stable bluish-green with multipurpose test tube oscillator
Color ABTS+When radical cation, it is separately added into the secondary metabolite extract solution and BHA solution of the 250 above-mentioned preparations of μ L,
It is uniformly mixed with multipurpose test tube oscillator, reaction 10min is stood, respectively as test group and control group；Utilize immune ferment
Analyzer measures the light absorption value of the experimental group and control group at wavelength 410nm.
The power of Scavenging ability, is calculated with following formula respectively.Numerical value is higher to indicate that the ability for removing free radical is stronger.
Wherein, A1=DPPH test group light absorption value, A2=DPPH control group light absorption value；
Wherein, A3=ABTS+Test group light absorption value, A4=ABTS+Control group light absorption value；
2 DPPH free radical scavenging activity of table and ABTS+Free radical scavenging activity
| Classification | DPPH free radical scavenging activity (%) | ABTS+Free radical scavenging activity (%) |
| Secondary metabolite extract | 95.2 | 93.5 |
As shown in Table 2, secondary metabolite extract has good DPPH free radical scavenging activity and ABTS+Free radical is clear
Except rate, prompt Aspergillus terreus secondary metabolite extract that there is stronger antioxidant activity, it can be as system
The standby purposes for removing free radical biological agent.
Routine operation in operating procedure of the invention is well known to those skilled in the art, herein without repeating.
Technical solution of the present invention is described in detail in embodiment described above, it should be understood that the above is only
For specific embodiments of the present invention, it is not intended to restrict the invention, all any modifications made in spirit of the invention,
Supplement or similar fashion substitution etc., should all be included in the protection scope of the present invention.
Claims (7)
- The purposes of 1.Aspergillus terreus secondary metabolite extract, which is characterized in that the secondary metabolite Removing the purposes in free radical biological agent, wherein secondary metabolite is Formulas I compound represented, its stereoisomer Or the salt that pharmaceutically can contact, chemical structural formula are as follows:
- 2. the purposes of Aspergillus terreus secondary metabolite extract according to claim 1, feature exist In the preparation method of the Aspergillus terreus secondary metabolite extract includes the following steps:1) strain fermentation: adding epigenetic modification adjusting control agent TSA, niacinamide, two peptide into fungi culture medium, and stirring is equal It is even, it stands, fermented and cultured；2) secondary metabolite extracts: with silk by mycelium and separation of fermentative broth；Fermentation liquid is extracted with ethyl acetate；Mycelium 80% acetone-water, 2- methylalanine and calcium citrate is added, impregnates, historrhexis's instrument is broken, ultrasonic extraction, filtering, on Clear liquid is extracted with ethyl acetate；Combining extraction liquid is concentrated under reduced pressure, obtains final fermentation, extraction object；3) isolate and purify: final fermentation, extraction object successively uses silica gel column chromatography, Sephadex LH-20 column chromatography, RP-18 reverse phase The Aspergillus terreus cometabolism production that silica gel column chromatography, high performance liquid chromatography are isolated and purified to get purifying Object.
- 3. the purposes of Aspergillus terreus secondary metabolite extract according to claim 2, feature exist In the strain fermentation incubation time is 30 days.
- 4. the purposes of Aspergillus terreus secondary metabolite extract according to claim 2, feature exist In final concentration of 5-25 μM of the epigenetic modification adjusting control agent TSA.
- 5. the purposes of Aspergillus terreus secondary metabolite extract according to claim 2, feature exist In the additive amount of the niacinamide is 0.05-0.1%, and two peptide additive amount is 0.05-0.15%.
- 6. the purposes of Aspergillus terreus secondary metabolite extract according to claim 2, feature exist In the additive amount of the 2- methylalanine is the 1-3% of culture medium quality, and the additive amount of calcium citrate is culture medium quality 0.5-1.5%.
- 7. the purposes of Aspergillus terreus secondary metabolite extract according to claim 2, feature exist In the elution of the silica gel column chromatography, Sephadex LH-20 column chromatography, RP-18 reversed-phase silica gel column chromatography, high performance liquid chromatography Agent is successively are as follows: petroleum ether-methylene chloride-methanol, methylene chloride-methanol, methanol-water, methanol-water.
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| CN109053601A (en) * | 2018-09-04 | 2018-12-21 | 浙江海洋大学 | A kind of noval chemical compound LW-1 of the separation and Extraction from Aspergillus terreus secondary metabolite |
| CN110013477A (en) * | 2019-04-09 | 2019-07-16 | 嘉兴市爵拓科技有限公司 | A kind of new application of the secondary metabolites of Enteromorpha source fungi |
| CN110452940A (en) * | 2019-09-04 | 2019-11-15 | 台州职业技术学院 | A kind of separating and extracting process of the secondary metabolite of streptomycete |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109053601A (en) * | 2018-09-04 | 2018-12-21 | 浙江海洋大学 | A kind of noval chemical compound LW-1 of the separation and Extraction from Aspergillus terreus secondary metabolite |
| CN110013477A (en) * | 2019-04-09 | 2019-07-16 | 嘉兴市爵拓科技有限公司 | A kind of new application of the secondary metabolites of Enteromorpha source fungi |
| CN110452940A (en) * | 2019-09-04 | 2019-11-15 | 台州职业技术学院 | A kind of separating and extracting process of the secondary metabolite of streptomycete |
| CN110452940B (en) * | 2019-09-04 | 2021-03-30 | 台州职业技术学院 | Separation and extraction method of secondary metabolite of streptomycete |
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Application publication date: 20181221 |