CN115677634A - Monascus yellow pigment with anticancer function - Google Patents
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Abstract
The invention belongs to the field of compounds, and particularly relates to a monascus yellow pigment with an anticancer function. The specific technical scheme is as follows: provides a new monascus yellow pigment Monaspin A. Experiments prove that the compound has strong anticancer function and great potential to become anticancer drugs.
Description
Technical Field
The invention belongs to the field of compounds, and particularly relates to a monascus yellow pigment with an anticancer function.
Background
Natural products are the main sources of new drugs, such as anticancer, anti-inflammatory, antibacterial, etc. Therefore, the development of natural products with anticancer function is of great significance. The natural product can be used as medicine or precursor material, and can be used for preparing anticancer medicine or relevant research. Currently, about 50% of anticancer drugs are derived from natural products. Numerous studies have shown that the anticancer effects of natural compounds are multifaceted, mainly including: directly inhibiting cancer cell growth, resisting oxidation and free radical, blocking cancer cell division cycle, inducing tumor cell apoptosis, inhibiting protein kinase activity, inhibiting signal transduction, and inhibiting topoisomerase. Therefore, the discovery of novel anticancer natural compounds is of great significance.
Disclosure of Invention
The invention aims to provide monascus yellow pigment with an anticancer function.
In order to realize the purpose of the invention, the technical scheme adopted by the invention is as follows: a monascus yellow pigment has a molecular formula: c 15 H 18 O 4 The molecular structural formula is:
correspondingly, the preparation method of the monascus yellow pigment is obtained by fermenting monascus strains M7, wherein the monascus strains M7 are preserved in an important laboratory for collection and preservation of agricultural microbial resources of the Ministry of agriculture, and the preservation numbers are as follows: CCAM No.070120.
Preferably, after fermentation, the method for extracting the monascus yellow pigment comprises the following steps: soaking mycelium obtained after fermentation of the monascus strain M7 in HCl, extracting the mycelium by using an organic solvent to obtain a water phase-organic phase two-phase solution, separating and removing the water phase solution, removing pigment in the organic phase, drying and removing the organic solution.
Preferably, the organic solvent is a mixed solution of ethyl acetate and acetone.
Preferably, after fermentation, the method for extracting the monascus yellow pigment comprises the following steps: soaking the mycelium with HCl, washing the mycelium with clear water, filtering to collect mycelium, and mixing the mycelium with organic solvent.
Preferably, the mixture is obtained by mixing an organic solvent with the mycelium, heating the mixture to 60 ℃, performing shaking extraction, and filtering with a nylon filter cloth to remove the mycelium, thereby obtaining the aqueous phase-organic phase two-phase solution.
Preferably, the method for removing the pigment in the organic phase is: adding macroporous resin into the organic phase, and removing the pigment by shaking and adsorption.
Preferably, after fermentation, the method for extracting the monascus yellow pigment comprises the following steps: after removing the organic solution, the obtained product was redissolved with methanol to obtain a methanol solution, which was subjected to separation purification using a semi-preparative liquid chromatograph.
Correspondingly, the monascus yellow pigment is applied to the preparation of the anti-cancer drugs.
The invention has the following beneficial effects: the invention discovers and purifies Monaspin A from monascus which is homologous with traditional food and medicine to obtain a novel compound. The molecular structure is determined by NMR and LC-MS, and experiments prove that the compound has strong anticancer and bacteriostatic functions and has great potential of becoming an anticancer bacteriostatic medicament.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of Monaspin A;
FIG. 2 is a NMR carbon spectrum of Monaspin A.
Detailed Description
The invention provides a Monaspin A, C as a novel monascus yellow pigment 15 H 18 O 4 The molecular structural formula is as follows:
the Monaspin A has a strong anticancer function.
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. Unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art.
The first embodiment is as follows: preparation, extraction and identification of Monaspin A
1. Aspergillus strain M7 (agricultural microbial resource Collection and Collection laboratory Collection, collection number: CCAM No.070120, first published in Extremeophiles (2016) 20, cloning, expression and characterization of a novel protocol-active and organic solvent-yeast strain from Monascus ruber M7) was selected. It should be noted that the inventors tried a variety of monascus, and only Monaspin a was found and extracted in M7 at present.
Inoculating the monascus strain M7 to a fresh PDA culture medium, culturing for 10 days at 30 ℃, and washing monascus mycelia with sterile water to obtain monascus spore liquid. Diluting Monascus purpureus spore solution to 1 × 10 with sterile water 5 one/mL. Taking 2mL of diluted monascus spore liquid, inoculating into 30mL of fresh PDB culture medium, culturing for 15 days at 30 ℃ and 150rpm, filtering with a nylon filter screen, discarding the filtrate, and collecting mycelia.
2. Soaking the mycelium with 0.1mol/L HCl solution at 30 deg.C for 1 hr, filtering, and discarding filtrate to obtain mycelium. And washing the mycelium once with clear water to remove HCl adsorbed on the surface of the mycelium, and filtering to collect the mycelium. Mixing with wet mycelia with an organic solvent (ethyl acetate: acetone =3, volume ratio) to obtain a mixture; the ratio of organic solvent to wet mycelia was 30mL:1g of wet mycelia. The mixture was heated to 60 ℃ and extracted with shaking at 50rpm for 3 hours. Filtering with nylon filter cloth to remove mycelium to obtain water phase-organic phase two-phase solution. The two-phase solution was separated using a separatory funnel and the aqueous phase was discarded to obtain an organic phase. Then, 3g of wet macroporous resin (model LSA-7) was added to about 30mL of the obtained organic solvent, and the resin was shaken at 30 ℃ and 50rpm to adsorb most of the pigment molecules. Then filtering to remove resin particles to obtain organic solvent, concentrating organic solvent in organic phase to 1/10 volume by vacuum distillation, and adding anhydrous Na 2 SO 4 The water was removed, and then the whole organic solution was distilled off under reduced pressure to obtain a solid. The resulting solid was dissolved with methanol to obtain a methanol solution.
3. Separating and purifying the methanol solution by using a semi-preparative liquid chromatograph. A semi-preparative liquid chromatograph model was Waters, U.S.A., and a semi-preparative column was Inertsil ODS-3 (250 mm. Times.10mm, 5 μm). The prepared sample solution was added to the injection port at a flow rate of 3mL/min in a sample introduction amount of 100 μ L, with methanol and water as mobile phases, and the initial mobile phase ratio methanol: water =1, column temperature 25 ℃, PDA detector. And determining a product peak through retention time, and collecting an elution component in time to obtain a Monaspin A sample with the purity of more than 95%. The sample was dried with a nitrogen blower to obtain 84. Mu.g of yellow solid powder.
4. The structure of the compound is identified by using NMR (nuclear magnetic resonance) and GC-MS (gas chromatography-mass spectrometer) technologies, wherein a nuclear magnetic resonance hydrogen spectrum is shown in figure 1, and a nuclear magnetic resonance carbon spectrum is shown in figure 2.
Example two: monaspin A anticancer effect display
1. The effect of inhibiting the growth of cancer cells is shown.
The liver cancer cell strain QGY-7701 and the lung cancer cell line SPC-A-1 are selected as the subjects of the experiment for testing the inhibition of the growth of the cancer cells by Monaspin A. Inoculating the two cancer cell lines into RPMI-1640 medium (purchased from Saimer Feishell science, inc.) respectively, and adding CO at 37 deg.C and 5% 2 Incubate at constant temperature for log phase, collect cells by centrifugation, resuspend cells with buffer, add 96-well plate, 180 μ L each (about 6000 cells/well). Placing the 96-well plate in a constant temperature incubator, at 37 deg.C, 5% 2 After 14h of incubation under the same conditions, monaspin A (5, 10, 15 or 20. Mu.M) was added to different wells at different concentrations and incubation was continued for 24h under the same conditions.
In each well, 100. Mu.L of cell-free supernatant was carefully removed, and 90. Mu.L of fresh serum medium and 10. Mu.L of MTT reagent were added, mixed well and cultured for an additional 4 hours. Again, 110. Mu.L of cell-free supernatant was removed, followed by addition of 110. Mu.L of Formazan reagent and shaking at low speed for 10 minutes to allow complete mixing. Finally, the absorbance of each well was measured at 490nm and the concentration that inhibited 50% of the cancer cell growth, i.e., the median inhibitory concentration (IC 50), was calculated. The results showed that Monaspin A had an IC50 value of 11.10. Mu.M for the liver cancer cell line QGY-7701 and an IC50 value of 12.54. Mu.M for the lung cancer cell line SPC-A-1, and showed strong cancer cell inhibitory effect.
2. And (5) animal experiments for displaying the anti-cancer effect.
SD rats, weighing about 200g, purchased from Shanghai slyke laboratory animals Co., ltd, were used and one week after adaptive feeding, rats were induced to develop liver tumors by feeding water containing Diethylnitrosamine (DEN). Rats were selected for 14 weeks of DEN induction, with 10 non-significantly different rats per group, and randomized into the following groups: (1) control (blank, no drug); (2) Monaspin group A (2 mg/kg). The drug was administered once a week with feed for four weeks. At week 19, each group of rats was sacrificed and tissue specimens were obtained. According to the liver dissection results, compared with the control group, the Monaspin A group rat liver has less tumors (tumor masses with diameters of more than 0.5 cm), about 60% of the control group, and smaller tumor volume, about 50% of the control group. Monaspin A was demonstrated to significantly inhibit tumor growth in rats.
Example three: monaspin A antibacterial effect display
For the bacteria, a loop of the inoculum solution was picked from the glycerol storage tube and inoculated into 10mL of LB medium. Then, the strain was placed in an incubator and cultured with shaking at 37 ℃ and 180rpm for 18 hours to place the strain in the logarithmic phase of growth. Then, 1mL of the bacterial solution was diluted with fresh LB medium, and the absorbance (OD) at 620nm of the bacterial solution was measured 620 ) Adjusting the concentration of bacterial solution to OD 620 The concentration of the bacteria liquid is between 0.09 and 0.11, and the concentration of the bacteria liquid is about 5 multiplied by 10 at the moment 8 CFU/mL. For filamentous fungi, the strain is inoculated on a PDA culture medium and cultured for 5 to 10 days at the temperature of 30 ℃ until the diameter of a colony is more than 2cm. Then inoculating the pre-cultured strain on a fresh PDA culture medium, culturing for 5-10 days at 30 ℃, and washing the mycelium with sterile water to obtain a spore solution. Diluting the spore liquid with sterile water, and detecting the concentration of the spore liquid with a blood counting chamber under microscope 5 one/mL.
198. Mu.L of bacterial liquid or filamentous fungal spore liquid is taken by a sterile pipette and added to one well of a 96-well plate, then 2. Mu.L of Monaspin A solution (2.0 mg/mL) is added to the first well and mixed uniformly by shaking, and the concentration of Monaspin A in the well is 20. Mu.g/mL. Using this dilution method, 5 treatments were set with Monaspin A concentrations of 20, 10, 5, 2.5 and 1.25. Mu.g/mL, respectively. And setting a negative control group: mu.L of methanol was added to 198. Mu.L of the bacterial suspension or spore suspension. After a 96-well plate for bacterial inhibition experiments was placed in an incubator at 37 ℃ for 24 hours, absorbance was measured at 620nm using a microplate reader, and the minimum monasp in a case where growth of a microorganism was completely inhibited and no regeneration occurred was the Minimum Inhibitory Concentration (MIC) of monasp in a case where the microorganism was completely inhibited. As a result, the MICs of Monaspin A on Escherichia coli, pseudomonas aeruginosa, staphylococcus aureus and Salmonella are respectively 11.2 mug/mL, 20.1 mug/mL, 17.4 mug/mL and 5.8 mug/mL; MICs for Aspergillus flavus, aspergillus fumigatus, and Aspergillus nidulans were 30.3. Mu.g/mL, 26.8. Mu.g/mL, and 25.4. Mu.g/mL, respectively. Has obvious bacterial and fungal growth inhibiting effect.
The above-described embodiments are only intended to describe the preferred embodiments of the present invention, and not to limit the scope of the present invention, and various modifications, variations, modifications, and substitutions which may be made by those skilled in the art to the technical solution of the present invention without departing from the spirit of the present invention are intended to fall within the scope of the present invention defined by the claims.
Claims (9)
1. A monascus yellow pigment is characterized in that: the molecular formula is: c 15 H 18 O 4 The molecular structural formula is:
2. the process for preparing monascus yellow pigment according to claim 1, wherein: the strain is prepared by fermenting an aspergillus erythraea strain M7, wherein the aspergillus erythraea strain M7 is preserved in an agricultural microorganism resource collection and preservation key laboratory of Ministry of agriculture, and the preservation number is as follows: CCAM No.070120.
3. The process for preparing monascus yellow pigment according to claim 2, wherein: after fermentation, the method for extracting the monascus yellow pigment comprises the following steps: soaking mycelium obtained after fermentation of the monascus strain M7 with HCl, extracting the mycelium with an organic solvent to obtain a water phase-organic phase two-phase solution, separating to remove a water phase solution, removing pigment impurities in the organic phase, drying, and removing the organic solution.
4. The method for preparing monascus yellow pigment according to claim 3, wherein the method comprises the following steps: the organic solvent is a mixed solution of ethyl acetate and acetone.
5. The method for preparing monascus yellow pigment according to claim 3, wherein the method comprises the following steps: after fermentation, the method for extracting the monascus yellow pigment comprises the following steps: soaking the mycelium with HCl, washing the mycelium with clear water, filtering to collect mycelium, and mixing the mycelium with organic solvent.
6. The process for preparing monascus yellow pigment according to claim 3, wherein: mixing organic solvent and mycelium to obtain mixture, heating the mixture to 60 ℃, performing oscillation extraction, and filtering by using nylon filter cloth to remove the mycelium to obtain the water phase-organic phase two-phase solution.
7. The process for preparing monascus yellow pigment according to claim 3, wherein: the method for removing the pigment in the organic phase comprises the following steps: and adding macroporous resin into the organic phase, and removing the pigment by shaking adsorption.
8. The method for preparing monascus yellow pigment according to claim 3, wherein the method comprises the following steps: after fermentation, the method for extracting the monascus yellow pigment comprises the following steps: after removing the organic solution, the obtained product was redissolved with methanol to obtain a methanol solution, which was subjected to separation purification using a semi-preparative liquid chromatograph.
9. The use of the monascus yellow pigment of claim 1 in the preparation of an anti-cancer medicament.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101862324A (en) * | 2010-04-13 | 2010-10-20 | 福州大学 | Application of monascus color components and derivatives thereof in fighting cancers |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101862324A (en) * | 2010-04-13 | 2010-10-20 | 福州大学 | Application of monascus color components and derivatives thereof in fighting cancers |
Non-Patent Citations (4)
| Title |
|---|
| HAILUN GUO ET AL.: "Cloning, expression and characterization of a novel cold‑active and organic solvent‑tolerant esterase from Monascus ruber M7", 《EXTREMOPHILES》, vol. 20, pages 451 - 459 * |
| 孙艳君 等: "红曲霉的分离鉴定及红曲色素的测定", 《中共酿造》, no. 226, pages 52 - 54 * |
| 徐菲菲 等: "液态发酵红曲黄色素粗提物色素组分的分离纯化与鉴定", 《食品与发酵工业》, vol. 46, no. 1, pages 91 - 98 * |
| 王小莉 等: "红曲菌菌株 M7 的生物学特性研究", 《中国热带医学》, vol. 5, no. 6, pages 1349 - 1350 * |
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