CN114315741B - Thio compound and preparation method and application thereof - Google Patents
Thio compound and preparation method and application thereof Download PDFInfo
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- CN114315741B CN114315741B CN202210061429.6A CN202210061429A CN114315741B CN 114315741 B CN114315741 B CN 114315741B CN 202210061429 A CN202210061429 A CN 202210061429A CN 114315741 B CN114315741 B CN 114315741B
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Abstract
The invention discloses a thio compound, a preparation method and application thereof, wherein the thio compound has a structure shown in any one of formulas 1-6 and is obtained by separating and purifying fermentation products of cave fungi. The preparation method is characterized in that the cave fungi Aspergillus fumigatus GZWMJZ-152 are adopted, and the thio compound is obtained through extraction and monomer separation and purification after fermentation in a solid state fermentation mode. Pharmacological experiments show that the compounds have an antioxidant effect and can be applied to preparation of antioxidant stress pharmaceutical preparations.
Description
Technical Field
The invention belongs to the field of biological medicine, and in particular relates to a thio compound, a preparation method and application thereof.
Background
Sulfur atoms are widely present in polypeptides, proteins and small molecule compounds, and have important biological roles. The sulfur-containing natural product is a special active compound which has been isolated from plants, microorganisms and animals and has wide biological activity, and part of the compounds are used clinically in batches, such as tenoxicam, trabectedin, edoxaban and the like. Recently, some sulfur-containing compounds with new skeletons have been separated from secondary metabolites of microorganisms, greatly enriching the structural types of natural products. The cave microorganism has special living environment which is not possessed by general soil microorganism, is free from illumination, moist and relatively barren in nutrition, and meanwhile, the methane content in the atmosphere of the cave is high, and the extreme environment can influence the metabolic pathway of the cave microorganism so as to generate active compounds with novel structures. The key point of the patent is that the inventor obtains 6 sulfur-containing compounds with novel structures through separation and identification in the continuous research of cave fungi Aspergillusfumigatus GZWMJZ-152, and the sulfur-containing compounds have remarkable antioxidant activity. Oxidative stress is a negative effect produced in vivo by free radicals and is considered to be an important factor in causing aging and diseases. Thus, the discovery of antioxidant active molecules is of great importance in combating oxidative stress-type diseases.
Disclosure of Invention
The invention aims to extract, separate and purify the thio-compound from the fermentation product of the cave fungi, has the antioxidation effect, and can be applied to antioxidation stress drugs. Provided are a thio compound, a preparation method and application thereof. The aim and the main technical problems are achieved by adopting the following technical scheme: a thio compound having a structure represented by any one of formulas 1 to 6:
the preparation method of the compounds 1-6 comprises the following steps:
strain a preparation: 200-300 parts of potato, 20-25 parts of glucose and 15-20 parts of agar, adding into 1L of purified water, adjusting the pH value to 6.5-7.5, preparing an inclined plane, inoculating Aspergillus fumigatus GZWMJZ-152 mycelium at normal temperature, and culturing for 3 days at 28-35 ℃ to obtain a strain;
b, inoculating: filling 50-100 parts of rice and 50-100 parts of purified water into each conical flask by adopting a solid fermentation mode, inoculating the strain obtained in the step A, and performing stationary culture at 28 ℃ for 30 days to obtain a fermentation culture medium;
c, extraction: soaking the fermentation medium in the step B for 48-72 hours with ethyl acetate, extracting for 3-5 times with a stirrer for 30-40 minutes each time, combining the supernatants, and recovering ethyl acetate in a rotary evaporator to obtain crude extract;
d, monomer separation and purification: c, separating the crude extract obtained in the step C through column chromatography to obtain compounds 1-6; the chromatographic separation method comprises silica gel column chromatography, gel column chromatography and semi-preparative high performance liquid chromatography.
The application of the thio compound in the preparation of drugs for resisting oxidative stress.
A pharmaceutical composition comprising a thio compound of any one of formulae 1 to 6 and a pharmaceutically acceptable adjuvant.
The pharmaceutical composition contains 0.1-99% by mass of a thio compound containing any one of the structural formulas 1-6, and the balance of a medicinal carrier or excipient.
In the continuous research of the cave fungus Fumigatus GZWMJZ-152, the inventor performs more systematic research on the extraction, separation and purification of fermentation products of the cave fungus, and 6 novel thio compounds 1-6 are obtained. The prepared thio compound has an antioxidation effect and can be applied to antioxidation stress drugs.
Drawings
FIG. 1 is a structural formula of the compounds 1 to 6 of the present invention
FIG. 2 is a high resolution mass spectrum of Compound 1 of the present invention
FIG. 3 is a high resolution mass spectrum of Compound 2 of the present invention
FIG. 4 is a high resolution mass spectrum of Compound 3 of the present invention
FIG. 5 is a high resolution mass spectrum of Compound 4 of the present invention
FIG. 6 is a high resolution mass spectrum of Compound 5 of the present invention
FIG. 7 is a high resolution mass spectrum of Compound 6 of the present invention
FIG. 8 is a nuclear magnetic resonance hydrogen spectrum of Compound 1 of the present invention
FIG. 9 is a nuclear magnetic resonance hydrogen spectrum of Compound 2 of the present invention
FIG. 10 is a nuclear magnetic resonance hydrogen spectrum of Compound 3 of the present invention
FIG. 11 is a nuclear magnetic resonance hydrogen spectrum of Compound 4 of the present invention
FIG. 12 is a nuclear magnetic resonance hydrogen spectrum of Compound 5 of the present invention
FIG. 13 is a nuclear magnetic resonance hydrogen spectrum of Compound 6 of the present invention
FIG. 14 is a nuclear magnetic resonance carbon spectrum of Compound 1 of the present invention
FIG. 15 is a nuclear magnetic resonance carbon spectrum of Compound 2 of the present invention
FIG. 16 is a nuclear magnetic resonance carbon spectrum of Compound 3 of the present invention
FIG. 17 is a nuclear magnetic resonance carbon spectrum of Compound 4 of the present invention
FIG. 18 is a nuclear magnetic resonance carbon spectrum of Compound 5 of the present invention
FIG. 19 is a nuclear magnetic resonance carbon spectrum of Compound 6 of the present invention
Detailed Description
Example 1:
preparation of Compounds 1-6
(1) Preparation of the seed
The components of the purification medium used were: 200 parts of potato, 20 parts of glucose, 20 parts of agar and 1L of purified water. Sterilizing at high temperature, making into inclined plane, standing at 28deg.C, inoculating mycelium of fungi Aspergillusfumigatus GZWMJZ-152, and culturing at normal temperature.
(2) Inoculation of
100 conical flasks are prepared by adopting a solid fermentation mode, 100 parts of rice and 100 parts of purified water are filled into each conical flask, the strains are inoculated after high-temperature sterilization for 30min at 121 ℃, and the culture is carried out for 30 days at 28 ℃.
(3) Extraction
Soaking the fermentation broth and mycelium obtained by the fermentation in ethyl acetate for 48 hours, and then stirring and extracting the fermentation broth and mycelium in batches by using a stirrer for three times each for 30 minutes. After standing, the supernatant was combined and ethyl acetate was recovered in a rotary evaporator to obtain 620.1 g of a crude extract.
(4) Monomer separation and purification
Dissolving the crude extract, mixing with 100-200 mesh silica gel, performing silica gel column chromatography, gradient eluting with petroleum ether/ethyl acetate (0-100%) and dichloromethane/methanol (0-50%), detecting by TLC, and mixing the same components to obtain 7 components. And subjecting the component 3 to silica gel column chromatography, petroleum ether/dichloromethane gradient elution (25% -50%), TLC detection, and combining the same components to obtain 5 components. The 3-3 fractions were subjected to gel column chromatography (methanol column), TLC detection, and the same fractions were combined to give 3 fractions in total, and the 3-3-2 fractions were separated by semi-preparative high performance liquid chromatography (60% methanol/water) to give compound 2 (10.8 mg). The component 4 is subjected to silica gel column chromatography, dichloromethane/methanol gradient elution (0-60%), TLC detection is carried out, and the same components are combined to obtain 7 components in total. The fractions 4-2 were subjected to gel column chromatography (methanol column), TLC detection, and the same fractions were combined to give 7 fractions in total, and the 4-2-7 fractions were separated by semi-preparative high performance liquid chromatography (65% methanol/water) to give Compound 3 (5.2 mg) and Compound 4 (4.5 mg). Fractions 4-7 were subjected to gel column chromatography (methanol column), TLC detection, and the same fractions were combined to give 10 fractions in total, and the 4-7-10 fractions were separated by semi-preparative high performance liquid chromatography (45% methanol/water, 0.15% trifluoroacetic acid) to give Compound 5 (9.6 mg) and Compound 6 (3.2 mg). Component 7 was subjected to gel column chromatography (methanol column), TLC detection, and the same components were combined to give 4 components in total, and 7-4 components were separated by semi-preparative high performance liquid chromatography (55% methanol/water) to give compound 1 (14.2 mg).
Structural identification of Compounds 1-6
The structure of the compounds 1-6 is determined by comprehensively analyzing data such as high-resolution mass spectrum, ultraviolet spectrum, infrared spectrum, optical rotation, nuclear magnetic resonance and the like, and the physicochemical properties are as follows:
compound 1: a pale yellow powder; molecular formula C 23 H 24 O 9 N 2 S, S; molecular weight 504; UV (MeOH) lambda max (logε)207(3.29),288(2.75)nm；IR(KBr)ν max 3356,2357,2335,1739,1692,1632,1580,1436,1344,1261,1213,1105,1089,1024,821,669cm -1 ；HRESIMS m/z 527.1098[M+Na] + (calculated for C 23 H 24 O 9 N 2 NaS,527.1095)；[α] D 20 -60.3 (c 0.7), whose nmr hydrogen spectrum and nmr carbon spectrum data are shown in table 1.
Compound 2: pale yellow crystals; molecular formula C 19 H 20 O 8 S, S; molecular weight 408; UV (MeOH) lambda max (logε)220(3.22),290(2.95)nm；IR(KBr)ν max 3421,2357,2341,1725,1625,1592,1454,1367,1336,1284,1110,1094,1025,965,821,667cm -1 ；HRESIMS m/z 407.0807[M–H] – (calculated for C 19 H 19 O 8 S, 407.0795), and nmr hydrogen spectrum and nmr carbon spectrum data thereof are shown in table 1.
Compound 3: colorless crystals; molecular formula C 21 H 22 O 8 S, S; molecular weight 434; UV (MeOH) lambda max (logε)202(3.81),287(3.31),350(2.94)nm；IR(KBr)ν max 3436,2357,2339,1719,1629,1584,1461,1367,1309,1270,1220,1193,1112,1085,1037,987,835,667cm -1 ；HRESIMS m/z 457.0925[M+Na] + (calculated for C 21 H 22 O 8 NaS, 457.0928), and nmr hydrogen spectrum and nmr carbon spectrum data thereof are shown in table 1.
Compound 4: colorless crystals; molecular formula C 21 H 22 O 9 S, S; a molecular weight of 450; UV (MeOH) lambda max (logε)208(3.64),288(3.14)nm；IR(KBr)ν max 3127,2357,2342,1724,1669,1633,1585,1436,1367,1321,1220,1151,1110,1093,1022,927,825,669cm -1 ；HRESIMS m/z 473.0879[M+Na] + (calculated for C 21 H 22 O 9 NaS, 473.0877), and nmr hydrogen spectrum and nmr carbon spectrum data thereof are shown in table 1.
Compound 5: colorless crystals; molecular formula C 9 H 9 O 3 NS; a molecular weight 211; UV (MeOH) lambda max (logε)215(3.12),230(3.07),280(2.71)nm；IR(KBr)ν max 3270,1587,1494,1449,1429,1342,1276,1115,1071,1005,919,901,830,749cm -1 ；HRESIMS m/z 210.0217[M-H] - (calculated for C 9 H 8 O 3 NS, 210.0219), and nmr hydrogen spectrum and nmr carbon spectrum data thereof are shown in table 2.
Compound 6: white powder; molecular formula C 10 H 11 O 4 NS; a molecular weight 241; UV (MeOH) lambda max (logε)220(3.11),230(3.09),285(2.78)nm；IR(KBr)ν max 3362,1593,1494,1461,1432,1352,1217,1183,1127,1083,1054,1006,869,756cm -1 ；HRESIMS m/z 240.0330[M-H] - (calculated for C 10 H 10 O 4 NS, 240.0325), and nmr hydrogen spectrum and nmr carbon spectrum data thereof are shown in table 2.
TABLE 1 Nuclear magnetic resonance Hydrogen Spectroscopy and carbon Spectroscopy data for Compounds 1-4 (DMSO-d 6 )
TABLE 2 Nuclear magnetic resonance Hydrogen Spectroscopy and carbon Spectroscopy data for Compounds 5 and 6 (DMSO-d 6 )
Example 2
In order to further verify the beneficial effects of the compounds synthesized by the present invention, the antioxidant activity test was performed on compounds 1-6, as follows:
the experiment uses DPPH method to test the free radical scavenging ability of the compound, ORAC method to test the oxidation resistance index of the compound, and PC12 cell to test the protection ability of the compound against oxidation damage.
The DPPH method test method comprises the following steps: DPPH solution a (0.15 mmol/L) and sample solution b were prepared using methanol as a solvent. Setting a 'sample control well' (160 muLb+40 muL of methanol), 'negative control well' (160 muL of methanol+40 mu L a), 'sample+DPPH well' (160 muLb+40 mu L a), positive control is Vit C; the OD value is measured by an enzyme-labeled instrument at the wavelength of 517nm, and the clearance is calculated as follows: clearance = [ OD ] Negative control -(OD Sample +DPPH -OD Sample control )]/OD Negative control ×100％
The ORAC method test method comprises the following steps: the test mainly comprises the steps of using 0.153mol/L of 2,2' -azobisisobutylaminidine hydrochloride solution (AAPH), 81.6nmol/L of fluorescein solution (FL), 5 series of positive control drug Trolox (concentration 50, 25, 12.5, 6.25 and 3.125 mu mol/L) and a sample to be tested, dissolving the solvent by using 75mmol/LpH of 7.4 phosphate buffer (PBS buffer), setting a negative control group, a blank control group, a positive control group and a sample to be tested in a 96-well plate, adding 25 mu L of PBS buffer, trolox and sample to be tested in each group, adding 150 mu L of FL in each group, placing the added 96-well plate into an incubator at 37 ℃, incubating for 10min, taking out, adding 25 mu L of PBS buffer in the other groups, immediately placing the solution into a multifunctional enzyme-labeled instrument to detect fluorescence, setting the excitation wavelength to be 485nm, and detecting for about 1h every time at 530 nm. The relative fluorescence intensity f is equal to the ratio of the measured fluorescence value to the initial fluorescence value, and the area under the fluorescence decay curve (AUC) is calculated by using an approximate integration method with the relative fluorescence intensity. The formula is as follows: auc=0.5+f1+ & gt. Fi+ & gt+f59+0.5 f60, where f i The relative fluorescence intensity measured at time i minutes is shown. Net AUC is the difference between the sample AUC and the blank AUCValues. Regression equation of netAUC was performed at time t of Trolox fluorescence measurement, Y # netAUC )＝aX( μM ) +b. The final ORAC values were calculated using the regression equation between Trolox concentration and net AUC and expressed as Trolox equivalent per micromolar sample in μmol TE/μmol. The formula is as follows:
relative ORAC value = [ (AUC) Sample of -AUC Blank space )/(AUC Trolox -AUC Blank space )]* (Trolox molar concentration. Mu. Mol/L)/(sample molar concentration. Mu. Mol/L)
The PC12 cell oxidative damage protection test method comprises the following steps: PC-12 cells were prepared as a cell suspension in a culture medium containing 10% fetal bovine serum, and 100. Mu.L of 1X 10 cells were inoculated per well in a 96-well plate 5 Cells in 5% CO/mL 2 Pre-culturing for 24 hours at 37 ℃. After dissolving the sample in DMSO, diluting the sample with basal medium (RPMI-1640) (10. Mu.M), sucking out the old medium, adding 100. Mu.L of sample solution into each well, and setting 3 compound wells for each concentration at a final concentration of 10. Mu.M; culturing in incubator for 16 hr. Aspiration of old medium, addition of 100. Mu.L of basal medium (RPMI-1640) per well of drug-toxic well, addition of 100. Mu.L of hydrogen peroxide solution (5. Mu.M) per well of oxidative stress well, and addition of 5% CO at 37 ℃C 2 Culturing was continued for 4 hours. After aspiration of the old medium, 100. Mu.L CCK-8 solution diluted ten times with DMEM was directly added to each well at 37℃with 5% CO 2 Culturing was continued for 2 hours (light-shielding operation). The absorbance at 450nm was measured with an enzyme-labeled instrument, the results were recorded, and the experimental results were expressed as.+ -. SD. The results of the antioxidant test are shown in Table 3
TABLE 3 antioxidant Activity of Compounds 1-6 (IC 50 )
a Cell survival rate 46.91 +/-3.74% of hydrogen peroxide damage model group
These examples should be construed as merely illustrative of the present invention and not limiting the scope of the present invention. Various changes and modifications to the present invention may be made by one skilled in the art after reading the description herein, and such equivalent changes and modifications are intended to fall within the scope of the present invention as defined in the appended claims.
Claims (5)
1. A thio compound characterized by having a structure represented by any one of formulas 2 to 6
2. A process for the preparation of the thio compound as claimed in claim 1 comprising the steps of:
strain a preparation: 200-300 parts of potato, 20-25 parts of glucose and 15-20 parts of agar, adding into 1L of purified water, adjusting the pH value to 6.5-7.5, preparing an inclined plane, inoculating mycelium of cave fungi Aspergillusfumigatus GZWMJZ-152 at normal temperature, and culturing for 3 days at 28-35 ℃ to obtain a strain;
b, inoculating: filling 50-100 parts of rice and 50-100 parts of purified water into each conical flask by adopting a solid fermentation mode, inoculating the strain obtained in the step A, and performing stationary culture at 28 ℃ for 30 days to obtain a fermentation culture medium;
c, extraction: soaking the fermentation medium in the step B for 48-72 hours with ethyl acetate, extracting for 3-5 times with a stirrer for 30-40 minutes each time, combining the supernatants, and recovering ethyl acetate in a rotary evaporator to obtain crude extract;
d, monomer separation and purification: c, separating the crude extract obtained in the step C through column chromatography to obtain compounds 2-6; the chromatographic separation method comprises silica gel column chromatography, gel column chromatography and semi-preparative high performance liquid chromatography.
3. Use of a thio compound as claimed in claim 1 for the preparation of a medicament against oxidative stress.
4. A pharmaceutical composition comprising the thio compound of claim 1 and a pharmaceutically acceptable excipient.
5. The pharmaceutical composition according to claim 4, wherein the pharmaceutical composition comprises 0.1-99% by mass of the thio compound of claim 1, the balance being a pharmaceutically acceptable carrier or excipient.
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Citations (4)
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| US6441244B1 (en) * | 1999-01-12 | 2002-08-27 | Clariant Finance (Bvi) Limited | Benzophenones and the use thereof as photoinitiators |
| CN101875601A (en) * | 2010-02-22 | 2010-11-03 | 中国海洋大学 | Cresylol trimer compounds and its production and use |
| CN109809971A (en) * | 2019-03-02 | 2019-05-28 | 中国科学院昆明植物研究所 | Poly benzylidene derivative and its pharmaceutical composition and preparation method and its application |
| WO2020026583A1 (en) * | 2018-07-30 | 2020-02-06 | Jnc株式会社 | Liquid crystal compound comprising benzothiazole ring and cf2o ligand, liquid crystal composition, and liquid crystal display element |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP3274347B1 (en) * | 2015-03-26 | 2020-07-08 | Giuliani S.p.A. | Compounds having antioxidant activity against free radicals and anti-inflammatory activity, and corresponding pharmaceutical compositions for skin care |
| TWI754702B (en) * | 2016-12-28 | 2022-02-11 | 德商Ｕｃｂ製藥有限公司 | (aza)indole- and benzofuran-3-sulfonamides |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6441244B1 (en) * | 1999-01-12 | 2002-08-27 | Clariant Finance (Bvi) Limited | Benzophenones and the use thereof as photoinitiators |
| CN101875601A (en) * | 2010-02-22 | 2010-11-03 | 中国海洋大学 | Cresylol trimer compounds and its production and use |
| WO2020026583A1 (en) * | 2018-07-30 | 2020-02-06 | Jnc株式会社 | Liquid crystal compound comprising benzothiazole ring and cf2o ligand, liquid crystal composition, and liquid crystal display element |
| CN109809971A (en) * | 2019-03-02 | 2019-05-28 | 中国科学院昆明植物研究所 | Poly benzylidene derivative and its pharmaceutical composition and preparation method and its application |
Non-Patent Citations (1)
| Title |
|---|
| Yanchao Xu,et al..Sulfur-Containing Phenolic Compounds from the Cave Soil-Derived Aspergillus fumigatus GZWMJZ-152.《J. Nat. Prod.》.2022,第85卷第433-440页. * |
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