CN108558817B - A kind of isocoumarin derivatives and preparation method and use thereof - Google Patents
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- 125000003151 isocoumarinyl group Chemical class C1(=O)OC(=CC2=CC=CC=C12)* 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 96
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000287 crude extract Substances 0.000 claims abstract description 14
- 238000000855 fermentation Methods 0.000 claims abstract description 11
- 230000004151 fermentation Effects 0.000 claims abstract description 11
- 238000004440 column chromatography Methods 0.000 claims abstract description 8
- 238000000926 separation method Methods 0.000 claims abstract description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000746 purification Methods 0.000 claims abstract description 4
- 239000000741 silica gel Substances 0.000 claims abstract description 4
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 4
- 239000000284 extract Substances 0.000 claims abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000003480 eluent Substances 0.000 claims description 12
- 239000001963 growth medium Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 241000209094 Oryza Species 0.000 claims description 9
- 235000007164 Oryza sativa Nutrition 0.000 claims description 9
- 239000012046 mixed solvent Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 235000009566 rice Nutrition 0.000 claims description 9
- 238000010828 elution Methods 0.000 claims description 7
- 241000122818 Aspergillus ustus Species 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- 239000012153 distilled water Substances 0.000 claims description 6
- 239000002609 medium Substances 0.000 claims description 6
- 238000004321 preservation Methods 0.000 claims description 6
- 238000004007 reversed phase HPLC Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 238000009630 liquid culture Methods 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000401 methanolic extract Substances 0.000 claims description 4
- 238000010898 silica gel chromatography Methods 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- 244000061456 Solanum tuberosum Species 0.000 claims description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 claims description 3
- 239000000499 gel Substances 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- 238000002386 leaching Methods 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 2
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- 229940050176 methyl chloride Drugs 0.000 claims 1
- 230000002829 reductive effect Effects 0.000 abstract description 6
- 238000001914 filtration Methods 0.000 abstract description 3
- 238000002953 preparative HPLC Methods 0.000 abstract description 2
- 208000024891 symptom Diseases 0.000 abstract description 2
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000002538 fungal effect Effects 0.000 abstract 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 9
- 230000003078 antioxidant effect Effects 0.000 description 8
- 238000002835 absorbance Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 4
- 229930003268 Vitamin C Natural products 0.000 description 4
- -1 chlorine aromatic compound Chemical class 0.000 description 4
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 4
- 230000007760 free radical scavenging Effects 0.000 description 4
- 235000019154 vitamin C Nutrition 0.000 description 4
- 239000011718 vitamin C Substances 0.000 description 4
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 2
- 240000006439 Aspergillus oryzae Species 0.000 description 2
- 235000002247 Aspergillus oryzae Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 230000002292 Radical scavenging effect Effects 0.000 description 2
- 238000000540 analysis of variance Methods 0.000 description 2
- 230000003064 anti-oxidating effect Effects 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 235000012015 potatoes Nutrition 0.000 description 2
- 238000012599 radical scavenging assay Methods 0.000 description 2
- 230000003716 rejuvenation Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000001026 1H--1H correlation spectroscopy Methods 0.000 description 1
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
- 238000002114 high-resolution electrospray ionisation mass spectrometry Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/76—Benzo[c]pyrans
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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Abstract
本发明公开了一种异香豆素类衍生物及其制备方法和用途，特点是该异香豆素类衍生物的结构式如Ⅰ所示，其制备方法步骤包括通过保藏号为CCTCC No:M2014086的海洋真菌发酵培养获取含有异香豆素类衍生物的发酵物，然后加入甲醇浸泡超声过滤，蒸干，再用乙酸乙酯萃取后蒸干，得粗浸膏，将该提取物经减压硅胶柱层析、反相中压柱层析，最后反相半制备高效液相色谱分离纯化得到，该异香豆素类衍生物具有抗氧化作用，优点是化合物I具有清除自由基能力，可能用于延迟阿尔茨海默病的发病并且有助于缓解其症状。
The invention discloses an isocoumarin derivative, a preparation method and application thereof, and is characterized in that the structural formula of the isocoumarin derivative is shown in I, and the preparation method steps include the steps of passing through the ocean with the deposit number of CCTCC No: M2014086. Fungal fermentation culture to obtain the fermented product containing isocoumarin derivatives, then adding methanol to soak in ultrasonic filtration, evaporated to dryness, and then extracted with ethyl acetate and evaporated to dryness to obtain crude extract, the extract is subjected to reduced pressure silica gel column layer separation, reversed-phase medium pressure column chromatography, and finally reversed-phase semi-preparative high-performance liquid chromatography separation and purification. The onset of Zheimer's disease and help relieve its symptoms.
Description
Technical Field
The invention relates to an isocoumarin derivative, in particular to an isocoumarin derivative and a preparation method and application thereof.
Background
The isocoumarin derivatives have anticancer, antibacterial, protease inhibiting and antioxidant effects. The inventor carries out an antioxidation experiment on an ethyl acetate extract obtained by solid fermentation of sponge epiphyte Aspergillus ustus (preserved in China center for type culture Collection, with the preservation number of CCTCC No: M2014086), finds that the sponge epiphyte Aspergillus ustus has antioxidation activity, and researches the active ingredients of the sponge epiphyte Aspergillus ustus to separate out a novel isocoumarin derivative. At present, the chemical structure and the antioxidant activity of the compound are not reported, so that the related medicines are not seen in the market.
Disclosure of Invention
The invention aims to solve the technical problem of providing an isocoumarin derivative with antioxidant activity and a preparation method and application thereof.
The technical scheme adopted by the invention for solving the technical problems is as follows: an isocoumarin derivative, the structural formula of which is shown as I:
the preparation method of the isocoumarin derivative specifically comprises the following steps:
(1) fermentation production: marking off Aspergillus niger (Aspergillus ustus) with the preservation number of CCTCC No. M2014086 for rejuvenation, selecting a single colony, inoculating into a PDB liquid culture medium, and culturing at 28 ℃ and 150rpm for 5 days to obtain a seed solution; inoculating the seed liquid into a rice culture medium according to the volume ratio of 5-20%, standing and fermenting at 28 deg.C for 30 days;
(2) obtaining a crude extract: adding methanol into the conical flask after fermentation, immersing the solid, performing ultrasonic treatment for 15 minutes, standing overnight, and filtering the methanol extract with gauze to remove solid residues; leaching the solid residue for 3-5 times, mixing the methanol extractive solutions, evaporating to remove methanol, dissolving with water, adding ethyl acetate with the same volume as the water solution, extracting for 5 times, mixing extractive solutions, and concentrating under reduced pressure to remove ethyl acetate to obtain crude extract;
(3) separation and purification of compounds: dissolving the crude extract by using a mixed solvent of dichloromethane and methanol, adding 200-mesh 300-mesh silica gel for sample mixing, performing reduced pressure silica gel column chromatography on the crude extract by using petroleum ether/ethyl acetate with a volume ratio of 2:1 as an eluent, and collecting an elution component; performing gel column chromatography (LH-20) on the eluted component by using a mixed solvent of dichloromethane and methanol as an eluent, and collecting the eluted component; separating the eluted components by reverse phase medium pressure column chromatography, adopting methanol and water as eluent, linearly eluting the components from 30% methanol in volume fraction to 100% methanol in gradient, eluting for 120 minutes at a flow rate of 20mL/min, collecting the fraction with peak time of 80-90 minutes, and finally separating and purifying the fraction by semi-preparative reverse phase high performance liquid chromatography to obtain the isocoumarin derivative, wherein the structure of the isocoumarin derivative is shown as formula I:
the PDB liquid culture medium has the following formula: 200g of potatoes, 20g of glucose, 35g of sea crystals and 1L of distilled water; the formula of the rice culture medium is as follows: 100g of rice, 3.5g of sea crystal and 100mL of distilled water.
The volume ratio of the dichloromethane to the methanol in the dichloromethane and methanol mixed solvent is 1: 1.
the eluent of the semi-preparative reverse phase high performance liquid chromatography is prepared by mixing acetonitrile and water according to the volume ratio of 28: 72.
The application of the isocoumarin derivative and the application of the isocoumarin derivative in the aspect of preparing an antioxidant.
Compared with the prior art, the invention has the advantages that: the invention relates to an isocoumarin derivative and a preparation method and application thereof, wherein a fermentation product containing a chlorine aromatic compound is obtained through microbial fermentation culture, then the fermentation product is soaked by methanol and extracted by ethyl acetate to obtain a crude extract, and the crude extract is separated and purified by reduced pressure silica gel column chromatography, medium pressure column chromatography and reversed phase semi-preparative high performance liquid chromatography; the isocoumarin derivative is obtained by microbial fermentation, and the method has the characteristics of simple operation process, short production period, low product cost and no pollution to the environment.
The Aspergillus oryzae (Aspergillus oryzae) is DJ003 strain with preservation number of CCTCC No. M2014086, and is preserved in China center for type culture Collection in 2014 at 03 and 14 days, with preservation address of Wuhan university in Wuhan.
Drawings
FIG. 1 shows that compound I scavenges DPPH radicals in a concentration-dependent manner. Compound i or vitamin c (vitc) was added to a 0.2mM DPPH solution at the indicated concentrations for 20 minutes, and the DPPH free radical content was measured by evaluating the absorbance at 517nm, the data representing the mean ± SEM of three separate experiments; p <0.01 relative to control (ANOVA and Duncet test).
Detailed Description
The invention is described in further detail below with reference to the accompanying examples.
Example 1
The structural formula of the isocoumarin derivative is shown as the following formula I:
example 2
The preparation method of the isocoumarin derivative shown as the formula I comprises the following steps:
(1) fermentation production: marking off Aspergillus niger (Aspergillus ustus) with the preservation number of CCTCC No. M2014086 for rejuvenation, selecting a single colony, inoculating into a PDB liquid culture medium, and culturing at 28 ℃ and 150rpm for 5 days to obtain a seed solution; inoculating the seed liquid into a rice culture medium according to the volume ratio of 5-20%, standing and fermenting at 28 deg.C for 30 days; the formula of the PDB liquid culture medium is as follows: 200g of potatoes, 20g of glucose, 35g of sea crystals and 1L of distilled water; the formula of the rice culture medium is as follows: 100g of rice, 3.5g of sea crystal and 100mL of distilled water;
(2) obtaining a crude extract: adding methanol into the conical flask after fermentation, immersing the solid, performing ultrasonic treatment for 15 minutes, standing overnight, and filtering the methanol extract with gauze to remove solid residues; leaching the solid residue for 3-5 times, mixing the methanol extractive solutions, evaporating to remove methanol, dissolving with water, adding ethyl acetate with the same volume as the water solution, extracting for 5 times, mixing extractive solutions, and concentrating under reduced pressure to remove ethyl acetate to obtain crude extract;
(3) separation and purification of compounds: dissolving the crude extract by using a mixed solvent of dichloromethane and methanol, adding 200-mesh 300-mesh silica gel for sample mixing, performing reduced pressure silica gel column chromatography on the crude extract by using petroleum ether/ethyl acetate with a volume ratio of 2:1 as an eluent, and collecting an elution component; performing gel column chromatography (LH-20) on the eluted component by using a mixed solvent of dichloromethane and methanol as an eluent, and collecting the eluted component; separating the eluted components by reverse phase medium pressure column chromatography, adopting methanol and water as eluent, linearly eluting the components from 30% methanol in volume fraction to 100% methanol in gradient, eluting for 120 minutes at a flow rate of 20mL/min, collecting the fraction with peak time of 80-90 minutes, and finally separating and purifying the fraction by semi-preparative reverse phase high performance liquid chromatography to obtain the isocoumarin derivative, wherein the structure of the isocoumarin derivative is shown as formula I:
wherein the volume ratio of dichloromethane to methanol in the mixed solvent of dichloromethane and methanol is 1: 1; the eluent of the semi-preparative reverse phase high performance liquid chromatography is prepared by mixing acetonitrile and water according to the volume ratio of 28: 72.
The compound I is purple red powder with a molecular formula C14H18O5，
(c 0.2,CHCl3) Cation HRESIMS m/z: 284.1490[ M + NH4]+，1H and13the C-NMR data are shown in Table 1.
TABLE 1 preparation of compound I1H and13c NMR data (600 and 150MHz, in DMSO-d)6)a
Note: the signal attribution of the table is based on DEPT,1H-1H COSY, HSQC and HMBC map analysis results. The hydrogen signals are used for multiple degrees respectivelys (singlet), d (doublet), t (triplet) and m (multiplet) tables.
Example 3
In vitro antioxidant Activity test (free radical scavenging Activity test)
(1) Experimental sample
Preparing a solution of a sample to be detected: the test sample is the pure compound I separated and purified in the above example 2, and an appropriate amount of sample is precisely weighed for measuring the activity.
(2) Experimental methods
The antioxidant properties of compound i were determined by DPPH free radical scavenging assay. The drug was added at various concentrations to a solution of DPPH in methanol (0.2 mM). The mixture (200. mu.L/well) was added to a 96-well plate and shaken at room temperature for 20 minutes. The absorbance was measured at 517nm with a microplate reader. Vitamin C was used as a positive control. DPPH radical scavenging activity was calculated using the formula: DPPH radical scavenging activity (%) (absorbance of control-absorbance of sample)/absorbance of control ] × 100.
(3) Results of the experiment
In the free radical scavenging assay of compound i. Compound I or vitamin C (VitC) was added to a 0.2mM DPPH solution at the indicated concentration for 20 minutes, and the DPPH radical content was measured by evaluating the absorbance at 517 nm. As shown in figure 1, compound i concentration-dependently decreased DPPH free radical content, indicating that compound i may act as an effective antioxidant, and the data represent the mean ± SEM of three separate experiments, p <0.01 relative to control (ANOVA and Duncet test). The potent antioxidant effect of compound i may be due to its hydroxyl group. Many antioxidants, such as vitamin C and vitamin E, may help delay the onset of Alzheimer's Disease (AD) and help alleviate its symptoms. Therefore, the compound I can be used as an isocoumarin derivative with strong free radical scavenging performance and can also be used for treating AD.
The above description is not intended to limit the present invention, and the present invention is not limited to the above examples. Those skilled in the art should also realize that such changes, modifications, additions and substitutions are within the true spirit of the invention.
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| CN111592989B (en) * | 2020-06-28 | 2021-09-17 | 曲靖师范学院 | Aspergillus sp.G12 and method for preparing isocorydine alkali by fermenting Aspergillus sp.G12 |
| CN113061631B (en) * | 2021-03-31 | 2022-09-16 | 华中科技大学 | Isochroman derivative and enzymatic synthesis method and application thereof |
| CN118165005A (en) * | 2021-11-26 | 2024-06-11 | 北京中医药大学东直门医院 | Application of dihydrothiophene hybrid isocoumarin compound with circular polarized fluorescence in preparation of anti-counterfeiting material or cell imaging material |
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