CN111166740A - Application of 3-O-methyl quercetin in antioxidation or blood sugar reduction - Google Patents

Application of 3-O-methyl quercetin in antioxidation or blood sugar reduction Download PDF

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CN111166740A
CN111166740A CN202010202063.0A CN202010202063A CN111166740A CN 111166740 A CN111166740 A CN 111166740A CN 202010202063 A CN202010202063 A CN 202010202063A CN 111166740 A CN111166740 A CN 111166740A
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quercetin
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methyl quercetin
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张强
焦中高
刘杰超
张春岭
刘慧�
吕真真
杨文博
陈大磊
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Zhengzhou Fruit Research Institute CAAS
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Abstract

the invention discloses application of 3-O-methyl quercetin in oxidation resistance or blood sugar reduction, belongs to the technical field of medicines, and aims to provide a quercetin derivative with oxidation resistance and blood sugar reduction activity, namely 3-O-methyl quercetin, and application of the quercetin derivative, namely 3-O-methyl quercetin serving as α -glucosidase inhibitor and an antioxidant in preparation of medicines and/or health care products for treating diabetes.

Description

Application of 3-O-methyl quercetin in antioxidation or blood sugar reduction
Technical Field
The invention belongs to the technical field of medicines, and particularly relates to application of 3-O-methyl quercetin in oxidation resistance or blood sugar reduction.
Background
Quercetin derivatives are widely present in fruits, vegetables, tea leaves, medicinal materials and other plants, and are phenolic substances widely present in daily diet. Research shows that quercetin has the functions of resisting inflammation, resisting bacteria, resisting cancer, lowering blood sugar, resisting virus, etc. and has powerful antioxidant function. In recent years, compounds having better activity than quercetin can be obtained by screening for activity of derivatives obtained by modifying the structure of quercetin as a lead compound. Mulholland et al synthesized a water-soluble quercetin prodrug, 3' -O-N-carboxymethylcarboxamide quercetin, and has entered clinical stage I, and has been found to inhibit the growth of ovarian cancer A2780 cells, primarily blocking proliferation of cells in the late S phase and early G2 phase (Mulholland P J, Ferry D R, Anderson D, oral Pre-clinical and clinical study of QC12, a water-soluble, pro-drug of research in anal of Oncology,2001,12(2): 245-248.). Ye et al performed anti-tumor experiments with quercetin phenyl isocyanate (PHICNQ), found that PHICNQ has 73 times and 308 times of the proliferation inhibition effect on K562 cells and CT26 cells, respectively, and significantly improved the anti-Cancer activity of quercetin derivatives (YE B, YANG J L, CHEN LJ, et al, indication of apoptosis by phthalic acid and availability of quercetin: innovative of fat shock protein. anti-Cancer Drug,2007,18(10): 1165-1171.). Quercetin reacts with n-butyl isocyanate to obtain 3,3 ', 4', 7-O-tetraacylated derivatives, which have higher cell proliferation inhibiting activity on MCF-7 than that of quercetin (Honng T K D, Huynh T K C, Nguyen T D. Synthesis, chromatography, anti-inflammatory and anti-proliferative activity inhibiting MCF-7cells of O-alkyl and O-acyl ketone derivatives. biological Chemistry 2015, 63.). Therefore, the study of the novel activity of quercetin derivatives is a huge raw material resource.
the research shows that α -glucosidase inhibitor can inhibit the activity of α -glucosidase on the brush border of villus mucous membrane cells of small intestine, delay the digestion and absorption of carbohydrates such as starch, cane sugar and the like, and achieve the effect of controlling postprandial hyperglycemia.
Disclosure of Invention
aiming at the problems in the prior art, the invention aims to provide a quercetin derivative, namely 3-O-methyl quercetin with antioxidant and hypoglycemic activities, and application thereof as an α -glucosidase inhibitor and an antioxidant in preparation of medicines and/or health care products for treating diabetes.
The invention aims to provide application of 3-O-methyl quercetin in resisting oxidation or reducing blood sugar, in particular application of 3-O-methyl quercetin in preparing medicines and/or health-care products with the functions of resisting oxidation or reducing blood sugar.
The invention also aims to provide a medicine and/or health-care product with the functions of resisting oxidation or reducing blood sugar, wherein the effective component of the medicine and/or health-care product contains 3-O-methyl quercetin.
the invention also aims to provide application of 3-O-methyl quercetin serving as α -glucosidase inhibitor and an antioxidant in preparation of a medicine and/or health-care product for treating diabetes.
The medicine or health care product of the invention is mixed with carriers, solvents, diluents, excipients and other media which are acceptable in pharmacy or food, and can be prepared into powder, granules, capsules, injections, oral liquid or tablets according to different requirements.
The technical scheme of the invention has the advantages
the 3-O-methyl quercetin of the invention has good α -glucosidase inhibition activity and simultaneously has antioxidation activity, and the inhibition test of the α -glucosidase in vitro proves that the 3-O-methyl quercetin of the invention has obvious inhibition activity on the α -glucosidase and IC (integrated circuit) for inhibiting the α -glucosidase50The value was 1.38. + -. 0.01. mu.g/mL.
In vitro and in vivo antioxidant experiments prove that the 3-O-methyl quercetin has remarkable activities on Oxygen Radical Absorption Capacity (ORAC) and Cell Antioxidant Activity (CAA), and the results are that ORAC value is 4.71 +/-0.12 mu mol TE/mu mol and EC5019.53 + -1.48 mu mol/mL, and has antioxidant effect similar to that of quercetin.
the experimental results show that the 3-O-methyl quercetin provided by the invention has the potential of treating diabetes and other related diseases taking α -glucosidase and oxidative stress as targets.
Drawings
FIG. 1 is a Lineweaver-Burk curve for 3-O-methyl quercetin inhibiting α -glucosidase;
FIG. 2 is an ORAC fluorescence intensity-time kinetic curve of 3-O-methyl quercetin;
FIG. 3 is a graph of the effect of 3-O-methyl quercetin on the fluorescence intensity-time kinetics of HepG2 cells.
Detailed Description
Terms used in the present invention have generally meanings as commonly understood by one of ordinary skill in the art, unless otherwise specified.
The present invention will be described in further detail with reference to the following data in conjunction with specific examples. The following examples are intended to illustrate the invention and are not intended to limit the scope of the invention in any way.
3-O-Methyl Quercetin (3-O-Methyl Quercetin) is one of Quercetin derivatives, and has molecular formula of C16H12O7(ii) a Molecular weight: 316.26, respectively; CAS accession number: 1486-70-0, structural formula:
Figure BDA0002419725380000031
example 1
3-O-methyl Quercetin in vitro inhibition α -glucosidase Activity test
1.1 reagents α -glucosidase (α -glucosidase, Sigma,750U), 4-nitrophenyl- α -D-glucopyranoside (pNPG, TOKYO Chemica Industry Co., LTD), Acarbose (Acarbose, TOKYO Chemica Industry Co., LTD), corosolic acid, Na2HPO4，NaH2PO4。
Comparative product 1
Rhamnetin (Rhamnetin) is a quercetin derivative, and has molecular formula of C16H12O7(ii) a Molecular weight: 316.26, respectively; CAS accession number: 90-19-7, the structural formula is:
Figure BDA0002419725380000032
comparative product 2
Quercetin (Quercetin 3-rhamnoside) is a kind of Quercetin derivatives, and has molecular formula C21H20O11(ii) a Molecular weight: 448.38, respectively; CAS accession number: 522-12-3, the structural formula is:
Figure BDA0002419725380000033
an experimental instrument: the microplate reader TECAN infinite M200 PRO (Teacan Group ltd., Swizerland).
1.2 Experimental procedures
1.2.1 preparation of drug solution: preparing 3-O-methyl quercetin, acarbose and corosolic acid into 10mg/mL mother liquor with dimethyl sulfoxide (DMSO), and adding ultrapure water and Na2HPO4And NaH2PO467mmol/mL phosphate buffer (PBS, pH 6.8), 5mmol/mL pNPG solution using PBS, and 0.2mol/mL Na solution using PBS2CO3the solution was prepared with PBS to obtain 0.8U/mL of α -glucosidase.
1.2.2 protocol now samples are diluted with PBS to different concentration gradients (DMSO amount less than 5%), 120. mu.L of sample solution is added per well to give final concentrations of 100. mu.g/mL respectively, 20. mu.L of α -glucosidase (0.8U/mL) is added, reaction is carried out at 37 ℃ for 15min, then 20. mu.L of 5mmol/mL substrate p-nitrophenyl- α -D-glucopyranoside (pNPG) is added, after leaving to react at 37 ℃ for 15min, 80. mu.L of 0.2mol/mL Na is added per well2CO3The reaction was stopped by the solution and measured by a microplate reader at a wavelength of 405 nm.
The positive control group was acarbose and corosolic acid (8. mu.L of corosolic acid or acarbose + 112. mu. LPBS + 20. mu.L of enzyme + 20. mu. LpNPG);
negative control group (8. mu.L of LDMSO + 112. mu.L of PBS + 20. mu.L of enzyme + 20. mu.L of pNPG),
blank (8. mu.L DMSO + 112. mu.LPBS).
1.3 calculation formula: inhibition rate [1- (OD)Sample (I)–ODSample blank)/(ODNegative control-ODBlank space)]×100％
Where the half inhibitory concentration IC of the compound tested50SPSS 20.0 statistics were used.
1.4 results of the experiment
TABLE 1 IC of the compound 3-O-methyl Quercetin on α -glucosidase inhibitory Activity50Value of
Figure BDA0002419725380000041
from the results in Table 1, it is clear that IC of 3-O-methyl quercetin for α -glucosidase501.38 + -0.01 μ g/mL, positive control IC of acarbose and corosolic acid for α -glucosidase50324.85 +/-8.56 and 12.6 +/-0.12 mu g/mL respectively, and the IC of rhamnosine to α -glucosidase50>IC of 200. mu.g/mL rhamnosin α -glucosidase50the alpha-glucosidase inhibition activity of the 3-O-methyl quercetin is 32.14 +/-2.63 mu g/mL, which shows that the alpha-glucosidase inhibition activity of the 3-O-methyl quercetin is obviously stronger than that of positive control acarbose and corosolic acid and is also obviously better than that of quercetin derivatives of rhamnoside and quercetin, the alpha-glucosidase inhibition activity of the 3-O-methyl quercetin is 1.63 times that of the quercetin, and the alpha-glucosidase inhibition effect of the 3-O-methyl quercetin is good.
1.5 inhibition kinetics experiment of Compound 3-O-methyl Quercetin on alpha-glucosidase
1.5.1 Experimental procedures
under the same experimental conditions, the concentration (0.25U/mL) of alpha-glucosidase is changed, the concentration (0.5, 2 mu g/mL) of the inhibitor 3-O-methyl quercetin is changed, the change trend of the absorbance change rate of each reaction system along with the increase of the substrate concentration (0.5, 1, 2, 4 mu g/mL) is respectively measured, a Lineweaver-Burk curve is drawn, the type of the inhibition effect on α -glucosidase is determined, and the inhibition constant Ki of each inhibitor on α -glucosidase is respectively calculated.
1.5.2 results of the experiment
As can be seen from FIG. 1, under the same experimental conditions, 1/v and 1/pNPG are linear, the slope of the equation gradually increases with the increase of the concentration of 3-O-methyl quercetin, and the inhibition effect of 3-O-methyl quercetin on α -glucosidase is a typical competitive inhibition compared with the Y axis, which has an inhibition constant Ki of (4.73. + -. 0.12). times.10) times.10 on α -glucosidase-7(n＝3)。
Example 2
3-O-methyl Quercetin in vitro antioxidant ability test
2.1ORAC Oxidation resistance test
2.1.1 reagents: vitamin E (Trolox), ABAP [2,2-Azobis (2-amidinopropane) dihydrochloride solution]DCFH-DA (2 ', 7' -Dichlorfluorescin diacetate), Sodium Fluorescein (Sodium Fluorescein), Na2HPO4，NaH2PO4. An experimental instrument: the microplate reader TECAN infinite M200 PRO (Teacan Group ltd., Swizerland).
2.2 Experimental procedures
2.2.1 preparation of drug solution: preparing a sample to be detected into 10mg/mL mother solution by using dimethyl sulfoxide (DMSO); accurately weighing 20mg of fluorescein sodium FL, dissolving in 50mL of PBS (pH 7.4) to obtain FLA solution with concentration of 0.4mg/mL, and storing in refrigerator at-20 deg.C; dissolving 200 mu L of FLA solution in 50mL of PBS solution to prepare FLB solution; dissolving 500 μ L FLB solution in 50mL PBS solution to obtain FL working solution; accurately weighing 2.5mg of Trolox, dissolving in 10mL of PBS solution, and preparing into Trolox mother liquor with the concentration of 1 mmol/L; respectively diluting the Trolox mother liquor into Trolox working solutions with the concentrations of 2.5 mu mol/L, 5 mu mol/L, 10 mu mol/L, 15 mu mol/L, 20 mu mol/L, 25 mu mol/L and 50 mu mol/L by PBS; accurately weighing 322.0mg AAPH dissolved in 10mL PBS solution, and preparing AAPH working solution with the concentration of 119 mmol/L.
2.2.2 operating method: the samples were diluted with DMSO to different concentration gradients so that the final concentrations of the samples in the reaction mixture were 0. mu. mol/L, 10. mu. mol/L, 20. mu. mol/L, and 40. mu. mol/L, respectively. Sucking 50 mu L of samples with different concentration gradients or blank solution (PBS solution) or Trolox standard substance solution (2.5 mu mol/L, 5 mu mol/L, 10 mu mol/L, 15 mu mol/L, 20 mu mol/L, 25 mu mol/L, 50 mu mol/L) into a 96-well plate (special for fluorescence determination), adding 100 mu L of FL working solution into each sample well, and shaking for 3 min; then incubating for 10min in an incubator pre-heated to 37 ℃; and finally, quickly adding 50 mu L of AAPH working solution to start reaction, and quickly placing the reaction product into a microplate reader preheated to 37 ℃ in advance for determination. The enzyme-labeling instrument comprises the following determination conditions: excitation wavelength is 485nm, emission wavelength is 520nm, oscillation is carried out for 10s, and then measurement is carried out once every 2min for 120 min. Each sample is repeated three times in the experiment, and the experiment blank group is a fluorescence attenuation group added with AAPH but not added with antioxidant; the experimental positive control is a fluorescence attenuation group without adding a free radical activator AAPH and an antioxidant.
2.2.3 calculation formula: AUC value 2 × (f)0+f1+f2+…+fn-1+fn)-f0–fn
NetAUC value ═ AUCsample-AUCBlank space
In the formula (f)0Initial fluorescence value when t is 0min, fxThe fluorescence intensity when t is x min;
and (3) taking the concentration of the Trolox solution as an abscissa and NetAUC as an ordinate, and drawing a standard curve:
y＝568.36x–0.7201
and (3) calculating Trolox equivalent according to the standard curve of the concentration of a certain sample, namely obtaining an ORAC value.
2.3 results of the experiment
TABLE 2 ORAC test results for compound 3-O-methyl Quercetin
Figure BDA0002419725380000061
As can be seen from the results in Table 2, the ORAC values of 3-O-methyl quercetin were 4.71. + -. 0.12. mu. mol TE/. mu.mol, and the ORAC values of the control quercetin were 5.52. + -. 0.04. mu. mol TE/. mu.mol, indicating that the oxygen radical absorbance capacity of 3-O-methyl quercetin was similar to that of the control antioxidant quercetin.
Example 3
Intracellular antioxidant (CAA) assay of 3-O-methyl Quercetin
3.1 reagent: DCFH-DA (2 ', 7' -Dichlorfluorescin diacetate), fluorescein sodium (SodiumFluorescein), ABAP [2,2-Azobis (2-amidinopropane) dihydridrochloride solution ], HepG2 hepatoma cells (Kunming institute of Chinese academy of sciences), MEM medium (Gibco), methanol (Tianjin Mao), L-glutamine (Gibco), Hanks Balanced Salt Solution (HBSS), fetal bovine serum (FBS, Gibco), diabody (Gibco), trypsin (Gibco). An experimental instrument: enzyme-linked immunosorbent assay (TECAN _ SNAIN) M200 PRO (Teacan Group Ltd., Swizerland)
3.2 Experimental procedures
3.2.1 principle: the CAA method is to detect active oxygen by utilizing a fluorescent probe DCFH-DA, the DCFH-DA does not have fluorescence per se, can freely pass through a cell membrane and enter a cell, and can be hydrolyzed by esterase in the cell to generate DCFH, and the DCFH can not pass through the cell membrane, so that the probe can be easily loaded into the cell, the active oxygen in the cell can oxidize the DCFH without fluorescence to generate DCF with fluorescence, the level of the active oxygen in the cell can be detected by detecting the fluorescence of the DCF, and when an antioxidant is absorbed in the cell, the generation of the DCF with fluorescence can be inhibited.
3.2.2 preparation of drug solution: preparing a sample to be detected into 10mg/mL mother solution by using dimethyl sulfoxide (DMSO); 9.47mg of DCFH-DA is dissolved in 1mL of methanol solution to prepare 20mM of DCFH-DA mother liquor; 542mg ABAP was dissolved in 10mL deionized water and prepared as 200mM ABAP stock solution.
3.2.3 cell culture: HepG2 cells were cultured in 10% fetal bovine serum, 1% double antibody (100U/mL) MEM medium at 37 ℃ with 5% CO2And incubating in a 95% humidity incubator, and replacing the culture medium every 1-2 days.
3.2.4 operating method: HepG2 cells in logarithmic growth phase were collected and 100. mu.L of medium was added to a 96-well plate to achieve a cell density of 5X 104Per well; after 24h of incubation, the medium was removed and washed once with PBS; adding a DCFH-DA probe culture medium containing a sample to be detected, wherein the final concentration of the DCFH-DA probe is 25 mu M, and continuously incubating for 1 h; after 1h, the medium was removed and 100 μ L of PBS was added to each well and washed 3 times; then 100. mu.L of 600. mu.M ABAP (Hanks solution dilution) was added, and the 96-well plate was placed in a multifunctional microplate reader for detection at a constant temperature of 37 ℃. The enzyme-labeling instrument comprises the following determination conditions: excitation wavelength is 485nm, emission wavelength is 538nm, oscillation is carried out for 5s, and then measurement is carried out once every 5min for 60 min. In the experiment, four times of repetition are carried out on each sample, and the experiment blank group is a fluorescence attenuation group added with the probe DCFH-DA but not added with ABAP and antioxidant; the positive control of the experiment is a fluorescence attenuation group added with a free radical activator ABAP and a probe DCFH-DA, and the inhibition rate of the experimental dosage of the sample on the cell growth is below 10%.
3.2.5 formula: CAA (unit) ═ 1- ([ integral ] SA/[ integral ] CA)
Integral multiple of reaction (SA): integrated area under the sample time-fluorescence value curve;
integral multiple of formula CA: comparing the integrated area under the time-fluorescence value curve;
EC50: according to log (fa/fu)/log (dos)e) Calculating the medium effect principle;
fa：CAA unit；fu：1-CAA unit；
CAA value ═ Quercetin EC50Sample EC50×100
Represents the micromolar equivalent of quercetin per 100 micromolar sample.
3.2.6 results of the experiment
TABLE 3 results of antioxidant Activity of Compound 3-O-methyl Quercetin cells
Compound (I) EC50(μmol/L)of CAA CAA(μmol QE/100μmol)
3-O-methyl Quercetin 19.53±1.48 44.91±1.24
Quercetin 8.77±0.09 102.24±3.56
As is clear from the results in Table 3, 3-O-methyl Quercetin EC5019.53 + -1.48. mu. mol/L, CAA values 44.91 + -1.24. mu. mol QE/100. mu. mol, EC for control quercetin508.77 +/-0.09 mu mol/L and CAA values of 102.24 +/-3.56 mu mol/QE 100 mu mol, which shows that the intracellular antioxidant activity of the 3-O-methyl quercetin is weaker than that of a control antioxidant quercetin, but the intracellular antioxidant activity of the 3-O-methyl quercetin is good.
The above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be apparent to those skilled in the art that various changes may be made and equivalents may be substituted for elements thereof; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions.

Claims (6)

1.3-O-methyl quercetin can be used for resisting oxidation or lowering blood sugar.
2.3-O-methyl quercetin in the preparation of antioxidant drugs and/or health products.
3. An antioxidant drug and/or health product, characterized in that the effective component thereof contains 3-O-methyl quercetin.
4.3-O-methyl quercetin in the preparation of hypoglycemic drugs and/or health products.
5. A hypoglycemic drug and/or health product, characterized in that the effective component thereof contains 3-O-methyl quercetin.
application of 3-O-methyl quercetin as α -glucosidase inhibitor and antioxidant in preparation of medicine and/or health product for treating diabetes.
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Cited By (1)

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CN113440516A (en) * 2021-08-20 2021-09-28 中国农业科学院郑州果树研究所 Composition for inhibiting alpha-glucosidase and application thereof

Citations (1)

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CN106265629A (en) * 2016-08-12 2017-01-04 郑州大学 The application in esophageal carcinoma chemoprophylaxis of the different rhamnol

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CN106265629A (en) * 2016-08-12 2017-01-04 郑州大学 The application in esophageal carcinoma chemoprophylaxis of the different rhamnol

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EDER LANA E SILVA等: "High-Resolution α-Glucosidase Inhibition Profiling Combined with HPLC-HRMS-SPE-NMR for Identification of Antidiabetic Compounds in Eremanthus crotonoides (Asteraceae)", 《MOLECULES》 *
YH LEE等: "Synthesis of (2-amino)ethyl derivatives of quercetin 3-O-methyl ether and their antioxidant and neuroprotective effects", 《BIOORGANIC & MEDICINAL CHEMISTRY》 *

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113440516A (en) * 2021-08-20 2021-09-28 中国农业科学院郑州果树研究所 Composition for inhibiting alpha-glucosidase and application thereof

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Application publication date: 20200519

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