CN114832010A - Application of flavonol glycoside derivatives in preparation of antitumor drugs - Google Patents
Application of flavonol glycoside derivatives in preparation of antitumor drugs Download PDFInfo
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- CN114832010A CN114832010A CN202210594022.XA CN202210594022A CN114832010A CN 114832010 A CN114832010 A CN 114832010A CN 202210594022 A CN202210594022 A CN 202210594022A CN 114832010 A CN114832010 A CN 114832010A
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- XUDNWQSXPROHLK-OACYRQNASA-N 2-phenyl-3-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one Chemical class O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=CC=CC=2)OC2=CC=CC=C2C1=O XUDNWQSXPROHLK-OACYRQNASA-N 0.000 title claims abstract description 20
- 239000002246 antineoplastic agent Substances 0.000 title claims abstract description 15
- 229940041181 antineoplastic drug Drugs 0.000 title claims abstract description 14
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- 206010028980 Neoplasm Diseases 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 7
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- 206010017758 gastric cancer Diseases 0.000 claims description 7
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- 239000004480 active ingredient Substances 0.000 claims description 6
- 208000029742 colonic neoplasm Diseases 0.000 claims description 6
- 206010003445 Ascites Diseases 0.000 claims description 5
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
- 208000009956 adenocarcinoma Diseases 0.000 claims description 5
- 201000005202 lung cancer Diseases 0.000 claims description 5
- 208000020816 lung neoplasm Diseases 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 210000004185 liver Anatomy 0.000 claims description 3
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- 239000000080 wetting agent Substances 0.000 claims description 2
- 230000000274 adsorptive effect Effects 0.000 claims 1
- 230000002440 hepatic effect Effects 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 abstract description 11
- 239000003814 drug Substances 0.000 abstract description 7
- 229940079593 drug Drugs 0.000 abstract description 4
- 210000004027 cell Anatomy 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000001228 spectrum Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- 239000004922 lacquer Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000004007 reversed phase HPLC Methods 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 238000000605 extraction Methods 0.000 description 3
- 208000002154 non-small cell lung carcinoma Diseases 0.000 description 3
- 230000035755 proliferation Effects 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 3
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 238000005034 decoration Methods 0.000 description 2
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- VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 2
- 229960005420 etoposide Drugs 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- HVQAJTFOCKOKIN-UHFFFAOYSA-N flavonol Natural products O1C2=CC=CC=C2C(=O)C(O)=C1C1=CC=CC=C1 HVQAJTFOCKOKIN-UHFFFAOYSA-N 0.000 description 2
- -1 flavonol glycosides Chemical class 0.000 description 2
- 235000011957 flavonols Nutrition 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000010829 isocratic elution Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
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- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 244000000007 bacterial human pathogen Species 0.000 description 1
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- 210000004369 blood Anatomy 0.000 description 1
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- 230000005182 global health Effects 0.000 description 1
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 1
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
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- 230000005764 inhibitory process Effects 0.000 description 1
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- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
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- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
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- 238000007254 oxidation reaction Methods 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention belongs to the technical field of medicine preparation, and discloses an application of flavonol glycoside derivatives in preparing antitumor medicines. The flavonol glycoside derivative provided by the invention has good anti-tumor effect, can be used for preparing anti-tumor drugs, is used as an active component of the anti-tumor drugs, and has good practical application.
Description
Technical Field
The invention relates to the field of medicines, and relates to an application of flavonol glycoside derivatives in preparation of antitumor drugs.
Background
Tumors are usually classified into the categories of "mass" and "accumulation" and their pathogenesis is that qi, blood and body fluids are not smoothly transported and transformed, and then the stagnation is caused by stasis and phlegm. Recent modern pharmacological research considers tumors as a global health, economy and social multiple problem. Big data shows that the number of new cancers worldwide reaches ten million, wherein the number of death is nearly half, which becomes the second cause of death of cardiovascular diseases, the death causes are ranked in the first three, and the difference is seen between men and women, wherein men are lung cancer, gastric cancer and liver cancer in turn, and women are lung cancer, breast cancer and colorectal cancer in turn.
The flavonol glycosides are flavonoid components with special structures. The components are derivatives of C3-position hydroxyl of flavonoid which are glycoside-formed, most of the components have hydroxyl or methoxyl and are generally called flavonol glycosides. The components are widely distributed and reported in most higher plants. The flavonol glycoside derivative as biological preparation has great potential in resisting tumor, resisting oxidation, etc. In addition, the product also has biological activity such as anti-inflammatory activity.
Disclosure of Invention
In view of the above, the present invention provides an application of flavonol glycoside derivatives in the preparation of antitumor drugs, and particularly provides an application of flavonol glycoside derivatives or pharmaceutically acceptable salts thereof in the preparation of antitumor drugs, wherein the flavonol glycoside derivatives have good proliferation inhibition effect on tumor cell lines and good antitumor activity.
The invention provides the following technical scheme:
the flavonol glycoside derivative with the structure shown in the formula I or the salt which can be formed by the flavonol glycoside derivative in pharmacy is applied to preparing the antitumor drugs,
further, the tumor is one or more of lung cancer, breast cancer, liver ascites adenocarcinoma, stomach cancer and colon cancer.
Furthermore, the anti-tumor drug is a drug for inhibiting the proliferation of tumor cell lines.
Further, the tumor cell line is one or more of a human non-small cell lung cancer cell line (A549), a human breast cancer cell line (MDA-MB-231), a human liver ascites adenocarcinoma cell line (SK-Hep-1), a human gastric cancer cell line (SNU638) and a colon cancer cell line (HCT 116).
The invention also provides a preparation method of the flavonol glycoside derivative shown in the formula I, which comprises the following steps:
1) extraction of
Collecting lacquer (30kg), drying in the shade, pulverizing, extracting with anhydrous ethanol at room temperature (5L x 3), and concentrating the extractive solution under reduced pressure to dry to obtain about 2kg of converted substance residue (i.e. lacquer extract).
2) Purification by reverse phase silica gel chromatography
Dissolving the obtained residue in appropriate amount of methanol, adding into chromatographic column filled with 500g of reverse phase silica gel (120 angstrom, 30-50 mesh), gradient eluting with methanol-water system (30% -100% methanol), collecting eluate, and collecting eluate eluted with 20% ethanol solution.
3) Purification by reversed phase high performance liquid chromatography
Separating and purifying the flow obtained in the step 2) by using a reversed phase high performance liquid chromatography. The separation conditions were: chromatographic column Hedera C 18 A-5 μm, 4.6mm I.D. times 250mm (Hanbang technology, Jiangsu), and the elution system is methanol-water isocratic elution, and the specific conditions are as follows: methanol-water (30:70, V/V) flow rate 2.0 mL/min. The detection wavelength is 254nm, the column temperature is 25 ℃, and the sample injection amount is 20 mu L. Obtaining the flavonol glycoside derivative with the structure shown in the formula I.
The invention also provides an anti-tumor medicament, which comprises an active ingredient and a pharmaceutically acceptable carrier, wherein the active ingredient is a flavonol glycoside derivative with a structure shown in a formula I or a pharmaceutically acceptable salt thereof,
further, the pharmaceutically acceptable carrier is selected from one or more of diluents, excipients, fillers, binders, wetting agents, disintegrants, absorption enhancers, surfactants, adsorption carriers, and lubricants.
Compared with the prior art, the invention provides the application of the novel flavonol glycoside derivatives in preparing the antitumor drugs, and in vitro tests prove that the flavonol glycoside derivatives provided by the invention have better antitumor activity, and particularly have good proliferation inhibiting effect on human non-small cell lung cancer cell lines (A549), human breast cancer cells (MDA-MB-231), human ascites hepatoma cells (SK-Hep-1), human gastric cancer cell lines (SNU638) and colon cancer cells (HCT116), have better antitumor activity, can be used as active ingredients of the antitumor drugs, and have wide application.
Drawings
FIG. 1 is an HPLC liquid chromatogram of a flavonol glycoside derivative prepared in example 1 of the present invention
FIG. 2 is a graph showing hydrogen spectrum data of the compound obtained in example 1 of the present invention;
FIG. 3 is a graph showing carbon spectrum data of the compound obtained in example 1 of the present invention;
FIG. 4 is a cell morphology of the antitumor activity of the compound obtained in example 1 of the present invention.
Detailed Description
In order to further illustrate the present invention, the flavonol glycoside derivatives and the preparation method thereof provided by the present invention are described in detail below with reference to examples.
Example 1 preparation of a Compound of formula I
The compound is prepared by the steps of extraction, purification and the like under the conventional condition under the laboratory culture condition. Wherein the plant is Toxicodendra vernicifluum (Stokes) F.A.Barkl.
The process of the specific compound is as follows:
1) extraction of
Collecting lacquer (30kg), drying in the shade, pulverizing, extracting with anhydrous ethanol at room temperature (5L x 3), and concentrating the extractive solution under reduced pressure to dry to obtain about 2kg of converted substance residue (i.e. lacquer extract).
2) Purification by reverse phase silica gel chromatography
Dissolving the obtained residue in appropriate amount of methanol, adding into chromatographic column filled with 500g of reverse phase silica gel (120 angstrom, 30-50 mesh), gradient eluting with methanol-water system (30% -100% methanol), collecting eluate, and collecting eluate eluted with 20% ethanol solution.
3) Purification by reversed phase high performance liquid chromatography
Separating and purifying the flow obtained in the step 2) by using a reversed phase high performance liquid chromatography. The separation conditions were: chromatographic column Hedera C 18 A-5 μm, 4.6mm I.D. times 250mm (Hanbang technology, Jiangsu), and the elution system is methanol-water isocratic elution, and the specific conditions are as follows: methanol-water (30:70, V/V), flow rate 2.0 mL/min. The detection wavelength is 254nm,the column temperature was 25 ℃ and the amount of sample was 20. mu.L. Obtaining the compound with the structural formula I, wherein the high performance liquid phase separation chromatogram, high resolution mass spectrum (HRESIMS) data, hydrogen spectrum data diagram, carbon spectrum data diagram, two-dimensional nuclear magnetic resonance data diagram (HSQC) and two-dimensional nuclear magnetic resonance data diagram (HMBC) are shown in figures 1-4.
Compound I, 4 ', 7-dihydroxy-3' -methoxy-3-O- β -D-glucopyranosyl-flavanoid, yellow amorphous powder.
The nmr hydrogen spectra, carbon spectra and HMBC correlation data for compound 1 are shown in table 1;
high resolution ESI mass spectral data for compound 1: (HRESIMS) M/z463.1231[ M + H ]] + (calc.for C 22 H 22 O 11 463.1235).
TABLE 1 Hydrogen and carbon spectra data for Compound 1 (deuterated methanol)
The above results indicate that the obtained compound has the correct structure.
Example 2: antitumor Activity of Compound I of the present invention
(1) Experimental Material
Instruments and reagents: a microbial incubator; microplate reader (Bio-TEK ELx 800); LB medium (Shanghai bioengineering Co., Ltd.). The tumor cell lines used were tested: a549 (human non-small cell lung cancer cell line), MDA-MB-231 (human breast cancer cell), SK-Hep-1 (human hepatoascites adenocarcinoma cell), SNU638 (human gastric cancer cell line), HCT116 (colon cancer cell), purchased from the institute of cell research of Chinese academy of medicine sciences.
Test samples: the purity of the active compound I of the lacquer is more than 95 percent; meanwhile, etoposide is selected as a positive control drug, and each compound is dissolved in DMSO and then diluted.
(2) Experimental methods
Preparing LB culture solution, sterilizing at 121 ℃ for 25 minutes for later use, adding the prepared diluted bacterial solution into a 96-well plate, adding 180 mu l of the diluted bacterial solution into each well, preparing the compound 1 into DMSO solution with a certain concentration, diluting the DMSO solution into micropores containing the tumor strain solution step by step according to a multiple relation to ensure that the final concentration of the DMSO solution is 0.04,0.2,1,5 and 25 mu M in sequence, culturing the DMSO solution in an incubator at 37 ℃ for 24 hours, reading absorbance at 340nm by using an enzyme-labeling instrument, wherein etoposide is used as a positive control. The experiment was repeated 3 times. The morphology of the cells with antitumor activity is shown in FIG. 4. Calculating the semi-Inhibitory Concentration (IC) of each test sample to human pathogenic bacteria 50 Value).
(3) Results of the experiment
The results of the experiment are shown in table 2.
TABLE 2 antitumor Activity data for Compound 1
The result shows that the compound I has good antitumor activity and can be used as an active ingredient of antitumor drugs.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (4)
1. An application of flavonol glycoside derivatives with a structure shown in formula I or pharmaceutically-formed salts thereof in preparing antitumor drugs.
2. The use of claim 1, wherein the tumor is one or more of lung cancer, breast cancer, hepatic ascites adenocarcinoma, stomach cancer and colon cancer.
3. An antitumor drug is characterized by comprising an active ingredient and a pharmaceutically acceptable carrier, wherein the active ingredient is a flavonol glycoside derivative with a structure shown in formula I or a pharmaceutically acceptable salt thereof;
the tumor is one or more of lung cancer, breast cancer, liver ascites adenocarcinoma, gastric cancer and colon cancer.
4. The antitumor agent as claimed in claim 3, wherein said pharmaceutically acceptable carrier is selected from one or more of diluents, excipients, fillers, binders, wetting agents, disintegrants, absorption enhancers, surfactants, adsorptive carriers and lubricants.
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| CN202210594022.XA CN114832010A (en) | 2022-05-27 | 2022-05-27 | Application of flavonol glycoside derivatives in preparation of antitumor drugs |
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| CN202210594022.XA CN114832010A (en) | 2022-05-27 | 2022-05-27 | Application of flavonol glycoside derivatives in preparation of antitumor drugs |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060105967A1 (en) * | 2004-11-18 | 2006-05-18 | Advanced Gene Technology, Corp. | Flavone derivatives as TNFalpha inhibitors or antagonists |
| US20180353462A1 (en) * | 2015-05-02 | 2018-12-13 | Henry Lowe | Therapeutic agents containing cannabis flavonoid derivatives targeting kinases, sirtuins and oncogenic agents for the treatment of cancers |
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2022
- 2022-05-27 CN CN202210594022.XA patent/CN114832010A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060105967A1 (en) * | 2004-11-18 | 2006-05-18 | Advanced Gene Technology, Corp. | Flavone derivatives as TNFalpha inhibitors or antagonists |
| US20180353462A1 (en) * | 2015-05-02 | 2018-12-13 | Henry Lowe | Therapeutic agents containing cannabis flavonoid derivatives targeting kinases, sirtuins and oncogenic agents for the treatment of cancers |
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