CN109206429A - A kind of isoquinoline alkaloid compound and its preparation method and application - Google Patents
A kind of isoquinoline alkaloid compound and its preparation method and application Download PDFInfo
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- CN109206429A CN109206429A CN201710553004.6A CN201710553004A CN109206429A CN 109206429 A CN109206429 A CN 109206429A CN 201710553004 A CN201710553004 A CN 201710553004A CN 109206429 A CN109206429 A CN 109206429A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
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Abstract
The invention discloses a kind of isoquinoline alkaloid compounds and its preparation method and application.The invention discloses a kind of isoquinoline alkaloid class compounds and its preparation method and application shown in formula (I).The invention also discloses the purposes of thinfruit hypecoum herb.The compounds of this invention is isolated from thin fruit fennel, using the dry herb coarse powder of alcohol extracting thinfruit hypecoum herb, is concentrated under reduced pressure, elutes through silica gel column chromatography after MCI column chromatographic elution, after TLC is detected, be prepared through two-dimensional liquid chromatography again.Pharmacodynamic test proves that the compounds of this invention and thinfruit hypecoum herb have good anti-tumor activity.
Description
Technical field
The invention belongs to new alkaloids technical fields, and in particular to a kind of isoquinoline alkaloid compound and its preparation side
Method and application.
Background technique
Thinfruit hypecoum herb (Hypecoum leptocarpum Hook.f.et Thoms.) is the plant that Papaveraceae erect hypecoum belongs to
Object is one of the positive kind of traditional Tibetan medicine erect hypecoum, has treatment cat fever, pneumonia cough, the high fever of hot infectious disease, liver
Inflammation, cholecystitis, arthralgia, abscess of throat, hot eyes, solution food poisoning and other effects.
The thinfruit hypecoum herb chemical constitution study that document can be found at present, it was recently reported that wherein twenties kinds of alkaloids
Object is closed, it is less to the research of monomer compound pharmacological activity.
Have no that thinfruit hypecoum herb and its alkaloid component have the report of anticancer effect.
Summary of the invention
The present invention disclose a kind of isoquinoline alkaloid compound or its pharmaceutically acceptable salt shown in column (I),
Or its solvate:
Wherein, R1、R2Separately it is selected from hydrogen, hydroxyl, C1~C4Alkoxy；R3Selected from-(CH2)mNH(CH2)nCH3, m,
N is separately selected from 0~3 integer.
Further, R1、R2It is methoxyl group.
Further, 2 m, n 0.
Further, the compound is
A kind of preparation method of the compounds of this invention, comprising the following steps: take the dry herb of thinfruit hypecoum herb, crushed
Sieve, with miscible with water solvent extraction 1~3 time, combined extract, through extracting, passes through big with water dispersion after concentration after water phase concentration
Hole resin or micro-porous resin column chromatography, are eluted, then through silica gel column chromatography, mixed solvent gradient elution is detected through TLC with solvent
Afterwards, prepare column through C18, solution elution to get.
Further, solvent miscible with water is ethyl alcohol.
Further, extraction time is 3 times, and each extraction time is 12h.
Further, the mass ratio of volume used and the dry herb of thinfruit hypecoum herb is 4~20L to Extraction solvent every time:
1kg, preferably 10L:1kg.
Further, extractant is petroleum ether.
Further, the volume ratio of extractant and aqueous solution is 0.5~10:1, preferably 1.5:1.
Further, the macroreticular resin is D101, AB-8 type macroreticular resin, and the micro-porous resin is MCI resin；
Further, solvent used in the macroreticular resin or micro-porous resin column chromatographic elution is followed successively by water and methanol.
Further, silica gel column chromatography solvent for use is methylene chloride-methanol solvent；And gradient are as follows: methylene chloride:
The volume ratio of methanol is 9:1,8:2,7:3,6:4,5:5,4:6,3:7.
The C18 column elution solution is the mixed solution of acetonitrile and phosphate aqueous solution that volume ratio is 15:85.
Preferably, the mass concentration of phosphoric acid is 0.1% in the phosphate aqueous solution.
The purposes of a kind of the compounds of this invention or its pharmaceutically acceptable salt or its solvate, it is characterised in that: use
In prevention and/or treatment tumour.
Further, the tumour is adenocarcinoma of lung and/or gastric cancer.
A kind of pharmaceutical composition for treating tumour, it be with the compounds of this invention or its solvate or its pharmaceutically may be used
The salt of receiving is active constituent, in addition the preparation that pharmaceutically acceptable auxiliary material is prepared.
A kind of purposes of thinfruit hypecoum herb, for preventing and/or treating tumour.
Further, the tumour is adenocarcinoma of lung.
Preparation of the present invention includes injection, powder-injection, tablet, capsule, granule, capsule, pill, dripping pill
Agent, oral administration solution etc..
Present invention demonstrates that thinfruit hypecoum herb medicinal material is inhibited to the proliferation of human lung adenocarcinoma cell (A549), show
The medicinal material has certain anti-tumor activity, can be used for developing anti-tumor drug.What the present invention was extracted from thinfruit hypecoum herb
Compound has significant inhibiting effect to the proliferation of human lung adenocarcinoma cell (A549) and gastric carcinoma cells (MGC-803), shows
The compound has preferable anti-tumor activity.
Obviously, above content according to the present invention is not being departed from according to the ordinary technical knowledge and customary means of this field
Under the premise of the above-mentioned basic fundamental thought of the present invention, the modification, replacement or change of other diversified forms can also be made.
Specific embodiment
The specific embodiment of form by the following examples remakes further specifically above content of the invention
It is bright.But the range that this should not be interpreted as to the above-mentioned theme of the present invention is only limitted to example below.It is all to be based on above content of the present invention
The technology realized all belongs to the scope of the present invention.
Experimental material used in following embodiment can be bought from commercial channel.
Embodiment 1
(1) extraction of compound leptocaramine
The dry herb 1.5Kg of thinfruit hypecoum herb is taken, crushed 40 meshes, respectively with 95% alcohol steep of 15L 3 times, every time
12 hours, merge ethanol extract, discards petroleum ether layer, water layer with 1.5L petroleum ether extraction with 1L water dispersion after reduced pressure
It chromatographs after reduced pressure through MCI column, is eluted respectively with water and methanol, collect meoh eluate, through silica gel column chromatography after concentration, with
Methylene chloride-methanol gradient elution, gradient are methylene chloride: the volume ratio of methanol is 9:1,8:2,7:3,6:4,5:5,4:6,3:
7, collection liquid is detected through TLC, is merged same section, is obtained 6 parts, number consecutively Fr.1, Fr.2, Fr.3, Fr.4,
Part (Fr.4) containing compound leptocaramine is prepared column through C18 by Fr.5, Fr.6, through acetonitrile: water (contains 0.1%
Phosphoric acid)=15:85 elution, sterling compound leptocaramine17mg is prepared.
(2) compound leptocaramine Structural Identification
The compounds of this invention is buff powder, is dissolved in d-DMSO, to determine that its chemical structure has carried out with the following figure it
Spectrum detection: (1) high resolution mass spectrum；(2) the one-dimensional spectrum of nuclear magnetic resonance1H、13C；(3) Two-dimensional NMR Map HSQC and HMBC；(4) purple
External spectrum and infrared spectroscopy.
Structural Identification process: according to one-dimensional nuclear-magnetism1H、13C H NMR spectroscopy, is tentatively judged as alkaloid compound.According to
The molecular ion peak 367.1656 [M+H] that ESI-MS is obtained+Obtaining its molecular formula with nuclear magnetic data is C21H22N2O4.Degree of unsaturation is
10.In infrared spectroscopy, 3431cm-1For secondary amino group absorption peak, 2956,2870,2922,2820cm-1It is absorbed for methylene and methyl
Peak.By further confirming that for two-dimensional nucleus magnetic spectrum data, in especially HMBC spectrum ,-OCH2O- (δ 6.37, s, 1H) and C-7 (δ
144.8) related to C-8 (δ 141.5), OMe (δ 3.84, s, 3H) is related to C-4 ' (δ 149.0), OMe (δ 3.80, s, 3H) and C-
5 ' (δ 147.5) are related, and NMe (δ 2.55, s, 3H) is related to C-8 ' (δ 49.6), H-7 ' (δ 2.92, t, J=7.3Hz, 2H) and C-
5 ' (δ 113.8), C-6 ' (δ 127.6), C-1 ' (δ 131.9) are related to C-4 ' (δ 149.0).These conclusions and infrared spectroscopy are aobvious
The functional group shown is consistent.By further1H、13C NMR, HSQC, HMBC spectrum analysis (table 1), have finally determined the chemical combination
The structural formula of object are as follows:
Compound structure data are as follows: molecular formula C21H22N2O4, molecular weight 366；UV(MeOH)λmax(logε):
208,244,310,378nm；IR(KBr)νmax 3431,2956,2870,2922,2820,1631,1521,1460,1377,
1128,1048,614,582cm–1；positive HRESIMS:m/z 367.1656[M+H]+(calcd for C21H23N2O4[M
+H]+,367.1658)；1H、13The nuclear magnetic datas such as C such as table 1.
The nuclear magnetic data (In d-DMSO) of 1 the compounds of this invention of table
Illustrate beneficial effects of the present invention below by test.
Test the research of 1 thinfruit hypecoum herb medicinal material anti tumor activity in vitro
1. sample pre-treatments
The dry herb 200g of thinfruit hypecoum herb is taken, crushed 40 meshes, uses 95% alcohol steep of 2L 3 times respectively, every time 12
Hour, merge ethanol extract, is concentrated under reduced pressure and is freeze-dried, obtain thinfruit hypecoum herb alcohol extract sample.
2. thinfruit hypecoum herb alcohol extract anti tumor activity in vitro experimental study
(1) experimental cell system
Human lung adenocarcinoma (A549) cell is purchased from Cell Bank of Chinese Academy of Sciences.
(2) experimental drug and reagent
Experimental drug: the above-mentioned thinfruit hypecoum herb alcohol extract obtained through pre-treatment.
Reagent: DMEM cell complete culture solution (Gibco company)；Fetal calf serum (Hyclone company)；Pancreatin cell dissociation
Liquid (Chinese holly company)；Penicillin streptomycin mixed liquor is dual anti-(Qilu Pharmaceutical Co., Ltd.).
(3) experimental method
A cell culture
A549 cell (human lung adenocarcinoma) is taken, is incubated at 37 DEG C, 5%CO with the DMEM culture solution containing 10% fetal calf serum2Training
It supports in case, logarithmic growth phase cell is tested.
B mtt assay measures influence of the compound to different activity of tumor cells
By CO2The tumour cell cultivated in incubator is digested with 0.25% pancreatin, is blown and beaten into single cell suspension, will be thin
Born of the same parents' suspension is inoculated in (1 × 10 in 96 orifice plates4/ hole), culture is for 24 hours.Compound is dissolved with DMSO, is added in 96 orifice plates, and culture is for 24 hours
Afterwards, 20 μ L MTT, 37 DEG C of culture 4h are added in every hole.It discards supernatant, 150 μ L DMSO, which are added, in every hole is completely dissolved first a ceremonial jade-ladle, used in libation, uses enzyme
Mark instrument measures absorbance value at 490nm wavelength, its cell mortality is calculated, with IC50Value indicates the cytotoxic activity of compound.
C statistical method
All data with (X ± SD) display, using 5 software analyzing and processing data of GraphPad Prism, are examined using t
It tests with the presence or absence of significant difference between observation each group and blank group, P < 0.05 is significant difference.
D mtt assay measures cell inhibitory rate result (n=5), to the half inhibiting rate of human lung adenocarcinoma cell (A549)
IC50 value is 21.07 ± 3.72 μ g/mL.
The result shows that thinfruit hypecoum herb medicinal material is inhibited to the proliferation of human lung adenocarcinoma cell (A549), show this
Medicinal material has anti-tumor activity, can be used for developing anti-tumor drug.
Test the experimental study of 2. the compounds of this invention anti tumor activity in vitro
(1) experimental cell system
Human lung adenocarcinoma (A549) cell and human gastric cancer (MGC-803) cell are purchased from Cell Bank of Chinese Academy of Sciences.
(2) experimental drug and reagent
Experimental drug: using the isolated compound leptocaramine of embodiment 1；
Positive control drug: adriamycin (Doxorubicin) is purchased from Wanle Pharmaceutical Co Ltd, Shenzhen, lot number: 1612E1；
Reagent: DMEM cell complete culture solution (Gibco company)；Fetal calf serum (Hyclone company)；Pancreatin cell dissociation
Liquid (Chinese holly company)；Penicillin streptomycin mixed liquor is dual anti-(Qilu Pharmaceutical Co., Ltd.).
(3) experimental method
A cell culture
A549 cell (human lung adenocarcinoma) and MGC-803 cell (human gastric cancer) are taken, is cultivated with the DMEM containing 10% fetal calf serum
Liquid is incubated at 37 DEG C, 5%CO2In incubator, logarithmic growth phase cell is tested.
B mtt assay measures influence of the compound to different activity of tumor cells
By CO2The two kinds of tumour cells cultivated in incubator are digested with 0.25% pancreatin respectively, and piping and druming is at unicellular outstanding
Liquid, by cell suspension inoculation (1 × 10 in 96 orifice plates4/ hole), culture is for 24 hours.Compound is dissolved with DMSO, is added in 96 orifice plates,
After culture for 24 hours, 20 μ L MTT, 37 DEG C of culture 4h are added in every hole.It discards supernatant, 150 μ L DMSO, which are added, in every hole keeps first a ceremonial jade-ladle, used in libation completely molten
Solution, measures absorbance value with microplate reader at 490nm wavelength, its cell mortality is calculated, with IC50Value indicates the cell of compound
Cytotoxic activity.
C statistical method
All data with (X ± SD) display, using 5 software analyzing and processing data of GraphPad Prism, are examined using t
It tests with the presence or absence of significant difference between observation each group and blank group, P < 0.05 is significant difference.
D mtt assay measures cell inhibitory rate result (n=5), and experimental result is shown in Table 2.
Inhibiting effect of 2. the compounds of this invention of table to human lung adenocarcinoma cell and gastric carcinoma cells
The result shows that noval chemical compound leptocaramine is to human lung adenocarcinoma cell (A549) and gastric carcinoma cells (MGC-
803) proliferation has significant inhibiting effect, shows that the compound has preferable anti-tumor activity, can be used for developing anti-
Tumour medicine.
To sum up, especially aobvious to the inhibiting effect of human lung adenocarcinoma present invention discover that thinfruit hypecoum herb medicinal material can be antitumor
It writes, while the present invention isolated compound leptocaramine from thinfruit hypecoum herb medicinal material, also has specific anti-
Tumor promotion, especially has specific inhibitory effect to adenocarcinoma of lung and gastric cancer, and application prospect is excellent.
Claims (10)
1. a kind of isoquinoline alkaloid compound or its pharmaceutically acceptable salt or its solvate shown in formula (I):
Wherein, R1、R2Separately it is selected from hydrogen, hydroxyl, C1~C4Alkoxy；R3Selected from-(CH2)mNH(CH2)nCH3, m, n difference
Independently selected from 0~3 integer.
2. compound according to claim 1, it is characterised in that: R1、R2It is methoxyl group, and/or, m 2, and/or, n
It is 0.
3. compound according to claim 1 or 2, it is characterised in that: the compound is
4. a kind of preparation method of compound described in claims 1 to 3 any one, it is characterised in that: the following steps are included:
Take the dry herb of thinfruit hypecoum herb, pulverize and sieve, with miscible with water solvent extraction 1~3 time, combined extract, after concentration with
Water dispersion is chromatographed through macroreticular resin or micro-porous resin column after water phase concentration, is eluted with solvent through extracting, then through silica gel column chromatography,
Mixed solvent gradient elution prepares column through C18 after TLC is detected, solution elution to get.
5. the preparation method according to claim 4, it is characterised in that: the solvent miscible with water is ethyl alcohol, and/
Or, the extraction time is 3 times, and/or, each extraction time is 12h, and/or, Extraction solvent volume used every time
Mass ratio with the dry herb of thinfruit hypecoum herb is 4~20L:1kg, preferably 10L:1kg.
6. preparation method according to claim 4 or 5, it is characterised in that: the extractant is petroleum ether, and/or, institute
The volume ratio for stating extractant and aqueous solution is 0.5~10:1, preferably 1.5:1.
7. preparation method according to any one of claim 4 to 6, it is characterised in that: the macroreticular resin is D101, AB-8
Type macroreticular resin, the micro-porous resin are MCI resin；And/or used in the macroreticular resin or micro-porous resin column chromatographic elution
Solvent be followed successively by water and methanol；And/or the silica gel column chromatography solvent for use is methylene chloride-methanol solvent, and elutes ladder
Degree is methylene chloride: the volume ratio of methanol is 9:1,8:2,7:3,6:4,5:5,4:6,3:7；And/or the C18 column elution
Solution is the mixed solution of the acetonitrile that volume ratio is 15:85 and phosphate aqueous solution, it is preferable that phosphoric acid in the phosphate aqueous solution
Mass concentration be 0.1%.
8. compound described in a kind of claims 1 to 3 any one or its pharmaceutically acceptable salt or its solvate
Purposes, it is characterised in that: for preventing and/or treating tumour, it is preferable that the tumour is adenocarcinoma of lung and/or gastric cancer.
9. a kind of pharmaceutical composition for treating tumour, it is characterised in that: it is with the described in any item chemical combination of claims 1 to 3
Object or its solvate or its pharmaceutically acceptable salt are active constituent, in addition pharmaceutically acceptable auxiliary material is prepared
Preparation.
10. a kind of purposes of thinfruit hypecoum herb, it is characterised in that: for preventing and/or treating tumour, it is preferable that described is swollen
Tumor is human lung adenocarcinoma.
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Cited By (2)
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| CN113372354A (en) * | 2021-05-25 | 2021-09-10 | 中国科学院西北高原生物研究所 | Preparation method of violaxanthine |
| CN114149440A (en) * | 2021-11-22 | 2022-03-08 | 南昌大学 | Preparation and application of isoquinoline alkaloid with benzoquinone reductase induction activity |
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Cited By (3)
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| CN113372354A (en) * | 2021-05-25 | 2021-09-10 | 中国科学院西北高原生物研究所 | Preparation method of violaxanthine |
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| CN114149440B (en) * | 2021-11-22 | 2023-03-14 | 南昌大学 | Preparation and application of isoquinoline alkaloid with benzoquinone reductase induction activity |
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