CN113200911A - Quinoline alkaloid compound and preparation method and application thereof - Google Patents
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The invention discloses a quinoline alkaloid compound and a preparation method and application thereof. The structural formula of the compound is shown as a formula (I). The preparation method comprises extracting Thalictrum delavayi Thalictrum with high concentration methanol, high concentration acetone/water or high concentration ethanol/water, mixing extractive solutions, filtering, and concentrating under reduced pressure to obtain extract; packing the extract into a column by a silica gel dry method for silica gel column chromatography; performing gradient elution by using chloroform-acetone solution; and further separating and purifying the 9:1 part of the eluent by using high pressure liquid chromatography and separating by using gel column chromatography to obtain the required quinoline alkaloid compound. The invention also discloses application of the compound, and activity tests show that the compound has a good inhibition effect on tobacco mosaic virus. The compound has novel structure, better activity of resisting tobacco mosaic virus and can be used for resisting smokeThe lead compound of the grass mosaic virus is used for research and development of a tobacco mosaic virus resistant pharmaceutical preparation.
Description
Technical Field
The invention belongs to the technical field of phytochemistry, and particularly relates to a quinoline alkaloid novel compound extracted from a whole plant of thalictrum delavayi, a preparation method and application thereof.
Background
Tangutong grass (academic name:Thalictrum finetii) Is a species of dicotyledonous plant of Ranunculaceae, Thalictrum. Distributed in southeast and west Sichuan of Tibet, and grown on grass slope, forest edge or forest. Thalictrum Yunnanense Tsiang is a common Chinese medicinal material in Yunnan folk, has the effects of clearing heat and promoting diuresis, eliminating dampness and removing toxicity, relieving mental fever and the like, and is commonly used for treating diseases such as cold-dampness diarrhea and dysentery, cough due to wind-heat, conjunctival congestion and swelling, carbuncle, sore and furuncle and the like.
At present, the search for high-efficiency and low-toxicity antiviral active molecules from natural plants is also a research hotspot of the current natural product chemistry, and clinically, a plurality of medicinal plant resources are widely used for treating various viral infection diseases, such as isatis root, honeysuckle, liquorice, sophora flavescens, rhubarb, chrysanthemum and the like. The natural medicine resources of Yunnan are very rich and are mutually blended with national diversity, and various characteristic medicines are proved to have antiviral efficacy in long-term folk medicine application, so that the prospect of finding the virus inhibitor from the characteristic medicinal plant resources is very wide.
Quinoline alkaloid compounds occur in many natural plants and have a variety of biological activities. Due to the fact that quinoline alkaloid compounds have broad-spectrum pharmacological activity, researchers at home and abroad carry out intensive research on the compounds, and besides searching the compounds from natural products, the compounds with better pharmacological activity are obtained through structural modification. By researching the structure-activity relationship of the compounds, more quinoline alkaloid compounds can be further researched and developed, and effective lead compounds and active groups can be searched. The invention separates a new quinoline alkaloid compound from Yunnan Sichuan Yunnan Tang pine grass, and the compound has no relevant report so far, and is worth mentioning that the compound has obvious activity of resisting tobacco mosaic virus and can be used as a lead compound of a biological pesticide for preventing and treating tobacco mosaic disease.
Disclosure of Invention
The first purpose of the invention is to provide a quinoline alkaloid compound, the second purpose of the invention is to provide a preparation method of the quinoline alkaloid compound, and the third purpose of the invention is to provide application of the quinoline alkaloid compound.
The first object of the invention is achieved by a quinoline alkaloid compound of the formula C17H17NO3The structural formula is shown as the formula (I):
the compound was named: 4-BAcyl-6-methyl-7- (3-methyl-2-oxobutyl-3-enyl) -quinoline-2 (1)H) -a ketone; the English name is: 4-Acetyl-6-methyl-7- (3-methyl-2-oxobout-3-enyl) quinolin-2 (1)H)-one。
The second object of the present invention is achieved by a method for preparing quinoline alkaloid compounds, comprising the steps of:
(1) taking the whole plant of thalictrum citriodorum as a raw material, extracting with a first solvent, and concentrating into an extract;
(2) dissolving the extract with a second solvent, performing silica gel column chromatography, performing gradient elution with chloroform-acetone solution, and collecting the eluate with the volume ratio of chloroform-acetone solution being 9: 1;
(3) separating and purifying the eluent by high pressure liquid chromatography to obtain the compound shown in the formula (I).
The third purpose of the invention is realized by the application of the quinoline alkaloid compound in the preparation of the anti-tobacco mosaic virus medicine.
The invention has the beneficial effects that:
1. the quinoline alkaloid compound has a novel structure, and provides a new way for researching and developing more quinoline alkaloid compounds and searching effective lead compounds and active groups from the quinoline alkaloid compounds.
2. The quinoline alkaloid compound has simple structure, obvious activity of resisting tobacco mosaic virus, good application prospect in preparing biological pesticide for resisting tobacco mosaic virus, and can be used as a leading compound for researching and developing anti-mosaic virus medicaments.
3. The preparation method of the compound is simple, the raw materials are sufficient and easy to obtain, and the industrialized production is easy to realize.
Drawings
FIG. 1 is a nuclear magnetic resonance carbon spectrum of the quinoline alkaloid compound of example 1;
FIG. 2 is the NMR spectrum of the quinoline alkaloid compound of example 1;
FIG. 3 is a schematic representation of the main HMBC correlation of the quinoline alkaloid compounds of this example 1.
Detailed Description
The invention is further described in detail below with reference to the drawings and examples, but the invention is not limited in any way, and any changes or modifications made based on the teachings of the invention fall within the scope of the invention.
All percentages used in the present invention are mass percentages unless otherwise indicated.
The invention relates to a quinoline alkaloid compound, which has a structural formula shown in a formula (I):
the invention also provides a preparation method of the compound, which comprises the following steps:
(1) taking the whole plant of thalictrum citriodorum as a raw material, extracting with a first solvent, and concentrating into an extract;
(2) dissolving the extract with a second solvent, performing silica gel column chromatography, performing gradient elution with chloroform-acetone solution, and collecting the eluate with the volume ratio of chloroform-acetone solution being 9: 1;
(3) separating and purifying the eluent by high pressure liquid chromatography to obtain the compound shown in the formula (I).
In the step 1, the raw materials are soaked in a first solvent for 24-72 hours and then extracted, wherein the weight ratio of the first solvent to the raw materials is 2-4: 1, and the extraction times are 3-5.
In the step 1, the first solvent is 80-100% of methanol, 80-100% of ethanol or 60-90% of acetone aqueous solution.
And (3) filling the extract into a column by a 160-300-mesh silica gel dry method in an amount which is 2-4 times the weight of the extract, and performing silica gel column chromatography.
In the step 2, the volume ratio of the chloroform-acetone solution for gradient elution is 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1 and 1: 2.
In the step 2, the second solvent is methanol, ethanol or acetone.
In the step 3, the high pressure liquid chromatography is used for separating and purifying the mixture by 21.2 mm multiplied by 250 mm, 5µmC of (A)18And (3) carrying out chromatographic column chromatography, wherein the flow rate is 20 mL/min, the mobile phase is 68% methanol, the detection wavelength of an ultraviolet detector is 342nm, 0.5-1.0 mL of sample is fed every time, collecting a chromatographic peak for 31.8min, and evaporating to dryness after multiple accumulation.
And (3) dissolving the compound obtained in the step (3) by using pure methanol, taking the methanol as a mobile phase, and separating by using gel column chromatography to further separate and purify to obtain a pure product with higher purity.
The invention also provides application of the compound in preparing a tobacco mosaic virus resistant medicament.
The tobacco raw materials used in the invention are not limited by regions and varieties, and the invention can be realized, and the invention is further explained by Thalictrum cyrtonema Hance from different producing areas:
example 1
In the embodiment, the thalictrum citriodorum is derived from Sichuan Liangshan, 2.0 kg of thalictrum citriodorum is crushed into 50 meshes, extracted with 95% methanol water solution for 5 times, each time for 24 hours, the extracting solutions are combined, filtered and concentrated under reduced pressure to obtain 112 g of extract. Dissolving the extract with 2.0 times of methanol, mixing with 150 g of 100 mesh crude silica gel, loading 0.65 kg of 160 mesh silica gel into column, performing silica gel column chromatography, gradient eluting with chloroform-acetone at volume ratio of 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, 1:2, monitoring by TLC, mixing the same fractions to obtain 8 fractions, wherein the chloroform-acetone eluted fraction at volume ratio of 9:1 is separated by HPLC with ANJIERAN 1100 semi-preparative HPLC, using 68% methanol water solution as mobile phase, and Zorbax SB-C18 (21.2 mm × 250 mm, 5 mm, 21.2 mm × 250 mm, 5 mm) as mobile phaseµm) The preparation column is a stationary phase, the flow rate is 20 mL/min, the detection wavelength of an ultraviolet detector is 342nm, 0.5 mL of sample is injected each time, a chromatographic peak of 31.8min is collected, and a crude compound product can be obtained by evaporation after multiple accumulation; dissolving the obtained product with methanol again, taking the methanol as a mobile phase, and separating by Sephadex LH-20 gel column chromatography to obtain the pure product of the compound.
The compound prepared in example 1 was subjected to structural identification by MS, HRMS, 1H NMR, 1H and 13C NMR, HMBC and DEPT to obtain a spectrum of the compound, and the spectral data were as follows: UV (MeOH)λ max (log ε): 210 (4.25), 235 (3.64) and 342 nm；IR (KBr) ν max 3276、2928、1682、1665、1650、1615、1536、1434、1146、895、764；1h and13C NMR data (C5D5n, 500 and 125 MHz), see table 1. Positive ion mode ESIMSm/z306 [M+Na]+(ii) a Positive ion mode HRESIMSm/z306.1112 [M+Na]+(calculated 306.1106, C17H17NNaO3). 1H-NMR，13The C-NMR spectrum data are respectively shown in FIGS. 2 and 3,1h NMR and13the C NMR data are shown in Table 1:
table 1 preparation of compound of example 11H NMR and13c NMR data (CDCl)3)
The structure analysis process is as follows: infrared spectrum (potassium bromide tablet) shows that the compound has amino group (3276 cm)-1) Carbonyl (1682, 1665 and 1650 cm)-1) Aromatic rings (1615, 1536 and 1434 cm)-1) A characteristic functional group; high resolution mass spectrometry (HRESIMS) gave an excimer ion peak 306.1112 [ M + Na ]]+Determining the formula of the compound as C17H17NO3The unsaturation degree was 10. Bonding of1H and13NMR data of C and HSQC show that the compound comprises a 1,2,4, 5-tetra-substituted benzene ring (C-5-C-8, C-4a and C-8a, H-5 and H-8) and a 3-methyl-2-oxobutyl-3-alkenyl structural fragment (C-4 '-8', H-4)2-4'、H2-7' and H3-8'), one acetyl group (C-1', C-2', and H3-2'), one-NH-CO-CH-C-group (C-2. about.4, H-1, H-3 and NH). In order to satisfy the 10-degree of unsaturation of the compound, besides three carbonyl groups, a double bond and a benzene ring, the compound should also have a benzene ring and a six-membered quinoline-2 (1) formed by-NH-CO-CH-C-groupH) -a ketone structure. This inference can be further confirmed by the HMBC correlation of H-3 with C-2, C-4a, NH with C-2, C-3, C-8, C-4a, C-8a, H-8 with C-4a, C-8a, H-5 with C-4, C-4a, C-8 a.
After the parent framework of the compound is determined, the remaining substituent positions can be determined by further analysis of its HMBC association. The substitution of the acetyl group at the C-4 position can be determined by the correlation of H-2 'with C-4 and H-3 with C-1' HMBC; the substitution of 3-methyl-2-oxobutyl-3-enyl at the C-7 position was determined based on the correlation of H-4 'with HMBC at C-6, C-7, C-8, and H-8 with C-4'. Finally, according to H3The 3 'is related to HMBC at C-5, C-6, C-7, and the substitution of methyl (C-3') at C-6 can be determined. Thus far, the structure of the compounds of the present invention was confirmed and identified as: 4-acetyl-6-methyl-7- (3-methyl-2-oxobutyl-3-enyl) -quinoline-2 (1)H) -a ketone.
Example 2
In the embodiment, the thalictrum citriodorum is collected from Yunnan Lijiang, 4kg of thalictrum citriodorum is crushed into a sample, the sample is crushed into 30 meshes, the sample is extracted for 4 times by 95% ethanol water solution for 48 hours each time, the extracting solutions are combined, filtered and concentrated under reduced pressure to obtain 235 g of extract. Dissolving the extract with 2.0 times of methanol, mixing with 250 g of 80 mesh crude silica gel, loading 1.2 kg of 200 mesh silica gel into column, performing silica gel column chromatography, gradient eluting with chloroform-water solution at volume ratio of 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, 1:2, monitoring by TLC, mixing the same fractions to obtain 8 fractions, wherein the chloroform-acetone eluted fraction at volume ratio of 9:1 is separated by HPLC with ANJIERAN 1100 semi-preparative HPLC, using 68% methanol as mobile phase, and Zorbax SB-C18 (21.2 mm × 250 mm, 5 mm) as mobile phaseµm) The preparation column is a stationary phase, the flow rate is 20 mL/min, the detection wavelength of an ultraviolet detector is 342nm, 0.8 mL of sample is injected each time, a chromatographic peak of 31.8min is collected, and a crude compound product can be obtained by evaporation after multiple accumulation; and dissolving the obtained product with pure methanol again, taking the pure methanol as a mobile phase, and carrying out Sephadex LH-20 gel column chromatography separation to obtain a pure product of the compound.
The structural identification of the compound obtained in this example was performed in the same manner as in example 1, and it was confirmed that the compound prepared in this example was 4-acetyl-6-methyl-7- (3-methyl-2-oxobutyl-3-enyl) -quinoline-2 (1) which is the quinoline alkaloid compoundH) -a ketone.
Example 3
Collecting Thalictrum delavayi Franch from Yunnan Lijiang, and pulverizing 5 kg Thalictrum delavayi FranchPulverizing to 40 mesh, extracting with 75% acetone water solution with ultrasound for 3 times, each for 72 hr, mixing extractive solutions, filtering, and concentrating under reduced pressure to obtain 385 g extract. Dissolving the extract with 1.6 times of methanol, mixing with 450 g of 90 mesh crude silica gel, loading 2.4 kg of 180 mesh silica gel into column, performing silica gel column chromatography, gradient eluting with chloroform-acetone at volume ratio of 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, 1:2, monitoring by TLC, mixing the same fractions to obtain 8 fractions, wherein the chloroform-acetone eluted fraction at volume ratio of 9:1 is separated by HPLC with ANJIERAN 1100 semi-preparative HPLC, using 68% methanol water solution as mobile phase, and Zorbax SB-C18 (21.2 mm × 250 mm, 5 mm, 21.2 mm × 250 mm, 5 mm) as mobile phaseµm) The preparation column is a stationary phase, the flow rate is 20 mL/min, the detection wavelength of an ultraviolet detector is 342nm, 0.6 mL of sample is fed every time, a chromatographic peak of 31.8min is collected, and the chromatographic peak is evaporated to dryness after multiple accumulation; dissolving the obtained product with pure methanol again, taking the pure methanol as a mobile phase, and carrying out chromatographic separation by using a Sephadex LH-20 gel column to obtain a brown jelly, namely the pure product of the compound.
The structural identification of the compound obtained in this example was performed in the same manner as in example 1, and it was confirmed that the compound prepared in this example was 4-acetyl-6-methyl-7- (3-methyl-2-oxobutyl-3-enyl) -quinoline-2 (1) which is the quinoline alkaloid compoundH) -a ketone.
Example 4 test for tobacco mosaic disease resistance Activity
The quinoline alkaloid compounds prepared in example 1 were used for the activity test against tobacco mosaic virus.
The test method comprises the following steps: the activity of the compound of the invention against tobacco mosaic virus is measured by a half-leaf method when the mass concentration of the medicament is 50 mg/L. Selecting leaves suitable for testing (normal leaves, no disease and no insect) on plants of 5-6-year-old flue-cured tobacco, uniformly spraying fine carborundum on the leaves, and using a writing brush to apply a standby tobacco mosaic virus source (3.0 multiplied by 10)-3) Uniformly smearing on leaf blade sprinkled with carborundum, immediately placing in a culture dish containing medicinal liquid after all selected leaf blades are disinfected for 20 min, taking out, wiping off water drops and medicinal liquid on leaf blades, recovering and arranging two half leaves in a glass jar paved with toilet paper for moisture preservation, covering with a glass cover, and controlling temperature (23 +/-)2) And (3) placing the mixture in a greenhouse for natural light irradiation, and then, exposing dead spots after 2-3 d, wherein the other half of leaves are used as a reference for each treatment, and 1 group of treatments of commercial ningnanmycin are used as a comparison, and the relative inhibition rate is calculated according to the following formula:
XI％=(CK-T)／CK×100％
wherein, X: relative inhibition ratio (%), CK: the number of dead spots of half leaf after being soaked in clear water is one, and the number of dead spots of half leaf after being soaked in liquid medicine is one.
As a result: the relative inhibition rate of the compound is 52.5 percent and is 33.8 percent higher than that of a control ningnanmycin, so that the compound has good activity of resisting tobacco mosaic virus.
Claims (10)
1. A quinoline alkaloid compound has a structural formula shown in formula (I):
2. a process for preparing a compound of claim 1, comprising the steps of:
(1) taking the whole plant of thalictrum citriodorum as a raw material, extracting with a first solvent, and concentrating into an extract;
(2) dissolving the extract with a second solvent, performing silica gel column chromatography, performing gradient elution with chloroform-acetone solution, and collecting the eluate with the volume ratio of chloroform-acetone solution being 9: 1;
(3) separating and purifying the eluent by high pressure liquid chromatography to obtain the compound shown in the formula (I).
3. The preparation method according to claim 2, wherein in the step 1, the raw material is soaked in the first solvent for 24 to 72 hours and then extracted, wherein the weight ratio of the first solvent to the raw material is 2 to 4:1, and the extraction times are 3 to 5.
4. The method according to claim 2 or 3, wherein the first solvent in step 1 is 80-100% methanol aqueous solution, 80-100% ethanol aqueous solution, or 60-90% acetone aqueous solution.
5. The preparation method according to claim 2, wherein in the step 2, the extract is subjected to silica gel column chromatography by using a 160-300-mesh silica gel dry method in an amount which is 2-4 times the weight of the extract.
6. The preparation method according to claim 2, wherein in the step 2, the chloroform-acetone solution for gradient elution has volume ratios of 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1 and 1: 2.
7. The method according to claim 2, wherein in the step 2, the second solvent is methanol, ethanol, or acetone.
8. The method according to claim 2, wherein the step 3, the high pressure liquid chromatography is performed to separate and purify the extract by using 21.2 mm x 250 mm, 5µmC of (A)18And (3) carrying out chromatographic column chromatography, wherein the flow rate is 20 mL/min, the mobile phase is 68% methanol, the detection wavelength of an ultraviolet detector is 342nm, 0.5-1.0 mL of sample is fed every time, collecting a chromatographic peak for 31.8min, and evaporating to dryness after multiple accumulation.
9. The method according to claim 2, wherein the compound obtained in step 3 is dissolved in pure methanol, and the solution is further separated and purified by gel column chromatography using methanol as a mobile phase to obtain a pure product with higher purity.
10. The use of a compound as claimed in claim 1 for the preparation of a medicament against tobacco mosaic virus.
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