CN113200911B - Quinoline alkaloid compound and preparation method and application thereof - Google Patents
Quinoline alkaloid compound and preparation method and application thereof Download PDFInfo
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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
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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 formula (I). The preparation method comprises extracting Thalictrum Sichuan-type Thalictrum aquilegifolium with high concentration methanol, high concentration acetone/water or high concentration ethanol/water, mixing the extractive solutions, filtering, and concentrating under reduced pressure to obtain extract; loading the extract into a column by a silica gel dry method, and performing silica gel column chromatography; gradient eluting with chloroform-acetone solution; separating and purifying the 9:1 part of the eluent by high-pressure liquid chromatography and gel column chromatography to obtain the required quinoline alkaloid compound. The invention also discloses application of the compound, and an activity test shows that the compound has a good inhibition effect on tobacco mosaic virus. The compound disclosed by the invention is novel in structure, has good activity of resisting the tobacco mosaic virus, and can be used as a lead compound for resisting the tobacco mosaic virus for researching and developing a pharmaceutical preparation for resisting the tobacco mosaic virus.
Description
Technical Field
The invention belongs to the technical field of phytochemistry, and particularly relates to a novel quinoline alkaloid compound extracted from a whole plant of Thalictrum cyrtonema, and a preparation method and application thereof.
Background
Thalictrum yunnanensis (academic name:Thalictrum finetii) Is one of dicotyledonous plant, ranunculaceae, and Thalictrum. Is distributed in southeast part of the Tibetan of China and western part of Sichuan and grows in hillside grass slopes and forest Bian Huo forests. The Thalictrum yunnanense is a common traditional Chinese medicine in Yunnan province, has the effects of promoting diuresis, eliminating dampness and toxin, and treating the main heat syndrome and the heart, and is often used for treating cold-dampness diarrhea, wind-heat cough, conjunctival congestion, swelling and pain, carbuncle, sore, furuncle and other diseases.
At present, searching for high-efficiency low-toxicity antiviral active molecules from natural plants is also a research hotspot of the current natural product chemistry, and a plurality of medicinal plant resources are widely used for treating various viral infection diseases, such as radix isatidis, honeysuckle, liquorice, radix sophorae flavescentis, rheum officinale, chrysanthemum and the like in clinic. The Yunnan natural medicine has rich resource and is mutually blended with the national diversity, and various special medicines are proved to have antiviral efficacy in the long-term folk medicine application, so the prospect of finding the virus inhibitor from the special medicinal plant resource is very wide.
Quinoline alkaloids exist in many natural plants and have a variety of biological activities. Because quinoline alkaloid compounds have such broad-spectrum pharmacological activity, researchers at home and abroad have conducted 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 Tang-grass in Yunnan province, and the compound has no related report so far, and the compound has remarkable activity of resisting tobacco mosaic virus and can be used as a lead compound of biological pesticides for preventing and treating tobacco mosaic.
Disclosure of Invention
The first object of the present invention is to provide a quinoline alkaloid compound, the second object of the present invention is to provide a preparation method of the quinoline alkaloid compound, and the third object of the present invention is to provide an application of the quinoline alkaloid compound.
The first object of the present invention is achieved by a quinoline alkaloid compound having the formula C 17 H 17 NO 3 The structural formula is shown as formula (I):
the compound is named as: 4-acetyl-6-methyl-7- (3-methyl-2-oxobutyl-3-enyl) -quinolin-2 (1)H) -a ketone; the English name is: 4-Acetyl-6-methyl-7- (3-methyl-2-oxout-3-enyl) quinone-2 (1)H)-one。
The second object of the present invention is achieved by a process for preparing the quinoline alkaloid compound, comprising the steps of:
(1) Extracting the whole plant of Thalictrum cyrtonema with a first solvent, and concentrating to obtain an extract;
(2) Dissolving the extract with a second solvent, performing silica gel column chromatography, performing gradient elution with chloroform-acetone solution, and collecting eluent with the volume ratio of chloroform-acetone solution of 9:1;
(3) Separating and purifying the eluent by high-pressure liquid chromatography to obtain the compound shown in the formula (I).
The third object of the invention is realized in such a way that the application of the quinoline alkaloid compound is the application in preparing medicines for resisting tobacco mosaic virus.
The beneficial effects of the invention are as follows:
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 a simple structure, obvious activity of resisting the tobacco mosaic virus, has good application prospect in preparing biological pesticides resisting the tobacco mosaic virus, and can be used as a lead compound for researching and developing anti-mosaic virus drugs for researching and developing anti-mosaic virus drug preparations.
3. The preparation method of the compound is simple, the raw materials are sufficient and easy to obtain, and the industrial production is easy to realize.
Drawings
FIG. 1 is a nuclear magnetic resonance carbon spectrum of the quinoline alkaloid compound of the embodiment 1;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of the quinoline alkaloid compound of the embodiment 1;
fig. 3 is a main HMBC-related diagram of the quinoline alkaloid compound of example 1.
Detailed Description
The invention is described in further detail below with reference to the drawings and examples, but is not limited in any way to any changes or modifications made based on the teachings of the invention, which fall within the scope of the invention.
The percentages used in the present invention are mass percentages unless otherwise indicated.
The invention discloses 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) Extracting the whole plant of Thalictrum cyrtonema with a first solvent, and concentrating to obtain an extract;
(2) Dissolving the extract with a second solvent, performing silica gel column chromatography, performing gradient elution with chloroform-acetone solution, and collecting eluent with the volume ratio of chloroform-acetone solution of 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 extraction after 24 h-72 h, the weight ratio of the first solvent to the raw materials is 2-4:1, and the extraction times are 3-5 times.
In the step 1, the first solvent is 80-100% of methanol or 80-100% of ethanol or 60-90% of acetone aqueous solution.
The extractum is packed by 160-300 meshes of silica gel dry method with the weight ratio of 2-4 times for silica gel column chromatography.
In the step 2, the volume ratio of the chloroform-acetone solution of the 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 separation and purification by 21.2 mm multiplied by 250 mm,5µmC of (2) 18 The chromatographic column has the flow rate of 20 mL/min, the mobile phase of 68% methanol, the detection wavelength of an ultraviolet detector of 342nm, each sample injection of 0.5-1.0 mL, the collection of chromatographic peaks of 31.8min, and the evaporation to dryness after accumulation for a plurality of times.
The compound obtained in the step 3 can be dissolved by pure methanol, then methanol is used as a mobile phase, and gel column chromatography is used for separation so as to further separate and purify, thus obtaining a pure product with higher purity.
The invention also provides application of the compound in preparing a medicine for resisting tobacco mosaic virus.
The tobacco leaf raw materials used in the invention are not limited by regions and varieties, the invention can be realized, and the invention is further described by the following Sichuan Thalictrum scoparium which is sourced from different producing regions:
example 1
The Thalictrum Sichuan of this example is prepared from Sichuan mountain, pulverizing 2.0. 2.0 kg Thalictrum Sichuan grass to 50 mesh, extracting with 95% methanol water solution for 5 times, extracting 24 h each time, mixing the extractive solutions, filtering, and concentrating under reduced pressure to obtain extract 112 g. Dissolving the extract with 2.0 times of methanol, mixing with 150 g 100 mesh crude silica gel, subjecting to silica gel column chromatography with 0.65 kg mesh silica gel column chromatography, gradient eluting with 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, 1:2 chloroform-acetone, TLC monitoring, mixing the same parts to obtain 8 parts, separating the chloroform-acetone eluting part with 9:1 volume by adopting Mimehlam 1100 semi-preparative high performance liquid chromatography, and separating with 68% methanol aqueous solution as mobile phase to obtain Zorbax SB-C18 (21.2 mm ×250 mm, 5)µm) Preparing a column as a stationary phase, wherein the flow rate is 20 ml/min, the detection wavelength of an ultraviolet detector is 342nm, sampling is performed for 0.5 mL each time, collecting chromatographic peaks of 31.8min, accumulating for multiple times, and evaporating to dryness to obtain a crude compound; dissolving the obtained product with methanol again, and separating with Sephadex LH-20 gel column chromatography with methanol as mobile phase to obtain the pure product of the compound.
The compound prepared in example 1 was taken and 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 spectrum data are 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； 1 H and 13 C NMR data (C 5 D 5 n, 500 and 125 MHz), see table 1. Positive ion mode ESIMSm/z306 [M+Na] + The method comprises the steps of carrying out a first treatment on the surface of the Positive ion mode HRESIMSm/z306.1112 [M+Na] + (calculated 306.1106, C) 17 H 17 NNaO 3 ). 1 H-NMR， 13 C-NMR spectrum numberAs shown in fig. 2,3, 1 h NMR 13 The C NMR data are shown in Table 1:
TABLE 1 Compounds prepared in example 1 1 H NMR 13 C 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 ring (1615, 1536 and 1434 cm) -1 ) A characteristic functional group; high resolution mass spectrometry (HRESIMS) gives an excimer ion peak 306.1112 [ M+Na ]] + The molecular formula of the compound can be determined to be C 17 H 17 NO 3 The degree of unsaturation was 10. Bonding of 1 H and 13 c and HSQC NMR data showed that the compound included a 1,2,4, 5-tetrasubstituted benzene ring (C-5~C-8, C-4a and C-8a, H-5 and H-8), a 3-methyl-2-oxobutyl-3-enyl structural fragment (C-4 '-8', H) 2 -4'、H 2 -7' and H 3 -8 '), an acetyl group (C-1 ', C-2', and H 3 -2') a-NH-CO-CH-C-group (C-2-4, H-1, H-3 and NH). In order to satisfy 10 unsaturations of the compound, in addition to three carbonyl groups, one double bond, a benzene ring, there should be one benzene ring and a six-membered ring quinoline-2 (1) formed by-NH-CO-CH-C-groupsH) -a ketone structure. The inference can be further confirmed by the 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 HMBC of C-4, C-4a, C-8 a.
After the parent backbone of the compound is determined, the remaining substituent positions can be determined by further analysis of its HMBC correlation. From the correlation of H-2 'with HMBC of C-4, H-3 with C-1', it can be determined that the acetyl substitution is at the C-4 position; from the correlation of H-4 'with HMBC of C-6, C-7, C-8,H-8 and C-4', it was determined that 3-methyl-2-oxobutyl-3-enyl was substituted at the C-7 position. Finally, according to H 3 -3 'is related to HMBC of C-5, C-6, C-7, it can be determined that the methyl (C-3') substitution is at the C-6 position. To this end, the compounds of the inventionThe structure was confirmed and identified as: 4-acetyl-6-methyl-7- (3-methyl-2-oxobutyl-3-enyl) -quinolin-2 (1)H) -a ketone.
Example 2
The grass of Thalictrum Sichuan in this example was collected in Yunnan Lijiang, 4kg of grass of Thalictrum Sichuan was crushed to 30 mesh, extracted with 95% ethanol aqueous solution for 4 times, each extraction was 48 and h, the extracts were combined, filtered and concentrated under reduced pressure to obtain an extract 235 g. Dissolving the extract with 2.0 times of methanol, mixing with 250 g crude silica gel of 80 meshes, subjecting 1.2 kg silica gel column to silica gel column chromatography, gradient eluting with chloroform-water solution of volume ratio of 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, 1:2, TLC monitoring, mixing the same parts to obtain 8 parts, separating chloroform-acetone eluting part of volume ratio of 9:1 with Mimehlan 1100 semi-preparative high performance liquid chromatography, separating with 68% methanol as mobile phase, and Zorbax SB-C18 (21.2 mm ×250 mm, 5)µm) Preparing a column as a stationary phase, wherein the flow rate is 20 ml/min, the detection wavelength of an ultraviolet detector is 342nm, sampling is performed for 0.8 mL each time, collecting chromatographic peaks of 31.8min, accumulating for multiple times, and evaporating to dryness to obtain a crude compound; dissolving the obtained product with pure methanol again, and separating with Sephadex LH-20 gel column chromatography with pure methanol as mobile phase to obtain the pure product.
The structural identification of the compound obtained in this example was the same as that of example 1, and it was confirmed that the compound prepared in this example was the quinoline alkaloid compound-4-acetyl-6-methyl-7- (3-methyl-2-oxobutyl-3-enyl) -quinoline-2 (1)H) -a ketone.
Example 3
Collecting Thalictrum Yunnanensis in Yunnan Lijiang, pulverizing 5 kg Thalictrum Yunnanensis to 40 mesh, extracting with 75% acetone aqueous solution for 3 times with ultrasound, extracting 72 h each time, mixing the extractive solutions, filtering, and concentrating under reduced pressure to obtain extract 385 g. Dissolving the extract with 1.6 times of methanol, mixing with 450. 450 g coarse silica gel of 90 meshes, subjecting to silica gel column chromatography with 2.4 kg silica gel column of 180 meshes, and gradient eluting with chloroform-acetone of volume ratio of 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, 1:2, TLC monitoring, mixing the same parts to obtain 8 parts, whereinChloroform-acetone eluting part with volume ratio of 9:1 is separated by adopting Mirabilin 1100 semi-preparative high performance liquid chromatography, 68% methanol water solution is used as mobile phase, zorbax SB-C18 (21.2 mm ×250 mm, 5)µm) Preparing a column as a stationary phase, wherein the flow rate is 20 ml/min, the detection wavelength of an ultraviolet detector is 342nm, sampling is performed for 0.6 mL each time, collecting chromatographic peaks of 31.8min, accumulating for multiple times, and evaporating to dryness; dissolving the obtained product with pure methanol again, and separating with Sephadex LH-20 gel column chromatography with pure methanol as mobile phase to obtain brown jelly.
The structural identification of the compound obtained in this example was the same as that of example 1, and it was confirmed that the compound prepared in this example was the quinoline alkaloid compound-4-acetyl-6-methyl-7- (3-methyl-2-oxobutyl-3-enyl) -quinoline-2 (1)H) -a ketone.
Example 4 test for Activity against tobacco mosaic
The activity test of tobacco mosaic virus resistance is carried out by taking any quinoline alkaloid compound prepared in the example 1.
The test method comprises the following steps: the tobacco mosaic virus resistance activity of the compound is measured by adopting a half leaf method when the mass concentration of the medicament is 50 mg/L. Selecting leaf suitable for testing from plants of 5-6 years old flue-cured tobacco (leaf row is normal, disease and pest free), uniformly spreading fine silicon carbide on leaf, and writing with brush to obtain tobacco mosaic virus source (3.0X10) -3 ) Uniformly smearing on the leaves scattered with silicon carbide, immediately placing the leaves in a culture dish containing liquid medicine for 20 min after the inoculation of all the selected leaves is finished, taking out, wiping off water drops and the liquid medicine on the leaves, recovering and discharging the two half leaves in a glass jar paved with toilet paper for moisturizing, covering a glass cover, controlling the temperature (23+/-2) DEG C, placing the two half leaves in a greenhouse for natural light irradiation, and enabling a dead spot to be visible in 2-3 d, wherein the other half of leaves are used as a contrast in each treatment, and 1 group of treatments of commodity Ningnan mycin are used as a contrast, and calculating the relative inhibition ratio according to the following formula:
XI％=(CK-T)／CK×100％
wherein, X: relative inhibition (%), CK: the number of the dead spots of the half-leaf virus-collecting leaves soaked in clear water is T, and the number of the dead spots of the half-leaf virus-collecting leaves soaked in the liquid medicine is T.
Results: the relative inhibition rate of the compound is calculated to be 52.5 percent, which exceeds the relative inhibition rate of control Ningnan mycin by 33.8 percent, thus indicating that the compound has good tobacco mosaic virus resistance.
Claims (3)
1. A quinoline alkaloid compound has a structural formula shown in a formula (I):
2. a process for preparing a compound according to claim 1, comprising the steps of:
(1) Extracting the whole plant of Thalictrum cyrtonema with a first solvent, and concentrating to obtain an extract;
(2) Dissolving the extract with a second solvent, performing silica gel column chromatography, performing gradient elution with chloroform-acetone solution, and collecting eluent with the volume ratio of chloroform-acetone solution of 9:1;
(3) Separating and purifying the eluent by high-pressure liquid chromatography to obtain a compound shown in a formula (I);
in the step (1), the raw materials are soaked in a first solvent for extraction after 24-h-72 h, the weight ratio of the first solvent to the raw materials is 2-4:1, and the extraction times are 3-5 times;
in the step (1), the first solvent is 80-100% of methanol aqueous solution or 80-100% of ethanol aqueous solution or 60-90% of acetone aqueous solution;
in the step (2), the extractum is filled with 160-300 meshes of silica gel in a dry method according to the weight ratio of 2-4 times for silica gel column chromatography;
in the step (2), the volume ratio of the chloroform-acetone solution subjected to 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 or ethanol or acetone;
in the step (3), the high pressure liquid chromatography separation and purification are carried out by adopting 21.2 mm× 250 mm，5 µmC of (2) 18 Chromatographic column, flow rate of 20 mL/min, mobile phase of 68% methanol, wavelength of 342nm detected by ultraviolet detector, sampling 0.5-1.0 mL each time, collecting chromatographic peak of 31.8min, accumulating for multiple times, and evaporating to dryness;
the compound obtained in the step (3) can be dissolved by pure methanol, methanol is taken as a mobile phase, and gel column chromatography is used for separation so as to further separate and purify, thus obtaining a pure product with higher purity.
3. Use of a compound according to claim 1 for the preparation of a medicament against tobacco mosaic virus.
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