CN113087664A - Quinoline alkaloid compound and preparation method and application thereof - Google Patents
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Abstract
The invention belongs to the technical field of phytochemistry, and particularly relates to a quinoline alkaloid compound and a preparation method and application thereof. The compound has the molecular formula: c15H17NO2Which has the following structure:
the invention also discloses a preparation method and application of the compound. The invention separates a new compound from tobacco stems for the first time, determines the quinoline alkaloid compound by a nuclear magnetic resonance and mass spectrometry method, and characterizes the specific structure of the quinoline alkaloid compound. And the quinoline alkaloid compound has good activity of resisting tobacco mosaic virus: experiments on resisting tobacco mosaic virus show that the relative ratio of the quinoline alkaloid compoundsThe inhibition rate reaches 38.5%, and the activity of the inhibitor is higher than the relative inhibition rate (33.0%) of a reference substance ningnanmycin. The compound has good application prospect in preparing the anti-tobacco mosaic virus medicament. The compound has simple structure and good activity, and can be used as a guiding compound of a tobacco mosaic virus resistant medicament.
Description
Technical Field
The invention belongs to the technical field of phytochemistry, and particularly relates to a quinoline alkaloid compound and a preparation method and application thereof.
Background
Tobacco is a plant of the genus nicotiana of the family solanaceae, and is one of the most widely cultivated commercial crops in the world. China is the biggest tobacco producing country and consuming country in the world, and annual output can reach 4-5 hundred million tons. In the tobacco planting and cigarette production processes, more than 2 hundred million tons of waste tobacco materials, such as roots, stems, low-grade or defective tobacco leaves and the like of tobacco, are generated every year, and how to enhance the comprehensive utilization of the tobacco and the waste thereof has attracted extensive attention of researchers.
According to literature reports, more than 4000 compounds are identified from tobacco at present, and main components comprise diterpenoids, sesquiterpenes, flavonoids, alkaloids, coumarins and the like. Meanwhile, researches prove that the compounds have different pharmacological effects, such as antibiosis, antioxidation, antitumor, tobacco mosaic virus resistance and the like. Therefore, the improvement of the medicinal value of the tobacco and the waste thereof and the comprehensive utilization of the byproducts have very important significance.
Disclosure of Invention
The invention separates a new alkaloid compound with anti-tobacco mosaic virus activity from tobacco stems, and the compound has not been reported yet.
All percentages used in the present invention are mass percentages unless otherwise indicated.
In a first aspect, the present invention provides a quinoline alkaloid compound, wherein the molecular formula of the compound is:
C15H17NO2which has the following structure:
this compound was a brown gum, designated: 4-acetyl-7-isopropyl-6-methylquinolin-2(1H) -one, english name: 4-Acetyl-7-isoproyl-6-methylquinolin-2 (1H) -one.
The second aspect of the present invention provides a preparation method of the quinoline alkaloid compound described in the first aspect, specifically including the following steps:
A. extracting the extractum: taking tobacco stems as raw materials, crushing, carrying out ultrasonic extraction by using 90-99 wt% ethanol, adding an extracting solution into a mixed solution of ethyl acetate and 3 wt% tartaric acid, standing and layering the mixed solution, and then using Na2CO3Adjusting pH of water layer to 9.0, extracting with ethyl acetate, filtering, and concentrating under reduced pressure to obtain extract;
B. silica gel column chromatography: b, filling the extract obtained in the step A into a column by using a 200-300-mesh silica gel dry method, and performing silica gel column chromatography; gradient eluting with chloroform-methanol solution at volume ratio of 10:0, 9:1, 8:2, 7:3, 6:4, and 5:5 respectively, mixing the parts with the same polarity, collecting eluate of each part, and concentrating; wherein the mass ratio of the silica gel to the extract is 2-5; collecting eluate obtained by eluting with chloroform-methanol solution at volume ratio of 9:1, and making into first eluate; continuously separating the first eluent by using a silica gel chromatographic column, performing gradient elution by using a series of chloroform-acetone solutions with volume ratios of 9:1, 8:2, 7:3, 6:4 and 5:5 in sequence, and collecting eluent obtained when the chloroform-acetone solution is used for elution with a volume ratio of 8:2, wherein the eluent is called as second eluent;
C. high performance liquid chromatography separation: and C, introducing the second eluent finally obtained in the step B into a high performance liquid chromatography for separation and purification, wherein the high performance liquid chromatography is to adopt a Zorba xPrepHT GF chromatographic column with the size of 21.2mm multiplied by 250mm and the size of 5 mu m, the flow rate is 20mL/min, the mobile phase is 53 wt% methanol aqueous solution, the detection wavelength of an ultraviolet detector is 338nm, the sample injection of the third eluent is 200 mu L each time, collecting the eluent corresponding to the chromatographic peak retention time of 18.6min after each sample injection, and obtaining the quinoline alkaloid compound after removing the solvent from the third eluent.
Preferably, in the step A, the concentration of the ethanol is preferably 95 wt%.
Preferably, in the step B, before the extract is roughly separated by silica gel column chromatography, the extract is dissolved by methanol and then mixed with 80-120 mesh silica gel with the weight ratio of 1.5-2.5 times.
Preferably, in the step C, after the separation and purification by the high performance liquid chromatography, the obtained compound is dissolved again by pure methanol, and then the obtained compound is separated and purified by gel column chromatography with the pure methanol as a mobile phase.
The third aspect of the invention provides the application of the quinoline alkaloid compound in the first aspect in preparing a medicament for resisting tobacco mosaic virus.
The structure of the quinoline alkaloid compound prepared by the method is determined by the following method:
the appearance observation shows that: the compounds of the present invention are brown gums;
the ultraviolet-visible absorption spectrum shows that the compound has maximum absorption at 232 nm and 338nm, and the existence of an aromatic ring structure in the compound is proved;
infrared spectrum (potassium bromide tablet) shows that the compound has amino group(3281cm-1) Carbonyl group (1677, 1650 cm)-1) Aromatic rings (1614 and 1455 cm)-1) A characteristic functional group; high resolution mass spectrometry (HRESIMS) gave an excimer ion peak 266.1150[ M + Na ]]+Determining the formula of the compound as C15H17NO2The unsaturation degree is 8. Bonding of1H and13NMR data on C and HSQC show that the compound comprises a 1,2,4, 5-tetra-substituted benzene ring (C-5 to C-8, C-4a and C-8a, H-5 and H-8), an isopropyl group (C-4' to 6', H-4', and H6-5',6'), an acetyl group (C-1', C-2', and H)3-2'), one-NH-CO-CH-C-group (C-2. about.4, H-1, H-3 and NH). In order to satisfy the 8 unsaturations of the compound, two carbonyl groups, one double bond, a benzene ring and the-NH-CO-CH-C-group should form 1 quinolin-2(1H) -one 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 isopropyl substitution at the C-7 position was determined by correlating H-4' with C-6, C-7, C-8, H6-5',6' with HMBC at C-7. Finally, according to H3The 3 'is related to HMBC at C-5, C-6, C-7, and the substitution of methyl (C-1') at C-6 can be determined. Thus far, the structure of the compound of the present invention was confirmed and identified as 4-acetyl-7-isopropyl-6-methylquinolin-2(1H) -one.
TABLE-1 preparation of the compounds1HNMR and13c NMR data (CDCl)3)
The invention has the following beneficial effects:
1. the invention separates a new compound from tobacco stems for the first time, determines the quinoline alkaloid compound by a nuclear magnetic resonance and mass spectrometry method, and characterizes the specific structure of the quinoline alkaloid compound. And the quinoline alkaloid compound has good activity of resisting tobacco mosaic virus: experiments for resisting tobacco mosaic virus show that the relative inhibition rate of the quinoline alkaloid compound reaches 38.5%, and the activity of the quinoline alkaloid compound is higher than that of a control ningnanmycin (33.0%). The results show that the compound has good application prospect in the preparation of the anti-tobacco mosaic virus medicine. The compound has simple structure and good activity, and can be used as a guiding compound of a tobacco mosaic virus resistant medicament.
2. Because the biological yield of tobacco roots and stems is huge, the tobacco roots and stems are generally discarded as wastes in the production process of tobacco leaves, and the compound raw materials are easy to obtain; the extraction method of the compound is simple, the compound is easy to separate and obtain, and the industrial preparation is easy to realize.
3. The compound of the invention has simple molecular structure, is easy to realize artificial synthesis, and can realize subsequent industrialization by artificial synthesis.
4. The preparation method combining conventional column chromatography and high performance liquid chromatography is adopted, the preparation operation flow of the compound is simple, the purity of the obtained compound is high, and the quality and purity of the compound in subsequent industrial production can be guaranteed.
5. The compound is safe and nontoxic, shows good activity of resisting tobacco mosaic virus, and can provide an ideal new skeleton type drug source molecule for preventing and treating tobacco mosaic disease.
Drawings
FIG. 1 is the nuclear magnetic resonance carbon spectrum of the quinoline alkaloid compound.
FIG. 2 is the nuclear magnetic resonance hydrogen spectrum of the quinoline alkaloid compound.
Fig. 3 is the major HMBC correlation of the quinoline alkaloid compounds.
Detailed Description
The present invention is further illustrated by the following examples, but is not limited to these examples. The experimental methods not specified in the examples are generally commercially available according to the conventional conditions and the conditions described in the manual, or according to the general-purpose equipment, materials, reagents and the like used under the conditions recommended by the manufacturer, unless otherwise specified. The starting materials required in the following examples are all commercially available.
Quinoline alkaloid compound C of the invention15H17NO2The preparation method comprises the steps of extract extraction, silica gel column chromatography and high-pressure liquid chromatography separation, and specifically comprises the following steps:
A. extracting the extractum: taking the stems of air-dried Yunyan-116 as a raw material, crushing the dried Yunyan-116 into 20-40 meshes, carrying out ultrasonic extraction on the crushed Yunyan-116 meshes by using 90-99% ethanol, adding an extracting solution into a mixed solution of ethyl acetate and 3% tartaric acid, standing the mixed solution for layering, and then using Na2CO3Adjusting pH of water layer to 9.0, extracting with ethyl acetate, filtering, and concentrating under reduced pressure to obtain extract;
B. silica gel column chromatography: filling the extract into a column by using a 200-300-mesh silica gel dry method, and performing silica gel column chromatography; gradient eluting with chloroform-methanol solution at volume ratio of 10:0, 9:1, 8:2, 7:3, 6:4, and 5:5 respectively, mixing the parts with the same polarity, collecting eluate of each part, and concentrating; wherein the mass ratio of the silica gel to the extract is 2-5. Eluting the concentrated part of the chloroform-methanol 9:1 eluent by chloroform-acetone solutions with the volume ratio of 9:1, 8:2, 7:3, 6:4 and 5:5 respectively, collecting the 8:2 part of the eluent, concentrating, and separating and purifying by high performance liquid chromatography.
C. The high performance liquid chromatography is to adopt a ZorbaxPrepHT GF chromatographic column with the flow rate of 20mL/min and the mobile phase of 53% methanol water solution, the high performance liquid chromatography is to adopt a ZorbaxPrepHT GF chromatographic column with the flow rate of 5 mu m, the detection wavelength of an ultraviolet detector is 338nm, 200 mu L of sample introduction is carried out each time, chromatographic peaks of 18.6min are collected, and the crude compound is obtained by evaporation after multiple accumulation.
D. And C, after the high performance liquid chromatography is used for separation and purification in the step C, dissolving the obtained crude compound with pure methanol again, and then using methanol as a mobile phase for gel column chromatography separation for further separation and purification to obtain the quinoline alkaloid compound.
The 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 tobacco stem samples from Yunnan:
example 1
The tobacco root and stem sample is from Yuxi Yunan, and the variety is Yunyan-116. Sampling tobacco stem, pulverizing 2.0kg into 30 mesh, extracting with 95% ethanol under ultrasonic for 3 times (30 min each time), mixing extractive solutions, adding into mixture of ethyl acetate and 3% tartaric acid (ethyl acetate: tartaric acid: 97:3, by mass ratio), standing for layering, and adding Na2CO3Adjusting pH of water layer to 9.0, extracting with ethyl acetate, filtering, and concentrating under reduced pressure to obtain extract 98.2 g. Dissolving the extract with pure methanol, mixing with 150g of 100 mesh crude silica gel, loading 1.0kg of 200 mesh silica gel into a column, performing silica gel column chromatography, performing gradient elution with chloroform-methanol at volume ratio of 10:0, 9:1, 8:2, 7:3, 6:4, and 5:5, monitoring by TLC, combining the same parts to obtain 6 parts, concentrating the chloroform-methanol elution part at volume ratio of 9:1, eluting with chloroform-acetone solution at volume ratio of 9:1, 8:2, 7:3, 6:4, and 5:5, respectively, collecting 8:2 parts of the eluate, eluting with petroleum ether-acetone solution, preparing high performance liquid chromatography with Agilent 1100, taking 53% methanol as mobile phase, preparing column with ZorbaxPrep pHT column (21.2 × 250mm,5 μm) at flow rate of 20mL/min, detecting wavelength of ultraviolet detector of 338nm, sampling 200 μ L each time, collecting chromatographic peak of 18.6min, accumulating for multiple times, and evaporating to obtain crude compound; dissolving the obtained crude 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 the pure product of the new compound.
Example 2
The tobacco root and stem sample is from Yunan Dali and is Yunyan-116. Sampling tobacco stem 3.5kg, pulverizing to 20 mesh, ultrasonic extracting with 99% ethanol for 3 times (30 min each time), mixing extractive solutions, adding into mixed solution of ethyl acetate and 3% tartaric acid, standing for layering, and adding Na2CO3Adjusting pH of water layer to 9.0, extracting with ethyl acetate, filtering, and concentrating under reduced pressureMaking into extract to obtain 178g of extract. Dissolving the extract with pure methanol, mixing with 350g of 80 mesh crude silica gel, loading 1.5kg of 250 mesh silica gel into a column, performing silica gel column chromatography, performing gradient elution with chloroform-methanol at volume ratio of 10:0, 9:1, 8:2, 7:3, 6:4 and 5:5, and combining the same parts by TLC monitoring to obtain 6 parts. Performing silica gel column chromatography again on the concentrated part of the chloroform-methanol 9:1 eluent, eluting with chloroform-acetone solutions with volume ratios of 9:1, 8:2, 7:3, 6:4 and 5:5 respectively, collecting 8:2 part of the eluent, concentrating, and preparing for high performance liquid chromatography. Performing liquid chromatography preparation, performing semi-preparative high performance liquid chromatography separation by using agilent 1100, taking 53% methanol as a mobile phase, taking a Zorba xPrepHT GF column (21.2 x 250mm,5 mu m) preparation column as a stationary phase, performing flow rate of 20mL/min, detecting wavelength of 338nm by using an ultraviolet detector, performing sample injection of 200L each time, collecting chromatographic peaks for 18.6min, and performing multiple accumulation and evaporation to obtain a crude compound product; dissolving the obtained crude 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 the pure product of the new compound.
Example 3
The tobacco rhizome sample is derived from Yunnan Trijing, and the variety is Yunyan-116. Sampling tobacco stem 5.5kg, pulverizing to 40 mesh, ultrasonic extracting with 99% ethanol for 3 times (30 min each time), mixing extractive solutions, adding into mixed solution of ethyl acetate and 3% tartaric acid, standing for layering, and adding Na2CO3Adjusting pH of the water layer to 9.0, extracting with ethyl acetate, filtering, and concentrating under reduced pressure to obtain extract 245 g. Dissolving the extract with pure methanol, mixing with 615g of 120 mesh crude silica gel, loading 1.8kg of 300 mesh silica gel into a column, performing silica gel column chromatography, performing gradient elution with chloroform-methanol at volume ratio of 10:0, 9:1, 8:2, 7:3, 6:4 and 5:5, and combining the same parts by TLC monitoring to obtain 6 parts. Performing silica gel column chromatography again on the concentrated part of the chloroform-methanol 9:1 eluent, eluting with chloroform-acetone solutions with volume ratios of 9:1, 8:2, 7:3, 6:4 and 5:5 respectively, collecting 8:2 part of the eluent, concentrating, and preparing for high performance liquid chromatography. The method comprises performing semi-preparative high performance liquid chromatography separation by using agilawood 1100 in liquid chromatography, using 53 wt% methanol as mobile phase, and ZorbaxprAn epHT GF column (21.2 x 250mm,5 mu m) preparation column is a stationary phase, the flow rate is 20mL/min, the detection wavelength of an ultraviolet detector is 338nm, 200L of sample is injected each time, a chromatographic peak of 18.6min is collected, and a crude compound product can be obtained by evaporation after multiple accumulation; dissolving the obtained crude 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 the new compound.
Example 4
The compound prepared in example 1 was taken as a brown gum.
The determination method comprises the following steps: nuclear magnetic resonance, in combination with other spectroscopic techniques, was used to identify structures.
1) Ultraviolet spectrum (solvent is methanol), lambda max (log epsilon) 210(4.18), 232(3.56) and 338(3.20) nm;
2) infrared spectroscopy (Potassium bromide compression) v max 3281, 2924, 1677, 1650, 1614, 1455, 1226, 1150, 859, 740cm-1；
3) High resolution mass spectrometry (HRESIMS) gave an excimer ion peak 266.1150[ M + Na ]]+(calculated 266.1157). Bonding of1H and13the C NMR spectrum gives a molecular formula C15H17NO2The unsaturation degree is 8.
From1H and13the CNMR spectrum (data attribution see table-1) signals can be seen: the compounds are shown to include a 1,2,4, 5-tetrasubstituted benzene ring (C-5 to C-8, C-4a and C-8a, H-5 and H-8), an isopropyl group (C-4 'to 6', H-4', and H6-5',6'), an acetyl group (C-1', C-2', and H3-2'), and an-NH-CO-CH-C-group (C-2 to 4, H-1, H-3 and NH). In order to satisfy the 8 unsaturations of the compounds, two carbonyl groups, one double bond, a benzene ring and the-NH-CO-CH-C-group should form quinolin-2(1H) -one. 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 isopropyl substitution at the C-7 position was determined by correlating H-4' with C-6, C-7, C-8, H6-5',6' with HMBC at C-7. Finally, according to H3-3 'is related to HMBC at C-5, C-6, C-7, and the substitution of methyl (C-1') at C-6 can be determined. Thus far, the structure of the compound of the present invention was confirmed and identified as 4-acetyl-7-isopropyl-6-methylquinolin-2(1H) -one.
Example 5
The compound prepared in example 2 was taken as a brown gum. The assay method was the same as in example 4, and it was confirmed that the compound prepared in example 2 was 4-acetyl-7-isopropyl-6-methylquinolin-2(1H) -one, which is the quinoline alkaloid compound.
Example 6
The compound prepared in example 3 was taken as a brown gum. The assay method was the same as in example 4, and it was confirmed that the compound prepared in example 3 was 4-acetyl-7-isopropyl-6-methylquinolin-2(1H) -one, which is the quinoline alkaloid compound.
Example 7
Any quinoline alkaloid compound prepared in the examples 1-3 is used for carrying out an activity test on tobacco mosaic virus, and the test conditions are as follows:
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 20M. Selecting leaves suitable for testing (normal leaves, no disease and no insect) from 5-6 flue-cured tobacco plants, uniformly spraying fine carborundum on the leaves, and writing the tobacco mosaic virus source (3.0 multiplied by 10) for standby use with a writing brush-3) Uniformly smearing on blades scattered with carborundum, immediately placing in a culture dish filled with liquid medicine for processing for 20min after all selected blades are disinfected, taking out, sprinkling water drops and confining liquid on the blades, recovering and arranging two half blades, covering glass in an enamel officer paved with toilet paper for moisturizing, controlling the temperature to be (23 +/-2) DEG C, placing in a greenhouse for natural light irradiation, and enabling the officer to see withered spots after 2-3 d.
XI％＝(CK-T)/CK×100％
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.
The result shows that the relative inhibition rate of the compound is 38.5 percent and is 33.0 percent higher than that of the control ningnanmycin, which indicates that the compound has good activity against tobacco mosaic virus.
Claims (6)
1. A quinoline alkaloid compound is characterized in that the molecular formula of the compound is as follows: c15H17NO2Which has the following structure:
2. the method for producing a quinoline alkaloid compound according to claim 1, comprising the steps of:
A. extracting the extractum: taking tobacco stems as raw materials, crushing, carrying out ultrasonic extraction by using 90-99 wt% ethanol, adding an extracting solution into a mixed solution of ethyl acetate and 3 wt% tartaric acid, standing and layering the mixed solution, and then using Na2CO3Adjusting pH of water layer to 9.0, extracting with ethyl acetate, filtering, and concentrating under reduced pressure to obtain extract;
B. silica gel column chromatography: b, filling the extract obtained in the step A into a column by using a 200-300-mesh silica gel dry method, and performing silica gel column chromatography; gradient eluting with chloroform-methanol solution at volume ratio of 10:0, 9:1, 8:2, 7:3, 6:4, and 5:5 respectively, mixing the parts with the same polarity, collecting eluate of each part, and concentrating; wherein the mass ratio of the silica gel to the extract is 2-5; collecting eluate obtained by eluting with chloroform-methanol solution at volume ratio of 9:1, and making into first eluate; continuously separating the first eluent by using a silica gel chromatographic column, performing gradient elution by using a series of chloroform-acetone solutions with volume ratios of 9:1, 8:2, 7:3, 6:4 and 5:5 in sequence, and collecting eluent obtained when the chloroform-acetone solution is used for elution with a volume ratio of 8:2, wherein the eluent is called as second eluent;
C. high performance liquid chromatography separation: and C, introducing the second eluent finally obtained in the step B into a high performance liquid chromatography for separation and purification, wherein the high performance liquid chromatography is to adopt a Zorba xPrepHT GF chromatographic column with the size of 21.2mm multiplied by 250mm and the size of 5 mu m, the flow rate is 20mL/min, the mobile phase is 53 wt% methanol aqueous solution, the detection wavelength of an ultraviolet detector is 338nm, the sample injection of the third eluent is 200 mu L each time, collecting the eluent corresponding to the chromatographic peak retention time of 18.6min after each sample injection, and obtaining the quinoline alkaloid compound after removing the solvent from the third eluent.
3. The method for producing a quinoline alkaloid compound according to claim 2, wherein the concentration of ethanol in step a is preferably 95 wt%.
4. The method for preparing quinoline alkaloids compounds according to claim 2, wherein in step B, the extract is dissolved in methanol before being roughly separated by silica gel column chromatography, and then is mixed with 80-120 mesh silica gel with a weight ratio of 1.5-2.5 times.
5. The method of claim 2, wherein in the step C, after the separation and purification by high performance liquid chromatography, the obtained compound is dissolved again in pure methanol, and the obtained solution is further separated and purified by gel column chromatography using pure methanol as a mobile phase.
6. The use of quinoline alkaloid compounds according to claim 1 for the preparation of a medicament against tobacco mosaic virus.
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| CN113717184A (en) * | 2021-08-19 | 2021-11-30 | 云南省烟草农业科学研究院 | Quinoline alkaloid with tobacco mosaic virus resisting activity in cigar, and preparation method and application thereof |
| CN114456102A (en) * | 2022-01-27 | 2022-05-10 | 云南中烟工业有限责任公司 | Indole alkaloid compound and preparation method and application thereof |
| CN115124505A (en) * | 2022-08-01 | 2022-09-30 | 云南中烟工业有限责任公司 | Indole alkaloid compound and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113717184A (en) * | 2021-08-19 | 2021-11-30 | 云南省烟草农业科学研究院 | Quinoline alkaloid with tobacco mosaic virus resisting activity in cigar, and preparation method and application thereof |
| CN113717184B (en) * | 2021-08-19 | 2023-04-11 | 云南省烟草农业科学研究院 | Quinoline alkaloid with tobacco mosaic virus resisting activity in cigar and preparation method and application thereof |
| CN114456102A (en) * | 2022-01-27 | 2022-05-10 | 云南中烟工业有限责任公司 | Indole alkaloid compound and preparation method and application thereof |
| CN115124505A (en) * | 2022-08-01 | 2022-09-30 | 云南中烟工业有限责任公司 | Indole alkaloid compound and preparation method and application thereof |
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