CN115433185A - Monoterpene indole alkaloid, and preparation method and application thereof - Google Patents
Monoterpene indole alkaloid, and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a monoterpene indole alkaloid and a preparation method and application thereof, belongs to the technical field of extraction and identification of active ingredients of traditional Chinese medicines, and discovers that the monoterpene indole alkaloid is a main effective ingredient and obtains an effective part of the monoterpene indole alkaloid by researching the foundation of antituberculous active substances of lung-regulating powder; alkaloid components are separated from the lung-regulating powder, 2 new alkaloid compounds are separated from the effective parts, and the remarkable anti-mycobacterium smegmatis activity is shown, so that a basis is provided for further development and utilization of the lung-regulating powder.
Description
Technical Field
The invention relates to the technical field of extraction and identification of active ingredients of traditional Chinese medicines, in particular to monoterpene indole alkaloid and a preparation method and application thereof.
Background
Tuberculosis (TB) is a chronic infectious disease caused by infection with Mycobacterium Tuberculosis (m.tb), and is the first killer of death in recent years worldwide due to infection with a single pathogenic microorganism. After the infection, M.tb invades various organs of patients, particularly the lung (pulmonary tuberculosis), has the characteristics of difficult control of infection source, strong infectivity, high death rate and the like, and becomes a global important public health problem. In clinic, preventive vaccines and chemical drugs are the main means for preventing and controlling TB, however, with the appearance and spread of drug-resistant tuberculosis in the world in recent years, especially the generation and spread of multi-drug resistant tuberculosis, wide drug-resistant tuberculosis and HIV double infection, greater challenges are provided for preventing and controlling TB. The main body is as follows: first, the number of drug-resistant patients increases year by year, while the current first-line clinical drugs are old drugs many years ago, and the research and development of new drugs are slow. Secondly, most of the existing combined medication schemes have the defects of long treatment period, poor tolerance, great side effect and the like, the living quality of patients is seriously reduced, the further deterioration of drug resistance is possibly promoted, and the difficulty of clinical medication cannot be fundamentally solved. Thirdly, the existing TB prophylactic vaccines, which only have a good preventive effect against children, have poor protective effects against adolescents and adults, and their immune protective abilities will be continuously weakened or even disappear as the vaccination time is prolonged. Therefore, in order to face the serious challenge of the existing clinical drugs for treating TB, the novel antitubercular drugs which are high in efficiency, low in toxicity and free of drug resistance are developed to fundamentally solve the problem of difficult clinical medication, are an urgent subject for preventing and treating TB at present, and have important clinical significance.
Lifei powder, also called bone setting pill, lianghou tea, etc., using whole plant of climbing ear herb (climbing stem ear herb) Hedyotis scandens Roxb, which belongs to the genus Saxifraga of Rubiaceae, is a common medicine and food dual-purpose Chinese medicine used in white, dai, naxi, lisu, onde, hanni, etc. According to records in the Chinese materia medica, the Chinese materia medica has cool and bitter taste, enters lung and kidney channels, has the effects of clearing away heat and toxic material, regulating lung and relieving cough, reuniting bones and tendons and the like, and is mainly used for treating clinical diseases such as phthisis, pneumonia, bronchitis, sore throat, fracture and the like. The traditional Chinese medicine is usually used for treating infectious diseases by single medicine, for example, 30g of lung regulating powder is recorded in Yunnan Chinese herbal medicine, meat stewing is taken, and pulmonary tuberculosis is treated, and field examination shows that the prescription is taken as a special prescription for treating pulmonary tuberculosis until now in Yunnan anger river, and then the traditional Chinese medicine is taken as 30g of lung regulating powder, and is decocted with water to treat pneumonia, bronchitis and stomatitis. Analysis by combining the traditional efficacy and modern medical view shows that the lung-regulating powder contains potential antibacterial active ingredients, particularly active ingredients against mycobacterium tuberculosis. Therefore, the lung-regulating powder is a medicine-food dual-purpose traditional Chinese medicine with a characteristic curative effect for treating the pulmonary tuberculosis in China, has a long medicinal history, and has important research value and development and utilization prospects.
Paper diffusion research by Prakash Basnet and the like shows that the lung regulating powder extract has obvious inhibition effect on ordinary proteus, klebsiella pneumoniae and staphylococcus aureus. Therefore, the lung-regulating powder has obvious antibacterial activity, especially activity against mycobacterium tuberculosis, and has high consistency with the effects of clearing heat and removing toxicity, regulating lung and relieving cough in the traditional medicine of the lung-regulating powder, and mainly treating phthisis, pneumonia and bronchitis. In addition, the lung-regulating powder extract also has the biological activities of antivirus, antioxidation and the like. Few reports exist at present about the research on the chemical components of lung-regulating powder, and only three documents report that 28 compounds are separated and identified from ethanol extracts of the lung-regulating powder, including 6 flavonoids, 6 triterpenes, 1 steroid and 15 phenolic acids. In addition, he Kequn et al preliminarily measured the alkaloid components that may be contained therein by ultraviolet spectrophotometry, however, there is no report on the separation of alkaloids from lung regulating powder.
Therefore, the research on the chemical components of the powder for regulating lung is superficial and not deep enough all the time, and particularly, the existing chemical component research cannot support the drug effect material basis of the powder for treating the pulmonary tuberculosis with exact curative effect, which causes great limitation to the full development and utilization of the powder for regulating lung.
Disclosure of Invention
In view of the above, an object of the present invention is to provide a monoterpene indole alkaloid; the second purpose of the invention is to provide a preparation method of the monoterpene indole alkaloid; the invention also aims to provide the application of the monoterpene indole alkaloid in the preparation of the anti-mycobacterium smegmatis medicine; the fourth purpose of the invention is to provide the application of the monoterpene indole alkaloid in the preparation of anti-mycobacterium tuberculosis drugs; the fifth purpose of the invention is to provide an application of the monoterpene indole alkaloid in preparation of a medicine for treating tuberculosis.
In order to achieve the purpose, the invention provides the following technical scheme:
1. a monoterpene indole alkaloid has a structural formula shown in formula 1 or 2:
preferably, the monoterpene indole alkaloid is separated from traditional Chinese medicine lung-regulating powder.
2. A preparation method of the monoterpene indole alkaloid comprises the following extraction steps:
a. dispersing the lung regulating powder ethanol crude extract with water, and sequentially extracting with petroleum ether, dichloromethane and n-butanol to obtain corresponding extracts;
b. subjecting the dichloromethane extract to silica gel column chromatography eluting with a gradient of petroleum ether- ethyl acetate 15, 0, 10, 8:1, 7:1, 5:1, 4:1, 2:1, 1:1, 1:3, 1:5, 0:1, each gradient eluting 4 column volumes; combining petroleum ether-ethyl acetate gradient elution components to obtain 13 components, wherein the 7 th component is mainly obtained by gradient elution and combination of 7:1-4:1;
c. subjecting the eluted 7 th fraction to MCI column chromatography, eluting with methanol-water in 40%, 50%, 60%, 70%, 80%, 90%, 100% methanol gradients of 4 column volumes per gradient to give a total of 23 eluted fractions;
d. aiming at the 17 th component, the 17 th component is mainly obtained by gradient elution and combination of 60 percent to 70 percent, RP-HPLC separation is adopted, 68 percent methanol isocratic elution is adopted, and the monoterpene indole alkaloid shown in the formula (1) is obtained;
e. aiming at the 21 st component, the monoterpene indole alkaloid shown in the formula (2) is obtained by mainly carrying out gradient elution and combination on 70% -80%, and carrying out RP-HPLC separation and isocratic elution on 75% methanol.
3. An application of the monoterpene indole alkaloid in preparing anti-mycobacterium smegmatis medicine is disclosed.
4. An application of the monoterpene indole alkaloid in the preparation of anti-mycobacterium tuberculosis drugs.
5. An application of the monoterpene indole alkaloid in preparing medicine for treating tuberculosis is provided.
The invention has the beneficial effects that:
the foundation of antituberculous active substances of the lung-regulating powder is researched for the first time, and the monoterpene indole alkaloid is found to be the main effective component and the effective part is obtained;
alkaloid components are separated from the lung regulating powder for the first time, and 2 new alkaloid compounds are separated from the effective parts and show obvious activity of resisting mycobacterium smegmatis.
The preparation method obtains the antituberculous drug effect active site of the lung-regulating powder, and defines the main chemical components of the antituberculous drug effect active site, thereby providing a basis for further development and utilization of the lung-regulating powder.
Drawings
In order to make the object, technical scheme and beneficial effect of the invention more clear, the invention provides the following drawings for explanation:
FIG. 1 shows the anti-Mycobacterium smegmatis activity of four ethnic groups of Chinese medicinal materials;
wherein A is the total ethanol extract of four ethnic groups of traditional Chinese medicines (500 mg/mL): 1DMSO, 2 ethanol, 3 Lifei san, 4 rock cowpea, 5 Japanese ardisia herb and 6 wild buckwheat rhizome; b, comparison products: 1H2O, 2DMSO, 3 kanamycin (500. Mu.g/mL), 4 streptomycin (200. Mu.g/mL), 5 isoniazid (1 mg/mL), 6 rifamycin (2 mg/mL);
FIG. 2 shows the anti-M.smegmatis activity of the extracted part of the Lifeishan extract;
wherein A, B, C is petroleum ether phase, dichloromethane phase and n-butanol phase respectively; 1 is solvent DMSO,2-6 are respectively corresponding extracts with different concentrations, and the concentrations are 250, 100, 50, 10 and 1mg/mL in sequence;
FIG. 3 shows the activity of the extracted parts of the lung regulating powder extract against BCG and Mycobacterium tuberculosis H37 Ra;
wherein, A is anti-BCG activity: 1.2, 3, sequentially comparing petroleum ether, dichloromethane and n-butanol, 4, 5 and 6 sequentially extracting parts of petroleum ether, dichloromethane and n-butanol, wherein the concentration is 250mg/mL; B. c respectively shows the activities of the extraction parts of dichloromethane and n-butanol for resisting mycobacterium tuberculosis H37Ra, and the concentrations are both 250mg/mL;
FIG. 4 is HPLC analysis chromatogram of active alkaloid part (HPLC elution conditions are methanol-5 ‰ formic acid water system: 0-35-40min,45-90-100% methanol, 254nm wavelength);
FIG. 5 shows the activity of the active alkaloid site against Mycobacterium smegmatis;
wherein, A is a comparison: 1H2O, 2DMSO, 3 kanamycin (500. Mu.g/mL), 4 streptomycin (200. Mu.g/mL), 5 rifamycin (2 mg/mL), 6 isoniazid (1 mg/mL); b is elution site (50 mg/mL);
FIG. 6 is a UPLC-HRMS analysis ion flow graph of active alkaloid fractions;
FIG. 7 is the structural formula of Compound 1;
FIG. 8 is the structural formula of Compound 2.
Detailed Description
The present invention is further described with reference to the following drawings and specific examples so that those skilled in the art can better understand the present invention and can practice the present invention, but the examples are not intended to limit the present invention.
Example 1 preparation of anti-tubercular powder
Four traditional Chinese medicines with anti-tuberculosis efficacy and drug history are selected at the initial stage, namely lung regulating powder, wild buckwheat rhizome, japanese ardisia herb and cowpea respectively, and a paper diffusion method is utilized to perform activity screening on an ethanol total extract (obtained by extracting 95% ethanol in a volume three times and concentrating at 50 ℃) and a water total extract (obtained by extracting deionized water in a volume three times and concentrating at 50 ℃) respectively by taking mycobacterium smegmatis as an anti-tuberculosis activity screening model, and experimental results show that the lung regulating powder ethanol total extract has a remarkable inhibition zone (figure 1) and shows exact anti-mycobacterium smegmatis activity.
Firstly, dispersing the lung regulating powder ethanol total extract in water, and sequentially extracting with petroleum ether, dichloromethane and n-butanol to obtain corresponding parts, wherein activity tests show that the dichloromethane part has the best activity for resisting mycobacterium smegmatis (figure 2), and the dichloromethane part is obviously improved compared with total extracts and shows obvious correlation with concentration, and shows that active ingredients are mainly concentrated in the dichloromethane part. Secondly, BCG (bovine mycobacterium tuberculosis attenuated strain) and a mycobacterium tuberculosis H37Ra strain are used as anti-tuberculosis activity screening models, the activity of the extraction part is further tested (figure 3), an experimental conclusion consistent with the mycobacterium smegmatis model is obtained, and the significant anti-tuberculosis active components in the dichloromethane extraction part of the lung regulating powder are further verified.
EXAMPLE 2 purification of alkaloid antitubercular active ingredients in powder for treating Lung diseases
Aiming at dichloromethane parts, the active ingredients are identified and refined by a strategy of combining activity tracing and UPLC-HRMS identification. Subjecting the dichloromethane extract to silica gel column chromatography eluting with a gradient of petroleum ether- ethyl acetate 15, 0, 10, 8:1, 7:1, 5:1, 4:1, 2:1, 1:1, 1:3, 1:5, 0:1, each gradient eluting 4 column volumes; the petroleum ether-ethyl acetate gradient elution components are combined to obtain 13 components in total. Activity analysis shows that the 7 th component (mainly obtained by gradient elution and combination of 7:1-4:1, and an HPLC chromatogram is shown in figure 4) has the most remarkable activity for resisting mycobacterium smegmatis (figure 5); further, it was found by UPLC-MS analysis that the elution site was mainly a alkaloid compound, from which 19 alkaloid chromatographic peaks were preliminarily identified (fig. 6, table 1). The effective part of the mycobacterium smegmatis can be obtained by refining the above method, and is also called as an active alkaloid part.
TABLE 1 alkaloids presumed in 7:1-4:1 elution sites for petroleum ether-ethyl acetate
Note: * For isolating the novel compounds
Example 3 isolation and characterization of the alkaloid Components in the effective fractions
Isolation preparation of compounds 1 and 2: firstly, the active alkaloid part is roughly separated by MCI column chromatography, the solvent is methanol-water, the elution procedure is 40%, 50%, 60%, 70%, 80%, 90% and 100% methanol, each concentration elutes 4 column volumes, and 23 components containing the compound are obtained by combination. For the 17 th fraction (mainly obtained by combining 60% -70% gradient elution), RP-HPLC preparation (68% methanol isocratic elution) was used to obtain compound 1; for the 21 st fraction (mainly from 60% to 80% gradient elution pooled), RP-HPLC preparation (75% methanol isocratic elution) was used to obtain compound 2.
2 alkaloid monomeric compounds are separated and identified from the extract, and are all new compounds.
Structural characterization of compounds 1 and 2: the compounds 1 and 2 are identified to be monoterpene indole alkaloids through the technologies such as nuclear magnetic resonance, high resolution mass spectrum and the like, are alkaloid compounds discovered from lung-regulating powder for the first time, and are new compounds. The specific structure of compound 1 is shown in FIG. 7, NMR data is shown in Table 2, and the molecular formula is C 21 H 25 N 2 (ii) a The specific structure of Compound 2 is shown in FIG. 8, NMR data is shown in Table 3, and the molecular formula is C 31 H 38 N 2 O 2 。
TABLE 2 NMR data for Compound 1
| No. | δ H (mult,J in Hz) | |
| 2 | 134.4 | |
| 3 | 138.4 | |
| 5 | 8.16(br s) | 132.7 |
| 6 | 8.04(overlap) | 115.5 |
| 7 | 132.9 | |
| 8 | 119.5 | |
| 9 | 8.06(overlap) | 122.5 |
| 10 | 7.31(t,8.4) | 121.6 |
| 11 | 7.61(t,8.4) | 131.6 |
| 12 | 7.83(d,8.4) | 114.2 |
| 13 | 145.0 | |
| 14 | 3.96(s) | 44.5 |
| 1’ | 5.84(s) | 111.5 |
| 2’ | 154.9 | |
| 3’ | 2.41(m) | 39.0 |
| 4’ | 2.30(m) | 25.8 |
| 5’ | 5.12(t,6.9) | 123.3 |
| 6’ | 132.8 | |
| 7’ | 1.51(s) | 19.3 |
| 8’ | 1.71(s) | 25.8 |
| 9’ | 1.65(s) | 17.8 |
| NH | 13.3(s) |
TABLE 3 NMR data for Compound 2
Example 4 Activity assay of novel Compounds
In the Mycobacterium smegmatis model, the compounds 1 and 2 both show obvious inhibitory activity, and MICs are respectively 62.5 mug/mL and 1.25 mug/mL; in the M.tuberculosis H37Ra model, the MICs of the compounds 1 and 2 are 63.7 mu g/mL and 3.78 mu g/mL respectively.
The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.
Claims (6)
1. A monoterpene indole alkaloid is characterized in that the structural formula is shown as formula 1 or 2:
2. the monoterpene indole alkaloid of claim 1, wherein the monoterpene indole alkaloid is isolated from traditional Chinese medicine lung regulating powder.
3. A process for the preparation of a monoterpene indole alkaloid according to claim 1, comprising the following extraction steps:
a. dispersing the lung regulating powder ethanol crude extract with water, and sequentially extracting with petroleum ether, dichloromethane and n-butanol to obtain corresponding extracts;
b. subjecting the dichloromethane extract to silica gel column chromatography eluting with a gradient of petroleum ether-ethyl acetate 15, 0, 10, 8:1, 7:1, 5:1, 4:1, 2:1, 1:1, 1:3, 1:5, 0:1, each gradient eluting 4 column volumes; combining petroleum ether-ethyl acetate gradient elution components to obtain 13 components, wherein the 7 th component is mainly obtained by gradient elution and combination of 7:1-4:1;
c. subjecting the eluted 7 th fraction to MCI column chromatography, eluting with methanol-water in 40%, 50%, 60%, 70%, 80%, 90%, 100% methanol gradients of 4 column volumes per gradient to give a total of 23 eluted fractions;
d. aiming at the 17 th component, the 17 th component is mainly obtained by gradient elution and combination of 60 percent to 70 percent, RP-HPLC separation is adopted, 68 percent methanol isocratic elution is adopted, and the monoterpene indole alkaloid shown in the formula (1) is obtained;
e. aiming at the 21 st component, the monoterpene indole alkaloids shown in the formula (2) are obtained by mainly carrying out gradient elution and combination on 70% -80%, and carrying out RP-HPLC separation and isocratic elution with 75% methanol.
4. Use of a monoterpene indole alkaloid according to claim 1 in the preparation of a medicament against mycobacterium smegmatis.
5. Use of the monoterpene indole alkaloid of claim 1 in the preparation of an anti-mycobacterium tuberculosis medicament.
6. The use of the monoterpene indole alkaloid according to claim 1 in the preparation of a medicament for the treatment of tuberculosis.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102225937A (en) * | 2011-05-04 | 2011-10-26 | 中国科学院昆明植物研究所 | Antineoplastic alkaloid compound, and its medicine composition, preparation method and application |
| US20190322638A1 (en) * | 2016-11-15 | 2019-10-24 | Ocean University Of China | Dipyridyl alkaloid, preparation method therefor and use thereof |
| CN114957285A (en) * | 2022-07-13 | 2022-08-30 | 昆明医科大学 | Fused ether ring monoterpene indole alkaloid compound, preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102225937A (en) * | 2011-05-04 | 2011-10-26 | 中国科学院昆明植物研究所 | Antineoplastic alkaloid compound, and its medicine composition, preparation method and application |
| US20190322638A1 (en) * | 2016-11-15 | 2019-10-24 | Ocean University Of China | Dipyridyl alkaloid, preparation method therefor and use thereof |
| CN114957285A (en) * | 2022-07-13 | 2022-08-30 | 昆明医科大学 | Fused ether ring monoterpene indole alkaloid compound, preparation method and application |
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