CN109912543B - Pasima A and preparation method thereof - Google Patents
Pasima A and preparation method thereof Download PDFInfo
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- CN109912543B CN109912543B CN201910178715.9A CN201910178715A CN109912543B CN 109912543 B CN109912543 B CN 109912543B CN 201910178715 A CN201910178715 A CN 201910178715A CN 109912543 B CN109912543 B CN 109912543B
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Abstract
The invention relates to a Pasmesalamine A and a preparation method thereof, belonging to the technical field of medicine and phytochemistry, and the separation and acquisition of the Pasmesalamine A specifically comprises the following steps: collecting lower tobacco leaves of aromatic tobacco Yunxiangma No. 1, drying in the shade, crushing, and sieving with a 40-mesh sieve to obtain a raw material; soaking and extracting the raw materials by using a methanol solution, distilling under reduced pressure, and concentrating to obtain an extract; extracting the extract with ethyl acetate, separating with silica gel column chromatography, and purifying with high performance liquid chromatograph to obtain pure compound. The invention firstly separates the aromatic tobacco yunxiang pasteur Ma No. 1 to obtain the pasteur Ma A, the compound has novel structure and a plurality of biological activities, especially has better activity of resisting tobacco mosaic virus, provides important inspiration for further researching aromatic tobacco plants as plant resources of medicines for resisting tobacco mosaic virus, and can be used for researching, developing and preparing medicines for resisting tobacco mosaic virus. The invention has the advantages of easily obtained raw materials, simple preparation method, lower preparation cost and wide application prospect.
Description
Technical Field
The invention belongs to the technical field of medicines and phytochemistry, and particularly relates to a Pasmesalamine A and a preparation method and application thereof.
Background
Aromatic tobacco (Oriental tobacaco) is an annual or limited perennial herbaceous plant of the genus Nicotiana in the family Solanaceae, China is the world with the largest tobacco planting area and total yield, China has plants in the north and south, and the plant resources are rich. The aromatic cigarette has the main functions of flavoring in the formula of the mixed type cigarette, can be prepared into cigarettes and the like for people to drink, and also has medicinal values such as anticancer, anti-tumor, antioxidant, ultraviolet radiation resistance, liver protection and the like.
At present, few documents are available for researching chemical components of aromatic tobacco, and foreign scholars perform in-vitro antibacterial activity research on essential oil extracts of aromatic tobacco leaves, and the results show that the aromatic tobacco leaves have strong antibacterial activity; the domestic scholars separate flavonoid, benzofuran and other compounds from the aromatic tobacco, and the compounds have obvious in vitro cytotoxicity inhibition activity and antiviral activity. Yunxiang Pasima No. 1 (YNOTBS1) is a new variety of aromatic tobacco, mainly distributed in Yunna Baoshan, Lincang, Dehong and other production areas, and the research on the chemical components of the aromatic tobacco is less at present. Therefore, it is necessary to study the chemical composition and biological activity thereof and to obtain a compound having a value for development and utilization therefrom.
Disclosure of Invention
In order to overcome the problems in the background art, the invention provides the Pasmesalamine A and the preparation method thereof, the Pasmesalamine A is separated from the aromatic tobacco Yunnan balsamic No. 1, and the compound has a plurality of biological activities, especially has better activity of resisting tobacco mosaic virus.
In order to realize the purpose, the invention is realized by the following technical scheme:
the Pasteur A provided by the invention is separated from aromatic cigarette Yunxiangma No. 1, and has the following structure:
the compound is named as Pasma A, and its molecular formula is C20H32O3。
The preparation method of the Pasmesalamine concretely comprises the following steps:
1) collecting lower tobacco leaves of aromatic tobacco Yunxiangma No. 1, drying in the shade, crushing, and sieving with a 40-mesh sieve to obtain a raw material;
2) soaking the raw materials obtained in the step 1) in a methanol solution for 10-24h, repeatedly extracting for 3 times, distilling under reduced pressure, and concentrating to obtain an extract;
3) dissolving the extract obtained in the step 2) in distilled water, extracting with ethyl acetate, recovering the solvent, performing silica gel column chromatographic separation on the ethyl acetate part by adopting petroleum ether-acetone solution, performing gradient elution, performing decoloration treatment by using an MCI column, and collecting the extract in a volume ratio of 8: 2 eluting with petroleum ether-acetone solution to obtain an eluent I;
4) and performing gradient elution on the eluent I by using chloroform-acetone solution through silica gel column chromatography, and collecting the eluent I by using a solvent with the volume ratio of 15: 1 eluting with chloroform-acetone solution to obtain eluent II;
5) and (3) performing gradient elution on the eluent II through silica gel column chromatography by using a petroleum ether-acetone solution, and collecting the eluent II by using a solvent with a volume ratio of 8: 2, eluting with petroleum ether-acetone solution to obtain eluent III;
6) purifying the eluent III by a high performance liquid chromatograph to obtain a compound, wherein the mobile phase is a mixture of a mobile phase and a solvent in a volume ratio of 7: 3 CH3OH-H2O。
Preferably, in the step 2), the mass ratio of the raw material to the methanol solution is 1: 10.
preferably, in the step 3), the mass ratio of the extract to the distilled water is 1: 1.
preferably, in the step 3), the mass ratio of the extract solution to the ethyl acetate is 1: 4.
preferably, the column chromatography silica gel is 100-200 meshes.
The application of the Paspalum A in preparing the tobacco mosaic disease resisting medicine is provided.
The invention has the beneficial effects that:
the invention firstly separates the aromatic tobacco yunxiang pasteur Ma No. 1 to obtain the pasteur Ma A, the compound has novel structure and a plurality of biological activities, especially has better activity of resisting tobacco mosaic virus, provides important inspiration for further researching aromatic tobacco plants as plant resources of medicines for resisting tobacco mosaic virus, and can be used for researching, developing and preparing medicines for resisting tobacco mosaic virus.
The invention has the advantages of easily obtained raw materials, simple preparation method, lower preparation cost, increased economic and social benefits of aromatic tobacco and wide application prospect.
Drawings
FIG. 1 shows the structural formula of the element of Pasmesalamine A of the present invention;
FIG. 2 shows HMBC and the corresponding derivatives of the Basmanin A of the present invention1H-1HCOSY diagram;
FIG. 3 is the NMR spectrum of Basmanin A of the present invention: (1H-NMR)；
FIG. 4 is the NMR spectrum of Basmanian A of the invention (C:)13C-NMR)；
FIG. 5 is an HMBC spectrum of the Pasmesalamine A of the present invention;
FIG. 6 is a COSY spectrum of the Pasmesalamine A of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, preferred embodiments of the present invention will be described in detail below to facilitate understanding of the skilled person.
Examples
The sample of this example was collected from the smoke area of Dehong City, Yunnan province.
The preparation of the Pasmesalamine concretely comprises the following steps:
1) 10kg of tobacco leaves at the lower part of the air-dried aromatic cigarette Yunxiangma No. 1 are crushed and sieved by a 40-mesh sieve to be used as a raw material.
2) Soaking the raw materials obtained in the step 1) in 10 times (mass ratio) of analytically pure methanol solution for 10h, repeatedly extracting for 3 times, distilling under reduced pressure until no alcohol smell exists, and concentrating to obtain 830g of extract;
3) mixing the extract obtained in the step 2) according to a mass ratio of 1: 1, dissolving the extract in distilled water, and extracting the extract by using ethyl acetate, wherein the mass ratio of the extract solution to the ethyl acetate is 1: 4, the solvent was recovered until there was no ethyl acetate smell, to obtain 381g of ethyl acetate fraction. Ethyl acetate part by mass ratio of 1: 1 and silica gel (column chromatography silica gel is 100-200 meshes), and the volume ratio is 20: 1-1: 2 (20: 1, 15: 1, 9: 1, 8: 2, 7: 3, 6: 4, 1: 1, 1: 2 in sequence), subjecting the ethyl acetate fraction to silica gel column chromatography, gradient eluting, subjecting to MCI column decolorization, collecting the eluate, and purifying with a column chromatography column containing petroleum ether and acetone in a volume ratio of 8: 2 eluting with petroleum ether-acetone solution to obtain an eluent I;
4) the eluent I is subjected to silica gel column chromatography, and the volume ratio of the eluent I to the silica gel column chromatography is 30: 1-6: 4, and collecting the solution by using a chloroform-acetone solution with a volume ratio of 15: 1 eluting with chloroform-acetone solution to obtain eluent II;
5) and the eluent II is subjected to silica gel column chromatography, and the volume ratio of the eluent II to the eluent II is 20: 1-6: 4, performing gradient elution by using petroleum ether-acetone solution, and collecting the eluate in a volume ratio of 8: 2, eluting with petroleum ether-acetone solution to obtain eluent III;
6) purifying the eluent III by a high performance liquid chromatograph to obtain a compound, wherein the mobile phase is a mixture of a mobile phase and a solvent in a volume ratio of 7: 3 CH3OH-H2O。
1. Structural characterization of Compounds of the invention
The structures of the compounds prepared in examples were measured. The compound of the invention is colorless oily matter with a molecular formula of C20H32O3The spectral data are shown in Table 1. HMBC and according to the compound1H-1HCOSY profile (FIG. 2), HMBC profile (FIG. 5) and COSY profile (FIG. 6), the nomenclature of this compound was determined. The Pasima A is extracted from Pasima A.
TABLE 1 preparation of the compound1H and13c nuclear magnetic resonance data [ CDCl ]3]
2. The compound of the invention has anti-tobacco mosaic virus activity detection test (ELISA):
enzyme-linked immunosorbent assay (ELISA) is a technique in which a known antigen or antibody is adsorbed on the surface of a solid phase carrier, and an enzyme-labeled antigen-antibody reaction is carried out on the surface of the solid phase. Detecting the absorbance values of a sample (the compound of the invention) and a control (ningnanmycin) and calculating the multiplication inhibition rate of the compound on the tobacco mosaic virus; the gradient concentration of the standard substance is 62.5pg/ml, 125pg/ml, 250pg/ml, 500pg/ml and 1000pg/ml, and the OD value of each gradient concentration of the standard substance is 0.1557, 0.2455, 0.3566, 0.6085 and 1.0761 in sequence. The absorbance of the sample, control and water was measured in triplicate, and the average absorbance value (OD value) for the sample was 0.1779, the average absorbance value (OD value) for the control was 0.4529 and the average absorbance value (OD value) for the water was 0.484033, on average.
Relative inhibition% (CK group OD value-T group OD value)/CK group OD value × 100%
CK group is blank group (water); the T group is the experimental group (sample or control).
The calculation shows that the relative proliferation inhibition rate of the compound of the invention to the tobacco mosaic virus is 63.25%, and the relative proliferation inhibition rate of the ningnanmycin to the tobacco mosaic virus is 6.43%.
The novel compound of the Pasteurella A is separated from the aromatic tobacco Yunnan Pasteurella No. 1, has various biological activities, particularly has better activity of resisting tobacco mosaic virus, provides important inspiration for further researching aromatic tobacco plants as plant resources of medicines for resisting the tobacco mosaic virus, and can be used for researching and preparing medicines for resisting the tobacco mosaic virus.
Finally, it is noted that the above-mentioned preferred embodiments illustrate rather than limit the invention, and that, although the invention has been described in detail with reference to the above-mentioned preferred embodiments, it will be understood by those skilled in the art that various changes in form and detail may be made therein without departing from the scope of the invention as defined by the appended claims.
Claims (6)
1. An application of a Pasteurenin in preparing a drug for resisting tobacco mosaic disease is characterized in that: has the following structure:
the compound is named as Pasma A, and its molecular formula is C20H32O3。
2. The method for preparing the element of Barmardin according to claim 1, wherein the element of Barmardin is selected from the group consisting of: the method specifically comprises the following steps:
1) collecting lower tobacco leaves of aromatic tobacco Yunxiangma No. 1, drying in the shade, crushing, and sieving with a 40-mesh sieve to obtain a raw material;
2) soaking the raw materials obtained in the step 1) in a methanol solution for 10-24h, repeatedly extracting for 3 times, distilling under reduced pressure, and concentrating to obtain an extract;
3) dissolving the extract obtained in the step 2) in distilled water, extracting with ethyl acetate, recovering the solvent, performing silica gel column chromatographic separation on the ethyl acetate part by adopting petroleum ether-acetone solution, performing gradient elution, performing decoloration treatment by using an MCI column, and collecting the extract in a volume ratio of 8: 2 eluting with petroleum ether-acetone solution to obtain an eluent I;
4) and performing gradient elution on the eluent I by using chloroform-acetone solution through silica gel column chromatography, and collecting the eluent I by using a solvent with the volume ratio of 15: 1 eluting with chloroform-acetone solution to obtain eluent II;
5) and (3) performing gradient elution on the eluent II through silica gel column chromatography by using a petroleum ether-acetone solution, and collecting the eluent II by using a solvent with a volume ratio of 8: 2, eluting with petroleum ether-acetone solution to obtain eluent III;
6) purifying the eluent III by a high performance liquid chromatograph to obtain a compound, wherein the mobile phase is a mixture of a mobile phase and a solvent in a volume ratio of 7: 3 CH3OH-H2O 。
3. The method for preparing the element of Barmardin according to claim 2, wherein the element of Barmardin is selected from the group consisting of: in the step 2), the mass ratio of the raw materials to the methanol solution is 1: 10.
4. the method for preparing the element of Barmardin according to claim 2, wherein the element of Barmardin is selected from the group consisting of: in the step 3), the mass ratio of the extract to the distilled water is 1: 1.
5. the method for preparing the element of Barmardin according to claim 2, wherein the element of Barmardin is selected from the group consisting of: in the step 3), the mass ratio of the extract solution to the ethyl acetate is 1: 4.
6. the method for preparing the element of Barmardin according to claim 2, wherein the element of Barmardin is selected from the group consisting of: the column chromatography silica gel is 100-200 meshes.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107354202A (en) * | 2017-07-10 | 2017-11-17 | 中国烟草总公司郑州烟草研究院 | Primer for identifying flue-cured tobacco K326 combines and kit, application and authentication method |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107354202A (en) * | 2017-07-10 | 2017-11-17 | 中国烟草总公司郑州烟草研究院 | Primer for identifying flue-cured tobacco K326 combines and kit, application and authentication method |
Non-Patent Citations (2)
| Title |
|---|
| 烟草品种辣椒叶脉斑驳病毒病的症状与抗病性鉴定;杨华兵等;《云南农业大学学报》;20140107;第29卷(第1期);全文 * |
| 香料烟云香巴斯玛1号的化学成分研究;彭梦洁等;《云南农业大学学报（自然科学）》;20180112;第34卷(第1期);全文 * |
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