CN114891010A - Method for extracting and purifying dictamnine compounds in cortex dictamni and application of dictamnine compounds in resisting MRSA (methicillin resistant staphylococcus aureus) - Google Patents
Method for extracting and purifying dictamnine compounds in cortex dictamni and application of dictamnine compounds in resisting MRSA (methicillin resistant staphylococcus aureus) Download PDFInfo
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- CN114891010A CN114891010A CN202210532638.4A CN202210532638A CN114891010A CN 114891010 A CN114891010 A CN 114891010A CN 202210532638 A CN202210532638 A CN 202210532638A CN 114891010 A CN114891010 A CN 114891010A
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Abstract
The invention discloses an extraction and purification method of dictamnine compounds in cortex dictamni and an application of the dictamnine compounds in resisting MRSA, wherein the method comprises the following steps: (1) crushing cortex dictamni, soaking with ethyl acetate, adding sufficient ethyl acetate for reflux extraction, combining extracting solutions, cooling and concentrating to obtain a crude extract after the ethyl acetate is removed; (2) adding sample-mixing silica gel into the extract, drying, making a chromatographic column, performing gradient elution by using a mixed eluent of petroleum ether and acetone, comparing the collected sample with a standard product, and separating to obtain a crude product; (3) recrystallizing the dittanine and 8-hydroxyl dittanine crude products to obtain the dittanine and 8-hydroxyl dittanine pure products. The extraction and purification method has the advantages of simple process, low cost and high purity of the obtained product. In addition, the obtained dictamnine and 8-hydroxyl dictamnine can effectively resist bacteria, have a good antibacterial effect on staphylococcus aureus or escherichia coli, and particularly have an obvious antibacterial effect on MRSA.
Description
Technical Field
The invention belongs to the technical field of extraction of dictamnine compounds, and particularly relates to an extraction and purification method of dictamnine compounds in cortex dictamni and an application of the dictamnine compounds in resisting MRSA.
Background
In recent years, with the improvement of the world medical science and technology level, more and more diseases are overcome by human beings, however, with the excessive use of drugs such as antibiotics, various types of bacteria all generate certain drug resistance, the treatment difficulty after infection is increased, and sometimes even the treatment cannot be performed. According to the world health organization statistics, about 70 million people die each year worldwide due to bacterial resistance. Bacterial drug resistance is becoming a major challenge in the global public health field and is also a key focus of medical industry attention in all countries. Therefore, the development of new drugs with good broad-spectrum antibacterial activity has become a problem to be solved urgently in clinic.
The dictamnine compound has a structural formula (dictamnine: R ═ -H; 8-hydroxyl dictamnine: R ═ -OH)
Dictamnine and 8-hydroxyl dictamnine are dictamnine compounds derived from natural plants, have a furoquinoline structure in structural characteristics, and are mainly extracted from cortex dictamni.
At present, many researches on the extraction of the dictamnine compounds are carried out, but how to extract the high-purity dictamnine compounds by adopting a simpler and more effective method is worthy of further research.
Disclosure of Invention
The purpose of the invention is as follows: aiming at the problems in the prior art, the invention provides a method for extracting and purifying a dictamnine compound from cortex dictamni, which is simple and effective, and the obtained product has high purity.
The technical scheme is as follows: in order to achieve the purpose of the invention, the technical scheme adopted by the invention is as follows:
a method for extracting and purifying dictamnine compounds from cortex dictamni, which comprises the following steps:
(1) crushing cortex dictamni, soaking with ethyl acetate, adding sufficient ethyl acetate for reflux extraction, combining extracting solutions, cooling and concentrating to obtain a crude extract after the ethyl acetate is removed;
(2) adding sample-mixing silica gel into the extract, drying, making a chromatographic column, performing gradient elution by using a mixed eluent of petroleum ether and acetone, comparing the collected sample with a standard product, and separating to obtain a dictamnine crude product and an 8-hydroxyl dictamnine crude product;
(3) recrystallizing the dittanine and 8-hydroxyl dittanine crude products to obtain the dittanine and 8-hydroxyl dittanine pure products.
The obtained dictamnine and 8-hydroxyl dictamnine pure products have the following chemical structures by identification:
preferably, in the step (1), the reflux extraction is performed, and the feed-liquid ratio of the cortex dictamni to the ethyl acetate is 1: (5-7), reflux extracting for 4-6 times, each time for 50-70 min.
Preferably, in the step (1), the concentration is performed by a reduced pressure suction filtration method.
Preferably, in the step (2), the chromatographic column is manufactured by adopting a wet column loading and dry sample loading mode.
Preferably, in the step (2), the petroleum ether and acetone mixed eluent is subjected to gradient elution, and the gradient is set as follows:
petroleum ether: the volume ratio of acetone is 20: 1. 17: 1. 14: 1. 11: 1. 8: 1. 5: 1. 3: 1.
preferably, in the step (2), the collected sample is compared with a standard product, and is compared with a pure product of the dictamnine and the 8-hydroxyl dictamnine by adopting a TLC detection method.
Preferably, in step (3), the dictamnine and the crude 8-hydroxydictamnine are recrystallized from acetone.
The invention also provides application of the prepared dictamnine or 8-hydroxyl dictamnine in preparation of an antibacterial agent.
Further, the invention provides application of the dictamnine or 8-hydroxy dictamnine in preparation of medicines for resisting staphylococcus aureus, methicillin-resistant staphylococcus aureus or escherichia coli.
Antibacterial activity evaluation by a trace broth dilution method shows that the dictamnine and the 8-hydroxyl dictamnine prepared by the invention have good inhibitory activity to staphylococcus aureus, and the MIC of the dictamnine to a methicillin-resistant staphylococcus aureus (MRSA) clinical isolate is 16-128 mu g/mL; the Minimum Inhibitory Concentration (MIC) of the 8-hydroxyl dictamnine to the standard staphylococcus aureus 29213 and the standard escherichia coli 25922 is 64-128 mu g/mL.
The technical effects are as follows: compared with the prior art, the extraction and purification method has the advantages of simple process and low cost, can effectively and simultaneously extract the dictamnine compounds dictamnine and 8-hydroxyl dictamnine, and has high purity of the obtained product which can reach more than 95 percent. In addition, experiments prove that the obtained dictamnine and 8-hydroxyl dictamnine can effectively resist bacteria, have a good antibacterial effect on staphylococcus aureus or escherichia coli, and particularly have an obvious antibacterial effect on MRSA. Therefore, the dictamnine and the 8-hydroxyl dictamnine are expected to be used as new antibacterial leads to be deeply researched, and have important significance for finding new antibacterial lead.
Drawings
FIG. 1 is the nuclear magnetic hydrogen spectrum of dictamnine.
FIG. 2 is the nuclear magnetic carbon spectrum of dictamnine.
FIG. 3 is the nuclear magnetic hydrogen spectrum of 8-hydroxy dictamnine of the present invention.
Detailed Description
The present invention is further illustrated by the following examples.
Example 1 preparation of dictamnine
Crushing 5kg of dittany bark, soaking in ethyl acetate, and mixing the materials in a liquid-material ratio of 1: extracting under reflux for 5 times (1 h each time) under 6 (cortex Dictamni Radicis: ethyl acetate), concentrating under reduced pressure to remove ethyl acetate, adding the obtained extract into silica gel, spin drying, performing column chromatography by wet method and dry method, and eluting with eluent (petroleum ether: the acetone (v/v) ratios were 20: 1. 17: 1. 14: 1. 11: 1. 8: 1. 5: 1. 3: performing gradient elution, simultaneously performing TLC detection and standard substance control, merging eluent according to TLC detection result, spin-drying, and recrystallizing with acetone to obtain pure dictamnine with purity of 96%.
Physicochemical properties of dictamnine:
1) yellow crystals, melting point 133-.
2) Nuclear magnetic resonance spectrum of the compound ( 1 H/ 13 C NMR, 400MHz) characteristics:
using deuterated chloroform as a solvent and TMS as an internal standard, wherein the attribution of each peak is as follows: 1 H NMR(400MHz CDCl 3 )δ:8.26(dd,J＝8.4,1.2Hz,1H,H-8),8.00(d,1H，J＝8.4Hz，H-5),7.66-7.70(m,1H，H-7),7.62(d,1H,J＝2.8Hz,H-2),7.46-7.42(m,1H,H-6),7.07(d,1H,J＝2.8Hz,H-3),4.44(s,3H,-OCH 3 )； 13 C NMR(100MHz CDCl 3 )δ:163.80,156.86,145.59,143.55,129.62,127.77,123.73,122.37,118.69,104.75,103.41,59.01.
EXAMPLE 28 preparation of Hydroxydictamnine
Crushing 5kg of dittany bark, soaking in ethyl acetate, and mixing the materials in a liquid-material ratio of 1: extracting under reflux for 5 times (1 h each time) under 6 (cortex Dictamni Radicis: ethyl acetate), concentrating under reduced pressure to remove ethyl acetate, adding the obtained extract into silica gel, spin-drying, performing column chromatography by wet method and dry method, and eluting with eluent (petroleum ether: the acetone (v/v) ratios were 20: 1. 17: 1. 14: 1. 11: 1. 8: 1. 5: 1. 3: performing gradient elution, simultaneously performing TLC detection and standard substance control, merging eluent according to TLC detection result, spin-drying, and recrystallizing with acetone to obtain 8-hydroxy dictamnine pure product with purity of 97%.
The physicochemical properties of compound 2 are as follows:
1) white crystals, melting point 148-.
2) NMR spectrum of the compound (A) 1 H NMR, 400MHz) characteristics:
using deuterated chloroform as a solvent and TMS as an internal standard, wherein the attribution of each peak is as follows: 1 H NMR(400MHz CDCl 3 )δ:7.71-7.74(m,2H,-OH and H-5),7.61(d,1H,J＝2.8Hz,H-2),7.31-7.35(m,1H，H-6),7.17(dd,1H,J＝7.6,1.2Hz,H-4),7.09(d,1H,J＝2.8Hz,H-3),4.44(s,3H,-OCH 3 )。
application example 1: in vitro antimicrobial Activity assay
1. Test bacteria:
staphylococcus aureus (s.aureus ATCC 29213); escherichia coli (e.coil ATCC 25922); MRSA 11-23 (clinical isolate)
2. Sample and reagent:
the samples were: dictamnine and 8-hydroxydictamnine prepared in the examples.
3. The test method comprises the following steps:
performing in-vitro antibacterial activity test on the product dictamnine and 8-hydroxyl dictamnine on a 96-well plate by adopting a trace broth dilution method, selecting a bacterial colony by using an inoculating loop, inoculating the bacterial colony in 5mL of aqueous casein broth culture medium, culturing at 37 ℃ for 2-6h, correcting the concentration to 0.5 McLeod's turbidimetric tube standard by using MHB broth after the bacterial number is increased, wherein the concentration is about 1-2 multiplied by 10 8 CFU/mL. The bacterial suspension was diluted 1:100 with MHB broth for use. Sample 2.56mg was weighed, dissolved in 200. mu.L DMSO, and then diluted 50-fold with MHB broth or physiological saline to obtain a sample stock solution. Taking a sterile 96-well plate, adding 200 mu L of antibacterial agent into a first well by using an instrument liquid gun, adding 100 mu L of MHB broth culture medium into 2-10 wells respectively, taking 100 mu L of the antibacterial agent from the 1 st well, adding the antibacterial agent into the 2 nd well, uniformly mixing, taking 100 mu L of the antibacterial agent from the 2 nd well, adding the antibacterial agent into the 3 rd well, and repeating the steps until 100 mu L of the antibacterial agent is taken out from the 10 th well, and discarding, wherein the concentration of the antibacterial agent in each well is 256 mu g/mL, 128 mu L, 64 mu L, 32 mu L, 16 mu L, 8 mu L, 4 mu L, 2 mu L, 1 mu L and 0.5 mu g/mL in sequence. 200. mu.L of the inoculum was added to well 11 as a positive control, and 200. mu.L of MHB broth was added to well 12 as a negative controlThen, 100 mu L of the prepared bacterial liquid is added into each of the 1-10 holes, so that the concentration of the drug in the 1-10 holes is 128, 64, 32, 16, 8, 4, 2, 1, 0.5 and 0.25 mu g/mL in sequence. And placing the inoculated 96-well plate in an incubator at 37 ℃ for culturing for 16-20 h, observing the result, measuring the OD value of each well at 600nm by using an enzyme-labeled analyzer, and observing the drug concentration of the completely clarified well by naked eyes to obtain the MIC value.
TABLE 1 in vitro bacteriostatic activity (μ g/mL) of dictamnine and 8-hydroxydictamnine of the invention
a ND-not tested
As shown in Table 1, the dictamnine and the 8-hydroxyl dictamnine prepared by the method have certain bacteriostatic activity on staphylococcus aureus and escherichia coli, the Minimum Inhibitory Concentration (MIC) is 64-128 mu g/mL, and the potential broad-spectrum antibacterial property is embodied. Therefore, the dictamnine and the 8-hydroxyl dictamnine prepared by the method are expected to be used for preparing potential antibacterial drug lead molecules.
TABLE 2 anti-MRSA activity of dictamnine and 8-hydroxydictamnine of the invention (μ g/mL)
As can be seen from Table 2, the dictamnine and 8-hydroxydictamnine prepared by the invention have certain inhibitory activity to clinically isolated MRSA strains, and the MIC value is 16-128 mug/mL. Compared with the dictamnine extract, the monomer dictamnine has better MRSA resistance activity, wherein the minimum inhibitory concentration to a clinical isolate M-14 is 16 mug/mL. In conclusion, the dictamnine and the 8-hydroxyl dictamnine prepared by the method have good MRSA (methicillin resistant SA) activity, are expected to be used as lead molecules for preparing novel antibacterial drugs, are subjected to structure optimization, and are further deeply researched.
Claims (9)
1. A method for extracting and purifying dictamnine compounds from cortex dictamni, which is characterized by comprising the following steps:
(1) crushing cortex dictamni, soaking with ethyl acetate, adding sufficient ethyl acetate for reflux extraction, combining extracting solutions, cooling and concentrating to obtain a crude extract after the ethyl acetate is removed;
(2) adding sample-mixing silica gel into the extract, drying, making a chromatographic column, performing gradient elution by using a mixed eluent of petroleum ether and acetone, comparing the collected sample with a standard product, and separating to obtain a dictamnine crude product and an 8-hydroxyl dictamnine crude product;
(3) recrystallizing the crude dictamnine and 8-hydroxyl dictamnine to obtain the purified dictamnine and 8-hydroxyl dictamnine.
2. The method for extracting and purifying dictamnine compounds from cortex dictamni as claimed in claim 1, wherein in the step (1), the reflux extraction is performed, and the feed-liquid ratio of cortex dictamni to ethyl acetate is 1: (5-7), reflux extracting for 4-6 times, each time for 50-70 min.
3. The method for extracting and purifying dictamnine compounds from cortex dictamni as claimed in claim 1, wherein in the step (1), the concentration is performed by a vacuum filtration method.
4. The method for extracting and purifying dictamnine compounds from cortex dictamni as claimed in claim 1, wherein in the step (2), the chromatographic column is prepared by wet-method column packing and dry-method sample loading.
5. The method for extracting and purifying dictamnine compounds from cortex dictamni as claimed in claim 1, wherein in the step (2), the mixed eluent of petroleum ether and acetone is subjected to gradient elution, and the gradient is set as follows:
petroleum ether: the volume ratio of acetone is 20: 1. 17: 1. 14: 1. 11: 1. 8: 1. 5: 1. 3: 1.
6. the method for extracting and purifying dictamnine compounds from cortex dictamni as claimed in claim 1, wherein in step (2), the collected sample is compared with standard sample by TLC detection method, and compared with pure products of dictamnine and 8-hydroxy dictamnine.
7. The method for extracting and purifying dictamnine compounds from cortex dictamni as claimed in claim 1, wherein in step (3), dictamnine and crude 8-hydroxy dictamnine are recrystallized in acetone.
8. Use of dictamnine or 8-hydroxydictamnine prepared as in claim 1 for the preparation of an antibacterial agent.
9. Use of dictamnine or 8-hydroxydictamnine in the manufacture of a medicament against staphylococcus aureus, methicillin-resistant staphylococcus aureus (MRSA) or escherichia coli.
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| CN116693485A (en) * | 2023-06-07 | 2023-09-05 | 齐齐哈尔医学院 | Dittany ester C and preparation method and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116693485A (en) * | 2023-06-07 | 2023-09-05 | 齐齐哈尔医学院 | Dittany ester C and preparation method and application thereof |
| CN116693485B (en) * | 2023-06-07 | 2023-11-21 | 齐齐哈尔医学院 | Dittany ester C and preparation method and application thereof |
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