CN112174848B - Oleoylethanolamide compound with antibacterial activity in parasitic loranthus, preparation method and application thereof - Google Patents
Oleoylethanolamide compound with antibacterial activity in parasitic loranthus, preparation method and application thereof Download PDFInfo
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Abstract
An oleamide ethanolamine compound with antibacterial activity in parasitic loranthus, a preparation method and application thereof in preparing antibacterial drugs, belonging to the field of phytochemistry. Taking herba Taxilli as raw material, sun drying, pulverizing, soaking in organic solvent, extracting, mixing extractive solutions, filtering, and concentrating to obtain herba Taxilli extract; performing silica gel column chromatography, performing gradient elution by using a mixed solution of trichloromethane and methanol, wherein the volume percentage of the trichloromethane in the mixed solution is 70-80%, collecting eluent, and concentrating the eluent to the relative density of 1.08-1.25; then separating and purifying by high performance liquid chromatography and gel column chromatography to obtain the target product. An antibacterial experiment shows that the minimum inhibitory concentration MIC value of the product to methicillin-resistant staphylococcus aureus is 2-8 mug/mL, and the antibacterial effect of the product is far better than that of gentamicin; in addition, the product of the invention has low toxicity and good antibacterial effect, and can provide a high-efficiency and low-toxicity pilot compound for the research and development of antibacterial drugs.
Description
Technical Field
The invention belongs to the field of phytochemistry, and particularly relates to an oleamide ethanolamine compound with antibacterial activity in loranthus parasiticus, a preparation method and application thereof in preparation of antibacterial drugs.
Background
Loranthus parasiticus (Taxillu μ s chinensis (DC.) Danser), the original name Loranthus parasiticus, also called Guangsheng parasitic, is a plant of Loranthus parasiticus of Loranthaceae of Santalaceae, and is mainly distributed in Yunnan, Sichuan, Gansu, Shaanxi, Shanxi, Henan, Guizhou, Hubei, Hunan and other places in China.
On one hand, the parasitic loranthus harms host plants to different degrees, affects the growth, flowering and fructification of the host plants, causes the reduction of yield or the loss of yield of fruit trees or economic trees, and leads to pruning or withering of the whole plants when the host plants are seriously damaged. Therefore, in the growth of many important economic crops, parasitic loranthus is considered to be a parasitic plant hazard, also known as "parasitic loranthus".
On the other hand, the branches and leaves of the parasitic loranthus are rich in various functional substances such as flavone, alkaloid, terpenoids, polypeptide, protein, agglutinin, polysaccharide, organic acid and the like, so that the parasitic loranthus becomes one of important medicinal plants in the traditional medicine of the parasitic loranthus. Loranthus parasiticus recorded in pharmacopoeia of the people's republic of China in 2015 is a dry plant with leaves and stems belonging to the Loranthaceae family. In the traditional clinical application, the loranthus parasiticus has the functions of tonifying liver and kidney, dispelling wind and dampness, strengthening muscles and bones, nourishing blood, preventing miscarriage and reducing blood pressure. However, the related researches on the pharmacology of the loranthus parasiticus show that the loranthus parasiticus also has good effects on hypertension, stroke, inflammation, hyperlipidemia, threatened abortion, arrhythmia and the like.
In the medical field, the incidence of infection has increased year by year, and antibiotic therapy is mainly used clinically in recent years. However, the abuse of antibiotics causes the appearance of drug-resistant bacteria, so that the antibiotics can treat symptoms and root causes but not cause the symptoms, and the adverse reactions are more. The search for high-efficiency and low-toxicity antibacterial active molecules from natural plants is also a research hotspot of the current natural product chemistry. Clinically, various medicinal plant resources are widely used for treating various infectious diseases, such as coptis chinensis, phellodendron, mint, forsythia, honeysuckle, plantain seed and the like.
Chinese invention patents CN102579413A (new application of oleoylethanolamide and derivatives thereof), CN106821781A (skin whitening cosmetic composition and application thereof), and CN102579414A (application of oleoylethanolamide as a medicament for reducing blood fat and preventing and treating non-alcoholic fatty liver) disclose functional activities and applications of oleoylethanolamide in reducing blood fat, inhibiting tyrosinase activity, controlling liver inflammation level caused by fatty liver and the like, but no report of antibacterial activity is found. The oleoylethanolamide is separated from the traditional Chinese medicine parasitic loranthus for the first time through experiments, the antibacterial activity of the oleoylethanolamide is proved for the first time, and a basis is provided for the application of the parasitic loranthus and the oleoylethanolamide in the aspect of infectious diseases.
In conclusion, in order to fully utilize the parasitic loranthus resources, recycle the plants which are not needed in agricultural production and are harmfully harmed by the parasitism, reduce the disposal of the plants in the environment to the maximum extent, follow the green chemical principle and widen the application path, the invention proves that the parasitic loranthus is a natural medicinal plant which can be used as a source for providing a new antibacterial medicament. The invention researches the chemical components of the parasitic loranthus and separates out a fatty acid ethanolamine compound which is oleoylethanolamide and has good antibacterial effect.
Disclosure of Invention
The first purpose of the invention is to provide an oleoylethanolamide compound with antibacterial activity in parasitic loranthus, the second purpose of the invention is to provide a preparation method of the oleoylethanolamide compound, and the third purpose of the invention is to provide the application of the oleoylethanolamide compound in preparing antibacterial drugs.
The invention relates to an oleoylethanolamide compound with antibacterial activity in parasitic loranthus, which is named oleoylethanolamide in Chinese and N-oleoyl ethanolamine in English, and has a molecular formula of C20H39NO2The structural formula is as follows:
the invention relates to a preparation method of an oleamide ethanolamine compound with antibacterial activity in parasitic loranthus, which comprises the following steps:
A. sample extraction: taking herba taxilli as a raw material, drying the herba taxilli, crushing the herba taxilli into 10-70 meshes, soaking and extracting the herba taxilli for 2-4 times by using an organic solvent, combining extracting solutions, filtering and concentrating the extracting solutions until the relative density is 1.08-1.25 to obtain a herba taxilli extract;
B. silica gel column chromatography: dissolving the extract of the parasitic loranthus extract obtained in the step A by using 1-3 times of acetone, ethanol or methanol by weight of the extract, mixing the extract by using 1-1.5 times of 60-120-mesh silica gel by weight of the extract, performing silica gel column chromatography, performing gradient elution by using a mixed solution of trichloromethane and methanol, wherein the volume percentage of the trichloromethane in the mixed solution of the trichloromethane and the methanol is 70-80%, collecting eluent, and concentrating to the relative density of 1.08-1.25;
C. high-pressure liquid chromatography separation: separating and purifying the sample obtained by elution and concentration in the step B by high performance liquid chromatography to obtain a target crude product;
D. purifying by using a gel column: and D, dissolving the crude target product in the step C by using isopropanol, taking the isopropanol as a mobile phase, and further separating and purifying by using gel column chromatography to obtain a pure oleoylethanolamide compound.
In the step A, the organic solvent is ethanol with the mass fraction of 60-95%; in the step A, 5-10 times of the mass of the organic solvent is used for extraction every time, and the extraction time is 2-8 hours.
In the step C, the conditions of the high performance liquid chromatography separation and purification are as follows:
taking a normal-phase silica gel column (200-300 meshes) as a stationary phase, and taking a mobile phase A as n-heptane: isopropanol (volume ratio 0.5-0.8: 1), and the mobile phase B is n-heptane: isopropyl alcohol: adding water (the volume ratio is 2.5-3: 5-6: 1), adding the mobile phase A and the mobile phase B by double pumps, and adding 1-5 mL/min; and (3) at the column temperature of 35-45 ℃, with the sample injection amount of 0.5-1.0 mL, collecting chromatographic peaks with the retention time of 10-12 min, collecting the solution, and evaporating to dryness to obtain a crude target product.
The application of the oleoylethanolamide compound with antibacterial activity in the parasitic loranthus in preparing antibacterial medicaments comprises oleoylethanolamide and/or a pharmaceutically acceptable carrier or excipient of oleoylethanolamide.
The invention has the beneficial effects that:
1. the invention takes the loranthus parasiticus as a raw material to extract an oleoyl ethanolamine compound with antibacterial activity, which has stronger antibacterial action, and antibacterial experiments show that the minimum inhibitory concentration MIC value of the compound to methicillin-resistant staphylococcus aureus is 2-8 mug/mL, and the antibacterial effect of the compound is far better than that of a control group gentamicin (MIC is 512 mug/mL); in addition, the obtained oleoylethanolamide compound has low toxicity and good antibacterial effect, and can provide a high-efficiency and low-toxicity pilot compound for the research and development of antibacterial drugs.
2. The preparation method of the compound is simple, and in addition, the loranthus parasiticus is widely distributed in China, grows rapidly, has wide raw material sources and low cost, and can continuously provide raw materials for the separation and preparation of the active compound, so that the compound can be continuously produced and prepared in a large scale.
3. The antibacterial activity of the medicinal plant parasitic loranthus is never reported in the published documents, so that the antibacterial activity research of the medicinal plant parasitic loranthus widens the application way and increases the medicinal value.
4. The compound is oleoylethanolamide, and the antibacterial activity of the compound is never reported in the published literature, so that the analysis of the antibacterial activity of the compound provides a new idea for the screening of antibacterial drugs and the research and development of antibacterial mechanisms.
Drawings
FIG. 1: the high performance liquid chromatogram of the oleoylethanolamide compound prepared by the invention;
FIG. 2: the primary mass spectrogram of the oleoylethanolamide compound prepared by the method;
FIG. 3: the secondary mass spectrum of the oleoylethanolamide compound prepared by the method is disclosed.
As shown in FIG. 1, the high performance liquid chromatogram of oleoylethanolamide was plotted with Retention Time (RT) as abscissa and response value as ordinate. Data preliminary arrangement of high-resolution liquid quality collection is completed through CD2.1(Thermo Fisher) and is compared with a database of mzCloud, mzVault and ChemSepider, the name and the molecular formula of a compound are imported from the database, non-target screening is carried out, and the retention time of the screened compound is reserved. As shown in FIG. 1, oleoylethanolamide was detected at 21.662 min.
As shown in fig. 2, the primary mass spectrum of oleoylethanolamide positive ion detection is a mass spectrum with the ion signal intensity detected by the detector as ordinate and the ratio (m/z, mass-to-charge ratio) of the ion mass number (m) to the charge number (z) as abscissa. Data preliminary arrangement is completed by using data collected by high-resolution liquid quality through CD2.1(Thermo Fisher), then database comparison and search are carried out with mzCloud, mzVallt and ChemSpider, the name and molecular formula of the compound are led in from the database, non-target screening is carried out, and the molecular ions of the screened compound are reserved. As shown in FIG. 2, the molecular ion peak m/z326.30511 is generated in positive ion mode.
FIG. 3 shows the secondary mass spectrum of oleoylethanolamide positive ion detection. The bar graph is drawn by taking the intensity of an ion signal detected by a detector as an ordinate and taking the ratio (m/z, mass-to-charge ratio) of the mass number (m) to the charge number (z) of a daughter ion formed by dissociation of oleoylethanolamide parent ions as an abscissa.
Data preliminary arrangement is completed by using data collected by high-resolution liquid quality through CD2.1(Thermo Fisher), then database comparison and retrieval are carried out on the data, names and molecular formulas of compounds are led in from a database, non-target screening is carried out, related information of the screened compounds is retained, secondary fragment ions are matched with component structures, and components are identified according to the matching degree of more than 80% and the fracture rule of the component fragment ions.
Oleoylethanolamide is an ethanolamine compound and generates a molecular ion peak m/z326.30511 in a positive ion mode. MS in Positive ion mode2Fragment ion M/z 308.29486[ M + H-H ] visible in spectrum2O]+,265.25131[M+H-H2O-peptide bond]+,247.24040[M+H-2H2O-peptide bond]+It is presumed that the cleavage process of dehydration and deamidation occurs.
Detailed Description
The invention is further described below in conjunction with specific embodiments, the advantages and features of which will become apparent from the description. These examples are illustrative only and do not limit the scope of the present invention in any way. It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention, and that such changes and modifications may be within the scope of the invention.
Example 1: preparation of compound with antibacterial activity in parasitic loranthus
Drying herba Taxilli in the sun, pulverizing to 60 mesh, extracting 3kg of the sample with 95% ethanol water solution for 3 times, each time for 8 hr; mixing the extractive solutions obtained in 3 times, filtering, and concentrating under reduced pressure to obtain herba Taxilli extract 160 g. Dissolving herba Taxilli extract with 180g methanol, adding 200g coarse silica gel of 80 mesh, loading onto column with 1.0kg silica gel of 160 mesh, and loading onto silica gel column for chromatography; the volume ratio is 75: 25, gradient elution is carried out on the mixed solution of the trichloromethane and the methanol, the eluent is collected and concentrated to the relative density of 1.15, and the eluent is collected and concentrated to obtain 15.6g of concentrate. A normal-phase silica gel column chromatographic column (250 meshes) is used as a stationary phase, a mobile phase A is n-heptane-isopropanol (64: 115, v/v), a mobile phase B is n-heptane-isopropanol-water (30: 63: 12, v/v/v), and the flow rate is 1.0 mL/min. The column temperature is 40 ℃, the sample injection amount is 1mL, the chromatographic peak with the retention time of 11.83min is collected, the solution is collected and evaporated to dryness, and the crude oleoylethanolamide product is obtained; and dissolving the crude oleoylethanolamide product by using isopropanol, and purifying by using Sephadex LH-20 gel column chromatography by using the isopropanol as a mobile phase to obtain 1.2g of pure oleoylethanolamide product.
Example 2: determination of antibacterial Activity of Compounds having antibacterial Activity in Taxus chinensis
1. Experimental materials and methods
1.1 strains and reagents: methicillin-resistant staphylococcus aureus ATCC43300 (guangdong province strain preservation center); BHI agar medium (Kyork, Guangdong, Microscience, Inc.); MH broth medium (guangdong cika microbiology ltd); sterile TTC solution (cantonese microbiology co.
1.2 strain activation: after being recovered, the methicillin-resistant staphylococcus aureus ATCC43300 freeze-dried powder is inoculated into a BHI culture medium and is put into a constant temperature incubator at 37 ℃ for culture for 12 hours. And (4) carrying out subculturing, purifying and culturing on the methicillin-resistant staphylococcus aureus by using the same inoculation method for later use.
1.3 preparation of the medicine: accurately weighing 4.096g of pure oleoylethanolamide prepared in example 1, dissolving the oleoylethanolamide in 10mL of dimethyl sulfoxide (DMSO) with the mass fraction of 50%, wherein the concentration of the oleoylethanolamide is 409.6mg/mL, and taking the oleoylethanolamide as stock solution; 1mL of the stock solution was filtered through a 0.22 μm microporous membrane for sterilization and diluted with water to 4096 μ g/mL for MIC measurement. 0.4096g of gentamicin sulfate is accurately weighed and dissolved in 100mL of water, the concentration of the gentamicin sulfate is 4096 mu g/mL, and 1mL of gentamicin sulfate solution is filtered and sterilized by a 0.22 mu m microporous filter membrane for measuring MIC.
1.4 preparation of bacterial liquid: and (3) placing the test tube in a McLeod turbidimeter, adding a certain amount of normal saline, displaying by a turbidimeter regulator 100, adding the passaged methicillin-resistant staphylococcus aureus obtained in the step 1.1, and displaying the concentration of the bacteria regulating liquid to 85. Then the bacterial liquid is diluted by 1000 times by MH culture liquid, and the concentration of methicillin-resistant staphylococcus aureus in the diluted bacterial liquid is about 1.0 multiplied by 105cfμ/mL。
1.5 MIC determination by two-fold dilution method: 100 mu L of MH broth culture medium sterilized at high temperature is added into each hole of a sterile 96-hole plate (8 rows and 12 columns), then 100 mu L of oleoylethanolamide liquid medicine of 4096 mu g/mL is added into the 1 st hole of each row, after uniform mixing, 100 mu L of mixed liquid in the 1 st hole is absorbed and added into the 2 nd hole, and the 2 nd to 10 th holes are filled according to the double dilution method. To the 11 th well of the row, 100. mu.L of the gentamicin sulfate solution 4096. mu.g/mL obtained in step 1.3 was added as a positive control, and to the 12 th well of the row, 100. mu.L of a DMSO solution with a mass fraction of 1% was added as a negative control. Finally, the concentration obtained in the step 1.4 is added into each hole of each row, and the concentration is 1.0 multiplied by 105cfu/mL bacterial suspension 100 uL. Three sets of parallel tests were set according to the loading method described above, and the measurement results were averaged over the three sets of measurements. Taking 0.5% TTC solution, adding 5 μ L of TTC solution into each hole of each row, and mixing; after sealing with a sealing film, culturing at 35 ℃ for 24 h.
2. Results of the experiment
MIC determination of oleoylethanolamide for methicillin-resistant Staphylococcus aureus: each hole of 1% DMSO is dyed, and the antibacterial effect is avoided; the MIC value of oleoylethanolamide to methicillin-resistant staphylococcus aureus ATCC43300 is 4 mug/mL, and the MIC value of gentamicin sulfate to methicillin-resistant staphylococcus aureus ATCC43300 is 512 mug/mL, so that the significant difference is achieved.
Claims (2)
1. A preparation method of oleamide ethanolamine compound with antibacterial activity in parasitic loranthus comprises the following steps:
A. sample extraction: taking herba taxilli as a raw material, drying and crushing the herba taxilli, grinding the herba taxilli to 10-70 meshes, soaking and extracting the herba taxilli for 2-4 times by using ethanol with the mass fraction of 60-95%, and then combining, filtering and concentrating the extracting solution to the relative density of 1.08-1.25 to obtain a herba taxilli extract;
B. silica gel column chromatography: dissolving the extract of the parasitic loranthus extract obtained in the step A by using 1-3 times of acetone, ethanol or methanol by weight of the extract, mixing the extract by using 1-1.5 times of 60-120-mesh silica gel by weight of the extract, performing silica gel column chromatography, performing gradient elution by using a mixed solution of trichloromethane and methanol, wherein the volume percentage of the trichloromethane in the mixed solution of the trichloromethane and the methanol is 70-80%, collecting eluent, and concentrating to the relative density of 1.08-1.25;
C. high-pressure liquid chromatography separation: separating and purifying the sample obtained by elution and concentration in the step B by high performance liquid chromatography to obtain a target crude product; the high performance liquid chromatography separation and purification uses a 200-300 mesh normal phase silica gel column as a stationary phase, and a mobile phase A is a solid phase with a volume ratio of 0.5-0.8: 1 of n-heptane and isopropanol, wherein the mobile phase B is a mixture of n-heptane and isopropanol in a volume ratio of 2.5-3: 5-6: 1, adding n-heptane, isopropanol and water into a mobile phase A and a mobile phase B by double pumps at a flow rate of 1-5 mL/min; the column temperature is 35-45 ℃, the sample injection amount is 0.5-1.0 mL, chromatographic peaks with the retention time of 10-12 min are collected, the solution is collected, and a target crude product is obtained after evaporation to dryness;
D. purifying by using a gel column: c, dissolving the crude target product in the step C by using isopropanol as a mobile phase, and further separating and purifying by using gel column chromatography to obtain a pure oleoylethanolamide compound product with the molecular formula of C20H39NO2The structural formula is shown as follows,
2. a method for preparing oleamide ethanolamine compound with antibacterial activity in Taxus chinensis as claimed in claim 1, wherein: in the step A, 5-10 times of the mass of the ethanol is used for extraction every time, and the extraction time is 2-8 hours.
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