CN108836990B - Anti-inflammatory active component of honeysuckle leaves and preparation method and application thereof - Google Patents
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Abstract
The invention relates to a preparation method of anti-inflammatory active components of honeysuckle leaves, which comprises the following steps: 1) defatting pulverized dried folium Lonicerae with petroleum ether, and reflux-extracting with methanol to obtain viscous crude extract; 2) dissolving the viscous crude extract with water for the second time to obtain suspension, extracting with n-butanol, and concentrating under reduced pressure to obtain n-butanol phase; 3) separating n-butanol phase by column chromatography, eluting with 10%, 20%, 30%, 40%, 50%, 60% and 70% methanol water solution, respectively, and eluting with 50% methanol water solution to obtain fraction. According to the invention, through the research on the inhibiting effect of the 5-LOX, the research on the anti-inflammatory effect of a macrophage system RAW264.7 of a mouse and the research on the anti-inflammatory effect of foot swelling of a rat, the anti-inflammatory active component (M1) of honeysuckle leaves is found to have excellent anti-inflammatory activity, and a theoretical basis can be provided for the research and development of anti-inflammatory drugs.
Description
Technical Field
The invention belongs to the technical field of analytical chemistry and biological medicine, and particularly relates to a honeysuckle anti-inflammatory active component, a preparation method and anti-inflammatory application thereof.
Background
Lonicera japonica (Lonicera japonica, British name) and Lonicera japonica (Lonicera japonica, Lonicera, Caprifoliaceae) are semi-evergreen liana and originally recorded in the miscellaneous records of famous physicians. As a common traditional Chinese medicine with a long history, more than 500 traditional Chinese medicine prescriptions containing honeysuckle are recorded in the pharmacopoeia of the people's republic of China since 1995. Honeysuckle Leaves (Leaves of Lonicera japonica, LLJ for short) are recorded as early as in the Ming and Qing era as "honeysuckle stem and leaf function is the same" and "vine Leaves are all used". The honeysuckle is cold in nature and sweet in taste, and has the effects of clearing away heat and toxic materials and dispelling wind and heat.
In the prior art, honeysuckle is commonly used for making tea or tea beverage, such as a preparation method of CN201510718865.6 honeysuckle tea, and a Chinese patent CN200810074299.X discloses a honeysuckle tea beverage and the like. Inflammation is the stress defense reaction of body tissues to injury factors, and traumatic infection on the body surface and common multiple diseases of various tissues and organs belong to inflammatory diseases. At present, no reports about the anti-inflammatory activity of honeysuckle leaves exist. Therefore, the research on the anti-inflammatory activity of the honeysuckle leaves is significant, and the resource utilization rate of the honeysuckle leaves as non-medicinal parts can be effectively improved.
Disclosure of Invention
The invention aims to overcome the defects of the prior art, provides an anti-inflammatory active component of honeysuckle leaves and provides a theoretical basis for the research and development of anti-inflammatory drugs.
The invention also provides a preparation method and application of the anti-inflammatory active component of honeysuckle leaves.
In order to achieve the purpose, the invention adopts the following technical scheme:
a preparation method of anti-inflammatory active components of honeysuckle leaves comprises the following steps:
1) defatting pulverized dried folium Lonicerae with petroleum ether, and reflux-extracting with methanol to obtain viscous crude extract;
2) dissolving the viscous crude extract with water for the second time to obtain suspension, extracting with n-butanol, and concentrating under reduced pressure to obtain n-butanol phase;
3) performing column chromatography separation on the n-butanol phase, eluting with 10%, 20%, 30%, 40%, 50%, 60% and 70% methanol water solution, respectively, and selecting 50% methanol water solution to elute to obtain fraction which is the anti-inflammatory active component of folium Lonicerae.
In order to obtain a better degreasing treatment effect, in the step 1), the degreasing treatment specifically comprises the following steps: mixing the crushed dried honeysuckle leaves and petroleum ether according to the ratio of material to liquid of 1 g: mixing 20-60 ml in Soxhlet extractor, and defatting at 70-90 deg.C until the Soxhlet extractor solution turns colorless.
In order to obtain a better reflux extraction effect, in the step 1), the reflux extraction specifically comprises the following steps: according to the material-liquid ratio of 1 g: adding 70-95% methanol into 10-50 ml, reflux-extracting for 2-5 times, each time for 2-5 h, and combining the extractive solutions to obtain viscous crude extract after reflux-extracting.
In order to obtain better extraction effect, in the step 2), the viscous crude extract is ultrasonically dissolved by secondary water to obtain suspension, and then the suspension is extracted by n-butyl alcohol in the same volume.
The invention provides the honeysuckle anti-inflammatory active component prepared by the preparation method.
The invention also provides application of the honeysuckle anti-inflammatory active component in anti-inflammatory research of in vitro enzyme models, macrophage models and mouse foot swelling models.
The invention also provides application of the honeysuckle anti-inflammatory active component in preparing anti-inflammatory drugs.
Compared with the prior art, the invention has the beneficial effects that:
1) the preparation method is simple and easy to operate, and the prepared anti-inflammatory active components of honeysuckle leaves are applied to anti-inflammatory research of in vitro enzyme models, macrophage models and mouse foot swelling models, so that a theoretical basis is provided for research and development of related anti-inflammatory drugs of honeysuckle leaves;
2) the invention prepares the anti-inflammatory active component of the honeysuckle leaves for the first time, and the HPLC analysis shows that: the gradient elution reagent mainly contains five compounds, has less impurities than other gradient elution fractions, and is beneficial to the qualitative and quantitative determination of subsequent compounds. In addition, the research on the anti-inflammatory activity of the mixture after separation and purification is more efficient and targeted than the research on the anti-inflammatory activity of the crude honeysuckle leaf extract reported in the prior literature.
Drawings
FIG. 1 is an HPLC chart of the anti-inflammatory active ingredient (M1) of honeysuckle leaves obtained in example 1;
FIG. 2 is a dose-effect relationship diagram of the anti-inflammatory active component (M1) from honeysuckle leaves obtained in example 1 for inhibiting 5-LOX activity;
FIG. 3 is a graph showing the effect of the anti-inflammatory active ingredient (M1, 60 μ M) from honeysuckle leaves obtained in example 1 on the morphology of RAW264.7 cells; the experiment was set up for 4 groups, as follows: normal group (no test sample, no LPS); model group (100 ng/ml LPS); experimental group (60 μ M M1+ LPS); negative control group (60 μ M M1);
FIG. 4 is a graph showing the inhibitory effect of the anti-inflammatory active ingredient (M1) from Lonicera japonica leaves obtained in example 1 on lameness swelling of mice, dexamethasone and physiological saline are respectively used as positive and negative control groups, and n-butanol phase (JYHN-B) and M1 of Lonicera japonica leaves are used as experimental groups.
Detailed Description
The technical solutions of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it should be understood that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be obtained by a person skilled in the art without inventive effort based on the embodiments of the present invention, are within the scope of the present invention.
In the following examples, unless otherwise specified, methanol is referred to as a volume concentration.
Example 1
A preparation method of anti-inflammatory active components from honeysuckle leaves comprises the following steps:
1) extracting chemical components of honeysuckle leaves: picking up about 114g of fresh honeysuckle leaves, drying the fresh honeysuckle leaves in a drying oven at 40 ℃ until the weight is constant to obtain about 37g of dried honeysuckle leaves, crushing the dried honeysuckle leaves, and sieving the crushed honeysuckle leaves with a 60-mesh sieve. Precisely weighing 10g of dried honeysuckle leaf sample which is sieved by a 60-mesh sieve, placing the dried honeysuckle leaf sample into a Soxhlet extractor, and adding 200ml of petroleum ether to carry out degreasing treatment at 80 ℃ until the solution in the Soxhlet extractor becomes colorless. Defatting, air drying, reflux-extracting with 500ml 80% methanol at 80 deg.C for 3 times (each time for 3 hr), and mixing the 3 extractive solutions to obtain brown viscous crude extract;
2) ultrasonically dissolving the crude extract with secondary water to a suspension state, extracting with n-butanol of the same volume, and concentrating the extract under reduced pressure to obtain n-butanol phase of about 1.4 g;
3) and (3) column chromatography separation: a chromatographic column of 1.6cm × 50cm is selected, MCI GEL CHP 20P solid filler is soaked in methanol and fully stirred to remove bubbles, and after the filler is settled and precipitated, the column is packed by a wet method, wherein the height of the column is about 28cm (about 50ml MCI). About 1.4g of the n-butanol phase obtained in step 2) were dissolved in 5ml of secondary water and wet-loaded. Elution was performed using 10%, 20%, 30%, 40%, 50%, 60%, 70% aqueous methanol solution, respectively (about 5 column volumes per gradient elution). The fraction eluted by 50% methanol water solution is the anti-inflammatory active component (40 mg) of honeysuckle leaves.
And (3) chromatographic analysis: HPLC detection is carried out on a fraction (namely the anti-inflammatory active component of the honeysuckle leaves, which is hereinafter collectively referred to as M1) obtained by eluting 50% methanol water. Use a column of COSMOSIL 5C 18-PAQ (4.6X 250 mm, 5 μm); the mobile phase was 0.5% acetic acid (a) -acetonitrile (B); the flow rate is 1 mL/min; gradient elution: 0-10 min, 12-20% B; 20 percent of B for 10-20 min, 20 percent of B for 20-30 min, and 20 percent of B for 40 percent of B; the detection wavelength is 327 nm; the column temperature was 25 ℃; the amount of sample was 10. mu.L.
HPLC analysis found (see fig. 1): the honeysuckle anti-inflammatory active component (M1) prepared by the method is pure and can be used for further anti-inflammatory activity research experiments.
Example 2
A preparation method of anti-inflammatory active components from honeysuckle leaves comprises the following steps:
1) extracting chemical components of honeysuckle leaves: precisely weighing 10g of dried honeysuckle leaf sample which is sieved by a 60-mesh sieve, placing the dried honeysuckle leaf sample into a Soxhlet extractor, and adding 400ml of petroleum ether to carry out degreasing treatment at 80 ℃ until the solution in the Soxhlet extractor becomes colorless. Defatting, air drying, reflux-extracting with 300ml 80% methanol at 80 deg.C for 3 times (each time for 3 hr), and mixing the 3 extractive solutions to obtain brown viscous crude extract;
2) ultrasonically dissolving the crude extract with secondary water to a suspension state, extracting with n-butanol of the same volume, and concentrating the extract under reduced pressure to obtain n-butanol phase;
3) and (3) column chromatography separation: a chromatographic column of 1.6cm × 50cm and a filler MCI GEL CHP 20P are selected. Elution was performed using 10%, 20%, 30%, 40%, 50%, 60%, and 70% methanol aqueous solutions, respectively. The fraction obtained by eluting with 50% methanol water solution is the anti-inflammatory active component of honeysuckle leaves.
Application test
The anti-inflammatory active component (M1) prepared from honeysuckle leaves in example 1 is used for research and application of anti-inflammatory activity of in vitro enzyme models, macrophage models and mouse foot swelling models.
1. Study of the inhibitory Effect of M1 on 5-LOX
Solution preparation:
buffer solution Tris-HCl: weighing 3.0285g Tris, dissolving with 225mL secondary water, adjusting pH to 7.0 with 1 mol/L hydrochloric acid solution, and metering to 250 mL;
preparation of FOX (dental oxidation-xylenol orange) reagent: 25mL of secondary water and 225mL of methanol were weighed into a 250mL volumetric flask, and 340 mL of the secondary water and the 225mL of methanol were addedμL concentrated sulfuric acid, weighing 24.5mg of ammonium ferrous sulfate hexahydrate and 19mg of xylenol orange, and storing at minus 20 ℃ in a dark place;
preparation of Linoleic Acid (LA): adding 10 into absolute ethyl alcoholμL LA diluted to 15mL, N2Sealing and storing at-20 ℃ under protection to obtain the LA stock solution. Diluting with buffer solution 15 times before use;
preparation of 5-LOX solution: will 10μL zymogen liquid is added to 350μL buffer solution, as an enzyme stock solution. When in use, the enzyme is diluted by 15 times by using a buffer solution to obtain an enzyme diluted solution.
The method comprises the following specific steps: 80 μ L of the enzyme diluted solution was transferred to a 96-well plate, and a gradient of different concentrations of M1 in DMSO 10 was addedμL (blank plus 10)μL DMSO), each concentration is paralleled with six holes, the mixture is evenly mixed by shaking, after the incubation is carried out for 15 min at the temperature of 25 ℃, 10 is added into an enzyme-labeled holeμL-linoleic acid, incubated at 25 ℃ for 10 min, followed by addition of 100μThe FOX reagent is incubated at 25 ℃ for 10 min, and finally the absorbance of the system at 590 nm is determined. Each concentration was paralleled by 6.
The formula for the rate of inhibition of 5-LOX activity is as follows:
inhibition rate = (a)To be measured-ABlank space)/ABlank space
IC50And = concentration of sample to be measured at which inhibition rate reaches 50%.
The inhibition rate was calculated from the inhibition rate formula and plotted for different concentrations of mixture M1 and the corresponding inhibition rates, the results are shown in fig. 2.
The results of fig. 2 show that: m1 has strong inhibitory effect on 5-LOX, and its IC50It was 0.064 mg/mL.
2. Research on anti-inflammatory effect of M1 on mouse macrophage cell line RAW264.7
RAW264.7 cell culture: DMEM medium containing 10% fetal calf serum and penicillin streptomycin mixture (penicillin 10kU/ml, streptomycin 10mg/ml, 100 ×) in 5% CO2Cells were cultured to log phase at 37 ℃.
Observation of the effect of M1 on cell morphology: m1 was dissolved in DMSO and diluted to the desired concentration with DMEM medium so that the DMSO content did not exceed 1 ‰. Then press 6X 105Inoculum size per well, cells were seeded into 6-well plates at 37 ℃ with 5% CO2After 24h of culture under the conditions, the DMEM medium was replaced with new DMEM medium. The experiment was set up for 4 groups, as follows: normal group (no test sample, no LPS); model group (100 ng/ml LPS); experimental group (60 μ M M1+ LPS); negative control group (60 μ M M1). After 2h incubation, 100ng/ml LPS was added to the model and experimental groups, the same volume of PBS was added to the normal and negative control groups, and pictures were taken under the microscope (200X) 22h later, and the results are shown in FIG. 3.
The experimental results of fig. 3 show that: m1 has no obvious effect on normal cells, but can improve the deformation of inflammatory cells, thereby protecting the cells.
Effect of M1 on NO production: RAW264.7 cells were arranged at 3X 104Each well was inoculated in a 96-well plate at 37 ℃ with 5% CO2Culturing under the condition, and replacing with a new DMEM medium after 24 hours. A blank group, a model group, an experimental group (20. mu.M, 40. mu.M, 60. mu. M M1+ LPS) and a negative experimental control group (20. mu. M M1) were set. The test mother liquor was mixed well with fresh DMEM medium and diluted to final concentrations of 20. mu.M, 40. mu.M, and 60. mu.M. After adding the drug, the temperature is 37 ℃ and the CO content is 5 percent2And (3) incubating for 2h, adding LPS into the model group and the experimental group to enable the final concentration to be 100ng/ml, adding PBS with the same volume into the normal group and the negative control group, continuously culturing for 20h, taking 50 mu L of supernatant, reading the absorbance value at 540nm according to the operation instruction of an NO kit, and calculating the amount of NO generated in each hole. Each set of experiments was performed in triplicate. The test results are shown in Table 1.
Table 1 effect of M1 on the release of NO by LPS stimulated RAW 264.7: (
±s，n=6）
As can be seen from table 1: m1 was able to significantly reduce LPS-induced NO release in RAW264.7 and was dose dependent. Thus, M1 is safe for cellular action and has anti-inflammatory effects.
3. M1 research on anti-inflammatory effect of rat foot swelling
First, 32 rats were divided into 4 groups of 8 rats each. The first group was a normal saline as a negative control group, the second group was a dexamethasone positive control group, the N-butanol phase (JYH N-B) of the extracts of the third group was a drug administration group, and the fourth group was a drug administration group of a fraction eluted from 50% methanol aqueous solution of honeysuckle leaves (i.e., anti-inflammatory active fraction of honeysuckle leaves, M1, identified as JYH N-B50% in the following table and fig. 4). Is represented as follows:
after the injection of the corresponding medicine for 1 hour, 0.1 ml of fresh egg white is injected into the right hindpaw of each white rat. Before and 10, 20, 30, 40, 50 and 60 min after injecting egg white, measuring the volume of the right hind paw and calculating the swelling rate thereof, wherein the calculation formula is as follows:
swelling rate = (volume of hindpaw to pro-inflammation)/volume of pro-inflammation.
The results of the effect of each drug on the swelling of the rat feet at different time periods were obtained by processing the experimental data, as shown in fig. 4. From the results of fig. 4, it can be found that: m1 can reduce the swelling rate of the feet of the mice and has obvious anti-inflammatory effect.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (2)
1. The application of the anti-inflammatory active component of honeysuckle leaves in the preparation of anti-inflammatory drugs is characterized in that the anti-inflammatory active component of honeysuckle leaves is prepared by the following steps:
1) defatting pulverized dried folium Lonicerae with petroleum ether, and reflux-extracting with methanol to obtain viscous crude extract;
2) dissolving the viscous crude extract with water for the second time to obtain suspension, extracting with n-butanol, and concentrating under reduced pressure to obtain n-butanol phase;
3) performing column chromatography separation on the n-butanol phase, eluting with 10%, 20%, 30%, 40%, 50%, 60% and 70% methanol water solution, respectively, and selecting 50% methanol water solution to elute to obtain fraction which is the anti-inflammatory active component of folium Lonicerae;
in the step 1), the degreasing treatment specifically comprises the following steps: mixing the crushed dried honeysuckle leaves and petroleum ether according to the ratio of material to liquid of 1 g: mixing 20-60 ml in Soxhlet extractor, and defatting at 70-90 deg.C until the Soxhlet extractor solution turns colorless;
in the step 1), the reflux extraction specifically comprises the following steps: according to the material-liquid ratio of 1 g: adding 70-95% methanol into 10-50 ml, reflux-extracting for 2-5 times, each time for 2-5 h, and combining the extractive solutions to obtain viscous crude extract after reflux-extracting.
2. The use of the anti-inflammatory active fraction from honeysuckle leaves as claimed in claim 1 for the preparation of anti-inflammatory drugs, wherein in step 2) the viscous crude extract is ultrasonically dissolved with secondary water to obtain a suspension, which is extracted with n-butanol at equal volume.
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| CN102267906A (en) * | 2011-06-23 | 2011-12-07 | 湖南长沙远航生物制品有限公司 | Extraction method for chlorogenic acid |
| CN104758340A (en) * | 2015-03-05 | 2015-07-08 | 山东省分析测试中心 | Caffeoylquinic acid extract in Lonicera japonica Thunb leaf, preparation method and application thereof |
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| CN103027937A (en) * | 2012-05-28 | 2013-04-10 | 济宁医学院 | Method for extracting general flavone from honeysuckle leaves |
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| CN104758340A (en) * | 2015-03-05 | 2015-07-08 | 山东省分析测试中心 | Caffeoylquinic acid extract in Lonicera japonica Thunb leaf, preparation method and application thereof |
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