CN105816524B - Cortex illicii anti-inflammatory active extract and preparation method and application thereof - Google Patents
Cortex illicii anti-inflammatory active extract and preparation method and application thereof Download PDFInfo
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- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
- A61K2236/333—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones using mixed solvents, e.g. 70% EtOH
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
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Abstract
The invention discloses an anti-inflammatory active extract of anisetree bark and a preparation method and application thereof. The preparation method of the anisetree bark anti-inflammatory active extract is to purify the anisetree bark crude extract according to any one of the following methods a-c to obtain the anisetree bark anti-inflammatory active extract; a: subjecting the crude extract to silica gel column chromatography, eluting with petroleum ether-ethyl acetate, collecting eluate VPetroleum ether：VEthyl acetate5-15: 1, concentrating and drying the eluent to obtain the compound; b: subjecting the crude extract to C18 chromatographic column chromatography, gradient eluting with methanol-water or ethanol-water as eluent, collecting 80-90% ethanol eluate, concentrating, and drying; c: passing the crude extract of cortex Illicii Lanceolati through macroporous resin column, gradient eluting with methanol-water or ethanol-water as eluent, collecting 90-100% ethanol eluate, concentrating, and drying. The extract of the invention has good inhibition effect on inflammation (obviously superior to magnolol).
Description
Technical Field
The invention relates to extraction of active ingredients in plants, in particular to an anti-inflammatory active extract of anisetree bark, a preparation method and application thereof.
Background
Nitric Oxide (NO) is a free radical that functions as both a second messenger and a neurotransmitter and as an effector molecule that mediates the pathological and physiological processes of a variety of diseases such as inflammation and immunity. When immune cells are stimulated by microbial endotoxin, inflammatory mediators and the like, a large amount of Inducible Nitric Oxide Synthase (iNOS) is generated, iNOS catalyzes a substrate L-arginine thereof to generate a large amount of NO for immune response, and excessive NO can cause tissue damage. NO is an important inflammatory factor in both acute and chronic inflammation. A plurality of research results show that the NO level in the synovial fluid and serum of the patients with rheumatism is obviously higher than that of normal people. NO is not only directly involved in rheumatism as an inflammation medium, but also can promote the release of other inflammatory factors, further promote the destruction of articular cartilage and aggravate the disease. Reducing the production of NO may provide protection against joint inflammation.
The strong medicine cortex Illicium difengpi K.I.B et K.I.M dry bark of Illicium difengpi of Illicium genus is a variety recorded in Chinese pharmacopoeia, and has effects of dispelling pathogenic wind, removing dampness, activating qi-flowing and relieving pain. However, no report on the anti-inflammatory active extract of anisetree bark and the preparation method thereof is found so far.
Disclosure of Invention
The invention aims to solve the technical problem of providing an anti-inflammatory active extract of cortex illicii, a preparation method and application thereof.
The preparation method of the anisetree bark anti-inflammatory active extract provided by the invention comprises the following steps:
1) obtaining a crude extract of the anisetree bark;
2) purifying the crude extract of cortex Illici difengpi by any one of the following methods a-c to obtain cortex Illici difengpi anti-inflammatory active extract;
the method a comprises the following steps: subjecting the crude extract to silica gel column chromatography, eluting with petroleum ether-ethyl acetate, collecting eluate VPetroleum ether：VEthyl acetate5-15: 1, concentrating and drying the eluent to obtain the anisetree bark anti-inflammatory active extract;
the method b: subjecting the crude extract to C18 chromatographic column chromatography, gradient eluting with methanol-water or ethanol-water as eluent, collecting 80-90% ethanol eluate, concentrating, and drying to obtain cortex Illicii anti-inflammatory active extract;
the method c comprises the following steps: subjecting the crude extract of cortex Illicii Lanceolati to macroporous resin column chromatography, gradient eluting with methanol-water or ethanol-water as eluent, collecting 90-100% ethanol eluate, concentrating, and drying to obtain cortex Illicii Lanceolati anti-inflammatory active extract.
In step 1) of the above preparation method, the crude extract of anisetree bark can be purchased directly from the market, or can be obtained by extracting anisetree bark according to the conventional method. Preferably, the method comprises the steps of extracting the anisetree bark by using an organic solvent to obtain an anisetree bark crude extract, wherein the organic solvent is chloroform, ethyl acetate, methanol with the volume fraction of 60-100% or ethanol with the volume fraction of 60-100%; the extraction method and times, the amount of organic solvent during extraction and the extraction time are the same as those of the prior art, for example, the extraction method can be leaching, heating extraction, reflux extraction, ultrasonic extraction, and the like, preferably, ultrasonic extraction (the working frequency is preferably 30-100 KHz) is adopted, the ultrasonic extraction time is usually 0.5-2 h, and the amount of the extraction solvent is usually extracted by taking 1Kg of anisetree bark and 2-5L of organic solvent as references.
In the method a of step 2) of the above preparation method, in order to reduce impurities in the crude extract entering the silica gel column, reduce the load on the silica gel column, and increase the content of the active ingredient in the obtained cortex illicii anti-inflammatory active extract, it is preferable to dissolve the crude extract of cortex illicii with water, extract with ethyl acetate, collect the organic phase (ethyl acetate phase), and perform silica gel column chromatography on the collected organic phase. In this method, it is preferable to collect VPetroleum ether：VEthyl acetate10:1 of the eluent.
In the method b of the step 2) of the above preparation method, in order to reduce impurities in the crude extract entering the C18 chromatographic column, reduce the burden of the C18 chromatographic column, and simultaneously increase the content of the active ingredient in the obtained anisetree bark anti-inflammatory active extract, it is preferable to dissolve the anisetree bark crude extract with water, extract with ethyl acetate, collect the organic phase (ethyl acetate phase), and perform C18 chromatographic column chromatography on the collected organic phase. In order to further reduce the burden of the C18 chromatographic column and increase the content of active ingredients in the product, the collected organic phase is preferably decolorized by an MCI chromatographic column and then subjected to C18 chromatographic column chromatography.
In the method c of the step 2) of the above preparation method, the type of the macroporous resin is D101 or HPD 100.
The invention also provides the anisetree bark anti-inflammatory active extract prepared by the method.
The invention further provides an application of the anisetree bark anti-inflammatory active extract prepared by the method in preparing a medicine for treating inflammation, and particularly relates to an application of the anisetree bark anti-inflammatory active extract in preparing a medicine for treating inflammation caused by p-xylene.
Compared with the prior art, the invention obtains the anisetree bark anti-inflammatory active extract containing a plurality of active ingredients by carrying out macroporous resin column chromatography, silica gel column chromatography or C18 column chromatography on the anisetree bark crude extract (wherein the content of magnolol is more than or equal to 25 percent, the content of isoflorid anise alcohol is more than or equal to 5 percent, and an HPLC method), and each active ingredient in the extract has synergistic effect and has good inhibition effect on inflammation (the inhibition effect is obviously better than that of magnolol).
Detailed Description
The present invention will be better understood from the following detailed description of specific examples, which should not be construed as limiting the scope of the present invention.
Example 1
1) Taking 1.5Kg of dried anisetree bark coarse powder, adding 5L of ethanol with the volume fraction of 80%, heating and refluxing for 1h, filtering, repeatedly extracting dregs of a decoction for 2 times, combining extracting solutions, and concentrating under reduced pressure to obtain 182g of anisetree bark crude extract;
2) taking 150g of the crude extract of the anisetree bark, carrying out chromatographic separation and purification by using A C18 column (YMC GEL ODS-A-HG), carrying out gradient elution by using ethanol-water as an eluent, collecting eluent of an ethanol-water solution with the volume fraction of 80%, carrying out reduced pressure concentration and drying to obtain 8.2g of the anti-inflammatory active extract of the anisetree bark, wherein the content of magnolol is 36.8%, and the content of isosafflor octandiol is 6.1%.
Example 2
1) Taking 1.5Kg of dried anisetree bark coarse powder, adding 3L of chloroform for leaching for 18h, filtering, repeatedly extracting the dregs of a decoction for 2 times, combining the extracting solutions, and concentrating under reduced pressure to obtain 28g of anisetree bark crude extract;
2) collecting 20g crude extract of cortex Illicii Lanceolati, separating and purifying with silica gel column chromatography, gradient eluting with petroleum ether-ethyl acetate as eluent, and collecting VPetroleum ether：VEthyl acetateConcentrating under reduced pressure and drying the eluent with the ratio of 10:1 to obtain 3.8g of the anti-inflammatory active extract of the anisetree bark, wherein the content of magnolol is 65.6 percent, and the content of isosafflor octandiol is 20.2 percent.
Example 3
1) Crude extract of anisetree bark was obtained from the same raw materials as in example 1 and by the same method as in example 1;
2) dispersing 150g of the crude extract of the anisetree bark with water, extracting with ethyl acetate, collecting the ethyl acetate part, purifying the ethyl acetate part with macroporous resin D101, performing gradient elution with an ethanol-water system, collecting ethanol eluent with the volume fraction of 85%, performing reduced pressure concentration, and drying to obtain 10.6g of the anti-inflammatory active extract of the anisetree bark, wherein the content of magnolol is 26.2%, and the content of isosafflor octandiol is 5.2%.
Example 4
1) Taking 1.5Kg of dried anisetree bark coarse powder, adding 6L of methanol, performing ultrasonic extraction for 1h, filtering, repeatedly extracting the dregs of a decoction for 1 time, combining the extracting solutions, and concentrating under reduced pressure to obtain 93.5g of anisetree bark crude extract;
2) taking 80g of crude extract of anisetree bark, dispersing with water, extracting with ethyl acetate, collecting ethyl acetate part, carrying out MCI column chromatography on the ethyl acetate part, then carrying out C18 column chromatography separation and purification, using methanol-water as eluent, carrying out gradient elution, collecting eluent of 80-90% methanol-water solution by volume fraction, carrying out reduced pressure concentration and drying to obtain 6.3g of anti-inflammatory active extract of anisetree bark, wherein the content of magnolol is 40.2%, and the content of isosafflor octandiol is 6.6%.
Example 5
1) Taking 1.5Kg of dried anisetree bark coarse powder, adding 7.5L of ethyl acetate, carrying out ultrasonic extraction for 2h, filtering, repeatedly extracting dregs of a decoction for 2 times, combining extracting solutions, and concentrating under reduced pressure to obtain an extract, thus obtaining 60.3g of anisetree bark crude extract;
2) separating and purifying by silica gel column chromatography with 50g of the crude extract of cortex Illicii Lanceolati, gradient eluting with petroleum ether-ethyl acetate as eluent, and collecting VPetroleum ether：VEthyl acetateConcentrating under reduced pressure and drying the eluent at a ratio of 10-15:1 to obtain 4.5g of the anti-inflammatory active extract of the anisetree bark, wherein the content of magnolol is 53.5 percent, and the content of isosafflor octandiol is 17.2 percent.
Example 6
1) Crude extract of cortex illicii difengpi was obtained using the same raw materials and in the same manner as in example 4;
2) separating and purifying 80g of the crude extract of the anisetree bark by using an HPD100 macroporous resin column, performing gradient elution by using a methanol-water system, collecting methanol eluent with the volume fraction of 90%, concentrating under reduced pressure, and drying to obtain 10.1g of the anti-inflammatory active extract of the anisetree bark, wherein the content of magnolol is 25.5%, and the content of isosafflor octandiol is 5.1%.
Test example: pharmacodynamic experimental result of anisetree bark anti-inflammatory active extract
1. Effect of cortex Illicii anti-inflammatory Activity extract and magnolol on LPS-induced production of RAW364.7 macrophage inflammatory factor
And detecting the content of NO in the supernatant of the RAW264.7 macrophage culture medium by adopting a Griess method. The inhibition rate of the anisetree bark anti-inflammatory activity extract and the monomeric compound on the NO production of RAW364.7 cells induced by LPS is examined. The results show that the active extract of anisetree bark (prepared as described in example 1) and its main monomer compounds magnolol and isooctandiol can effectively inhibit the generation of NO, as shown in Table 1.
TABLE 1 anti-inflammatory activity of extract from cortex Illici difengpi and its monomeric compounds for inhibiting NO production of LPS-induced RAW364.7 cells
2. Research on inhibition effect of cortex illicii anti-inflammatory active extract and magnolol on acute inflammatory swelling of mice caused by xylene
70 KM male mice are randomly divided into 7 groups according to body constitution, and a model group (blank control group), a positive control group (western medicine: aspirin; Chinese patent medicine: Pafulin white peony root total glycosides capsule), a high (H), medium (M) and low (L) doses of cortex Illicii difengpi anti-inflammatory activity extract and a magnolol group are arranged. After the administration by intragastric administration for 1 time/d and continuously for 3d and 1h after the last administration, 15 mu L of dimethylbenzene was uniformly coated on the front and back of the right ear of 7 groups of mice respectively by using a liquid-transferring gun, and the left ear was not coated as a control. 1h after smearing, the cervical vertebra is dislocated to kill the mouse, the left ear and the right ear are cut off along the basic line of the auricle, the ear pieces are respectively punched at the same parts of the ears by a 7mm puncher, the ears are weighed, the ear swelling degrees among groups are compared, and the swelling inhibition rate is calculated, and the result is shown in a table 2.
The swelling inhibition rate is (average swelling degree of blank control group-average swelling degree of administration group)/average swelling degree of blank control group × 100%.
The results show that: the high, medium and low dose groups of the anisetree bark anti-inflammatory activity extract have obvious inhibition effect on acute inflammatory swelling of mice caused by xylene. Compared with a blank control group, the high and medium dose groups have obvious difference, and the treatment effect on inflammatory diseases is prompted; in addition, magnolol which is a main component in the active extract of the anisetree bark also plays a role in inhibiting acute inflammatory swelling of mice caused by xylene.
TABLE 2 Effect of cortex Illici difengpi anti-inflammatory active extract and magnolol on ear swelling of mice caused by Paraxylene
P <0.05 compared to model group.
Claims (10)
1. The preparation method of the anisetree bark anti-inflammatory active extract comprises the following steps:
1) obtaining a crude extract of the anisetree bark;
2) purifying the crude extract of cortex Illicii Lanceolati by any one of the following methods a-c to obtain cortex Illicii Lanceolati anti-inflammatory active extract, wherein the main active ingredients in the extract are magnolol and isojatamaritol;
the method a comprises the following steps: subjecting the crude extract to silica gel column chromatography, eluting with petroleum ether-ethyl acetate as eluent, collecting eluate containing V petroleum ether and V ethyl acetate at ratio of 5-15: 1, concentrating, and drying to obtain cortex Illicii anti-inflammatory active extract;
the method b: subjecting the crude extract to C18 chromatographic column chromatography, gradient eluting with methanol-water or ethanol-water as eluent, collecting 80-90% ethanol eluate, concentrating, and drying to obtain cortex Illicii anti-inflammatory active extract;
the method c comprises the following steps: subjecting the crude extract of cortex Illicii Lanceolati to macroporous resin column chromatography, gradient eluting with methanol-water or ethanol-water as eluent, collecting 90-100% ethanol eluate, concentrating, and drying to obtain cortex Illicii Lanceolati anti-inflammatory active extract.
2. The method of claim 1, wherein: in the step 1), an organic solvent is adopted to extract the anisetree bark so as to obtain an anisetree bark crude extract.
3. The method of claim 2, wherein: the organic solvent is chloroform, ethyl acetate, methanol with volume fraction of 60-100% or ethanol with volume fraction of 60-100%.
4. The production method according to any one of claims 1 to 3, characterized in that: in the method a of step 2), V is collectedPetroleum ether∶VEthyl acetateEluent 10: 1.
5. The production method according to any one of claims 1 to 3, characterized in that: in the step 2) of the method a, the crude extract of the anisetree bark is dissolved by water, extracted by ethyl acetate, collected and subjected to silica gel column chromatography.
6. The production method according to any one of claims 1 to 3, characterized in that: in the method b of the step 2), the crude extract of the anisetree bark is dissolved by water, extracted by ethyl acetate, collected and subjected to C18 chromatographic column chromatography.
7. The production method according to any one of claims 1 to 3, characterized in that: in the method b of the step 2), the crude extract of the anisetree bark is firstly decolorized by an MCI chromatographic column before C18 chromatographic column chromatography is carried out.
8. The production method according to any one of claims 1 to 3, characterized in that: in the method c of step 2), the model of the macroporous resin is D101 or HPD 100.
9. An anti-inflammatory active extract of anisetree bark prepared by the method of any one of claims 1 to 8.
10. Use of the anti-inflammatory active extract of anisetree bark as claimed in claim 9 for the preparation of a medicament for the treatment of inflammation.
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| CN101250104A (en) * | 2008-03-19 | 2008-08-27 | 广西师范学院 | Method for extracting high-pure shikimic acid from scarlet octagonal fruit |
| CN102302555A (en) * | 2011-09-21 | 2012-01-04 | 中国人民解放军第二军医大学 | Chinese medicinal extract for treating urarthritis, as well as preparation method and application thereof |
| CN104586937A (en) * | 2013-11-01 | 2015-05-06 | 浙江泰康药业集团有限公司 | Preparation method of illicium plants injection |
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| CN105334273A (en) * | 2015-11-26 | 2016-02-17 | 广西壮族自治区中国科学院广西植物研究所 | Quality control method of anisetree bark |
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| CN101250104A (en) * | 2008-03-19 | 2008-08-27 | 广西师范学院 | Method for extracting high-pure shikimic acid from scarlet octagonal fruit |
| CN102302555A (en) * | 2011-09-21 | 2012-01-04 | 中国人民解放军第二军医大学 | Chinese medicinal extract for treating urarthritis, as well as preparation method and application thereof |
| CN104586937A (en) * | 2013-11-01 | 2015-05-06 | 浙江泰康药业集团有限公司 | Preparation method of illicium plants injection |
| CN104926825A (en) * | 2015-05-07 | 2015-09-23 | 中国人民解放军第二军医大学 | Neolignan alkane derivatives promoting neurotrophic activity, and preparation method and application thereof |
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