CN106266262A - A kind of Callicarpa nudiflora extract with antiinflammatory action - Google Patents
A kind of Callicarpa nudiflora extract with antiinflammatory action Download PDFInfo
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- CN106266262A CN106266262A CN201510306705.0A CN201510306705A CN106266262A CN 106266262 A CN106266262 A CN 106266262A CN 201510306705 A CN201510306705 A CN 201510306705A CN 106266262 A CN106266262 A CN 106266262A
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Abstract
The invention discloses a kind of Callicarpa nudiflora extract with anti-inflammatory activity, described Callicarpa nudiflora extract contains the diterpene-kind compound of phenethyl alcohol glycoside compounds, 15%～27% of 24～the flavone compound of 36%, 0.8%～3%.Gained Callicarpa nudiflora extract of the present invention has stronger anti-inflammatory activity.
Description
Technical field
The present invention relates to field of medicaments, be specifically related to a kind of Callicarpa nudiflora extract with anti-inflammatory activity.
Background technology
Callicarpa nudiflora (Callicarpa nudiflora Hook.et Arn.) is Verenaceae Callicarpa plant, originate from China Hainan,
Guangxi, Guangdong, also there is distribution on the ground such as India, Vietnam, Malaysia, and its root, leaf can be used as medicine, and have astringing to arrest bleeding, antiinflammatory
The effects such as removing toxic substances.The pharmacologically active position of the Callicarpa nudiflora of existing document report mostly is ethanol extract and water extract, and activity mainly includes
Hemostasis, antiinflammatory, enhancing immunity, cytotoxic activity and antibacterial five aspects.But Callicarpa nudiflora different parts becomes with different chemical
Point effect obvious difference, the most fewer to Callicarpa nudiflora composition anti-inflammatory activity research at present, as " Callicarpa nudiflora antiinflammatory action and
Strengthen the experimentation of immunologic function " (Guangdong trace element science, 2006,13 (8): 39-41), Callicarpa nudiflora total flavones
Antiinflammatory, anastalsis research (modern combination of Chinese and Western medicine magazine, 2009,18 (6): 3161-3162), Callicarpa nudiflora 5_ hydroxyl
_ 3_7_3_4_ tetramethoxy flavones antiinflammatory action research (Hainan Medical College's journal, 2014,20 (11): 1460-1462), this kind of
Research or with the crude extract of Callicarpa nudiflora, or the individualized compound separated with Callicarpa nudiflora is as object of study, this
A little prior aries are the most plain for the research of the effective substance of Callicarpa nudiflora antioxidation, and obtain higher anti-
The effective site of scorching activity is also developed into end product and is had very important significance.
Summary of the invention
It is an object of the invention to provide a kind of Callicarpa nudiflora extract with anti-inflammatory activity.
The purpose of the present invention is achieved through the following technical solutions:
A kind of Callicarpa nudiflora extract with antiinflammatory action, it is characterised in that containing 24～the flavone compound of 36%,
The diterpene-kind compound of phenethyl alcohol glycoside compounds, 15%～27% of 0.8%～3%.Described flavone compound contain luteoloside,
Luteolin-4'-O-β-D-pyranglucoside, luteolin-3'-O-β-D-pyranglucoside, luteolin, 5,4'-dihydroxy
-3,7,3'-trimethoxy flavone, 5-hydroxyl-3,7,3', 4'-tetramethoxy flavones therein one or more；Described phenethyl alcohol glycosides chemical combination
Thing contains one or both in verbascoside, Fructus Forsythiae ester glycoside；Described diterpene-kind compound contains Folium Callicarpae Formosanae acid B (callicarpic
Acid B), 7 α-acetyl group sandaracopimaric acid (7 α-acetoxysandaracopimaric acid), sandaracopimaric acid (sandaracopimaric
Acid) one or more in.
The Callicarpa nudiflora extract with antiinflammatory action of the present invention, can be prepared by following steps:
(1) take Callicarpa nudiflora medical material, be ground into coarse powder, add 90-95% alcohol heating reflux and extract 1-3 time, obtain extracting solution,
After filtration, gained filtrate is condensed into extractum A；
(2) step (1) gained extractum A is dispersed in water, is sequentially added into petroleum ether, ethyl acetate extraction, removes molten
Agent, respectively obtains petroleum ether extraction effective site B, Ethyl acetate fraction C；
(3) effective site B is mixed with the ratio that weight ratio is 1～3:1 with effective site C, to obtain final product.Effective site B, C
All with extractum or the dried powder mixing of equal relative density (1.30-1.35,60 DEG C).
As such scheme one of preferably, the preparation method of described step (1) extractum A is: take Callicarpa nudiflora medical material, powder
Being broken into coarse powder, add 95% alcohol heating reflux and extract 3 times, obtain extracting solution, after filtration, gained filtrate reduced in volume obtains extractum (phase
To density 1.30-1.35,60 DEG C).
As such scheme one of preferably, the preparation method of described step (1) extractum A is: take Callicarpa nudiflora medical material, powder
Being broken into coarse powder, add 90-95% alcohol heating reflux and extract 1-3 time, extracting solution filters, and merges, and filtrate is dense to relative density
For the clear paste of 1.04-1.06 (60 DEG C), the chitosan-acetic acid solution of the 1% of addition concentrated solution gross weight 4%-6%, stir evenly, cold
But, standing 16-24 hour, filter, filtrate is concentrated into the clear paste that relative density is 1.06～1.10 (60 DEG C), adds DM-130
Resin, static adsorption 24h, filter, filtrate is concentrated into the extractum of relative density 1.30-1.35 (60 DEG C).
In step described in such scheme (3), effective site B is preferably as 2.5:1 with weight ratio with effective site C.
The compound method of above-mentioned 1% chitosan-acetic acid solution is: takes 1g chitosan and is dissolved in 100ml purified water, adds glacial acetic acid
It is configured to the chitosan solution containing 1% acetate concentration, stands, standby.
Heretofore described extractum is the thick paste of relative density 1.30-1.35 (60 DEG C).
In order to be better understood from the present invention, by the technique effect by the following description of test present invention.
(1) prepared by Callicarpa nudiflora extract
Callicarpa nudiflora medical material 10kg, is ground into coarse powder, extracts with 95% alcohol heating reflux, obtains extracting solution, reduce pressure dense after filtration
Shortening extractum into, extractum is dispersed in water, and successively with appropriate petroleum ether, ethyl acetate and n-butanol extraction, extract is dense
Contracting is dried, obtains petroleum ether, ethyl acetate, n-butyl alcohol and the extract at 4 positions of water, vacuum drying, standby.Comparison
Product verbascoside (1), luteoloside (2), luteolin-3'-O-β-D-pyranglucoside (3), luteolin-4'-O-β-D-
Pyranglucoside (4), luteolin (5), 5,4'-dihydroxy-3,7,3'-trimethoxy flavone (6), 5-hydroxyl-3,7,3', 4'-tetra-
Methoxy flavone (7) is isolated from Callicarpa nudiflora, all carries out structure mirror by NMR, MS and document comparison etc.
Fixed.
(2) nitric oxide (NO) generates inhibitory activity mensuration
Mouse macrophage RAW 264.7 is at 37 DEG C, 5%CO2Incubator in cellar culture in DMEM culture fluid.Real
When testing, cell concentration is adjusted to 3 × 104Be seeded to 96 orifice plates after/mL, adherent after, administration group is separately added into Callicarpa nudiflora extraction
Thing (25 μ g/mL) or control compound (25 μMs) intervene cell 2h, add derivant LPS (final concentration 1 μ g/mL),
Negative control group adds the DMEM culture medium of equivalent, after cultivating 24h, and Aspirate supernatant, add Griess reagent, mix,
Lucifuge stands 10min, measures absorbance at 550nm.
NO generates suppression ratio (%)=(1-administration group NO concentration mean/negative control group NO concentration mean) × 100%.
(3) impact that LPS induction RAW264.7 cell NO is generated by Callicarpa nudiflora extract and compound
As shown in table 1, petroleum ether and the ethyl acetate extract of Callicarpa nudiflora ethanol extract demonstrates swashing under the concentration of 25 μ g/mL
The inhibitory activity that the state RAW 264.7 cell NO that lives discharges, both inhibitory activity are all higher than ethanol extract, wherein ethyl acetate
The inhibitory action at position is slightly stronger than petroleum ether part, and the suppression ratio at n-butanol portion and water position is less than ethanol extract, does not demonstrates
Significantly inhibitory activity.6 flavonoid main constituents of Callicarpa nudiflora demonstrate inhibitory action in various degree under the concentration of 25 μMs,
Wherein luteoloside activity is the highest, next to that luteolin and luteolin-4'-O-β-D-pyranglucoside, 5,4'-dihydroxy
-3,7,3'-trimethoxy flavone is the most weak.
The impact that LPS induction RAW264.7 cell NO is generated by table 1 Callicarpa nudiflora extract and control compound
(4) LC-MS technical appraisement active site main chemical compositions
Petroleum ether and ethyl acetate active site to Callicarpa nudiflora carry out HPLC-DAD-ESI-MS test, its purple of comprehensive analysis
Information and the reference substance Information in Mass Spectras such as outer absorption, relative molecular mass and fragment ion, identify main chromatographic peak and return
Belong to, see accompanying drawing 1.Identify 6 flavone and 1 phenylethanoid glycoside from ethyl acetate extract, identify 2 from petroleum ether part
Individual flavone and 3 Diterpenes, analysis result is shown in Table 2.Composition and the content of ethyl acetate extract is recorded with peak area normalization method
For: luteoloside, luteolin-4'-O-β-D-pyranglucoside, luteolin-3'-O-β-D-pyranglucoside, reseda
Element, 5,4'-dihydroxy-3,7,3'-trimethoxy flavones, 5-hydroxyl-3,7,3', 4'-tetramethoxy flavones is flavones ingredient, and content is
43.8%, verbascoside is phenylethanoid glycoside, and content is 3.5%, and ethyl acetate extract yield is 4.2%；Petroleum ether
The composition at position and content is: 5,4'-dihydroxy-3,7,3'-trimethoxy flavone, 5-hydroxyl-3,7,3', and 4'-tetramethoxy flavones is yellow
Ketones component, content is 20.2%, callicarpic acid B, 7 α-acetoxysandaracopimaric acid, sandaracopimaric
Acid. being Diterpenoids from bulbus, content is 31.9%, and petroleum ether part yield is 1.3%.
The qualification of table 2 Callicarpa nudiflora active site main component
Note: Q is petroleum ether part, and P is ethyl acetate extract.Another callicarpic acid B Chinese translation in the present invention is Folium Callicarpae Formosanae acid B.
Nitric oxide (NO) is to have bioactive gaseous signal molecule, belongs to the important regulatory factor of cell-tocell transmission.
But the excess of NO generates closely related with inflammation.Inflammation-causing substance and inflammatory mediator can induce or increase synthesis and the release of NO.
After using lipopolysaccharide (LPS) to stimulate RAW264.7 macrophage, cellular inflammation model is established, and this process can generate greatly
Amount inducible nitric oxide synthase (induced NO synthase, iNOS), iNOS by being catalyzed its substrate L-arginine,
Generate NO and carry out immunne response.Therefore, suppression NO generation is the direct indicator that compound has anti-inflammatory activity.Experiment finds
Petroleum ether and ethyl acetate extract all can effectively suppress the secretion of NO in the RAW264.7 cell that LPS induces, with ethyl acetate
The antiinflammatory action at position is the strongest.
The chemical composition of Callicarpa nudiflora have flavone and glycoside, triterpene and glycoside, diterpene, phenethyl alcohol glycosides, phenolic acids, steroid,
Volatile oil etc., the most therefrom more than 100 compounds of isolated.But existing to Callicarpa nudiflora composition with activity research
Relatively weak, especially its topmost anti-inflammatory activity, in prior art Callicarpa nudiflora anti-inflammatory activity embodiment or slightly to carry
The activity research of thing (water extract or ethanol extract), or to the isolation identification of individualized compound and activity research, only have
CN104435386A discloses a kind of anti-inflammatory composition, is made up of Callicarpa nudiflora total flavones and total phenylpropanoid.Anti-inflammatory drug is
A kind of medicine that human's demand amount is the biggest, will develop the Callicarpa nudiflora tcm components with genuine characteristic and drug effect characteristic, and one
Aspect improves the activity of its tcm components, on the other hand improves its yield as far as possible.Inventor, on the basis of early-stage Study, resists
Scorching active ingredient group has done in-depth study, by using solvent (water, methanol, ethanol, acetone etc.) to extract, in conjunction with macropore
Resin or activated carbon or ceramic membrane or extraction etc. separation method, combine the analytical technology such as mass spectrum, liquid phase, finally draw the present invention
Technical scheme.
Inventor carries out HPLC-DAD-ESI-MS detection and finds active site, the main one-tenth of Callicarpa nudiflora ethyl acetate extract
Dividing is flavone and flavonoid glycoside composition, and contain a small amount of phenylethanoid glycoside, flavone and Diterpene is then its petroleum ether simultaneously
The main component at position.By the comparison to monomeric compound Yu different activities position, show that the antiinflammatory action of Callicarpa nudiflora is special
The synergistic result of fixed multicomponent, and petroleum ether part and ethyl acetate extract are with the antioxygen of specific ratio gained mixture
Change activity higher, additionally in the later stage is further studied, the Callicarpa nudiflora extract obtained by special process is carried out again
After extract and separate, its anti-inflammatory activity is obviously improved, and this is with chitosan-acetic acid solution and DM-130 resin is by adsorb, be polymerized, sinking
The modes such as shallow lake, separation, by non-active ingredients such as phlegmatic temperament, polysaccharide, pigment in Callicarpa nudiflora crude extract and may be to antiinflammatory action
The composition playing antagonism removes, further enrichment and purification active component, improves the biological activity of unit extract, for follow-up
Material base is established in the research and development of new product.
Beneficial effects of the present invention: (1) obtains the active site that anti-inflammatory activity is stronger, and its main chemical compositions distinct；(2)
Preparation method is easy and simple to handle.
Accompanying drawing explanation
Fig. 1: Callicarpa nudiflora active site (A: petroleum ether component；B: ethyl acetate component) and the HPLC collection of illustrative plates of reference substance (C),
Wherein 1: verbascoside；2: luteoloside；3: luteolin-4'-O-β-D-pyranglucoside；4: luteolin
-3'-O-β-D-pyranglucoside；5: luteolin；6:5,4'-dihydroxy-3,7,3'-trimethoxy flavone；7:5-hydroxyl-3,7,3', 4'-
Tetramethoxy flavones；8:callicarpic acid B；9:7α-acetoxysandaracopimaric acid；10:sandaracopimaric
acid.
Detailed description of the invention
Hereinafter will describe the present invention in detail the most by way of example, inventor by Different Preparation obtain corresponding embodiment with
Comparative example, and record its composition, content, yield, suppression ratio etc. and refer to table 3 below.
Inventor prepares embodiment by following technique:
(1) take Callicarpa nudiflora medical material, be ground into coarse powder, add 90-95% alcohol heating reflux and extract 1-3 time, obtain extracting solution,
After filtration, gained filtrate is condensed into extractum A；
(2) step (1) gained extractum A is dispersed in water, is sequentially added into petroleum ether, ethyl acetate extraction, removes molten
Agent, respectively obtains petroleum ether extraction effective site B, Ethyl acetate fraction C；
(3) effective site B is mixed with the ratio that weight ratio is 1～3:1 with effective site C, to obtain final product.
Wherein the preparation method of step (1) extractum A can also be: takes Callicarpa nudiflora medical material, is ground into coarse powder, adds 90-95%
Alcohol heating reflux extract 1-3 time, extracting solution filter, merging, filtrate dense to relative density be 1.04-1.06 (60 DEG C)
Clear paste, add concentrated solution gross weight 4%-6% 1% chitosan-acetic acid solution, stir evenly, cooling, stand 16-24 hour,
Filtering, filtrate is concentrated into the clear paste that relative density is 1.06～1.10 (60 DEG C), adds DM-130 resin, static adsorption 20-24
H, filters, and filtrate is condensed into extractum.
Method, the most each embodiment effective site composition percentage is analyzed with HPLC-DAD-ESI-MS in above-mentioned summary of the invention
Content records with peak area normalization method, and the impact that LPS induction RAW264.7 cell NO is generated by each embodiment and comparative example is (i.e.
Suppression ratio 1) with Callicarpa nudiflora extract in above-mentioned summary of the invention and compound, LPS induction RAW264.7 cell NO is generated
The experimental technique of impact；The experimental technique of the impact (i.e. suppression ratio 2) of mice auricle swelling is additionally caused also by xylol
As follows:
Male SD rat is randomly divided into by body weight: blank group (respective volume distilled water)；Administration group is (each embodiment, right
Ratio gained sample, dosage 0.8g/kg).Often organize each 10, often group 1 time/d of gastric infusion, continuous 7d, gavage volume 0.2mL/10g
Body weight, after last is administered 30min, is applied to auris dextra two sides by dimethylbenzene, only, left ear compares 30 μ L/.Put to death dynamic after 30min
Thing, cuts ears along auricle baseline.Take off auricle with diameter 8mm card punch at the symmetrical position of left and right ear respectively to weigh, with the right side
It is swelling that auricle heavily deducts the difference of left auricle weight, and calculates ear swelling suppression ratio, inhibitory rate of intumesce (%)=(blank
Organize average ear swelling degree-administration group average ear swelling degree)/blank group average ear swelling degree × 100%.
Table 3
Except experimental group dosage is different, LPS is induced RAW264.7 cell NO with above-described embodiment 1-7 and comparative example 1-15 by method
The impact (i.e. suppression ratio 1) of generation, xylol cause the experimental technique of the impact (i.e. suppression ratio 2) of mice auricle swelling, right
The experimental result of ratio 16-24 such as table 4 below, table 5
Table 4
| Numbering | Preparation method and effective site B, the ratio of C | Dosage | Suppression ratio 1 |
| Comparative example 16 | With comparative example 1 | 50μg/mL | 81.1% |
| Comparative example 17 | With comparative example 2 | 50μg/mL | 78.6% |
| Comparative example 18 | With comparative example 3 | 50μg/mL | 79.3% |
| Comparative example 19 | With comparative example 4 | 50μg/mL | 77.8% |
| Comparative example 20 | With comparative example 6 | 50μg/mL | 81.9% |
| Comparative example 21 | With comparative example 7 | 50μg/mL | 85.1% |
| Comparative example 22 | With comparative example 8 | 50μg/mL | 82.7% |
| Comparative example 23 | With comparative example 9 | 50μg/mL | 85.6% |
| Comparative example 24 | With comparative example 11 | 50μg/mL | 79.2% |
Table 5
| Numbering | Preparation method and effective site B, the ratio of C | Dosage | Suppression ratio 2 |
| Comparative example 16 | With comparative example 1 | 1.6g/kg | 71.6% |
| Comparative example 17 | With comparative example 2 | 1.6g/kg | 70.3% |
| Comparative example 18 | With comparative example 3 | 1.6g/kg | 73.5% |
| Comparative example 19 | With comparative example 4 | 1.6g/kg | 67.8% |
| Comparative example 20 | With comparative example 6 | 1.6g/kg | 73.6% |
| Comparative example 21 | With comparative example 7 | 1.6g/kg | 75.3% |
| Comparative example 22 | With comparative example 8 | 1.6g/kg | 74.7% |
| Comparative example 23 | With comparative example 9 | 1.6g/kg | 78.8% |
| Comparative example 24 | With comparative example 11 | 1.6g/kg | 78.5% |
Claims (8)
1. a Callicarpa nudiflora extract with antiinflammatory action, it is characterised in that containing 24～the flavone compound of 36%, 0.8%～3%
The diterpene-kind compound of phenethyl alcohol glycoside compounds, 15%～27%.
Callicarpa nudiflora extract the most according to claim 1, it is characterised in that described flavone compound contain luteoloside,
Luteolin-4'-O-β-D-pyranglucoside, luteolin-3'-O-β-D-pyranglucoside, luteolin, 5,4'-dihydroxy
-3,7,3'-trimethoxy flavone, 5-hydroxyl-3,7,3', 4'-tetramethoxy flavones therein one or more.
Callicarpa nudiflora extract the most according to claim 1, it is characterised in that described phenethyl alcohol glycoside compounds contains Herba Verbasci Thapsi
One or both in glucosides, Fructus Forsythiae ester glycoside.
Callicarpa nudiflora extract the most according to claim 1, it is characterised in that described diterpene-kind compound contain Folium Callicarpae Formosanae acid B,
One or more in 7 α-acetyl group sandaracopimaric acid, sandaracopimaric acid.
5. Callicarpa nudiflora extract as claimed in claim 1, it is characterised in that prepared by following steps:
(1) take Callicarpa nudiflora medical material, be ground into coarse powder, add 90-95% alcohol heating reflux and extract 1-3 time, obtain extracting solution, mistake
After filter, gained filtrate is condensed into extractum A；
(2) step (1) gained extractum A is dispersed in water, is sequentially added into petroleum ether, ethyl acetate extraction, removes solvent,
Respectively obtain petroleum ether extraction effective site B, Ethyl acetate fraction C；
(3) effective site B is mixed with the ratio that weight ratio is 1～3:1 with effective site C, to obtain final product.
Callicarpa nudiflora extract the most according to claim 5, it is characterised in that the preparation method of described step (1) extractum A
For: take Callicarpa nudiflora medical material, be ground into coarse powder, add 95% alcohol heating reflux and extract 3 times, obtain extracting solution, institute after filtration
Obtain filtrate reduced in volume and obtain extractum A.
Callicarpa nudiflora extract the most according to claim 5, it is characterised in that the preparation method of described step (1) extractum A
For: taking Callicarpa nudiflora medical material, be ground into coarse powder, add 90-95% alcohol heating reflux and extract 1-3 time, extracting solution filters, and closes
And, filtrate is dense to the clear paste that relative density is 1.04-1.06 (60 DEG C), the shell of the 1% of addition concentrated solution gross weight 4%-6%
Polysaccharide acetum, stirs evenly, cooling, stands 16-24 hour, filters, and it is 1.06～1.10 that filtrate is concentrated into relative density
The clear paste of (60 DEG C), adds DM-130 resin, static adsorption 20-24h, filters, and filtrate is condensed into extractum A.
Callicarpa nudiflora extract the most according to claim 5, it is characterised in that in described step (3) effective site B with have
Position C is with weight ratio as 2.5:1 for effect.
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| CN108686045A (en) * | 2018-07-03 | 2018-10-23 | 江西普正制药有限公司 | A kind of callicarpa nudiflora composition and its application for treating pharyngitis |
| CN110721244A (en) * | 2019-11-25 | 2020-01-24 | 黄河科技学院 | Callicarpa nudiflora extract, preparation method and anti-cervicitis application thereof |
| CN111557986A (en) * | 2020-06-11 | 2020-08-21 | 江西普正制药股份有限公司 | Callicarpa nudiflora extract and application thereof in preparation of medicine for treating allergic purpura |
| CN111671827A (en) * | 2020-06-11 | 2020-09-18 | 江西普正制药股份有限公司 | Application of callicarpa nudiflora extract in preparation of ulcerative colitis medicines |
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| CN115501288A (en) * | 2022-09-29 | 2022-12-23 | 山东中医药大学 | Method for extracting callicarpa nudiflora extract and application of extract in resisting H1N1 virus |
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| CN108159195A (en) * | 2018-01-16 | 2018-06-15 | 广西壮族自治区中国科学院广西植物研究所 | A kind of Leaf of Longestapex Beautyberry extract, preparation method and applications |
| CN108159195B (en) * | 2018-01-16 | 2021-02-12 | 广西壮族自治区中国科学院广西植物研究所 | Acer truncatum extract, preparation method and application thereof |
| CN108686045A (en) * | 2018-07-03 | 2018-10-23 | 江西普正制药有限公司 | A kind of callicarpa nudiflora composition and its application for treating pharyngitis |
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| CN111557986A (en) * | 2020-06-11 | 2020-08-21 | 江西普正制药股份有限公司 | Callicarpa nudiflora extract and application thereof in preparation of medicine for treating allergic purpura |
| CN111671827A (en) * | 2020-06-11 | 2020-09-18 | 江西普正制药股份有限公司 | Application of callicarpa nudiflora extract in preparation of ulcerative colitis medicines |
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| CN111557986B (en) * | 2020-06-11 | 2022-01-07 | 江西普正制药股份有限公司 | Callicarpa nudiflora extract and application thereof in preparation of medicine for treating allergic purpura |
| CN111704544A (en) * | 2020-06-30 | 2020-09-25 | 海南师范大学 | Labdane diterpenoid compound and separation method and application thereof |
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| CN115501288B (en) * | 2022-09-29 | 2023-07-04 | 山东中医药大学 | Extraction method of callicarpa nudiflora extract and application of extract in resisting H1N1 virus |
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