CN102379889B - Application of atemisia gmelinii extract in preparing drugs for preventing liver injuries - Google Patents
Application of atemisia gmelinii extract in preparing drugs for preventing liver injuries Download PDFInfo
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- CN102379889B CN102379889B CN201110244737.4A CN201110244737A CN102379889B CN 102379889 B CN102379889 B CN 102379889B CN 201110244737 A CN201110244737 A CN 201110244737A CN 102379889 B CN102379889 B CN 102379889B
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Abstract
The invention discloses a 2-hydroxyl-6-methoxy acetophenone-4-O-Beta-D-glucoside which is obtained by separating atemisia gmelinii and an application of acetophenone-4-O-Beta-D-glucoside and 6-methoxy-quercitin patuletin-7-O-Beta-D-glucoside in preparing drugs for preventing liver injuries. The active components of the drug of the invention are obtained by extracting and separating the atemisia gmelinii, the source of the active components is wide, and the liver injury curative effects are obvious.
Description
Technical field
The present invention relates to towards the extract of medicine Herba Artemisiae, be specifically related to from the monomeric compound of the separated anti-liver injury obtaining towards medicine Herba Artemisiae.
Background technology
Hepatic injury is the total pathological state a kind of with conspicuous characteristics of multiple hepatic disease, and human health in serious threat.Various harmful factors such as medicine, virus, ethanol, biology etc. may cause liver function to have infringement in various degree, thereby make removing toxic substances, the excretory function of liver and stock with regeneration capacity and reduce, hepatic blood flow reduces, metabolic burden increases the weight of, thereby environment disturbance in occurring, hepatic necrosis and apoptosis, and then cause hepatic injury.The hepatic injury that various harmful factors cause mainly contains the types such as drug induced hepatic injury, viral hepatic injury, alcoholic liver injury, immunologic liver injury, and the whole world has billions of people once or just standing the misery of hepatic injury.The hepatitis B virus of take in the viral hepatic injury cause of disease is example, and the whole world has 2,000,000,000 people to infect hepatitis B virus (HBV), and wherein 3.78 hundred million people change into chronic infection, and 0.5-1.2 hundred million people die from liver cirrhosis, liver failure, hepatocarcinoma etc.Drug induced hepatic injury, alcoholic liver injury patient are countless too.The long-term existence of hepatic injury tends to cause hepatic fibrosis, is and then brings out liver cirrhosis, liver failure, the even important initiating agent of hepatocarcinoma.Therefore prevention and treatment hepatocyte injury are one of important steps of liver disease clinically, are the bases that suppresses the Occurrence and development of diseases such as hepatic fibrosis, hepatic necrosis, fatty liver, cholestasis, liver cirrhosis and hepatocarcinoma.
Treatment and preventing liver injury, do not have particularly preferred way clinically.Therefore at present demand clear and definite to curative effect, anti-liver injury medicament that side effect is low is very strong clinically.Although there is the extract of some Chinese herbal medicine to there is the effect of anti-liver injury in prior art, but from Chinese herbal medicine, extract and obtain the medicative compound monomer of tool and than extract, at least there is the advantage of the following aspects: monomeric compound is more prone to control quality as active component, particularly, for injection, use monomeric compound safer as active component; In extract, active constituent content is conventionally less, and monomeric compound is not limited only to extract in its source during as active component.Therefore, how from Chinese herbal medicine, extract the monomer that obtains having active component is the challenging research in modern Chinese medicine field always.
Summary of the invention
The object of the invention is to prepare a kind of medicine with treatment hepatic injury.In order to realize object of the present invention, the present invention adopts following technical scheme:
The present invention relates to the application of compound 1-3 in preparation treatment liver injury medicament, wherein said compound 1 is 2-hydroxyl-6-methoxyacetophenone-4-O-β-D-Glucose glycosides; Compound 2 is 1-Phenylethanone .-4-O-β-D glucosides; Compound 3 is 6-methoxyl group-quercetagetin-7-O-β-D-Glucose glycosides.
In a preferred embodiment of the present invention, described medicine comprise in compound 1-3 a kind of, two or three as active component.
In an embodiment of the invention, described compound 1-3 be from Herba Artemisiae, extract separated or by the method for chemosynthesis or obtain by extract separation from other Chinese herbal medicine.
In a preferred embodiment of the present invention, described medicine is that described compound and pharmaceutically acceptable medicine are made to pharmaceutically acceptable dosage form, and described dosage form includes but not limited to pill, tablet, capsule, oral liquid, powder, injection.
In a preferred embodiment of the present invention, medicine of the present invention does not comprise the active component of other anti-liver injury except compound 1-3.
In a preferred embodiment of the present invention, medicine of the present invention also comprises other Western medicine active component.
In a preferred embodiment of the present invention, described hepatic injury of the present invention is drug induced hepatic injury, viral hepatic injury, alcoholic liver injury and/or immunologic liver injury.
The active component of the medicine that the present invention obtains is to extract and obtain from Herba Artemisiae, and its wide material sources, have significant curative effect to hepatic injury.
The specific embodiment
1. the separation of monomeric compound
Get in 1500g Herba Artemisiae and add water soaking 3h post-heating 2h, filter and obtain filtrate I, add water and heat 1h again in residue, obtain filtrate II, merging filtrate I and II, obtain Herba Artemisiae water extraction liquid.In pretreated macroporous adsorptive resins, add Herba Artemisiae water extraction liquid, use successively distilled water, 50% ethanol, 95% ethanol elution, collect 50% ethanol elution, concentrated postlyophilization is to dry, by the 50% ethanol elution thing water dissolution of Herba Artemisiae wherein, with dichloromethane, ethyl acetate extraction, obtain dichloromethane extract successively, acetic acid ethyl ester extract and residue water dissolution part.Get and wherein remain water dissolution part and be splined in right amount in pretreated reverse phase silica gel post, methanol-water system gradient elution.Take thin layer chromatography principle as foundation is observed, judgement, and 25% and 50% meoh eluate eluting part is splined on respectively reversed-phase silica gel column chromatography post, sephadex column (Sephadex LH-20) chromatographic column, obtains respectively monomeric compound 1 and 2.By wave spectrum analysis and document, contrast, determine that its chemical constitution is for being respectively 2-hydroxyl-6-methoxyacetophenone-4-O-β-D-Glucose glycosides, and 1-Phenylethanone .-4-O-β-D-Glucose glycosides.
Get acetic acid ethyl ester extract appropriate, with dissolve with methanol, after filtering, wet method is splined on reversed-phase silica gel chromatography post, methanol-water system eluting, wherein a part is splined on polydextran gel (Sephadex LH-20) chromatographic column, methanol-water system repeatedly eluting, obtain a small amount of sample, through preparative high performance liquid chromatography, determine that mobile phase is the methanol-water mixed liquor of 5: 5 again, maintenance column temperature is room temperature, detection wavelength is 254nm, flow velocity is 1ml/min, sample size is 300uL/ time, obtain a monomeric compound 3, by wave spectrum analysis and document, contrast, determine that its chemical constitution is 6-methoxyl group-quercetagetin-7-O-β-D-Glucose glycosides.
Compound 1,2,3 spectral data is as follows respectively:
Compound 1:2-hydroxyl-6-methoxyacetophenone-4-O-β-D-Glucose glycosides
1H-NMR(300MHz，PYRIDINE-d
5)δppm：14.30(1H，s，2-OH)，6.68(1H，d，J＝2.00Hz，H-3)，6.34(1H，d，J＝2.00Hz，H-5)，5.72(1H，d，J＝6.72，m，H-1′)，3.67(3H，s，OCH
3)，2.50(3H，s，COCH
3).
13C-NMR(75MHz，CD
3OD)δppm：107.89(C-1)，163.27(C-2)，96.40(C-3)，164.08(C-4)，91.43(C-5)，166.23(C-6)，99.98(C-1′)，73.31(C-2′)，76.49(C-3′)，69.92(C-4′)，77.04(C-5′)，61.06(C-6′)，203.49(C＝O)，31.81(COCH
3)，54.92(-OCH
3).
Compound 2: 1-Phenylethanone .-4-O-β-D-Glucose glycosides
1H-NMR(300MHz，，D
2O)：7.78(2H，d，J＝8.32Hz，H-2，6)，7.00(2H，d，J＝8.34Hz，H-3，5)，2.42(3H，s，COCH
3)，5.06(1H，d，J＝6.36Hz，H-1′)，3.21-3.82(m-sugar-H)。
13C-NMR(75MHz，，D
2O)：107.7(C-1)，131.11(C-2，6)，116.12(C-3，5)，160.92(C-4)，99.48(C-1′)，72.90(C-2′)，75.58(C-3′)，69.46(C-4′)，76.29(C-5′)，60.61(C-6′)，202.51(C＝O)，26.03(COCH
3)。
Compound 3:6-methoxyl group-quercetagetin-7-O-β-D-Glucose glycosides
1H-NMR(300MHz，(CD
3)
2CO)δppm：12.42(1H，s，5-OH)，6.47(1H，s，8-H)，3.75(3H，s，6-OCH
3)，7.89(1H，d，J＝2.01Hz，2′-H)，6.82(1H，d，J＝8.40Hz，5′-H)，7.46(1H，dd，J＝2.01，8.40Hz，6′-H)，5.12(1H，d，J＝7.26Hz，H-1″)，3.24-3.75(m，sugar-H).
13C-NMR(75MHz，DMSO-d
6)δppm：145.26(C-2)，133.43(C-3)，178.11(C-4)，156.72(C-5)，131.70(C-6)，157.95(C-7)，94.22(C-8)，152.84(C-9)，104.76(C-10)，122.06(C-1′)，116.64(C-2′)，151.98(C-3′)，148.91(C-4′)，115.65(C-5′)，121.67(C-6′)，101.31(C-1″)，74.55(C-2″)，76.96(C-3″)，70.41(C-4″)，78.02(C-5″)，61.45(C-6″)，60.43(-OCH
3).
Compound 1,2,3 structural formula is as follows respectively:
Compound 1:2-hydroxyl-6-methoxyacetophenone-4-O-β-D-Glucose glycosides
Compound 2: 1-Phenylethanone .-4-O-β-D glucoside (picein)
Compound 3:6-methoxyl group-quercetagetin-7-O-β-D-Glucose glycosides
2. three monomeric compounds are to CCl
4
the protective effect of induced mice acute liver damage
2.1 animal grouping and dosages
64 male mice in kunming are divided into 8 groups at random, and 8 every group, grouping and dosage are in Table 1.
2.2 medication
Medicine group is by continuous 5 days gastric infusions of corresponding one day dosage, blank group, model group are with isopyknic distilled water gavage, sooner or later respectively once, within the 5th day, early last administration is after 2 hours, blank group is by body weight lumbar injection 0.1ml/10g normal saline, and all the other groups are pressed 0.1ml/10g lumbar injection 0.1% carbon tetrachloride (CCl
4) soybean oil solution, cause mice CCl
4liver injury model, gives toxic agent carotid artery blood sampling (fasting in first 12 hours of taking a blood sample, can't help water) afterwards in 16 hours, standing 20min, and the centrifugal 15min of 3000r/min, separation of serum, measures ALT, AST activity in mice serum; Get hepatic tissue simultaneously, be placed in-80 ℃ of refrigerator SOD activity to be measured and MDA content.
2.3 liver homogenate preparations
The liver 0.1g thawing is placed in glass homogenizer, adds 0.9ml normal saline to grind in ice bath and makes 10% liver tissue homogenate's liquid, and the centrifugal 15min of 3000r/min, gets supernatant, measures SOD activity and MDA content, and three monomeric compounds are to CCl
4due to hepatic injury mice serum ALT, AST activity the results are shown in Table 1.
Three monomeric compounds of table 1 are to CCl
4due to the impact of hepatic injury mice serum ALT, AST activity
Note: with the comparison of blank group
##p < 0.05,
###p < 0.001; With model group comparison
*p < 0.05,
*p < 0.01,
* *p < 0.001
Table 1 is visible, and experiment mice is to 0.1%CCl
4after soybean oil solution, the ALT of model group, AST activity all obviously raise, and have compared significant difference (P < 0.001, P < 0.05) with blank group, and modeling success is described.With model group comparison, low, the high dose group of 3 monomeric compounds can both obviously reduce serum AST activity (P < 0.05 or P < 0.01).
4.1.1.2 three monomeric compounds are to CCl
4due to the impact of active, the MDA content of hepatic injury murine liver tissue SOD
Table 2CCl
4due to the impact of active, the MDA content of hepatic injury murine liver tissue SOD
Note: with the comparison of blank group
##p < 0.01,
###p < 0.001; With model group comparison
*p < 0.05,
*p < 0.01
Table 2 is visible, obviously reduces (P < 0.001) with blank group comparison model group SOD activities of liver, and MDA content obviously raises (P < 0.01), all has significant difference.With model group comparison, low, the high dose group of three monomeric compounds is increased SOD active (P < 0.05 or P < 0.01) obviously, can both obviously reduce MDA content (P < 0.05 or P < 0.01).
In Herba Artemisiae anti-liver injury effective site, extract as can be seen from Table 1 and Table 2 three monomeric compounds separating and can both effectively suppress hepatic injury.
Should be understood that, for those of ordinary skills, can be improved according to the above description or convert, and all these improvement and conversion all should belong to the protection domain of claims of the present invention.
Claims (2)
1. the application of compound 1-3 in preparation treatment liver injury medicament, wherein said compound 1 is 2-hydroxyl-6-methoxyacetophenone-4-0-β-D-Glucose glycosides; Compound 2 is 1-Phenylethanone .-4-0-β-D glucosides; Compound 3 is 6-methoxyl group-quercetagetin-7-0-β-D-Glucose glycosides, described medicine only comprise in compound 1-3 a kind of, two or three as active component; Described hepatic injury is drug induced hepatic injury or alcoholic liver injury.
2. application according to claim 1, described compound 1-3 be from Herba Artemisiae, extract separated or by the method for chemosynthesis or obtain by extract separation from other Chinese herbal medicine.
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| CN104257715B (en) * | 2014-10-17 | 2018-12-25 | 朴光春 | Herba Artemisiae extract and its preparation method and application |
| CN104844545B (en) * | 2015-04-07 | 2017-09-15 | 王青虎 | A kind of flavone compound and its extraction process |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003089658A (en) * | 2001-09-19 | 2003-03-28 | Noevir Co Ltd | Skin lotion and food excellent in anti-itchiness effectiveness |
| CN101879204A (en) * | 2010-07-05 | 2010-11-10 | 延边大学 | Anticancer effective part of Korean folk medicament Artemisia sacrorum Ledeb. and preparation method thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003089658A (en) * | 2001-09-19 | 2003-03-28 | Noevir Co Ltd | Skin lotion and food excellent in anti-itchiness effectiveness |
| CN101879204A (en) * | 2010-07-05 | 2010-11-10 | 延边大学 | Anticancer effective part of Korean folk medicament Artemisia sacrorum Ledeb. and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| 万年蒿抗肝损伤活性部位研究;李红梅等;《中国优秀硕士学位论文全文数据库》;20101231;E057-49 * |
| 朴光春等.万年蒿提取物对小鼠肝损伤的保护作用.《时珍国医国药》.2007,第18卷(第7期),第1646-1647页. * |
| 李红梅等.万年蒿抗肝损伤活性部位研究.《中国优秀硕士学位论文全文数据库》.2010,E057-49. |
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