CN103301167A - Application of babysbreath isoorientin for preparing medicines for treating alcoholic liver injury - Google Patents
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Abstract
The invention discloses an applicative research of an active ingredient of a traditional Chinese medicine babysbreath isoorientin for preparing medicines for treating alcoholic liver injury. First, the babysbreath isoorientin for treating alcoholic liver injury is researched, and animal experiments show that the for the babysbreath isoorientin can be acted on a plurality of links or targets of alcoholic liver injury, and effectively inhibits lipid peroxidation reaction, alleviates pathological injury of liver tissues, inhibits collagen deposition and accelerates apoptosis of hepatic stellate cells, so that the liver injury is remarkably alleviated. The babysbreath isoorientin has unique advantage to prevent and treat liver injury, and is a very potential novel medicine for treating alcoholic liver injury.
Description
Technical field
The present invention relates to the purposes of Chinese medicine Caulis et folium pavettae hongkongensis extract, the specifically application in preparation treatment alcoholic liver injury medicine take the Caulis et folium pavettae hongkongensis Lutonaretin as raw material.
Background technology
The alcoholic liver injury that excessive drinking causes is that alcoholic liver disease is to the important pathological process of liver cirrhosis development, manyly studies confirm that it still can drive in the wrong direction, therefore effectively the treatment alcoholic liver injury is the good opportunity for the treatment of alcoholic liver disease, is again that blocking-up or delaying chronic alcoholic liver disease are to the key of liver cirrhosis development.At present, clinical treatment to alcoholic liver injury does not still have clear and definite scheme and effective medicine.In the last few years, studies show that in a large number both at home and abroad that natural drug and Chinese medicine were in the characteristics that demonstrated reliable curative effect and less untoward reaction aspect the treatment alcoholic liver injury.Therefore adopt state-of-the-art technology from natural drug and Chinese medicine, to develop the new drug for the treatment of alcoholic liver injury significant.
Caulis et folium pavettae hongkongensis (Gypsophila elegans Bieb) has another name called a Dianthus chinensis, Caulis et folium pavettae hongkongensis etc., is Caryophyllaceae Gypsophila plant
[1], be that Guangxi Zhuang ethnic mimority area treating hepatic disease is commonly used medical herbs, one of its main active Caulis et folium pavettae hongkongensis Lutonaretin (isoorientin-2 " O-α-L-arabinopyranosyl, IOA) there is no report to the effect of the hepatic injury that ethanol is induced.
Summary of the invention
The objective of the invention is to research and develop the new purposes of Chinese medicine Caulis et folium pavettae hongkongensis.
The present invention is based on inventor's experimentation and finishes.Research minute two large divisions:
The preparation of Caulis et folium pavettae hongkongensis Lutonaretin;
The application of Caulis et folium pavettae hongkongensis Lutonaretin in preparation treatment alcoholic liver injury medicine.
One, the preparation of Caulis et folium pavettae hongkongensis Lutonaretin
Extracting method: after dry Caulis et folium pavettae hongkongensis 10kg pulverized, 75% alcohol reflux of usefulness 80L 3 times merged 3 times ethanol extract, and Recycled ethanol obtains ethanol extraction 315.7g.Ethanol extraction adds the 630ml distilled water and shakes up into suspension, then extracts successively with petroleum ether, ethyl acetate, n-butyl alcohol respectively, and extracting process is summarized as follows: at first, use the 630ml petroleum ether extraction, abandon petroleum ether liquid; Then, use the 630ml ethyl acetate extraction, abandon acetic acid ethyl fluid; At last, use the 630ml n-butanol extraction, reclaim n-butyl alcohol, get n-butyl alcohol extract 177.6g.
Purification process: D101 type macroporous resin on the n-butyl alcohol extract, use first 5 times of water gaging eluting after, with 10 times of amount methanol-eluted fractions of 90%, reclaim methanol again, get crude extract.Crude extract being dissolved in methanol, with the equivalent silica gel mixed sample, being splined on silicagel column, is 3:3:2 with methanol-ethyl acetate-water different proportion; 4:3:2; 5:3:2; 6:3:2; 7:3:2; 8:3:2; 9:3:2; 10:3:2 carries out gradient elution.Thin layer chromatography is followed the tracks of, and merges similar fraction.Merging with ratio is 4:3:2; 5:3:2; 6:3:2; The fraction of methanol-ethyl acetate of 7:3:2-water elution merges similar fraction more again behind 3 silica gel column chromatographies, reclaim eluant, gets light brown crystallization 28.3mg.
Two, Caulis et folium pavettae hongkongensis Lutonaretin treatment alcoholic liver injury pharmacodynamic experiment
The Wistar male rat is induced formation alcoholic liver injury animal model with Chinese liquor, observe the effect of Caulis et folium pavettae hongkongensis Lutonaretin treatment alcoholic liver injury.The result shows that the Caulis et folium pavettae hongkongensis Lutonaretin can obviously reduce alanine aminotransferase (ALT), aspartate amino transferase (AST), alkali phosphatase (ALP), paddy acyl transpeptidase (GGT), interleukin-6 (IL-6), human tumor necrosis factor-alpha (TNF-α), the level of hepatic tissue myeloperoxidase (MPO) (MPO) and malonaldehyde (MDA), significantly improve the activity of superoxide dismutase (SOD) and glutathion peroxidase (GSH-Px), prompting Caulis et folium pavettae hongkongensis Lutonaretin has the effect of Anti-lipid peroxidation; In addition, the Caulis et folium pavettae hongkongensis Lutonaretin can obviously reduce hyaluronic acid (HA), laminin，LN (LN), and the content of III Collagen Type VI (PCIII) and hydroxyproline (HYP) illustrates that the Caulis et folium pavettae hongkongensis Lutonaretin has the effect that suppresses collagen deposition.
Show by pathological examination, normal rats lobules of liver clear in structure, boundary clear between hepatic sinusoid and the liver plate, liver cell nuclear is justified greatly, is positioned at the central authorities of cell.Swelling appears in the model group rat hepatocytes, the balloon sample becomes, and endochylema dyeing is uneven, or the anti-cavity of the fat that appearance is differed in size in a large number in the endochylema, or liver focal necrosis and lymphocytic infiltration phenomenon; Caulis et folium pavettae hongkongensis Lutonaretin group rats'liver pathological change is lighter than model model group.
Adopt the hepatocellular apoptosis situation of Flow cytometry, RT-PCR checks the expression of bcl-2mRNA, Western blot detects α-smooth muscle actin (α-SMA) and the expression of transforming growth factor-beta 1 (TGF-β 1), the result shows, compare with model group, Caulis et folium pavettae hongkongensis Lutonaretin treatment group hepatocellular apoptosis is more obvious, and the Caulis et folium pavettae hongkongensis Lutonaretin can obviously suppress bcl-2mRNA, α-SMA albumen, TGF-β 1 protein expression.
In a word, the present invention is studied Caulis et folium pavettae hongkongensis Lutonaretin treatment alcoholic liver injury first, experiment shows, the Caulis et folium pavettae hongkongensis Lutonaretin can act on a plurality of links or a plurality of target spot of alcoholic liver injury, can effectively suppress lipid peroxidation, alleviate the hepatic tissue pathology damage, suppress collagen deposition, promote apoptosis on hepatic stellate cells, hepatic injury is obviously alleviated, the control hepatic injury is had unique advantage.The hepatic injury that the Caulis et folium pavettae hongkongensis Lutonaretin causes ethanol has obvious inhibitory action, is a kind of new drug that potential value is arranged very much for the treatment of alcoholic liver injury.
The specific embodiment
One, the preparation of Caulis et folium pavettae hongkongensis Lutonaretin
Extracting method: after dry Caulis et folium pavettae hongkongensis 10kg pulverized, 75% alcohol reflux of usefulness 80L 3 times merged 3 times ethanol extract, and Recycled ethanol obtains ethanol extraction 315.7g.Ethanol extraction adds the 630ml distilled water and shakes up into suspension, then extracts successively with petroleum ether, ethyl acetate, n-butyl alcohol respectively, and extracting process is summarized as follows: at first, use the 630ml petroleum ether extraction, abandon petroleum ether liquid; Then, use the 630ml ethyl acetate extraction, abandon acetic acid ethyl fluid; At last, use the 630ml n-butanol extraction, reclaim n-butyl alcohol, get n-butyl alcohol extract 177.6g.
Purification process: D101 type macroporous resin on the n-butyl alcohol extract, use first 5 times of water gaging eluting after, with 10 times of amount methanol-eluted fractions of 90%, reclaim methanol again, get crude extract.Crude extract being dissolved in methanol, with the equivalent silica gel mixed sample, being splined on silicagel column, is 3:3:2 with methanol-ethyl acetate-water different proportion; 4:3:2; 5:3:2; 6:3:2; 7:3:2; 8:3:2; 9:3:2; 10:3:2 carries out gradient elution.Thin layer chromatography is followed the tracks of, and merges similar fraction.Merging with ratio is 4:3:2; 5:3:2; 6:3:2; The fraction of methanol-ethyl acetate of 7:3:2-water elution merges similar fraction more again behind 3 silica gel column chromatographies, reclaim eluant, gets light brown crystallization 28.3mg.
Spectral detection data: ESI-MS(m/z): 604[M+Na]
+;
1H NMR(500MHz, CD
3OD) δ: 7.33(1H, s, H-2'), 7.30(1H, d, J=8.0Hz, H-6'), 6.87(1H, d, J=8.0Hz, H-5'), 6.47(1H, s, H-3) and, 6.41(1H, s, H-8), 4.99(1H, d, J=9.5Hz, H-1 "), 4.37(1H, J=5.5Hz, H-1''');
13C NMR(125MHz, CD
3OD) δ: 166.7(C-2), 104.2(C-3), 184.4(C-4), 159.2(C-5), 109.3(C-6), 165.9(C-7), 95.2(C-8), 163.1(C-9), 105.4(C-10), 123.3(C-1'), 114.3(C-2'), 147.1(C-3'), 151.5(C-4'), 117.6(C-5'), 120.6(C-6'), " 73.4(C-1), 82.5(C-2 "), 74.3(C-3 "); 73.5(C-4 "), " 82.9(C-5), 63.4(C-6 "), 107.4(C-1'''), 72.2(C-2'''), 80.8(C-3'''), 69.1(C-4'''), 67.2(C-5''').Be accredited as at last: Lutonaretin-2 " O-α-L-arabinose (isoorientin-2 "-O-α-L-arabinopyranosyl), be called for short the Caulis et folium pavettae hongkongensis Lutonaretin, its molecular formula is C
26O
15H
28, molecular weight is 580.48.
Two, Caulis et folium pavettae hongkongensis Lutonaretin treatment alcoholic liver injury pharmacodynamic experiment
Experimental program:
(1) preparation of experimental animal model, grouping and processing
Wistar male rat 200 ± 20g, the SPF level is divided at random: normal group, model group, positive control drug group (giving colchicine 1.0mg/kg), the basic, normal, high dosage group of Caulis et folium pavettae hongkongensis Lutonaretin (give respectively 25,50, the Caulis et folium pavettae hongkongensis Lutonaretin of 100mg/kg), 15 every group.Except normal group, all the other respectively organize the Chinese liquor that gavage gives dosage escalation, give the method for wine as follows: 5.0g/kg/d, 1 to 4 week; 7.0g/kg/d, 5 to 8 weeks; 9.0g/kg/d, 9 to 12 weeks; 9.5g/kg/d, 13 to 24 weeks.Simultaneously, the treatment group gavage gives above-mentioned each dosage Caulis et folium pavettae hongkongensis Lutonaretin with it, and positive controls gives colchicine; Model group and normal group give the equivalent normal saline; Once a day, continuous 24 weeks.
When the 24th all administrations finished, rat eye was got, and put to death, and took out fast liver ,-80 ℃ of preservations of a part, and another part is fixed with 10% formalin.
(2) detect index
1. liver histopathology is observed: routine pathology procuratorial work and electron microscopic observation hepatic tissue ultrastructure;
2. Serum ALT, AST, the vigor of ALP and GGT;
3. IL-6, the detection of TNF-α and MPO;
4. SOD, the detection of GSH-Px and MDA;
5. HA, PCIII, the detection of LN and HYP;
6. hepatocellular apoptosis detects;
7. RT-PCR detects the expression of bcl-2mRNA;
8. Western blot detects the expression of α-SMA and TGF-β 1.
(3) experimental result:
1. hepatic tissue pathology checks situation
Normal rats lobules of liver clear in structure, liver plate are radial arrangement towards periphery centered by central vein, boundary clear between hepatic sinusoid and the liver plate, and liver cell nuclear is justified greatly, is positioned at the central authorities of cell.Swelling appears in the model group rat hepatocytes, the balloon sample becomes, and endochylema dyeing is uneven, the Malorry corpusculum occurs, or the anti-cavity of the fat that appearance is differed in size in a large number in the endochylema, or liver focal necrosis and lymphocytic infiltration phenomenon.Caulis et folium pavettae hongkongensis Lutonaretin group rats'liver pathological change is lighter than model model group.
2. Serum ALT, AST, ALP, GGT is active
Compare ALT in the model group rat blood serum, AST, the trend that ALP and GGT are increased significantly (P＜0.05) with the blank group.Compare colchicine group, the middle and high dosage group of Lutonaretin ALT, AST, active obviously descend (P＜0.05) of ALP and GGT with model group.The results are shown in Table 1.
Table 1 Caulis et folium pavettae hongkongensis Lutonaretin is to rat blood serum ALT, AST, ALP, the impact of GGT activity
| Group | AST（U/L） | ALT（U/L） | ALP（U/L） | GGT（U/L） |
| Normal group | 98.6±30.1 | 83.9±10.6 | 132.5±35.7 | 2.37±0.67 |
| Model control group | 302.8±71.5 Δ | 172.8±43.2 Δ | 332.6±76.9 Δ | 6.33±0.98 Δ |
| The colchicine group | 189.5±52.4 * | 120.5±36.7 * | 235.2±60.1 * | 4.32±0.83 * |
| The Lutonaretin low dose group | 251.8±66.9 | 154.3±40.5 | 276.8±70.5 | 5.89±0.88 |
| Dosage group in the Lutonaretin | 220.6±58.4 * | 113.2±32.8 * | 218±61.2 * | 5.26±0.73 * |
| The Lutonaretin high dose group | 198.5±50.8 * | 97.8±30.9 * | 202.2±59.7 * | 4.97±0.69 * |
Annotate: compare with Normal group
ΔCompare with model control group p＜0.05
*P＜0.05.
3. IL-6, TNF-α and hepatic tissue MPO are active in the blood plasma
IL-6, TNF-α and hepatic tissue MPO activity are apparently higher than Normal group in the model control group rat plasma, and colchicine group, the middle and high dosage group of Lutonaretin have then reduced the content (p＜0.05) of above three indexs.The results are shown in Table 2.
Table 2 Caulis et folium pavettae hongkongensis Lutonaretin is active to IL-6, TNF-α and hepatic tissue MPO in the rat plasma
| Group | IL-6（pg/ml） | TNF-α（pg/ml） | MPO（μmol/min/mg?protein） |
| Normal group | 86.7±10.1 | 12.6±2.8 | 4.53±0.53 |
| Model control group | 173.9±30.8 Δ | 34.5±6.5 Δ | 7.95±0.97 Δ |
| The colchicine group | 133.5±28.5 * | 23.2±5.2 * | 6.52±0.81 * |
| The Lutonaretin low dose group | 146.8±29.6 | 29.5±6.1 | 7.12±0.98 |
| Dosage group in the Lutonaretin | 126.4±25.2 * | 22.8±4.1 * | 6.78±0.85 * |
| The Lutonaretin high dose group | 117.3±23.8 * | 20.9±3.7 * | 6.19±0.73 * |
Annotate: compare with Normal group
ΔCompare with model control group p＜0.05
*P＜0.05.
4. hepatic antioxidant and lipid peroxidation
Compare with Normal group, the liver SOD of model group rat, GSH-Px activity all obviously reduce, and the MDA activity obviously increases.Active significantly strengthen (p＜0.05) of Lutonaretin each administration group liver SOD, GSH-Px obviously descends (p＜0.05) and MDA is active, the results are shown in Table 3.
Table 3 Caulis et folium pavettae hongkongensis Lutonaretin is to SOD, GSH-Px, MDA activity in the liver tissues of rats
Annotate: compare with Normal group
ΔCompare with model control group p＜0.05
*P＜0.05.
5. HA, LN, PC III and HYP content in the serum
HA, LN, PCIII and HYP content all obviously raise in the serum of model group, after the administration, all effectively reduce the content (p＜0.05) of These parameters, the results are shown in Table 4.
Table 4 Caulis et folium pavettae hongkongensis Lutonaretin is to HA, LN, PCIII, HYP content in the rat blood serum
| Group | HA（μg/L） | LN（μg/L） | PCIII（μg/L） | HYP（mg/g?protein） |
| Normal group | 91.3±22.5 | 97.8±25.4 | 83.5±20.8 | 0.85±0.12 |
| Model control group | 266.9±70.1 Δ | 249.8±58.9 Δ | 198.2±53.7 Δ | 3.12±0.86 Δ |
| The colchicine group | 193.7±64.7 * | 184.2±57.2 * | 138.8±43.2 * | 1.68±0.54 * |
| The Lutonaretin low dose group | 218.5±68.3 | 175.8±55.3* | 158.5±46.9 * | 2.03±0.66 * |
| Dosage group in the Lutonaretin | 187.2±60.5 * | 167.9±58.6 * | 131.7±43.2 * | 1.79±0.57 * |
| The Lutonaretin high dose group | 175.4±58.8 * | 143.2±53.5 * | 125.8±48.1 * | 1.45±0.42 * |
Annotate: compare with Normal group
ΔCompare with model control group p＜0.05
*P＜0.05.
6. the expression of hepatocellular apoptosis and bcl-2mRNA
With the hepatocellular apoptosis situation of Flow cytometry, found that, compare with model group, Caulis et folium pavettae hongkongensis Lutonaretin treatment group hepatocellular apoptosis more obvious (p＜0.05), and the Caulis et folium pavettae hongkongensis Lutonaretin can obviously suppress the expression (p＜0.05) of bcl-2mRNA.The results are shown in Table 5.
Table 5 Caulis et folium pavettae hongkongensis Lutonaretin is to the apoptosis of rat hepatocytes and the expression of bcl-2mRNA
| Group | Rate?of?apoptosis（%） | bcl-2/β-actin?ratio（%） |
| Normal group | 2.27±0.43 | 39.6±6.2 |
| Model control group | 4.86±0.59 Δ | 83.5±9.5 Δ |
| The colchicine group | 5.23±0.76 * | 63.8±5.9 * |
| The Lutonaretin low dose group | 5.19±0.68 | 79.2±7.6 |
| Dosage group in the Lutonaretin | 5.47±0.78 * | 67.9±8.1 * |
| The Lutonaretin high dose group | 5.86±0.71 * | 63.5±7.4 * |
Annotate: compare with Normal group
ΔCompare with model control group p＜0.05
*P＜0.05.
7. α-SMA albumen and TGF-β 1 protein expression
Compare with model group, the Caulis et folium pavettae hongkongensis Lutonaretin can obviously suppress alcoholic liver injury in rats hepatic tissue α-SMA albumen, TGF-β 1 protein expression (p＜0.05).The results are shown in Table 6.
Table 6 Caulis et folium pavettae hongkongensis Lutonaretin is on the impact of rat hepatocytes α-SMA albumen TGF-β 1 protein expression
| Group | α-SMA/β-actin?ratio（%） | TGF-β1/β-actin?ratio（%） |
| Normal group | 0.53±0.07 | 0.97±0.13 |
| Model control group | 2.95±0.63 Δ | 2.35±0.53 Δ |
| The colchicine group | 1.92±0.58 * | 1.73±0.42 * |
| The Lutonaretin low dose group | 2.38±0.62 | 1.93±0.49 |
| Dosage group in the Lutonaretin | 2.07±0.55 * | 1.68±0.47 * |
| The Lutonaretin high dose group | 1.83±0.59 * | 1.56±0.39 * |
Annotate: compare with Normal group
ΔCompare with model control group p＜0.05
*P＜0.05.
Claims (2)
1. the application of Caulis et folium pavettae hongkongensis Lutonaretin in preparation treatment alcoholic liver injury medicine.
Caulis et folium pavettae hongkongensis Lutonaretin according to claim 1 be prepare in accordance with the following methods and:
Extracting method: after dry Caulis et folium pavettae hongkongensis 10 kg pulverized, 75% alcohol reflux of usefulness 80L 3 times merged 3 times ethanol extract, and Recycled ethanol obtains ethanol extraction 315.7g; Ethanol extraction adds the 630ml distilled water and shakes up into suspension, then extracts successively with petroleum ether, ethyl acetate, n-butyl alcohol respectively, and extracting process is summarized as follows: at first, use the 630ml petroleum ether extraction, abandon petroleum ether liquid; Then, use the 630ml ethyl acetate extraction, abandon acetic acid ethyl fluid; At last, use the 630ml n-butanol extraction, reclaim n-butyl alcohol, get n-butyl alcohol extract 177.6 g;
Purification process: D101 type macroporous resin on the n-butyl alcohol extract, use first 5 times of water gaging eluting after, with 10 times of amount methanol-eluted fractions of 90%, reclaim methanol again, get crude extract; Crude extract being dissolved in methanol, with the equivalent silica gel mixed sample, being splined on silicagel column, is 3:3:2 with methanol-ethyl acetate-water different proportion; 4:3:2; 5:3:2; 6:3:2; 7:3:2; 8:3:2; 9:3:2; 10:3:2 carries out gradient elution; Thin layer chromatography is followed the tracks of, and merges similar fraction, and merging with ratio is 4:3:2; 5:3:2; 6:3:2; The fraction of methanol-ethyl acetate of 7:3:2-water elution merges similar fraction more again behind 3 silica gel column chromatographies, reclaim eluant, gets light brown crystallization 28.3 mg.
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Cited By (2)
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| CN105616434A (en) * | 2016-02-17 | 2016-06-01 | 黄权芳 | Application of isoorientin of babysbreath to preparing medicines for treating immunological hepatic fibrosis |
| CN105726528A (en) * | 2016-02-17 | 2016-07-06 | 黄权芳 | Application of babybreath isoorientin to preparation of medicine for treating chemical hepatic fibrosis |
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| CN101301391A (en) * | 2008-05-06 | 2008-11-12 | 张旭明 | Chinese herbal medicine oral liquid cold tea formulation for treating damp-heat viral hepatitis b |
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| CN105616434A (en) * | 2016-02-17 | 2016-06-01 | 黄权芳 | Application of isoorientin of babysbreath to preparing medicines for treating immunological hepatic fibrosis |
| CN105726528A (en) * | 2016-02-17 | 2016-07-06 | 黄权芳 | Application of babybreath isoorientin to preparation of medicine for treating chemical hepatic fibrosis |
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