CN103301167B - 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, specifically with Caulis et folium pavettae hongkongensis Lutonaretin for the application of raw material in preparation treatment alcoholic liver injury medicine.
Background technology
The alcoholic liver injury caused of indulging in excessive drinking is the important pathological process of alcoholic liver disease to cirrhosis progress, much research confirms that it still can drive in the wrong direction, therefore effectively treat the good opportunity that alcoholic liver injury is treatment alcoholic liver disease, be again block or delaying chronic alcoholic liver disease to the key of cirrhosis progress.At present, the clinical treatment to alcoholic liver injury does not still have clear and definite scheme and effective medicine.In the last few years, large quantity research showed that natural drug and Chinese medicine showed the feature of reliable curative effect and less untoward reaction in treatment alcoholic liver injury both at home and abroad.Therefore adopt state-of-the-art technology from natural drug and Chinese medicine, develop the new drug for the treatment of alcoholic liver injury significant.
Caulis et folium pavettae hongkongensis (Gypsophila elegans Bieb), has another name called G. paniculata, Caulis et folium pavettae hongkongensis etc., is Caryophyllaceae Gypsophila plant
[1], be that Guangxi Zhuang ethnic mimority area treating hepatic disease commonly uses medical herbs, and one of its main active Caulis et folium pavettae hongkongensis Lutonaretin (isoorientin-2 "-O-α-L-arabinopyranosyl, IOA) report be there is no to the effect of the hepatic injury of ethanol induction.
Summary of the invention
The object of the invention is the novelty teabag researching and developing Chinese medicine Caulis et folium pavettae hongkongensis.
The present invention completes based on the experimentation of inventor.Research point 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 pulverizes, with 75% alcohol reflux 3 times of 80L, merges 3 ethanol extracts, recovery ethanol, obtains ethanol extraction 315.7g.Ethanol extraction adds 630ml distilled water and shakes up into suspension, and then extract successively with petroleum ether, ethyl acetate, n-butyl alcohol respectively, extracting process is summarized as follows: first, uses 630ml petroleum ether extraction, abandons petroleum ether liquid; Then, use 630ml extraction into ethyl acetate, abandon acetic acid ethyl fluid; Finally, use 630ml n-butanol extraction, reclaim n-butyl alcohol, obtain n-butyl alcohol extract 177.6g.
Purification process: D101 type macroporous resin on n-butyl alcohol extract, after first using 5 times amount water elutions, then uses the methanol-eluted fractions of 10 times amount 90%, reclaims methanol, obtains crude extract.Crude extract is dissolved in methanol, with equivalent silica gel mixed sample, is splined on silicagel column, with methanol-acetic acid second fat-water different proportion and 3:3:2; 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 ratio is 4:3:2; 5:3:2; 6:3:2; The fraction of the methanol-acetic acid second fat-water elution of 7:3:2, more similar fraction is again merged after 3 silica gel column chromatographies, reclaim eluant, obtain light brownish crystals 28.3mg.
Two, Caulis et folium pavettae hongkongensis Lutonaretin treatment alcoholic liver injury pharmacodynamic experiment
By Wistar male rat with Chinese liquor induced synthesis alcoholic liver injury animal model, observe the effect of Caulis et folium pavettae hongkongensis Lutonaretin treatment alcoholic liver injury.Result shows that Caulis et folium pavettae hongkongensis Lutonaretin obviously can 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, Caulis et folium pavettae hongkongensis Lutonaretin obviously can reduce hyaluronic acid (HA), laminin，LN (LN), the content of III Collagen Type VI (PCIII) and hydroxyproline (HYP), illustrates that Caulis et folium pavettae hongkongensis Lutonaretin has the effect suppressing collagen deposition.
Shown by pathological examination, normal rats lobules of liver clear in structure, boundary clear between hepatic sinusoid and liver plate, liver cell nuclear is large and justify, and is positioned at the central authorities of cell.There is swelling in model group rats hepatocyte, balloon sample becomes, and endochylema dyeing is uneven, or the anti-cavity of the fat that in endochylema, appearance is differed in size in a large number, or liver focal necrosis and lymphocytic infiltration phenomenon; Caulis et folium pavettae hongkongensis Lutonaretin group rats'liver pathological change is lighter than model group.
Adopt the hepatocellular apoptosis situation of Flow cytometry, RT-PCR checks the expression of bcl-2mRNA, Western blot detects the expression of α-smooth muscle actin (α-SMA) and transforming growth factor-beta 1 (TGF-β 1), result shows, compare with model group, Caulis et folium pavettae hongkongensis Lutonaretin treatment group hepatocellular apoptosis is more obvious, and Caulis et folium pavettae hongkongensis Lutonaretin obviously can suppress the expression of bcl-2mRNA, α-SMA albumen, TGF-β 1 albumen.
In a word, the present invention is studied Caulis et folium pavettae hongkongensis Lutonaretin treatment alcoholic liver injury first, experiment shows, Caulis et folium pavettae hongkongensis Lutonaretin can act on multiple link of alcoholic liver injury or multiple target spot, can effectively react, alleviate hepatic tissue pathology damage, suppress collagen deposition, promote apoptosis on hepatic stellate cells by anti-lipid peroxidation, hepatic injury is obviously alleviated, to control hepatic injury, there is unique advantage.Caulis et folium pavettae hongkongensis Lutonaretin has obvious inhibitory action to the hepatic injury that ethanol causes, and is a kind of new drug having very much potential value for the treatment of alcoholic liver injury.
Detailed description of the invention
One, the preparation of Caulis et folium pavettae hongkongensis Lutonaretin
Extracting method: after dry Caulis et folium pavettae hongkongensis 10kg pulverizes, with 75% alcohol reflux 3 times of 80L, merges 3 ethanol extracts, recovery ethanol, obtains ethanol extraction 315.7g.Ethanol extraction adds 630ml distilled water and shakes up into suspension, and then extract successively with petroleum ether, ethyl acetate, n-butyl alcohol respectively, extracting process is summarized as follows: first, uses 630ml petroleum ether extraction, abandons petroleum ether liquid; Then, use 630ml extraction into ethyl acetate, abandon acetic acid ethyl fluid; Finally, use 630ml n-butanol extraction, reclaim n-butyl alcohol, obtain n-butyl alcohol extract 177.6g.
Purification process: D101 type macroporous resin on n-butyl alcohol extract, after first using 5 times amount water elutions, then uses the methanol-eluted fractions of 10 times amount 90%, reclaims methanol, obtains crude extract.Crude extract is dissolved in methanol, with equivalent silica gel mixed sample, is splined on silicagel column, with methanol-acetic acid second fat-water different proportion and 3:3:2; 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 ratio is 4:3:2; 5:3:2; 6:3:2; The fraction of the methanol-acetic acid second fat-water elution of 7:3:2, more similar fraction is again merged after 3 silica gel column chromatographies, reclaim eluant, obtain light brownish crystals 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') and, 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''').Finally be accredited as: Lutonaretin-2 "-O-α-L-arabinose (isoorientin-2 "-O-α-L-arabinopyranosyl), be called for short 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 process
Wistar male rat 200 ± 20g, 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 25 respectively, 50, the Caulis et folium pavettae hongkongensis Lutonaretin of 100mg/kg), often organizes 15.Except normal group, all the other respectively organize the Chinese liquor that gavage gives dosage escalation, as follows to the method for wine: 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.With it simultaneously, treatment group gavage gives above-mentioned each dosage Caulis et folium pavettae hongkongensis Lutonaretin, and positive controls gives colchicine; Model group and normal group give normal saline; Once a day, continuous 24 weeks.
At the end of administration in 24th week, rat eye is got, and puts to death, takes out liver fast, and a part-80 DEG C of preservations, another part 10% formalin is fixed.
(2) Testing index
1. liver histopathology is observed: routine pathology procuratorial work and electron microscopic observation hepatic tissue ultrastructure;
2. Serum ALT, the vigor of AST, ALP and GGT;
3. the detection of IL-6, TNF-α and MPO;
4. the detection of SOD, GSH-Px and MDA;
5. the detection of HA, PCIII, 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 radially arranges towards periphery centered by central vein, boundary clear between hepatic sinusoid and liver plate, and liver cell nuclear is large and justify, and is positioned at the central authorities of cell.There is swelling in model group rats hepatocyte, balloon sample becomes, and endochylema dyeing is uneven, occurs Malorry corpusculum, or the anti-cavity of the fat that in endochylema, appearance is differed in size in a large number, or liver focal necrosis and lymphocytic infiltration phenomenon.Caulis et folium pavettae hongkongensis Lutonaretin group rats'liver pathological change is lighter than model group.
2. Serum ALT, AST, ALP, GGT are active
Compare with blank group, model group rats serum alt, the trend (P<0.05) that AST, ALP and GGT are increased significantly.Compare with model group, colchicine group, the middle and high dosage group ALT of Lutonaretin, AST, ALP and GGT are active obviously declines (P<0.05).The results are shown in Table 1.
Table 1 Caulis et folium pavettae hongkongensis Lutonaretin to rat blood serum ALT, the impact of AST, ALP, 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 |
| Colchicine group | 189.5±52.4 * | 120.5±36.7 * | 235.2±60.1 * | 4.32±0.83 * |
| Lutonaretin low dose group | 251.8±66.9 | 154.3±40.5 | 276.8±70.5 | 5.89±0.88 |
| Dosage group in Lutonaretin | 220.6±58.4 * | 113.2±32.8 * | 218±61.2 * | 5.26±0.73 * |
| Lutonaretin high dose group | 198.5±50.8 * | 97.8±30.9 * | 202.2±59.7 * | 4.97±0.69 * |
Note: compare with Normal group
Δp<0.05, compares with model control group
*p<0.05.
3. in blood plasma, IL-6, TNF-α and hepatic tissue MPO is active
In model control group rat plasma, IL-6, TNF-α and hepatic tissue MPO is active in Normal group, and colchicine group, Lutonaretin middle and high dosage group then reduces 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 in rat plasma and hepatic tissue MPO
| 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 |
| Colchicine group | 133.5±28.5 * | 23.2±5.2 * | 6.52±0.81 * |
| Lutonaretin low dose group | 146.8±29.6 | 29.5±6.1 | 7.12±0.98 |
| Dosage group in Lutonaretin | 126.4±25.2 * | 22.8±4.1 * | 6.78±0.85 * |
| Lutonaretin high dose group | 117.3±23.8 * | 20.9±3.7 * | 6.19±0.73 * |
Note: compare with Normal group
Δp<0.05, compares with model control group
*p<0.05.
4. hepatic antioxidant and lipid peroxidation
Compare with Normal group, liver SOD, the GSH-Px activity of model group rats all obviously reduce, and MDA activity obviously increases.Lutonaretin each administration group liver SOD, GSH-Px are active significantly strengthens (p<0.05), and MDA activity obviously declines (p<0.05), the results are shown in Table 3.
Table 3 Caulis et folium pavettae hongkongensis Lutonaretin is active to SOD, GSH-Px, MDA in liver tissues of rats
Note: compare with Normal group
Δp<0.05, compares with model control group
*p<0.05.
5. HA, LN, PC III and HYP content in serum
In the serum of model group, HA, LN, PCIII and HYP content all obviously raises, and after administration, all effectively reduces 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 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 |
| Colchicine group | 193.7±64.7 * | 184.2±57.2 * | 138.8±43.2 * | 1.68±0.54 * |
| Lutonaretin low dose group | 218.5±68.3 | 175.8±55.3* | 158.5±46.9 * | 2.03±0.66 * |
| Dosage group in Lutonaretin | 187.2±60.5 * | 167.9±58.6 * | 131.7±43.2 * | 1.79±0.57 * |
| Lutonaretin high dose group | 175.4±58.8 * | 143.2±53.5 * | 125.8±48.1 * | 1.45±0.42 * |
Note: compare with Normal group
Δp<0.05, compares with model control group
*p<0.05.
6. the expression of hepatocellular apoptosis and bcl-2mRNA
By 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 Caulis et folium pavettae hongkongensis Lutonaretin obviously can suppress the expression (p<0.05) of bcl-2mRNA.The results are shown in Table 5.
The apoptosis of table 5 Caulis et folium pavettae hongkongensis Lutonaretin to 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 |
| Colchicine group | 5.23±0.76 * | 63.8±5.9 * |
| Lutonaretin low dose group | 5.19±0.68 | 79.2±7.6 |
| Dosage group in Lutonaretin | 5.47±0.78 * | 67.9±8.1 * |
| Lutonaretin high dose group | 5.86±0.71 * | 63.5±7.4 * |
Note: compare with Normal group
Δp<0.05, compares with model control group
*p<0.05.
7. the expression of α-SMA albumen and TGF-β 1 albumen
Compare with model group, Caulis et folium pavettae hongkongensis Lutonaretin obviously can suppress the expression (p<0.05) of alcoholic liver injury in rats hepatic tissue α-SMA albumen, TGF-β 1 albumen.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 |
| Colchicine group | 1.92±0.58 * | 1.73±0.42 * |
| Lutonaretin low dose group | 2.38±0.62 | 1.93±0.49 |
| Dosage group in Lutonaretin | 2.07±0.55 * | 1.68±0.47 * |
| Lutonaretin high dose group | 1.83±0.59 * | 1.56±0.39 * |
Note: compare with Normal group
Δp<0.05, compares with model control group
*p<0.05.
Claims (1)
1. "-O-α-L-arabinose alleviates the application in the medicine of the collagen deposition caused by ethanol in preparation to Lutonaretin-2.
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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 |
| CN101538297A (en) * | 2009-04-28 | 2009-09-23 | 沈阳药科大学 | Preparation method of high-purity monomer flavone and general flavone contained in capsella bursa-pastoris and application of general flavone |
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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 |
| CN101538297A (en) * | 2009-04-28 | 2009-09-23 | 沈阳药科大学 | Preparation method of high-purity monomer flavone and general flavone contained in capsella bursa-pastoris and application of general flavone |
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| Title |
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| 满天星治疗肝硬化一例疗效观察;尤荣辑;《辽宁中医杂志》;19601231(第3期);9 * |
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