CN103191102B - The hepatoprotective application of piperic acid - Google Patents
The hepatoprotective application of piperic acid Download PDFInfo
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- CN103191102B CN103191102B CN201310090083.3A CN201310090083A CN103191102B CN 103191102 B CN103191102 B CN 103191102B CN 201310090083 A CN201310090083 A CN 201310090083A CN 103191102 B CN103191102 B CN 103191102B
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Abstract
The invention discloses the application of piperic acid hepatoprotective, also disclose piperic acid application in reducing glutamate pyruvate transaminase (ALT) and the medicine of glutamic oxaloacetic transaminase, GOT (AST) or health product simultaneously.
Description
Technical field
The invention belongs to pharmaceutical technology field, more particularly, it relates to the application of piperic acid hepatoprotective.
Background technology
The existing Patients with Hepatitis B Virus Infection of China about people more than 100,000,000, has chronic hepatitis patient 20,000,000 people, is genuine " hepatitis big country ".The serious diseases such as the existing liver cirrhosis of China, hepatocarcinoma, more than 80% is all to be developed by hepatitis.Coming out owing to there is no the specific medicament of one-time cure hepatitis thoroughly at present, the difficulty for the treatment of hepatitis is relatively big, and its diagnosis and treatment process is doomed to be one very long " Marathon, Battle ", it should taking to put prevention first, treat is auxiliary control strategy.
Black pepper is medicinal and edible plant, is the most conventional food seasoning, records in " Chinese Pharmacopoeia " (version page 227 in 2010) and " China's book on Chinese herbal medicine " (page 287 rolled up by mongolian medicine).Black pepper, English name: FRUCTUSPIPERIS, this product is the dry near ripe of Piperaceae plant Fructus Piperis PipernigrumL. or mature fruit.Autumn Mo gathers when being dirty-green to time spring fruit, dries, for black pepper.Character: black pepper is spherical in shape, diameter 3.5～5mm.Surface pitchy, the tool netted wrinkle of protuberance, there are tiny style vestiges on top, and base portion has the cicatrix come off from fruit axle.Matter is hard, and outer peel is peelable, endocarp canescence or faint yellow.Section yellow-white, mealiness, in have little space.Gas fragrance, acrid in the mouth is peppery.Nature and flavor with return through: pungent, heat.Return stomach, large intestine channel.Function with cure mainly: warming spleen and stomach for dispelling cold, the therapeutic method to keep the adverse QI flowing downwards, expectorant.For gastrofrigid vomiting, stomachache is had loose bowels, inappetence, epilepsy abundant expectoration.
2002 start, Borijihan Geriletu, gold stake, Zhao Ruiguo, Bao Lanlan, Wu Yong, fiber crops spring outstanding person, Han Jingfen etc., Piperaceae plant Fructus Piperis Longi ethanol extraction and derivant thereof have been done substantial amounts of research work, isolate enough piperonyl amide natural materials first: Fructus Piperis Longi quinoline Pipernonaline, C21H27NO3, PPA Piperlonguminine, C16H19NO3With piperine Piperine, C17H19NO3。
Summary of the invention
Through substantial amounts of research, inventor is surprisingly found out that piperic acid has the liver protection function of excellence.
It is an object of the invention to provide the application of piperic acid hepatoprotective.
In the inventive solutions, piperic acid, or GB-H, refer to the compound of having structure:
The invention provides the application in preparing hepatoprotective medicine of a kind of piperic acid.
The invention provides the application in preparation reduces the medicine of serum glutamic pyruvic transminase of a kind of piperic acid.
The invention provides the application in preparation reduces the medicine of glutamic oxaloacetic transaminase, GOT of a kind of piperic acid.
The invention provides the application in preparing hepatoprotective health product of a kind of piperic acid.
The invention provides the application in preparation reduces the health product of serum glutamic pyruvic transminase of a kind of piperic acid.
The invention provides the application in preparation reduces the health product of glutamic oxaloacetic transaminase, GOT of a kind of piperic acid.
The invention provides the application in preparing hepatoprotective medicine of a kind of piperic acid, wherein said medicine, the piperic acid content in its unit dose is 0.5mg-2000mg, more preferably 1mg-1000mg.
In embodiments of the invention, the route of administration of piperic acid of the present invention includes oral administration or parenteral administration.For those of ordinary skills, piperic acid of the present invention can be prepared as oral drug preparation, injection, health food according to prior art, such as, " pharmaceutics " (the 6th edition) according to Cui Defu chief editor, People's Health Publisher, in August, 2007, it is prepared as liquid preparation (such as oral administration solution, injection etc.), solid preparation (tablet, capsule etc.).For those of ordinary skills, the consumption of piperic acid of the present invention every day can be 10mg to 5g, can use once a day, or every day two to three times.
The piperic acid of the present invention can be prepared by the method disclosed in Chinese invention patent ZL20041009611.7: uses ethanol extraction black pepper, its extracting solution reacts with potassium hydroxide, obtain GB-K(i.e. GB-K), the aqueous solution of GB-K reacts with dilute hydrochloric acid and obtains GB-H.This reaction scheme is as follows:
Result of the test of the present invention shows: piperic acid is equal to compare medicine essentiale at reduction serum glutamic pyruvic transminase (ALT), glutamic oxaloacetic transaminase, GOT (AST) aspect, and therefore, piperic acid has reduction serum glutamic pyruvic transminase, reduces glutamic oxaloacetic transaminase, GOT, the purposes of hepatoprotective.
Accompanying drawing explanation
That Fig. 1 represents is the 500MHz of piperic acid1H-NMR spectrum.
That Fig. 2 represents is the 125MHz of piperic acid (GB-H)13C-NMR nmr spectrum.
Fig. 3,5 all represent is that the comparison ■ of each group of rat blood serum ALT value has pole significant difference (P ＜ 0.01) for comparing with model group ● have pole significant difference (P ＜ 0.05) for comparing with model group
Fig. 4,6 all represent is that the comparison ■ of each group of rat blood serum AST value has pole significant difference (P ＜ 0.01) for comparing with model group ● have pole significant difference (P ＜ 0.05) for comparing with model group
Detailed description of the invention
Embodiment 1
The preparation of piperic acid (GB-H)
1. being added in dehydrated alcohol by 100g black pepper, be heated to reflux, reflux, extract, three times at 75 DEG C, the amount and the return time that add dehydrated alcohol be: 300ml, 6h for the first time；200ml, 2h for the second time；100ml, 1h for the third time.
2. merging three black pepper extracting solution, distillation of reducing pressure in 35 DEG C of water-baths concentrates.
3. adding 14.20g potassium hydroxide in concentrated solution, carry out, at 89 DEG C, the 10h that refluxes, then stand cooling 15h, now reactant liquor is yellow.
4. reactant liquor being carried out sucking filtration, the filter cake obtained is exactly the crude product of GB-K.
5. pouring in flask by GB-K crude product, add deionized water 500ml, stirring makes it dissolve, obtains brown yellow solution.
6. brown yellow solution is poured in flask, under stirring state, drip dilute hydrochloric acid (1:1, pH=1～2).
7., during this, brown yellow solution produces green-yellow solid.
8. stand sucking filtration.
9. mixed acid crude product deionized water is cleaned to pH=6～7；
10. sucking filtration, filter cake carries out drying 24 hours in baking oven.
11. obtain green-yellow mixed acid powder, i.e. piperic acid (GB-H).
Molecular formula C of GB-H12H9KO4, ESI-MSm/z:217.0 [M-K]-.Concrete reaction condition is as follows:
Embodiment 2
The structure of piperic acid (GB-H) determines
Use 500MHz Brooker nuclear magnetic resonance analyser, make solvent with deuterated water, measure the 500MHz of piperic acid1H-NMR spectrum (see figure 1) and piperic acid (GB-H) 125MHz13C-NMR nmr spectrum (see figure 2).
Piperic acid1H-NMR spectrum chemical shift data table, unit ppm
| The hydrogen atom numbering of GB-H | Chemical shift, ppm |
| H-2 | 5.923,5.953 |
| H-3 | 7.341,7.335,7.321,7.311,7.306,7.296 |
| H-4 | 6.945,6.939,6.923 |
| H-5 | 6.976,6.971 |
| H-7 | 7.023,7.020,7.007,7.004 |
| H-10 | 6.986 |
| H-11 | 7.245,7.243 |
| H-12 | 12.251 |
Piperic acid13C-NMR spectrogram chemical shift data table, unit ppm
Embodiment 3
Piperic acid hepatoprotective preventive experiment
1. laboratory animal and material
Laboratory animal:Two grades of male Wistar rats, body weight 180 ± 10g, credit number: SCXK(capital) 2006-2009, rank SPF/AF, Beijing dimension tonneau China Experimental Animal Center provide.
Experiment reagent:
Piperic acid is by University of the Inner Mongol's polymer chemistry and 1 preparation according to embodiments of the present invention of mongolian medicine institute；
ALT, AST test kit is produced by Zhongsheng Beikong Biological Science & Technology Co., Ltd.；
Essentiale (essentiale, EssentialeForte): Sanofi-Aventis (Beijing) pharmaceutical Co. Ltd produces；
Experimental apparatus: it is reinforced that Italy produces PRONTOEVOLUTION(Pentium) automatic clinical chemistry analyzer；
TDL-5-A centrifuge (upper marine products)；
The preparation of high lipid food:
Cholesterol 3%, Adeps Sus domestica 10%, sodium cholate 0.5%,
Normal feedstuff 86.5%(formula: flour 20%, rice flour 10%, Semen Maydis 20%, wheat bran 25%, bean material 20%, bone meal 2%, fish flour 2%, Sal 0.9%, vitamin 0.1%)
2 test methods
Packet and administration:Extracting male Wistar rat 60, body weight 180 ± 10g, after (room temperature 20～24 DEG C, humidity 50%～60% are freely drunk water) feed 3 days under experimental situation before experiment, it is randomly divided into 6 groups by body weight, often group 10,1 group is blank group；2 groups is hepatitis model group；3 groups is positive control (essentiale) group；4 groups is piperic acid high dose group；5 groups is dosage group in piperic acid；6 groups is piperic acid low dose group；In the 4th day, in addition to blank group, remaining respectively organizes every morning with 52 degree of Chinese liquor gavages (7ml/kg), every afternoon, 5:30 gavage gave by reagent and positive controls medicine (0.4mL/100g), gavage 5 weeks continuously, before being given daily, rat is carried out body weight determination, hepatitis model group and the 0.5%CMC-Na of blank group gavage same volume.Packet situation and each group dosage are shown in Table 1.
Measure and observational technique: continue to be administered to the 35th day, took blood in the 36th day from femoral artery, centrifugal, separate serum and supply to measure the biochemical indicators such as ALT, AST, the data obtained is carried out statistical procedures, represents with mean ± standard deviation, the significance of difference judges with T inspection.
3 result of the tests:
Experimental result lists table 1,2,3,4,5 in, result diagram such as Fig. 3,4.
Table 1 is grouped situation and respectively organizes dosage
Rat ALT assay result (unit U/L) of the 35th day after table 2 administration
Each comparison (see figure 3) organizing rat blood serum ALT value
The impact (means standard deviation) of rat blood serum ALT is analyzed (U/L) by table 3
| Group | Animal number of cases (only) | ALT | P value |
| Blank group | 10 | 43.75±6.55 | **1.1×10-10 |
| Hepatitis model group | 10 | 151.93±26.31 | |
| Essentiale group | 10 | 106.56±16.42 | **6.6×10-5 |
| High dose group | 10 | 108.43±19.55 | **0.0002 |
| Middle dosage group | 10 | 116.42±29.43 | **0.0047 |
| Low dose group | 10 | 127.41±28.55 | *0.0285 |
P value refers to that each group is compared with matched group: * P ＜ 0.05, there were significant differences；* P ＜ 0.01, has pole significant difference.
35th day rat AST assay result (unit U/L) after table 4 administration
Each comparison (see figure 4) organizing rat blood serum AST value
The impact (means standard deviation) of rat serum AST is analyzed (U/L) by table 5
| Group | Animal number of cases (only) | AST | P value |
| Blank group | 10 | 166.28±16.68 | **1.6×10-11 |
| Hepatitis model group | 10 | 449.33±45.44 | |
| Essentiale group | 10 | 294.44±72.12 | **4.4×10-5 |
| High dose group | 10 | 301.08±77.52 | **0.00013 |
| Middle dosage group | 10 | 315.31±70.52 | **0.00020 |
| Low dose group | 10 | 345.41±101.60 | *0.01163 |
P value refers to that each group is compared with matched group: * P ＜ 0.05, there were significant differences；* P ＜ 0.01, has pole significant difference.
4, analyze
Result above shows, hepatitis model group compares with blank group, and AST, ALT value raises, and two groups are compared and have pole significant difference, illustrate that modeling is successfully.Each group comparison model group has certain fall AST, ALT effect.The above results demonstrates piperic acid and has the effect reducing AST, ALT.
Embodiment 4
Piperic acid treatment fatty liver experiment
1 laboratory animal and material
Laboratory animal:Two grades of male Wistar rats, body weight 170 ± 10g, credit number: SCXK(capital) 2006-2009, rank SPF/AF, Beijing dimension tonneau China Experimental Animal Center provide.
Experiment reagent:
Piperic acid is prepared according to embodiment 1 by University of the Inner Mongol's polymer chemistry and mongolian medicine institute；
ALT, AST test kit is produced by Zhongsheng Beikong Biological Science & Technology Co., Ltd.；
Essentiale: Sanofi-Aventis (Beijing) pharmaceutical Co. Ltd produces；
Experimental apparatus: it is reinforced that Italy produces PRONTOEVOLUTION(Pentium) automatic clinical chemistry analyzer；
TDL-5-A centrifuge (upper marine products)；
The preparation of high lipid food:
Cholesterol 3%, Adeps Sus domestica 10%, sodium cholate 0.5%,
Normal feedstuff 86.5%(formula: flour 20%, rice flour 10%, Semen Maydis 20%, wheat bran 25%, bean material 20%, bone meal 2%, fish flour 2%, Sal 0.9%, vitamin 0.1%)
2 test methods
Packet and administration:Extracting male Wistar rat 90, body weight 170 ± 10g, front (room temperature 20～24 DEG C under experimental situation of experiment, humidity 50%～60%, freely drinks water) feed 3 days after, in the 4th day, 15 Mus are stayed to feed normal diet for blank group, remaining Mus feeds high lipid food every day, morning with 52 degree of Chinese liquor gavages (7ml/kg), every afternoon the continuous gavage of 5:30 4 weeks.Weighing for each group, eye socket takes blood, measures ALT, is shown in Table 6.Blank group eliminates 5.Model group eliminates 25 rats too high or too low for ALT, is randomly divided into 5 groups by ALT level and is shown in Table 7, often group 10, respectively alcoholic fatty liver hepatitis model group；Positive control (essentiale) group；Piperic acid high dose group；Dosage group in piperic acid；Piperic acid low dose group.Gavage gives by reagent and positive controls medicine (0.4mL/100g), model group and the 0.5%CMC-Na of blank group gavage same volume.Packet situation and each group dosage are shown in Table 8.
Measure and observational technique: continue to be administered 2 weeks, took blood in the 15th day from femoral artery, centrifugal, separate serum and supply to measure the biochemical indicators such as ALT, AST, the data obtained is carried out statistical procedures, represents with mean ± standard deviation, the significance of difference judges with T inspection.
3 result of the tests:
Experimental result lists table 6,7,8,9,10,11,12 in, result diagram such as Fig. 5,6.
Rat ALT assay result (unit U/L) of table 6 4W
Note: the data of red italic discard.
Table 7 removes the too high or too low rat of ALT with ALT horizontal random packet situation (unit U/L)
Table 8 is grouped situation and respectively organizes dosage
Rat ALT assay result (unit U/L) of the 15th day after table 9 administration
Each comparison (see figure 5) organizing rat blood serum ALT value
The impact (means standard deviation) of rat blood serum ALT is analyzed (U/L) by table 10
| Group | Animal number of cases (only) | ALT | P value |
| Blank group | 10 | 55.73±8.99 | **5.6×10-14 |
| Hepatitis model group | 10 | 174.29±19.26 | |
| Essentiale group | 10 | 140.05±9.11 | **8.8×10-6 |
| High dose group | 10 | 144.47±12.82 | **0.0002 |
| Middle dosage group | 10 | 150.80±15.93 | **0.0032 |
| Low dose group | 10 | 147.33±15.83 | **0.0011 |
P value refers to that each group is compared with matched group: * P ＜ 0.05, there were significant differences；* P ＜ 0.01, has pole significant difference.
15th day rat AST assay result (unit U/L) after table 11 administration
Each comparison (see figure 6) organizing rat blood serum AST value
The impact (means standard deviation) of rat serum AST is analyzed (U/L) by table 12
| Group | Animal number of cases (only) | AST | P value |
| Blank group | 10 | 172.05±12.41 | **2.7×10-10 |
| Hepatitis model group | 10 | 561.92±101.90 | |
| Essentiale group | 10 | 408.11±84.10 | **0.0018 |
| High dose group | 10 | 427.76±99.93 | **0.0071 |
| Middle dosage group | 10 | 449.73±79.72 | *0.0116 |
| Low dose group | 10 | 520.36±101.8 | 0.3632 |
P value refers to that each group is compared with matched group: * P ＜ 0.05, there were significant differences；* P ＜ 0.01, has pole significant difference.
4, analyze
Serum ALT, AST activity raise substantially, can be as the Main Diagnosis index of acute stage liver function injury, and result above shows, alcoholic fatty liver hepatitis model group compares with blank group, AST, ALT value raises, and two groups are compared and have pole significant difference, illustrate that modeling is successfully.Each group comparison model group has certain fall AST, ALT effect.Except piperic acid low dose group to AST item without significance in addition to, remaining respectively organizes comparison model group has significance to reduce.
Result of the test and conclusion
Reducing in terms of glutamate pyruvate transaminase, test result indicate that GB-H group, alcoholic fatty liver hepatitis model group compares with blank group pole significant difference.GB-H therapeutic effect is more significantly.
Reducing in terms of glutamic oxaloacetic transaminase, GOT, GB-H group, alcoholic fatty liver hepatitis model group compares with blank group pole significant difference.It is fairly obvious that GB-H treats high glutamic oxaloacetic transaminase, GOT effect.
In a word, GB-H has liver protection function.
Claims (3)
1. piperic acid application in preparing hepatoprotective medicine, here, described hepatoprotective refers to reduce serum glutamic pyruvic transminase and reduce glutamic oxaloacetic transaminase, GOT；And described hepatoprotective is treatment alcoholic fatty liver hepatitis.
Applying the most as claimed in claim 1, wherein, described medicine, in its unit dose, the content of piperic acid is 0.5mg-2000mg.
Applying the most as claimed in claim 2, wherein, described medicine, in its unit dose, the content of piperic acid is 1mg-1000mg.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1634030A (en) * | 2004-12-03 | 2005-07-06 | 内蒙古大学 | Use of piperic acid ester compound in preparation of drug or healthcare product for reducing blood fat |
| CN1795851A (en) * | 2004-12-03 | 2006-07-05 | 内蒙古大学 | Application of compound of esters of piperic acid in preparing hypolipidemic or health products |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1634030A (en) * | 2004-12-03 | 2005-07-06 | 内蒙古大学 | Use of piperic acid ester compound in preparation of drug or healthcare product for reducing blood fat |
| CN1795851A (en) * | 2004-12-03 | 2006-07-05 | 内蒙古大学 | Application of compound of esters of piperic acid in preparing hypolipidemic or health products |
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