CN109045035A - Application of 7- (2,2- dimethyl -3- crotonoyl the amido)-octahydro benzene quinoline acetic acid esters in preparation treatment liver disease drug - Google Patents

Application of 7- (2,2- dimethyl -3- crotonoyl the amido)-octahydro benzene quinoline acetic acid esters in preparation treatment liver disease drug Download PDF

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Publication number
CN109045035A
CN109045035A CN201810793903.8A CN201810793903A CN109045035A CN 109045035 A CN109045035 A CN 109045035A CN 201810793903 A CN201810793903 A CN 201810793903A CN 109045035 A CN109045035 A CN 109045035A
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dimethyl
octahydro
acid esters
drug
acetic acid
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CN201810793903.8A
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CN109045035B (en
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玉万国
陈云芳
何云
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Guangxi University of Science and Technology
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Guangxi University of Science and Technology
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/473—Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics

Abstract

The invention belongs to the purposes technical fields of monomeric compound, and in particular to purposes of 7- (2,2- dimethyl -3- crotonoyl the amido)-octahydro benzene quinoline acetic acid esters in the drug, food or health care product that preparation treats or prevents hepar damnification.Research discovery through the invention; 7- (2; 2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters in vitro liver cell damage have significant protective effect; it can be used for preparing the drug, food or health care product of liver protecting, it may also be used for prepare drug, food or the health care product of hepatocellular injury protection；There is significant repair to internal liver organization organ damage, can be used for preparing drug, food or the health care product for treating or preventing liver diseases, be suitable for large-scale promotion, there is wide development and application prospect.

Description

7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters is controlled in preparation Treat the application of liver disease drug
Technical field
The invention belongs to the purposes technical fields of monomeric compound, and in particular to a kind of 7- (2,2- dimethyl -3- crotonoyls Amido) the purposes of-octahydro benzene quinoline acetic acid esters in preparation treatment liver disease drug.
Background technique
Liver is metabolic organ important in human body, removing toxic substances organ, digestive organs and immune defense organ, is had complicated more The biochemical functions of sample are the hinges of human metabolism.Hepatopathy is the acute and chronic lesion occurred in liver, is a kind of To the highly harmful disease of body.Common hepatopathy includes: alcoholic liver, fatty liver, virus hepatitis, cirrhosis, hepatapostema It is that liver cancer genesis and development keeps the reason plain Deng, all kinds of hepatopathys.Various liver diseases disease incidence are in the trend of cumulative year after year in recent years, Protect liver health by public concern.
Clinical common hepatopathy majority belongs to chronic disease, and treatment cycle is long, and there are repeatabilities, needs Long-term taking medicine.With The continuous development of modern science and technology, reduce treatment liver diseases chemical synthetic drug research and development and market periods, but Due to clinical liver disease diversity and pathomechanism complexity, chemical synthetic drug is also easy to produce drug resistance, drug failure and the secondary work of poison It is negatively affected with equal.Chinese medicine native compound is curative for effect, abundance, no obvious toxic-side effects, and short treating period is quick to be not easy Generate drug tolerance.Currently, it is less by the liver protecting drug that Chinese medicine natural monomers compound is prepared, find exploitation one Kind liver protection Chinese medicinal compound, has broad application prospects.
7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters, i.e. 7- (2,2- dimethyl -3- crotonoyls Amido) -2,4- dimethyl -5- oxo -1,2,3,4,4a, 5,6,10b- octahydro benzo [f] -1- quinolyls-acetic acid esters, [7- (2, 2-dimethylbut-3-enamido)-2,4-dimethyl-5-oxo-1,2,3,4,4a,5,6,10b-octahydrobenzo [f] quinolin-1-yl acetate, DQA], molecular formula C23H30N2O4, relative molecular weight 398, molecular structure is as follows It is shown.Separation preparation is mainly extracted from medicinal plant Rhizophora stylosa aerial root endophyte.
It there is no 7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters in terms of liver protecting at present Correlative study report.
Summary of the invention
Present invention aim to address above-mentioned the problems of the prior art, provide a kind of 7- (2,2- dimethyl -3- crotonoyls Amido) the purposes of-octahydro benzene quinoline acetic acid esters in preparation treatment liver disease drug.7- (2,2- dimethyl -3- crotonoyl amido) - Octahydro benzene quinoline acetic acid esters in vitro liver cell damage have significant protective effect, can be used for preparing liver protecting drug, Food or health care product；There is significant repair to internal liver organization organ damage, can be used for preparing treatment or prevention liver Drug, food or the health care product of dirty disease are suitable for large-scale promotion, have wide development and application prospect.
To achieve the goals above, beneficial effects of the present invention are specific as follows:
1, the present invention passes through the study found that 7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters is to Vitro hepatic Cellular damage has significant protective effect, can significantly reduce ALT value, can be used for preparing the drug of liver protecting, food or Health care product, it may also be used for prepare drug, food or the health care product of hepatocellular injury protection；
2, the present invention passes through the study found that 7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters is to internal liver Dirty injuries of tissues and organs has significant repair, can significantly reduce ALT and AST value, improves liver organization lesion, can use Drug, food or the health care product of liver diseases are treated or prevented in preparation.
Detailed description of the invention
Fig. 1 is 7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters to CCl4Inducing mouse Acute Hepatic Dirty damage histopathologic slide schemes, wherein A: Normal group；B:CCl4Model control group；C: bifendate positive controls； D:DQA high dose group；E:DQA middle dose group；F:DQA low dose group.
Specific embodiment
In order to be more clearly understood that technology contents of the invention, spy lifts following embodiment and is described in detail.
1 7- of embodiment (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters, i.e. 7- (2,2- diformazans Base -3- crotonoyl amido) -2,4- dimethyl -5- oxo -1,2,3,4,4a, 5,6,10b- octahydro benzo [f] -1- quinolyl-second Acid esters is to CCl4Induce the protective effect experiment of acute hepatocellular injury.
Reagent and drug:
Bifendate (BDP) (Beijing XieHe medicine Factory)；ALT(glutamic-pyruvic transaminase) (biotechnology is built up in Nanjing to be had detection kit Limit company)；CCl4(western Gansu Province science limited liability company, analysis are pure)；(western Gansu Province science limited liability company divides dimethyl sulfoxide It analyses pure)；DQA, i.e. 7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters, it is red from medicinal plant by laboratory Isolated, purity > 98% (HPLC) is extracted in extra large olive aerial root endophyte.
Experimental method and result:
1. hepatocyte cultures
Male mice in kunming is taken, for 24 hours, bloodletting of breaking end, sterile separation liver weighs, uses PBS buffer solution irrigation for fasting Liver is to canescence.Liver is cut into tissue pieces, is gently ground using glass tissue homogenizer, PBS buffer solution is added, 1000rpm is centrifuged 5min, removes supernatant, and 10mL cell culture fluid is added, hepatocyte suspension is made.
2. establishing CCl4Inducing hepatocyte damage model
It takes the 50 above-mentioned hepatocyte suspensions of μ L to be inoculated in 96 orifice plates, 30 μ L cell culture fluids is added in each hole, with dimethyl Asia Sulfone is cosolvent, is separately added into various concentration CCl4(1 ~ 16 mmol/L) controls the final concentration of 0.1%(body of dimethyl sulfoxide Fraction), 37 DEG C of conditions induce 1h, 2h, 3h, 4h respectively, and the supernatant collected in 96 orifice plates detects ALT value.It is tied according to detection Fruit draws CCl4The dose-effect and Time-activity-curve of inducing hepatocyte damage select optimal damage concentration and trauma time to establish liver thin Cellular damage model.
3. DQA is to CCl4The protective effect of inducing hepatocyte damage
Above-mentioned hepatocyte suspension is taken, Normal group, CCl are set as4Model control group, BDP positive controls, difference DQA give Pharmaceutical quantities group, 5 parallel holes of every group of setting.CCl44mmol/L CCl is added in model group and dosage group4, while to medicament The DQA drug of various concentration is added in amount group.It is incubated for 3h, 2000rpm refrigerated centrifuge 5min under the conditions of 37 DEG C, collects on liver cell Clear liquid detects ALT value.As a result as follows:
Compared with Normal group: ### indicates P < 0.001；With CCl4Model control group compares: * * indicates P < 0.01, * * * Indicate P < 0.001.
Table 1 the result shows that, external CCl4The activity of ALT is significant after inducing hepatocyte damage, in cell supernatant increases, and adds Enter the experimental group of various dose DQA, ALT value and CCl in supernatant4Model control group compares, and different dosing dosage occurs The phenomenon that reducing ALT value, it is best that high dose group reduces ALT value effect.The above results explanation, 7- (2,2- dimethyl -3- crotonoyls Amido)-octahydro benzene quinoline acetic acid esters is to CCl4It induces acute hepatocellular injury that there is protective effect, can be used for liver protecting.
2 7- of embodiment (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters, i.e. 7- (2,2- diformazans Base -3- crotonoyl amido) -2,4- dimethyl -5- oxo -1,2,3,4,4a, 5,6,10b- octahydro benzo [f] -1- quinolyl-second Acid esters is to internal CCl4The protective effect of inducing mouse acute hepatic injury is tested.
Reagent and drug:
Bifendate (BDP) (Beijing XieHe medicine Factory)；ALT(glutamic-pyruvic transaminase) detection kit and AST(glutamic-oxalacetic transaminease) inspection Test agent box (Bioisystech Co., Ltd is built up in Nanjing)；CCl4(western Gansu Province science limited liability company, analysis are pure)；Carboxymethyl is fine Tie up plain sodium (western Gansu Province science limited liability company, analysis are pure)；Olive oil (golden dragonfish board superfine olive oil)；DQA, i.e. 7- (2,2- Dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters, by laboratory from medicinal plant Rhizophora stylosa aerial root endophyte Extract isolated, purity > 98% (HPLC).
Kunming mouse, weight (25 ± 2) g, male and female dual-purpose, Hunan SJA Laboratory Animal Co. , Ltd.
Experimental method and result:
60 Kunming mouses are taken, are randomly divided into 6 groups, every group of half male and half female.It is respectively set to Normal group, CCl4Model pair According to group, BDP positive controls, difference DQA dosage group.Suspension is made using 0.8% sodium carboxymethylcellulose in drug Liquid, each dosage group press 0.1mL/10g/d dosage gastric infusion, Normal group and CCl4Model control group gives same volume Long-pending sodium carboxymethylcellulose, daily stomach-filling is primary, and continuous 7 days.After last dose 2h, olive oil is injected intraperitoneally in Normal group 0.1mL/10g, remaining 5 groups of 0.1% CCl of injection40.1mL/10g.After being deprived of food but not water 16h, pluck eyeball and take blood, 3500rpm from The heart separates 15min, measures the activity of serum alt and AST, and wins the same position of liver lobus sinister, fixed, embeds, slice, HE Dyeing, microscopically observation histomorphological changes.As a result as follows:
Compared with Normal group: ### indicates P < 0.001；With CCl4Model control group compares: * * indicates P < 0.01, * * * Indicate P < 0.001.
Table 2 the result shows that, mouse peritoneal inject CCl4After inducing acute liver damage, the activity of serum alt and AST are significant It increases, and after DQA is administered in advance in mouse, serum alt and AST value and CCl4Model control group compares, different dosing dosage There is the phenomenon that reducing serum alt and AST value, it is best that high dose group reduces ALT and AST value effect.The above results explanation, 7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters is to CCl4Inducing mouse acute hepatic injury, which has, to be protected Shield effect.
Hepatic pathology tectology inspection result is shown in Fig. 1, and Normal group mouse liver eucaryotic cell structure is normal, and size is equal Even, marshalling is demarcated clear, and nucleus is complete, and interstitial is completely embedded, and has no that pathologic changes；CCl4Model control group is small Mouse liver volume increases, and focal necrosis and spotty necrosis, disorganized, cytomorphosis is presented in cell, and cell nucleus shrinks distort, carefully There is apparent cavity every increase in intercellular；There is apparent non-viable non-apoptotic cell in BDP positive controls mouse liver cell and new life is thin The line of demarcation of born of the same parents；Equally there is the line of demarcation of apparent non-viable non-apoptotic cell and neonatal cell in DQA high dose group mouse liver cell, with Positive drug effect is identical；DQA middle dose group and low dose group mouse liver meronecrosis degree are also reduced to varying degrees. The above results explanation, 7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters damage internal liver organization organ Wound has significant repair, can be used to treat or prevent liver diseases.
As can be seen from the above embodiments, 7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters is in body In interior and experiment in vitro, good liver protecting effect is shown, can be used for preparing hepatic, food or health care product, also It can be used for preparing drug, food or the health care product of hepatocellular injury protection；There is significant repair to liver organization organ damage Effect can be used for preparing drug, food or the health care product for treating or preventing liver diseases.
7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters of the present invention derives from crude drug With plant Rhizophora stylosa aerial root endophyte, belong to pure natural source, securely and reliably, toxic side effect is small, to caused by many reasons Hepar damnification all has protection and preventive and therapeutic effect.
To sum up, 7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters of the present invention, i.e. 7- (2, 2- dimethyl -3- crotonoyl amido) -2,4- dimethyl -5- oxo -1,2,3,4,4a, 5,6,10b- octahydro benzo [f] -1- quinoline Quinoline base-acetic acid esters has significant protective effect in vitro liver cell damage, can be used for preparing the drug of liver protecting, food or Health care product；There is significant repair to internal liver organization organ damage, can be used for preparing treatment or prevention liver diseases Drug, food or health care product, be suitable for large-scale promotion, have wide development and application prospect.
In this description, the present invention is described with reference to its specific embodiment.But it is clear that can still make Various modifications and alterations are without departing from the spirit and scope of the invention.Therefore, the description and the appended drawings should be considered as illustrative And not restrictive.

Claims (1)

1.7- (2,2- dimethyl -3- crotonoyl amido)-octahydro benzene quinoline acetic acid esters, i.e. 7- (2,2- dimethyl -3- crotonamides Base) -2,4- dimethyl -5- oxo -1,2,3,4,4a, 5,6,10b- octahydro benzo [f] -1- quinolyl-acetic acid esters controls in preparation Purposes in the drug for the treatment of or prevention hepar damnification, food or health care product.
CN201810793903.8A 2018-07-19 2018-07-19 Application of 7- (2, 2-dimethyl-3-butenamido) -octahydro phenylquinoline acetate in preparation of medicine for treating liver diseases Active CN109045035B (en)

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN113648311A (en) * 2021-08-31 2021-11-16 广西科技大学 Application of 7- (2, 2-dimethyl-3-butenamido) -octahydro phenylquinoline acetate in preparation of lipid-lowering drugs
CN113717999A (en) * 2021-10-11 2021-11-30 广西科技大学 Culture medium for producing 7- (3-butenamide) -octahydrobenzoquinoline acetate by utilizing endophytic oxytetracycline and application thereof
CN114224893A (en) * 2022-01-25 2022-03-25 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) Application of quinazoline derivative in preparation of drug for preventing and treating arsenic-induced liver injury

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113648311A (en) * 2021-08-31 2021-11-16 广西科技大学 Application of 7- (2, 2-dimethyl-3-butenamido) -octahydro phenylquinoline acetate in preparation of lipid-lowering drugs
CN113717999A (en) * 2021-10-11 2021-11-30 广西科技大学 Culture medium for producing 7- (3-butenamide) -octahydrobenzoquinoline acetate by utilizing endophytic oxytetracycline and application thereof
CN114224893A (en) * 2022-01-25 2022-03-25 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) Application of quinazoline derivative in preparation of drug for preventing and treating arsenic-induced liver injury
CN114224893B (en) * 2022-01-25 2023-06-06 贵州省中国科学院天然产物化学重点实验室(贵州医科大学天然产物化学重点实验室) Application of quinazoline derivative in preparation of drugs for preventing and treating arsenic-induced liver injury

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