CN110507660A - Pentacyclic triterpenoid is preparing the purposes in bacillary hemolysin inhibitor - Google Patents

Pentacyclic triterpenoid is preparing the purposes in bacillary hemolysin inhibitor Download PDF

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Publication number
CN110507660A
CN110507660A CN201910905953.5A CN201910905953A CN110507660A CN 110507660 A CN110507660 A CN 110507660A CN 201910905953 A CN201910905953 A CN 201910905953A CN 110507660 A CN110507660 A CN 110507660A
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remain unchanged
compound
case
hemolysin
groups remain
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邓旭明
周永林
王建锋
郭岩
王大成
牛效迪
邱家章
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Jilin University
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Jilin University
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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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • 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
    • A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
    • A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents

Abstract

The present invention relates to pentacyclic triterpenoids to prepare the purposes in hemolysin inhibitor, provide the new purposes of one kind of pentacyclic triterpenoid, the activity of bacteriohemolysin can be neutralized by disclosing pentacyclic triterpenoid, reduce death caused by bacterium infects the damage of host cell and animal pattern；By inhibiting the activity of hemolysin to reach the protective effect to body；Pentacyclic triterpenoid can prepare the drug for producing hemolysin bacterium infection.

Description

Pentacyclic triterpenoid is preparing the purposes in bacillary hemolysin inhibitor
Technical field
The invention discloses pentacyclic triterpenoids to prepare the purposes in bacillary hemolysin inhibitor, provides five The new purposes of one kind of ring triterpene compound, belongs to medicine pharmaceutical technology field.
Background technique
The problem of bacterial drug resistance, has become a focus of attention in the whole world, wherein more serious with S. aureus L-forms etc..It is resistance to Medicine bacterium infects the treatment failure for leading to antibiotic and the higher death rate, infects band to treatment nosocomial infection, particularly treatment ICU Bigger pressure is carried out.Bacteriohemolysin plays the role of vital during bacterium is cured the disease, and is mainly shown as pair Histocyte causes to damage, and can punch destruction cell in cell membrane surface makes bacterium obtain more nutriments.It can make red thin Born of the same parents' rupture causes haemolysis.Currently, studying more haemolysis is known as staphylococcus aureus (such as methicillin-resistant staphylococcus Portugal Grape coccus) hemolysin, listeria monocytogenes hemolysin LLO, pneumolysin PLY and Hemolysin SLY etc.. Therefore, hemolysin activity is inhibited to cause the pathogenic bacterial infection of damage to anticipate body by hemolysin by S. aureus L-forms etc. are main treatment Justice is great.
Pentacyclic triterpenoid of the present invention: such as oleanolic acid, Corosolic acid, hawthorn acid and ursolic acid, it is main Be present in a variety of natural plants, such as hawthorn, wither mound dish, Song wood root skin and olive fruit and branches and leaves in, to human body use It is highly-safe.Discovered in recent years pentacyclic triterpenoid has the multiple biological activities such as anticancer, anti-oxidant and anti-diabetic.
Have no pentacyclic triterpenoid as the document report in terms of novel hemolysin inhibitor through retrieval.
Summary of the invention
The present invention provides a kind of pentacyclic triterpenoids to prepare the medical application in bacillary hemolysin inhibitor. The activity of bacteriohemolysin can be neutralized by disclosing pentacyclic triterpenoid, reduce damage and model of the bacterium to host cell Death caused by zoogenetic infection.The present invention verifies pentacyclic triterpenoid by hemolytic test, test cell line and animal experiment It is able to suppress the activity of hemolysin, to reach the protective effect to body.
Pentacyclic triterpenoid of the present invention has following structure formula:
R is removed in the general structure1, R2, R3, R4, R5, R6, R7, R8, R9And R10Other positions remain unchanged in addition, R1, R2, R3, R4, R5, R6, R7, R8, R9And R10It can be the biological activity of any pair of parent nucleus and the group having improved solubility；It ties part Structure is as follows:
1) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is oleanolic acid；
2) is in the case where other groups remain unchanged, wherein R1For H, R2For CH3, R3For CH3, R4For H, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For OH, this compound is Corosolic acid；
3) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For OH, this compound is hawthorn acid；
4) is in the case where other groups remain unchanged, wherein R1For H, R2For CH3, R3For CH3, R4For H, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is ursolic acid；
5) is in the case where other groups remain unchanged, wherein R1For H, R2For OH, R3For CH3, R4For CH3, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For OH, this compound is arjunolic acid；
6) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For CH3, R6For H2, R7For CH3, R8For COOH, R9For OH, R10For H2, this compound is α-masticinic acid；
7) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COOH, R6For H2, R7For CH2OH, R8For CH3, R9For OH, R10For H2, this compound is hederagenin；
8) is in the case where other groups remain unchanged, wherein R1For OH, R2For CH3, R3For CH3, R4For H, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For OH, this compound is tormentic acid；
9) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For (CH2OH), R6For H2, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is erythrodiol；
10) is in the case where other groups remain unchanged, wherein R1For H, R2For CH3, R3For CH3, R4For H, R5For (CH2OH), R6For H2, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is uvaol；
11) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COOH, R6For OH, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is echinocystic acid；
12) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COONa, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is Caryophyllin acid sodium；
13) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COONa, R6For H2, R7For CH3, R8For CH3, R9ForR10For H2, this compound is oleanolic acid neighbour benzene two Formic acid monoesters disodium；
14) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5ForR6For H2, R7For CH3, R8For CH3, R9ForR10For H2, this compound For Song wood saponin A；
15) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For CH3, R6For H2, R7For CH3, R8For H, R9For O, R10For H2, this compound is suberone；
16) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For COOH, R5For CH3, R6For H2, R7For CH3, R8For H, R9For OH, R10For O, this compound is tripterygone；
Main pentacyclic triterpenoid molecular structure of the present invention is shown below:
Pentacyclic triterpenoid of the present invention mediates host cell in preparation inhibition production hemolysin bacterium thin Purposes in cytotoxic drugs.
Pentacyclic triterpenoid of the present invention causes the medicine of disease in preparation treatment S. aureus L-forms mediation mouse infection Purposes in object.
Pentacyclic triterpenoid of the present invention treats the purposes produced in hemolysin bacterium infection drug in preparation.
It is pharmaceutically may be used that pentacyclic triterpenoid of the present invention and pharmaceutically acceptable auxiliary material, which are prepared into various, The carrier of receiving, such as injection, capsule, tablet or powder-injection dosage form.
The present invention has high excellent of cure rate compared with antibiotic treatment, using pentacyclic triterpenoid treatment Point.
The positive effect of the present invention is:
The new purposes of one kind of pentacyclic triterpenoid is provided, disclosing pentacyclic triterpenoid can neutralize carefully The activity of bacterium hemolysin reduces death caused by bacterium infects the damage of host cell and animal pattern；By inhibiting haemolysis The activity of element is to reach the protective effect to body；Pentacyclic triterpenoid can prepare the medicine for producing hemolysin bacterium infection Object.
Specific embodiment
By following embodiment further illustrate description the present invention, do not limit the invention in any way, without departing substantially from Under the premise of technical solution of the invention, easy to accomplish any of those of ordinary skill in the art made for the present invention changes Dynamic or change is fallen within scope of the presently claimed invention.
Embodiment 1
Pentacyclic triterpenoid is used for pharmaceutically acceptable any carrier as the inhibitor of hemolysin.
Embodiment 2
Pentacyclic triterpenoid is used to prepare the drug for the treatment of infectious diseases as the inhibitor of hemolysin.
Embodiment 3
Pentacyclic triterpenoid is used to treat infectious diseases caused by bacterium as the inhibitor of hemolysin.
Test example 1
S. aureus L-forms alpha hemolysin, listeria monocytogenes hemolysin LLO, pneumolysin PLY and the pig chain of purifying Pneumoniae pneumolysin SLY makees continuous doubling dilution in 96 orifice plates, is added 10 in each hole7A rabbit erythrocyte is incubated in 37 DEG C It is centrifuged after educating 30 minutes.Alpha hemolysin, LLO hemolysin, PLY hemolysin and the SLY hemolysin highest for being completely dissolved red blood cell Extension rate is considered as haemolysis titre (Hemolysis titre).Pentacyclic triterpenoid is with the chemical combination of above-mentioned presentation structural formula Object is main study subject, after pentacyclic triterpenoid is handled, the haemolysis titre of hemolysin such as table 1 to table 4.
In 1. pentacyclic triterpenoid of table and the effect of S. aureus L-forms alpha hemolysin hemolytic activity
In 2. pentacyclic triterpenoid of table and the effect of Listeria monocytogenes LLO hemolysin hemolytic activity
In 3. pentacyclic triterpenoid of table and the effect of streptococcus pneumonia PLY hemolysin hemolytic activity
In 4. pentacyclic triterpenoid of table and the effect of Streptococcus suis SLY hemolysin hemolytic activity
Conclusion: pentacyclic triterpenoid can significantly reduce S. aureus L-forms alpha hemolysin, listeria monocytogenes hemolysin LLO, The lysed erythrocyte activity that pneumolysin PLY and Hemolysin SLY is mediated, and gradient dependence is presented.
Test example 2
Protective effect of the pentacyclic triterpenoid to A549 cell and J774 cell
Alpha hemolysin and PLY hemolysin select A549 cell, and LLO hemolysin and SLY hemolysin select J774 cell.Cell It is plated on (2 × 10 in 96 orifice plates4A/hole), and culture (DMEM complete medium, 37 DEG C, 5%CO2) 24 hours, every hole adds respectively Enter the haemolysis fibroin of the purifying of certain concentration and the pentacyclic triterpenoid of different gradient drugs is added, it is small to continue culture 5 When, centrifugation (1000rpm, 10min) takes supernatant, detects the activity of lactic dehydrogenase in supernatant to detect the survival rate of cell. This test using oleanolic acid, koroso is and Caryophyllin acid sodium is main study subject, as a result (table 5-8) show oleanolic acid, Koroso is and Caryophyllin acid sodium significantly inhibits bacillary hemolysin to the cytotoxic effect of A549 cell and J774 cell, And concentration dependent is presented in this effect.
The cytotoxic effect that 5. pentacyclic triterpenoid of table inhibits alpha hemolysin cell-mediated to A549
The cytotoxic effect that 6. pentacyclic triterpenoid of table inhibits PLY hemolysin cell-mediated to A549
The cytotoxic effect that 7. pentacyclic triterpenoid of table inhibits LLO hemolysin cell-mediated to J774
The cytotoxic effect that 8. pentacyclic triterpenoid of table inhibits SLY hemolysin cell-mediated to J774
Test example 3
Protective rate test
(1) infection of staphylococcus aureus model: C57 mouse (male, 18-22g) via intranasal application instills 20 μ l (109CFU/ Ml) 25mg/kg pentacyclic triterpenoid and 50mg/kg pentacyclic triterpene chemical combination are subcutaneously injected respectively within 2 hours after S. aureus L-forms Object is administered once for every 12 hours.The DMSO (two subunit sulfoxides) that control group gives 50 μ l, every group of 30 mouse are not administered.By giving After medicine administration, mouse infection S. aureus L-forms are recorded for 24 hours respectively, the death rate after 48h and 72h.This test with oleanolic acid and Caryophyllin acid sodium is main study subject.It the results are shown in Table 9 and table 10.
9. oleanolic acid of table reduces the death rate of mouse S. aureus L-forms infection
10. Caryophyllin acid sodium of table reduces the death rate of mouse S. aureus L-forms infection
Conclusion: after oleanolic acid drug treatment, discovery oleanolic acid can effectively reduce the death of S. aureus L-forms infecting mouse Rate, wherein 50mg/kg oleanolic acid therapeutic effect is substantially better than 25mg/kg oleanolic acid.In addition, the neat pier of same dosage The effect of tartaric acid sodium relatively oleanolic acid is more effective, and therefore, pentacyclic triterpenoid has S. aureus L-forms infecting mouse The therapeutic effect of effect.
(2) Listeria monocytogenes infection model: Balb/c mouse (male, 18-22g) is through being injected intraperitoneally 200 μ l (108CFU/ml) 25mg/kg pentacyclic triterpenoid and 50 mg/kg five are subcutaneously injected respectively within 2 hours after Listeria monocytogenes Ring triterpene compound is administered once for every 12 hours.It is not administered the DMSO (two subunit sulfoxides) that control group gives 50 μ l, every group 30 Mouse.After Dosage Regimens Dosage, the death rate after mouse infection Listeria monocytogenes 48h, 72h and 96h is recorded respectively. This test is using oleanolic acid and Caryophyllin acid sodium as main study subject.It the results are shown in Table 11 and table 12.
11. oleanolic acid of table reduces the death rate of mouse Listeria monocytogenes infection
12. Caryophyllin acid sodium of table reduces the death rate of mouse Listeria monocytogenes infection
Conclusion: after oleanolic acid drug treatment, discovery oleanolic acid can effectively reduce Listeria monocytogenes infecting mouse The death rate, wherein 50mg/kg oleanolic acid therapeutic effect is substantially better than 25mg/kg oleanolic acid.In addition, same dosage Caryophyllin acid sodium relatively oleanolic acid effect it is more effective.Therefore, pentacyclic triterpenoid is to Listeria monocytogenes sense Contaminating mouse has effective therapeutic effect.

Claims (6)

1. pentacyclic triterpenoid treats the purposes produced in hemolysin bacterium infection drug in preparation；
Above-mentioned pentacyclic triterpenoid has following structure general formula:
R is removed in the general structure1, R2, R3, R4, R5, R6, R7, R8, R9And R10Other positions remain unchanged in addition, R1, R2, R3, R4, R5, R6, R7, R8, R9And R10It can be the biological activity of any pair of parent nucleus and the group having improved solubility；
Part-structure is as follows:
1) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is oleanolic acid；
2) is in the case where other groups remain unchanged, wherein R1For H, R2For CH3, R3For CH3, R4For H, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For OH, this compound is Corosolic acid；
3) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For OH, this compound is hawthorn acid；
4) is in the case where other groups remain unchanged, wherein R1For H, R2For CH3, R3For CH3, R4For H, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is ursolic acid；
5) is in the case where other groups remain unchanged, wherein R1For H, R2For OH, R3For CH3, R4For CH3, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For OH, this compound is arjunolic acid；
6. in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For CH3, R6For H2, R7For CH3, R8For COOH, R9For OH, R10For H2, this compound is α-masticinic acid；
7) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COOH, R6For H2, R7For CH2OH, R8For CH3, R9For OH, R10For H2, this compound is hederagenin；
8) is in the case where other groups remain unchanged, wherein R1For OH, R2For CH3, R3For CH3, R4For H, R5For COOH, R6For H2, R7For CH3, R8For CH3, R9For OH, R10For OH, this compound is tormentic acid；
9) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For (CH2OH), R6 For H2, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is erythrodiol；
10) is in the case where other groups remain unchanged, wherein R1For H, R2For CH3, R3For CH3, R4For H, R5For (CH2OH), R6For H2, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is uvaol；
11) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COOH, R6For OH, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is echinocystic acid；
12) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COONa, R6 For H2, R7For CH3, R8For CH3, R9For OH, R10For H2, this compound is Caryophyllin acid sodium；
13) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For COONa, R6 For H2, R7For CH3, R8For CH3, R9ForR10For H2, this compound is oleanolic acid phthalic monoester Disodium；
14) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5ForR6For H2, R7For CH3, R8For CH3, R9ForR10For H2, this change Conjunction object is Song wood saponin A；
15) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For CH3, R5For CH3, R6For H2, R7For CH3, R8For H, R9For O, R10For H2, this compound is suberone；
16) is in the case where other groups remain unchanged, wherein R1For H, R2For H, R3For CH3, R4For COOH, R5For CH3, R6For H2, R7For CH3, R8For H, R9For OH, R10For O, this compound is tripterygone.
2. pentacyclic triterpenoid as described in claim 1 treats the purposes produced in hemolysin bacterium infection drug in preparation, It is characterized by:
The production hemolysin bacterium infection, which refers to, expresses bacterial infection caused by the pathogen of hemolysin as all, wherein Bacterial infection refers to the infection as caused by the pathogen of expression hemolysin.
3. pentacyclic triterpenoid as described in claim 1 treats the purposes produced in hemolysin bacterium infection drug in preparation, It is characterized by:
Pentacyclic triterpenoid and pharmaceutically acceptable auxiliary material are prepared into various for pharmaceutically acceptable carrier, such as injection The dosage forms such as liquid, capsule, tablet or powder-injection.
It is used 4. pentacyclic triterpenoid inhibits to produce in the cytotoxic drug that hemolysin bacterium mediates host cell in preparation On the way.
5. pentacyclic triterpenoid purposes in the drug that preparation treatment S. aureus L-forms mediate mouse infection to cause disease.
6. pentacyclic triterpenoid treats the purposes produced in hemolysin bacterium infection drug in preparation.
CN201910905953.5A 2019-09-24 2019-09-24 Pentacyclic triterpenoid is preparing the purposes in bacillary hemolysin inhibitor Pending CN110507660A (en)

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