CN108096249B - The new opplication of lotus nut alkaloid compound - Google Patents
The new opplication of lotus nut alkaloid compound Download PDFInfo
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- CN108096249B CN108096249B CN201711224744.1A CN201711224744A CN108096249B CN 108096249 B CN108096249 B CN 108096249B CN 201711224744 A CN201711224744 A CN 201711224744A CN 108096249 B CN108096249 B CN 108096249B
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- pseudomonas aeruginosa
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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
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
Abstract
The application belongs to field of medicaments, discloses the new opplication of lotus nut alkaloid compound, especially lotus nut alkaloid compound in the application of preparation bacterial community induction system inhibited in drug.Experiment shows that lotus nut alkaloid compound all has inhibitory effect for the biomembrane of three kinds of pseudomonas aeruginosa 9027, pseudomonas aeruginosa 27853 and tolerant Pseudomonas aeruginosa pseudomonas aeruginosas, show that lotus nut alkaloid compound of the present invention can reach the growth that can not inhibit bacterium while reducing bacterial virulence and pathogenicity by the intervention school-based of inhibition bacterium, is not likely to produce the effect of bacterial drug resistance.The especially described lotus nut alkaloid compound all has more suitable than positive drug furan ketone compound or better inhibitory effect for the biomembrane of pseudomonas aeruginosa and tolerant Pseudomonas aeruginosa, shows lotus nut alkaloid compound of the present invention and all has good inhibitory effect for pseudomonas aeruginosa and tolerant Pseudomonas aeruginosa.
Description
Technical field
The invention belongs to field of medicaments, and in particular to the new opplication of lotus nut alkaloid compound, especially lotus nut bases chemical combination
The application that inhibits in drug of the object in preparation bacterial community induction system.
Background technique
With the extensive use of antibiotic, the drug resistance intensity of microorganism is higher and higher, Antibiotic Resistance is more and more wider, drug resistance shape
At speed rising proportional to antibiotic sterilization capability.Drug resistance once generates, it will keeps.Antibiotic continues to make
With only continuing to provide selection pressure for high antibody-resistant bacterium, promote its duplication, group structure and enjoy drug resistant gene jointly, cause more
The quickening of weight antibody-resistant bacterium is formed.Currently, antibiotic resistance has become the serious public health problem in the whole world.
China causes 80,000,000,000 yuan of medical expenses to increase because of abuse of antibiotics every year, while causing 80,000 patients bad anti-because of its
Answer death.No matter illness weight, operation size at present, all using antibiotic and tending to high-titer antibiotic and often
A large amount of blindness long-time drug combinations even use 4 kinds or more of antibiotic in a short time and lead to new antibody-resistant bacterium individually
It continuously emerges.Some experts even predict that China may take the lead in enter " rear antibiotic epoch ", that is, return to antibiotic discovery before when
Generation.
China possesses Chinese medicine and natural pharmaceutical resources extremely abundant, nearly ten thousand kinds of medicinal plant, provides for new drug discovery
Material base abundant and source.Moreover, carrying out antibacterial, anti-inflammatory with Chinese patent drug substitute antibiotics, there is adverse reaction and secondary work
With it is relatively small, do not generate the advantages that drug resistance.On the other hand, world medical circle does not have real meaning in existing 40 years time
On new antibiotic be born.Therefore, many researchers focus on crude drug " antibiotic " in spite of oneself
On.Finding from traditional Chinese medicine resource equally has the alternative product of the antibiotic of antibacterial anti-inflammatory curative effect, and it is anti-that it will be solved well
Raw this world-famous puzzle of element drug resistance.
In recent years, bacterial community induction (Quorum sensing, QS) system has become the novel drug-resistance bacteria medicine of research
Important target.The inhibiting effect mechanism for the bacterium studied extensively at present, which mainly passes through, to be inhibited DNA of bacteria gyrase, inhibits bacterium
The function of cytoplasma membrane inhibits bacterium energetic supersession etc. and plays bacteriostasis efficacy.And the inhibition of bacterial community induction and bacterium
The mechanism of action is different.Bacterial community induction (Quorum sensing, QS) is the intercellular signal for depending on bacterial density
Conducting system critically adjusts bacterial community behavior in a manner of chemistry exchange, including is formed to bacterial biof iotalm, virulence factor
Gene expression, the generation of drug resistance, the regulation of bacteria motility and cometabolism.Pass through suppression by target of bacterial community induction system
It makes its ability of regulation and control and then reduces the expression of the related virulence gene of its regulation and inhibit the pathogenecity of bacterium, can reduce
The growth for not inhibiting bacterium while bacterial virulence and pathogenicity will not generate choosing to the existence of bacterium compared with conventional antibiotic
Selecting property pressure, is theoretically not likely to produce bacterial drug resistance.QS is a kind of mode that in bacterial cell or intercellular signal transmits, and is led to
Cross monitor certain signaling molecules (also known as autoinducer) such as homoserine lactone (acyl-homoserine lactone,
AHL concentration) is jointly made a response to ambient enviroment stimulation, is greatly enhanced to control and coordinate entire bacterial community behavior
The survival ability of entire bacterial community.
Lotus Plumule (Plumula nelumbinis), also known as the lotus heart of a lotus seed, the bitter heart of a lotus seed, lotus nut, see " the feeding habits sheet at Tang end earliest
Grass " in, it is the drying plumule in the perennial water plant lotus mature seed of Nymphaeceae.Its main place of production be distributed in China Hunan,
Hubei, Fujian, Jiangsu, Zhejiang, Jiangxi etc. save.Lotus Plumule is cold in nature, bitter, return heart, kidney channel, has clearing away the heart fire and tranquillizing, restoring normal coordination between heart and kidney
And the effect of unsmoothing the sperm and stopping bleeding, is for treating the diseases such as the invasion of pericardium by heat, coma and delirium, breakdown of the normal physiological coordination between the heart and the kidney, insomnia spermatorrhea and blood-head haematemesis
Common one of the Chinese medicine with " clearing heat and detoxicating " effect.Lotus Plumule chemical component includes: double benzyl tetrahydro isoquinoline class biologies
Alkali, monobenzyl tetrahydroisoquinoline alkaloid, flavonoids, sterol and organic acid, volatile oil etc., wherein with lotus nut bases
It closes the characteristic chemical constituent that double benzyl tetrahydro isoquinoline Alkaloids based on object are Lotus Plumule and its content is higher.System reviews lotus
The document of the sub- heart finds, modern pharmacology and clinical research also indicate that Lotus Plumule to pseudomonas aeruginosa, bacillus salmonella, golden yellow
The common bacterias such as color staphylococcus, Escherichia coli, bacillus subtilis all have stronger inhibiting effect, but do not find it
Inhibit the document report of bacterial community induction system.
Lotus nut alkaloid compound is a kind of Bisbenzylisoquinolincompounds monoether bond type alkaloid proposed from Chinese medicine Lotus Plumule, tool
There is the effects of decompression, anti-arrhythmia, block adrenal gland α receptor and inhibit calcium release.Up to the present, it is reported
It focuses mostly in terms of pharmacology and extraction, analysis, not yet finds that it plays the role of inhibiting bacterial community induction system at present.
Summary of the invention
In view of this, that is, lotus nut alkaloid compound is thin in preparation the present invention provides the new opplication of lotus nut alkaloid compound
The application of bacteria quorum sensing system inhibited in drug.
Pseudomonas aeruginosa (P.aeruginosa) has the very strong ability that biomembrane is formed in tissue surface, and its
QS system research obtains also the most thoroughly, therefore pseudomonas aeruginosa is chosen as mode bacterium.Pseudomonas aeruginosa is a kind of important
Conditioned pathogen usually causes the inside-hospital infections such as respiratory tract infection, pneumonia, urethral infection, it is considered to be patient is in hospital
The third-largest pathogenic bacteria that period infects seriously endanger the health and life of the mankind.The high inherence of pseudomonas aeruginosa is anti-
Pharmacological property is inseparable with its intervention school-based, and it includes biomembrane, exotoxin, elastoser, haemolysis which, which controls,
The expression of nearly all virulence factor such as element, pyo.These virulence factors determine cause of the pseudomonas aeruginosa to host
Sick ability.Wherein, the formation and diffusion of biomembrane are to cause an important mechanisms of P.aeruginosa multidrug resistant.State, the U.S.
The authoritative survey report of the portion of vertical Institutes of Health Research (NIH) publication points out, human microbial is infected with being by thin more than 80%
What bacterium biofilm (Biofilm, BF) mediated.BF is as a kind of bacterial community behavior, differentiation and development and bacterial flora body-sensing
It answers closely related.The complete bacterium of bacterial community induction system can form development and break up normal, typical can fight and kill
The biomembrane of microbial inoculum, and the bacterium of bacterial community induction system incompleteness cannot then form typical biomembrane, support to antibiotic
Drag is remarkably decreased, and is easy to be rinsed and sensitive to fungicide.Therefore, it is formed by quenching control bacterial biof iotalm
It will because not inhibiting bacterial growth directly, selection pressure will not be generated to bacterium with the QS system of pathogen virulence factor expression
Get a good chance of obtaining group's sense inhibitor (QS inhibitors, QSI) for acting on novel targets, bacterium will not being made to generate drug resistance.
The present invention carries out biomembrane Inhibition test using pseudomonas aeruginosa as research object.Lotus nut bases as the result is shown
Compound all has inhibitory effect for the biomembrane of three kinds of pseudomonas aeruginosas, shows lotus nut alkaloid compound of the present invention
It can not can inhibit bacterium while reducing bacterial virulence and pathogenicity by inhibiting the intervention school-based of bacterium to reach
Growth, be not likely to produce the effect of bacterial drug resistance.The i.e. described lotus nut alkaloid compound can be by inhibiting pseudomonas aeruginosa
And/or tolerant Pseudomonas aeruginosa biomembrane plays the effect of resisting pseudomonas aeruginosa and/or tolerant Pseudomonas aeruginosa.
Therefore, the answering in the inhibition drug of preparation bacterial community induction system the present invention provides lotus nut alkaloid compound
With.
Wherein, lotus nut alkaloid compound of the present invention is the compound with Formulas I structure,
Wherein, described R1, R2, R3, R4, R5 are independently selected from hydrogen or methyl.
Preferably, the lotus nut alkaloid compound is compound 1-6, it is false for pseudomonas aeruginosa and drug resistance verdigris
The biomembrane of monad all has more suitable than positive drug furan ketone compound or better inhibitory effect.The compound 1-6,
Specific structure is as follows:
Preferably, the bacterium is pseudomonas aeruginosa and tolerant Pseudomonas aeruginosa.
Preferably, drug of the present invention includes the lotus nut alkaloid compound of effective dose.
Further, the lotus nut alkaloid compound is preferably the compound with structure shown in Formulas I.More preferably describedization
Close at least one of object 1-6.
Preferably, drug of the present invention further includes pharmaceutically acceptable auxiliary material.
Those skilled in the art can directly or indirectly addition prepares different dosage forms by lotus nut alkaloid compound shown in the Formulas I
The pharmaceutically acceptable various common auxiliary materials of Shi Suoxu, such as filler, disintegrating agent, lubricant, adhesive, with conventional medicine
Common oral preparation or ejection preparation is made in formulation method.
Preferably, the oral preparation is tablet, capsule, granule.
Preferably, the ejection preparation is injection or powder-injection.
Drug of the present invention its by 10%-90% lotus nut alkaloid compound and 10%-90% it is pharmaceutically acceptable
Auxiliary material composition.
In some embodiments, the drug is resisting pseudomonas aeruginosa granule, is made of following raw material:
1 10 parts of compound, 15 parts of lactose, 4 parts of 10% starch slurry.
In some embodiments, the drug is resisting pseudomonas aeruginosa capsule, is made of following raw material:
5 25 parts of compound, 40 parts of lactose, 40 parts of microcrystalline cellulose, 4 parts of talcum powder.
In some embodiments, the drug is overriding resistance pseudomonas aeruginosa tablet, by following raw material system
At: 6 20 parts of compound, 15 parts of lactose, 5 parts of 10% starch slurry, 10 parts of crospovidone, 1 part of magnesium stearate.
In some embodiments, the drug is resisting pseudomonas aeruginosa granule, is made of following raw material:
4 15 parts of compound, 20 parts of lactose, 3 parts of 10% starch slurry.
In some embodiments, the drug is resisting pseudomonas aeruginosa capsule, is made of following raw material:
2 20 parts of compound, 30 parts of lactose, 30 parts of microcrystalline cellulose, 3 parts of talcum powder.
In some embodiments, the drug is overriding resistance pseudomonas aeruginosa tablet, by following raw material system
At: 3 15 parts of compound, 10 parts of lactose, 4 parts of 10% starch slurry, 8 parts of crospovidone, 2 parts of magnesium stearate.
As shown from the above technical solution, the present invention provides the new opplications of lotus nut alkaloid compound, especially lotus nut bases
The application that inhibits in drug of the compound in preparation bacterial community induction system.Experiment shows lotus nut alkaloid compound for verdigris
Pseudomonad 9027, three kinds of pseudomonas aeruginosas of pseudomonas aeruginosa 27853 and tolerant Pseudomonas aeruginosa biomembrane have
Have inhibitory effect, show lotus nut alkaloid compound of the present invention can by inhibiting the intervention school-based of bacterium reach can
The growth for not inhibiting bacterium while reducing bacterial virulence and pathogenicity, is not likely to produce the effect of bacterial drug resistance.Especially
The lotus nut alkaloid compound, which all has the biomembrane of pseudomonas aeruginosa and tolerant Pseudomonas aeruginosa, compares positive drug
Furan ketone compound is suitable or better inhibitory effect, show lotus nut alkaloid compound of the present invention for pseudomonas aeruginosa and
The green pseudomonad of drug resistance all has good inhibitory effect.
Specific embodiment
The invention discloses the new opplications of lotus nut alkaloid compound.Those skilled in the art can use for reference present disclosure, fit
When improvement realization of process parameters.In particular, it should be pointed out that all similar substitutions and modifications are for a person skilled in the art
It is it will be apparent that they are considered as being included in the present invention.Method and product of the invention passed through preferred embodiment into
Description is gone, related personnel can obviously not depart from the content of present invention, change in spirit and scope to method described herein
Dynamic or appropriate changes and combinations, carry out implementation and application the technology of the present invention.
For a further understanding of the present invention, below in conjunction with the embodiment of the present invention, to the technical side in the embodiment of the present invention
Case is clearly and completely described, it is clear that and described embodiments are only a part of the embodiments of the present invention, rather than all
Embodiment.Based on the embodiments of the present invention, those of ordinary skill in the art institute without making creative work
The every other embodiment obtained, shall fall within the protection scope of the present invention.
Unless otherwise specified, reagent involved in the embodiment of the present invention is commercial product, can pass through business canal
Road purchase obtains.
Embodiment 1: the extraction separated structure identification of lotus nut alkaloid compound
(1) Lotus Plumule (Plumula Nelambinis) 20.5kg, with 12 times measure 80% (v/v) ethyl alcohol soaked overnight after
Heating and refluxing extraction 3 times, Extracting temperature is 10~150 DEG C, 2 hours every time, obtains primary extract；
(2) it is filtered to remove insoluble matter, filtrate decompression is dried to obtain ethanol extract；
(3) ethanol extract is respectively with isometric petroleum ether, ethyl acetate and extracting n-butyl alcohol 3 times；
(4) butanol extraction liquid is taken, vacuum decompression is dry, obtains n-butanol extract 4.5g；
(5) using silica gel column chromatography repeatedly, open ODS column chromatography, Sephadex LH-20 column chromatography, the efficient liquid of preparative
The isolation and purification methods such as phase chromatography carry out chemical component separation to Lotus Plumule n-butanol extract, obtain compound 1-6.
(6) structure of compound 1-6 is identified by physicochemical property and method of spectroscopy, they are respectively: liensinine
(Liensinine, compound 1), isoliensinine (Isoliensinine, compound 2), neferine (Neferine, chemical combination
Object 3) demethyl isoliensinine (Norisoliensinine, compound 4) 6- hydroxyl demethyl isoliensinine (6-
Hydroxynorisoliensinine, compound 5) N- demethyl isoliensinine (N-Norisoliensinine, compound 6).
Specific structure is as follows:
Embodiment 2: the biomembrane Inhibition test of lotus nut alkaloid compound
Bacterium solution: pseudomonas aeruginosa 9027 (ATCC 9027), pseudomonas aeruginosa 27853 (ATCC 27853) and drug resistance
Pseudomonas aeruginosa (persister)
It tests compound: being positive right with furan ketone compound (Z) -4- bromo- 5- (bromine methylene) -2 (5H)-furanone
According to using DMSO as negative control, the lotus nut alkaloid compound of positive drug and the compound of the present invention 1-6 are configured to respectively
32、64、128μg/mL。
Experimental method: being separately added into the test compound that 100 μ L are prepared into orifice plate, is inoculated with 100 μ L bacterium solutions.Setting is empty
White control group (200 μ L of LB culture medium) and negative control group (LB culture medium and each 100 μ L of bacterium solution).It is placed in 37 DEG C of incubators and incubates
Change.After 20h, hole endosexine bacterium solution is drawn, distillation water washing three times, washes away planktonic bacteria and is added after the drying of dry or baking oven
The crystal violet that 220 μ L concentration are 1%, is placed at room temperature for 30min, then distilled water carefully washs 3 times；230 μ L, 95% ethyl alcohol is added
Biomembrane-crystal violet compound is dissolved, orifice plate absorbance value is measured at microplate reader 630nm wavelength, is measured in parallel three times, as a result sees
Table 1.
Inhibiting effect of the 1 lotus nut alkaloid compound of table for three kinds of aeruginosa biofilms
The inhibition assay result of above-mentioned three kinds of aeruginosa biofilms shows lotus nut bases chemical combination of the present invention
Object all has inhibitory effect for the biomembrane of three kinds of pseudomonas aeruginosas, it is shown that lotus nut alkaloid compound of the invention can be with
Intervention school-based by inhibiting bacterium reaches the life that can not inhibit bacterium while reducing bacterial virulence and pathogenicity
It is long, it is not likely to produce the effect of bacterial drug resistance.Especially compound 1-6 is for pseudomonas aeruginosa and tolerant Pseudomonas aeruginosa
Biomembrane all have more suitable than positive drug furan ketone compound or better inhibitory effect, show lotus nut bases of the present invention
Compound all has good inhibitory effect for pseudomonas aeruginosa and tolerant Pseudomonas aeruginosa.
Embodiment 3: resisting pseudomonas aeruginosa granule
1 10mg of compound
Lactose 15mg；
10% starch slurry 3mg；
The preparation step of resisting pseudomonas aeruginosa granule are as follows:
(1) compound 1 first with lactose mixing 10-15 minutes；
(2) 10% starch slurry softwood is added, crosses 14 meshes, it is dry after granulation；
(3) 12 meshes are crossed, are dried after whole grain to get resisting pseudomonas aeruginosa granule.
Embodiment 4: resisting pseudomonas aeruginosa capsule
The preparation step of resisting pseudomonas aeruginosa capsule are as follows:
(1) compound 2 first with lactose mixing 10-15 minutes；
(2) it is mixed 10-15 minutes after adding microcrystalline cellulose；
(3) it is mixed 3-5 minutes after adding talcum powder；
(4) mixture is packed into gelatine capsule shell to get resisting pseudomonas aeruginosa capsule.
Embodiment 5: overriding resistance pseudomonas aeruginosa tablet
The preparation step of overriding resistance pseudomonas aeruginosa tablet are as follows:
(1) compound 3 first with lactose mixing 10-15 minutes；
(2) 10% starch slurry softwood is added, crosses 14 meshes, it is dry after granulation, cross 12 mesh sieves；
(3) crospovidone and magnesium stearate is then added, mixes 3-5 minutes；
(4) after mixing tabletting to get overriding resistance pseudomonas aeruginosa tablet.
Embodiment 6: resisting pseudomonas aeruginosa granule
4 15mg of compound
Lactose 20mg；
10% starch slurry 4mg；
The preparation step of resisting pseudomonas aeruginosa granule are as follows:
(1) compound 4 first with lactose mixing 10-15 minutes；
(2) 10% starch slurry softwood is added, crosses 14 meshes, it is dry after granulation；
(3) 12 meshes are crossed, are dried after whole grain to get resisting pseudomonas aeruginosa granule.
Embodiment 7: resisting pseudomonas aeruginosa capsule
The preparation step of resisting pseudomonas aeruginosa capsule are as follows:
(1) compound 5 first with lactose mixing 10-15 minutes；
(2) it is mixed 10-15 minutes after adding microcrystalline cellulose；
(3) it is mixed 3-5 minutes after adding talcum powder；
(4) mixture is packed into gelatine capsule shell to get resisting pseudomonas aeruginosa capsule.
Embodiment 8: overriding resistance pseudomonas aeruginosa tablet
The preparation step of overriding resistance pseudomonas aeruginosa tablet are as follows:
(1) compound 6 first with lactose mixing 10-15 minutes；
(2) 10% starch slurry softwood is added, crosses 14 meshes, it is dry after granulation, cross 12 mesh sieves；
(3) crospovidone and magnesium stearate is then added, mixes 3-5 minutes；
(4) after mixing tabletting to get overriding resistance pseudomonas aeruginosa tablet.
The biomembrane Inhibition test of 9: six kinds of compound formulations of embodiment
1 granule of compound of the preparation of Example 3,2 Capsule content of compound of the preparation of embodiment 4, embodiment 5
5 Capsule content of compound prepared by 3 tablet of compound obtained, 4 granule of compound for applying the preparation of example 6, embodiment 7,
6 tablet of compound made from embodiment 7, tests its inhibitory activity to biomembrane respectively, specific testing procedure with embodiment 2,
Test result is shown in Table 2.
Inhibiting effect of the 2 lotus nut alkaloid compound of table for three kinds of aeruginosa biofilms
The preparation of compound 1-6 has the biomembrane of pseudomonas aeruginosa and tolerant Pseudomonas aeruginosa as the result is shown
There is more suitable than positive drug furan ketone compound or better inhibitory effect, shows lotus nut alkaloid compound of the present invention for copper
Green pseudomonad and tolerant Pseudomonas aeruginosa all have good inhibitory effect.
The foregoing is merely the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, under the premise of not departing from raw material of the present invention, several improvements and modifications can also be made, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (7)
1. lotus nut alkaloid compound is in the application of preparation pseudomonas aeruginosa and tolerant Pseudomonas aeruginosa inhibited in drug；
The lotus nut alkaloid compound is the compound with structure shown in Formulas I,
Wherein, described R1, R2, R3, R4, R5 are independently selected from hydrogen or methyl.
2. application according to claim 1, which is characterized in that the lotus nut alkaloid compound is in following compound 1-6
At least one:
3. application according to claim 1, which is characterized in that the drug includes the lotus nut bases chemical combination of effective dose
Object.
4. application according to claim 3, which is characterized in that the drug further includes pharmaceutically acceptable auxiliary material.
5. applying according to claim 3, which is characterized in that the drug is oral preparation or ejection preparation.
6. applying according to claim 5, which is characterized in that the oral preparation is tablet, capsule, granule；It is described
Ejection preparation is injection or powder-injection.
7. application according to claim 1, which is characterized in that the drug its by 10%-90% lotus nut bases chemical combination
The pharmaceutically acceptable auxiliary material of object and 10%-90% composition.
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