CN107929742A - The anti-infective pharmaceutical applications of hordenine or its joint antibiotic - Google Patents
The anti-infective pharmaceutical applications of hordenine or its joint antibiotic Download PDFInfo
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- CN107929742A CN107929742A CN201711362771.5A CN201711362771A CN107929742A CN 107929742 A CN107929742 A CN 107929742A CN 201711362771 A CN201711362771 A CN 201711362771A CN 107929742 A CN107929742 A CN 107929742A
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- hordenine
- quorum sensing
- biofilm
- bacteria
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
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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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
Abstract
The invention discloses a kind of new purposes of natural products hordenine, and in particular to is preparing the application in preventing and treating bacterium infection medicine to compound hordenine, is being mainly manifested in：Hordenine can substantially suppress the synthesis of the signaling molecule of quorum sensing regulation and control, and hordenine can substantially suppress the expression of the virulence factor of quorum sensing regulation and control, and hordenine can substantially suppress the expression of quorum sensing related gene.In addition, hordenine can substantially suppress the generation of biofilm with antibiotic Netilmicin drug combination, established biofilm can be substantially destroyed, is expected to become the novel anti-infection agent of prevention and treatment bacterium infection.
Description
Technical field
The invention belongs to medical science, more particularly to hordenine or the anti-infective pharmaceutical applications of its joint antibiotic.
Background technology
Hordenine (CAS registration numbers：It is 539-15-1) a kind of natural phenolic compound, is present in germinating barley seed
Root, the legume hair root of pod beggarweed, the stem of linden leaf beggarweed, the heartwood etc. of triangular dendrolobium herb or root, also can be artificial synthesized,
Commercialization.Its structural formula is as follows：
The security of hordenine is higher, have relaxation bronchial smooth muscle, vasoconstriction, vasopressors, rise blood pressure and
The effect of excited maincenter, available for alleviation bronchitis and bronchial asthma.But up to the present, it yet there are no on hordenine
The relevant report of anti-infective research.
Due to the abuse of antibiotic, the multiple antibiotic resistant strain of clinical discovery is more and more, the shape of biofilm (Biofilm)
Into being first of barrier causing bacterium multidrug resistant.Under the protection of bacterial biofilm, bacterium can strengthen itself confrontation
The tolerance of raw element, environmental pressure and host immune system attacks.A kind of approach for solving bacterial resistance at present is attenuation
(anti-virulence), i.e., bacterium is not being killed, is not inhibiting bacteria the generation of suppression virulence factor under conditions of growth, so that
Host is infected in reduction.In addition, the selection pressure of bacterium can be reduced by not inhibiting bacteria growth, so as to reduce bacterium generation
Drug resistance.Quorum sensing (Quorum sensing, QS) is the information interchange between a kind of bacterium, in the growth course of various bacteria
In play an important role.Current research shows that formation, development and the function point analysis of most bacterial biofilms need QS signals
Molecule participates in, therefore by disturbing bacterium QS signals to destroy bacterial biofilm, so that finally to solve by bacterium living beings quilt
Bacterial resistance problem caused by film provides brand-new Research Thinking.Pseudomonas aeruginosa (Pseudomonas aeruginosa) is
Gram-negative bacteria, and common clinical bacteria, its intervention school-based include las, rhl and pqs, are respectively synthesized signal
Molecule N- (3-oxododecanoyl)-L-homoserine lactone (3-oxo-C12-HSL), N-butanoyl-L-
Homoserine lactone (C4-HSL), quinolone (PQS).The a variety of virulence factors of pseudomonas aeruginosa such as protease
(Protease), elastoser (elastase), pyo (pyocyanin), rhamnolipid (rhamnolipid), sea
The synthesis of alginates (alginate) is regulated and controled by intervention school-based.Pseudomonas aeruginosa biofilm (biofilm)
Formed, and the motor behavior of bacterium is also regulated and controled be subject to intervention school-based.Except pseudomonas aeruginosa, remaining gram
Negative bacterium such as Escherichia coli, proteus, pneumobacillus, and the double balls of gram-positive bacteria such as staphylococcus aureus, pneumonia
The pathogenic and drug resistance of bacterium, clostridium tetani etc. is also perceptual related to colony.Therefore, quorum sensing inhibitor is in pre- bacteriological protection
Having a extensive future in terms of infection.
The content of the invention
Goal of the invention：The present invention provides hordenine or the anti-infective pharmaceutical applications of its joint antibiotic.
Technical solution：Hordenine answering in the medicine for improving or treating the infection relevant disease such as bacterium infection is prepared
With.
Further, the hordenine reaches anti-infective purpose by inhibiting bacteria biofilm and being formed.
Further, the hordenine is by inhibiting bacteria quorum sensing so as to inhibit bacteria biofilm.
Further, the hordenine can inhibit bacteria the synthesis of the signaling molecule of quorum sensing regulation and control, can
The expression of the virulence factor of quorum sensing regulation and control is inhibited bacteria, the expression of quorum sensing related gene can be inhibited bacteria.
Hordenine joint antibiotic is used to prepare improvement or treats in the medicine of the infection relevant disease such as bacterium infection
Application it is also within the scope of the present invention.
Further, the hordenine joint antibiotic can not only inhibit bacteria the synthesis of biofilm, additionally it is possible to
Further destroy the biofilm formed.
The Pathogenicity of Bacteria and drug resistance are perceptual related to colony, including Gram-negative bacteria such as Escherichia coli, deformation
Bacillus, pneumobacillus, and gram-positive bacteria such as staphylococcus aureus, Diplococcus pneumopniae, clostridium tetani etc..
The experimentation and result data of hordenine resisting pseudomonas aeruginosa infection are listed in the embodiment of the present invention,
In drug combination, using hordenine joint antibiotic Netilmicin resisting pseudomonas aeruginosa infection.Netilmicin is
Aminoglycoside antibiotics, therefore, hordenine can also be big mould with other aminoglycoside antibiotics such as tobramycin, celebrating
The drug combinations such as element, amikacin, prevent and treat Gram-negative bacteria such as pseudomonas aeruginosa, Escherichia coli, pneumobacillus
Caused infection.
Beneficial effect：(1) present invention firstly discovers that hordenine has the function that to inhibit bacteria infection, and effective
The growth not inhibited bacteria under dosage；(2) present invention firstly discovers that hordenine can effectively suppress with Antibiotic combination medication
With destruction biofilm, it imply that it with before the clinical practice for preferably preventing and treating the infection relevant disease such as bacterium infection
Scape.
Brief description of the drawings
Fig. 1 is the influence for the signaling molecule synthesis that hordenine regulates and controls quorum sensing；
Fig. 2 is the influence for the virulence factor expression that hordenine regulates and controls quorum sensing；
Fig. 3 is the inhibitory action of expression of the hordenine to quorum sensing related gene；
Fig. 4 is the formation that hordenine suppresses biofilm with antibiotic Netilmicin drug combination；
Fig. 5 is that hordenine destroys established biofilm with antibiotic Netilmicin drug combination.
Embodiment
The application is explained in detail with reference to specific embodiment.
Medicine：Hordenine used in this experiment is obtained by the root separation and Extraction of the barley seed to germinate, art technology
The hordenine that personnel use can be purchased directly in Nanjing Jing Zhu bio tech ltd.
Reagent：Congo red, azo-casein, orcin, NB culture mediums, TSB culture mediums are purchased in Shanghai bioengineering stock
Part Co., Ltd, other reagents are commercially available analytical reagents.
Bacterial strain：Pseudomonas aeruginosa PAO1 is awarded by the Gong Qian Red Sect of Lamaism of Chinese Marine University and given.
Embodiment 1
The synthesis of the signaling molecule of quorum sensing regulation and control：Inoculation pseudomonas aeruginosa PAO1 single bacteriums are fallen in NB culture mediums,
37 DEG C, 150rmp is incubated overnight.Adjust OD620=0.5, the 50 μ L of bacterium solution for mixing up OD are taken with 1:1000 are added to 50mLNB culture mediums
In, while the hordenine of various concentrations is added, 37 DEG C, 200rpm cultures 48h.12,000rpm, 4 DEG C of centrifugation 10min, supernatant
The ethyl acetate (containing 0.5% formic acid) of the acidifying of liquid same volume extracts 3 times, 35 DEG C of evaporated under reduced pressure, and dried object methanol is molten
Solution, LC/MS/MS measure the content of signaling molecule.The species of signaling molecule is determined according to ion fragment peak and retention time, according to
Peak area carries out the measure of relative amount.Result of the test is as shown in Figure 1, wherein A (a) is the MS/MS matter of signaling molecule C4-HSL
Spectrogram, A (b) are the MS/MS mass spectrograms of signaling molecule 3-O-C12-HSL, and B (a, b) is signaling molecule standard items C4-HSL and 3-
The chromatograms of O-C12-HSL, B (c) be DMSO control groups signaling molecule C4-HSL and 3-O-C12-HSL chromatograms, B
(d-f) it is respectively 0.5,0.75 and 1.0mg mL-1The liquid of the signaling molecule C4-HSL and 3-O-C12-HSL of hordenine treatment group
Phase collection of illustrative plates.C and D is 0.5,0.75 and 1.0mg mL respectively-1Signaling molecule C4-HSL and 3-O-C12- after hordenine processing
The relative amount of HSL.**,p<0.01, vs Control, * * *, p<0.001, vs Control (SPSS 18.0), thus may be used
See, there is the synthesis of the obvious signaling molecule for suppressing quorum sensing regulation and control of hordenine processing, hordenine good colony to feel
Inhibitory activity is answered, the synthesis of colony induction signaling molecule can be inhibited bacteria well, effective dose is 0.5-1.0mg mL-1。
Embodiment 2
The influence of expression to the virulence factor of quorum sensing regulation and control：Inoculation pseudomonas aeruginosa PAO1 single bacteriums fall on NB trainings
Support in base, 37 DEG C, 150rmp is incubated overnight.Adjust OD620=0.5, the 50 μ L of bacterium solution for mixing up OD are taken with 1:1000 are added to 50mLNB
In culture medium, while the hordenine of various concentrations is added, using DMSO as negative control, resveratrol (RES) is positive control.
37 DEG C, 200rpm cultures 24h, 12,000rpm, 4 DEG C of centrifugation 10min.
The measure of proteinase activity：(weighing 100mg azo-caseins, to be dissolved in 5mL dense for the azo-casein solution of configuration 2%
The Tris/HCl for 50mM is spent, 4 DEG C save backup), take the 250uL solution to be mixed with 150uL PA01 filtrates, in 4 DEG C of placements
4h, then adds the trichloroacetic acid that 1.2mL concentration is 10% and terminates reaction, 4 DEG C of standing 15min after mixing, and then 10,000rpm
10min is centrifuged, abandons precipitation, takes supernatant to add the NaOH of 1.4mL 1M, 0D is surveyed after fully mixing440。
Result of the test：From Fig. 2A, compared with positive control resveratrol, 0.5,0.75 and 1.0mg mL-1Barley
Bud alkali can significantly inhibit proteinase activity, and with the increase of hordenine concentration, the increase of its inhibitory activity.
The measure of elastase activity：Take the 100 above-mentioned supernatants of μ L to mix with 900 μ L elastin laminins enzyme buffer liquids (to contain
Congo red 20mg, 100mM Tris-HCl, 1mM CaCl2, pH 7.5), 37 DEG C, 180rpm concussion reactions 3h, 10,000rpm from
Heart 10min removes insoluble Congo red, absorption supernatant microplate reader survey 0D495。
Result of the test：From Fig. 2 B, compared with positive control resveratrol, 0.5,0.75 and 1.0mg mL-1Barley
Bud alkali can significantly inhibit elastase activity, and with the increase of hordenine concentration, the increase of its inhibitory activity.
The measure of pyo content：The above-mentioned filtrates of 5mL are taken to be mixed with 3mL chloroforms, aqueous phase discarded after standing, adds
1mL 0.2M HCl, fully mix, and 10,000g centrifugation 5min, taking-up is pink to arrive wine-colored upper solution, it is surveyed with microplate reader
Absorbance at 520nm.
Result of the test：From Fig. 2 C, compared with positive control resveratrol, 0.5,0.75 and 1.0mg mL-1Barley
Bud alkali can significantly inhibit the generation of pyo, and with the increase of hordenine concentration, the increase of its inhibitory activity.
The measure of rhamnolipid content：Draw above-mentioned filtrate 300uL and add 2mL centrifuge tubes, add 600uL ether extraction 2
It is secondary, 2min is shaken, 2min is stood, treats that organic phase is separated from the water, organic phase, ventilating kitchen or nitrogen evaporator drying is carefully drawn, adds
Enter the dissolving of 100uL distilled water, add 60% concentrated sulfuric acids of 800uL and the orcin of 100uL 1.6%, 80 DEG C of reaction 30min, fill
After dividing cooling, reaction solution 200uL, microplate reader detection OD are drawn421。
Result of the test：From Fig. 2 D, compared with positive control resveratrol, 0.5,0.75 and 1.0mg mL-1Barley
Bud alkali can significantly inhibit the generation of rhamnolipid, and with the increase of hordenine concentration, the increase of its inhibitory activity.
The measure of alginate content：Take the above-mentioned filtrates of 70uL and 600uL boric acid/sulfuric acid (4:1) 10s, is mixed.Mixed liquor
It is placed in 55 DEG C of water-bath 30min, microplate reader detection OD530。
Result of the test：From Fig. 2 E, compared with positive control resveratrol, 0.5,0.75 and 1.0mg mL-1Barley
Bud alkali can significantly inhibit the generation of alginate, and with the increase of hordenine concentration, the increase of its inhibitory activity.
The measure of siderophore activity：Above-mentioned filtrate detects OD with 10 times of dilutions of Tris-HCl (pH 7.4), microplate reader405。
Result of the test：From Fig. 2 F, compared with positive control resveratrol, 0.5,0.75 and 1.0mg mL-1Barley
Bud alkali can significantly inhibit siderophore activity, and with the increase of hordenine concentration, the increase of its inhibitory activity.
Motor ability test：Inoculation pseudomonas aeruginosa PAO1 single bacteriums are fallen in NB culture mediums, 37 DEG C, 150rmp trains overnight
Support.Take 2 μ L bacterium solutions points to swimming culture mediums (peptone 1g, NaCl 0.5g, agar 0.3g, water 100mL, pH 7.2) and
Swarming culture mediums (NB culture medium 0.8g, glucose 0.5g, agar 0.5g, distilled water 100mL, pH7.2) center.37
DEG C overnight incubation.DMSO and resveratrol make negative and positive control respectively.
Result of the test：From Fig. 2 G and Fig. 2 H, compared with positive control resveratrol, hordenine can significantly inhibit
Swimming and swarming.
Embodiment 3
The influence of expression to quorum sensing related gene：Inoculation pseudomonas aeruginosa PAO1 single bacteriums fall on NB culture mediums
In, 37 DEG C, 150rmp is incubated overnight.Adjust OD620=0.5, the 50 μ L of bacterium solution for mixing up OD are taken with 1:1000 are added to 50mLNB cultures
In base, while the hordenine of various concentrations is added, using DMSO as negative control.37 DEG C, 200rpm cultures 24h.According to
The method extraction total serum IgE that RNeasy Mini Kit kits (Tiangeng biology, Beijing) are introduced, is tried according to RNeasy Mini Kit
The method of agent box introduction carries out RNA reverse transcription experiments, sets the primer of lasI, lasR, rhlI, rhlR and reference gene rpsL
(as shown in table 1)
1 experiment primer of table
Table 1Primers used in this study
(1) basisPremix Ex TaqTM (Tli RnaseH Plus) kit establishes qRT-PCR reaction systems,
As shown in table 2
Table 2qRT-PCR reaction systems
Table 2qRT-PCR reaction
(2) RT-PCR experiments are carried out with Applied Biosystems 7300Real-time PCR System, reaction follows
Ring parameter is as follows：95 DEG C, 30s；95 DEG C, 5s, 58 DEG C, 30s, 72 DEG C, 30s；95 DEG C, 15s, 60 DEG C, 30s；Experiment need to repeat three
Secondary, each experiment need to set four repetitions.
Result of the test：From the figure 3, it may be seen that after hordenine processing, quorum sensing related gene lasI, lasR, rhlI, rhlR
It is remarkably decreased.
Embodiment 4
Biofilm suppresses experiment：Inoculation pseudomonas aeruginosa PAO1 single bacteriums are fallen in NB culture mediums, 37 DEG C, 150rmp mistakes
Night cultivates.Adjust OD620=0.5, the 50 μ L of bacterium solution for mixing up OD are taken with 1:1000 are added in 50mL TSB culture mediums, add at the same time
The hordenine of various concentrations, using DMSO as negative control.37 DEG C of quiescent culture 24h.Supernatant is sopped up, is washed with water 3 times, 60 DEG C of bakings
It is dry；Add 200uL methanol and fix 15min, 60 DEG C of drying；The violet staining 15min that 200uL concentration is 0.05% is added, is inhaled
Unnecessary crystal violet is gone, is washed 3 times, 60 DEG C of drying；Add 200uL absolute ethyl alcohols, 37 DEG C, 180rpm decolorations 30min；Draw
120uL surveys OD570.Hordenine (Hor) and antibiotic Netilmicin (Net) drug combination suppress the formation of biofilm according to
The above method carries out.Hordenine and Netilmicin (0.4 μ g mL-1) independent medication or drug combination be in nutrient solution to swimming
The influence of bacterium carries out bacterium colony counting using the method for tablet coating, is shown for the inhibitory action of biofilm using scanning electron
Micro mirror, carries out fluorescence microscope with reference to fluorescent staining and is observed.
Result of the test：From Fig. 4 A, 0.5,0.75,1.0mg mL-1Hordenine processing, the formation of biofilm is bright
It is aobvious to reduce, it can be good at suppressing the formation of biofilm with antibiotic Netilmicin drug combination, while according to Fig. 4 B
Hordenine has no significant effect the viable count in nutrient solution with Netilmicin drug combination under effective dose.Fluorescence microscopy
Mirror (Fig. 4 C) and scanning electron microscope (Fig. 4 D) further demonstrate above-mentioned conclusion.
Embodiment 5
The failure test of biofilm：Inoculation pseudomonas aeruginosa PAO1 single bacteriums are fallen in NB culture mediums, 37 DEG C, 150rmp
It is incubated overnight.Adjust OD620=0.5, the 50 μ L of bacterium solution for mixing up OD are taken with 1:1000 are added in 50mL TSB culture mediums, and 37 DEG C quiet
Put culture 24h.Supernatant is sopped up, is washed with water 3 times, adds the fresh TSB culture mediums of the hordenine containing various concentrations, 37 DEG C of standings
Cultivate 48h.Supernatant is sopped up, is washed with water 3 times, 60 DEG C of drying；Add 200uL methanol and fix 15min, 60 DEG C of drying；Add 200uL
Concentration is 0.05% violet staining 15min, sucks unnecessary crystal violet, is washed 3 times, 60 DEG C of drying；It is anhydrous to add 200uL
Ethanol, 37 DEG C, 180rpm decolorations 30min；Draw 120uL and survey OD570.Hordenine is broken with antibiotic Netilmicin drug combination
Bad established biofilm carries out according to the method described above.Hordenine and Netilmicin (0.4 μ g mL-1) independent medication or
Influence of the drug combination to planktonic bacteria in nutrient solution, and viable bacteria content in biofilm using tablet coating method into
Row bacterium colony counts, and the destruction for biofilm uses scanning electron microscope, with reference to laser co-focusing electron microscope
Observed.
Result of the test：From Fig. 5 A, 0.5,0.75,1.0mg mL-1Hordenine processing can substantially destroy and formed
Biofilm, with antibiotic Netilmicin drug combination, the destruction of biofilm significantly increases.From Fig. 5 B, greatly
Hordenine is used alone and can be significantly reduced with Netilmicin drug combination the viable count in envelope；From Fig. 5 C, greatly
Hordenine has no significant effect the viable count in nutrient solution with Netilmicin drug combination.Scanning electron microscope (Fig. 5 D) table
The content of bright biofilm is reduced, loosely organized, and laser confocal scanning electron microscope (Fig. 5 E) shows the thickness of biofilm
Degree substantially reduces, and content reduces.
Claims (8)
1. application of the hordenine in the medicine for improving or treating the infection relevant disease such as bacterium infection is prepared.
2. apply according to claim 1, it is characterised in that the hordenine inhibits bacteria biofilm.
3. apply according to claim 2, it is characterised in that the hordenine inhibits bacteria quorum sensing.
4. apply according to claim 3, it is characterised in that the hordenine inhibits bacteria the signal of quorum sensing regulation and control
The synthesis of molecule.
5. apply according to claim 3, it is characterised in that the hordenine inhibits bacteria the virulence of quorum sensing regulation and control
The expression of the factor.
6. apply according to claim 3, it is characterised in that the hordenine inhibits bacteria quorum sensing related gene
Expression.
7. hordenine joint antibiotic is used to prepare improvement or treats in the medicine of the infection relevant disease such as bacterium infection
Using.
8. apply according to claim 7, it is characterised in that the hordenine joint antibiotic can inhibit bacteria biology
Envelope forms, destroys the biofilm formed.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110063948A (en) * | 2019-05-14 | 2019-07-30 | 福建师范大学 | P-hydroxyphenylethanol is used to prepare the purposes for inhibiting the drug of bacterial community induction |
| WO2020233138A1 (en) * | 2019-05-22 | 2020-11-26 | Wang Xiong | Use of hordenine in preparing drug for treating hypophysoma |
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| CN103483209A (en) * | 2013-09-13 | 2014-01-01 | 陕西嘉禾植物化工有限责任公司 | Hordenine synthesis method |
Non-Patent Citations (2)
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| AME´ LIE BEURY-CIROU ET AL.: ""At a Supra-Physiological Concentration, Human Sexual Hormones Act as Quorum-Sensing Inhibitors"", 《PLOS ONE》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110063948A (en) * | 2019-05-14 | 2019-07-30 | 福建师范大学 | P-hydroxyphenylethanol is used to prepare the purposes for inhibiting the drug of bacterial community induction |
| WO2020233138A1 (en) * | 2019-05-22 | 2020-11-26 | Wang Xiong | Use of hordenine in preparing drug for treating hypophysoma |
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