CN106822068A - The new lignin compound of triphenyl is preparing the application of antibacterials - Google Patents
The new lignin compound of triphenyl is preparing the application of antibacterials Download PDFInfo
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- CN106822068A CN106822068A CN201710025952.2A CN201710025952A CN106822068A CN 106822068 A CN106822068 A CN 106822068A CN 201710025952 A CN201710025952 A CN 201710025952A CN 106822068 A CN106822068 A CN 106822068A
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- antibacterials
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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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
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Abstract
The invention discloses the application of the new lignin compound of natural products triphenyl, it is related to safflower anise alcohol, application of the great Hua anise alcohol in antibacterials are prepared, belongs to pharmaceutical technology field.Such compound has phenolic hydroxyl group and pi-allyl substitution base, and general structure is as follows, and its gram-positive cocci to MDR has strong bacteriostatic activity especially for MRSA.。
Description
Technical field
The present invention relates to the application of the new lignin compound of triphenyl, more particularly to contain safflower anise alcohol, great Hua eight
Angle alcohol and its derivative are application of the active ingredient in antibacterials are prepared, and belong to pharmaceutical technology field.
Background technology
Staphylococcus aureus (the Methicillin-resistant Staphylococcus of methicillin-resistant
Aureus, MRSA) it is one of the important pathogen for causing hospital and Community Acquired Infections, pneumonia, septic joint can be caused
Various lethal infections such as inflammation, osteomyelitis, meningitis and endocarditis.Especially Hospital-acquired MRSA (hospital-
Acquired MRSA, HA-MRSA), extreme difficulties are brought to treatment with the characteristics of easily propagation based on its multidrug resistant.At present only
Several class medicines such as glycopeptides vancomycin and oxazolidinones Linezolid are effective to its.Therefore some scholars are also by MRSA
The big infectious diseases in the world three is listed as with hepatitis B, AIDS.There is data to show, the U.S. is every year because MRSA infection causes extremely
Summation of patient's number equivalent to AIDS, tuberculosis and virus hepatitis died.Although vancomycin, Linezolid, Daptomycin
Ratify to be infected for clinical treatment MRSA through U.S. FDA with a small number of medicines such as tigecycline, but clinically have found in recent years
The antibody-resistant bacterium of medicine is stated, and the probability got gradually increases, therefore the research and development of new anti-MRSA infection medicines seem particularly urgent
Cut.
Safflower anise alcohol, great Hua anise alcohol is isolated a kind of triphen from Illicium (Illicium) plant stem-leaf
The new lignin compound of base.It extracts lock out operation simplicity, therefore is had into by its antibacterials for producing or derivatives thereof
This is low, the characteristics of safe.The relevant report for being applied to and preparing in antibacterials is had no at present.
The content of the invention
Contain compound safflower anise alcohol (Dunnianol) or great Hua anise alcohol present invention aim at providing
(Macranthol) for the medicine of active ingredient is preparing treatment methicillin-resistant staphylococcus aureus and multidrug resistance gold
Application in staphylococcus aureus medicine.
To realize the object of the invention, the present inventor is right on the basis of long campaigns antimicrobial natural Drug development and research
The preferable medicinal plant of several antibacterial activities of primary dcreening operation carries out tracking activity, and therefrom isolated 2 have notable antibacterial activity
Natural products safflower anise alcohol, great Hua anise alcohol.It was found that safflower anise alcohol, great Hua anise alcohol and its derivative as effectively into
Divide has preferable effect in treatment methicillin-resistant staphylococcus aureus and multidrug resistance staphylococcus aureus.
The new lignin compound of triphenyl described in the present invention is safflower anise alcohol, great Hua anise alcohol and its derivative,
Its chemical general formula is as follows：
Wherein R1It is H or OH, R2It is H or OH.
It is preferably as follows formula (1), (2) compound：
Safflower anise alcohol, great Hua anise alcohol extracting methods：In typical separation method, by the plant comprising the compound
Crushed together with one or more organic reagent to form one or more plant extracts, then purify the extract to obtain
Compound.The compounds of this invention derives from anistree platymiscium, particularly is derived from the wild anise (Illicium of Illicium plant species
Simonsii), safflower anise (Illicium dunnianum) or middle extraction of mountain of papers anise (Illicium tsaii) separate
Arrive.Other Illicium plant species such as Central China anise (Illicium fargesii) can also be used for extracting the compounds of this invention.
The present invention separates safflower anise alcohol, great Hua anise alcohol from natural origin.The preparation side that the compounds of this invention is used
Method is recognized technology, can be found in various documents.
For gram positive bacterial strain, particularly MRSA and penicillin resistant dissociant aspect, chemical combination of the present invention
Thing has has a more preferable activity than prior art, such as to the activity of the multidrug resistance bacterial strain of bacterium.Carried out in inventor
In experiment, it is found that the compound has the bacterium to beta-lactam, macrolide, FQNS and Tetracyclines resistance
Remarkable activity of the strain in interior all multidrug resistance bacterial strains.This compound can directly be used, or with pharmaceutical composition
Form use.The pharmaceutical composition contains mass percent 0.1-99% the compounds of this invention, preferably 0.5-90%, remaining
For pharmaceutically pharmaceutical acceptable carrier acceptable, nontoxic to humans and animals and inert and/or excipient.
Described pharmaceutical carrier or excipient is one or more solid, semi-solid and liquid diluent, filler and medicine
Tetramune assistant agent.Pharmaceutical composition of the present invention is used in the form of per weight dose or plastics.Safflower anise alcohol, greatly
The composition of anistree alcohol and its derivative is spent to be prepared into various formulations using the method that pharmaceutical field is generally acknowledged.Such as liquid preparation (note
Penetrate liquid, supensoid agent, emulsion, solution, syrup etc.), solid pharmaceutical preparation (tablet, capsule, granule, electuary etc.), spray, gas
Mist agent, ointment etc..Medicine of the invention can be through injection (intravenous injection, drip-feed, intramuscular injection, intraperitoneal injection, subcutaneous note
Penetrate) and the method for administration such as oral, sublingual administration, mucous membrane dialysis carry out the treatment of bacterium infection.
Advantage of the present invention：Gained safflower anise alcohol, great Hua anise alcohol and its derivative are isolated from phytochemicals production, show
Go out the antibacterial activity to gram-positive cocci, especially for the methicillin-resistant staphylococcus aureus of clinical trials difficult
The staphylococcus of (Methicillin-resistant Staphylococcus aureus, MRSA) and MDR.As
Active ingredient is applied preparing treatment methicillin-resistant staphylococcus aureus and multidrug resistance staphylococcus aureus
There is preferable effect in medicine.Be conducive to the research and development of new anti-MRSA infection medicines.
Brief description of the drawings
Fig. 1 is bacteriostatic activity test of the medicine of the present invention to S. aureus L-forms sensitive strain, in figure：A- safflowers anise alcohol, B- great Hua
Anistree alcohol, C- vancomycins, D-DMSO；
Fig. 2 is bacteriostatic activity test of the medicine of the present invention to MRSA clinical strains, in figure：A- safflowers anise alcohol, B- great Hua eight
Angle alcohol, C- vancomycins, D-DMSO.
Specific embodiment
It is that the present invention is better described, it is as follows for embodiment：
Embodiment 1：Safflower anise alcohol (1), the extraction separation and purification of great Hua anises alcohol (2)：
The wild anise cauline leaf of collection, dries in the shade, and its scientific name is identified as Illicium simonsii Maxim., crushes.Take
The open country anise cauline leaf that 7.0kg dries in the shade, crushes, is extracted 3 times, each 40L, 3 hours every time with the alcohol reflux of mass percent 95%,
Filtered fluid is concentrated into small size, and the 3L that adds water makes suspension, is extracted with chloroform (3L × 3) and n-butanol (3L × 4) respectively, vacuum distillation
Obtain chloroform portion (300g) and n-butanol fraction (300g).
Chloroform portion (134g) is adsorbed in 300g silica gel after being dissolved with chloroform/methanol, room temperature volatilize after through silica gel column chromatography
(1kg, 9.5 × 40cm, column volume 1500mL), chloroform/methanol (100: 0,95: 5,90: 10,80: 20,70: 30,60: 40,0:
100) gradient elution, is a flow point per 1500mL.Through silica gel tlc inspection, merge identical stream part, obtain 9 flow points (A-I).It is right
Each flow point carries out further screening active ingredients discovery, and flow point E activity is most strong.
Further chemical composition separation is carried out to flow point E.Flow point E (16.0g) is adsorbed in after being dissolved with chloroform/methanol
20g silica gel, weighs 200g silica gel and fills post (4 × 40cm), with chloroform/acetone (95：5,85：15,70：30) for eluent gradient is washed
It is de- to obtain five flow points (E-1-E-5).E-4 (10g) is with petroleum ether/acetone (95：5) for eluant, eluent through silicagel column (4 × 55cm,
Flow point E-3-2 270g) is obtained, then (petroleum ether is purified repeatedly through silicagel column：Acetone=90：10) compound 1 (2g), chemical combination are obtained
Thing 2 (0.2g).
Structure determination：Optically-active is determined by JASCODIP-370 polarimeters；Infrared spectrum (IR) uses KBr pressed disc methods, by
Bio-Rad FTS-135 type infrared spectrometers；Nuclear magnetic resoance spectrum (1H-、13C-NMR, DEPT) with Brucker AM-400 types and
DRX-500 types NMR spectrometer with superconducting magnet is determined, TMS (tetramethylsilane) makees internal standard；Mass spectrum (MS) uses VGAutospec-3000 types
Mass spectrograph is determined；Thin-layer chromatography silica gel, column chromatography silica gel (200-300 mesh) are purchased from Qingdao Haiyang Group Co., Ltd.
UV (methyl alcohol)：λmax(1og ε)=320 (2.39), 295 (2.69), 216 (3.41).
IR (KBr)：IR vmax(KBr)cm-1：3250,3070,2975,2870,1640,1498,1405.
EI-MS m/z (%):398([M]+, 100), 369 (15), 316 (20), 298 (18).
1H-NMR (500MHz, CDCl3)：δ:7.13 (2H, s, H-3, H-5), 7.11 (2H, d, J=10.0Hz, H-5', H-
5 "), 7.09 (2H, s, H-3', H-3 "), 6.85 (2H, d, J=10.0Hz, H-6', H-6 "), 6.00 (3H, m, H-8, H-8', H-
8 "), 5.95 (4H, m, H-9, H-9 "), 5.13 (2H, m, H-9), 3.37 (6H, d, J=8.5Hz, H-7, H-7', H-7 ").
13C-NMR (125MHz, CDCl3)δ:147.6 (s, C-1), 125.8 (s, C-2, C-6), 131.4 (d, C-3, C-5),
133.8 (s, C-4), 39.4 (t, C-7), 137.3 (d, C-8), 116.1 (t, C-9), 150.9 (s, C-1', C-1 "), 124.8
(s, C-2', C-2 "), 131.6 (d, C-3', C-3 "), 133.2 (s, C-4', C-4 "), 129.7 (d, C-5', C-5 "), 117.0
(d, C-6', C-6 "), 39.4 (t, C-7', C-7 "), 137.5 (d, C-8', C-8 "), 115.8 (t, C-9', C-9 ").
UV (methyl alcohol)：λmax(1og ε)=295 (2.73), 214 (3.28), 204 (3.29).
IR (KBr)：IR vmax(KBr)cm-1：3434,3217,1637,1498,1468,1174,913cm-1。
EI-MS m/z (%):398([M]+, 100), 369 (15), 316 (20), 298 (18).
1H-NMR (400MHz, CDCl3)δ:7.29 (1H, d, J=2.2Hz, H-2), 7.25 (1H, d, J=2.2Hz, H-6),
7.14 (1H, dd, J=8.1,2.2Hz, H-4 "), 7.10 (1H, d, J=2.2Hz, H-6 "), 7.04 (1H, d, J=2.2Hz, H-
6'), 7.03 (1H, overlaped, H-4'), 6.94 (1H, d, J=8.1Hz, H-3 "), 6.88 (1H, dd, J=7.2,1.8Hz,
H-3'), 6.05 (1H, m, H-8), 5.98 (1H, m, H-8 "), 5.93 (1H, m, H-8'), 5.17 (2H, m, H-9), 5.03-5.10
(2H, overlaped, H-9'), 5.03-5.10 (2H, overlaped, H-9 ").
13C-NMR (125MHz, CDCl3)δ:130.1 (s, C-1), 130.9 (d, C-2), 128.3 (s, C-3), 150.9 (s,
C-4), 124.8 (s, C-5), 130.0 (d, C-6), 35.0 (t, C-7), 136.2 (d, C-8), 116.7 (t, C-9), 127.5 (s,
C-1'), 150.8 (s, C-2'), 115.8 (d, C-3'), 128.9 (d, C-4'), 132.4 (s, C-5'), 130.3 (d, C-6'),
39.3 (t, C-7'), 137.4 (d, C-8'), 115.9 (t, C-9'), 123.3 (s, C-1 "), 151.2 (s, C-2 "), 116.8 (d,
C-3 "), 130.2 (d, C-4 "), 133.4 (s, C-5 "), 131.3 (d, C-6 "), 39.4 (t, C-7 "), 137.7 (d, C-8 "),
115.6 (t, C-9 ").
The safflower of embodiment 2. anise alcohol, the antibacterial activity in vitro experiment of great Hua anise alcohol
(1) K-B paper disk methods：
Experimental technique：With reference to U.S. clinical and laboratory standards institute (Clinical and Laboratory
Standards Institute, CLSI) method that is prepared on drug sensitive test paper of M02-A11 files, while preparing medicine of the present invention
With the drug sensitive test paper of positive control medicine vancomycin, scraps of paper drugloading rate is set to be 10 μ g/mL.Additionally, it is right to set solvent DMSO feminine genders
According to the scraps of paper.The drug sensitive test paper that will be prepared is affixed on coated staphylococcus aureus type strain ATCC 29213 and MRSA and faces respectively
On the MHA agar plates of bed strain JP-5, agar plate is inverted in 15min after placing the scraps of paper and is trained in placing it in 37 DEG C of incubators
Result, i.e. inhibition zone size are read after supporting 16-18 hours.
Experimental result：From visible (the safflower anise alcohol 0.49cm of Fig. 1 inhibition zone internal diameter sizes；Great Hua anise alcohol 0.46cm；Ten thousand
Ancient mycin：0.53cm), medicine safflower anise alcohol of the present invention and great Hua anise alcohol show and vancomycin to S. aureus L-forms sensitive strain
(first-line drug of the clinical treatment including the S. aureus L-forms infection including MRSA) suitable bacteriostatic activity.To MRSA clinical strains (Fig. 2)
Bacteriostatic activity (safflower anise alcohol 0.41cm；Great Hua anises alcohol 0.41cm) although being slightly weaker than vancomycin (0.58cm), but still
Show notable bacteriostatic activity.
(2) micro-broth dilution method minimum inhibitory concentration (Minimum Inhibitory Concentration,
MIC):
Experimental technique：With reference to CLSI M07-A9 files on dilution method sensitivity testing to antibacterials method standard, determine
Minimum inhibitory concentration of the medicine of the present invention to MRSA clinical strains.In the experiment, the lytic agent of medicine of the present invention is DMSO, diluent
It is pure water, DMSO final concentration≤1%；Test medicine dilution detection range is 8-0.015 μ g/mL；Staphylococcus aureus standard
Strain ATCC 29213 is Quality-control strains.Specific method is as follows：According to coubling dilution, by antibacterials stoste MH broth dilutions
Into 10 gradients, sequentially add before 96 porocyte culture plates in 10 holes, per the μ L of hole 100.Test strain is diluted with MH meat soups
Into 105CFU/mL, 10 holes add dilution bacterium solution 100 μ L before every row.11st hole adds 100 μ L MH meat soups to make negative control, the
12 holes add 100 μ L dilutions bacterium solution to make positive control.37 DEG C of 16~20h of culture, observe the growing state of bacterium in each hole nutrient solution,
Using the medicine highest dilution of bacteria growing inhibiting as the minimal inhibitory concentration (MIC) of testing drug.Every kind of medicine does 2 and puts down
OK.
Experimental result：From table 1, medicine of the present invention shows suitable with vancomycin good to MRSA clinical strains
Antibacterial activity.
The medicine of the present invention of table 1 is clinically separated the MIC (μ g/mL) of MRSA to 10 plants without repetition
The safflower of embodiment 3. anise alcohol, great Hua anise alcohol is tested mouse skin infection model in body antibacterial activity
Experimental technique：
Mouse adaptability is raised 1 week, period gives the mouse grain and water of abundance.Random 30 mouse of picking cut off after 1 week
Dorsal body setae, is anaesthetized with the chloraldurate 0.1ml/20g of mass percent 10%, 100 DEG C of constant temperature scald apparatus of postanesthetic mouse
Scald 10 seconds, it is 2.5cm to scald pressure 1000g scalding areas2；The MRSA clinical strains of picking incubated overnight, 37 DEG C of mistakes of 200rmp
Night cultivates, and takes 100 μ L bacterium solutions and scalds wound and smoothen in every mouse and is infected, repeated infection 11 times, after testing 30 it is small
Mouse all infects successfully.30 infecting mouses are randomly divided into 2 groups, every group 15, then every group of 15 mouse are randomly divided into 5
Group every group 3, respectively great Hua anise alcohol group, safflower anise alcohol group, vancomycin group, physiological saline group, 1%DMSO groups are small
It is administered after 24 and 48h of mouse infection infection, is administered once per 3h, successive administration 5 times, the μ g of each dosage 4 (100 μ L, the μ g/ of concentration 40
mL).Mouse is dislocated and put to death by the 15th hour after administration, around infection site of simply being sterilized with cotton ball soaked in alcohol, with being moistened with physiology
The cotton swab of salt solution scrapes infection site, takes fester in 1mL physiological saline, and 3000 leave the heart 5 minutes, abandons supernatant, then add 1mL lifes
The reason resuspended thalline of salt solution, mixes, and (S. aureus L-forms are in this plate to coat staphylococcus aureus chromogenic culture medium after dilution suitable multiple
Upper aobvious red, miscellaneous bacteria is colourless or blueness), read after 37 DEG C of culture 16-18h clump count (every group of parallel 3 pieces of coated plate of every mouse,
Clump count is taken the mean), observation continued administration postoperative infection position bacterium colony reduces number.
Experimental result：From table 2, medicine great Hua anise alcohol of the present invention and safflower anise alcohol, to mouse MRSA epidermis senses
Contaminate the therapeutic effect of model significantly, the clump count at mouse infection position can be significantly reduced, there is certain suppression to kill work to MRSA
Property.
Therapeutic effect of the medicine of the present invention of table 2 to mouse MRSA epidermis infection models
Embodiment 4：Parenteral solution
After the compounds of this invention 1 or compound 2 are dissolved with a small amount of DMSO, routinely add water for injection, refined filtration, embedding is gone out
Bacterium is made parenteral solution.
Embodiment 5：Tablet
The compounds of this invention 1 or compound 2 are 1 according to weight ratio with excipient:5 ratio adds excipient, granulation pressure
Piece, obtains tablet.
Embodiment 6：Capsule
The compounds of this invention 1 or compound 2 are 1 according to weight ratio with excipient:5 ratio adds excipient, is made glue
Capsule.
Embodiment 7：Ointment
The compounds of this invention 1 or compound 2 are 1 according to weight ratio with excipient:5 ratio adds excipient, is made soft
Paste.
Purposes of the invention and method are described by specific embodiment.Those skilled in the art can borrow
The links such as mirror present disclosure appropriate feed change, process conditions realize corresponding other purposes, and its correlation change all do not have
There is disengaging present disclosure, all similar replacements and change are it will become apparent to those skilled in the art that all
It is deemed to be included within the scope of the present invention.
Claims (6)
1. formula is contained（I）Application of the shown new lignin compound of triphenyl in antibacterials are prepared, it is characterised in that make
It is active component, is combined with pharmaceutical carrier and/or excipient for preparing antibacterials,
Wherein R1It is H or OH, R2It is H or OH.
2. the application of the new lignin compound of triphenyl according to claim in antibacterials are prepared, its feature exists
In choosing such as following formula（1）Or（2）Compound：
。
3. application of the new lignin compound of triphenyl according to claim 1 or claim 2 in antibacterials are prepared, its feature
Be be made into parenteral solution, supensoid agent, emulsion, solution, syrup or tablet, capsule, granule, electuary, spray,
Aerosol or ointment.
4. application of the new lignin compound of the triphenyl according to claim 1,2 or 3 in antibacterials are prepared, it is special
Levy and be, the antibacterials are resisting gram-positive bacteria infection medicine.
5. application of the new lignin compound of triphenyl in antibacterials are prepared according to claim 4, its feature exists
In the antibacterials are methicillin-resistant staphylococcus aureus resistance（MRSA）Or the staphylococcus medicine of anti-multidrug resistant
Thing.
6. application of the new lignin compound of triphenyl according to claim 1 or claim 2 in antibacterials are prepared, its feature
It is that it is wild anistree that the compound comes from anistree platymiscium（Illicium simonsii）, safflower anise（Illicium dunnianum）Or mountain of papers is anistree（Illicium tsaii）.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110776432A (en) * | 2019-11-07 | 2020-02-11 | 郑州大学 | Safflower octal mannich base derivative and preparation method and application thereof |
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| CN103083287A (en) * | 2013-01-11 | 2013-05-08 | 华侨大学 | Application of iIllicium macranthum alcohol in preparation of medicine for treating depression |
Non-Patent Citations (3)
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| JI-FENG LIU等: "Two New Phenylpropanoid Derivatives and Other Constituents from Illicium simonsii Active Against Oral Microbial Organisms", 《PLANTA MED》 * |
| 叶凤梅: "贡山八角枝叶中化学成分及抗菌抗肿瘤活性研究", 《中国优秀硕士学位论文全文数据库 医药卫生科技辑》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110776432A (en) * | 2019-11-07 | 2020-02-11 | 郑州大学 | Safflower octal mannich base derivative and preparation method and application thereof |
| CN110776432B (en) * | 2019-11-07 | 2023-03-21 | 郑州大学 | Safflower octal mannich base derivative and preparation method and application thereof |
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Application publication date: 20170613 |