CN107857786A - A kind of succinyl aurantiin and its application in terms of preparing antibacterial or treating medicine for treating osteoporosis - Google Patents
A kind of succinyl aurantiin and its application in terms of preparing antibacterial or treating medicine for treating osteoporosis Download PDFInfo
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Abstract
The invention discloses the medicine using the succinyl aurantiin described in following formula (1) as active component, and its application in terms of antibacterial, osteosporosis resistant medicament is prepared, belong to pharmaceutical technology field.The present invention discloses the preparation method of succinyl aurantiin.Succinyl aurantiin provided by the present invention has the characteristics that water solubility is high, antibacterial activity is strong, anti-osteoporosis activity is strong as a kind of new naringenin derivative, and new medicament selection is provided for antiseptic and osteosporosis resistant medicament.
Description
Technical field
The invention belongs to pharmaceutical technology field, is related to a kind of succinyl aurantiin and its is dredged preparing antibacterial or treating sclerotin
Purposes in terms of loose medicine.
Background technology
Flavone compound (flavonoids compounds) is Secondary metabolites, universally present in nature
In plant, exist in the form of by free state or with sugar being combined into glycosides, not only quantity species is various, and structure type is complicated more
Sample, diversified pharmacological activity is shown, have antibacterial anti-inflammatory, hypoglycemic, anti-oxidant, radioresistance, anticancer, enhancing skeletonization thin
The pharmacological action such as born of the same parents' function and enhancing immunocompetence.In recent years, the research of flavone compound enters a new level,
With the further investigation to its structure-activity relationship, it was found that the mechanism of action of Pharmacological is it in medicine, field of food
Using theoretical foundation is provided, the utilization of flavone compound are accelerated.
Naringenin belongs to flavanone kind composition, has the effects such as antibacterial, anti-inflammatory, enhancing function of osteoblast, clinical
Applied to treatment bacterium infection, osteoporosis diseases are prevented and treated.Naringenin drug effect is notable, however, it is water-soluble very low
(0.0631g/L), it significantly limit the performance of its pharmacological activity.Naringenin radical derivative is obtained by being separated from nature
Method the problems such as cost high, purification steps troublesome, and the naringenin radical derivative or water-soluble that separation obtains at present generally be present
Property is low, or drug effect is not notable enough.How highly-water-soluble is prepared, efficient naringenin base medicine is key point of the invention.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of succinyl aurantiin and its preparing antibacterial or treatment sclerotin
Application in terms of loose medicine.
To solve the technical problem of the present invention, the technical scheme is that：A kind of succinyl ononin, there is following formula
(1) structure shown in：
To solve the technical problem of the present invention, another technical solution of the invention is：A kind of antibacterial or treatment sclerotin are dredged
Loose disease medicament, it is characterised in that including active component it is the succinyl aurantiin shown in formula (1), and pharmaceutical acceptable
Pharmaceutic adjuvant.
Preferably, including active component is the succinyl aurantiin shown in formula (1), and pharmaceutically acceptable carrier system
Standby piece agent, capsule, injection, powder-injection, granule, fat emulsion, micro-capsule, dripping pill, ointment or skin-permeable and control-released plaster
The medicine of formulation.
To solve the technical problem of the present invention, another technical solution of the invention is：Described succinyl aurantiin exists
Prepare the application of antibacterials.
To solve the technical problem of the present invention, another technical solution of the invention is：Described succinyl aurantiin exists
Prepare the application of osteosporosis resistant medicament.
Formula (1) compound of the present invention, it is that (preserving number is bacillus amyloliquefaciens FJ18：CCTCC NO：M
2016272) succinyl aurantiin is prepared in nonaqueous phase and is obtained, reactive chemistry formula sees below formula：
Synthetic method is：Using naringenin and glycosyl donor as raw material, under bacillus amyloliquefaciens FJ18 catalytic action,
Glycosylation occurs for 7 phenolic hydroxyl groups of naringenin, forms eriodictyol-7- O -glucoside；Eriodictyol-7- O -glucoside is then
Under bacillus amyloliquefaciens FJ18 catalytic action, succinylation occurs for the position of glucosyl group 6 " hydroxyl, forms succinyl shaddock ped
Glycosides.It is specifically divided into following steps：
Step (1)：By described bacillus amyloliquefaciens FJ18, cellar culture, fermentation are carried out, filtering fermentation liquor obtains wet
Thalline；
Step (2)：Using naringenin and glycosyl donor as raw material, prepare to obtain original with phosphate buffer solution and Examples of non-aqueous solvents
Expect solution；
Step (3)：The solution of step (2) is added to by the wet thallus of step (1) or with the wet thallus after carrier immobilized
Middle carry out catalytic reaction.
Described phosphate buffer solution concentration is 100~150mmol/L, pH 8.0.
Material solution described in step (2), in its component, the concentration of naringenin is 0.01~5g/L, glycosyl donor
Solution concentration is 5~50g/L, and Examples of non-aqueous solvents percent by volume is 5%~20%.Described Examples of non-aqueous solvents be selected from methanol,
Any one in ethanol, acetonitrile, dimethylformamide, dimethyl sulfoxide (DMSO), acetone.Described Examples of non-aqueous solvents is that dimethyl is sub-
Sulfone or ethanol.Described glycosyl donor is sucrose or maltose.
Succinyl aurantiin of the present invention does not have been reported that before this as noval chemical compound.
Used in suppression of the present invention research succinyl aurantiin to Escherichia coli and staphylococcus aureus, verified with this
Application of the succinyl aurantiin in terms of antibacterials are prepared described in formula (1).Method is respectively with chloramphenicol (CHL), mould
Plain G (PG) is positive control, with Escherichia coli (E.coli) and staphylococcus aureus (S.aureus) for strain subject, is used
Micro-dilution method, determine the absorbance of thalline, research naringenin, the antibacterial activity of succinyl aurantiin.Tested Escherichia coli and
Staphylococcus aureus is to cultivate 18h thalline, the OD of thalline620nmIt is worth and is for 0.55-0.65, the concentration of test-compound
500umol-0.488umol, diluted using micro-dilution method.Thalline and compound mixing, determine the absorbance after 24h.As a result
It has been shown that, the half Mlc of succinyl aurantiin is 15.6umol, Escherichia coli and staphylococcus aureus is respectively provided with aobvious
The inhibition of work.
Application of the succinyl aurantiin of the present invention in terms of osteoporosis is treated.Method is male SPF levels SD rats 50
Only, normal group, model group, succinyl aurantiin height (50mg/kg), low dose group (25mg/kg) and strange group of calcium that are randomly divided into
(0.3g/kg).In addition to normal group, alternating intramuscular injection of dexamethasone (1mg/kg) modeling of the femoribus internus of rat two, 2 times a week.8
Zhou Hou, observation rat body weight change, takes rat femur, weighs the ash weight after its weight in wet base, dry weight and calcining, it is wet to calculate femur
Weight, dry weight, ash are heavy and the ratio results of volume are shown, compared with normal group, model group rats femur weight in wet base/volume, dry weight/
Volume, grey weight/volume significantly reduce (P ＜ 0.01)；Compared with model group, each administration group rat femur weight in wet base/volume, do
Weight/volume, grey weight/volume are significantly raised.
Application of the succinyl aurantiin of the present invention in terms of osteoporosis is treated.Method is using 1 monthly age SD rat 30
Only, it is divided into 5 groups：Blank group, model group, calcitriol group, succinyl aurantiin high dose group (1uM), succinyl aurantiin are low
Dosage group (0.5uM).Separating bone marrow mesenchymal stem, mtt assay detect succinyl aurantiin to dexamethasone inducing bone marrow
Mesenchymal stem cells effect of vigor.Compared with blank, dexamethasone can significantly reduce mesenchymal stem cells MSCs vigor, succinyl shaddock
Skin glycosides high dose, low dosage and calcitriol group can significantly raise the vigor of mesenchymal stem cells MSCs；Compared with blank, ground plug
Meter Song Neng significantly raises mesenchymal stem cells MSCs supernatant IL-6, IL-1 β, TNF-α, succinyl aurantiin high dose, low dosage
Mesenchymal stem cells MSCs supernatant IL-6, IL-1 β, TNF-α content can be significantly reduced with calcitriol group.Succinyl aurantiin has
There is good preventing and treating osteoporosis effect, laid a good foundation for the expansion application of naringenin derivative medically.
Beneficial effect：
1. it is the succinyl aurantiin described in formula (1) the invention provides a kind of noval chemical compound；
2. succinyl aurantiin provided by the present invention has high water-soluble as a kind of new naringenin derivative
Property (being 102 times of naringenin), and there is notable drug effect in terms of antibacterial and anti-osteoporosis, it is antiseptic and osteoporosis disease
Disease provides new drug effect.
Brief description of the drawings
Fig. 1 is succinyl aurantiin1H NMR spectras.
Fig. 2 is succinyl aurantiin13C NMR spectras.
Fig. 3 is the HMBC spectrograms of succinyl aurantiin.
Fig. 4 is inhibitory action of the succinyl aurantiin to Escherichia coli and staphylococcus aureus.
Bacillus amyloliquefaciens FJ18 provided by the invention submitted Chinese Typical Representative culture to protect on May 20th, 2016
(referred to as CCTCC, positioned at Wuhan, China university) carries out preservation at Tibetan center, and preserving number is CCTCC NO：M2016272.
Embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described with reference to embodiment, still
It should be appreciated that these descriptions are simply further explanation the features and advantages of the present invention, rather than to the claims in the present invention
Limitation.
Embodiment 1
Bacillus amyloliquefaciens FJ18 fermentation and the preparation of resting cell
Bacillus amyloliquefaciens FJ18 fermentation is inoculated into seed culture medium：Yeast extract 5.0g/L, peptone
10.0g/L, NaCl 10.0g/L, pH7.0, in 30 DEG C, 200rpm is cultivated 12 hours.Expand culture medium, fermentation medium, its group
Divide and content is：Sucrose 20g/L, dusty yeast 15g/L.KH2PO41.0g/L, CaCl20.8g/L.With NaOH adjust pH to
8.0.Seed liquor is inoculated into by 0.5% (v/v) expands culture medium, fermentation medium, and in 30 DEG C, 200rpm is cultivated 12 hours.
10000rpm collects somatic cells after centrifuging 15 minutes, with brine l~2 time, obtains bacillus amyloliquefaciens FJ18's
Resting cell.
Embodiment 2
By the somatic cells filtering fermentation liquor in embodiment 1, wet thallus is obtained.With dimethyl sulfoxide (DMSO), naringenin, sucrose,
Phosphoric acid buffer configures material solution, i.e. reaction solution.The ratio of organic solvent dimethyl sulfoxide (DMSO) is 20% (v/ in reaction solution
V), naringenin 0.5g/L, the molar concentration of phosphoric acid buffer is 150mmol/L, the pH 8.0 of phosphoric acid buffer, sucrose concentration 50g/
L.The wet thallus of above-mentioned gained is scattered in reaction solution, is added in reactor, in 30 DEG C, is cultivated under the conditions of 200rpm
After 24h, 10000rpm centrifuges 10 minutes to obtain reaction solution supernatant, and HPLC measures naringenin conversion ratio as 97.2%.
Product is separated with macroreticular resin, takes quantity of resin, after soaking 24h with ethanol, removes resin chips and debris.
Wet method dress postNo alcohol taste is washed to 1L alcohol flushings, then with distillation；The processing of row soda acid is connect, i.e., successively
With the NaOH solution of the HCl solution of volume fraction 5% and mass fraction 2% respectively with 2BV/h flow velocitys by resin column, and it is static
After putting 2~4h, pH value neutrality is washed to distillation.Loading adsorption rate is reduced to avoid DMSO from dissolving converted product, so conversion
Liquid is diluted to DMSO with the deionized water (pH4.0, glacial acetic acid regulation) of 5 times of volumes<It is loaded after 2%.The wet trees of sample-adding amount 20mg/g
Fat, sample-adding flow velocity 20mL/min.With deionized water (pH4.0, glacial acetic acid regulation) excessive unreacted of elution of 10 times of bed volumes
Glycosyl donor (sucrose), until the eluent concentrated sulfuric acid inspection do not measure sugar untill, flow velocity 20mL/min.From methanol plus go from
Sub- water is eluted as mobile phase, adjusts the volume ratio of methanol and deionized water, in elution flow rate 20mL/min, it is determined that elution
Methanol ratio in liquid.It is concentrated and dried：Detected through HPLC, merge eluent, its reduced vacuum concentrated with Rotary Evaporators, heating
40 DEG C of temperature.Finally solid is placed in vacuum drying chamber, 40 DEG C of dry 6h.
The reactive chemistry formula that succinyl aurantiin is prepared in bacillus amyloliquefaciens FJ18 nonaqueous phases sees below formula：
Analyzed and identified through mass spectrum of nuclear magnetic resonance from NMR spectra, the structure of acquisition is consistent with the structure of expected product.With
Upper result confirms to generate the naringenin of glucosyl, i.e. succinyl aurantiin in the reaction.The nuclear-magnetism of succinyl aurantiin
Resonance spectral data be：
Succinyl aurantiin1H NMR、13The ownership at C H NMR spectroscopies peak：1H-NMR(DMSO-d6,300MHz)δ：7.32(2H,
D, J=6.0Hz, 2'and 6'-H), 6.80 (2H, d, J=6.3Hz, 3'and 5'-H), 6.16 (2H, d, J=16.5Hz,
8and6-H), 5.49 (1H, d, J=8.7Hz, 2-H), the 5.00 (- H of 1H, m, 1 "), the 4.33 (- H of 1H, d, 8.7Hz, 6 "A),4.00-
4.03(1H,m,6”-HB),3.64-3.68(1H,m,5”-H),3.35-3.40(1H,m,3-HA),3.23-3.34(2H,m,2”
and 3”-H),3.12-3.16(1H,m,5”-HB),2.70-2.73(1H,m,3-HB),2.30-2.45(4H,m,2”'and
3”'-H).
13C-NMR(DMSO-d6,400MHz)δ：197.7(C-4),173.8(C-4”'),172.5(C-1”'),165.4(C-
7), 165.4 (C-9), 163.3 (C-5), 158.3 (C-4'), 129.1 (C-1'), 128.9 (C-2', 6'), 115.6 (C-3',
5'),103.8(C-10),99.7(C-1”),97.0(C-6),96.0(C-8),79.2(C-2),76.7(C-3”),74.3(C-
5”),73.4(C-2”),70.4(C-4”),64.0(C-6”),42.6(C-3),29.0(C-2”',C-3”').
Embodiment 3
By the somatic cells filtering fermentation liquor in embodiment 1, wet thallus is obtained.With dimethyl sulfoxide (DMSO), naringenin, sucrose,
Phosphoric acid buffer configures material solution, i.e. reaction solution.The ratio of organic solvent dimethyl sulfoxide (DMSO) is 15% (v/ in reaction solution
V), naringenin 1.0g/L, the molar concentration of phosphoric acid buffer is 125mmol/L, the pH 8.0 of phosphoric acid buffer, sucrose concentration 25g/
L.The wet thallus of above-mentioned gained is scattered in reaction solution, is added in reactor, in 30 DEG C, is cultivated under the conditions of 200rpm
After 24h, 10000rpm centrifuges 10 minutes to obtain reaction solution supernatant, and HPLC measures naringenin conversion ratio as 95.8%.
Product is separated with macroreticular resin, and method is the same as embodiment 2；Product detection method is the same as embodiment 2.
Embodiment 4
By the somatic cells filtering fermentation liquor in embodiment 1, wet thallus is obtained.With dimethyl sulfoxide (DMSO), naringenin, sucrose,
Phosphoric acid buffer configures material solution, i.e. reaction solution.The ratio of organic solvent dimethyl sulfoxide (DMSO) is 5% (v/v) in reaction solution,
Naringenin 0.1g/L, the molar concentration of phosphoric acid buffer is 100mmol/L, the pH 8.0 of phosphoric acid buffer, sucrose concentration 5g/L.Will
The wet thallus of above-mentioned gained is scattered in reaction solution, is added in reactor, in 30 DEG C, after cultivating 36h under the conditions of 200rpm,
10000rpm centrifuges 10 minutes to obtain reaction solution supernatant, and HPLC measures naringenin conversion ratio as 95.6%.Product is used
Macroreticular resin is separated, and method is the same as embodiment 2；Product detection method is the same as embodiment 2.
Embodiment 5
By the somatic cells filtering fermentation liquor in embodiment 1, wet thallus is obtained.Delayed with ethanol, naringenin, sucrose, phosphoric acid
Punching configuration material solution, i.e. reaction solution.The ratio of organic solvent ethanol is 15% (v/v), naringenin 1.0g/ in reaction solution
L, the molar concentration of phosphoric acid buffer is 125mmol/L, the pH 8.0 of phosphoric acid buffer, lactose concn 30g/L.By above-mentioned gained
Wet thallus is scattered in reaction solution, is added in reactor, in 30 DEG C, under the conditions of 200rpm cultivate 48h after, 10000rpm from
The heart obtains reaction solution supernatant for 10 minutes, and HPLC measures naringenin conversion ratio as 94.2%.Product is entered with macroreticular resin
Row separation, method is the same as embodiment 2；Product detection method is the same as embodiment 2.
Embodiment 6
The succinyl aurantiin solubility test of the present invention
Precision measures appropriate naringenin converted product stock solution and is placed in measuring bottle respectively, is diluted with water and is settled to quarter
Degree, the series standard solution that naringenin converted product concentration is 0.5,0.1,0.02,0.01,0.005 is respectively prepared.Standard is molten
Liquid carry out HPLC measure, with sample peak area (A) to drug concentration (C, mg/ml) carry out linear regression, with determine naringenin and
The solubility of succinyl aurantiin.
The solubility of succinyl aurantiin is 6.46mg/ml, and the solubility of naringenin is 63.12 μ g/ml, succinyl shaddock
The solubility of skin glycosides is about 102 times of naringenin solubility, drastically increases the solubility in water, expand naringenin and
The application and efficiency of its derivative industrially.
Embodiment 7
Application of the succinyl aurantiin of the present invention in antibiosis
Respectively with chloramphenicol (CHL), benzyl penicillin (PG) for positive control, with Escherichia coli (E.coli) and golden yellow Portugal
Grape coccus (S.aureus) is strain subject, using micro-dilution method, determines the absorbance of thalline, studies naringenin, succinyl
The antibacterial activity of aurantiin.Tested Escherichia coli and staphylococcus aureus are to cultivate 18h thalline, the OD of thalline620nmIt is worth and is
0.55-0.65, the concentration of test-compound is 500umol-0.488umol, is diluted using micro-dilution method.Thalline and compound
Mixing, determine the absorbance after 24h.
As a result show, the half Mlc of succinyl aurantiin is 15.6umol, to Escherichia coli and golden yellow grape
Coccus is respectively provided with significant inhibition.
Embodiment 8
Application of the succinyl aurantiin of the present invention in terms of osteoporosis is treated
Male SPF levels SD rats 50, are randomly divided into normal group, model group, succinyl aurantiin height (50mg/kg), low
Dosage group (25mg/kg) and the strange group (0.3g/kg) of calcium that.In addition to normal group, fill in the alternating intramuscular injection of the femoribus internus of rat two
Meter Song (1mg/kg) modeling, 2 times a week.After 8 weeks, observation rat body weight change, take rat femur, weigh its weight in wet base, dry weight with
And the ash after calcining is heavy, the ratio of femur weight in wet base, dry weight, ash weight and volume is calculated
As a result show, compared with normal group, model group rats femur weight in wet base/volume, dry weight/volume, grey weight/volume are aobvious
Writing reduces (P ＜ 0.01)；Compared with model group, each administration group rat femur weight in wet base/volume, dry weight/volume, grey weight/volume are equal
It is significantly raised.
Influence (n=10) of the succinyl aurantiin of table 1 to glucocorticoid-induced osteoporosis rat bone amount
Note：The * P ＜ 0.05 compared with normal group, compared with model group#P ＜ 0.01
As shown in Table 1, succinyl aurantiin has good preventing and treating osteoporosis effect, be naringenin derivative in medical science
On expansion application lay a good foundation.
Embodiment 9
Application of the succinyl aurantiin of the present invention in terms of osteoporosis is treated
Osteoporosis be it is a kind of by Low BMD and easily cause fracture characterized by general bone metabolism disease.Dexamethasone
A variety of influences can be produced on mesenchymal stem cells MSCs, excessive dexamethasone can cause mesenchymal stem cells MSCs to damage, and break
Bad Gegenbaur's cell and osteoclast dynamic equilibrium between the two are probably to cause one of major reason of osteoporosis.
Using 1 monthly age SD rat 30, it is divided into 5 groups：Blank group, model group, calcitriol group, the high agent of succinyl aurantiin
Amount group (1uM), succinyl aurantiin low dose group (0.5uM).Separating bone marrow mesenchymal stem, mtt assay detection succinyl shaddock
Skin glycosides is to dexamethasone inducing bone mesenchymal stem cell effect of vigor.Compared with blank, dexamethasone can significantly reduce marrow
Mescenchymal stem cell vigor, succinyl aurantiin high dose, low dosage and calcitriol group can significantly raise medulla mesenchyma and do
The vigor of cell, the results are shown in Table 2.
The succinyl aurantiin of table 2 is to dexamethasone inducing bone mesenchymal stem cell effect of vigor (n=6, x ± s)
Note：With blank ratio：##P<0.01；With model ratio：**P<0.01
Compared with blank, dexamethasone can significantly raise mesenchymal stem cells MSCs supernatant IL-6, IL-1 β, TNF-α, amber
Amber acyl aurantiin high dose, low dosage and calcitriol group can significantly reduce mesenchymal stem cells MSCs supernatant IL-6, IL-1 β,
TNF-α content, the results are shown in Table 3.
Influence (n=6, x ± s) of the succinyl aurantiin of table 3 to inflammatory factor in cell supernatant
Note：With blank ratio：##P<0.01；With model ratio：*P<0.05,**P<0.01
Embodiment 10
The preparation of tablet
Prescription (with the prescription gauge of 1000)：
Gained succinyl aurantiin sterling 60g in embodiment 3；
Sucrose 60g；
Cornstarch 80g；
Magnesium stearate 2g.
Preparation method：Active component is mixed with sucrose, cornstarch, adds water to moisten, stirs, dry, pulverize
Sieve, magnesium stearate is added, be well mixed, tabletting.Average piece weight 202mg/ pieces, active component content 60mg.
Embodiment 11
The preparation of parenteral solution
Prescription：(with the prescription gauge of 1000)
Middle gained succinyl aurantiin sterling 10g in embodiment 4；
Propane diols 100g；
Water for injection adds to 1000ml.
The succinyl aurantiin sterling sterling of recipe quantity is dissolved in propane diols, injects water to 1000ml, is mixed
Uniformly, filter, the solution obtained is aseptically sub-packed in ampoule bottle, 1ml/ bottle parenteral solutions, active component is made
Content is 10mg/mL.
Embodiment 12
The preparation of granule
Gained succinyl aurantiin sterling 80g in embodiment 5；
Mannitol 80g；
Sucrose 320g；
Cornstarch 80g；
Sodium carboxymethylcellulose 32g；
10% starch slurry is appropriate
Preparation method：By succinyl aurantiin sterling, mannitol, sucrose, cornstarch, sodium carboxymethylcellulose mistake respectively
100 mesh sieves, are weighed by recipe quantity, mixed plus softwood is made in 10% starch slurry, after being pelletized with 14 mesh sieves, put 70~80 DEG C of dryings
After 12 mesh sieve whole grains, packing.
Claims (5)
1. a kind of succinyl aurantiin, it is characterised in that described succinyl aurantiin has the structure shown in following formula (1)：
。
2. a kind of antibacterial or treatment bone loss disorders medicine, it is characterised in that including active component be formula (1) shown in amber
Acyl aurantiin, and the pharmaceutic adjuvant of pharmaceutical acceptable.
3. antibacterial according to claim 2 or treatment bone loss disorders medicine, it is characterised in that be including active component
Succinyl aurantiin shown in formula (1), and pharmaceutically acceptable carrier prepare piece agent, capsule, injection, powder pin
Agent, granule, fat emulsion, micro-capsule, dripping pill, the medicine of ointment or skin-permeable and control-released plaster formulation.
4. succinyl aurantiin according to claim 1 is preparing the application of antibacterials.
5. succinyl aurantiin according to claim 1 is preparing the application of osteosporosis resistant medicament.
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