CN109762859A - A kind of compound and the preparation method and application thereof with antibacterial activity - Google Patents
A kind of compound and the preparation method and application thereof with antibacterial activity Download PDFInfo
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- CN109762859A CN109762859A CN201910036899.5A CN201910036899A CN109762859A CN 109762859 A CN109762859 A CN 109762859A CN 201910036899 A CN201910036899 A CN 201910036899A CN 109762859 A CN109762859 A CN 109762859A
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- acetone
- methanol
- antibacterial activity
- ethyl acetate
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 40
- 150000001875 compounds Chemical class 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- -1 glucoside compound Chemical class 0.000 claims abstract description 30
- 238000000855 fermentation Methods 0.000 claims abstract description 24
- 230000004151 fermentation Effects 0.000 claims abstract description 24
- 241000193744 Bacillus amyloliquefaciens Species 0.000 claims abstract description 19
- 239000007788 liquid Substances 0.000 claims abstract description 19
- 239000000126 substance Substances 0.000 claims abstract description 8
- 244000052616 bacterial pathogen Species 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000002537 cosmetic Substances 0.000 claims abstract description 4
- 239000000575 pesticide Substances 0.000 claims abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 150
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 138
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 128
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 52
- 229930182470 glycoside Natural products 0.000 claims description 29
- 239000000284 extract Substances 0.000 claims description 18
- 230000003385 bacteriostatic effect Effects 0.000 claims description 15
- 238000000926 separation method Methods 0.000 claims description 14
- 238000010828 elution Methods 0.000 claims description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- 241000894006 Bacteria Species 0.000 claims description 11
- 239000002609 medium Substances 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000012046 mixed solvent Substances 0.000 claims description 9
- 239000000741 silica gel Substances 0.000 claims description 9
- 229910002027 silica gel Inorganic materials 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003208 petroleum Substances 0.000 claims description 8
- 239000006228 supernatant Substances 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 7
- 238000002390 rotary evaporation Methods 0.000 claims description 7
- 239000006137 Luria-Bertani broth Substances 0.000 claims description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- 229920001817 Agar Polymers 0.000 claims description 5
- 239000008272 agar Substances 0.000 claims description 5
- 238000009792 diffusion process Methods 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 239000002054 inoculum Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 238000010898 silica gel chromatography Methods 0.000 claims description 5
- 238000000825 ultraviolet detection Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
- 239000008103 glucose Substances 0.000 claims description 4
- 238000009629 microbiological culture Methods 0.000 claims description 4
- 239000007836 KH2PO4 Substances 0.000 claims description 3
- 239000001888 Peptone Substances 0.000 claims description 3
- 108010080698 Peptones Proteins 0.000 claims description 3
- 229920002472 Starch Polymers 0.000 claims description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 3
- 229940041514 candida albicans extract Drugs 0.000 claims description 3
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 3
- 229910000396 dipotassium phosphate Inorganic materials 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims description 3
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims description 3
- 235000019319 peptone Nutrition 0.000 claims description 3
- 239000001509 sodium citrate Substances 0.000 claims description 3
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 239000012138 yeast extract Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 229940112822 chewing gum Drugs 0.000 claims description 2
- 235000015218 chewing gum Nutrition 0.000 claims description 2
- 239000005452 food preservative Substances 0.000 claims description 2
- 235000019249 food preservative Nutrition 0.000 claims description 2
- 238000003808 methanol extraction Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000003595 spectral effect Effects 0.000 claims 1
- 229930182478 glucoside Natural products 0.000 abstract description 16
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000005764 inhibitory process Effects 0.000 abstract description 2
- 230000000813 microbial effect Effects 0.000 abstract description 2
- 239000000287 crude extract Substances 0.000 description 14
- 150000008131 glucosides Chemical class 0.000 description 10
- 239000003755 preservative agent Substances 0.000 description 8
- 230000002335 preservative effect Effects 0.000 description 8
- 239000003480 eluent Substances 0.000 description 7
- 241000234295 Musa Species 0.000 description 6
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 5
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- 241000191967 Staphylococcus aureus Species 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
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- 238000007445 Chromatographic isolation Methods 0.000 description 3
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- 238000001514 detection method Methods 0.000 description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 3
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- 150000002338 glycosides Chemical class 0.000 description 2
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- 238000011160 research Methods 0.000 description 2
- DBOVHQOUSDWAPQ-UHFFFAOYSA-N (4aS)-6c-[O2-(3,5,3'-trihydroxy-biphenyl-2-carbonyl)-beta-D-glucopyranosyloxy]-5t-vinyl-(4ar)-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one Natural products OC1C(O)C(CO)OC(OC2C(C3C(C(OCC3)=O)=CO2)C=C)C1OC(=O)C1=C(O)C=C(O)C=C1C1=CC=CC(O)=C1 DBOVHQOUSDWAPQ-UHFFFAOYSA-N 0.000 description 1
- XUCIJNAGGSZNQT-JHSLDZJXSA-N (R)-amygdalin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O[C@@H](C#N)C=2C=CC=CC=2)O1 XUCIJNAGGSZNQT-JHSLDZJXSA-N 0.000 description 1
- ATRSAWXXYCBXLI-UHFFFAOYSA-N 1-(3-bromophenyl)propan-2-amine Chemical compound CC(N)CC1=CC=CC(Br)=C1 ATRSAWXXYCBXLI-UHFFFAOYSA-N 0.000 description 1
- BZXINCMCFVKGKB-UHFFFAOYSA-N Amarogentin Natural products OCC1OC(OC2OC=C3C(CCOC3=O)C2C=C)C(OC(=O)c4cc(O)cc(O)c4c5cccc(O)c5)C(O)C1O BZXINCMCFVKGKB-UHFFFAOYSA-N 0.000 description 1
- 241000208671 Campanulaceae Species 0.000 description 1
- LKDRXBCSQODPBY-VRPWFDPXSA-N D-fructopyranose Chemical compound OCC1(O)OC[C@@H](O)[C@@H](O)[C@@H]1O LKDRXBCSQODPBY-VRPWFDPXSA-N 0.000 description 1
- 208000005156 Dehydration Diseases 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 244000292697 Polygonum aviculare Species 0.000 description 1
- 235000006386 Polygonum aviculare Nutrition 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- DBOVHQOUSDWAPQ-WTONXPSSSA-N amarogentin Chemical compound O([C@H]1[C@H](O[C@H]2[C@@H]([C@H]3C(C(OCC3)=O)=CO2)C=C)O[C@@H]([C@H]([C@@H]1O)O)CO)C(=O)C1=C(O)C=C(O)C=C1C1=CC=CC(O)=C1 DBOVHQOUSDWAPQ-WTONXPSSSA-N 0.000 description 1
- 229940089837 amygdalin Drugs 0.000 description 1
- YZLOSXFCSIDECK-UHFFFAOYSA-N amygdalin Natural products OCC1OC(OCC2OC(O)C(O)C(O)C2O)C(O)C(O)C1OC(C#N)c3ccccc3 YZLOSXFCSIDECK-UHFFFAOYSA-N 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
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- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- VEGXETMJINRLTH-ALRICIOSSA-N etimicin Chemical group O1C[C@@](O)(C)[C@H](NC)[C@H](O)[C@H]1O[C@@H]1[C@H](O)[C@H](O[C@@H]2[C@@H](CC[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N VEGXETMJINRLTH-ALRICIOSSA-N 0.000 description 1
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- YGHHWSRCTPQFFC-UHFFFAOYSA-N eucalyptosin A Natural products OC1C(O)C(O)C(CO)OC1OC1C(OC(C#N)C=2C=CC=CC=2)OC(CO)C(O)C1O YGHHWSRCTPQFFC-UHFFFAOYSA-N 0.000 description 1
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- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
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Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
The present invention relates to a kind of compound and the preparation method and application thereof with antibacterial activity, the chemical structural formula of the compound with antibacterial activity are shown in formula I:
Description
Technical field
The present invention relates to a kind of compound and the preparation method and application thereof with antibacterial activity, belongs to biological antibiotic element skill
Art field.
Background technique
Nowadays under the commonly used environment of antibiotic, society and scientific circles occur seeming rapidly to the drug resistance of bacterium to be arranged
Hand is too late, therefore the exploitation quick and lasting there is an urgent need to the antibiotic of new type, is sexually revised with adapting to bacteria antibiotic sensitivity
Speed.Natural antimicrobial substance is mainly derived from plant, animal, microorganism and mineral.In the past ten years, pass through microorganism
It screens to find the developmental research of antibiotic and other reactive compounds with medical and health care value and be unfolded rapidly, perhaps
Antibacterial, antiviral compound mostly with recruit's structure have been isolated and identified, and active constituent is diversified, including
Terpenes, fatty acid, macrolide, quinones, peptides, alkaloid, ethers and heterocyclic compound etc., the knot of some of them ingredient
Structure, property have been elucidated with.Also there are many microorganism extract for not yet identifying its bioactive molecule structure is contained, for preventing various diseases
Evil.
Glucosides, also referred to as glycocide.The hemiacetal hydroxyl and hydroxyl, amino or thiol in another molecule for being monosaccharide or oligosaccharides
The dehydrations such as base and generate hydrate.Therefore a glucosides can be divided into two parts.A part is that (sugar removes hemiacetal hydroxyl to sugared residue
Base), another part is aglucon (non-saccharide part), and key is known as glycosidic bond.Aglucon part can be very simply, be also possible to
Very complicated.Glycosidic bond can be joined to one another by oxygen, sulphur, nitrogen-atoms, their glucosides is briefly referred to as O- glycosides, S-
Glycosides, N- glycosides or C- glycosides.The aglucon of glucosides can be sugar, thus be condensed into disaccharide, oligosaccharides and polysaccharide.
Glucosides is distributed widely in root, stem, leaf, flower and the fruit of plant.It is colored crystal mostly, water can be dissolved in.Generally
Bitter.Some have severe toxicity.Sugar and other substances are generated when hydrolysis.Such as amarogentin (amygdalin) C20H27NO11Hydrolysis
Final product is glucose C6H12O6, benzaldehyde C6H5CHO and hydrogen cyanide HCN.Glucosides can be used as drug.Much Chinese medicines is effective
Ingredient is exactly glucosides, such as radix bupleuri, campanulaceae, Radix Polygalae etc..Due to the difference of spatial configuration, glucosides has α and β two types.Grape
The glycosides of the glycosides (heteroside) of sugar and other sugar, most of is β-type glucosides.
The glucoside compound with antibacterial action focuses primarily upon glucoside-containing component at present.Such as Chinese patent text
Offer CN108003205A (application number 201711401335.4) disclose a kind of aminoglycoside derivatives and preparation method thereof and
Using being a kind of new aminoglycoside derivatives.The derivative be mainly to C2 ' the amino position of Etimicin and
C6 ' amino position has carried out the modification of chemical structure, has obtained two analog derivatives: the derivative and C2 '-of C6 '-NH2 modification
The derivative of the double target position modifications of NH2 and C6 '-NH2；And molecular design and antibacterial activity in vitro research are carried out.The result shows that
Said derivative is equal to bacteriums such as such as methicillin-resistant staphylococcus aureus and the bacterial strains for expressing N6 ' aminoglycoside modification enzyme
Has the characteristics that preferable anti-drug resistance bacterium.
Current existing glucoside compound be mainly derived from folium cortex eucommiae (folium cortex eucommiae chemical constitution study, the left moon are bright etc., in
Medicinal material V37 2014.10:1786-1788), extract in the Chinese medicines such as nerville knotweed, by raw material sources, the place of production, content, raw material it is steady
Qualitative limitation has the related report in terms of antibacterial activity there is no glucoside compound.
Summary of the invention
In view of the deficiencies of the prior art, the present invention provides a kind of compound with antibacterial activity and preparation method thereof with answer
With.
A kind of compound with antibacterial activity, chemical structural formula are shown in formula I:
The preparation method of the above-mentioned compound with antibacterial activity, includes the following steps:
(1) fermentation liquid of bacillus amyloliquefaciens is centrifuged, takes supernatant, through methanol extraction, extract is made；
The bacillus amyloliquefaciens derive from China General Microbiological culture presevation administrative center, bacterium numbering
CGMCC1.936；
(2) by extract made from step (1) through silica gel post separation, with gradient organic solvent petrol ether/ethyl acetate/the third
Ketone/methanol is successively eluted according to the mixed solvent of different proportion；It is dense that acetone/methanol is finally mixed into elution solution progress
The glycoside compounds with antibacterial activity are made through high performance liquid chromatography separation in contracting.
Preferred according to the present invention, in the step (1), the preparation step of bacillus amyloliquefaciens fermentation liquid is as follows:
(i) bacillus amyloliquefaciens are accessed in LB broth bouillon, is trained under the conditions of 35~37 DEG C, 180~200rpm
It supports 14~16h hours, seed liquor is made；
The LB liquid medium, component are as follows:
10 grams of peptone, 10 grams of sodium chloride, 5 grams of yeast extract, water is settled to 1L；
(ii) seed liquor made from step (i) being inoculated in fermentation medium, inoculum concentration presses percent by volume 3~5%,
It is cultivated 44~52 hours under the conditions of 28~32 DEG C, 180~200rpm, fermentation liquid is made；
The fermentation medium, component are as follows:
Glucose 30.0g, K2HPO4×3H2O 7.0g, KH2PO43.0g, (NH4)2SO41.5g, sodium citrate × 3H2O
0.5g, MgSO4×7H2O 0.1g, sodium chloride 0.5g, soluble starch 0.1g；PH7.0~7.2 add water to be settled to 1L.
Preferred according to the present invention, in the step (1), bacillus amyloliquefaciens derive from China General Microbiological strain
Preservation administrative center, bacterium numbering CGMCC 1.936.The bacterial strain is common commercially available bacterial strain.
It is preferred according to the present invention, in the step (1), further include the steps that concentration after taking supernatant；It is further preferred that
The concentration is concentrated using rotary evaporation, is concentrated into the 8~12% of original volume.
Preferred according to the present invention, in the step (1), the volume ratio of methanol and the liquid for needing to extract is 1:1；Into one
Step is preferred, and the extraction times are three times.
Preferred according to the present invention, in the step (2), extract is comprised the concrete steps that through silica gel post separation: by extract
After drying, gained dried object is separated through 200 mesh silica gel column chromatographies, and sample and silica gel quality ratio are 1:100, respectively with 13 individuals
Product concentration gradient is eluted, and 13 bulk concentration gradient mixed solvents are eluted respectively, 13 bulk concentration gradients
Mixed solvent is respectively petroleum ether, petrol ether/ethyl acetate=80:20, petrol ether/ethyl acetate=50:50, petroleum ether/second
Acetoacetic ester=20:80, ethyl acetate, ethyl acetate/acetone=80:20, ethyl acetate/acetone=50:50, ethyl acetate/the third
Ketone=20:80, acetone, acetone/methanol 80:20, acetone/methanol 50:50, acetone/methanol 20:80, methanol；Collect acetone/first
Alcohol mixing elution solution.
Preferred according to the present invention, in the step (2), high performance liquid chromatography separation condition is as follows:
Chromatographic column is YMC-Pack ODS-A, specification 250*10.0mml.O.D.S-5um, 12nm；In percent by volume
70% methanol as mobile phase, 25 DEG C of column temperature, under conditions of the UV detection of flow velocity 1.5ml/min, 254nm, Isocratic clution；It receives
Collect compound chromatographic peak, the period where determining bacteriostatic activity with agar diffusion method, be concentrated through rotary evaporation, nitrogen drying is dry, obtains
The glycoside compounds that must be purified.
The above-mentioned glycoside compounds with antibacterial activity inhibit the application in pathogenic bacteria drug in preparation.
The above-mentioned glycoside compounds with antibacterial activity are preparing the application in food preservative.
The above-mentioned glycoside compounds with antibacterial activity are preparing the application in cosmetics.
The above-mentioned glycoside compounds with antibacterial activity are in the application for preparing health care product.
The above-mentioned glycoside compounds with antibacterial activity are preparing the application in pesticide.
The above-mentioned glycoside compounds with antibacterial activity are preparing the application in antibacterial chewing gum.
Beneficial effect
The present invention extracts in the fermentation liquid by bacillus amyloliquefaciens CGMCC1.936 for the first time a kind of has antibacterial activity
Glucoside compound, which has the function of very strong inhibition pathogenic bacteria, and using microbial fermentation preparation production week
Phase is short, product is stable, content is high, which can be widely applied in pesticide, medicine, health care product and Cosmetic Manufacture.
Detailed description of the invention
Fig. 1 is the curve graph that compound of formula I prepared by embodiment 1 inhibits staphylococcus aureus；
Fig. 2 is the curve graph that compound of formula I prepared by embodiment 1 inhibits S. pullonum；
Fig. 3 is the curve graph that compound of formula I prepared by embodiment 1 inhibits Bacterium enteritidis；
Fig. 4 is the curve graph that compound of formula I prepared by embodiment 1 inhibits pasteurella multocida；
Fig. 5 is the mass spectrogram of compound of formula I prepared by embodiment 1；
Fig. 6 is the partial enlarged view of the mass spectrogram of compound of formula I prepared by embodiment 1；
Fig. 7 is the compound of formula I of the preparation of embodiment 1 in the antibacterial experiment 2 of experimental example, weight-loss ratio-storage time pass
It is curve graph；
In figure, curve is respectively as follows: control group, low dose group, middle dose group, high dose group, preservative film from top to bottom at 5 days
Group, preservative film+middle dose group；
Fig. 8 is the compound of formula I of the preparation of embodiment 1 in the antibacterial experiment 2 of experimental example, soluble solids-storage time
Graph of relation；
In figure, curve is respectively as follows: preservative film+middle dose group, preservative film group, high dose group, middle dosage from top to bottom at 4 days
Group, control group, low dose group；
Fig. 9 is the bacteriostatic activity test result photo of extract prepared by embodiment 1；
Figure 10 be ingredient after embodiment 1 is eluted by 13 concentration gradients, after elution fractions are concentrated into
Row bacteriostatic activity test result photo；
In figure: 1-7 is respectively petroleum ether, petrol ether/ethyl acetate=80:20, petrol ether/ethyl acetate=50:50, stone
Oily ether/ethyl acetate=20:80, ethyl acetate, ethyl acetate/acetone=80:20, ethyl acetate/acetone=50:50,7 kinds are washed
Antibacterial result after de- liquid concentration；
Figure 11 be ingredient after embodiment 1 is eluted by 13 concentration gradients, after elution fractions are concentrated into
Row bacteriostatic activity test result photo；
In figure: 8-13 is respectively ethyl acetate/acetone=20:80, acetone, acetone/methanol 80:20, acetone/methanol 50:
50, acetone/methanol 20:80, methanol, the antibacterial result after 6 kinds of eluent concentrations.
Specific embodiment
Below with reference to embodiment, technical scheme is described further, but institute's protection scope of the present invention is not limited to
This.
Biological material source:
Bacillus amyloliquefaciens described in embodiment are purchased from China General Microbiological culture presevation administrative center, bacterium numbering
CGMCC1.936；
Culture medium:
LB broth bouillon, component are as follows:
10 grams of peptone, 10 grams of sodium chloride, 5 grams of yeast extract, water is settled to 1L；
Fermentation medium, component are as follows:
Glucose 30.0g, K2HPO4×3H2O 7.0g, KH2PO43.0g, (NH4)2SO41.5g, sodium citrate × 3H2O
0.5g, MgSO4×7H2O 0.1g, sodium chloride 0.5g, soluble starch 0.1g, pH7.0~7.2 add water to be settled to 1L.
Embodiment 1
A kind of preparation method of the compound with antibacterial activity, includes the following steps:
(1) bacillus amyloliquefaciens are accessed in LB broth bouillon, are cultivated 16 hours under the conditions of 37 DEG C, 180rpm,
Seed liquor is made；
Seed liquor obtained is inoculated in fermentation medium, inoculum concentration 5% (percent by volume), in 30 DEG C, 200rpm
Under the conditions of cultivate 48 hours, be made fermentation liquid；
The fermentation liquid of bacillus amyloliquefaciens is centrifuged, takes supernatant, rotary evaporation is concentrated into the 10% of original volume, then passes through
Methanol by volume 1:1 ratio extraction, be made extract；Bacteriostatic activity is detected, as a result as shown in Figure 9；
(2) by get reactive compound crude extract, gained crude extract is through 200 mesh after the drying of extract made from step (1)
Silica gel column chromatography separation, sample and silica gel quality ratio are 1:100, carry out elution 13 with 13 bulk concentration gradients respectively
Bulk concentration gradient mixed solvent is respectively petroleum ether, petrol ether/ethyl acetate=80:20, petrol ether/ethyl acetate=50:
50, petrol ether/ethyl acetate=20:80, ethyl acetate, ethyl acetate/acetone=80:20, ethyl acetate/acetone=50:50,
Ethyl acetate/acetone=20:80, acetone, acetone/methanol 80:20, acetone/methanol 50:50, acetone/methanol 20:80, methanol；
Each section eluent is collected, concentration carries out bacteriostatic activity detection, as a result as shown in Figure 10 and Figure 11 respectively.
It will be concentrated respectively by the eluent after acetone/methanol 80:20, acetone/methanol 50:50 elution, it is dry, through efficient liquid
Phase chromatographic isolation, high performance liquid chromatography separation condition are as follows:
Chromatographic column is YMC-Pack ODS-A, specification 250*10.0mml.O.D.S-5um, 12nm；In percent by volume
70% methanol as mobile phase, 25 DEG C of column temperature, under conditions of the UV detection of flow velocity 1.5ml/min, 254nm, Isocratic clution；It receives
Collect compound chromatographic peak, the glycoside compounds of purifying are made in the period where determining bacteriostatic activity with agar diffusion method.
The glycoside compounds of purifying are through Mass Spectrometer Method, and as a result as shown in Figure 5 and Figure 6, structural formula is shown in formula I:
The ingredient obtained respectively after the above-mentioned elution by acetone/methanol 80:20, acetone/methanol 50:50 is pure through liquid phase separation
Change, Structural Identification, it was demonstrated that be same structure glucoside compound.
Experimental example
Bacteriostatic experiment 1
(i) it using the crude extract in embodiment 1, is diluted with sterile water, makes the content of crude extract in 35.85-
358.5mg/mL range；
(ii) by the staphylococcus aureus of preparatory culture 14-16h, S. pullonum, Bacterium enteritidis, kill more
Property Pasteurella, add 100 μ L in each EP pipe, be centrifuged, abandoning supernatant retains above-mentioned pathogenic bacteria, and fresh 950 μ L is added
LB culture medium mixes；
(iii) reference numeral, the 50 μ L of sample being separately added into (i), and control group is set；
(iv) after being ready to complete, it is put into shaking table culture 14-16h；
(v) after the completion of cultivating, OD is detected with microplate reader600；
Through detecting, glycoside compounds made from embodiment 1 are husky to staphylococcus aureus, S. pullonum, enteritis
Door Salmonella, pasteurella multocida all have significant inhibitory effect, as a result as shown in Figs 1-4.
Antibacterial experiment 2
Crude extract prepared by embodiment 1 is configured to high, medium and low three concentration respectively and is used for banana fresh-keeping, experiment point six
A group, be control group, high dose group, middle dose group, low dose group, preservative film group and preservative film+middle dose group respectively, and every group adds
The solution that the crude extract that 200 μ L are prepared by embodiment 1 is prepared, wherein the crude extract concentration of low concentration is 250.95mg/mL, in it is dense
The crude extract concentration of degree is 322.65mg/mL, and the crude extract concentration of high concentration is 573.60mg/mL, and control group uses 200 μ L
The solution Direct Uniform for having configured gradient is applied on banana skin by water；The preservative film consolidation of PP material wraps entire perfume (or spice)
Any of several broadleaf plants is placed in 25 DEG C of constant incubators.Daily observation, detects related data, records and take pictures.
According to the variation of weight-loss ratio and soluble solid under daily detected different disposal, conclusion is as follows:
As storage period extends, the banana hardness (weight-loss ratio is low) and solubility of preservative film+middle dose group (M-BA+PP) are solid
Shape object content is higher, is more advantageous to the storage of banana.
In addition, in three experimental groups of crude extract processing, the banana hardness (weight-loss ratio is low) of high concentration group and solvable
Property solid content it is higher, the sensory evaluation of Binding experiment group sample, high concentration group processing it is best to banana fresh-keeping effect.
Embodiment 2
A kind of preparation method of the compound with antibacterial activity, includes the following steps:
(1) bacillus amyloliquefaciens are accessed in LB broth bouillon, are cultivated 14 hours under the conditions of 35 DEG C, 200rpm,
Seed liquor is made；
Seed liquor obtained is inoculated in fermentation medium, inoculum concentration 3% (percent by volume), in 32 DEG C, 180rpm
Under the conditions of cultivate 52 hours, be made fermentation liquid；
The fermentation liquid of bacillus amyloliquefaciens is centrifuged, takes supernatant, rotary evaporation is concentrated into the 8% of original volume, then passes through
Methanol by volume 1:1 ratio extraction, be made extract；Bacteriostatic activity is detected, as a result as shown in Figure 9；
(2) by get reactive compound crude extract, gained crude extract is through 200 mesh after the drying of extract made from step (1)
Silica gel column chromatography separation, sample and silica gel quality ratio are 1:100, carry out elution 13 with 13 bulk concentration gradients respectively
Bulk concentration gradient mixed solvent is respectively petroleum ether, petrol ether/ethyl acetate=80:20, petrol ether/ethyl acetate=50:
50, petrol ether/ethyl acetate=20:80, ethyl acetate, ethyl acetate/acetone=80:20, ethyl acetate/acetone=50:50,
Ethyl acetate/acetone=20:80, acetone, acetone/methanol 80:20, acetone/methanol 50:50, acetone/methanol 20:80, methanol；
Each section eluent is collected, concentration carries out bacteriostatic activity detection, as a result as shown in Figure 10 and Figure 11 respectively.
It will be concentrated respectively by the eluent after acetone/methanol 80:20, acetone/methanol 50:50 elution, it is dry, through efficient liquid
Phase chromatographic isolation, high performance liquid chromatography separation condition are as follows:
Chromatographic column is YMC-Pack ODS-A, specification 250*10.0mml.O.D.S-5um, 12nm；In percent by volume
70% methanol as mobile phase, 25 DEG C of column temperature, under conditions of the UV detection of flow velocity 1.5ml/min, 254nm, Isocratic clution；It receives
Collect compound chromatographic peak, the glycoside compounds of purifying are made in the period where determining bacteriostatic activity with agar diffusion method.
The glycoside compounds of purifying are through detecting, with embodiment 1.
Embodiment 3
A kind of preparation method of the compound with antibacterial activity, includes the following steps:
(1) bacillus amyloliquefaciens are accessed in LB broth bouillon, are cultivated 16 hours under the conditions of 36 DEG C, 200rpm,
Seed liquor is made；
Seed liquor obtained is inoculated in fermentation medium, inoculum concentration 4% (percent by volume), in 30 DEG C, 200rpm
Under the conditions of cultivate 44 hours, be made fermentation liquid；
The fermentation liquid of bacillus amyloliquefaciens is centrifuged, takes supernatant, rotary evaporation is concentrated into the 12% of original volume, then passes through
Methanol by volume 1:1 ratio extraction, be made extract；Bacteriostatic activity is detected, as a result as shown in Figure 9；
(2) by get reactive compound crude extract, gained crude extract is through 200 mesh after the drying of extract made from step (1)
Silica gel column chromatography separation, sample and silica gel quality ratio are 1:100, carry out elution 13 with 13 bulk concentration gradients respectively
Bulk concentration gradient mixed solvent is respectively petroleum ether, petrol ether/ethyl acetate=80:20, petrol ether/ethyl acetate=50:
50, petrol ether/ethyl acetate=20:80, ethyl acetate, ethyl acetate/acetone=80:20, ethyl acetate/acetone=50:50,
Ethyl acetate/acetone=20:80, acetone, acetone/methanol 80:20, acetone/methanol 50:50, acetone/methanol 20:80, methanol；
Each section eluent is collected, concentration carries out bacteriostatic activity detection, as a result as shown in Figure 10 and Figure 11 respectively.
It will be concentrated respectively by the eluent after acetone/methanol 80:20, acetone/methanol 50:50 elution, it is dry, through efficient liquid
Phase chromatographic isolation, high performance liquid chromatography separation condition are as follows:
Chromatographic column is YMC-Pack ODS-A, specification 250*10.0mml.O.D.S-5um, 12nm；In percent by volume
70% methanol as mobile phase, 25 DEG C of column temperature, under conditions of the UV detection of flow velocity 1.5ml/min, 254nm, Isocratic clution；It receives
Collect compound chromatographic peak, the glycoside compounds of purifying are made in the period where determining bacteriostatic activity with agar diffusion method.
The glycoside compounds of purifying are through detecting, with embodiment 1.
Claims (10)
1. a kind of compound with antibacterial activity, chemical structural formula are shown in formula I:
2. the preparation method of the compound described in claim 1 with antibacterial activity, which comprises the steps of:
(1) fermentation liquid of bacillus amyloliquefaciens is centrifuged, takes supernatant, through methanol extraction, extract is made；
The bacillus amyloliquefaciens derive from China General Microbiological culture presevation administrative center, bacterium numbering
CGMCC1.936；
(2) by extract made from step (1) through silica gel post separation, with gradient organic solvent petrol ether/ethyl acetate/acetone/
Methanol is successively eluted according to the mixed solvent of different proportion；Acetone/methanol is finally mixed elution solution to be concentrated,
Through high performance liquid chromatography separation, the glycoside compounds with antibacterial activity are made.
3. preparation method as claimed in claim 2, which is characterized in that in the step (1), bacillus amyloliquefaciens fermentation liquid
Preparation step it is as follows:
(i) bacillus amyloliquefaciens are accessed in LB broth bouillon, cultivates 14 under the conditions of 35~37 DEG C, 180~200rpm
~16 hours, seed liquor is made；
The LB liquid medium, component are as follows:
10 grams of peptone, 10 grams of sodium chloride, 5 grams of yeast extract, water is settled to 1L；
(ii) seed liquor made from step (i) is inoculated in fermentation medium, inoculum concentration presses percent by volume 3~5%, 28
~32 DEG C, cultivate 44~52 hours under the conditions of 180~200rpm, fermentation liquid is made；
The fermentation medium, component are as follows:
Glucose 30.0g, K2HPO4×3H2O 7.0g, KH2PO43.0g, (NH4)2SO41.5g, sodium citrate × 3H2O
0.5g, MgSO4×7H2O 0.1g, sodium chloride 0.5g, soluble starch 0.1g；PH7.0~7.2 add water to be settled to 1L.
Preferably, in the step (1), bacillus amyloliquefaciens derive from China General Microbiological culture presevation administrative center,
Bacterium numbering CGMCC 1.936；
Preferably, in the step (1), further include the steps that concentration after taking supernatant；It is further preferred that the concentration uses
Rotary evaporation concentration, is concentrated into the 8~12% of original volume；
Preferably, in the step (1), the volume ratio of methanol and the liquid for needing to extract is 1:1；It is further preferred that described
Extraction times are three times.
4. preparation method as claimed in claim 2, which is characterized in that in the step (2), extract through silica gel post separation,
Comprise the concrete steps that: after extract drying, gained dried object is separated through 200 mesh silica gel column chromatographies, and sample is with silica gel quality ratio
1:100 is eluted with 13 bulk concentration gradients respectively, and 13 bulk concentration gradient mixed solvents are washed respectively
De-, 13 bulk concentration gradient mixed solvents are respectively petroleum ether, petrol ether/ethyl acetate=80:20, petroleum ether/acetic acid
Ethyl ester=50:50, petrol ether/ethyl acetate=20:80, ethyl acetate, ethyl acetate/acetone=80:20, ethyl acetate/the third
Ketone=50:50, ethyl acetate/acetone=20:80, acetone, acetone/methanol 80:20, acetone/methanol 50:50, acetone/methanol
20:80, methanol；Collect acetone/methanol mixing elution solution；
Preferably, in the step (2), high performance liquid chromatography separation condition is as follows:
Chromatographic column is YMC-Pack ODS-A, specification 250*10.0mml.O.D.S-5um, 12nm；In 70% first of percent by volume
Alcohol mobile phase, 25 DEG C of column temperature, under conditions of the UV detection of flow velocity 1.5ml/min, 254nm, Isocratic clution；Collect chemical combination
Spectral peak is looked for, the period where determining bacteriostatic activity with agar diffusion method, is concentrated through rotary evaporation, nitrogen drying is dry, is purified
Glycoside compounds.
5. the glycoside compounds described in claim 1 with antibacterial activity inhibit the application in pathogenic bacteria drug in preparation.
6. the glycoside compounds described in claim 1 with antibacterial activity are preparing the application in food preservative.
7. the glycoside compounds described in claim 1 with antibacterial activity are preparing the application in cosmetics.
8. the glycoside compounds described in claim 1 with antibacterial activity are in the application for preparing health care product.
9. the glycoside compounds described in claim 1 with antibacterial activity are preparing the application in pesticide.
10. the glycoside compounds described in claim 1 with antibacterial activity are preparing the application in antibacterial chewing gum.
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| CN114951680A (en) * | 2022-05-17 | 2022-08-30 | 徐州工程学院 | Synthesis method and application of double-ligand gold nanoparticles with biological silencing region Raman signals |
| CN115820482A (en) * | 2022-11-11 | 2023-03-21 | 云南农业大学 | Bacillus amyloliquefaciens YN-BA2 and microbial inoculum and application thereof |
| CN115820482B (en) * | 2022-11-11 | 2024-08-02 | 云南农业大学 | Bacillus amyloliquefaciens YN-BA2 and microbial inoculum and application thereof |
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| US4310627A (en) * | 1979-09-17 | 1982-01-12 | The Upjohn Company | Process of producing 3-trehalosamine by fermentation |
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| US4310627A (en) * | 1979-09-17 | 1982-01-12 | The Upjohn Company | Process of producing 3-trehalosamine by fermentation |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114951680A (en) * | 2022-05-17 | 2022-08-30 | 徐州工程学院 | Synthesis method and application of double-ligand gold nanoparticles with biological silencing region Raman signals |
| CN115820482A (en) * | 2022-11-11 | 2023-03-21 | 云南农业大学 | Bacillus amyloliquefaciens YN-BA2 and microbial inoculum and application thereof |
| CN115820482B (en) * | 2022-11-11 | 2024-08-02 | 云南农业大学 | Bacillus amyloliquefaciens YN-BA2 and microbial inoculum and application thereof |
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