CN107266460B - Marine aspergillus SCSIO 05879 prepares Versicoloids A and B and the application in anti-colletotrichum gloeosporioides Penz drug - Google Patents
Marine aspergillus SCSIO 05879 prepares Versicoloids A and B and the application in anti-colletotrichum gloeosporioides Penz drug Download PDFInfo
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Abstract
The invention discloses marine aspergillus SCSIO 05879 to prepare Versicoloids A and B and the application in anti-colletotrichum gloeosporioides Penz drug.Versicoloids A and B, shown in structural formula such as formula (I), it is to be fermented to generate by aspergillus (Aspergillus sp.) SCSIO 05879, there is growth inhibitory activity to glue spore anthrax bacteria, rice blast fungus and banana blight bacteria, bioengineering transformation is carried out to it or modifying for chemical structure is expected to be developed into anti-phytopathogen new drug.
Description
This divisional application is application number：201610046509.9 denomination of invention：Antibiotic Versicoloids A and B and
Preparation method and preparing the application in anti-phytopathogen drug, the applying date：Patent application on 01 22nd, 2016
Divisional application.
Technical field：
The invention belongs to marine natural products fields, and in particular to prepared by marine aspergillus SCSIO 05879
Versicoloids A and B and the application in anti-colletotrichum gloeosporioides Penz drug.
Background technique：
Currently, phytopathogen present on agricultural production mainly has glue spore anthrax bacteria, rice blast fungus, banana withered
Wither germ, cucumber phytophthora wilt, Exserohilum turcicum, southern corn leaf blight, sugarcane pineapple germ etc., widely distributed,
It is very harmful to the production of crops.With the continuous improvement of people's living standards, to the quality requirements of edible agricultural and sideline product
It is higher and higher.Therefore, the active lead compound of prevention and treatment phytopathogen is screened and found from natural products, it is strong to the mankind
The sustainable development of health, agricultural and environment is all extremely important.
Summary of the invention：
There is the active alkaloid compound of anti-phytopathogen the first purpose of the invention is to provide a new class of
Versicoloids A and B.
A new class of alkaloid compound Versicoloids A or B of the invention, shown in structure such as formula (I)：
A second object of the present invention is to provide the preparation methods of alkaloid compound Versicoloids A and B.
Versicoloids A and B of the invention is trained from the fermentation of aspergillus (Aspergillus sp.) SCSIO 05879
Support what preparative separation in object obtained.
The present invention is preferably by the following method from the fermentation culture medium of aspergillus (Aspergillus sp.) SCSIO 05879
In Versicoloids A and B is prepared, specific step is as follows：
Prepare the fermentation culture medium of aspergillus (Aspergillus sp.) SCSIO 05879, isolated supernatant fermentation liquid and
Mycelium is precipitated, supernatant fermentation liquid is extracted with ethyl acetate, and fermentation liquid medicinal extract is concentrated under reduced pressure to obtain in acetic acid ethyl acetate extract；Precipitating
Mycelium is extracted with aqueous acetone solution ultrasound, and extracting solution is after being evaporated under reduced pressure, then is extracted with ethyl acetate, acetic acid ethyl acetate extract
Mycelium medicinal extract is concentrated under reduced pressure to obtain；Merge fermentation liquid medicinal extract and mycelium medicinal extract obtains coarse extract, separates, adopt through silica gel column chromatography
With methylene chloride/methanol from 100:0,99:1,98:2,97:3,95:5,90:10,80:20,50:50,0:100, v/v gradients are washed
It is de-, collect methylene chloride/methanol 100：0v/v elution component fr1, through Sephadex LH-20 column chromatograph, with methylene chloride/
Methanol 1:1, v/v is eluant, eluent, and the product after elution is purified to obtain Versicoloid A and Versicoloid B.
Purified Versicoloid A and the Versicoloid B that obtains of product after the elution is specifically with 250 Hes
340nm wavelength detects, using the flow velocity of 4mL/min, with methanol：Water (65:35, v/v) it carries out Gradient elution and carries out half system
Standby efficient liquid phase separates, HPLC (Sunfire, Prep C18OBD, 10 × 250mm, 5 μm), obtain Versicoloid A
(4.6mg, retention time tR22.6min) and Versicoloid B (6.1mg, retention time tR 16.1min)。
The fermentation culture medium for preparing aspergillus (Aspergillus sp.) SCSIO 05879 is preferably through following
Method preparation：Aspergillus (Aspergillus sp.) SCSIO 05879 of activation is accessed into seed culture medium, 28 DEG C, 180rpm,
Culture 48h obtains seed liquor, seed liquor is linked into fermentation medium with the inoculum concentration of volume ratio 5%, 28 DEG C, 180rpm is quiet
Culture 40 days is set, and fermentation culture medium is made, the formula of the seed culture medium and fermentation medium is all every liter of culture medium
In contain soluble starch 10g, fish peptone 1g, coarse sea salt 20g, surplus is water, pH 7.5.
Third object of the present invention is to provide aspergillus (Aspergillus sp.) SCSIO 05879 in prepare compound
Application in Versicoloids A or B.
The present inventor is found through experiments that compound Versicoloids A and B is to glue spore anthrax bacteria, rice blast
Bacterium and banana blight bacteria have apparent growth inhibitory activity, and MIC value is 1.6/1.6 μ g mL respectively-1、128/128μg mL-1With 64/64 μ g mL-1.Therefore, it is anti-in preparation to be to provide compound Versicoloids A or B for fourth object of the present invention
Application in bacterium drug.
The antibacterials are preferably the drug of anticol spore anthrax bacteria, rice blast fungus or banana blight bacteria.
Fifth object of the present invention is to provide a kind of antibacterials, which is characterized in that comprising a effective amount of
Versicoloids A or B are as active ingredient.
The antibacterials are preferably the drug of anticol spore anthrax bacteria, rice blast fungus or banana blight bacteria.
The present invention from aspergillus (Aspergillus sp.) SCSIO 05879 isolated 2 it is new with antibacterial activity
Alkaloid compound Versicoloids A and B, can be used to prepare antibacterials, be expected by bioengineering or chemical modification
It is developed into antibacterial new drug.
Aspergillus (Aspergillus sp.) SCSIO 05879 of the invention is the deposition for being -3927 meters from the Indian Ocean depth of water
Separation obtains in object (6 ° 00 ' 00 " N, 87 ° 30 ' 50 " E).
Aspergillus (Aspergillus sp.) SCSIO 05879 of the invention, is preserved in China on July 17th, 2015
Microbiological Culture Collection administration committee common micro-organisms center (CGMCC), city of BeiJing, China Chaoyang District North Star West Road 1 institute 3
Number Institute of Microorganism, Academia Sinica, deposit number are：CGMCC No.11123.
Detailed description of the invention：
The key of Fig. 1 compound Versicoloid A1H–1H COSY, HMBC is related to NOE.
The actual measurement CD and calculating ECD map of Fig. 2 compound Versicoloids A (1) and B (2).
Specific embodiment：
The following examples are further illustrations of the invention, rather than limiting the invention.
Embodiment 1：The separation and preparation of active metabolite Versicoloids A and B
1, seed culture medium and fermentation medium：Soluble starch 10g, fish peptone 1g, coarse sea salt 20g, water 1L,
PH7.5 adjusts pH value after mixing, sterilizes spare.
2, it ferments
2.1, seed culture：By the single colonie of the aspergillus activated on culture dish (Aspergillus sp.) SCSIO 05879
It is respectively connected to 30 bottles, in the taper culture bottle of every bottle of 250mL containing 50mL seed culture medium, 28 DEG C, 180rmin-1, culture
Seed liquor 1500mL is made in 48h.
2.2, fermented and cultured：Seed liquor is linked into 30L fermentation medium with 5% inoculum concentration (percent by volume) (to set
In the taper culture bottle of 1000mL, every bottle contains 300mL fermentation medium, and totally 100 bottles) in, 28 DEG C, 180rmin-1, stand
Culture 40 days, obtains 30L fermentation culture medium.
3, it extracts：(3500rmin is first centrifuged in fermentation culture medium-1, 8min), obtain the supernatant hair of 30L volume
Zymotic fluid and precipitating mycelium.With ethyl acetate equal-volume extraction 3 times, acetic acid ethyl acetate extract subtracts supernatant fermentation liquid lower than 40 DEG C
Pressure is concentrated to give fermentation liquid medicinal extract；The aqueous acetone solution ultrasound extraction of mycelium volume fraction 85% is precipitated, extracting solution is through depressurizing
It after distillation, then is extracted repeatedly three times with ethyl acetate, acetic acid ethyl acetate extract is concentrated under reduced pressure to obtain mycelium leaching at lower than 40 DEG C
Cream；Merge fermentation liquid medicinal extract and mycelium medicinal extract amounts to obtain about 18.3g coarse extract.
4, the extraction separation and identification of reactive compound
The extraction of 4.1 compound Versicoloids A and B separates and identification：Coarse extract 300-400 mesh silica gel column layer
Analysis separation, after being mixed sample, dry column-packing, using methylene chloride/methanol from 100:0,99:1,98:2,97:3,95:5,90:10,
80:20,50:50,0:100, v/v gradient elutions sequence obtains 6 components (fr1-fr6).Component fr1 (methylene chloride/methanol 100：
The component of 0v/v elution) it is chromatographed through Sephadex LH-20 column, with methylene chloride/methanol (1:1, v/v) it is eluant, eluent, elutes pure
Product after change is detected, using the flow velocity of 4mL/min with 250 and 340nm wavelength, with methanol：Water (65:35, v/v) it carries out
Gradient elution carries out half preparation efficient liquid phase separation, HPLC (Sunfire, Prep C18OBD, 10 × 250mm, 5 μm), obtain
Versicoloid A (4.6mg, retention time tR22.6min) and Versicoloid B (6.1mg, retention time tR
16.1min).By structural analysis, to the fermented and cultured of the invention from aspergillus (Aspergillus sp.) SCSIO 05879
The two compound-compounds 1 (corresponding compound Versicoloid A) and (the corresponding chemical combination of compound 2 being prepared in object
Object Versicoloid B) (formula (I)) identify that it, qualification result is as follows：
Compound 1 (Versicoloid A)：Yellow oil,1H NMR(500MHz,DMSO-d6) and13C NMR
(125MHz,DMSO-d6) data, it is shown in Table 1；HRESIMS m/z 382.1726[M+Na]+(calcd for C19H25N3NaO4,
382.1737)。
The high-resolution electrospray ionization mass spectrum figure of compound 1 shows that its quasi-molecular ion peak is m/z [M+Na]+382.1726, it pushes away
Surveying its molecular formula is C19H25N3O4(degree of unsaturation 9).Analysis1H,13C and HSQC (table 1) are statistics indicate that the compound contains 5
Methyl [δH 3.64(H3- 20), 1.07 (d, J=6.9, H3- 19), 0.96 (d, J=6.4, H3- 23), 0.91 (d, J=6.4, H3-
, and 0.81 (t, J=6.9, H 22)3- 22)], 1 sp3The methylene of hydridization, 3 sp2The methine of hydridization, 4 sp3Hydridization
Methine, 6 sp2The quaternary carbon of hydridization.By HMQC spectrogram,1H-1H COSY map, HMBC spectrogram (Fig. 1) are analysis shows that chemical combination
Object 1 and known compound Oxepinamides B [Chem.Eur.J.2000,6 (8):1355-1360] much like, thus it is speculated that being
The valine residue in object 1 is closed instead of the alanine residue part in known compound Oxepinamides B.It is composed in HMBC
In figure, there is crucial H-15 and C-1, the coherent signal of C-4 and C-13 and H-3 and C-16, C-17 and C-19, it was demonstrated that
The presence of valine residue.Further Noesy spectrogram is shown, it can be observed that the coherent signal of H-3 and H-21, thus it is speculated that H-
Heteropleural of the 3 and H-15 in piperazine hexatomic ring.Simultaneously by calculating the ECD spectrogram (Fig. 2) of compound 1, in conjunction with its biosynthesis way
Its absolute configuration is speculated as 3R and 15S by diameter.
The structure of Versicoloid A is as follows：
Compound 2 (Versicoloid B)：Yellow oil,1H NMR(500MHz,DMSO-d6) and13C NMR
(125MHz,DMSO-d6) data, it is shown in Table 1；HRESIMS m/z 398.1689[M+Na]+(calcd for C19H25N3NaO5,
398.1686)。
The high-resolution electrospray ionization mass spectrum figure of compound 2 shows that its quasi-molecular ion peak is m/z [M+Na]+398.1689, it pushes away
Surveying its molecular formula is C19H25N3O5(degree of unsaturation 9).Analysis1H,13C and HMQC (table 1) are statistics indicate that compound 2 and compound
It is closely similar in 1 structure, an oxygen atom is only differed on molecular weight.It further analyzes one-dimensional1H and13C spectrum discovery, compound 2
Than 1 few sp of compound3The methine of hydridization, more sp3The quaternary carbon of hydridization, and be even oxygen quaternary carbon, binding molecule formula speculates
It is the hydroxyl on 3 instead of 3 in compound 1 hydrogen atoms.Crucial HMBC coherent signal H2- 17 and H3- 19 with C-3's
Correlation demonstrates the correctness of the above supposition.- 114.9 ° of the optically-active data OR (c 0.3, MeOH) of compound 2 and circular dichroism spectra number
According to CD (c 0.02, MeOH) (Δ ε) 218 (+20.6), 245 (- 14.9) determine spatial configuration and 1 optically-active of compound of compound 2
- 239.4 ° of data OR (c 0.4, MeOH) and CD (c 0.02, MeOH) (Δ ε) 219 (+13.6), 2248 (- 16.4) unanimously,
Absolute configuration is equally speculated as 3R and 15S.
The structure of Versicoloid B is as follows：
The nuclear magnetic data of table 1. compound Versicoloids A and B belong to (CD3OD,500MHz)
Embodiment 2：The measurement of the bacteriostatic activity of Versicoloids A and B
Versicoloids A and B are directed to three kinds of phytopathogens：Glue spore anthrax bacteria, rice blast fungus and banana are withered
The germ that withers has carried out determination of activity, experimental method bibliography [Dang Q L., Shin T S., Park M S., Choi Y
H.,Choi G J.,Jang K S.,Kim I S.,Kim J C.,Antimicrobial activities of novel
mannosyl lipids is olated from the biocontrol fungus Simplicillium
lamellicola BCP against phytopathogenic bac teria.J.Agric.Food Chem.,2014,62,
3363–3370].With cycloheximide make positive control (to glue spore anthrax bacteria, rice blast fungus, banana blight bacteria MIC
Value is 6.4 μ g mL respectively-1、12.8μg mL-1With 12.8 μ g mL-1).The result shows that Versicoloids A is to glue spore anthracnose
The MIC value of bacterium, rice blast fungus and banana blight bacteria is 1.6 μ g mL respectively-1、128μg mL-1With 64 μ g mL-1；
Versicoloids B is 1.6 μ g mL respectively to the MIC value of glue spore anthrax bacteria, rice blast fungus and banana blight bacteria-1、128μg mL-1With 64 μ g mL-1.Versicoloi ds A and B is presented with growth inhibition to the three kinds of phytopathogens surveyed
Activity is expected to be developed into anti-phytopathogen new drug by bioengineering or chemical modification.
Claims (2)
1. aspergillus (Aspergillus sp.) SCSIO 05879, deposit number are：CGMCC No.11123.
2. aspergillus (Aspergillus sp.) SCSIO 05879 described in claim 1 is in prepare compound Versicoloid
Application in A or B, compound the Versicoloids A or B, shown in structure such as formula (I)：
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| CN201710505896.2A CN107266460B (en) | 2016-01-22 | 2016-01-22 | Marine aspergillus SCSIO 05879 prepares Versicoloids A and B and the application in anti-colletotrichum gloeosporioides Penz drug |
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| CN201710505896.2A CN107266460B (en) | 2016-01-22 | 2016-01-22 | Marine aspergillus SCSIO 05879 prepares Versicoloids A and B and the application in anti-colletotrichum gloeosporioides Penz drug |
| CN201610046509.9A CN105713002B (en) | 2016-01-22 | 2016-01-22 | Antibiotic Versicoloids A and B and preparation method thereof and the application in anti-phytopathogen medicine is prepared |
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| CN101456863A (en) * | 2007-12-14 | 2009-06-17 | 华北制药集团新药研究开发有限责任公司 | Novel LXR agonist as well as preparation method and application thereof |
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| CN101456863A (en) * | 2007-12-14 | 2009-06-17 | 华北制药集团新药研究开发有限责任公司 | Novel LXR agonist as well as preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| Janoxepin and brevicompanine B: Antiplasmodial metabolites from the fungus Aspergillus janus;Kennett Sprogoe，等;《Tetrahedron》;20050721;第61卷(第36期);第8718-8721页 * |
| Oxepinamides A-C and fumiquinazolines H-I: bioactive metabolites from a marine isolate of a fungus of the genus Acremonium;Gilbert N. Belofsky，等;《Chem. Eur. J.》;20000831;第6卷(第8期);第1355-1360页 * |
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