CN108640897A - Polyketides and the preparation method and application thereof in a kind of mangrove endogenetic fungus - Google Patents
Polyketides and the preparation method and application thereof in a kind of mangrove endogenetic fungus Download PDFInfo
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- CN108640897A CN108640897A CN201810390127.7A CN201810390127A CN108640897A CN 108640897 A CN108640897 A CN 108640897A CN 201810390127 A CN201810390127 A CN 201810390127A CN 108640897 A CN108640897 A CN 108640897A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
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- A61P31/04—Antibacterial agents
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- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
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- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
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Abstract
The present invention relates to polyketides in a kind of mangrove endogenetic fungus and the preparation method and application thereof, more particularly to a pair of diastereoisomeric polyketides or its pharmaceutically acceptable salt, it is characterised in that diastereoisomeric polyketides have structure shown in compound 1,2.
Description
Technical field
The invention belongs to mangrove endogenetic fungus secondary metabolite fields, and in particular to polyketone in a kind of mangrove endogenetic fungus
Class compound and the preparation method and application thereof.
Background technology
One of unique compound important sources of endogenetic fungus structure novel activity of marine source.In recent years, some are new
Reactive compound it is isolated from fungi D.eschscholtzii, such as：Immunosuppressive activity compound
Dalesconols A-B and spirodalesol, the compound selesconol of differentiation of stem cells have cytotoxic activity
Compound daldinone F, antifungal compound helicascolide C.Early-stage study finds endogenetic fungus
D.eschscholtzii ethyl acetate extracts have certain antibacterial activity.
Invention content
Mangrove endogenetic fungus of the present invention is isolated from mangrove cusp sea lotus endogenetic fungus (Daldinia
Eschscholtzii) its gene order has been filed on to NCBI, Gene Bank：MH059553.1, LOCUS:MH059553, with
The lower mangrove endogenetic fungus is indicated with Daldinia eschscholtzii.
The present invention provides a pair of diastereoisomeric polyketides or its pharmaceutically acceptable salt, it is characterised in that
Diastereoisomeric polyketides have structure shown in compound 1,2：
Another embodiment of the present invention provides the preparation method of above compound 1,2, it is characterised in that including walking as follows
Suddenly：
(1) prepare seed culture medium, by Daldinia eschscholtzii bacterial strains access seed culture medium, 26~28
DEG C, culture obtains seed culture fluid in 3~4 days；
(2) in the seed culture fluid access fermentation medium obtained step (1), 26~28 DEG C of stationary cultures 21~24 days
Obtain fermentate；
(3) zymotic fluid in the fermentate for obtaining step (2) and thalline separation, zymotic fluid and thalline are used isometric respectively
Ethyl acetate extract 3~5 times, medicinal extract is concentrated under reduced pressure to give after combining extraction liquid；
(4) medicinal extract that step (3) obtains presses 100 by decompression silica gel column chromatography, using petroleum ether-ethyl acetate:0 to 0:
100 gradient elutions, wherein 20% ethyl acetate-light petrol elution fraction is through Sephadex LH-20 gel filtration chromatographies, eluant, eluent
For petroleum ether：CHCl3: MeOH=2：1: 1, then prepared through high-efficient liquid phase chromatogram HPLC, chromatographic column is Agilent C18,9.4 ×
250mm, 7 μm, flow velocity 2mL/min, mobile phase MeOH: H2O=85: 15 finally obtain above compound 1,2.
The ratio of the wherein described eluant, eluent or mobile phase is volume ratio；Contain glucose in the seed culture medium
1.5% -3.0%, yeast extract 0.1% -0.5%, peptone 0.1% -0.5%, coarse sea salt 0.11% -0.6%, suitable water；
Contain glucose 1.6% -3.5%, yeast extract 0.1% -0.5%, peptone 0.1% -0.5%, thick in the fermentation medium
Sea salt 0.11% -0.6%, suitable water；Above-mentioned percentage is weight percentage；The seed culture medium and fermentation medium
120 DEG C are both needed to go out 25-30 minutes.
The present invention provides a kind of pharmaceutical composition, it is characterised in that with above compound 1,2 of the present invention or its pharmaceutically may be used
The salt of receiving is as active constituent.
Aforementioned pharmaceutical compositions provided by the invention also may include other antibacterials；Can also include that can pharmaceutically connect
The auxiliary material (preferably pharmaceutically acceptable carrier, diluent or excipient) received.The dosage form of aforementioned pharmaceutical compositions can be solid
Body preparation, semisolid preparation or liquid preparation.
Another embodiment of the present invention provides above compound 1,2 or its pharmaceutically acceptable salt in medicine preparation
Purposes.
Another embodiment of the present invention provides above compound 1,2 or its pharmaceutically acceptable salt is preparing antimicrobial
Purposes in object.
Term " pharmaceutically acceptable salt " refers to the addition of atoxic inorganic or organic acid and/or alkali in the present invention
Salt, reference can be made to " Salt selection for basic drugs ", Int.J.Pharm. (1986), 33,201-217.
Description of the drawings
Fig. 1 is the ECD spectrograms of compound 1
Fig. 2 is the ECD spectrograms of compound 2
Specific implementation mode
For the ease of a further understanding of the present invention, examples provided below has done more detailed description to it.But
It is that these embodiments are only not supposed to be a limitation to the present invention or implementation principle for being better understood from invention, reality of the invention
The mode of applying is not limited to the following contents.
Embodiment 1
(1) Spawn incubation of Daldinia eschscholtzii
Prepare seed culture medium：Glucose 80g, peptone 8g, yeast extract 8g, coarse sea salt 10g, water 4.0L are average to dispense
In 8 1000mL conical flasks, 120 DEG C go out 25-30 minutes.
Daldinia eschscholtzii bacterial strains are accessed in prepared seed culture medium, at 26~28 DEG C, training
Support 3 days to obtain seed culture fluid；
(2) fermentation of Daldinia eschscholtzii
Prepare fermentation medium：Glucose 1.1kg, peptone 100g, yeast extract 100g, sea salt 125g, water 50L are average
It is sub-packed in 75 1000mL conical flasks, 120 DEG C go out 25-30 minutes.
The seed culture fluid that is obtained in appropriate step (1) is taken to access in the conical flask equipped with fermentation medium, in 26~
28 DEG C of stationary cultures 21 days.
(3) the extraction separation of compound 1,2
Take the fermentate filtering that step (2) obtains, separation and fermentation liquid and thalline, after filtrate is concentrated, use respectively isometric
Ethyl acetate extraction concentration after filtrate and each 3 times of thalline；Combining extraction liquid is adopted by depressurizing silica gel column chromatography after concentration
100 are pressed with petroleum ether-ethyl acetate:0 to 0:100 gradient elutions, wherein 20% ethyl acetate-light petrol elution fraction passes through
Sephadex LH-20 gel filtration chromatographies, eluant, eluent are petroleum ether：CHCl3: MeOH=2：1: 1, then through high performance liquid chromatography
Prepared by HPLC, chromatographic column is Agilent C18,9.4 × 250mm, 7 μm, flow velocity 2mL/min, mobile phase MeOH: H2O=
85: 15, finally obtain compound 1 (12.0mg), 2 (11.5mg).
1 compound 1 and 2 of table1H and13C-NMR(400/100MHz,CDCl3) data (ppm)
Compound 1：High resolution mass spectrum data 357.1693 [M+H]+, theoretical value is 357.1697 [M+H]+。
Compound 2：High resolution mass spectrum data 357.1693 [M+H]+, theoretical value is 357.1697 [M+H]+。
Further according to two-dimentional nuclear magnetic spectrum1H-1H COSY, HMQC and HMBC determine the relative configuration of compound 1,2.
Determine that absolute configuration, the absolute configuration of compound 1 and 2 are determined by ECD calculating.It is close when being contained using ECD
Spend the calculating that Functional Theory method (TDDFT) carries out compound 1 and 2 ECD curves.The ECD curves of the 1'R of calculating, 3'S configuration
The ECD curves obtained with 1 experiment test of compound match, and the 1'R calculated, ECD curves and the compound 2 of 3'R configurations are surveyed
The absolute configuration that the ECD curves of examination match, therefore also determine compound 1 and 2 is respectively 1'R, 3'S and 1'R, 3'R.
Embodiment 2
(1) Spawn incubation of Daldinia eschscholtzii
Prepare seed culture medium (5.0L)：Glucose 1.5% (weight percent, similarly hereinafter), yeast extract 0.5%, peptone
0.1%, coarse sea salt 0.11%, remaining is water；Average mark is loaded on 8 1000mL conical flasks, and 120 DEG C go out 25-30 minutes.
Daldinia eschscholtzii bacterial strains are accessed in prepared seed culture medium, at 26~28 DEG C, training
Support 4 days to obtain seed culture fluid；
(2) fermentation of Daldinia eschscholtzii
Prepare fermentation medium (100L)：Glucose 1.6% (weight percent, similarly hereinafter), yeast extract 0.5%, peptone
0.1%, coarse sea salt 0.11%, remaining is water；Average mark is loaded on 150 1000mL conical flasks, and 120 DEG C go out 25-30 minutes.
The seed culture fluid that is obtained in appropriate step (1) is taken to access in the conical flask equipped with fermentation medium, in 26~
28 DEG C of stationary cultures 24 days.
(3) the extraction separation of compound 1,2
According to separation method similar in embodiment 1, compound 1 and 2, structural identification data and embodiment 1 one can be obtained
It causes.
Embodiment 3
(1) Spawn incubation of Daldinia eschscholtzii
Prepare seed culture medium (1.0L)：Glucose 3.0% (weight percent, similarly hereinafter), yeast extract 0.1%, peptone
0.5%, coarse sea salt 0.6%, remaining is water；Average mark is loaded on 3 500mL conical flasks, and 120 DEG C go out 25-30 minutes.
Daldinia eschscholtzii bacterial strains are accessed in prepared seed culture medium, at 26~28 DEG C, training
Support 4 days to obtain seed culture fluid；
(2) fermentation of Daldinia eschscholtzii
Prepare fermentation medium (20L)：Glucose 3.5% (weight percent, similarly hereinafter), yeast extract 0.1%, peptone
0.5%, coarse sea salt 0.6%, remaining is water；Average mark is loaded on 30 1000mL conical flasks, and 120 DEG C go out 25-30 minutes.
The seed culture fluid that is obtained in appropriate step (1) is taken to access in the conical flask equipped with fermentation medium, in 26~
28 DEG C of stationary cultures 22 days.
(3) the extraction separation of compound 1,2
According to separation method similar in embodiment 1, compound 1,2, structural identification data and embodiment 1 one can be obtained
It causes.
The measurement of the antibacterial activity of 4 the compounds of this invention 1,2 of embodiment
Test method：1,2 pair of 6 plants of pathogenic bacteria of compound are taken to carry out active testing, 6 plants of pathogenic bacteria include that 2 plants of oceans are caused a disease
Bacterium and 4 plants of land pathogenic bacteria, respectively vibrio alginolyticus (Vibrio alginolyticus), vibrio parahemolyticus (Vibrio
Parahaemolyticus), staphylococcus aureus (Staphylococcus aureus), methicillin-resistant staphylococcus grape
Coccus (Methicillin-resistant S.aureus), Escherichia coli (Escherichia coli), bacillus cereus
(Bacillus cereus)。
The bacterium solution of 190 μ L is added in the first row of 96 orifice plates, 100 μ L bacterium solutions are added in remaining each row.In sample well and
It is separately added into the corresponding samples to be tested of 10 μ L and positive drug in the first row of Positive control wells, is taken out after carrying out mixing with the volley of rifle fire
100 μ L are added to second row, are added to third row after mixing again, and mixing dilutes eight gradients by row successively, and positive control is dilute
12 gradients are released, bacterium solution is finally added into 200 μ L in all holes.Blank control is 200 μ L blank culture solutions, and negative control is
10 μ L DMSO and 190 μ L bacterium solutions.96 orifice plates are placed into overnight incubation at room temperature.96 orifice plates are placed under microplate reader (492nm) and are surveyed
Absorbance is tried, MIC value is calculated.Ciprofloxacin is positive control drug.
Test result is as follows：
Table 2：
In upper table：MIC：Minimal inhibitory concentration (minimum inhibitory concentration).
CiprofloxacinaFor positive control.
Test result shows that two compounds have certain antibacterial activity, to S.aureus, MRSA, B.cereus bacterial strains tool
There are preferable inhibitory activity, MIC value 6.15-12.5.
Claims (10)
1. a pair of diastereoisomeric polyketides or its pharmaceutically acceptable salt, it is characterised in that the diastereomeric is different
The polyketides of structure have structure shown in compound 1,2：
2. preparation method that is a kind of while preparing diastereomeric compounds 1,2 described in claim 1, it is characterised in that including
Following steps：
(1) seed culture medium is prepared, Daldinia eschscholtzii bacterial strains are accessed into seed culture medium, 26~28 DEG C, are trained
Support 3~4 days to obtain seed culture fluid；
(2) in the seed culture fluid access fermentation medium obtained step (1), 26~28 DEG C of stationary cultures must be sent out for 21~24 days
Ferment object；
(3) zymotic fluid in the fermentate for obtaining step (2) and thalline separation, zymotic fluid and thalline are respectively with isometric second
Acetoacetic ester extracts 3~5 times, and medicinal extract is concentrated under reduced pressure to give after combining extraction liquid；
(4) medicinal extract that step (3) obtains presses 100 by decompression silica gel column chromatography, using petroleum ether-ethyl acetate:0 to 0: 100
Gradient elution, wherein 20% ethyl acetate-light petrol elution fraction, through Sephadex LH-20 gel filtration chromatographies, eluant, eluent is stone
Oily ether：CHCl3: MeOH=2：1: 1, then prepared through high-efficient liquid phase chromatogram HPLC, chromatographic column is Agilent C18,9.4 ×
250mm, 7 μm, flow velocity 2mL/min, mobile phase MeOH: H2O=85: 15 finally obtain above compound 1,2.
3. the preparation method described in claim 2, it is characterised in that contain glucose 1.5%-in the seed culture medium
3.0%, yeast extract 0.1% -0.5%, peptone 0.1% -0.5%, coarse sea salt 0.11% -0.6%, suitable water；The hair
Contain glucose 1.6% -3.5%, yeast extract 0.1% -0.5%, peptone 0.1% -0.5%, coarse sea salt in ferment culture medium
0.11% -0.6%, suitable water；Above-mentioned percentage is weight percentage.
4. claim 2-3 any one of them preparation methods, it is characterised in that the seed culture medium and fermentation medium are equal
120 DEG C are needed to go out 25-30 minutes.
5. a kind of pharmaceutical composition, it is characterised in that compound 1,2 described in claim 1 or its pharmaceutically acceptable salt are made
For active constituent.
6. the pharmaceutical composition described in claim 5, it is characterised in that also may include other antibacterials.
7. claim 5-6 any one of them pharmaceutical compositions, it is characterised in that also may include pharmaceutically acceptable auxiliary material.
8. the pharmaceutical composition described in claim 7, it is characterised in that the pharmaceutically acceptable auxiliary material, which is selected from, pharmaceutically may be used
Carrier, diluent or the excipient of receiving.
9. claim 5-8 any one of them pharmaceutical compositions, it is characterised in that the dosage form of described pharmaceutical composition can be
Solid pharmaceutical preparation, semisolid preparation or liquid preparation.
10. the purposes of compound 1,2 described in claim 1 or its pharmaceutically acceptable salt in medicine preparation.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110229131A (en) * | 2019-07-17 | 2019-09-13 | 海南师范大学 | The chromone derivatives and the preparation method and application thereof in ceriops tagal endogenetic fungus source |
| CN110257255A (en) * | 2019-05-22 | 2019-09-20 | 海南师范大学 | The chromone derivatives and the preparation method and application thereof in mangrove cusp sea lotus endogenetic fungus source |
| CN110283728A (en) * | 2019-05-22 | 2019-09-27 | 海南师范大学 | The tetralone derivative and the preparation method and application thereof in mangrove cusp sea lotus endogenetic fungus source |
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| CN106434783A (en) * | 2016-04-05 | 2017-02-22 | 广东工业大学 | Benzopyrone compound, benzopyrone compound preparation method and application of benzopyrone compound to preparation of antibacterial medicines |
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2018
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106434783A (en) * | 2016-04-05 | 2017-02-22 | 广东工业大学 | Benzopyrone compound, benzopyrone compound preparation method and application of benzopyrone compound to preparation of antibacterial medicines |
Non-Patent Citations (2)
| Title |
|---|
| GANG WANG等: "Polyketides from Mantis-Associated Fungus Daldinia eschscholzii IFB-TL01", 《CHEMISTRY & BIODIVERSITY》 * |
| JINGQIU DAI等: "New Naphthalene-Chroman Coupling Products from the Endophytic Fungus,Nodulisporium sp. from Erica arborea", 《EUR. J. ORG. CHEM.》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110257255A (en) * | 2019-05-22 | 2019-09-20 | 海南师范大学 | The chromone derivatives and the preparation method and application thereof in mangrove cusp sea lotus endogenetic fungus source |
| CN110283728A (en) * | 2019-05-22 | 2019-09-27 | 海南师范大学 | The tetralone derivative and the preparation method and application thereof in mangrove cusp sea lotus endogenetic fungus source |
| CN110283728B (en) * | 2019-05-22 | 2020-09-29 | 海南师范大学 | Tetralone derivative derived from rosette valve and lotus endophytic fungi as well as preparation method and application thereof |
| CN110229131A (en) * | 2019-07-17 | 2019-09-13 | 海南师范大学 | The chromone derivatives and the preparation method and application thereof in ceriops tagal endogenetic fungus source |
| CN110229131B (en) * | 2019-07-17 | 2020-10-27 | 海南师范大学 | Benzopyrone derivative derived from cerasus humilis endophytic fungi as well as preparation method and application thereof |
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Application publication date: 20181012 |