CN110283728A - The tetralone derivative and the preparation method and application thereof in mangrove cusp sea lotus endogenetic fungus source - Google Patents
The tetralone derivative and the preparation method and application thereof in mangrove cusp sea lotus endogenetic fungus source Download PDFInfo
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Abstract
The present invention relates to the tetralone derivative and the preparation method and application thereof in mangrove cusp sea lotus endogenetic fungus source, the tetralone derivative has structure shown in compound 1-5:
Description
Technical field
The invention belongs to mangrove endogenetic fungus secondary metabolite fields, and in particular to mangrove cusp sea lotus endogenetic fungus comes
The tetralone derivative in source and the preparation method and application thereof.
Background technique
One of unique compound important sources of endogenetic fungus structure novel activity of marine source, applicant is previously from red
It sets separation in cusp sea lotus endogenetic fungus TGM112 and obtains the active mixed first terpenoid of series pesticide.The present invention is from another strain
Separation obtains serial tetralone derivative in mangrove cusp sea lotus endogenetic fungus (CGMCC No.17674).
Summary of the invention
The present invention provides a kind of mangrove cusp sea lotus endogenetic fungus, it is characterised in that its culture presevation information: depositary institution
Title: China Committee for Culture Collection of Microorganisms's common micro-organisms center;Depositary institution address: the Chaoyang District, Beijing City North Star
The institute 3 of West Road 1, Institute of Microorganism, Academia Sinica;Preservation date: on April 24th, 2019;Deposit number: CGMCC
No.17674;Classification naming: Daldinia eschscholtzii.
Another embodiment of the present invention provides the tetralone derivative in above-mentioned mangrove cusp sea lotus endogenetic fungus source
Or its pharmaceutically acceptable salt, it is characterised in that the tetralone derivative has structure shown in compound 1-5:
Another embodiment of the present invention provides above-mentioned mangrove cusp sea lotus endogenetic fungus and spreads out preparing above-mentioned tetralone
Application in biology.
Another implementation of the invention provide it is a kind of using above-mentioned mangrove cusp sea lotus endogenetic fungus simultaneously prepare compound 1-5
Preparation method, it is characterised in that include the following steps:
(1) prepare seed culture medium, by above-mentioned mangrove cusp sea lotus endogenetic fungus access seed culture medium, 26~28 DEG C,
Obtain seed culture fluid within culture 3~4 days;
(2) in the seed culture fluid access fermentation medium obtained step (1), 26~28 DEG C stationary culture 21~24 days
Obtain fermentation material;
(3) fermentation liquid in the fermentation material for obtaining step (2) and thallus separation, the isometric ethyl acetate of fermentation liquid
Extraction 3~5 times, is concentrated under reduced pressure to give medicinal extract after combining extraction liquid;Compound 1-5 is obtained through chromatographic isolation.
Contain glucose 1.5% -3.0%, yeast extract 0.1% -0.5%, peptone in step (1) described seed culture medium
0.1% -0.5%, coarse sea salt 0.11% -0.6%, suitable water;Contain glucose in step (2) described fermentation medium
1.6% -3.5%, yeast extract 0.1% -0.5%, peptone 0.1% -0.5%, coarse sea salt 0.11% -0.6%, suitable water;
Above-mentioned percentage is weight percentage;The seed culture medium and fermentation medium are both needed to 120 DEG C and go out 25-30 minutes;Step
(3) the preferred normal-phase silica gel column chromatography of the chromatographic isolation, reversed silica gel column chromatography, LH-20 gel filtration chromatography, efficient liquid phase HPLC
One or more of preparation combines.
Another embodiment of the present invention provides above-mentioned tetralone derivative or prepared by its pharmaceutically acceptable salt
Application in prevention and/or treatment diabetes medicament.
Another embodiment of the present invention provides above-mentioned tetralone derivative or prepared by its pharmaceutically acceptable salt
Application in alpha-glucosidase restrainer.
A kind of pharmaceutical composition, it is characterised in that the pharmaceutical composition with above-mentioned tetralone derivative or its pharmaceutically may be used
The salt of receiving is as effective component.The pharmaceutical composition may also include other preventions and/or treatment diabetes medicament.The medicine group
Closing object may also include the auxiliary material that can pharmaceutically connect.The preferred solid pharmaceutical preparation of the dosage form of the pharmaceutical composition or liquid preparation etc..
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.
It should be understood that within the scope of the present invention, above-mentioned each technical characteristic of the invention and in below (eg embodiment) specifically
Each technical characteristic of description can be combined with each other, to form a new or preferred technical solution.As space is limited, not another herein
One tired states.
Detailed description of the invention
Fig. 1 is compound 1-51H-1H COSY figure related to HMBC;
Fig. 2 is the ECD spectrogram of compound 1 and 2;
Fig. 3 is the ECD figure of compound 3;
Fig. 4 is the ECD spectrogram of compound 4;
Fig. 5 is the colony characteristics figure of mangrove cusp of the present invention sea lotus endogenetic fungus (CGMCC No.17674).
Specific embodiment
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 better understanding invention, reality of the invention
The mode of applying is not limited to the following contents.
Embodiment 1
(1) Spawn incubation
Prepare seed culture medium: glucose 80g, peptone 8g, yeast extract 8g, coarse sea salt 10g, water 4.0L, average packing
In 8 1000mL conical flasks, 120 DEG C go out 25-30 minutes.
Mangrove cusp sea lotus endogenetic fungus (CGMCC No.17674) is accessed in prepared seed culture medium, in 26~
At 28 DEG C, seed culture fluid is obtained within culture 3 days;
(2) it ferments
Preparation 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 access of seed culture fluid obtained in appropriate step (1) is taken equipped in the conical flask of fermentation medium, in 26~
28 DEG C obtain fermentation material in stationary culture 21 days.
(3) it isolates and purifies
Fermentation liquid in fermentation material and the thallus separation that step (2) is obtained, the isometric ethyl acetate extraction of fermentation liquid
It takes 3 times, medicinal extract is concentrated under reduced pressure to give after combining extraction liquid;Decompression silica gel column chromatography is first passed through, is pressed using petroleum ether-ethyl acetate
100:0,90:10,80:20,70:30,60:40,50:50,40:60,30:70,20:80,10:90,0:100 gradient elution, often
A gradient collects two column volumes, through reversed silica gel column chromatography, eluant, eluent after the fraction concentration that wherein 30:70 gradient elution obtains
For methanol: water=1:1-1:0, then prepared through high-efficient liquid phase chromatogram HPLC, chromatographic column is the μ of Agilent C18,9.4 × 250mm, 7
M, flow velocity 2mL/min, mobile phase MeOH:H2O=55:45 finally obtains compound 2 (3.5mg), 3 (6.3mg), 4
(8.1mg);Through Sephadex LH-20 gel filtration chromatography after the fraction concentration that wherein 40:60 gradient obtains, eluant, eluent is chloroform:
Methanol=1:1 obtains compound 1 (7.3mg) and 5 (10.4mg);The ratio of the eluant, eluent or mobile phase is volume ratio.Change
The structural identification data for closing object 1-5 is as follows:
Compound 1:[α]25 D-14.4(c 0.12,MeOH);UV(MeOH)λmax(logε)221,254,300nm;IR
(KBr)νmax 3400,3263,2974,1685,1612cm-1;CD(c 0.3,MeOH)λmax(Δε)204(+10.57),259(-
9.63),304(+3.60)nm;1H and 13C NMR is shown in Table 1-2;HR-ESI-MS m/z:223.0964[M+H]+,(C12H15O4,
calcd for 223.0965).
Compound 2:[α]25 D-14.0(c 0.20,MeOH);UV(MeOH)λmax(logε)221,254,300nm;IR
(KBr)νmax 3400,3263,2974,1685,1612,1495cm-1;CD(c 0.4,MeOH)λmax(Δε)204(+14.9),
261(-12.5),304(+6.9)nm;1H and 13C NMR is shown in Table 1-2;HR-ESI-MS m/z:251.1273[M+H]+,
(C14H19O4,calcd for 251.1278).
Compound 3:[α]25 D+35.6(c 0.15,MeOH);IR(KBr)νmax 3490,3400,2930,1670,1565,
1490cm-1;CD(c 0.52,MeOH)λmax(Δε)212(-28.98),236(+3.16),286(+11.60),344(-0.33)
nm;1H and 13C NMR is shown in Table 1-2;HR-ESI-MS m/z:265.1434[M+H]+,(C15H21O4,calcd for
265.1434).
Compound 4:[α]25 D-41.9(c 0.18,MeOH);IR(KBr)νmax 3490,3400,2930,1670,1565,
1490cm-1;CD(c 0.60,MeOH)λmax(Δε)212(-45.27),236(+8.21),286(+32.9),313(-21.86)
nm;1H and 13C NMR is shown in Table 1-2;HR-ESI-MS m/z:265.1434[M+H]+,(C15H21O4,calcd for
265.1434).
Compound 5:UV (MeOH) λmax(logε)221,254,300nm;IR(KBr)νmax 3250,2974,1685,
1612,1595cm-1;1H and 13C NMR is shown in Table 3;HR-ESI-MS m/z:277.1078[M+H]+,(C15H17O5,calcd
for 277.1071).
1. compound 1-4's of table1H NMR(400MHz,CDCl3)
2. compound 1-4's of table13C NMR(100MHz,CDCl3)
3. compound 5 of table1H (400MHz) and13C NMR(100MHz)DMSO-d6
Embodiment 2
According to Chinese invention patent application number: the method test the compounds of this invention 1-5 recorded in 201510880543.1
The IC that alpha-glucosidase is inhibited50, using Acarbose as positive control, as a result see the table below.
The IC of compound 150> 50, active testing is the result shows that 7 ethyls replace to alpha-glucosidase inhibition work in structure
Property is advantageous.
Claims (10)
1. a kind of mangrove cusp sea lotus endogenetic fungus, it is characterised in that its culture presevation information: depositary institution's title: the micro- life of China
Object culture presevation administration committee common micro-organisms center;Depositary institution address: Yard 1, BeiChen xi Road, Chaoyang District, Beijing City 3,
Institute of Microorganism, Academia Sinica;Preservation date: on April 24th, 2019;Deposit number: CGMCC No.17674;Classification life
Name: Daldinia eschscholtzii.
2. the tetralone derivative or its pharmaceutically acceptable salt in mangrove cusp sea lotus endogenetic fungus source, it is characterised in that
The tetralone derivative has structure shown in compound 1-5:
3. mangrove cusp described in claim 1 sea lotus endogenetic fungus is preparing tetralone derivative as claimed in claim 2
In application.
4. a kind of prepare chemical combination as claimed in claim 2 using mangrove cusp sea lotus endogenetic fungus described in claim 1 simultaneously
The preparation method of object 1-5, it is characterised in that include the following steps:
(1) seed culture medium is prepared, above-mentioned mangrove cusp sea lotus endogenetic fungus is accessed into seed culture medium, 26~28 DEG C, cultivates 3
Obtain seed culture fluid within~4 days;
(2) in the seed culture fluid access fermentation medium obtained step (1), 26~28 DEG C must send out for stationary culture 21~24 days
Ferment object;
(3) fermentation liquid in the fermentation material for obtaining step (2) and thallus separation, fermentation liquid are extracted with isometric ethyl acetate
3~5 times, medicinal extract is concentrated under reduced pressure to give after combining extraction liquid;Compound 1-5 is obtained through chromatographic isolation.
5. tetralone derivative as claimed in claim 2 or its pharmaceutically acceptable salt are in preparation prevention and/or treatment sugar
Urinate the application in medicine.
6. tetralone derivative as claimed in claim 2 or its pharmaceutically acceptable salt are preparing alpha-glucosidase inhibition
Application in agent.
7. a kind of pharmaceutical composition, it is characterised in that the pharmaceutical composition with tetralone derivative as claimed in claim 2 or
Its pharmaceutically acceptable salt is as effective component.
8. pharmaceutical composition as claimed in claim 7, it is characterised in that the pharmaceutical composition may also include other preventions and/or control
Treat diabetes medicament.
9. the described in any item pharmaceutical compositions of claim 7-8, it is characterised in that the pharmaceutical composition may also include pharmaceutically
The auxiliary material that can be connect.
10. the described in any item pharmaceutical compositions of claim 7-9, it is characterised in that the preferred solid of the dosage form of the pharmaceutical composition
Preparation or liquid preparation etc..
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CN115490661A (en) * | 2022-08-09 | 2022-12-20 | 海南师范大学 | Antioxidant active compound in mangrove-derived fungi and preparation method thereof |
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CN110257255B (en) * | 2019-05-22 | 2020-09-29 | 海南师范大学 | Benzopyrone derivative derived from endophytic fungi of mangrove cuspidate and lotus as well as preparation method and application thereof |
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