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CN109553600A - Isocoumarin class compound and the preparation method and application thereof in a kind of mangrove endogenetic fungus - Google Patents

Isocoumarin class compound and the preparation method and application thereof in a kind of mangrove endogenetic fungus Download PDF

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CN109553600A
CN109553600A CN201811476397.6A CN201811476397A CN109553600A CN 109553600 A CN109553600 A CN 109553600A CN 201811476397 A CN201811476397 A CN 201811476397A CN 109553600 A CN109553600 A CN 109553600A
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fermentation
seed culture
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CN109553600B (en
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郑彩娟
黄国雷
白猛
陈光英
王斌
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Hainan Normal University
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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
    • C07D311/76—Benzo[c]pyrans
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein

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  • Microbiology (AREA)
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  • Pest Control & Pesticides (AREA)
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  • Preparation Of Compounds By Using Micro-Organisms (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

本发明涉及一种红树内生真菌中异香豆素类化合物及其制备方法与应用，所述异香豆素类化合物具有化合物1‑8所示的结构： The invention relates to an isocoumarin compound in a mangrove endophyte and a preparation method and application thereof. The isocoumarin compound has the structure shown in compounds 1-8:

Description

Isocoumarin class compound and the preparation method and application thereof in a kind of mangrove endogenetic fungus
Technical field
The invention belongs to mangrove endogenetic fungus secondary metabolite fields, and in particular to an unusually sweet smell in a kind of mangrove endogenetic fungus Beans chlorins compound and the preparation method and application thereof.
Background technique
One of unique compound important sources of endogenetic fungus structure novel activity of marine source.In recent years, Yi Xiexin Reactive compound it is isolated from fungi Penicillum, such as: antiinflammatory active compound chrysogenester, Cytotoxic compound penicimenolides B-D and penitalarins A-C has active compound of killing virus Simpterpenoid A, antifungal compound brocapyrrozin A.Early-stage study finds endogenetic fungus Penicillum second Acetoacetic ester crude extract has certain antibacterial activity.
Summary of the invention
Mangrove endogenetic fungus (Penicillum, hereinafter referred to as TGM112) of the present invention is isolated from mangrove cusp sea Lotus, culture presevation information: depositary institution's title: China Committee for Culture Collection of Microorganisms's common micro-organisms center；It protects Hide unit address: Yard 1, BeiChen xi Road, Chaoyang District, Beijing City 3, Institute of Microorganism, Academia Sinica；Preservation date: 2018 On November 9, in；Deposit number: CGMCC No.16499；Classification naming: mould Penicillium sp..
The present invention provides a kind of isocoumarin class compound or its pharmaceutically acceptable salt, it is characterised in that an unusually sweet smell Beans chlorins compound has structure shown in compound 1-8:
Another embodiment of the present invention provides the preparation method of prepare compound 1-8 simultaneously a kind of, it is characterised in that packet Include following steps:
(1) seed culture medium is prepared, TGM112 bacterial strain is accessed into seed culture medium, 26~28 DEG C, culture must plant for 3~4 days Sub- culture solution；
(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, fermentation liquid and thallus are used in equal volume 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 100:0,90 by decompression silica gel column chromatography, using petroleum ether-ethyl acetate: 10,80:20,70:30,60:40,50:50,40:60,30:70,20:80,10:90,0:100 gradient elution, each gradient are collected Two column volumes, through Sephadex LH-20 gel filtration chromatography, eluant, eluent after the fraction concentration that wherein 20:80 gradient elution obtains For methanol: chloroform=1:1, then prepare through high-efficient liquid phase chromatogram HPLC, chromatographic column are Agilent C18,9.4 × 250mm, 7 μm, Flow velocity is 2mL/min, mobile phase CH3CN:H2O=45:55 finally obtains compound 1, compound 4, compound 5, compound 6 With compound 7；Through Sephadex LH-20 gel filtration chromatography after the fraction concentration that wherein 0:100 gradient obtains, eluant, eluent is first Alcohol: chloroform=1:1, then prepared through high-efficient liquid phase chromatogram HPLC, chromatographic column is Agilent C18,9.4 × 250mm, 7 μm, flow velocity For 2mL/min, mobile phase MeOH:H2O=45:55 finally obtains compound 2, compound 3 and compound 8.
Wherein the ratio of the 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 1-8 (especially compound of the present invention 1,2,5,6,8) or its pharmaceutically acceptable salt as active constituent.
Aforementioned pharmaceutical compositions provided by the invention also may include other insecticidal materials；Also may include 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 compound 1-8 (especially compound 1,2,5,6,8) or it pharmaceutically may be used The salt of receiving is preparing the purposes in insecticide.Especially the application in bollworm drug is killed in preparation.
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.
Detailed description of the invention
Fig. 1 is the ECD spectrogram of compound 1,2；
Fig. 2 is the ECD spectrogram of compound 3-7；
Fig. 3 is the ECD spectrogram of compound 8.
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 of TGM112
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.
TGM112 bacterial strain is accessed in prepared seed culture medium, at 26~28 DEG C, obtains seed culture within culture 3 days Liquid；
(2) fermentation of TGM112
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) preparation of medicinal extract
Fermentation liquid in fermentation material and the thallus separation that step (2) is obtained, fermentation liquid and thallus are used isometric respectively Ethyl acetate extracts 3 times, and medicinal extract is concentrated under reduced pressure to give after combining extraction liquid；
(4) the extraction separation of compound 1-8
Medicinal extract that step (3) obtains by decompression silica gel column chromatography, using petroleum ether-ethyl acetate by 100:0,90:10, 80:20,70:30,60:40,50:50,40:60,30:70,20:80,10:90,0:100 gradient elution, each gradient collect two A column volume, through Sephadex LH-20 gel filtration chromatography after the fraction concentration that wherein 20:80 gradient elution obtains, eluant, eluent is Methanol: chloroform=1:1, then prepared through high-efficient liquid phase chromatogram HPLC, chromatographic column is Agilent C18,9.4 × 250mm, 7 μm, stream Speed is 2mL/min, mobile phase CH3CN:H2O=45:55, finally obtain compound 1 (12.4mg), compound 4 (15.3mg), Compound 5 (18.2mg), compound 6 (9.6mg) and compound 7 (14.2mg)；After the fraction concentration that wherein 0:100 gradient obtains Through Sephadex LH-20 gel filtration chromatography, eluant, eluent is methanol: chloroform=1:1, then is prepared through high-efficient liquid phase chromatogram HPLC, color Composing column is Agilent C18,9.4 × 250mm, 7 μm, flow velocity 2mL/min, mobile phase MeOH:H2O=45:55 is final to be obtained To compound 2 (14.8mg), compound 3 (11.6mg) and compound 8 (16.4mg).
Compound 1-8's1H and13C-NMR(400/100MHz,aCD3OD.bDMSO-d6) data such as the following table 1, table 2.
1 compound 1-8's of table1H-NMR(400MHz,aCD3OD.bDMSO-d6) data (ppm)
2 compound 1-8's of table1H-NMR(100MHz,aCD3OD.bDMSO-d6) data (ppm)
Embodiment 2
(1) Spawn incubation of TGM112
It prepares seed culture medium (10.0L): 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 16 1000mL conical flasks, and 120 DEG C go out 25-30 minutes.
TGM112 bacterial strain is accessed in prepared seed culture medium, at 26~28 DEG C, obtains seed culture within culture 4 days Liquid；
(2) fermentation of TGM112
It prepares 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 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 24 days.
(3) preparation of medicinal extract
Fermentation liquid in fermentation material and the thallus separation that step (2) is obtained, fermentation liquid and thallus are used isometric respectively Ethyl acetate extracts 5 times, and medicinal extract is concentrated under reduced pressure to give after combining extraction liquid；
(4) the extraction separation of compound 1-8
Medicinal extract that step (3) obtains by decompression silica gel column chromatography, using petroleum ether-ethyl acetate by 100:0,90:10, 80:20,70:30,60:40,50:50,40:60,30:70,20:80,10:90,0:100 gradient elution, each gradient collect two A column volume, through Sephadex LH-20 gel filtration chromatography after the fraction concentration that wherein 20:80 gradient elution obtains, eluant, eluent is Methanol: chloroform=1:1, then prepared through high-efficient liquid phase chromatogram HPLC, chromatographic column is Agilent C18,9.4 × 250mm, 7 μm, stream Speed is 2mL/min, mobile phase CH3CN:H2O=45:55, finally obtain compound 1 (26.2mg), compound 4 (31.5mg), Compound 5 (37.0mg), compound 6 (20.5mg) and compound 7 (29.0mg)；The fraction concentration that wherein 0:100 gradient obtains By Sephadex LH-20 gel filtration chromatography, eluant, eluent is methanol: chloroform=1:1, then is 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=45:55 is final Obtain compound 2 (29.5mg), compound 3 (23.8mg) and compound 8 (33.2mg).
Embodiment 3
(1) Spawn incubation of TGM112
It prepares 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.
TGM112 bacterial strain is accessed in prepared seed culture medium, at 26~28 DEG C, obtains seed culture within culture 4 days Liquid；
(2) fermentation of TGM112
It prepares fermentation medium (10L): 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 15 1000mL conical flasks, and 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 22 days.
(3) preparation of medicinal extract
Fermentation liquid in fermentation material and the thallus separation that step (2) is obtained, fermentation liquid and thallus are used isometric respectively Ethyl acetate extracts 5 times, and medicinal extract is concentrated under reduced pressure to give after combining extraction liquid；
(4) the extraction separation of compound 1-8
Medicinal extract that step (3) obtains by decompression silica gel column chromatography, using petroleum ether-ethyl acetate by 100:0,90:10, 80:20,70:30,60:40,50:50,40:60,30:70,20:80,10:90,0:100 gradient elution, each gradient collect two A column volume, through Sephadex LH-20 gel filtration chromatography after the fraction concentration that wherein 20:80 gradient elution obtains, eluant, eluent is Methanol: chloroform=1:1, then prepared through high-efficient liquid phase chromatogram HPLC, chromatographic column is Agilent C18,9.4 × 250mm, 7 μm, stream Speed is 2mL/min, mobile phase CH3CN:H2O=45:55 finally obtains compound 1, compound 4, compound 5,6 and of compound Compound 7；Through Sephadex LH-20 gel filtration chromatography after the fraction concentration that wherein 0:100 gradient obtains, eluant, eluent is methanol: Chloroform=1:1, then prepared through high-efficient liquid phase chromatogram HPLC, chromatographic column is Agilent C18,9.4 × 250mm, 7 μm, and flow velocity is 2mL/min, mobile phase MeOH:H2O=45:55 finally obtains compound 2, compound 3 and compound 8.
The measurement of the anti-insect activity of 4 the compounds of this invention 1-8 of embodiment
Test method: compound 1-8 is taken to carry out active testing to cotton bollworm larvae.
Bollworm active testing is added equivalent in 6 orifice plates and is mixed with various concentration sample (200,100,50,25 and 12.5 μ The hole L/) man-made feeds, parallel three groups.Positive group, blank group and negative group are set, are separately added into positive controls corresponding Man-made feeds and positive drug (200,100,50,25and 12.5 hole μ L/), blank control are equivalent man-made feeds, negative control For the DMSO (12.5 hole μ L/ 200,100,50,25and) of various concentration.6 orifice plates are placed into continuous culture one week at room temperature, are seen The growing state for examining cotton bollworm larvae observed and recorded Growth of The Cotton Bollworm death condition every 2 days.The wooden chinaberry element It (azadirachtin) is positive control drug.
Test result is as follows:
Table 3:
In upper table: IC50: 503nhibiting concentration (half maximal inhibitory concentration).
Azadirachtin aFor positive drug.
Test result shows that 1,2,5,6,8 couple of H.armigera Hubne of compound has inhibitory activity, IC50Value difference For 200,200,200,100,100 μ g/mL, the IC of compound 3,4,750>200μg/mL。

Claims (10)

1. a kind of isocoumarin class compound or its pharmaceutically acceptable salt, it is characterised in that the isocoumarin class compound With structure shown in compound 1-8:
2. a kind of preparation method for preparing isocoumarin class compound 1-8 described in claim 1 simultaneously, it is characterised in that including Following steps:
(1) seed culture medium is prepared, TGM112 bacterial strain is accessed into seed culture medium, 26~28 DEG C, obtains seed training within culture 3~4 days Nutrient solution；
(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 and thallus use isometric second respectively Acetoacetic ester extracts 3~5 times, and medicinal extract is concentrated under reduced pressure to give after combining extraction liquid；
(4) step (3) obtains medicinal extract by decompression silica gel column chromatography, using petroleum ether-ethyl acetate by 100:0,90:10, 80:20,70:30,60:40,50:50,40:60,30:70,20:80,10:90,0:100 gradient elution, each gradient collect two A column volume, through Sephadex LH-20 gel filtration chromatography after the fraction concentration that wherein 20:80 gradient elution obtains, eluant, eluent is Methanol: chloroform=1:1, then prepared through high-efficient liquid phase chromatogram HPLC, chromatographic column is Agilent C18,9.4 × 250mm, 7 μm, stream Speed is 2mL/min, mobile phase CH3CN:H2O=45:55 finally obtains compound 1, compound 4, compound 5,6 and of compound Compound 7；Through Sephadex LH-20 gel filtration chromatography after the fraction concentration that wherein 0:100 gradient obtains, eluant, eluent is methanol: Chloroform=1:1, then prepared through high-efficient liquid phase chromatogram HPLC, chromatographic column is Agilent C18,9.4 × 250mm, 7 μm, and flow velocity is 2mL/min, mobile phase MeOH:H2O=45:55 finally obtains compound 2, compound 3 and compound 8.
3. preparation method as claimed 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. the described in any item preparation methods of claim 2-3, 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 with compound 1-8 described in claim 1 or its pharmaceutically acceptable salt As active constituent.
6. pharmaceutical composition described in claim 5, it is characterised in that also may include other insecticidal materials.
7. the described in any item pharmaceutical compositions of claim 5-6, it is characterised in that it also may include pharmaceutically acceptable auxiliary material, It is preferred that pharmaceutically acceptable carrier, diluent or excipient.
8. the described in any item pharmaceutical compositions of claim 5-7, it is characterised in that the dosage form of described pharmaceutical composition can be Solid pharmaceutical preparation, semisolid preparation or liquid preparation.
9. compound 1-8 described in claim 1 or its pharmaceutically acceptable salt are preparing the purposes in insecticide.
10. purposes as claimed in claim 9, it is characterised in that kill the purposes in bollworm drug in preparation.
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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
CN110483467A (en) * 2019-07-11 2019-11-22 宁波大学 Dihydroiso-coumarin analog derivative and its preparation method and application
CN110982700A (en) * 2019-10-29 2020-04-10 中国科学院微生物研究所 Polyketide with anti-helicobacter pylori activity and preparation method and application thereof
CN114621092A (en) * 2022-03-08 2022-06-14 海南师范大学 Phenolic compound in mangrove plant-derived fungi and preparation method thereof

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