CN113651677A - Compound eutyscoparin G, preparation method thereof and application thereof in preparation of antibacterial drugs - Google Patents

Compound eutyscoparin G, preparation method thereof and application thereof in preparation of antibacterial drugs Download PDF

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CN113651677A
CN113651677A CN202110559597.3A CN202110559597A CN113651677A CN 113651677 A CN113651677 A CN 113651677A CN 202110559597 A CN202110559597 A CN 202110559597A CN 113651677 A CN113651677 A CN 113651677A
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compound
eutyscoparin
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scbg
ethyl acetate
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CN113651677B (en
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吴杰英
张文歌
谭海波
狄金明
李腾成
霍璐琼
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South China Botanical Garden of CAS
Third Affiliated Hospital Sun Yat Sen University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
    • C07C33/14—Alcohols containing rings other than six-membered aromatic rings containing six-membered rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/22—Preparation of oxygen-containing organic compounds containing a hydroxy group aromatic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

The invention discloses a compound eutyscoparin G, a preparation method thereof and application thereof in preparing antibacterial drugs. A compound, eutyscoparins G, of formula (I): the compound, namely the teutyracopis G, is separated and prepared from endophytic fungus Eutypella scoparia SCBG-8, has relatively obvious antibacterial activity, can be used for preparing antibacterial drugs, provides candidate compounds for researching and developing new antibacterial drugs, and provides a new candidate compound for developing and benefitingThe natural active substances from plant endophytes provide scientific basis.
Figure DDA0003078535760000011

Description

Compound eutyscoparin G, preparation method thereof and application thereof in preparation of antibacterial drugs
Technical Field
The invention belongs to the technical field of medical biology, and particularly relates to a compound eutyscoparin G, a preparation method thereof and application thereof in preparation of antibacterial drugs.
Background
Eutypella fungi are widely distributed, and secondary metabolites are abundant and diverse. The main metabolites include terpenes, cytochalasin, steroids, and lactones, wherein the terpenes are mainly pimarane diterpenes and sesquiterpenes. Moreover, the secondary metabolite shows various biological activities such as antitumor, antibacterial, anti-inflammatory and antiproliferative activities. The Sesquiterpenes compounds are metabolites in fungi, and have the structural characteristics that the molecules contain three isoprene units consisting of 15 carbon atoms and have various framework structures such as chain structures, ring structures and the like. Molecules of this type have been reported to possess a variety of biological activities. We found 1 novel compound eutyscoparin G with antibacterial activity in the study of endophytic fungus SCGB-8.
The invention content is as follows:
it is a first object of the present invention to provide a compound, eutyscoparins G, having antibacterial activity.
The structure of the compound eutyscoparin G is shown as the formula (I):
Figure BDA0003078535740000011
the second purpose of the invention is to provide a preparation method of a compound, eutyscoparin G, in the preparation method, the compound, eutyscoparin G, is separated and prepared from a fermentation culture of a plant endophytic fungus, Eutypella scoparia SCBG-8, and specifically comprises the following steps:
(1) preparing solid fermentation culture of endophytic fungus Eutypella scoparia SCBG-8, extracting the solid fermentation culture with ethyl acetate, and concentrating ethyl acetate extract to obtain extract;
subjecting the extract to silica gel column chromatography, and performing gradient elution with petroleum ether-ethyl acetate at volume ratio of 100:1, 50:1, 20:1,10:1,5:1,2:1,1:1, 0:1 as eluent; collecting the product eluted by n-hexane-ethyl acetate in a volume ratio of 10:1, and performing TLC thin layer chromatography by using n-hexane: developing ethyl acetate at 5:1v/v to obtain component Fr.3 with Rf at 0.5-0.6;
subjecting the fraction Fr.3 to reverse phase column chromatography, gradient eluting with methanol-water at a volume ratio of 80:20,85:15,90:10,95:5,100:0, and acetone to obtain 6 subfractions Fr.3.1-Fr.3.6, wherein the fraction Fr.3.2 is purified on Sephadex LH-20 column chromatography to obtain 4 fractions Fr.3.2.1-Fr 3.2.4. Fr.3.2.2 was passed through a further normal phase silica gel column, purified with n-hexane: the ethyl acetate is eluted by gradient of 20:1,10:1,5:1,2:1,1:1 to obtain 5 subfractions Fr.3.2.2.1-Fr.3.2.2.5. Fr.3.2.2.3 was isolated and purified by semi-preparative HPLC to give compound eutyscoparin G.
The preparation of the solid fermentation culture of the endophytic fungus Eutypella scoparia SCBG-8 comprises the following specific steps: selecting mycelium of SCBG-8, inoculating the mycelium into a potato dextrose liquid culture medium, culturing for 5 days at the temperature of 28 ℃ and at the speed of 120r/min to prepare a seed solution, then inoculating the seed solution into a rice culture medium according to the inoculation amount of 0.1mL/g, and culturing for 30 days at the temperature of 28 ℃ to prepare a solid fermentation culture of SCBG-8, wherein each liter of the potato dextrose liquid culture medium is prepared by the following method: decocting 200g of potato in 500mL of pure water, boiling for 20min, filtering to obtain potato juice, adding glucose 20g and KH2PO4 3g、MgSO41.5g, vitamin B110mg, made up with waterSterilizing to 1000 mL; the rice culture medium is prepared by the following method: prepared by mixing and sterilizing 300g of rice and 360mL of water.
Experiments show that the compound eutyscoparin G has IC (integrated Circuit) effect on staphylococcus aureus and methicillin-resistant staphylococcus aureus50The value was 6.25. mu.g/mL. IC of positive control vancomycin against the above two gram-positive bacteria50The value was 1.25. mu.g/mL. This result shows that: the compound eutyscoparin G of the invention has relatively remarkable antibacterial activity.
Accordingly, a third object of the present invention is to provide the use of the compound eutyscoparin G, or a pharmaceutically acceptable salt thereof, for the preparation of antibacterial agents. The antibacterial drugs are preferably anti-staphylococcus aureus drugs and anti-methicillin-resistant staphylococcus aureus drugs.
Figure BDA0003078535740000031
It is a fourth object of the present invention to provide an antibacterial agent comprising the compound, deutscoparins G, or a pharmaceutically acceptable salt thereof as an active ingredient. Preferably, the antibacterial drug is an anti-staphylococcus aureus drug and an anti-methicillin-resistant staphylococcus aureus drug.
The fifth object of the present invention is to provide the use of the endophytic fungus Eutypthus scoparia SCBG-8 for the preparation of the compound, teutysprovids G.
Compared with the prior art, the invention has the advantages that:
the compound, namely the teutyspropalins G, is separated and prepared from endophytic fungi Eutypthus scoparia SCBG-8, has relatively obvious antibacterial activity, can be used for preparing antibacterial drugs, provides candidate compounds for researching and developing new antibacterial drugs, and provides scientific basis for developing and utilizing natural active substances from plant endophytic bacteria.
The fungus Eutypella scoparia SCBG-8 of the present invention has been disclosed in Wenge Zhang, Miaomiao Wang, Sha ZHa, Kangping Xu, Guishan Tan, Shengxiang Qiu, Zhenxing Zou, Haibo Tan Eutypopanols A-G, polyketide derivatives from endenoptic funguses Eutypella scoparia SCBG-8, Fitoterapia,2020, 146,104681.
Drawings
FIG. 1 is a schematic representation of the compound deutyscoparins G1H NMR spectrum;
FIG. 2 is a schematic representation of the compound deutyscoparins G13C NMR spectrum;
FIG. 3 is a schematic representation of the compound deutyscoparins G1H-1H COSY spectrum;
FIG. 4 is the HSQC spectra of compound deutyscoparins G;
FIG. 5 is an HMBC spectrum of compound deutyscoparins G;
FIG. 6 is a NOESY spectrum of the compound, teutyscaprins G;
FIG. 7 is an HRESIMS spectrum of compound deutyscoparins G;
FIG. 8 is a UV spectrum of compound deutyscoparins G;
FIG. 9 is a CD spectrum of compound deutyscoparins G;
FIG. 10 is an IR spectrum of the compound deutyscoparins G;
Detailed Description
The following examples are further illustrative of the present invention and are not intended to be limiting thereof.
Example 1
1. Isolation, purification and characterization of the endophytic fungus Eutypella scoparia SCBG-8
The endophytic fungus Eutypella scoparia SCBG-8 of the invention is separated from leaves of Melittleria excelsa (Leptospermum brachyanum) in the Australian plant park (SCBG) of the Chinese academy of sciences at 2016 (9 months), is further identified by ITS sequence analysis, has a GenBank accession number of MN788605, and belongs to Eutypella genus fungus through blast comparison and homology analysis, and is named as Eutypella scoparia SCBG-8.
2. Solid fermentation of Eutypella scoparia SCBG-8
Culturing activated mycelium of Eutypella scoparia SCBG-8Inoculating the liquid to potato glucose liquid culture medium (each liter of culture medium is prepared by decocting 200g potato in 500mL pure water, boiling for 20min, filtering to obtain potato juice, and adding glucose 20g and KH2PO4 3g、MgSO41.5g, vitamin B110mg, made by supplementing to 1000mL with water and sterilizing), cultured at 28 ℃ for 5 days at 120r/min to prepare a seed liquid, and then inoculated into a rice medium in an amount of 0.1mL/g (prepared by the following method: mixing rice 300g with water 360mL, sterilizing, mixing, autoclaving at 121 deg.C for 20min, and cooling) and culturing at 28 deg.C for 30 days to obtain solid fermentation culture of SCBG.
3. Preparation of compound deutyscoparins G
(1) Adding ethyl acetate into the solid fermentation culture of SCBG, soaking and extracting for 24 hr, repeating the extraction for 3 times, mixing the extractive solutions, and concentrating to obtain extract (45 g).
Subjecting the extract to silica gel column chromatography, and performing gradient elution with petroleum ether-ethyl acetate at volume ratio of 100:1, 50:1, 20:1,10:1,5:1,2:1,1:1, 0:1 as eluent; collecting the product eluted by n-hexane-ethyl acetate in a volume ratio of 10:1, and performing TLC thin layer chromatography by using n-hexane: developing ethyl acetate at 5:1v/v to obtain component Fr.3 with Rf at 0.5-0.6;
subjecting the fraction Fr.3 to reverse phase column chromatography, gradient eluting with methanol-water at a volume ratio of 80:20,85:15,90:10,95:5,100:0, and acetone to obtain 6 subfractions Fr.3.1-Fr.3.6 sequentially, wherein the fraction Fr.3.2 is purified on Sephadex LH-20 column chromatography to obtain 4 fractions Fr.3.2.1-Fr 3.2.4. Fr.3.2.2 (polarity: Rf value 0.2-0.8 by TLC chromatography on a chromatographic support with n-hexane: acetone 5/1v/v chromatography, dark blue coloration with vanillin in the presence of uv light) is passed through a further normal phase silica gel column, purified with n-hexane: ethyl acetate 20:1,10:1,5:1,2:1,1:1v/v gradient elution order gave 5 subfractions Fr.3.2.2.1-Fr.3.2.2.5. Fr.3.2.2.3 using semi-preparative HPLC with column parameters of YMC-Pack ODS-A, elution conditions of volume fraction of 85% methanol water, flow rate of 2ml/min, and collection of 34min retention time fraction to obtain compound eutyscoparin G.
4. Structure identification of compound eutyscoparin G
1H-NMR、13C-NMR and HMBC nuclear magnetic resonance spectrograms are measured by a Bruker advanced-600 nuclear magnetic resonance spectrometer, and Tetramethylsilane (TMS) is taken as an internal standard; ESI-MS data were measured with VG Autospec-3000 type mass spectrometer; the ultraviolet spectrum is measured by an Shimadzu UV-2600 spectrophotometer, and the structure identification is as follows:
as shown in FIGS. 1 to 10, FIG. 1 is a schematic representation of the compound eutyscoparin G1H NMR spectrum; FIG. 2 is a schematic representation of the compound eutyscoparin G13C NMR spectrum; FIG. 3 is a schematic representation of the compound eutyscoparin G1H-1H COSY spectrum; FIG. 4 is an HSQC spectrum of compound eutyscoparin G; FIG. 5 is an HMBC spectrum of compound eutyscoparin G; FIG. 6 is a NOESY spectrum of compound eutyscoparin G; FIG. 7 is an HRESIMS spectrum of compound eutyscoparin G; FIG. 8 is a UV spectrum of compound eutyscoparin G; FIG. 9 is a CD spectrum of compound eutyscoparin G; FIG. 10 is an IR spectrum of compound eutyscoparin G;
compound 1 was a yellow powder (nuclear magnetic data shown in table 1); according to HRESIMS [ M + H ]]+m/z 223.2054， C15H27O, calculated as 223.2056, and the molecular formula of the compound determined as C15H26O, unsaturation is 3;1the H-NMR spectrum showed an olefin proton signal [ delta ]H 5.31(s,H-3)](ii) a 3 methyl signals [ delta ]H 0.93(d,J＝6.9Hz,H3-13),1.6 (s,H3-14),0.77(s,H3-15)]。13The C-NMR spectrum and the HSQC spectrum showed 15 carbon signals in Compound 1, including 2 quaternary carbons (including 1 alkenyl carbon), 4 methines, 6 methylenes, and 3 methyl groups. The planar structure of the compound eutyscoparin G is determined by further analyzing two-dimensional spectrograms such as COSY, HSQC, HMBC and the like, and the absolute configuration of the compound I is determined by calculating an ECD method.
The structural formula of the target compound eutyscoparin G separated by the method is shown as the formula (I):
Figure BDA0003078535740000071
TABLE 1 Nuclear magnetic data for Compound 1 (500MHz/125MHz, Δ in ppm, J in Hz)
Figure BDA0003078535740000072
Example 2
The antibacterial activity of compound eutyscoparin G was tested by MHB (Microbroth dilution in Mueller-Hinton broth) method.
1. Test reagents: the compound eutyscoparin G prepared by the invention is dissolved in dimethyl sulfoxide (DMSO) to obtain a mother solution with the concentration of 1mg/mL, and then the mother solution is subjected to gradient dilution by using a 96-well plate. The positive control was vancomycin.
The strains used in this experiment were s.aureus (26003) and MRSA (JCSC 3063).
2. The experimental method comprises the following steps: the compounds were evaluated for their antibacterial activity according to the CLSI guidelines by determining the MIC values using the MHB (Microbroth in Mueller-Hinton broth) method and using Resazurin as a visual indicator. Fresh HB medium was diluted to OD using a UV-6000 spectrophotometer using S.aureus (26003) and MRSA (JCSC 3063) bacteria at logarithmic growth phase600Mixing the above bacterial suspension and resazurin at a volume ratio of 6:9, inoculating into 96-well plate, adding 180. mu.L of bacterial suspension and 20. mu.L of 1mg/mL compound eutyscoparin G mother liquor into each well, setting 2 blank well controls and 2 positive controls, diluting with gradient at 37 deg.C and 5% CO, and mixing2Culturing in an incubator, and observing color change after 16-20 h. Each experiment was repeated 3 times and its MIC value was calculated.
3. The experimental results are as follows: the MIC value of the compound eutyscoparin G prepared by the invention to gram-positive bacteria S.aureus (26003) and MRSA (JCSC 3063) is 6.25 mu G/mL. The MIC value for the positive control vancomycin for S.aureus (26003) and MRSA (JCSC 3063) was 1.25. mu.g/mL. This result shows that: the compound eutyscoparin G has relatively obvious antibacterial activity, so that the compound provided by the invention provides a candidate compound for researching and developing a new antibacterial drug, and provides a scientific basis for developing and utilizing natural active substances from plant endophytes.
The above is only a preferred embodiment of the present invention, and it should be noted that the above preferred embodiment should not be considered as limiting the present invention, and the protection scope of the present invention should be subject to the scope defined by the claims. It will be apparent to those skilled in the art that various modifications and adaptations can be made without departing from the spirit and scope of the invention, and these modifications and adaptations should be considered within the scope of the invention.
The invention discloses a compound eutyscoparin G, a preparation method thereof and application thereof in preparing antibacterial drugs. The compound eutyscoparin G is prepared by separating and preparing fermentation culture of endophytic fungus Eutypella scoparia SCBG-8. Experiments prove that the MIC value of the compound eutyscoparin G on gram-positive bacteria S.aureus (26003) and MRSA (JCSC 3063) is 6.25 mu G/Ml, the compound eutyscoparin G shows remarkable antibacterial activity and can be used for preparing antibacterial drugs.

Claims (9)

1. A compound, eutyscoparins G, of formula (I):
Figure FDA0003078535730000011
2. a process for the preparation of the compound eutyscoparin G according to claim 1, wherein the compound eutyscoparin G is isolated from the fermentation culture of the endophytic fungus Eutypella scoparia SCBG-8.
3. The preparation method according to claim 2, characterized by comprising the following steps:
(1) preparing solid fermentation culture of endophytic fungus Eutypella scoparia SCBG-8, extracting the solid fermentation culture with ethyl acetate, and concentrating ethyl acetate extract to obtain extract;
(2) subjecting the extract to silica gel column chromatography, and performing gradient elution with petroleum ether-ethyl acetate at volume ratio of 100:1, 50:1, 20:1,10:1,5:1,2:1,1:1, 0:1 as eluent; collecting the product eluted by n-hexane-ethyl acetate in a volume ratio of 10:1, and performing TLC thin layer chromatography by using n-hexane: developing ethyl acetate at 5:1v/v to obtain component Fr.3 with Rf at 0.5-0.6;
subjecting the fraction Fr.3 to reverse phase column chromatography, gradient eluting with methanol-water at a volume ratio of 80:20,85:15,90:10,95:5,100:0, and acetone to obtain 6 subfractions Fr.3.1-Fr.3.6, wherein the fraction Fr.3.2 is purified on Sephadex LH-20 column chromatography to obtain 4 fractions Fr.3.2.1-Fr 3.2.4. Fr.3.2.2 was passed through a further normal phase silica gel column, purified with n-hexane: the ethyl acetate is eluted by gradient of 20:1,10:1,5:1,2:1,1:1 to obtain 5 subfractions Fr.3.2.2.1-Fr.3.2.2.5. Fr.3.2.2.3 was isolated and purified by semi-preparative HPLC to give compound eutyscoparin G.
4. The preparation method according to claim 3, wherein the separation and purification of component Fr.3.2.2.3 by HPLC specifically comprises: subjecting fraction Fr.3.2.2.3 to semi-preparative HPLC using YMC-ODS-A/AQ column with A mobile phase of methanol/water at A volume ratio of 85:15 and A flow rate of 3mL/min, and collecting eluate fraction with retention time of 34min to obtain compound eutyscoparin G.
5. The method according to claim 3, wherein the step (1) of preparing the solid fermentation culture of the endophytic fungus Eutypthus scoparia SCBG-8 comprises the following steps: selecting mycelium of SCBG-8, inoculating the mycelium into a potato dextrose liquid culture medium, culturing for 5 days at the temperature of 28 ℃ and at the speed of 120r/min to prepare a seed solution, then inoculating the seed solution into a rice culture medium according to the inoculation amount of 0.1mL/g, and culturing for 30 days at the temperature of 28 ℃ to prepare a solid fermentation culture of SCBG-8, wherein each liter of the potato dextrose liquid culture medium is prepared by the following method: boiling 200g of potato in 500mL of pure water for 20min, filtering to obtain potato juice, and adding glucose 20g and KH2PO4 3g、MgSO41.5g, vitamin B110mg, supplementing water to 1000mL, and sterilizing; the rice culture medium is prepared by the following method: mixing rice 300g with water 360mLAnd (5) preparing the strain.
6. Use of the compound eutyscoparin G or its pharmaceutically acceptable salt according to claim 1 for the preparation of antibacterial agents.
7. The use of claim 6, wherein the antibacterial agent is an anti-Staphylococcus aureus, methicillin-resistant Staphylococcus aureus drug.
8. An antibacterial agent characterized by comprising a compound eutyscoparin G or a pharmaceutically acceptable salt thereof as an active ingredient.
9. Use of the endophytic fungus Eutypella scoparia SCBG-8 for the preparation of eutyscoparins G.
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