CN113527247B - Azophilone polymer compound and preparation method and application thereof - Google Patents
Azophilone polymer compound and preparation method and application thereof Download PDFInfo
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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
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- 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
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/14—Fungi; Culture media therefor
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- 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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- 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
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
Abstract
The invention provides a diazotrophone polymer compound and a preparation method and application thereof. The invention carries out fermentation culture on the muyocopropron latex, and separates the fermentation product to obtain the high-purity compound monomer, wherein the compound has a novel structural framework and the structure is
Description
Technical Field
The invention relates to the technical field of pharmaceutical chemistry, in particular to a polymer compound of a diazotrophone class, a preparation method and an application thereof.
Background
Weeds are primarily plants, generally herbaceous plants, which are unfavorable for human activities or harmful to crop growth. Weeds compete with crops for nutrients, moisture, light and space, and spread pests, thereby reducing the yield and quality of crops. The weed control means mainly comprises physical weeding, chemical weeding, biological weeding and the like, wherein the chemical weeding is the mainstream means for preventing and killing weeds at present due to the characteristics of high efficiency, timeliness, labor saving, economy and the like.
Classified by mode of action, herbicides can be classified as selective herbicides (harmful to a portion of weeds) and non-selective herbicides (toxic to all plants, such as glyphosate). The herbicides are classified into inorganic herbicides and organic herbicides (ethers, sym-trinitrobenzenes, substituted ureas, phenoxyacetic acids, pyridines, dinitroanilines, organophosphates, amides, phenols, etc.) according to chemical composition. Herbicides are classified into photosynthesis inhibitors, amino acid biosynthesis inhibitors, fatty acid biosynthesis inhibitors, cell division inhibitors, and the like, according to the mechanism of action. Many herbicides have proved to have good weed control effect through practice, however, with the long-term use of chemical herbicides in large quantities, the problem of drug resistance of weeds is increasingly serious, so that the development of novel efficient herbicides is urgently needed.
Azotones are a class of compounds found in fungi that contain a highly oxidized pyranone benzoquinone bicyclic ring and a chiral quaternary carbon center. Researches show that the azone compound has wide biological activity including cytotoxicity, antitumor activity, antibacterial activity and the like. At present, the structure and activity of the azone compound have been studied to a certain extent, but a large number of novel structures are not found, and the research of the azone compound on the aspect of weed control is not reported.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a diazotrophone polymer compound and a preparation method and application thereof.
The technical scheme of the invention mainly comprises the following contents:
a polymeric compound of the azophilic ketone has a structural formula shown as the following formula I:
the preparation method of the azone polymer compound comprises the following steps:
(1) Inoculating fungus muyocopropron laterale into a culture medium, fermenting and culturing to obtain a fermentation product, ultrasonically extracting the fermentation product by using ethyl acetate, and concentrating under reduced pressure to dry to obtain a total extract;
(2) Dissolving the total extract by using methanol, carrying out silica gel column chromatography, detecting and combining an elution system by TLC (thin layer chromatography) with a dichloromethane-methanol solution with a volume ratio of 100-1;
(3) Separating the fraction Fr.B by Sephadex column chromatography, isocratic eluting with methanol, separating the obtained fraction by semi-preparative liquid chromatograph with methanol-water as mobile phase to obtain the polymer compound of claim 1.
The fungus muyocopron latex can be isolated from plants such as blumea balsamifera by conventional methods, or can be obtained from a corresponding depository. Known strains of the muyocopropron latex include CBS 719.95, CBS 145311, CBS 145312, CBS 145316 of the Netherlands Collection of microorganisms (Central microbial culture Institute), IMI 324533 of the International Genetic Resource Collection of International society of agricultural and biological research, england.
Preferably, in the step (3), the volume ratio of methanol to water is 70.
Preferably, the chromatographic column of the semi-preparative liquid chromatography is: YMC-Pack ODS-A.
Preferably, the culture medium is prepared by adding 80mL of water to 60g of rice.
Preferably, the fraction fr.b is a fraction eluted with dichloromethane-methanol in a volume ratio of 99.
Preferably, the fermentation culture conditions are: and (3) carrying out static culture at 28 ℃ for 30d.
Preferably, the Sephadex LH-20 chromatographic column is Sephadex LH-20.
On the other hand, the invention also provides the application of the azophiline polymer compound in weed control. More specifically, the azophiline polymer compound can achieve weed control effect by inhibiting the growth of plant roots.
The invention has the following effects:
(1) The invention separates a diazotrophone polymer compound from a fermentation product of endophytic fungus muyocopron laterale, and the diazotrophone compound has a novel structural framework and belongs to a novel diazotrophone compound.
(2) The invention carries out fermentation culture on the muyocopropron laterale, and separates the fermentation product to obtain the high-purity compound monomer. The preparation method provided by the invention is simple and efficient.
(3) The research of the invention finds that the obtained compound has strong effect of inhibiting the elongation of plant roots and can be used as a new generation of herbicide active ingredient.
Drawings
FIG. 1: 1H NMR Spectrum of Compound 1
FIG. 2: 13C NMR Spectrum of Compound 1
FIG. 3: HSQC spectrum of compound 1
FIG. 4: HMBC spectrum of Compound 1
FIG. 5 is a schematic view of: HRESIMS spectrum of Compound 1
FIG. 6: EXAMPLE 3 results chart
Detailed Description
In order to better understand the technical content of the invention, specific examples are provided below to further illustrate the invention.
Instruments and reagents:
nuclear magnetic resonance spectrometer (bruker avance 500 MHz);
mass spectrometer (Waters Synapt G2, USA);
waters 2489 semi-preparative liquid chromatography systems (Waters Corporation, milford, MA, USA);
se:Sup>A semi-preparative chromatographic column YMC-Pack ODS-A (5 μm,250mm10 mm, beijing Huideyi scientific and technological Limited liability Co., ltd.);
200-300 mesh column chromatography silica gel and GF 254 thin layer silica gel plate (Qingdao ocean factory);
PDA: 200g of potato, 20g of glucose, 15g of agar and 1000mL of water are sterilized for 20min at 121 ℃.
Example 1 extraction of Azalone-like multimeric Compound
(1) Collecting blumea balsamifera root, washing with tap water, cutting into segments, cleaning with ultra-clean bench, sterilizing with 70% ethanol for 1min, treating with 3M sodium hypochlorite for 3min, sterilizing with 70% ethanol for 30s, washing with sterile water, placing on water agar culture medium (15 g agar, 1000mL water, 100mg streptomycin, 121 deg.C high pressure steam sterilizing for 20min, and pouring onto ultra-clean bench) in an incubator at 25 deg.C for 2 weeks, picking out hypha with cross section, and inoculating to PDA culture medium. The fungus is identified as a muyocopron latex belonging to an ascomycete (ascomycete) of the family myxomycetaceae.
(2) The fungus muyocopropron laterale is inoculated on a sterile PDA plate medium with the diameter of 6cm, cultured for 5 days at 28 ℃ until colonies are distributed on the whole medium plate, and the tissue blocks with the diameter of about 0.5cm multiplied by 0.5cm are cut under the sterile condition for standby. Adding 60g rice and 80mL water into 500mL triangular flask, wrapping with tinfoil paper, sterilizing with high pressure steam at 121 deg.C for 20min, taking out, and standing at room temperature. Inoculating the culture medium block with bacteria into a rice culture medium under an aseptic condition, wherein 2-3 blocks are inoculated into each bottle, standing and culturing at 28 ℃ for 30d, and stopping fermentation by ethyl acetate.
(2) Ultrasonically extracting rice fermentation product of fungus muyocopropron laterale with ethyl acetate for 3 times, 30 min/time, and concentrating under reduced pressure to dry to obtain 20.3g of secondary metabolite total extract. Dissolving the total extract with methanol, mixing with silica gel at a ratio of 1/3, performing silica gel column chromatography, and sequentially eluting with dichloromethane-methanol (100/0, 99/1, \8230; 1/1, V/V) to obtain 8 fractions A (100/0), B (100/0), C (99/1), D (99/1), E (98/2), F (20/1), G (10/1), and H (1/1). TLC detection was combined to give 7 fractions fr.a-fr.g. Fr.b (6.2 g, dichloromethane: methanol = 99) was chromatographed on a Sephadex LH-20 column, eluting with methanol, to give 2 fractions in total, of which the 2 nd fraction (RO-B-2, 90 mg) was separated by semi-preparative liquid chromatography using methanol-water (70, 30, v/v) as the mobile phase to isolate compound 1 (22.1mg, tr =11.2min, flow rate 2 mL/min).
Example 2: structural characterization of Compound 1
The structure of compound 1 is analyzed by structure identification techniques such as spectroscopy and spectroscopy.
Structural analysis of the compound:
orange color powder, HR-ESI-MS gives the ionic peak m/z 565.2069M + H] + ,587.1885[M+Na] + The calculated values are 565.2066,587.1885, and the molecular formula is determined to be C 31 H 32 O 10 。 13 The C NMR spectrum showed 31 carbon signals (including 4 overlapping high field signals), combined 1 The HNMR and HSQC spectra showed that the structure contained 6 methyl groups, 2 methylene groups, 6 methine groups, 17 quaternary carbons (including 4 carbonyl carbons,δ C 206.2,205.9,198.3, 197.7) in HMBC spectra, H-1 (. Delta.) (delta.)) H 7.45 Are with C-3 (. Delta.) C 160.7),C-4a(δ C 143.7),C-8a(δ C 120.8),C-8(δ C 71.7 Correlation, H-4 (. Delta.) H 6.39 Is with C-9 (. Delta.) C 18.5),C-3(δ C 160.7),C-4a(143.7),C-5(δ C 109.3),C-8a(δ C 120.8 Correlation of H-8 (. Delta.) H 4.46 Delta. With C-1 C 144.9),C-6(δ C 197.7),C-7(δ C 76.4 C-4a and C-8a are related, and the detection of carbon signals of middle and low fields shows that the carbon signals are all in pairs, in total, 11 pairs, the above analysis showed that two symmetric fragments of azaphilone structure may be present in the structure. HMBC spectroscopic analysis showed H-17 (. Delta.) ( H 1.88 Is with C-12 (. Delta.) C 155.5),C-13(δ C 154.3),C-14(δ C 206.2 Correlation, H-18 (. Delta.) H 1.11 Is with C-15 (. Delta.) C 49.8),C-14(δ C 206.2),C-16(δ C 205.9 C-11' (delta) C 30.2 Related) suggests the presence of a five-membered alpha, beta unsaturated cyclic diketone. Further HMBC correlation analysis, H-11 (. Delta.) H 3.41 In relation to C-12, C-13, C-16, C-4a, C-5, C-6, suggesting that the C-12 position of the five-membered ring passes through one CH 2 Is linked to the C-5 position of one of the Azaphilone fragments. H-11' (delta) in HMBC correlation spectra H 2.68, 2.49) and C-14, C-15, C-16, C-18 (. Delta.) (B) C 17.3),C-4’a(δ C 144.5),C-5’(δ C 109.1),C-6’(δ C 198.3 Related, showing the C-15 position of the five-membered ring through another CH 2 Is linked to the C-5' position of another azaphilone fragment.
The chemical structure of the compound 1 obtained was analytically determined as follows:
example 3: root elongation inhibition experiment
Sterilizing seeds of Arabidopsis thaliana belonging to the genus Arabidopsis of the family Brassicaceae with 5% sodium hypochlorite solution, washing with sterile water, and wiping off water. Preparing a mother solution of compound 1 obtained in example 1 with dimethyl sulfoxide (DMSO) to a final concentration of 40mg/mL for later use; the mother solution was aspirated and added to 25mL of 1/2MS medium so that the concentration of Compound 1 was 8. Mu.g/mL, 16. Mu.g/mL, and 32. Mu.g/mL, respectively, to prepare treatment groups. A blank control was prepared by adding 20. Mu.L of DMSO. 5 seeds with consistent growth potential are uniformly added on each plate, and 3 parallel experiments are set in each group. Each group of plates was incubated in a constant temperature (23. + -. 1 ℃) culture chamber with a photoperiod L/D of 18h/6h. After 9 days, the growth of the root system of each group was observed. The results are shown in FIG. 6.
The results show that: the compound 1 has obvious inhibition effect on the elongation of arabidopsis thaliana seed root system under the concentration of 8-32 mug/mL, wherein the average inhibition rate of the concentration of 32 mug/mL reaches more than 90%.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that are within the spirit and principle of the present invention are intended to be included in the scope of the present invention.
Claims (4)
1. A polymeric compound of the azophilic ketone, which is characterized in that the structural formula is shown as the following formula I:
I
2. the method for producing the Azalone-based multimeric compound according to claim 1, comprising the steps of:
(1) Fungus is cultured in a culture mediummuyocopron laterale Inoculating into culture medium, standing at 28 deg.C, fermenting for 30d to obtain fermented product, ultrasonically extracting with ethyl acetate, and concentrating under reduced pressure to dry to obtain total extract;
wherein the culture medium is prepared by adding 80mL of water into every 60g of rice and mixing;
(2) Dissolving the total extract with methanol, performing silica gel column chromatography, and detecting and combining by TLC (thin layer chromatography) an elution system which is dichloromethane-methanol solution with a volume ratio of 100 to 1, so as to obtain 7 fractions Fr.A-Fr.G;
wherein fraction fr. B is a fraction eluted with dichloromethane-methanol in a volume ratio of 99;
(3) Separating the fraction Fr and B by Sephadex LH-20 column chromatography, isocratically eluting with methanol, separating the obtained fraction by semi-preparative liquid chromatograph with methanol-water as mobile phase at volume ratio of 70;
wherein, the chromatographic column of the semi-preparative liquid chromatography is as follows: YMC-Pack ODS-A.
3. The use of the azophilic ketone polymer compound as claimed in claim 1 for controlling weeds.
4. The use of the polymeric azone compound as claimed in claim 1 for inhibiting the growth of plant roots.
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| PCT/CN2021/137672 WO2023019821A1 (en) | 2021-08-18 | 2021-12-14 | Azaphilone polymer compound, and preparation method therefor and use thereof |
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| CN102453015B (en) * | 2010-10-15 | 2013-11-20 | 中国科学院海洋研究所 | Azaphilone derivatives, preparation method, and application thereof |
| US20130197071A1 (en) * | 2012-01-27 | 2013-08-01 | University Of Southern California | Production of lipoxygenase inhibitors via fungal biosynthetic pathway |
| CN104892622B (en) * | 2015-06-05 | 2017-08-29 | 华北制药集团新药研究开发有限责任公司 | Thermophilic nitrogen ketone compounds and its production and use |
| CN110407847B (en) * | 2018-04-28 | 2021-07-13 | 中国科学院青岛生物能源与过程研究所 | Azaphilones compounds obtained from aspergillus terreus and preparation and application thereof |
| CN111153908B (en) * | 2020-02-02 | 2021-04-27 | 自然资源部第三海洋研究所 | Azophilic ketone alkaloid with anti-tumor activity, preparation method and application thereof |
| CN111411045B (en) * | 2020-03-27 | 2022-10-04 | 河北大学 | Marine fungus-derived azaphilones dimer compound and preparation method thereof |
| CN113527247B (en) * | 2021-08-18 | 2023-02-03 | 中国热带农业科学院热带作物品种资源研究所 | Azophilone polymer compound and preparation method and application thereof |
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| CN109706086A (en) * | 2019-01-18 | 2019-05-03 | 河北大学 | A kind of marine fungi source azaphilones class compound and its preparation method and application |
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