CN114920649B - 18-hydroxyoleic acid diphenyl ether ester and preparation method and application thereof - Google Patents
18-hydroxyoleic acid diphenyl ether ester and preparation method and application thereof Download PDFInfo
- Publication number
- CN114920649B CN114920649B CN202110148267.5A CN202110148267A CN114920649B CN 114920649 B CN114920649 B CN 114920649B CN 202110148267 A CN202110148267 A CN 202110148267A CN 114920649 B CN114920649 B CN 114920649B
- Authority
- CN
- China
- Prior art keywords
- diphenyl ether
- percent
- preparation
- strain
- escherichia coli
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- 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
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pest Control & Pesticides (AREA)
- General Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Genetics & Genomics (AREA)
- Environmental Sciences (AREA)
- Microbiology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Dentistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Plant Pathology (AREA)
- Biotechnology (AREA)
- Oncology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses 18-hydroxyoleic acid diphenyl ether ester and a preparation method and application thereof. The molecular formula of the 18-hydroxy oleic acid diphenyl ether ester is C 36 H 52 O 9 The structural formula is shown as formula I, and the preparation method comprises the following steps: (1) Culturing strain of Phoma sp L28 in strain culture medium; (2) And (2) carrying out fermentation culture on the strain obtained in the step (1) in a fermentation culture medium, then extracting with an organic solvent, and concentrating under reduced pressure to obtain the 18-hydroxy oleic acid diphenyl ether ester. The 18-hydroxyoleic acid diphenyl ether ester has a strong inhibiting effect on banana anthracnose bacteria and tomato fusarium oxysporum, and can inhibit O78 serotype chicken escherichia coli, so that the 18-hydroxyoleic acid diphenyl ether ester can be used as a microbial agricultural bactericide or a veterinary preparation.
Description
Technical Field
The invention belongs to the field of biochemical engineering, and particularly relates to 18-hydroxyoleic acid diphenyl ether ester, and a preparation method and application thereof.
Background
The metabolites of terrestrial microorganisms are one of the important sources of antibiotics, however, in recent years, the repeated discovery problem of antibiotics in terrestrial microorganisms is more and more serious, and meanwhile, the drug resistance of pathogenic bacteria to the existing antibiotics is also aggravated, so that new research objects are urgently needed to be selected, and new research methods are tried to obtain more antibacterial substances with new structures, so that the research on new agricultural antibiotics with independent intellectual property rights is accelerated.
At present, a strategy of adding exogenous chemical substances into a culture medium to induce a new microbial metabolism product is a hot point of research at home and abroad, but the discovery of a new antibacterial active substance by utilizing the influence effect of host ingredients of marine mangrove plants on the metabolism of endophytes is rarely seen, and the antibacterial natural products of 18-hydroxyoleate containing diphenyl ether units are not reported in documents.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide 18-hydroxyoleic acid diphenyl ether ester.
The invention also aims to provide a preparation method of the diphenyl ether 18-hydroxyoleate.
The invention further aims to provide application of the diphenyl ether 18-hydroxyoleate.
The purpose of the invention is realized by the following technical scheme:
18-hydroxy oleic acid diphenyl ether ester with molecular formula of C 36 H 52 O 9 The structural formula is shown as formula I:
the diphenyl ether 18-hydroxyoleate is a colorless oil and is not reported in other documents, and the name of the diphenyl ether 18-hydroxyoleate is Phomappeher G, and the name of the diphenyl ether is 3,2' -dihydroxy-5-methyl-4 ' -methoxy-6 ' - (cis-18-hydroxy-9-octadecenoyloxymethyl) diphenyl ether-2-ethyl formate.
The preparation method of the 18-hydroxyoleic acid diphenyl ether ester (Phomaspether G) comprises the following steps:
(1) Culturing strain of Phoma sp.L28 in strain culture medium;
(2) And (2) carrying out fermentation culture on the strain obtained in the step (1) in a fermentation culture medium, then extracting with an organic solvent, and concentrating under reduced pressure to obtain the 18-hydroxy oleic acid diphenyl ether ester.
Phoma sp.L28 described in step (1) is disclosed in the literature "Song Huang, jianxin Xu, fenqi Li, danli Zhou, li Xu, chunyuan Li, identification and antibacterial Activity of microorganisms from the Man grove Fungus sp.L28, chemistry of Natural Compounds,2017,53 (2): 237-240".
Preferably, the strain culture medium in the step (1) comprises the following components in percentage by weight: 1.0 to 3.5 percent of glucose, 0.01 to 2.0 percent of yeast extract, 0.01 to 2.0 percent of peptone, 2.0 to 3.0 percent of agar, 0.2 to 2.5 percent of sodium chloride and the balance of water; when in use, the strain culture medium is made into a test tube slant.
More preferably, the strain culture medium in step (1) contains the following components in percentage by weight: 1.0 to 3.0 percent of glucose, 0.01 to 1.5 percent of yeast extract, 0.01 to 1.5 percent of peptone, 2.0 to 2.5 percent of agar, 0.2 to 2.0 percent of sodium chloride and the balance of water.
Preferably, the conditions for culturing the strain in step (1) are as follows: culturing at 20-35 deg.c for 5-10 days.
More preferably, the culture conditions of the strain in step (1) are as follows: culturing at 20-28 deg.c for 5-10 days.
Preferably, the fermentation medium in step (2) contains the following components in percentage by weight: guaiol (guaiol) 0.0001-0.00035%, japonica rice 40-60%, and water in balance.
More preferably, the fermentation medium in step (2) contains the following components in percentage by weight: guaiol (guaiol) 0.0001-0.00035%, japonica rice 40-50%, and water in balance.
Preferably, the guaiol is commercially available or can be isolated from the strain host plant, the plant, ixeris amara.
Preferably, the conditions of the fermentation culture in step (2) are as follows: culturing at 20-30 deg.c for 25-60 days.
More preferably, the conditions of the fermentation culture in step (2) are: culturing at 20-30 deg.c for 30-60 days.
Preferably, the organic solvent in step (2) is one of ethyl acetate and dichloromethane.
More preferably, the organic solvent in step (2) is ethyl acetate.
Preferably, the number of extractions in step (2) is 3 to 6.
The preparation method of the diphenyl ether 18-hydroxyoleate further comprises the step of further purifying the concentrate obtained by concentrating under reduced pressure by column chromatography and/or High Performance Liquid Chromatography (HPLC) after the step (2).
Preferably, the column chromatography is silica gel column chromatography and/or Sephadex LH-20 gel column chromatography.
Preferably, the silica gel column chromatography is performed in 200-300 mesh silica gel column chromatography.
Preferably, the silica gel column chromatography adopts petroleum ether-ethyl acetate mixed solvent as eluent for gradient elution; the volume percent of ethyl acetate was increased stepwise from 0 to 25% and the 25% ethyl acetate eluate was combined.
Preferably, the Sephadex LH-20 gel column chromatography adopts methanol as a mobile phase.
Preferably, the conditions of the High Performance Liquid Chromatography (HPLC) are as follows: the column was chromatographed using a 5 μm size C18 packing with methanol/water (MeOH/H) 2 O) is a mobile phase, the volume ratio of methanol/water is increased from 80 to 20 to 100 within 0min, and the flow rate is 3.0mL/min; 15-30 min, the volume ratio of methanol/water is 100.
The 18-hydroxy-oleic acid diphenyl ether ester is applied to preparation of a plant pathogenic bacterium agricultural bactericide and/or an avian pathogenic Escherichia coli (Escherichia coli) antibacterial agent.
Preferably, the phytopathogen is banana anthracnose (Colletotrichum musae) and/or tomato Fusarium oxysporum (Fusarium oxysporum).
Preferably, the plant pathogenic bacteria agricultural bactericide can be added with various auxiliary agents to prepare spray or powder to be used as microorganism (plant pathogenic bacteria) agricultural bactericide.
Preferably, the auxiliary agent comprises various solvents.
Preferably, the avian pathogenic escherichia coli is chicken pathogenic escherichia coli.
More preferably, the avian pathogenic escherichia coli is chicken escherichia coli serotype O78.
Preferably, the avian pathogenic escherichia coli antibacterial agent can be added with various auxiliary agents to be prepared into solution, spray or powder and the like to be used as the avian pathogenic escherichia coli antibacterial agent.
More preferably, the avian pathogenic escherichia coli antibacterial agent can be prepared into an aqueous solution, or can be prepared into a mixed aqueous solution after being mixed with various salt (such as sodium chloride and the like) solutions, and the mixed aqueous solution is fed and/or injected for preventing (preventing or treating) avian colibacillosis; or further mixing the water solution or mixed water solution of various salts with feed, and feeding for preventing and treating avian colibacillosis.
Compared with the prior art, the invention has the following advantages and effects:
the 18-hydroxy oleic acid diphenyl ether ester (Phomaspether G) prepared by the invention has stronger effect of inhibiting banana anthracnose bacteria (Colletotrichum musae) and tomato Fusarium oxysporum (Fusarium oxysporum), also has medium-strength effect of inhibiting O78 serotype chicken Escherichia coli (Escherichia coli), can be used as a related microbial agricultural bactericide or veterinary drug preparation, can be produced in a large scale, and has wide application prospect.
Detailed Description
The present invention will be described in further detail with reference to examples, but the embodiments of the present invention are not limited thereto. The reagents, methods and apparatus employed in the present invention are conventional in the art, except as otherwise indicated. The test methods in the following examples, in which specific experimental conditions are not specified, are generally performed according to conventional experimental conditions or according to the experimental conditions recommended by the manufacturer. Unless otherwise specified, reagents and starting materials for use in the present invention are commercially available.
Phoma sp.L28, which is involved in the present invention, is disclosed in the literature "Song Huang, jianxin Xu, fenqi Li, danli Zhou, li Xu, and Chunyuan Li, identification and antibiotic Activity of microorganisms from the Man grove Fungus sp.L28, chemistry of Natural Compounds 2017,53 (2): 237-240 ].
The banana anthracnose (Colletotrichum musae) and the tomato Fusarium oxysporum (Fusarium oxysporum) related in the invention are conventional plant pathogenic bacteria in the field; the banana Colletotrichum musae and tomato Fusarium oxysporum in the embodiment are disclosed in Chinese patent '201710676473.7, a dicoumarin derivative and a preparation method and application thereof'.
Example 1
18-hydroxyoleic acid diphenyl ether ester Phomaspether G was prepared by the following steps:
(1) Firstly, culturing the strain of the endophytic fungi Phoma sp L28 of the amaranthus strictus (Myoporum bentoides A.Gray) in a strain culture medium, wherein the strain culture medium contains 1.0 percent of glucose (weight percentage, the same below), 0.01 percent of yeast extract, 0.01 percent of peptone, 2.0 percent of agar, 0.2 percent of sodium chloride and the balance of water. When in use, the strain is made into a test tube inclined plane, and the strain is cultured for 5 days at 28 ℃;
(2) Performing fermentation culture on Phoma sp L28 in a fermentation medium of 0.0001% guaiacol (commercially available), semen oryzae Sativae 40% and water at room temperature of 20 deg.C for 60 days;
(3) Extracting the fermented strain in the step (2) with ethyl acetate for 3 times, concentrating the extract under reduced pressure, performing chromatographic separation in a 200-300-mesh silica gel column, and eluting with a petroleum ether-ethyl acetate mixed solvent, wherein the volume percentage of ethyl acetate is gradually increased from 0 to 25%; the eluates with 25% ethyl acetate were combined and then applied to a Sephadex LH-20 gel column (column length 150cm, inner diameter 1).5 cm) chromatography, using methanol mobile phase for separation; separating with High Performance Liquid Chromatography (HPLC) by using preparative HPLC: using a 5 μm-sized C18 packing chromatographic column with a mobile phase volume ratio and a flow rate of MeOH/H 2 Eluting O (v/v, 80, 20-100, 0,3.0mL/min, 0-15min, 0,3.0mL/min, 15-30 min) to obtain colorless oily matter in 20-24 min, namely the 18-hydroxyoleic acid diphenyl ether ester Phomaspether G.
Example 2
18-hydroxyoleic acid diphenyl ether ester Phomaspether G was prepared by the following steps:
(1) Firstly, culturing the strain of the endophytic fungi Phoma sp L28 of the amaranthus (Myoporum bentoides A.Gray) in a strain culture medium, wherein the strain culture medium contains 3.0 percent of glucose, 1.5 percent of yeast extract, 1.5 percent of peptone, 2.5 percent of agar, 2.0 percent of sodium chloride and the balance of water. When in use, the strain is made into a test tube inclined plane, and the strain is cultured for 10 days at the temperature of 20 ℃;
(2) Then carrying out fermentation culture on the Phoma sp L28, wherein the used fermentation culture medium comprises 0.00035% of guaiacol, 50% of polished round-grained rice and the balance of water; standing and culturing at 30 deg.C for 30 days;
(3) Extracting the strain fermented in the step (2) with dichloromethane for 5 times, concentrating the extract under reduced pressure, performing chromatographic separation in a 200-300-mesh silica gel column, and eluting with a petroleum ether-ethyl acetate mixed solvent, wherein the volume percentage of ethyl acetate is gradually increased from 0 to 25%; mixing the eluates with 25% ethyl acetate, performing Sephadex LH-20 gel column (column length 150cm, inner diameter 1.5 cm) chromatography, separating with methanol mobile phase, and separating with High Performance Liquid Chromatography (HPLC): using a C18 packed chromatographic column with the particle size of 5 mu m, the volume ratio and the flow rate of a mobile phase are MeOH/H 2 Eluting O (v/v, 80.
Example 3
18-hydroxyoleic acid diphenyl ether ester Phomaspether G was prepared by the following steps:
(1) Firstly, culturing the strain of the endophytic fungi Phoma sp L28 of the amaranthus (Myoporum bentioides A.Gray) in a strain culture medium, wherein the strain culture medium contains 2.0 percent of glucose, 1.0 percent of yeast extract, 1.0 percent of peptone, 2.0 percent of agar, 1.0 percent of sodium chloride and the balance of water. When in use, the strain is made into a test tube inclined plane, and the strain is cultured for 7 days at 25 ℃;
(2) Fermenting and culturing Phoma sp L28 with 0.00025% of guaiacol (chemical component separated from the strain host plant of Ixeris amara), 50% of semen oryzae Sativae, and water; standing and culturing at 25 deg.C for 45 days;
(3) Extracting the strain fermented in the step (2) with dichloromethane for 5 times, concentrating the extract under reduced pressure, performing chromatographic separation in a 200-300-mesh silica gel column, and eluting with a petroleum ether-ethyl acetate mixed solvent, wherein the volume percentage of ethyl acetate is gradually increased from 0 to 25%; mixing the eluates with 25% ethyl acetate, performing Sephadex LH-20 gel column (column length 150cm, inner diameter 1.5 cm) chromatography, separating with methanol mobile phase, and separating with High Performance Liquid Chromatography (HPLC): using a 5 μm-sized C18 packing chromatographic column with a mobile phase volume ratio and a flow rate of MeOH/H 2 Eluting O (v/v, 80.
The compound 18-hydroxyoleic acid diphenyl ether ester Phomaspeter G obtained in examples 1, 2 and 3 was examined for its spectral data as follows:
HRESIMS m/z 651.3506[M+Na] + (calcd for C 36 H 52 NaO 9 ,651.3509)； 1 H-NMR(600MHz,CD 3 COCD 3 )：6.43(d,1.8Hz,1H),5.96(d,1.8Hz,1H),11.15(s,1H),2.16(s,3H),4.43(qd,7.2Hz,2H),1.38(t,7.2Hz,3H),6.57(d,3.0Hz,1H),6.59(d,3.0Hz,1H),8.53(s,1H),3.80(s,3H),2.11(t,6.6Hz,2H),1.45(m,2H),1.26-1.32(br s,16H),2.03(m,4H),5.35(m,7.2,10.4Hz,2H),1.33(m,2H),1.50(m,2H),3.51(m,2H),3.39(t,6.6Hz,2H)；
13 C-NMR(150MHz,CD 3 COCD 3 )：δ102.8,162.8,111.4,146.1,106.5,159.8,171.0,21.7,61.9,14.3,134.3,131.6,106.4,158.4,103.3,151.3,61.7,55.6,173.1,34.1,25.2,29.4-30.2,27.5,130.3,26.4,33.5,62.2。
the structural formulae of the compounds obtained in examples 1, 2 and 3 are shown below:
example 4
The compound of the invention is used for the bacteriostatic activity test of banana anthracnose (Colletotrichum musae), tomato Fusarium oxysporum (Fusarium oxysporum) and O78 serotype chicken escherichia coli (purchased from Shanghai, xuan Yao biological science and technology Co., ltd):
the Minimum Inhibitory Concentration (MIC) of Phomaspether G, the compound obtained in example 1, against banana anthracnose, tomato fusarium wilt and O78 serotype chicken Escherichia coli was determined by a two-fold dilution method. And culturing the strain to be detected in a constant-temperature incubator at 28 ℃ for 24h, observing the growth condition of bacteria in the test tube, wherein the concentration corresponding to the test tube without bacteria growth is the minimum inhibitory concentration. Triazolone was used as a positive control for fungi (banana anthrax, tomato wilt) and cefradine as a positive control for bacteria (O78 serotype chicken escherichia coli). The results are shown in Table 1.
TABLE 1 antibacterial Activity of Phomaspether G (MIC, μ G/mL)
| Compound (I) | Banana anthrax | Tomato fusarium wilt bacterium | Escherichia coli O78 |
| Phomaspether G | 100 | 25 | 200 |
| Positive control | 80 | 100 | 12.5 |
Example 5
The compound of the invention is used for the test of the bactericidal activity of tomato fusarium wilt in greenhouse fields:
the compound (Phomaspether G) of the invention is tested for the control effect on tomato blight (Fusarium oxysporum) infected tomato leaves in a greenhouse according to the pesticide field efficacy test standard. Preparing Phomaspether G (prepared in example 1) solution with the concentration of 200, 400 and 800ppm, and when the concentration is 800, 400 and 200ppm in a preventive foliage spray test on tomato leaves infected with tomato fusarium wilt, the inhibition rates of the compound on the tomato fusarium wilt are 97 percent, 92 percent and 81 percent respectively (taking the preparation without spraying the compound as a blank control); in a therapeutic foliar spray test on tomato leaves infected with tomato fusarium oxysporum, the inhibition rate of the compound of the invention on tomato fusarium oxysporum is 73% and 52% when the concentration is 800 and 400ppm (taking a blank control without spraying the compound preparation of the invention).
Example 6
The bactericidal activity test of the compound of the invention on the banana colletotrichum after banana harvest preservation:
phomaspether G (prepared in example 1) solution was prepared at a concentration of 800ppm and was used for preventive surface spraying of bananas infected with the fungus Colletotrichum musae, with no spray of the compound preparation of the invention as a blank. After natural air drying, the mixture is placed in a room to be stored for 14 days at the temperature of 18-20 ℃, when the concentration is 800ppm, the good fruit rate after spraying the compound preparation is more than 51 percent, and the blank control good fruit rate without spraying the compound preparation is 18 percent.
The experimental results of the embodiments 4 to 6 show that the compound has stronger growth inhibition effect on banana anthracnose and tomato fusarium wilt, and can be added with various solvents and additives to be prepared into spray or powder to be used as an agricultural bactericide; meanwhile, the compound also has a moderate growth inhibition effect on O78 type chicken colibacillosis, and can be prepared into aqueous solutions of various salts (such as sodium chloride and the like) or mixed with feed for feeding or injection treatment or prevention of chicken colibacillosis.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. An 18-hydroxyoleic acid diphenyl ether ester, characterized in that: molecular formula C 36 H 52 O 9 The structural formula is shown as formula I:
2. a process for the preparation of a diphenyl ether-18-hydroxyoleate according to claim 1, characterized in that it comprises the following steps:
(1) Culturing strain of Phoma sp L28 in strain culture medium;
(2) And (2) carrying out fermentation culture on the strain obtained in the step (1) in a fermentation culture medium, then extracting with an organic solvent, and concentrating under reduced pressure to obtain the 18-hydroxy oleic acid diphenyl ether ester.
3. A process for the preparation of a diphenyl ether-18-hydroxyoleate according to claim 2, characterized in that:
the strain culture medium in the step (1) comprises the following components in percentage by weight: 1.0 to 3.5 percent of glucose, 0.01 to 2.0 percent of yeast extract, 0.01 to 2.0 percent of peptone, 2.0 to 3.0 percent of agar, 0.2 to 2.5 percent of sodium chloride and the balance of water;
the fermentation medium in the step (2) contains the following components in percentage by weight: 0.0001 to 0.00035 percent of guaiol, 40 to 60 percent of japonica rice and the balance of water.
4. A process for the preparation of a diphenyl ether-18-hydroxyoleate according to claim 2, characterized in that:
the culture conditions of the strains in the step (1) are as follows: culturing for 5-10 days at 20-35 ℃;
the conditions of the fermentation culture in the step (2) are as follows: culturing at 20-30 deg.c for 25-60 days.
5. A process for the preparation of a diphenyl ether-18-hydroxyoleate according to claim 2, characterized in that:
the organic solvent in the step (2) is one of ethyl acetate and dichloromethane;
the extraction times in the step (2) are 3-6 times.
6. The process for producing an 18-hydroxyoleic acid diphenylether ester as claimed in claim 2, characterized by further comprising, after the step (2), a step of further purifying the concentrate obtained by concentration under reduced pressure by column chromatography and/or high performance liquid chromatography;
the column chromatography is silica gel column chromatography and/or Sephdex LH-20 gel column chromatography;
the silica gel column chromatography is to carry out chromatographic separation in a silica gel column of 200-300 meshes;
gradient elution is carried out on the silica gel column chromatography by using a mixed solvent of petroleum ether and ethyl acetate as an eluent; the volume percent of ethyl acetate is gradually increased from 0 to 25 percent, and eluent of 25 percent ethyl acetate is combined;
the Sephadex LH-20 gel column chromatography adopts methanol as a mobile phase;
the conditions of the high performance liquid chromatography are as follows: adopting a C18 packing chromatographic column with the particle size of 5 mu m, taking methanol/water as a mobile phase, increasing the volume ratio of the methanol/water from 80; 15-30 min, the volume ratio of methanol/water is 100.
7. Use of the diphenyl ether 18-hydroxyoleate according to claim 1 in the preparation of phytopathogen agricultural fungicides and/or avian pathogenic escherichia coli antibacterial agents.
8. Use according to claim 7, characterized in that:
the plant pathogenic bacteria are banana anthracnose (Colletotrichum musae) and/or tomato Fusarium oxysporum (Fusarium oxysporum);
the avian pathogenic escherichia coli is chicken pathogenic escherichia coli.
9. Use according to claim 8, characterized in that:
the avian pathogenic escherichia coli is O78 serotype chicken escherichia coli.
10. Use according to any one of claims 7 to 9, characterized in that:
the plant pathogenic bacteria agricultural bactericide can be added with various auxiliary agents to prepare spray or powder;
the avian pathogenic escherichia coli antibacterial agent can be added with various auxiliary agents to be prepared into solution, spray or powder.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110148267.5A CN114920649B (en) | 2021-02-03 | 2021-02-03 | 18-hydroxyoleic acid diphenyl ether ester and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110148267.5A CN114920649B (en) | 2021-02-03 | 2021-02-03 | 18-hydroxyoleic acid diphenyl ether ester and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114920649A CN114920649A (en) | 2022-08-19 |
| CN114920649B true CN114920649B (en) | 2023-03-14 |
Family
ID=82804229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110148267.5A Active CN114920649B (en) | 2021-02-03 | 2021-02-03 | 18-hydroxyoleic acid diphenyl ether ester and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114920649B (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103768075A (en) * | 2014-01-26 | 2014-05-07 | 宜春学院 | Application of ethyl asterrate in preparation of anti-alzheimer medicine |
-
2021
- 2021-02-03 CN CN202110148267.5A patent/CN114920649B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103768075A (en) * | 2014-01-26 | 2014-05-07 | 宜春学院 | Application of ethyl asterrate in preparation of anti-alzheimer medicine |
Non-Patent Citations (4)
| Title |
|---|
| 《A new diphenyl ether from Phoma sp. strain, SHZK-2》;M.J. Fang等;《Natural Product Research》;第26卷(第13期);第1224-1228页 * |
| 《Barceloneic acid A, a new farnesyl-protein transferase inhibitor from a Phoma species》;HIRANTHI JAYASURIYA等;《Journal of Natural Products》;第58卷(第7期);第986-991页 * |
| 《Barceloneic acid C, a new polyketide from an endophytic fungus Phoma sp. JS752 and its antibacterial activities》;Xuekui Xia等;《The Journal of Antibiotics》;第68卷(第2期);第139-141页 * |
| 《Bioactive diphenyl ethers and isocoumarin derivatives from a gorgonian-derived fungus Phoma sp. (TA07-1)》;Ting Shi等;《Marine Drugs》;第15卷(第6期);第146/1-146/7页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114920649A (en) | 2022-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110863021B (en) | Preparation method and application of cytochalasin compound | |
| CN101720772B (en) | Macrolide composition for preventing and controlling fungal disease of crop and preparation process thereof | |
| CN112226470B (en) | Active substance for preventing and treating orobanche coerulescens, and extraction method and application thereof | |
| CN114920649B (en) | 18-hydroxyoleic acid diphenyl ether ester and preparation method and application thereof | |
| JPS6016236B2 (en) | Production method of antibiotic C-15003 P-3 | |
| CN110330544B (en) | 4,4, 1-bicyclic steroid compound and preparation method and application thereof | |
| CN101720781B (en) | New phosphorus and nitrogen mycin A for preventing and controlling fungal disease of crop and preparation process thereof | |
| EP0048585A1 (en) | Antibiotics TM-531 B and TM-531 C | |
| CN110357788B (en) | Polyketone compound and preparation method and application thereof | |
| CN111072670A (en) | Diketopiperazine compound and preparation method and application thereof | |
| CN114853581B (en) | Diphenyl ether phenol and preparation method and application thereof | |
| CN104059044A (en) | Xanthone derivative and preparation method and application of xanthone derivative | |
| CN112898161B (en) | 18-hydroxy octadecanoic carbonate containing diphenyl ether unit and preparation method and application thereof | |
| CN111011388B (en) | Application of dimethyl flavopenicillin in resisting plant pathogenic fungi | |
| CN115109023A (en) | Macrolide compound FWYZ52-A, and fermentation strain, fermentation method and application thereof | |
| CN110002996B (en) | Diphenyl ether compound and preparation method and application thereof | |
| CN108794502B (en) | Trichothecene compound and preparation method and application thereof | |
| CN112851610B (en) | Sesquiterpene derivative and preparation method and application thereof | |
| US10119158B2 (en) | Process for the preparation of fidaxomicin | |
| CN113308407A (en) | Streptomyces abyssocyanensis and Tianyamycin series compounds and application thereof | |
| CN107973803B (en) | Seven-membered lactonofuran derivative and preparation method and application thereof | |
| CN112625953A (en) | Alternaria alternata strain GW61 and application thereof | |
| CN110642823A (en) | Pyran derivative and preparation method and application thereof | |
| CN109912623B (en) | Xanthone compound, preparation method and application thereof | |
| CN109575040B (en) | Compound with antibacterial activity and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |