CN108586218B - Chloro cyclopentenone compound and preparation and application thereof - Google Patents
Chloro cyclopentenone compound and preparation and application thereof Download PDFInfo
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- CN108586218B CN108586218B CN201810532429.3A CN201810532429A CN108586218B CN 108586218 B CN108586218 B CN 108586218B CN 201810532429 A CN201810532429 A CN 201810532429A CN 108586218 B CN108586218 B CN 108586218B
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/79—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/707—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a three- to five-membered ring
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- 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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- 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
- C12N1/145—Fungal isolates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
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- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/645—Fungi ; Processes using fungi
- C12R2001/885—Trichoderma
Abstract
The invention relates to the field of bacteriostat, in particular to a chloro cyclopentenone compound from seaweed endophytic fungi, a preparation method thereof and application thereof in bacteriostasis. The preparation method comprises the steps of inoculating the marine algae endophytic fungus Trichoderma asperellum cf44-2 into a fungus culture medium for fermentation culture, and separating and purifying the fermentation product to obtain the chloro cyclopentenone compound shown in the formula (I). The chlorocyclopentenone compound obtained by the invention has the antibacterial activity experiment that the diameter of an antibacterial zone of the compound can reach 8.5 mm when 20 micrograms/tablet
Description
Technical Field
The invention relates to the field of bacteriostat, in particular to a chloro cyclopentenone compound from seaweed endophytic fungi, a preparation method thereof and application thereof in bacteriostasis.
Background
The aquaculture industry has an important proportion in national economy, and at present, the aquaculture varieties are various, but almost all aquaculture varieties are threatened by diseases. The aquaculture diseases are frequent, so that not only is the great economic loss caused, but also the hidden danger is buried for the quality safety of the aquatic products. According to the disease monitoring results of aquaculture animals, the disease types of aquaculture animals are as high as more than 200 in recent years, wherein bacterial diseases account for more than 48%. Among bacterial aquatic animal diseases, vibriosis caused by vibrio bacteria is the most important bacterial disease, has wide occurrence range and high lethality rate, can cause zoonosis, and is one of the main problems in the field of disease control of aquaculture.
In recent years, with the development of aquaculture scale and the use of a large amount of traditional antibiotics in the aquaculture process, the multi-drug resistance phenomenon of pathogenic bacteria of aquaculture animals and bacteria in the aquaculture environment is increasingly common, and the use of a large amount of chemical synthetic drugs brings serious pollution to water and soil and causes direct and potential harm to the health of organisms and human beings.
Compared with the traditional antibiotics and chemical synthetic drugs used in the aquaculture industry, the marine organism-derived natural drug has high safety, strong pertinence, remarkable activity and environmental friendliness, can solve the problem of drug resistance of most of current aquatic disease bacteria to the traditional antibiotics, and provides a new idea for solving the problem of bacterial disease control in the current aquaculture process.
Disclosure of Invention
The invention aims to provide a chloro cyclopentenone compound and preparation and application thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a chloro cyclopentenone compound has a structure shown in formula (I)
A preparation method of chloro-cyclopentenone compounds comprises inoculating Trichoderma asperellum cf44-2(Trichoderma asperellum cf44-2) into a fungus culture medium for fermentation culture, and purifying the fermentation product to obtain chloro-cyclopentenone compounds represented by formula (I); the Trichoderma asperellum cf44-2(Trichoderma asperellum cf44-2) is preserved in China Center for Type Culture Collection (CCTCC) in 2017, 6 and 22 months, and the preservation number is M2017360.
Further, the following steps are carried out:
1) inoculating Trichoderma asperellum cf44-2(Trichoderma asperellum cf44-2) into a fungus culture medium, fermenting for 10-60 days, extracting by an organic solvent and concentrating to obtain a crude extract;
2) subjecting the crude extract obtained in the step 1) to silica gel column chromatography, performing gradient elution by using an organic solvent, collecting eluent, and detecting the eluent by thin layer chromatography;
3) collecting the eluted components in the step 2), and sequentially carrying out reverse phase silica gel column chromatography, gel column chromatography and preparation thin layer chromatography for separation and purification to obtain the chloro cyclopentenone compound shown in the formula (I).
The fungus culture medium in the step 1) is a potato glucose liquid culture medium, a jerusalem artichoke glucose liquid culture medium or a rice solid culture medium.
The organic solvent extract is one or more of ethyl acetate, petroleum ether, n-hexane, cyclohexane, dichloromethane, methanol, ethanol, propanol or isopropanol.
The organic solvent in the step 2) is one or more of petroleum ether-ethyl acetate, petroleum ether-ethanol, petroleum ether-propanol, petroleum ether-isopropanol, dichloromethane-ethyl acetate, dichloromethane-methanol, dichloromethane-ethanol, dichloromethane-propanol and dichloromethane-isopropanol in a volume ratio of 50-0: 1.
The reverse phase silica gel column chromatography eluent in the step 3) is water-methanol or water-ethanol with the volume ratio of 5-0: 1; the eluent of the gel column chromatography is dichloromethane-methanol or dichloromethane-ethanol with the volume ratio of 2-0: 1; the thin layer chromatography developing solvent is prepared from dichloromethane-methanol or petroleum ether-ethanol with volume ratio of 10-0: 1.
The application of the chloro cyclopentenone compound in preparing a bacteriostatic agent for bacteria.
The bacteria are vibrio anguillarum, vibrio harveyi, vibrio parahaemolyticus or vibrio splendidus of aquatic disease bacteria.
The invention has the following advantages: the invention obtains chloro cyclopentenone compounds through extraction and separation by fermenting Trichoderma asperellum cf44-2(Trichoderma asperellum cf44-2) separated from marine brown algae gulfweed, and bacteriostatic activity experiments show that the diameters of bacteriostatic rings of the compounds on aquatic disease bacteria such as vibrio anguillarum, vibrio harveyi, vibrio parahaemolyticus and vibrio lautus are respectively 8.5 mm, 8.0 mm, 6.7 mm and 6.5 mm under the concentration of 20 micrograms per tablet.
The specific implementation mode is as follows:
the invention is further illustrated below with reference to the examples of embodiment.
Example 1
The structure of the chloro cyclopentenone compound from the seaweed endophytic fungi is shown as the formula (I).
The compound has the following physicochemical and spectral characteristics:
colorless oil; specific optical rotation [ alpha ]]25 D+7.5(c 0.040, MeOH); hydrogen nuclear magnetic resonance spectrum (solvent is deuterated methanol) deltaH2.88ddd (18.6,6.3,0.9),2.30dd (18.6,1.7),5.14dd (6.3,1.5),4.97q (6.9),1.51d (6.9); nuclear magnetic resonance carbon spectrum (solvent is deuterated chloroform) deltaC 200.1(C),44.0(CH2),68.4(CH),175.4(C),131.5(C),66.3(CH),21.8(CH3) (ii) a High resolution mass spectrometry [ M ]]+m/z 176.0236, calculated 176.0240.
Example 2
A preparation method of chloro cyclopentenone compounds shown as a formula (I) comprises the following steps:
taking Trichoderma asperellum cf44-2 strain growing well on a flat plate, cutting into small pieces, inoculating into potato glucose liquid culture medium, putting 300 ml of culture medium into each 1L triangular flask, standing and fermenting for 30 days at room temperature in 200 bottles, extracting the fermentation product with ethyl acetate for three times, concentrating under reduced pressure, and concentrating to obtain 83.7 g of crude extract.
The potato glucose liquid culture medium comprises 500 ml of cooking juice containing 200 g of potatoes per liter, 20 g of glucose, 5 g of peptone, 5 g of yeast powder and 500 ml of old seawater.
Trichoderma asperellum cf44-2(Trichoderma asperellum cf44-2) strain was preserved in China center for type culture Collection CCTCC at 6 month and 22 days 2017, address: the preservation number of the university of Wuhan, China is CCTCC NO: M2017360, the university of Wuhan is named as Trichoderma asperellum in a classification way, and the strain number is cf 44-2.
Subjecting the crude extract to 100-mesh 200-mesh silica gel column chromatography, performing gradient elution sequentially with petroleum ether-ethyl acetate and dichloromethane-methanol at volume ratios of 50:1, 20:1, 10:1, 5:1, 2:1, 1:1 to 0:1 and 20:1, 10:1, 5:1, 2:1 to 1:1, respectively collecting eluates, detecting the collected components by Thin Layer Chromatography (TLC) (dichloromethane-methanol development at volume ratio of 100-1: 1, anisaldehyde-sulfuric acid color development or 254nm ultraviolet light detection), judging and combining the same or similar parts according to Rf value to obtain 12 components (1-12).
Component 8 with Rf value of 0.6-0.7 (volume ratio of 10:1 dichloromethane-methanol development, 254nm ultraviolet detection), that is, component eluted by petroleum ether-ethyl acetate gradient with volume ratio of 1:1, is sequentially subjected to reversed phase C18Silica gel column, Sephadex LH-20 gel column and preparative thin layer chromatography. Inverse phase C18Performing TLC (TLC) detection (dichloromethane-methanol development and 254nm ultraviolet detection at a volume ratio of 10: 1) on silica gel column chromatography eluent by using water-methanol at a volume ratio of 4:1, and collecting components with fluorescence under 254nm ultraviolet light; collecting eluate of Sephadex LH-20 gel column chromatography, detecting by TLC (dichloromethane-methanol at volume ratio of 10:1, detecting by 254nm ultraviolet light), and collecting component with fluorescence under 254nm ultraviolet light; collecting fractions, performing thin layer chromatography with dichloromethane-methanol at volume ratio of 10:1 as developing agent, and collecting fraction with Rf value of 0.6-0.7 to obtain compound (1.1 mg) shown in formula (I). Detecting by thin layer chromatography (volume ratio of 10:1 dichloromethane-methanol development, 254nm ultraviolet detection), and determining as pure compound as single and uniform fluorescent spot. The structure is identified as a chloro cyclopentenone compound through spectral analysis, and the structural formula is shown as (I).
Example 3
The difference from the embodiment 2 is that
Taking Trichoderma asperellum cf44-2(Trichoderma asperellum cf44-2) strains growing well on a plate, cutting into small blocks, inoculating the small blocks into a jerusalem artichoke glucose liquid culture medium, putting 300 ml of the culture medium into each 1L triangular flask, standing and fermenting for 40 days at room temperature, extracting with dichloromethane for three times, concentrating under reduced pressure, and concentrating to obtain 80 g of crude extract.
The jerusalem artichoke glucose liquid culture medium comprises 500 ml of boiling juice containing 200 g of jerusalem artichoke tubers per liter, 20 g of glucose, 5 g of peptone, 5 g of yeast powder and 500 ml of aged seawater.
Subjecting the crude extract to 200-mesh 300-mesh silica gel column chromatography, sequentially performing gradient elution with petroleum ether-ethanol at volume ratio of 50:1, 30:1, 15:1, 10:1, 5:1, 2:1, 1:1 to 0:1, respectively collecting eluates, detecting by thin layer chromatography (petroleum ether-ethanol at volume ratio of 50-0:1 is developed, anisaldehyde-sulfuric acid is developed or 254nm ultraviolet light is detected), and judging and combining the same or similar parts according to Rf value to obtain 8 components (1-8).
Component 3 with Rf value of 0.6-0.7 (petroleum ether-ethanol expansion at volume ratio of 7:1, 254nm ultraviolet detection), that is, component eluted by petroleum ether-ethanol gradient at volume ratio of 15:1, is sequentially subjected to reversed phase C18Silica gel column, Sephadex LH-20 gel column and preparative thin layer chromatography. Inverse phase C18Performing silica gel column chromatography on the eluent which is water-ethanol with the volume ratio of 2:1, performing TLC detection (petroleum ether-ethanol development with the volume ratio of 7:1 and 254nm ultraviolet detection), and collecting components with fluorescence under 254nm ultraviolet light; collecting eluate of Sephadex LH-20 gel column chromatography, detecting by TLC (petroleum ether-ethanol at volume ratio of 7:1, detecting by 254nm ultraviolet light), and collecting components with fluorescence under 254nm ultraviolet light; collecting the components, performing thin layer chromatography, using petroleum ether-ethanol with volume ratio of 7:1 as developing agent, and collecting the components with Rf value of 0.6-0.7 to obtain chloro cyclopentenone compounds represented by formula (I).
Example 4
And (3) bacteriostatic activity experiment:
the method specifically comprises the following steps: the test bacteria were inoculated in 2216E medium and cultured at 37 ℃ for 24 hours, then 4 ml of sterile 0.85% NaCl solution was aspirated to wash the culture, the bacteria were gently scraped off with a glass scraper, an appropriate amount of the bacterial suspension was aspirated into a sterile test tube with a pipette gun, and then the bacterial suspension was adjusted to 0.5 McLeod (equivalent to 1.5X 10) with 0.85% NaCl solution8CFU/ml). Wherein, the test strains are respectively: vibrio anguillarum, Vibrio harveyi, Vibrio parahaemolyticus, or Vibrio lautus.
The bacterial suspension is leached by a sterile cotton swab and is evenly coated on a culture medium. The test sample (chloro-cyclopentenone compound of formula (I) prepared in the above example) was dissolved in dimethyl sulfoxide (DMSO) at a concentration of 4.0 mg/ml. Samples of 5. mu.l were applied to 5 mm diameter sheets of sterile filter paper (20. mu.g per sheet) and filter paper sheets loaded with the same volume of DMSO were used as negative controls and chloramphenicol as positive controls, three in parallel. The plate culture medium with the sample is placed at 37 ℃ for static culture for 24 hours, the experimental result is observed, and the diameter of the inhibition zone is measured when the inhibition zone appears.
The experimental results are as follows: the obtained chloro cyclopentenone compounds have inhibition zone diameters of 8.5 mm, 8.0 mm, 6.7 mm and 6.5 mm for aquatic disease bacteria such as Vibrio anguillarum, Vibrio harveyi, Vibrio parahaemolyticus and Vibrio lautus, and have effects of inhibiting Vibrio anguillarum, Vibrio harveyi, Vibrio parahaemolyticus or Vibrio lautus.
Claims (8)
1. A chloro cyclopentenone compound is characterized in that: the structure of the chloro cyclopentenone compound is shown as the formula (I)
（I）。
2. A process for the preparation of a chlorocyclopentenone compound according to claim 1, characterized in that: inoculating trichoderma asperellum cf44-2 into a fungus culture medium for fermentation culture, and purifying a fermentation product to obtain a chloro cyclopentenone compound shown in a formula (I); the trichoderma asperellum cf44-2 is stored in China Center for Type Culture Collection (CCTCC) in 2017, 6 and 22 months, and the preservation number is CCTCC NO: m2017360;
（I）。
3. the process for the preparation of chlorocyclopentenones according to claim 2, characterized by the specific steps of:
1) inoculating trichoderma asperellum cf44-2 into a fungus culture medium, fermenting for 10-60 days, extracting by an organic solvent and concentrating to obtain a crude extract;
2) subjecting the crude extract obtained in the step 1) to silica gel column chromatography, performing gradient elution by using an organic solvent, collecting eluent, and detecting the eluent by thin layer chromatography;
3) collecting the eluted components in the step 2), and sequentially carrying out reverse phase silica gel column chromatography, gel column chromatography and preparation thin layer chromatography for separation and purification to obtain the chloro cyclopentenone compound shown in the formula (I).
4. A process for the preparation of chlorocyclopentenones according to claim 3, characterized in that: the fungus culture medium in the step 1) is a potato glucose liquid culture medium, a jerusalem artichoke glucose liquid culture medium or a rice solid culture medium;
the organic solvent extractive solution is one or more of ethyl acetate, petroleum ether, n-hexane, cyclohexane, dichloromethane, methanol, ethanol, propanol or isopropanol.
5. A process for the preparation of chlorocyclopentenones according to claim 3, characterized in that: the organic solvent in the step 2) is one or more than two groups of petroleum ether-ethyl acetate, petroleum ether-ethanol, petroleum ether-propanol, petroleum ether-isopropanol, dichloromethane-ethyl acetate, dichloromethane-methanol, dichloromethane-ethanol, dichloromethane-propanol and dichloromethane-isopropanol in a volume ratio of 50-0: 1.
6. A process for the preparation of chlorocyclopentenones according to claim 3, characterized in that: the reverse phase silica gel column chromatography eluent in the step 3) is water-methanol or water-ethanol with the volume ratio of 5-0: 1; the eluent of the gel column chromatography is dichloromethane-methanol or dichloromethane-ethanol with the volume ratio of 2-0: 1; the thin layer chromatography developing solvent is prepared from dichloromethane-methanol or petroleum ether-ethanol with volume ratio of 10-0: 1.
7. Use of a chlorinated cyclopentenone compound according to claim 1, wherein: the chloro cyclopentenone compound is applied to preparing bacteriostatic agents of bacteria.
8. Use of a chlorinated cyclopentenone according to claim 7, characterized in that: the bacteria are vibrio anguillarum, vibrio harveyi, vibrio parahaemolyticus or vibrio splendidus of aquatic disease bacteria.
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| Cytotoxic Substances Produced by a Fungal Strain from a Sponge;taro amagata等;《the journal of antibiotics》;19971231;第51卷(第1期);第33-40页 * |
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