CN108586218A - A kind of chloro-cyclopentene ketone compounds and its preparation and application - Google Patents
A kind of chloro-cyclopentene ketone compounds and its preparation and application Download PDFInfo
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Abstract
The present invention relates to bacteriostatic agent fields, specifically the chloro-cyclopentene ketone compounds in a kind of seaweed endogenetic fungus source and preparation method thereof and the application at antibacterial aspect.Concrete structure formula is such as shown in (I), preparation method is that seaweed endogenetic fungus trichoderma asperellum (Trichoderma asperellum) cf44 2 is inoculated in fermented and cultured in fungi culture medium, tunning is after isolating and purifying, as chloro-cyclopentene ketone compounds shown in formula (I).The chloro-cyclopentene ketone compounds that the present invention obtains obtain antibacterial circle diameter of the compound at 20 micro- grams/piece up to 8.5 millimeters through bacteriostatic activity test.
Description
Technical field
The present invention relates to bacteriostatic agent fields, the specifically a kind of chloro-cyclopentene ketone in seaweed endogenetic fungus source
Close object and preparation method thereof and the application at antibacterial aspect.
Background technology
Culture fishery occupies important proportion in national economy, and aquaculture species are various at present, but nearly all
Breed variety is all by threats.Aquiculture disease takes place frequently, and not only causes great economic loss, is also aquatic product quality
Safety has buried hidden danger.According to aquiculture animal disease monitoring the results show that aquiculture disease type is up to more than 200 in recent years
Kind, wherein bacteriosis accounts for 48% or more.In bacillary aquatic animal disease, the vibriosis caused by vibrio bacteria is
Most important bacteriosis, the disease occurrence scope is wide, lethality is high, and can cause infecting both domestic animals and human, is aquiculture disease
One of main bugbear of prevention and control field.
In recent years, with a large amount of uses of traditional antibiotic in the development of aquaculture scale and aquaculture process,
The multidrug resistant phenomenon of bacterium is increasingly universal in aquiculture animal pathogen and breeding environment, and chemical synthetic drug is big
Amount use brings serious pollution to water body and soil, is all caused to biology and human health direct and potentially hazardous.
Compared with the conventional antibiotic and chemical synthetic drug that are used in culture fishery, marine organisms source natural drug tool
Have it is safe, with strong points, active it is notable, it is environmentally friendly and can solve at present most of aquatic products pathogen to tradition
The drug resistance problems of antibiotic, to solve the problems, such as that the prevention of the bacterial disease in current aquaculture process provides new think of
Road.
Invention content
The object of the present invention is to provide a kind of chloro-cyclopentene ketone compounds and its preparations and application.
To achieve the above object, the technical solution adopted by the present invention is：
A kind of chloro-cyclopentene ketone compounds, shown in chloro-cyclopentene ketone compounds structure such as formula (I)
A kind of preparation method of chloro-cyclopentene ketone compounds, by trichoderma asperellum cf44-2 (Trichoderma
Asperellum cf44-2) it is inoculated in fermented and cultured in fungi culture medium, after tunning is purified, as shown in formula (I)
Chloro-cyclopentene ketone compounds；The trichoderma asperellum cf44-2 (Trichoderma asperellum cf44-2) in
It is stored in China typical culture collection center CCTCC on June 22nd, 2017, deposit number is CCTCC NO:M 2017360.
Further：
1) trichoderma asperellum cf44-2 (Trichoderma asperellum cf44-2) is inoculated in fungi culture medium and is sent out
Ferment 10-60 days, and after extract and concentrate through organic solvent, as crude extract；
2) it takes the crude extract in step 1) to carry out silica gel column chromatography, carries out gradient elution with organic solvent, collect eluent,
Eluent is detected through thin-layer chromatography；
3) collection step 2) in elution fraction inverted silica gel column chromatography, gel filtration chromatography and prepare thin-layer chromatography successively again
It isolates and purifies to get the chloro-cyclopentene ketone compounds as shown in formula (I).
4. the preparation method of chloro-cyclopentene ketone compounds as described in claim 3, it is characterised in that：In step 1)
Fungi culture medium is potato dextrose broth, jerusalem artichoke dextrose broth or rice solid medium.
Organic solvent extracting solution is ethyl acetate, petroleum ether, n-hexane, hexamethylene, dichloromethane, methanol, ethyl alcohol, propyl alcohol
Or it is one or more of in isopropanol.
Organic solvent in the step 2) is volume ratio 50-0:1 petroleum ether-ethyl acetate, petroleum ether-ethyl alcohol, stone
Oily ether-propyl alcohol, petroleum ether-isopropanol, dichloromethane-ethyl acetate, methylene chloride-methanol, dichloromethane-ethanol, dichloromethane
One group in alkane-propyl alcohol, dichloromethane-isopropanol or several groups.
Step 3) the reversed-phase silica gel column chromatography eluent is volume ratio 5-0:1 water-methanol or water-ethanol；It is solidifying
Plastic column chromatography eluent is volume ratio 2-0:1 methylene chloride-methanol or dichloromethane-ethanol；Prepare thin-layer chromatography solvent
It is 10-0 for volume ratio:1 methylene chloride-methanol or petroleum ether-ethyl alcohol.
A kind of application of chloro-cyclopentene ketone compounds, the chloro-cyclopentene ketone compounds are being used to prepare carefully
Application in the bacteriostatic agent of bacterium.
The bacterium is Vibrio anguillarum, Vibrio harveyi, vibrio parahemolyticus or the Vibrio splindidus of aquatic products pathogen.
The present invention has the following advantages：The present invention is by being located away from the trichoderma asperellum cf44-2 of marine brown sargassum
The chloro-cyclopentene ketone compounds that (Trichoderma asperellum cf44-2) fermentation is extracted, separation obtains, through suppression
Bacterium activity experiment show that compound is molten to aquatic products pathogen-Vibrio anguillarum, Vibrio harveyi, pair under 20 micro- grams/piece of concentration
The antibacterial circle diameter of courageous and upright vibrios and Vibrio splindidus is respectively 8.5 millimeters, 8.0 millimeters, 6.7 millimeters and 6.5 millimeters.
Specific implementation mode：
The present invention is further elaborated with reference to embodiment.
Embodiment 1
Shown in the chloro-cyclopentene ketone compounds structure in seaweed endogenetic fungus source such as formula (I).
The compound has following physics and chemistry and spectral characteristic：
Colorless oil；Specific rotatory power [α]25 D+7.5(c 0.040,MeOH)；Nuclear magnetic resonance spectroscopy (solvent is deuterated methanol)
δH 2.88ddd(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)；Carbon-13 nmr spectra (solvent is deuterochloroform) δC 200.1(C),44.0(CH2),68.4(CH),175.4(C),
131.5(C),66.3(CH),21.8(CH3)；High resolution mass spectrum [M]+M/z 176.0236, calculated value 176.0240.
Embodiment 2
The preparation method of chloro-cyclopentene ketone compounds as shown in formula (I)：
It makes even well-grown trichoderma asperellum (Trichoderma asperellum) cf44-2 strains on plate, is cut into small pieces
And be inoculated in potato dextrose broth, 300 milliliters of culture mediums are put in every 1 liter of triangular flask, totally 200 bottles, room temperature is quiet
It only ferments 30 days, tunning is extracted with ethyl acetate three times, is concentrated under reduced pressure, 83.7 grams of crude extract is there are after concentration.
The potato dextrose broth group becomes every liter of 500 milliliters of liquor for containing 200 g potatos, glucose
20 grams, 5 grams of peptone, 5 grams of yeast powder, 500 milliliters of Chen Haishui.
Trichoderma asperellum cf44-2 (Trichoderma asperellum cf44-2) strains were preserved on June 22nd, 2017
In China typical culture collection center CCTCC, address：Wuhan, China university, deposit number are CCTCC NO:M 2017360,
Classification And Nomenclature is Trichoderma asperellum, and strain number is cf44-2.
By silica gel column chromatography of the crude extract through 100-200 mesh, volume ratio 50 is used successively:1、20:1、10:1、5:1、2:1、1:
1 to 0:1 petroleum ether-ethyl acetate and 20:1、10:1、5:1、2:1 to 1:1 methylene chloride-methanol carries out gradient elution, point
Eluent is not collected, and each component of collection uses thin-layer chromatography (TLC) to detect (volume ratio 100-1 again：1 methylene chloride-methanol exhibition
Open, anisaldehyde-sulfuric acid colour developing or the ultraviolet light detections of 254nm), judge, merge same or like part according to Rf values, obtains 12
A component (1-12).
It is 0.6-0.7 (volume ratios 10 by Rf values:1 methylene chloride-methanol expansion, the ultraviolet light detections of 254nm) component
8, i.e., with volume ratio 1:Component under 1 petroleum ether-ethyl acetate gradient elution inverted C successively again18Silicagel column, Sephadex
LH-20 gel columns are detached with thin-layer chromatography is prepared.Reverse phase C18Silica gel column chromatography eluent is volume ratio 4:1 water-methanol, TLC
Detect (volume ratio 10:1 methylene chloride-methanol expansion, the ultraviolet light detections of 254nm), collecting under 254nm ultraviolet lights has fluorescence
Component；Eluent is methanol when collection group lease making Sephadex LH-20 gel filtration chromatographies, and TLC detects (volume ratio 10:The two of 1
Chloromethanes-methanol expansion, the ultraviolet light detections of 254nm), collect the component for having fluorescence under 254nm ultraviolet lights；Component is collected again through system
Standby thin-layer chromatography, with volume ratio 10:1 methylene chloride-methanol is solvent, collects the component that Rf values are 0.6-0.7, as
Compound (1.1 milligrams) shown in formula (I).(volume ratio 10 is detected through thin-layer chromatography:1 methylene chloride-methanol is unfolded, and 254nm is ultraviolet
Light detection), it is in single, uniform fluorescence spot, is determined as pure compound.Through Spectrum Analysis, Structural Identification is a kind of chloro ring
Amylene ketone compounds, structural formula is such as shown in (I).
Embodiment 3
Difference from Example 2 is
It makes even well-grown trichoderma asperellum cf44-2 (Trichoderma asperellum cf44-2) strain on plate,
It is cut into small pieces and is inoculated in jerusalem artichoke dextrose broth, 300 milliliters of culture mediums is put in every 1 liter of triangular flask, totally 200 bottles,
The static fermentation of room temperature 40 days then three times with dichloromethane extraction is concentrated under reduced pressure, 80 grams of crude extract is obtained after concentration.
The jerusalem artichoke dextrose broth group becomes every liter of 500 milliliters of liquor for containing 200 grams of jerusalem artichoke stem tubers, glucose
20 grams, 5 grams of peptone, 5 grams of yeast powder, 500 milliliters of Chen Haishui.
By silica gel column chromatography of the crude extract through 200-300 mesh, volume ratio 50 is used successively:1、30:1、15:1、10:1、5:1、
2:1、1:1 to 0:1 petroleum ether-ethyl alcohol carries out gradient elution, collects eluent respectively, then detect (volume ratio with thin-layer chromatography
50-0：1 petroleum ether-ethyl alcohol expansion, anisaldehyde-sulfuric acid colour developing or the ultraviolet light detections of 254nm), judge, merge according to Rf values
Same or like part obtains 8 components (1-8).
It is 0.6-0.7 (volume ratios 7 by Rf values:The expansion of 1 petroleum ether-ethyl alcohol, the ultraviolet light detections of 254nm) component 3, i.e.,
With volume ratio 15:Component under 1 petroleum ether-ethanol gradient elution inverted C successively again18Silicagel column, Sephadex LH-20
Gel column is detached with thin-layer chromatography is prepared.Reverse phase C18Silica gel column chromatography eluent is volume ratio 2:1 water-ethanol, TLC detections
(volume ratio 7:1 petroleum ether-ethyl alcohol expansion, the ultraviolet light detections of 254nm), collect the component for having fluorescence under 254nm ultraviolet lights；It receives
For eluent as ethyl alcohol, TLC detects (volume ratio 7 when integrating group lease making Sephadex LH-20 gel filtration chromatographies:1 petroleum ether-ethyl alcohol
Expansion, the ultraviolet light detections of 254nm), collect the component for having fluorescence under 254nm ultraviolet lights；Collection group lease making prepares thin-layer chromatography, body
Product ratio 7:1 petroleum ether-ethyl alcohol is solvent, collects the component that Rf values are 0.6-0.7, obtains chloro-cyclopentene ketone shown in formula (I)
Class compound.
Embodiment 4
Bacteriostatic activity test：
Specially：It is inoculated in 2216E culture mediums respectively for examination bacterium, and is cultivated 24 hours in 37 DEG C, then draws 4 milliliters
Sterile 0.85%NaCl solution carries out washing culture, and glass slicker is used in combination gently to scrape bacterium, is drawn with liquid-transfering gun appropriate
Bacteria suspension in sterile test tube, then with 0.85%NaCl solution by bacteria suspension be adjusted to 0.5 Maxwell turbidity (be equivalent to 1.5 ×
108CFU/ milliliters).Wherein, strains tested is respectively：Vibrio anguillarum, Vibrio harveyi, vibrio parahemolyticus or Vibrio splindidus.
Bacteria suspension is leached with aseptic cotton carrier, is uniformly applied on culture medium.(above-described embodiment prepares formula to test sample
(I) chloro-cyclopentene ketone compounds shown in) it is dissolved in dimethyl sulfoxide (DMSO) (DMSO), a concentration of 4.0 mg/ml.It takes 5 micro-
The aseptic filter paper on piece (every 20 micrograms) that sample is added to a diameter of 5 millimeters is risen, the filter paper added with same volume DMSO is used in combination
Negative control is done, uses chloramphenicol as positive control, each three parallel.It is placed in 37 DEG C of standing trainings added with the plating medium of sample
It supports 24 hours, observation experiment is as a result, there is the measurement of inhibition zone its antibacterial circle diameter.
Experimental result：The chloro-cyclopentene ketone compounds of above-mentioned acquisition are to aquatic products pathogen-Vibrio anguillarum, Kazakhstan Vickers arc
The antibacterial circle diameter of bacterium, vibrio parahemolyticus and Vibrio splindidus is respectively 8.5 millimeters, 8.0 millimeters, 6.7 millimeters and 6.5 millimeters,
Have the function of inhibiting Vibrio anguillarum, Vibrio harveyi, vibrio parahemolyticus or Vibrio splindidus.
Claims (8)
1. a kind of chloro-cyclopentene ketone compounds, it is characterised in that：Shown in chloro-cyclopentene ketone compounds structure such as formula (I)
2. a kind of preparation method of chloro-cyclopentene ketone compounds described in claim 1, it is characterised in that：By trichoderma asperellum
Cf44-2 (Trichoderma asperellum cf44-2) is inoculated in fermented and cultured in fungi culture medium, and tunning is through pure
After change, as chloro-cyclopentene ketone compounds shown in formula (I)；Trichoderma asperellum cf44-2 (the Trichoderma
Asperellum cf44-2) on June 22nd, 2017 it is stored in China typical culture collection center CCTCC, deposit number is
CCTCC NO：M 2017360.
3. the preparation method of chloro-cyclopentene ketone compounds as described in claim 2, it is characterised in that specific preparation process：
1) trichoderma asperellum cf44-2 (Trichoderma asperellum cf44-2) is inoculated in fungi culture medium and is fermented
10-60 days, and after extract and concentrate through organic solvent, as crude extract；
2) it takes the crude extract in step 1) to carry out silica gel column chromatography, gradient elution is carried out with organic solvent, collect eluent, elution
Liquid is detected through thin-layer chromatography；
3) collection step 2) in elution fraction again successively inverted silica gel column chromatography, gel filtration chromatography and prepare thin-layer chromatography separation
Purifying is to get the chloro-cyclopentene ketone compounds as shown in formula (I).
4. the preparation method of chloro-cyclopentene ketone compounds as described in claim 3, it is characterised in that：Fungi in step 1)
Culture medium is potato dextrose broth, jerusalem artichoke dextrose broth or rice solid medium.
Organic solvent extracting solution is ethyl acetate, petroleum ether, n-hexane, hexamethylene, dichloromethane, methanol, ethyl alcohol, propyl alcohol or different
It is one or more of in propyl alcohol.
5. the preparation method of chloro-cyclopentene ketone compounds as described in claim 3, it is characterised in that：Having in step 2)
Solvent is volume ratio 50-0:1 petroleum ether-ethyl acetate, petroleum ether-ethyl alcohol, petroleum ether-propyl alcohol, petroleum ether-isopropanol,
In dichloromethane-ethyl acetate, methylene chloride-methanol, dichloromethane-ethanol, dichloromethane-propyl alcohol, dichloromethane-isopropanol
One group or several groups.
6. the preparation method of chloro-cyclopentene ketone compounds as described in claim 3, it is characterised in that：Step 3) is described anti-
Phase silica gel column chromatography eluent is volume ratio 5-0:1 water-methanol or water-ethanol；Gel filtration chromatography eluent is volume ratio 2-
0:1 methylene chloride-methanol or dichloromethane-ethanol；It is 10-0 that prepare thin-layer chromatography solvent, which be volume ratio,:1 dichloromethane
Alkane-methanol or petroleum ether-ethyl alcohol.
7. a kind of application of chloro-cyclopentene ketone compounds described in claim 1, it is characterised in that：The chloro ring penta
Application of the ketene compounds in the bacteriostatic agent for being used to prepare bacterium.
8. the application of chloro-cyclopentene ketone compounds as described in claim 7, it is characterised in that：The bacterium is aquatic products disease
Vibrio anguillarum, Vibrio harveyi, vibrio parahemolyticus or the Vibrio splindidus of evil bacterium.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113545350A (en) * | 2021-08-18 | 2021-10-26 | 湖北省生物农药工程研究中心 | Application of 4, 5-dihydroxy-2-methyl-ketene in preparation of bacterial inhibitor |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113545350A (en) * | 2021-08-18 | 2021-10-26 | 湖北省生物农药工程研究中心 | Application of 4, 5-dihydroxy-2-methyl-ketene in preparation of bacterial inhibitor |
| CN113545350B (en) * | 2021-08-18 | 2022-05-03 | 湖北省生物农药工程研究中心 | Application of 4, 5-dihydroxy-2-methyl-ketene in preparation of bacterial inhibitor |
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