CN110003041A - A kind of ring flores aurantii alkane acylated derivatives and its preparation and application - Google Patents
A kind of ring flores aurantii alkane acylated derivatives and its preparation and application Download PDFInfo
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- A01N37/18—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 the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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- C07C235/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and unsaturated
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Abstract
The present invention relates to algae-inhibiting agent fields, specifically the ring flores aurantii alkane acylated derivatives in a kind of seaweed endogenetic fungus source and preparation method thereof and the application in terms of algal control.Concrete structure formula is such as shown in (I); preparation method is that seaweed endogenetic fungus trichoderma asperellum (Trichoderma asperellum) A-YMD-9-2 is inoculated in fermented and cultured in fungi culture medium; tunning is after isolating and purifying, as ring flores aurantii alkane acylated derivatives shown in formula (I).The ring flores aurantii alkane acylated derivatives that the present invention obtains obtain compound to the half-inhibitory concentration of microalgae up to 5.2 mcg/mls through suppression activity of microalgae experiment.
Description
Technical field
The present invention relates to algae-inhibiting agent fields, and specifically a kind of ring flores aurantii alkane in seaweed endogenetic fungus source is acylated derives
Object and preparation method thereof and the application in terms of algal control.
Background technique
Harmful algal bloom is the common ecological abnormal phenomenon in coastal waters, once occurring, will be continued for an extended period of time, to seawater
Cultivation, ecological safety and human health constitute a threat to, it has also become a kind of marine ecology disaster problem outstanding.After 2000 I
State enters the red tide high-incidence season, and red tide occurrence frequency and the extent of injury obviously increase.There are four types of the main harm forms of red tide, first is that
Destroy marine ecology balance；Second is that destroying marine fishery resources；Third is that endangering human health；Fourth is that influencing the hair of marine tourism
Exhibition.According to statistics, the economic loss as caused by red tide is up to 1,000,000,000 yuan or more every year.Can cause in ocean the microalgae of red tide there are about
300 kinds, wherein about 80 kinds of toxic red tide algae.Scientificlly and effectively prevent and administer red tide to be one of world today's property problem.
Currently, the Preventing Countermeasures of red tide other than preventing seawater eutrophication, will also contain the i.e. red tide algae of red tide plankton
Development, and contain that the method for red tide algae development is mainly that chemical agent is administered.Although chemical agent such as copper sulphate, chlorine etc. is fast
Speed effectively kills or inhibits harmful algae or inhibits its growth and breeding, but in the presence of the harm to non-red tide plankton, medicament residue
And the secondary pollution problems to environment.Compared with administering chemical agent traditional used in red tide, marine organisms source day
So drug has the advantages that with strong points, highly-safe, active significant and environmentally friendly, to solve to be caused by red tide algae at present
The prevention and treatment problem of red tide provide new thinking
Summary of the invention
The object of the present invention is to provide a kind of ring flores aurantii alkane acylated derivatives and its preparations and application.
To achieve the above object, the technical solution adopted by the present invention are as follows:
A kind of ring flores aurantii alkane acylated derivatives, shown in the structure such as formula (I) of ring flores aurantii alkane acylated derivatives
A kind of preparation method of ring flores aurantii alkane acylated derivatives, by trichoderma asperellum (Trichoderma asperellum) A-
YMD-9-2 is inoculated in fermented and cultured in fungi culture medium, after tunning is purified, as ring flores aurantii alkane acyl shown in formula (I)
Change derivative；Trichoderma asperellum (Trichoderma asperellum) A-YMD-9-2 was saved on June 27th, 2018
In China typical culture collection center CCTCC, deposit number is CCTCC NO:M 2018405.
Specifically:
1) trichoderma asperellum (Trichoderma asperellum) A-YMD-9-2 is inoculated in fungi culture medium and is fermented
10-60 days, and after extract and be concentrated 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 through eluent, collect elution fraction,
Elution fraction is detected through thin-layer chromatography；
3) collection step 2) in elution fraction successively inverted silica gel column chromatography, gel filtration chromatography and prepare thin-layer chromatography again
It isolates and purifies to get the ring flores aurantii alkane acylated derivatives as shown in formula (I).
Fungi culture medium is rice solid medium, jerusalem artichoke dextrose broth or potato glucose in step 1)
Fluid nutrient medium.
Organic solvent is ethyl acetate, petroleum ether, n-hexane, hexamethylene, methylene chloride, methanol, ethyl alcohol, propyl alcohol or isopropyl
It is one or more of in alcohol.
Petroleum ether-ethyl acetate, the petroleum ether-ethyl alcohol, petroleum ether-that eluent in step 2) is volume ratio 50-0:1
Propyl alcohol, petroleum ether-isopropanol, dichloromethane-ethyl acetate, methylene chloride-methanol, dichloromethane-ethanol, methylene chloride-the third
One group in alcohol, methylene chloride-isopropanol or several groups.
Step 3) the reversed-phase silica gel column chromatography eluent is the water-methanol or water-ethanol of volume ratio 5-0:1；Gel column
Chromatographic eluate is the methylene chloride-methanol or methylene chloride-ethyl alcohol of volume ratio 2-0:1；Preparing thin-layer chromatography eluent is body
Methylene chloride-methanol or petroleum ether-ethyl alcohol of the product than 20-0:1.
A kind of application of ring flores aurantii alkane acylated derivatives, the ring flores aurantii alkane acylated derivatives are used to prepare the suppression of microalgae
Algae agent.
The microalgae is the Heterosigma akashiwo for causing red tide to endanger.
The invention has the following advantages that the present invention is by being located away from the trichoderma asperellum of marine red alga fragrant plant mentioned in ancient texts
(Trichoderma asperellum) A-YMD-9-2 ferment it is extracted, separation obtain ring flores aurantii alkane acylated derivatives, through pressing down
Activity of microalgae experiment processed show that compound is 5.2 mcg/mls to the half-inhibitory concentration for the Heterosigma akashiwo that can cause red tide.
Specific embodiment:
The present invention is further elaborated below with reference to embodiment.
Embodiment 1
Shown in the structure such as formula (I) of the ring flores aurantii alkane acylated derivatives in seaweed endogenetic fungus source.
The compound has following physical and chemical and spectral characteristic:
Colorless oil；Specific rotatory power [α]20 D-13(c 2.6,MeOH)；Nuclear magnetic resonance spectroscopy (solvent is deuterated chloroform) δH
1.03d(6.8),1.14s,1.25s,1.47m,1.53m,1.55 m,1.56m,1.58m,1.67m,1.74s,1.76m,
1.83m,1.84m,2.04 s,2.17d(1.1),2.41t(6.8),4.20t(6.8),4.42td(8.1,5.8), 4.87s,
4.90s,5.55br d(8.6),5.59br s；Carbon-13 nmr spectra (solvent is deuterated chloroform) δC 14.6CH3,18.5CH3,
19.8CH3,21.1CH3,25.0CH3,24.5 CH2,26.2CH3,27.7CH2,36.3CH2,39.6CH2,40.5CH2,44.4CH,
54.3 CH,54.7CH,62.2CH2,81.4C,74.7C,111.7CH2,120.2CH,144.9 C,150.0C,166.2C,
171.2C；High resolution mass spectrum [M]+M/z 409.2821, calculated value 409.2828.
Embodiment 2
The preparation method of ring flores aurantii alkane acylated derivatives as shown in formula (I):
It makes even well-grown trichoderma asperellum (Trichoderma asperellum) A-YMD-9-2 strain on plate, is cut into
Fritter is simultaneously inoculated in rice solid medium, puts 50 grams of rice solid mediums in every 1 liter of triangular flask, totally 200 bottles, room temperature is quiet
It only ferments 40 days, is then extracted with ethyl acetate three times, is concentrated under reduced pressure, 212.4 grams of crude extract are obtained after concentration.
The rice solid medium group become every liter contain 500 grams of rice, 6 grams of peptone, 500 milliliters of distilled water, Chen Hai
500 milliliters of water.
During trichoderma asperellum (Trichoderma asperellum) A-YMD-9-2 strain was stored on June 27th, 2018
State Type Tissue Collection CCTCC, address: Wuhan, China university, deposit number are CCTCC NO:M 2018405, classification
It is named as Trichoderma asperellum, strain number is A-YMD-9-2.
Silica gel column chromatography by crude extract through 100-200 mesh, successively with volume ratio 50:1,20:1,10:1,5:1,2:1,
The petroleum ether-ethyl acetate and 10:1,5:1 of 1:1 to 0:1,2:1,1:1 to 0:1 methylene chloride-methanol carry out gradient elution,
Eluent is collected respectively, and each component of collection uses thin-layer chromatography (TLC) to detect (methylene chloride-methanol of volume ratio 50-1:1 again
Expansion, anisaldehyde-sulfuric acid colour developing or the ultraviolet light detection of 254nm), judged according to Rf value, merge same or like part, obtained
8 components (1-8).
It is the component of 0.5-0.7 (methylene chloride-methanol of volume ratio 15:1 is unfolded, the ultraviolet light detection of 254nm) by Rf value
4, i.e., with the successively inverted C again of the component under the petroleum ether-ethyl acetate gradient elution of volume ratio 1:118Silicagel column, Sephadex
LH-20 gel column is separated with thin-layer chromatography is prepared.Reverse phase C18Silica gel column chromatography eluent is the water-methanol of volume ratio 1:1, TLC
Detection (methylene chloride-methanol of volume ratio 15:1 is unfolded, the ultraviolet light detection of 254nm, anisaldehyde-sulfuric acid colour developing), collects 254nm
There are fluorescence, anisaldehyde-sulfuric acid to show red component under ultraviolet light；Component is collected again through Sephadex LH-20 gel filtration chromatography,
Eluent is methanol, and (methylene chloride-methanol of volume ratio 15:1 is unfolded, the ultraviolet light detection of 254nm, anisaldehyde-sulphur for TLC detection
Acid colour developing), collecting has fluorescence, anisaldehyde-sulfuric acid to show red component under 254nm ultraviolet light；Collection group lease making prepares thin layer
Analysis, eluent are the methylene chloride-methanol of volume ratio 15:1, and collecting has fluorescence and Rf value for 0.5-0.6 under 254nm ultraviolet light
Component, as compound shown in formula (I) (52.0 milligrams).(volume ratio 15:1 methylene chloride-methanol exhibition is detected through thin-layer chromatography
Open, the ultraviolet light detection of 254nm, anisaldehyde-sulfuric acid colour developing), in single, uniform fluorescence, aobvious punctation, it is determined as purifying and closes
Object.Through Spectrum Analysis, Structural Identification is a kind of ring flores aurantii alkane acylated derivatives, and structural formula is such as shown in (I).
Embodiment 3
Difference from Example 2 is
It makes even well-grown trichoderma asperellum (Trichoderma asperellum) A-YMD-9-2 strain on plate, is cut into
Fritter is simultaneously inoculated in jerusalem artichoke dextrose broth, puts 300 milliliters of culture mediums in every 1 liter of triangular flask, and totally 200 bottles, room temperature
Static fermentation 40 days is then extracted three times with methylene chloride, is concentrated under reduced pressure, 200 grams of crude extract are 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, grape
20 grams, 5 grams of peptone, 500 milliliters of Chen Haishui of sugar.
Silica gel column chromatography by crude extract through 200-300 mesh, successively with volume ratio 50:1,30:1,15:1,10:1,5:1,
Petroleum ether-ethyl alcohol progress gradient elution of 2:1,1:1 to 0:1, collect eluent, then detect (volume ratio with thin-layer chromatography respectively
The petroleum ether of 50-0:1-ethyl alcohol expansion, anisaldehyde-sulfuric acid colour developing or the ultraviolet light detection of 254nm), judged according to Rf value, merged
Same or like part obtains 8 components (1-8).
It is 0.5-0.7 (petroleum ether of volume ratio 10:1-ethyl alcohol expansion, the ultraviolet light detection of 254nm, anisaldehyde-sulphur by Rf value
Acid colour developing) component 4, i.e., with the successively inverted C again of the component under petroleum ether-ethanol gradient elution of volume ratio 10:118Silica gel
Column, Sephadex LH-20 gel column and prepare thin-layer chromatography separation.Reverse phase C18Silica gel column chromatography eluent is volume ratio 3:2's
Water-ethanol, (petroleum ether of volume ratio 10:1-ethyl alcohol expansion, the ultraviolet light detection of 254nm, anisaldehyde-sulfuric acid are aobvious for TLC detection
Color), collecting has fluorescence, anisaldehyde-sulfuric acid to show red component under 254nm ultraviolet light；Component is collected again through Sephadex LH-
20 gel filtration chromatographies, eluent are ethyl alcohol, TLC detection (petroleum ether of volume ratio 10:1-ethyl alcohol expansion, the inspection of 254nm ultraviolet light
Survey, anisaldehyde-sulfuric acid colour developing), collecting has fluorescence, anisaldehyde-sulfuric acid to show red component under 254nm ultraviolet light；Collect component
Thin-layer chromatography is prepared, petroleum ether-ethyl alcohol of volume ratio 10:1 is solvent, and collecting under 254nm ultraviolet light has fluorescence and Rf value
For the component of 0.5-0.6, ring flores aurantii alkane acylated derivatives shown in formula (I) are obtained.
Embodiment 4
Press down activity of microalgae experiment:
Specifically: activation is diluted to certain for trying microalgae, the microalgae of logarithmic growth phase with sterilized f/2 culture medium
Frustule concentration (about 5 × 104A/milliliter), 96 orifice plates are taken, every hole adds 195 microlitres of algae solutions to be test cultures plate.Sample sets and
Control group respectively sets three in parallel, and sample sets add 5 microlitres of concentration to be the compound solution of 4 mg/mls, and solvent is dimethyl sulfoxide
(DMSO), blank control group adds 5 microlitres of solvents, and positive controls add 5 microlitres of concentration to be the K of 4 mg/mls2Cr2O7Solution.
Under the conditions of 20 DEG C of cultivation temperature, intensity of illumination 2000Lux, Light To Dark Ratio 14:10 (hour), cultivate 24 hours.Wherein for trying microalgae
For Heterosigma akashiwo.
Using blood counting chamber, microalgae in each experimental group is counted under the microscope.To inhibiting rate greater than 50%
Experimental group further calculates its half-inhibitory concentration IC50Value.By the compound solution of configured final concentration of 4 mg/ml
Successively be diluted, finally obtain component that 15 groups of concentration successively reduce (1000,500,200,100,50,20,10,5,2,1,
0.5,0.25,0.125,0.0625,0.03125 mcg/ml).Observe and calculate the microalgae suppression of compound under each concentration gradient
Rate processed takes inhibiting rate at least five concentration gradient between 0-100, calculates IC50Value.
Experimental result: the ring flores aurantii alkane acylated derivatives of above-mentioned acquisition are 5.2 to the half-inhibitory concentration of Heterosigma akashiwo
Mcg/ml has the function of inhibiting Heterosigma akashiwo.
Claims (8)
1. a kind of ring flores aurantii alkane acylated derivatives, it is characterised in that: shown in the structure such as formula (I) of ring flores aurantii alkane acylated derivatives
。
2. a kind of preparation method of ring flores aurantii alkane acylated derivatives described in claim 1, it is characterised in that: by trichoderma asperellum
(Trichoderma asperellum) A-YMD-9-2 is inoculated in fermented and cultured in fungi culture medium, after tunning is purified,
As ring flores aurantii alkane acylated derivatives shown in formula (I)；Described trichoderma asperellum (Trichoderma asperellum) A-
YMD-9-2 is stored in China typical culture collection center CCTCC on June 27th, 2018, and deposit number is CCTCC NO:M
2018405。
。
3. the preparation method of ring flores aurantii alkane acylated derivatives as described in claim 2, it is characterised in that specific preparation step:
1) trichoderma asperellum (Trichoderma asperellum) A-YMD-9-2 is inoculated in fungi culture medium the 10-60 that ferments
It, and after extract and be concentrated 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 through eluent, collect elution fraction, elution
Group lease making thin-layer chromatography detection；
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 ring flores aurantii alkane acylated derivatives as shown in formula (I).
4. the preparation method of ring flores aurantii alkane acylated derivatives according to claim 3, it is characterised in that: fungi is trained in step 1)
Supporting base is rice solid medium, jerusalem artichoke dextrose broth or potato dextrose broth；
Organic solvent is in ethyl acetate, petroleum ether, n-hexane, hexamethylene, methylene chloride, methanol, ethyl alcohol, propyl alcohol or isopropanol
It is one or more of.
5. the preparation method of ring flores aurantii alkane acylated derivatives according to claim 3, it is characterised in that: the elution in step 2)
Liquid is petroleum ether-ethyl acetate, petroleum ether-ethyl alcohol, petroleum ether-propyl alcohol, the petroleum ether-isopropanol, dichloro of volume ratio 50-0:1
Methane-ethyl acetate, methylene chloride-methanol, dichloromethane-ethanol, methylene chloride-propyl alcohol, one in methylene chloride-isopropanol
Group or several groups.
6. the preparation method of ring flores aurantii alkane acylated derivatives according to claim 3, it is characterised in that: the step 3) reverse phase
Silica gel column chromatography eluent is the water-methanol or water-ethanol of volume ratio 5-0:1；Gel filtration chromatography eluent is volume ratio 2-0:1
Methylene chloride-methanol or dichloromethane-ethanol；Prepare methylene chloride-first that thin-layer chromatography eluent is volume ratio 20-0:1
Alcohol or petroleum ether-ethyl alcohol.
7. a kind of application of ring flores aurantii alkane acylated derivatives described in claim 1, it is characterised in that: the ring flores aurantii alkane acyl
Change the algae-inhibiting agent that derivative is used to prepare microalgae.
8. the application of ring flores aurantii alkane acylated derivatives according to claim 7, it is characterised in that: the microalgae is to cause red tide
The Heterosigma akashiwo of harm.
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| CN110003041B (en) | 2021-09-28 |
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