CN108383707A - A kind of daucane sesquiterpenoids and its preparation and application - Google Patents
A kind of daucane sesquiterpenoids and its preparation and application Download PDFInfo
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- CN108383707A CN108383707A CN201810367063.9A CN201810367063A CN108383707A CN 108383707 A CN108383707 A CN 108383707A CN 201810367063 A CN201810367063 A CN 201810367063A CN 108383707 A CN108383707 A CN 108383707A
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Abstract
The present invention relates to algae-inhibiting agent fields, specifically the daucane sesquiterpenoids in a kind of seaweed epiphytic fungi source and preparation method thereof and the application in terms of inhibiting microalgae.Concrete structure formula is such as shown in (I), preparation method is that seaweed epiphytic fungi green trichoderma (Trichoderma virens) Y13 3 is inoculated in fermented and cultured in fungi culture medium, tunning is after isolating and purifying, as daucane sesquiterpenoids shown in formula (I).The daucane sesquiterpenoids that the present invention obtains obtains compound to the half-inhibition concentration of microalgae up to 0.24 mcg/ml through pressing down activity of microalgae experiment.
Description
Technical field
The present invention relates to algae-inhibiting agent fields, the specifically a kind of daucane sesquiterpenoids in seaweed epiphytic fungi source
Compound and preparation method thereof and the application in terms of inhibiting microalgae.
Background technology
In world wide, coastal waters Disaster And Prevention Measures of Red Tides increasingly takes place frequently, and seriously hinders sea fishery, offshore tourism and marine economy
Development.China enters the red tide high-incidence season after 2000, and red tide occurrence frequency and the extent of injury obviously increase.The main danger of red tide
There are four types of evil forms, first, destroying marine ecology balance；Second is that destroying marine fishery resources；Third, endangering human health；Fourth,
Influence the development of marine tourism.According to statistics, the economic loss as caused by red tide is up to 1,000,000,000 yuan or more every year.It can draw in ocean
The microalgae of red tide is sent out there are about 300 kinds, wherein about 80 kinds of toxic red tide algae.Scientificlly and effectively prevent and administer red tide to be the world today
One of 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 it is mainly that chemical agent is administered to contain the method for red tide algae development.Although chemical agent such as copper sulphate, chlorine etc. is fast
Speed effectively kills or inhibits harmful algae or inhibits growth 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 the traditional chemical agent used in red tide, marine organisms source natural drug have it is with strong points,
Safe, active notable and environmentally friendly advantage, to solve the problems, such as that the prevention of the red tide caused at present by red tide algae carries
New thinking is supplied.
Invention content
The object of the present invention is to provide a kind of daucane sesquiterpenoids and its preparations and application.
To achieve the above object, the technical solution adopted by the present invention is：
A kind of daucane sesquiterpenoids, shown in daucane sesquiterpenoids structure such as formula (I)
A kind of preparation method of daucane sesquiterpenoids, by green trichoderma (Trichoderma virens) Y13-3
It is inoculated in fermented and cultured in fungi culture medium, after tunning is purified, as daucane sesquiterpenoids shown in formula (I)
Close object；Green trichoderma (Trichoderma virens) Y13-3 was stored in Chinese Typical Representative culture on January 10th, 2018
Object collection CCTCC, deposit number are CCTCC NO:M 2018016；
Specific preparation process：
1) green trichoderma (Trichoderma virens) Y13-3 is inoculated in fungi culture medium and is fermented 10-60 days, and
It extracts and concentrates by 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 again successively inverted silica gel column chromatography, gel filtration chromatography and thin-layer chromatography separation
Purifying is to get the daucane sesquiterpenoids as shown in formula (I).
Fungi culture medium is potato dextrose broth, rice solid medium, brewer's wort in the step 1)
Culture medium or jerusalem artichoke dextrose broth；Preferably：Potato dextrose broth.
Organic solvent extracting solution is one or more of in dichloromethane, ethyl acetate, methanol, ethyl alcohol, propyl alcohol or isopropanol；
Preferably：Ethyl acetate.
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-ethyl alcohol；Thin-layer chromatography solvent is body
Product is than being 10-0:1 petroleum ether-ethyl acetate, petroleum ether-ethyl alcohol or dichloromethane-ethyl acetate.
The step 3) detects after respectively chromatographing through TLC, collects the component of punctation.
A kind of application of daucane sesquiterpenoids, the daucane sesquiterpenoids are being used to prepare
Application in the algae-inhibiting agent of microalgae.
The microalgae is the Phaeocystis globosa for causing marine red tide, Prorocentrum donghaiense, Heterosigma akashiwo or hypertoxic karr algae.
The present invention has the following advantages：The present invention is by being located away from the green trichoderma on marine red alga gracilaria asiatica surface
(Trichoderma virens) Y13-3 ferment it is extracted, separation obtain daucane sesquiterpenoids, it is inhibited micro-
Algae activity experiment obtains compound to that can cause the Phaeocystis globosa of red tide, Prorocentrum donghaiense, Heterosigma akashiwo and hypertoxic karr
The half-inhibition concentration of algae is respectively 0.24,3.8,3.1 and 5.2 mcg/mls.
Specific implementation mode：
The present invention is further elaborated with reference to embodiment.
Embodiment 1
Shown in the daucane sesquiterpenoids structure in seaweed epiphytic fungi source such as formula (I).
The compound has following physics and chemistry and spectral characteristic：
Colorless oil；Specific rotatory power [α]20 D–114(c 0.13,MeOH)；Nuclear magnetic resonance spectroscopy (solvent is deuterochloroform)
δH 2.29(d,16.1),2.25(d,16.1),2.41(dd,12.0, 3.7),2.61(m),2.51(dddd,20.1,7.1,
3.7,0.9),6.43(dq,7.1,1.4), 2.84(d,15.7),2.64(d,15.9),1.78(heptet,6.9),0.97(d,
6.9), 0.91(d,6.8),1.89(br s),1.02(s)；Carbon-13 nmr spectra (solvent is deuterochloroform) δC 36.4(C),
54.1(CH2),218.5(C),81.2(C),48.6(CH),28.4(CH2), 139.3(CH),137.3(C),201.3(C),
57.8(CH2),36.7(CH),16.8(CH3), 17.2(CH3),22.2(CH3),20.2(CH3)；High resolution mass spectrum [M]+m/z
250.1570 calculated value 250.1569.
Embodiment 2
The preparation method of daucane sesquiterpenoids as shown in formula (I)：
It makes even well-grown green trichoderma (Trichoderma virens) Y13-3 strains on plate, is cut into small pieces and is inoculated with
In potato dextrose broth, 300 milliliters of culture mediums are put in every 1 liter of triangular flask, totally 200 bottles, the static fermentation of room temperature
It 30 days, is then extracted with ethyl acetate three times, is concentrated under reduced pressure, 27.2 grams of crude extract is obtained after concentration.
The potato dextrose broth group becomes every liter of 500 milliliters of liquor for containing 100 grams of potatoes, glucose 20
Gram, 5 grams of peptone, 5 grams of yeast extract, 500 milliliters of Chen Haishui.
Green trichoderma (Trichoderma virens) Y13-3 strains were stored in Chinese Typical Representative culture on January 10th, 2018
Object collection CCTCC, address：Wuhan, China university, deposit number are CCTCC NO:M 2018016, Classification And Nomenclature are
Trichoderma virens, strain number are Y13-3.
By silica gel column chromatography of the crude extract through 200-300 mesh, use petroleum ether-ethyl acetate with volume ratio 50 successively:1、20:
1、10:1、5:1、2:1 to 1:1 and methylene chloride-methanol 20:1、10:1、5:1 to 1:1 gradient is eluted, and is collected respectively
The each component of eluent, collection uses thin-layer chromatography (TLC) to detect (volume ratio 20-0 again：1 petroleum ether-ethyl acetate expansion,
Anisaldehyde-sulfuric acid is as color developing agent), judge, merge same or like part according to Rf values, obtains 10 components (1-10).
It is 0.6-0.7 (volume ratios 1 by Rf values:1 petroleum ether-ethyl acetate expansion, the colour developing of sulfuric acid-anisaldehyde) component
5, i.e., with volume ratio 2:Component under 1 petroleum ether-ethyl acetate gradient elution inverted C successively again18Silicagel column, Sephadex
LH-20 gel columns and thin-layer chromatography separation.Reverse phase C18Silica gel column chromatography eluent is volume ratio 1:1 water-methanol, TLC detections
(volume ratio 1:1 petroleum ether-ethyl acetate expansion, sulfuric acid-anisaldehyde colour developing), collect the component of punctation；Collect component
It is methanol through eluent when Sephadex LH-20 gel filtration chromatographies, TLC detects (volume ratio 1:1 petroleum ether-ethyl acetate exhibition
Open, sulfuric acid-anisaldehyde colour developing), collect the component of punctation；Collection group lease making prepares thin-layer chromatography, volume ratio 1:1 oil
Ether-ethyl acetate is solvent, collects the component that Rf values are 0.6-0.7, as compound (6.2 milligrams) shown in formula (I), warp
TLC detects (volume ratio 1:1 petroleum ether-ethyl acetate expansion, sulfuric acid-anisaldehyde colour developing), it is in single, uniform punctation,
It is determined as pure compound.Through Spectrum Analysis, Structural Identification is a kind of new daucane sesquiterpenoids, and structural formula is such as
(I) shown in.
Embodiment 3
Difference from Example 2 is
It makes even well-grown green trichoderma (Trichoderma virens) Y13-3 strains on plate, is cut into small pieces and is inoculated with
In jerusalem artichoke dextrose broth, 300 milliliters of culture mediums are put in every 1 liter of triangular flask, totally 100 bottles, room temperature it is static fermentation 40
It, filters and collects mycelium and zymotic fluid respectively.
The jerusalem artichoke dextrose broth group becomes every liter of 500 milliliters of liquor for containing 100 grams of jerusalem artichoke stem tubers, grape
20 grams of sugar, 5 grams of peptone, 5 grams of yeast extract, 500 milliliters of Chen Haishui.
About 30 liters of zymotic fluid is collected, is extracted with ethyl acetate three times, is concentrated under reduced pressure；Acetic acid is used after mycelium drying and crushing
Ethyl ester extracts three times, is concentrated under reduced pressure；Concentrate detects (volume ratio 20-0 through thin-layer chromatography (TLC)：1 petroleum ether-ethyl acetate exhibition
Open, the colour developing of sulfuric acid-anisaldehyde) its result is similar, and it is 18.0 grams of crude extract to merge zymotic fluid and the two-part concentrate of mycelium.
By silica gel column chromatography of the crude extract through 200-300 mesh, use petroleum ether-ethyl alcohol with volume ratio 50 successively:1、30:1、
15:1、10:1、5:1、2:1、1:1 to 0:1 gradient is eluted, and collects eluent respectively, then detect (volume with thin-layer chromatography
Compare 20-0：1 petroleum ether-ethyl acetate expansion, sulfuric acid-anisaldehyde colour developing), it is same or like to judge, merge according to Rf values
Part obtains 8 components (1-8).
It is 0.6-0.7 (volume ratios 1 by Rf values:1 petroleum ether-ethyl acetate expansion, the colour developing of sulfuric acid-anisaldehyde) 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 columns and thin-layer chromatography separation.Reverse phase C18Silica gel column chromatography eluent is volume ratio 1:1 water-ethanol, TLC detect (body
Product ratio 1:1 petroleum ether-ethyl acetate expansion, sulfuric acid-anisaldehyde colour developing), collect the component of punctation；Collection group lease making
Eluent is ethyl alcohol when Sephadex LH-20 gel filtration chromatographies, and TLC detects (volume ratio 1:1 petroleum ether-ethyl acetate exhibition
Open, sulfuric acid-anisaldehyde colour developing), collect the component of punctation；Collection group lease making prepares thin-layer chromatography, volume ratio 10:1 stone
Oily ether-ethyl alcohol is solvent, collects the component that Rf values are 0.6-0.7, obtains daucane sesquiterpenoids shown in formula (I).
Embodiment 4
Press down activity of microalgae experiment：
Specially:Activation is diluted to certain for trying microalgae, the microalgae of logarithmic growth phase with sterilized f/2 culture mediums
Frustule concentration (about 5 × 104A/milliliter), 96 orifice plates are taken, it is test cultures plate that 95 microlitres of algae solutions are added per hole.Sample sets and
Control group respectively set three it is parallel, sample sets add 5 microlitres of dimethyl Asias of compound shown in the formula (I) containing a concentration of 4 mg/ml
Sulfone (DMSO) solution, blank control group add 5 microlitres of dimethyl sulfoxide (DMSO)s (DMSO), positive controls add 5 microlitres a concentration of 4 milligrams/
The K of milliliter2Cr2O7Solution.20 DEG C, intensity of illumination 2000Lux of cultivation temperature, Light To Dark Ratio 14:Under the conditions of 10 (hours), culture 24
Hour.It is wherein Phaeocystis globosa, Prorocentrum donghaiense, Heterosigma akashiwo or hypertoxic karr algae for examination microalgae.
Using blood counting chamber, microalgae in each experimental group is counted under the microscope；It is then that above-mentioned inhibiting rate is big
In 50% experimental group, its half-inhibition concentration IC is further calculated50Value.By the formula of final concentration of 4 mg/ml configured
(I) compound DMSO solution shown in is diluted through DMSO successively, finally obtain component that 11 groups of concentration reduce successively (2000,
1000,500,200,100,50,20,10,5,2,1 mcg/ml).Observe and calculate the microalgae of compound under each concentration gradient
Inhibiting rate takes inhibiting rate at least five concentration gradient between 0-100, calculates IC50Value.
Experimental result：The daucane sesquiterpenoids of above-mentioned acquisition is to Phaeocystis globosa, Prorocentrum donghaiense, red tide
The half-inhibition concentration of different curved algae and hypertoxic karr algae is respectively 0.24 mcg/ml, 3.8 mcg/mls, 3.1 micrograms/milli
Liter and 5.2 mcg/mls have the function of inhibiting Phaeocystis globosa, Prorocentrum donghaiense, Heterosigma akashiwo or hypertoxic karr algae.
Claims (8)
1. a kind of daucane sesquiterpenoids, it is characterised in that：Daucane sesquiterpenoids structure such as formula (I) institute
Show
2. a kind of preparation method of daucane sesquiterpenoids described in claim 1, it is characterised in that：By green trichoderma
(Trichoderma virens) Y13-3 is inoculated in fermented and cultured in fungi culture medium, after tunning is purified, as formula
(I) daucane sesquiterpenoids shown in；Described green trichoderma (Trichoderma virens) Y13-3 was in 2018 1
It is stored within 10th China typical culture collection center CCTCC the moons, deposit number is CCTCC NO: M 2018016；
3. the preparation method of daucane sesquiterpenoids as described in claim 2, it is characterised in that specific to prepare step
Suddenly：
1) green trichoderma (Trichoderma virens) Y13-3 is inoculated in fungi culture medium and is fermented 10-60 days, and after through having
Solvent is extracted and is concentrated, 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 thin-layer chromatography separation it is pure
Change to get the daucane sesquiterpenoids as shown in formula (I).
4. the preparation method of daucane sesquiterpenoids as described in claim 3, it is characterised in that：It is true in step 1)
Bacterium culture medium is potato dextrose broth, rice solid medium, malt extract medium or jerusalem artichoke liquid of glucose
Culture medium；
Organic solvent extracting solution is one or more of in dichloromethane, ethyl acetate, methanol, ethyl alcohol, propyl alcohol or isopropanol.
5. the preparation method of daucane sesquiterpenoids as described in claim 3, it is characterised in that：In step 2)
Organic solvent is volume ratio 50-0:1 petroleum ether-ethyl acetate, petroleum ether-ethyl alcohol, petroleum ether-propyl alcohol, petroleum ether-isopropyl
Alcohol, dichloromethane-ethyl acetate, methylene chloride-methanol, dichloromethane-ethanol, dichloromethane-propyl alcohol, dichloromethane-isopropyl
One group in alcohol or several groups.
6. the preparation method of daucane sesquiterpenoids as described in claim 3, it is characterised in that：Step 3) is described
Reversed-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；Thin-layer chromatography solvent is that volume ratio is 10-0:1 petroleum ether-second
Acetoacetic ester, petroleum ether-ethyl alcohol or dichloromethane-ethyl acetate.
7. a kind of application of daucane sesquiterpenoids described in claim 1, it is characterised in that：The daucane
Application of the sesquiterpenoids in the algae-inhibiting agent for being used to prepare microalgae.
8. the application of daucane sesquiterpenoids as described in claim 7, it is characterised in that：The microalgae is to cause
Phaeocystis globosa, Prorocentrum donghaiense, Heterosigma akashiwo or the hypertoxic karr algae of marine red tide.
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| CN111635316A (en) * | 2020-05-25 | 2020-09-08 | 中国科学院烟台海岸带研究所 | Chlorine-containing sesquiterpene derivative and preparation and application thereof |
| CN111662257A (en) * | 2020-05-25 | 2020-09-15 | 中国科学院烟台海岸带研究所 | Benzenedipine derivative and preparation and application thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232493A (en) * | 2018-11-14 | 2019-01-18 | 中国科学院海洋研究所 | A kind of sesquiterpenoid and its preparation method and application |
| CN109232493B (en) * | 2018-11-14 | 2022-08-16 | 中国科学院海洋研究所 | Sesquiterpene compound and preparation method and application thereof |
| CN111635316A (en) * | 2020-05-25 | 2020-09-08 | 中国科学院烟台海岸带研究所 | Chlorine-containing sesquiterpene derivative and preparation and application thereof |
| CN111662257A (en) * | 2020-05-25 | 2020-09-15 | 中国科学院烟台海岸带研究所 | Benzenedipine derivative and preparation and application thereof |
| CN111635316B (en) * | 2020-05-25 | 2022-09-30 | 中国科学院烟台海岸带研究所 | Chlorine-containing sesquiterpene derivative and preparation and application thereof |
| CN111662257B (en) * | 2020-05-25 | 2023-03-14 | 中国科学院烟台海岸带研究所 | Benzencadinane derivative, and preparation and application thereof |
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