CN108467337A - A kind of sesquiterpene alcohols compound and its preparation and application - Google Patents
A kind of sesquiterpene alcohols compound and its preparation and application Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/34—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (5.3.0.) system, e.g. azulenols
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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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
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- 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
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/30—Azulenes; Hydrogenated azulenes
Abstract
The present invention relates to algae-inhibiting agent fields, specifically the sesquiterpene alcohols compound 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 sesquiterpene alcohols compound shown in formula (I).The sesquiterpene alcohols compound that the present invention obtains obtains compound to the half-inhibition concentration of microalgae up to 1.2 mcg/mls through pressing down activity of microalgae experiment.
Description
Technical field
The present invention relates to algae-inhibiting agent fields, the specifically a kind of sesquiterpene alcohols chemical combination in seaweed epiphytic fungi source
Object 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 sharpens, 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 sesquiterpene alcohols compound and its preparations and application.
To achieve the above object, the technical solution adopted by the present invention is：
A kind of sesquiterpene alcohols compound, shown in sesquiterpene alcohols compound structure such as formula (I)
A kind of preparation method of sesquiterpene alcohols compound meets green trichoderma (Trichoderma virens) Y13-3
The fermented and cultured kind in fungi culture medium, after tunning is purified, as sesquiterpene alcohols compound shown in formula (I)；
Green trichoderma (Trichoderma virens) Y13-3 was stored in China typical culture collection on January 10th, 2018
Center 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, then
It extracts and concentrates 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 again successively inverted silica gel column chromatography, gel filtration chromatography and thin-layer chromatography separation
Purifying is to get the sesquiterpene alcohols compound 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 petroleum ether-ethyl acetate, petroleum ether-ethyl alcohol, the stone of volume ratio 50-0: 1
Oily ether-propyl alcohol, petroleum ether-isopropanol, dichloromethane-ethyl acetate, methylene chloride-methanol, dichloromethane-ethanol, dichloromethane
One group or several groups of alkane-propyl alcohol, dichloromethane-isopropanol.
Step 3) the reversed-phase silica gel column chromatography eluent is the water-methanol or water-ethanol of volume ratio 5-0: 1；It is solidifying
Plastic column chromatography eluent is the methylene chloride-methanol or dichloromethane-ethanol of volume ratio 2-0: 1；Thin-layer chromatography solvent is body
Product is than petroleum ether-ethyl acetate, petroleum ether-ethyl alcohol or the dichloromethane-ethyl acetate for 10-0: 1.
The step 3) detects after respectively chromatographing through TLC, collects the component of punctation.
A kind of application of sesquiterpene alcohols compound, the sesquiterpene alcohols compound are being used to prepare microalgae
Application in algae-inhibiting agent.
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 ferments the sesquiterpene alcohols compound that extracted, separation obtains, and inhibited microalgae is lived
Property experiment obtain compound to the Phaeocystis globosa of red tide, Prorocentrum donghaiense, Heterosigma akashiwo and hypertoxic karr algae can be caused
Half-inhibition concentration is respectively 1.2,6.5,6.2 and 12.1 mcg/mls.
Specific implementation mode：
The present invention is further elaborated with reference to embodiment.
Embodiment 1
Shown in the sesquiterpene alcohols compound 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- 29 (c0.13, MeOH)；Nuclear magnetic resonance spectroscopy (solvent is deuterochloroform) δH1.69 (dd, 14.1,8.1), 1.61 (dd, 14.2,3.3), 4.03 (dd, 8.2,3.3), 1.56 (dd, 11.2,1.4), 1.68
(m), 1.57 (m), 2.29 (m), 4.20 (dd, 10.2,5.7), 2.10 (dd, 12.7,5.7), 1.20 (dd, 12.6,10.5),
1.76 (heptet, 6.9), 0.96 (d, 6.9), 0.86 (d, 6.9), 5.11 (br s), 4.91 (br s), 1.16 (s)；Nuclear-magnetism
The carbon that resonates composes (solvent is deuterochloroform) δC41.3 (C), 51.0 (CH2), 72.6 (CH), 84.0 (C), 52.1 (CH), 22.3
(CH2), 31.6 (CH2), 153.7 (C), 73.2 (CH), 51.7 (CH2), 35.1 (CH), 17.3 (CH3), 17.8 (CH3), 111.9
(CH2), 22.4 (CH3)；High resolution mass spectrum [M]+M/z 254.1889, calculated value 254.1882.
Embodiment 2
The preparation method of sesquiterpene alcohols compound 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 grams, 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: 1,20 successively:
1,10: 1,5: 1,2: 1 to 1: 1 and the gradient of methylene chloride-methanol 20: 1,10: 1,5: 1 to 1: 1 eluted, collect respectively
Eluent, then (petroleum ether-ethyl acetate of volume ratio 20-0: 1 is unfolded, and anisaldehyde-sulfuric acid is made with thin-layer chromatography (TLC) detection
For color developing agent), judge, merge same or like part according to Rf values, obtains 10 components (1-10).
It is 0.4-0.5 (ethyl acetate is unfolded, the colour developing of sulfuric acid-anisaldehyde) component 6 i.e. with the oil of volume ratio 1: 1 by Rf values
Component under ether-ethyl acetate gradient inverted C successively again18Silicagel column, SephadexLH-20 gel columns and thin-layer chromatography
Separation.Reverse phase C18Silica gel column chromatography eluent is the water-methanol of volume ratio 1: 1, and (ethyl acetate is unfolded, sulfuric acid-fennel for TLC detections
Fragrant aldehyde colour developing), collect the component of punctation；Eluent is first when collection group lease making Sephadex LH-20 gel filtration chromatographies
Alcohol, TLC detections (ethyl acetate is unfolded, sulfuric acid-anisaldehyde colour developing), collects the component of punctation；Collection group lease making prepares thin
It analyses layer by layer, the petroleum ether-ethyl acetate of volume ratio 1: 1 is solvent, collects the component that Rf values are 0.4-0.5, as formula (I) institute
Show compound (5.4 milligrams), is in single, uniform red grouper through TLC detections (ethyl acetate is unfolded, sulfuric acid-anisaldehyde colour developing)
Point, is determined as pure compound.Through Spectrum Analysis, Structural Identification is a kind of new sesquiterpene alcohols compound, 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 (20-0: 1 petroleum ether-ethyl acetate exhibition of volume ratio through thin-layer chromatography (TLC)
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: 1,30: 1,15 successively
: 1,10: 1,5: 1,2: 1,1: 1 to 0: 1 gradient is eluted, and collects eluent respectively, then detect (volume ratio with thin-layer chromatography
20-0: 1 petroleum ether-ethyl acetate expansion, sulfuric acid-anisaldehyde colour developing), judge, merge same or like portion according to Rf values
Point, obtain 8 components (1-8).
By the component 4 of Rf values=0.4-0.5 (ethyl acetate is unfolded, sulfuric acid-anisaldehyde colour developing) i.e. with volume ratio 10: 1
Component under petroleum ether-ethanol gradient elution inverted C successively again18Silicagel column, Sephadex LH-20 gel columns and thin layer
Analysis separation.Reverse phase C18Silica gel column chromatography eluent is the water-ethanol of volume ratio 1: 1, and (ethyl acetate is unfolded, sulfuric acid-for TLC detections
Anisaldehyde develops the color), collect the component of punctation；Eluent is second when collection group lease making Sephadex LH-20 gel filtration chromatographies
Alcohol, TLC detections (ethyl acetate is unfolded, sulfuric acid-anisaldehyde colour developing), collects the component of punctation；Collection group lease making prepares thin
It analyses layer by layer, petroleum ether-ethyl alcohol of volume ratio 8: 1 is solvent, collects the component that Rf values are 0.4-0.5, obtains sesquialter shown in formula (I)
Terpene alcohols compound.
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, under the conditions of Light To Dark Ratio 14: 10 (hour), 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, then inhibiting rate is more than
50% experimental group further calculates its half-inhibition concentration IC50Value.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 sesquiterpene alcohols compound of above-mentioned acquisition is different curved to Phaeocystis globosa, Prorocentrum donghaiense, red tide
The half-inhibition concentration of algae and hypertoxic karr algae be respectively 1.2 mcg/mls, 6.5 mcg/mls, 6.2 mcg/mls and
12.1 mcg/mls have the function of inhibiting Phaeocystis globosa, Prorocentrum donghaiense, Heterosigma akashiwo or hypertoxic karr algae.
Claims (8)
1. a kind of sesquiterpene alcohols compound, it is characterised in that：Shown in sesquiterpene alcohols compound structure such as formula (I)
2. a kind of preparation method of sesquiterpene alcohols compound 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) sesquiterpene alcohols compound shown in；Green trichoderma (Trichoderma virens) Y13-3 is in January, 2018
It is stored within 10th China typical culture collection center CCTCC, deposit number is CCTCC NO:M 2018016；
3. the preparation method of sesquiterpene alcohols compound as described in claim 2, it is characterised in that specific preparation process：
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 sesquiterpene alcohols compound as shown in formula (I).
4. the preparation method of sesquiterpene alcohols compound as described in claim 3, it is characterised in that：Fungi is trained in step 1)
It is potato dextrose broth, rice solid medium, malt extract medium or jerusalem artichoke liquid of glucose culture to support base
Base；
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 sesquiterpene alcohols compound as described in claim 3, it is characterised in that：It is organic in step 2)
Solvent is the petroleum ether-ethyl acetate of volume ratio 50-0: 1, petroleum ether-ethyl alcohol, petroleum ether-propyl alcohol, petroleum ether-isopropanol, two
Chloromethanes-ethyl acetate, methylene chloride-methanol, dichloromethane-ethanol, dichloromethane-propyl alcohol, one group of dichloromethane-isopropanol
Or several groups.
6. the preparation method of sesquiterpene alcohols compound as described in claim 3, it is characterised in that：Step 3) the 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；Thin-layer chromatography solvent is petroleum ether-acetic acid second that volume ratio is 10-0: 1
Ester, petroleum ether-ethyl alcohol or dichloromethane-ethyl acetate.
7. a kind of application of sesquiterpene alcohols compound described in claim 1 it is characterized in that：The sesquiterpene alcohols
Application of the class compound in the algae-inhibiting agent for being used to prepare microalgae.
8. the application of sesquiterpene alcohols compound as described in claim 7, it is characterised in that：The microalgae is to cause ocean
Phaeocystis globosa, Prorocentrum donghaiense, Heterosigma akashiwo or the hypertoxic karr algae of red tide.
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| CN109503535A (en) * | 2019-01-04 | 2019-03-22 | 中国科学院烟台海岸带研究所 | A kind of bicyclic ring flores aurantii alkane type sesquiterpene derivative and its preparation and application |
| CN109503413A (en) * | 2019-01-04 | 2019-03-22 | 中国科学院烟台海岸带研究所 | A kind of monocycle ring flores aurantii alkane type sesquiterpene derivative and its preparation and application |
| CN109503414A (en) * | 2019-01-04 | 2019-03-22 | 中国科学院烟台海岸带研究所 | One kind alkane type sesquiterpene derivative of flores aurantii containing azo-cycle and its preparation and application |
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| CN111606878A (en) * | 2020-05-25 | 2020-09-01 | 中国科学院烟台海岸带研究所 | Cadinane derivative and preparation and application thereof |
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