CN106467528A - A kind of chloro different coumarin derivative and preparation method and application - Google Patents
A kind of chloro different coumarin derivative and preparation method and application Download PDFInfo
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Abstract
The present invention discloses a kind of chloro different coumarin derivative and preparation method and application, belongs to biological chemical field.The molecular formula of this derivant is C16H14Cl2O7, structural formula is as follows.The preparation method of this derivant is：First in bacterium culture medium, spawn culture is carried out to Myoporum bontiodes endogenetic fungus Trichoderma sp.09, then strain is carried out fermentation culture in fermentation medium, after gained mycelia ethanol water or methanol water mixed liquid extraction concentrating under reduced pressure, extracted with organic solvent；Extract carries out silica gel column chromatography, Sephdex LH 20 gel filtration chromatography after concentrating, and is recrystallized to give white crystal, as chloro different coumarin derivative after gained eluent is concentrated.Chloro different coumarin derivative of the present invention has the effect of very strong suppression Glorosprium musarum Cookeet Mass and Rhizoctonia solani Kuhn, can be used as microorganism disinfectant use in agriculture, and raw material can be had a extensive future with large-scale production.
Description
Technical field
The invention belongs to biological chemical field, it is related to a kind of chloro isocoumarin (chlorinated isocoumarin)
Derivant and preparation method and application, more particularly to a kind of to Glorosprium musarum Cookeet Mass (Colletotrichum musae) and
Rhizoctonia solani Kuhn (Rhizoctonia solani) has chloro different coumarin derivative and its preparation side of strong inhibitory activity
Method and application.
Background technology
Plant disease is always one of main restricting factor of crops good quality and high output, and according to statistics, the whole world is every year because of disease
The average loss of the farm output causing accounts for the 10%～15% of total output, and it is beautiful that annual direct economic loss is up to more than one hundred billion
Unit.The disease that plant pathogenic fungi causes accounts for the 70～80% of plant disease, some positions of their instruction plants, causes and withers
The ill symptomses such as listless, downright bad, rotten.Such as rice sheath blight disease makes Oryza sativa L. can not ear or the hollow kernels eared are more, and grain declines again,
It is one of Major Diseases in current Rice Production.Banana anthracnose makes brown maculeses on the fruit stem of banana and epidermis
Point, and cause whole fruit blackening to rot further, especially fall ill during storing and transporting the most serious, bring about great losses.Therefore,
The disinfectant use in agriculture preventing and treating fungal diseases of plants finding highly effective and safe has become maintenance higher yield of crops stable yields and agricultural product storage
The fresh-keeping problem being badly in need of solving.Plant endogenesis epiphyte colonizes in inside plants and does not cause obvious symptom to show its metabolite
Or low toxicity nontoxic to plant.Simultaneously because the difference of living environment is so as to have the uniqueness generation being different from other derived microbial
Thank to mode, the bioactive substance of novelty can be produced.However, so far, there is not yet the endogenetic fungus from plant origin
Middle acquisition has the use as antibacterial for the chloro isocumarans compound of important anti-fungal activity of plant pathogenic.
Content of the invention
In order to overcome shortcoming and the deficiency of prior art, the primary and foremost purpose of the present invention is to provide a kind of chloro isocoumarin
Derivant.
Another object of the present invention is to providing the preparation method of above-mentioned chloro different coumarin derivative.
It is still another object of the present invention to provide the application of above-mentioned chloro different coumarin derivative.
The purpose of the present invention is achieved through the following technical solutions：
A kind of chloro different coumarin derivative, its molecular formula is C16H14Cl2O7, structural formula is：
Described chloro different coumarin derivative is a kind of white, needle-shaped crystals, entitled
Dichlorodiaportinolide.
The preparation method of described chloro different coumarin derivative, comprises the following steps：First to hardship in bacterium culture medium
Sill indigo plant (Myoporum bontioides A.Gray) endogenetic fungus Trichoderma sp.09 carries out spawn culture, then by bacterium
Plant and carry out fermentation culture in fermentation medium, after gained mycelia alcohol-water or methanol-water mixture extraction concentrating under reduced pressure,
Extracted with organic solvent；Extract carries out silica gel column chromatography, Sephdex LH-20 gel filtration chromatography, by gained eluting after concentrating
Liquid is recrystallized to give white crystal after concentrating, as described chloro different coumarin derivative.
Preferably, described bacterium culture medium contains the component of following percetage by weight：Glucose 1.0～3.5%, yeast
Cream 0.02～1.5%, peptone 0.01～1.5%, agar 1.0～2.5%, sodium chloride 0.2～2.0% and water surplus；Use
When culture medium is made test tube slant.
It is furthermore preferred that described bacterium culture medium contains the component of following percetage by weight：Glucose 1.0～3.5%, ferment
Female cream 0.02～0.5%, peptone 0.1～1.5%, agar 1.0～1.5%, sodium chloride 0.2～2.0% and water surplus；
Preferably, the condition of described spawn culture is：Cultivate 3～10 days at 20～35 DEG C.More preferably at 28 DEG C
Lower culture 3～7 days.
Preferably, described fermentation medium contains the component of following percetage by weight：Rice 10.0～70.0%, chlorination
Calcium 0.3～2.5%, sodium chloride 1.0～5.5% and water surplus.
It is furthermore preferred that described fermentation medium contains the component of following percetage by weight：Rice 30.0～50.0%, chlorine
Change calcium 0.5～1.5%, sodium chloride 1.0～2.5% and water surplus.
Preferably, the condition of described fermentation culture is：Cultivate 30～80 days at 25～30 DEG C.More preferably 25～
Cultivate 30～60 days at 30 DEG C.
Preferably, the volume ratio of described alcohol-water or methanol-water mixture is 100：0～80：20；More preferably 95：
5～80：20.
The number of times of described extraction is 2～4 times.
Preferably, described organic solvent is one of ethyl acetate and n-butyl alcohol.
Preferably, described silica gel column chromatography is to carry out chromatographic isolation in 200～300 mesh silicagel columns, with petroleum ether-second
Acetoacetic ester mixed solvent is eluent gradient eluting, and wherein percentage by volume shared by ethyl acetate is stepped up 40% from 0；Institute
The Sephdex LH-20 gel filtration chromatography stated adopts mobile phase volume ratio for petroleum ether:Chloroform:Methanol=2:2:1；Described weight
Crystallization is to carry out in chloroform, acetone or ethyl acetate.
Application in preparation preventing and treating phytopathogen disinfectant use in agriculture for the described chloro different coumarin derivative.
Preferably, described phytopathogen is Glorosprium musarum Cookeet Mass (Colletotrichum musae) and rice banded sclerotial blight
Pathogenic bacteria (Rhizoctonia solani).
The present invention, with respect to prior art, has such advantages as and effect：
Chloro different coumarin derivative of the present invention has the work of very strong suppression Glorosprium musarum Cookeet Mass and Rhizoctonia solani Kuhn
With can be used as microorganism disinfectant use in agriculture, and raw material being had a extensive future with large-scale production.
Specific embodiment
With reference to embodiment, the present invention is described in further detail, but embodiments of the present invention not limited to this.
In embodiment, used Glorosprium musarum Cookeet Mass (Colletotrichum musae), Rhizoctonia solani Kuhn be (i.e.：Vertical
Withered silk kernel fungus) (Rhizoctonia solani) in patent " 201110423435.3, bacillus subtilises NB12 and its culture side
Disclosed in method and application ".
Trichoderma sp.09 document " Li Chunyuan, Gong Bing, Cox G.Daniel, Li Caili,
Wang Jinhua,Ding Wcijia.Dicltlorodiaportinol A,a new chlorine-containing
isocoumarin from an endophytic fungus Trichoderma sp.09 from Myoporum
bontioides A.Gray and its cytotoxic activity.Pltarmacognosy magazine,10(37):
S153-s158,2014. disclosed in ".
Embodiment 1
Prepare chloro different coumarin derivative by following steps：
(1) first in culture medium, spawn culture, culture used are carried out to Myoporum bontiodes endogenetic fungus Trichoderma sp.09
Base is containing glucose 1.0% (percetage by weight, similarly hereinafter), yeast extract 0.02%, peptone 0.1%, agar 1.0%, chlorination
Sodium 0.2%, remaining is water, is made into test tube slant, above-mentioned strain is cultivated 7 days at 28 DEG C during use；
(2) again fermentation culture is carried out to Trichoderma sp.09, used medium is containing rice 50.0%, chlorination
Calcium 1.5%, sodium chloride 1.0% and water surplus, quiescent culture 40 days at 25 DEG C of room temperature；
(3) the bacterial strain ethanol-water mixture (95 that step (2) is fermented:5) extract 3 times, after concentrating under reduced pressure, use second
Acetoacetic ester extraction is multiple (ethyl acetate can be replaced with n-butyl alcohol), and concentrated extract carries out color in 200～300 mesh silicagel columns
Spectrum separates, and with petroleum ether-ethyl acetate mixed solvent eluting, wherein percentage by volume shared by ethyl acetate is stepped up from 0
40%；The eluent merging 20%～30% petrol ether/ethyl acetate uses Sephdex LH-20 gel filtration chromatography again using flowing
Phase volume ratio is petroleum ether:Chloroform:Methanol=2:2:1 carries out separating, and gained solid uses chloroform (available acetone, ethyl acetate again
Replace) carry out recrystallization purifying repeatedly, obtain white, needle-shaped crystals, as described chloro different coumarin derivative.
Embodiment 2
Prepare chloro different coumarin derivative by following steps：
(1) first in culture medium, spawn culture, culture used are carried out to Myoporum bontiodes endogenetic fungus Trichoderma sp.09
Base is containing glucose 2.5% (percetage by weight, similarly hereinafter), yeast extract 0.2%, peptone 0.3%, agar 1.0%, sodium chloride
0.5%, remaining is water, is made into test tube slant, above-mentioned strain is cultivated 3 days at 28 DEG C during use；
(2) again fermentation culture is carried out to Trichoderma sp.09, used medium is containing rice 30.0%, chlorination
Calcium 1.5%, sodium chloride 2.0% and water surplus, quiescent culture 60 days at 30 DEG C；
(3) the bacterial strain methanol-water mixture (90 that step (2) is fermented:10) extract 2 times, after concentrating under reduced pressure, with just
Butanol, before immunoassay is multiple (n-butyl alcohol can be replaced with ethyl acetate), and concentrated extract carries out chromatograph in 200～300 mesh silicagel columns
Separate, with petroleum ether-ethyl acetate mixed solvent eluting, wherein percentage by volume shared by ethyl acetate is stepped up from 0
40%；The eluent merging 20%～30% petrol ether/ethyl acetate uses Sephdex LH-20 gel filtration chromatography again using flowing
Phase volume ratio is petroleum ether:Chloroform:Methanol=2:2:1 carries out separating, and gained solid uses acetone (available chloroform, ethyl acetate again
Replace) carry out recrystallization purifying repeatedly, obtain white, needle-shaped crystals, as described chloro different coumarin derivative.
Embodiment 3
Prepare chloro different coumarin derivative by following steps：
(1) first in culture medium, spawn culture, culture used are carried out to Myoporum bontiodes endogenetic fungus Trichoderma sp.09
Base is containing glucose 3.5% (percetage by weight, similarly hereinafter), yeast extract 0.5%, peptone 1.0%, agar 1.5%, sodium chloride
1.5%, remaining is water, is made into test tube slant, above-mentioned strain is cultivated 5 days at 28 DEG C during use；
(2) again fermentation culture is carried out to Trichoderma sp.09, used medium is containing rice 40.0%, chlorination
Calcium 0.5%, sodium chloride 2.5% and water surplus, quiescent culture 50 days at 30 DEG C；
(3) the bacterial strain ethanol-water mixture (80 that step (2) is fermented:20) extract 4 times, after concentrating under reduced pressure, with just
Butanol, before immunoassay is multiple (n-butyl alcohol can be replaced with ethyl acetate), and concentrated extract carries out chromatograph in 200～300 mesh silicagel columns
Separate, with petroleum ether-ethyl acetate mixed solvent eluting, wherein percentage by volume shared by ethyl acetate is stepped up from 0
40%；The eluent merging 20%～30% petrol ether/ethyl acetate uses Sephdex LH-20 gel filtration chromatography again using flowing
Phase volume ratio is petroleum ether:Chloroform:Methanol=2:2:1 carries out separating, and gained solid uses acetone (available chloroform, ethyl acetate again
Replace) carry out recrystallization purifying repeatedly, obtain white, needle-shaped crystals, as described chloro different coumarin derivative.
After testing, embodiment 1,2 and 3 gained compound chloro different coumarin derivative Dichlorodiaportinolide
Spectral data as follows：mp 185-187℃；[α]D 25+ 17 ° (c 0.04, acetone)；IR(KBr)cm-13382,2810,1760,
1681,1625,1511,1302.UVλmax(CH3OH)nm 330,274,245.HR-ESI-MS m/z:389.0184([M+H]+,
C16H15Cl2O7,calcd.389.0188).1H-NMR(600MHz,CD3COCD3):11.02(1H,s,8-OH),6.70(1H,s,
H-4),6.63(1H,d,2.4,H-5),6.52(1H,s,H-14),6.51(1H,d,2.4,H-7),5.55(1H,d,6.0,12-
OH),4.74(1H,m,H-12),3.92(3H,s,6-OCH3),3.32(2H,dd,15.0Hz,8.4Hz,H-9),3.03(1H,
dd,7.2Hz,15.0Hz,H-10b),2.42(1H,dd,7.2Hz,15.0Hz,H-10a).13C-NMR(150MHz,
CD3COCD3):174.7(C-13),167.0(C-1),165.6(C-6),165.3(C-8),150.9(C-3),139.1(C-4a),
109.0(C-4),101.7(C-5),100.8(C-7),100.1(C-8a),85.2(C-10),76.3(C-14),67.5(C-
12),55.5(C-6-OCH3),40.3(C-9),36.6(C-11).
The structural formula of embodiment 1,2 and 3 gained compound is as follows：
Embodiment 4
The compounds of this invention is tested to Glorosprium musarum Cookeet Mass and Rhizoctonia solani Kuhn bacteriostatic activity：
Gained compound is measured using doubling dilution antibacterial dense to the minimum of Glorosprium musarum Cookeet Mass and Rhizoctonia solani Kuhn
Degree (MIC).Test strains cultivate 24h in 28 DEG C of constant incubators, observe the growing state of bacterium in test tube, do not have bacteria growing
Concentration corresponding to test tube is its minimal inhibitory concentration.Positive control made by carbendazim.Result display the compounds of this invention is to perfume (or spice)
The minimal inhibitory concentration of any of several broadleaf plants anthrax bacteria and Rhizoctonia solani Kuhn is respectively 25 μ g/mL and 6.25 μ g/mL, the activity of latter of which
Consistent with carbendazim (to two bacterium MIC=6.25 μ g/mL).
Embodiment 5
The compounds of this invention is tested to Rhizoctonia solani Kuhn greenhouse field bactericidal activity：
The compounds of this invention according to《Pesticide field efficacy medicine test criterion》, booth is tested it to Rhizoctonia solani Kuhn sense
The prevention effect of dye Oryza sativa L..Result shows that the compounds of this invention has significant bactericidal activity to Rhizoctonia solani Kuhn.To sense
The Oryza sativa L. of dye Rhizoctonia solani Kuhn is carried out in preventative leaf surface spraying test, of the present inventionization when concentration is 400,200,100ppm
Compound is respectively 98%, 96%, 92% to the bacteriostasis rate of rice banded sclerotial blight, suitable with carbendazim activity or close to (98%, 98%,
98%)；To infection Rhizoctonia solani Kuhn Oryza sativa L. carry out in therapeutic leaf surface spraying test, when concentration is for 400ppm this
Bright compound is 90% to the bacteriostasis rate of rice banded sclerotial blight, with carbendazim activity close to (95%).
Embodiment 6
The compounds of this invention is tested to the bactericidal activity of Glorosprium musarum Cookeet Mass preservation after Banana：
Carry out preventative any of several broadleaf plants body to the Fructus Musae of infection Glorosprium musarum Cookeet Mass to spray, after natural air drying, put into indoor 18 DEG C～
20 DEG C preserve 14 days, the healthy fruit when concentration is for 400ppm, after spraying through the compounds of this invention preparation>80%, do not spray this
The blank healthy fruit of invention compound formulation is 10%.
Effect example 4,5,6 test result indicate that the compounds of this invention is to Glorosprium musarum Cookeet Mass and Rhizoctonia solani Kuhn
There is very strong Developing restraint effect, all kinds of solvents, auxiliary agent can be added, make spray or powder is used as disinfectant use in agriculture.
Above-described embodiment is the present invention preferably embodiment, but embodiments of the present invention are not subject to above-described embodiment
Limit, other any spirit without departing from the present invention and the change made under principle, modification, replacement, combine, simplify,
All should be equivalent substitute mode, be included within protection scope of the present invention.
Claims (10)
1. a kind of chloro different coumarin derivative it is characterised in that：Its molecular formula is C16H14Cl2O7, structural formula is：
2. the preparation method of the chloro different coumarin derivative described in claim 1 is it is characterised in that comprise the following steps：First exist
In bacterium culture medium, spawn culture is carried out to Myoporum bontiodes endogenetic fungus Trichoderma sp.09, then by strain in fermentation culture
Base carries out fermentation culture, after gained mycelia alcohol-water or methanol-water mixture extraction concentrating under reduced pressure, is extracted with organic solvent
Take；Extract carries out silica gel column chromatography, Sephdex LH-20 gel filtration chromatography after concentrating, and ties after gained eluent is concentrated again
Crystalline substance obtains white crystal, as described chloro different coumarin derivative.
3. chloro different coumarin derivative according to claim 2 preparation method it is characterised in that：
Described bacterium culture medium contains the component of following percetage by weight：Glucose 1.0～3.5%, yeast extract 0.02～
1.5%, peptone 0.01～1.5%, agar 1.0～2.5%, sodium chloride 0.2～2.0% and water surplus.
4. chloro different coumarin derivative according to claim 2 preparation method it is characterised in that：
The condition of described spawn culture is：Cultivate 3～10 days at 20～35 DEG C.
5. chloro different coumarin derivative according to claim 2 preparation method it is characterised in that：
Described fermentation medium contains the component of following percetage by weight：Rice 10.0～70.0%, calcium chloride 0.3～
2.5%, sodium chloride 1.0～5.5% and water surplus.
6. chloro different coumarin derivative according to claim 2 preparation method it is characterised in that：
The condition of described fermentation culture is：Cultivate 30～80 days at 25～30 DEG C.
7. chloro different coumarin derivative according to claim 2 preparation method it is characterised in that：
The volume ratio of described alcohol-water or methanol-water mixture is 100：0～80：20；
The number of times of described extraction is 2～4 times；
Described organic solvent is one of ethyl acetate and n-butyl alcohol.
8. chloro different coumarin derivative according to claim 2 preparation method it is characterised in that：
Described silica gel column chromatography is to carry out chromatographic isolation in 200～300 mesh silicagel columns, with petroleum ether-ethyl acetate mixing
Solvent is eluent gradient eluting, and wherein percentage by volume shared by ethyl acetate is stepped up 40% from 0；Described
Sephdex LH-20 gel filtration chromatography adopts mobile phase volume ratio for petroleum ether:Chloroform:Methanol=2:2:1；Described recrystallization
It is to carry out in chloroform, acetone or ethyl acetate.
9. the answering in preparation preventing and treating phytopathogen disinfectant use in agriculture of the chloro different coumarin derivative described in claim 1
With.
10. according to claim 9 application it is characterised in that：Described phytopathogen is Glorosprium musarum Cookeet Mass
(Colletotrichum musae) and Rhizoctonia solani Kuhn (Rhizoctonia solani).
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