CN110003152A - 2 (5H)-furanone based derivatives of one kind and its preparation method and application - Google Patents
2 (5H)-furanone based derivatives of one kind and its preparation method and application Download PDFInfo
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- CN110003152A CN110003152A CN201910170564.2A CN201910170564A CN110003152A CN 110003152 A CN110003152 A CN 110003152A CN 201910170564 A CN201910170564 A CN 201910170564A CN 110003152 A CN110003152 A CN 110003152A
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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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/58—One oxygen atom, e.g. butenolide
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- C—CHEMISTRY; METALLURGY
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
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Abstract
The invention discloses a kind of 2 (5H)-furanone based derivatives and its preparation method and application, feature is the structural formula of 2 (the 5H)-furanone based derivative as shown in I, preparation methods steps include obtaining the fermentation material for containing 2 (5H)-furanone based derivatives by the marine fungi fermented and cultured that deposit number is CCTCC No:M2014086, then methanol is added and impregnates ultrasound filtration, it is evaporated, it is evaporated after being extracted with ethyl acetate again, obtain coarse extract, by the extract through depressurizing silica gel column chromatography, gel filtration chromatography, reverse phase medium pressure column chromatography, last half preparative high-performance liquid chromatographic of reverse phase isolates and purifies to obtain, 2 (the 5H)-furanone based derivative has plant growth inhibiting effect, advantage is that chemical compounds I has the ability for inhibiting plant lateral roots growth, potentially contribute to control farming Object excessive growth and help to increase its yield.
Description
Technical field
The present invention relates to a kind of 2 (5H)-furanone based derivatives, more particularly, to a kind of 2 (5H)-furanone based derivatives
And its preparation method and application.
Background technique
2 (5H)-furanones are five-membered heterocycles also known as γ-hydroxyl butenolide, and 3,4,5 can deposit
In substituent group, and condensed ring can also be formed, especially [3,4] position be easy to same phenyl ring it is thick and.Change containing 2 (5H)-furanone structures
Object is closed to be widely present in natural products, research find such compound with extensive bioactivity, as antibacterial, it is antimycotic,
Anti-inflammatory, antiviral and anticancer isoreactivity.The present inventor's research learns that sponge is total to epiphytic fungiAspergillus ustus(preservation
In China typical culture collection center, deposit number are as follows: CCTCC No:M2014086) ethyl acetate of solid fermentation extracts
Object is inhibited to the lateral root growth of arabidopsis Columbia-0.Then its active constituent is studied, it is isolated
A kind of 2 new (5H)-furanone based derivatives.The chemical structure and its plant growth for having not yet to see the compound inhibit to live
The report of property, therefore in the market also there is not yet plant growth inhibitor related to this.
Summary of the invention
Technical problem to be solved by the invention is to provide a kind of 2 (5H)-furanones with plant lateral roots inhibitory activity
Analog derivative and its preparation method and application.
The technical scheme of the invention to solve the technical problem is: a kind of 2 (5H)-furanone based derivatives, this 2
The structural formula of (5H)-furanone based derivative is as shown in I:
(I).
The preparation method of above-mentioned 2 (5H)-furanone based derivative, specifically comprises the following steps:
(1) fermenting and producing: by deposit number be CCTCC No:M2014086 aspergillus ustus (Aspergillus ustus) scribing line
It brings back to life, then chooses a single colonie and be inoculated into PDB fluid nutrient medium, under the conditions of 27-29 DEG C, 140-160rpm, cultivate 5 days
It is used as seed liquor afterwards；Seed liquor is inoculated into the conical flask equipped with rice medium again, in 27-29 DEG C, is left to ferment 28-32
It；
(2) acquisition of coarse extract: being added methanol into the conical flask after fermentation, 12-18 minutes ultrasonic by solid immersion, stands
After overnight, methanol extract liquid filtered through gauze is removed into solid residue；It, will after solid residue methanol is repeated extraction 3-5 times
Methanol extract liquid is evaporated after merging；Then it is dissolved with water, adds and repeat extraction 4-6 times with the isometric ethyl acetate of water, close
And be concentrated under reduced pressure after extract liquor and remove ethyl acetate, obtain coarse extract；
(3) compound isolates and purifies: after coarse extract methylene chloride and methanol mixed solvent dissolution, adding 200-300 mesh silicon
Glue mixes sample, and the petrol ether/ethyl acetate with volume ratio 1:1 is eluant, eluent, carries out decompression silica gel column chromatography to coarse extract, collection is washed
De- component；By the elution fraction by gel filtration chromatography (LH-20), after methylene chloride and methanol mixed solvent elution, then pass through
Compression leg chromatographic isolation in reverse phase is crossed, uses elution ratio for 15-100% methanol/water gradient elution 140 minutes, flow velocity 20ml/
Min collects the flow point that appearance time is 52 minutes, and finally the flow point isolates and purifies to obtain through half preparation reversed-phase high performance liquid chromatography
2 (5H)-furanone based derivatives, structure are shown in formula I:
(I).
The formula of the PDB fluid nutrient medium is as follows: potato 200g, glucose 20g, sea crystal 35g and distillation
Water 1L；The formula of the rice medium is as follows: rice 100g, sea crystal 3.5g and distilled water 100ml.
The volume ratio of methylene chloride and methanol is 1:1 in the methylene chloride and methanol mixed solvent.
The eluent of half preparation reversed-phase high performance liquid chromatography is that 18:82 is mixed acetonitrile by volume with water.
The purposes of above-mentioned 2 (5H)-furanone based derivative, described 2 (5H)-furanone based derivatives are raw in preparation plant
Purposes in terms of long inhibitor.
Compared with the prior art, the advantages of the present invention are as follows: the present invention 2 (5H)-furanone based derivatives of one kind and its system
Preparation Method and purposes obtain the fermentation material containing 2 (5H)-furanone based derivatives by microbial fermentation culture, then will hair
Ferment object with methanol impregnate, ethyl acetate extract, obtain coarse extract, by the coarse extract through depressurize silica gel column chromatography, gel filtration chromatography, in
Pressure column chromatography and half preparative high-performance liquid chromatographic of reverse phase isolate and purify to obtain, which can be used as tool
There are the new plant growth inhibitor ingredient or lead compound of plant growth inhibiting effect；The present invention is obtained by microbial fermentation
2 (5H)-furanone based derivatives, operating procedure is simple, feature with short production cycle, product cost is low and no pollution to the environment.
Above-mentioned aspergillus ustus (Aspergillus ustus), which is DJ003 bacterial strain, and deposit number is CCTCC No.
M2014086, China typical culture collection center was preserved on 03 14th, 2014, and preservation address is the China Wuhan military
Chinese university.
Detailed description of the invention
Fig. 1 is chemical compounds I to arabidopsis Columbia-0(Col-0) lateral root growth inhibitory activity.100 μM of chemical compounds I
It is added to Murashige and Skoog(MS) in culture medium, then the Col-0 seed handled well is inoculated on MS culture medium, with
After be placed on 16 hours illumination/8 hour dark photoperiod (120 μM of photon m of luminous intensity-2s-1) growth room in incubate, ten
After it, the quantity of lateral root is observed under the microscope.Use the DMSO of 2%(v/v) as negative control.
Specific embodiment
The present invention will be described in further detail below with reference to the embodiments of the drawings.
Embodiment 1
2 (5H)-furanone based derivative structural formulas of one kind are as shown in I:
(I).
Embodiment 2
The preparation method of (5H)-furanone based derivative 2 as shown in I formula, steps are as follows:
(1) fermenting and producing: by deposit number be CCTCC No:M2014086 aspergillus ustus (Aspergillus ustus) scribing line is again
It is living, it then chooses a single colonie and is inoculated into PDB fluid nutrient medium (potato 200g, glucose 20g, sea crystal 35g and distillation
Water 1L) in, under the conditions of 27-29 DEG C, 140-160rpm, seed liquor is used as after culture 5 days；Seed liquor (20ml/ bottles) is connect again
Kind is into the 100 bottled 1L conical flasks for having rice medium (rice 100g, sea crystal 3.5g and distilled water 100ml), in 27-
It 29 DEG C, is left to ferment 28-32 days；
(2) acquisition of coarse extract: being added methanol into the conical flask after fermentation, 12-18 minutes ultrasonic by solid immersion, stands
After overnight, methanol extract liquid filtered through gauze is removed into solid residue；After solid residue is repeated extraction 3-5 times, methanol is mentioned
It is evaporated after taking liquid to merge；Then it is dissolved with the water of 1L, adds isometric ethyl acetate and repeat extraction 4-6 times, merge extraction
It is concentrated under reduced pressure after liquid and removes ethyl acetate, obtain coarse extract；
(3) compound isolates and purifies:
After coarse extract methylene chloride and methanol (volume ratio of methylene chloride and methanol is 1:1) mixed solvent dissolution, add
200-300 mesh silica gel mixed sample, is eluant, eluent with the petrol ether/ethyl acetate that volume ratio is 1:1, carries out decompression silica gel to coarse extract
Column chromatography, collects elution fraction；By the elution fraction by gel filtration chromatography (LH-20), with methylene chloride and methanol (dichloromethane
The volume ratio of alkane and methanol is 1:1) after mixed solvent elution, using compression leg chromatographic isolation in reverse phase, use elution ratio for
15-100% methanol/water gradient elution 140 minutes, flow velocity 20ml/min, the flow point that appearance time is 52 minutes is collected, finally
The flow point isolates and purifies to obtain 2 (5H)-furanone based derivatives, structure such as Formulas I institute through half preparation reversed-phase high performance liquid chromatography
Show:
(I),
Wherein the eluent of half preparation reversed-phase high performance liquid chromatography is that 18:82 is mixed acetonitrile by volume with water.
The faint yellow oily of compound 1, molecular formula C11H16O4, [α] 24 D=+ 20.67 (c0.6, MeOH), sun from
Sub- HRESIMSm/z: 235.0940 [M+Na]+,1H and13C-NMR data are shown in Table 1.
1 chemical compounds I of table1H and13C NMR data (600 and 140-160MHz, in DMSO-d 6)
Note: this table signals assignment be based on DEPT,1H-1H COSY, HSQC and HMBC spectrum analysis result.Hydrogen signal multiplicity point
Yong s(singlet), d(doublet), t(triplet) and m(multiplet) table.
Embodiment 3
Arabidopsis Columbia-0(Col-0) lateral root growth reaction test
(1) laboratory sample
The preparation of sample solution: test sample is the chemical compounds I sterling isolated and purified in above-described embodiment 2, and precision weighs
Appropriate amount of sample, for surveying activity.
(2) experimental method
The lateral root growth inhibition activity for determining chemical compounds I is reacted by Col-0 lateral root growth.100 μM of drugs are added to
Murashige and Skoog(MS) in culture medium, then the Col-0 seed handled well is inoculated on MS culture medium, is subsequently put on
With 16 hours illumination/8 hour dark photoperiod (120 μM of photon m of luminous intensity-2s-1) growth room in incubate, after ten days,
The quantity of microscopically observation lateral root.Use the DMSO of 2%(v/v) as negative control.
(3) experimental result
In the test of Col-0 lateral root growth reaction.100 μM of chemical compounds I is added to Murashige and Skoog(MS) culture
In base, then the Col-0 seed handled well is inoculated on MS culture medium, is subsequently put on black with 16 hours illumination/8 hour
Dark photoperiod (120 μM of photon m of luminous intensity-2s-1) growth room in incubate ten days, by the number for observing lateral root under the microscope
Amount.As shown in Figure 1, chemical compounds I, under 100 μM of concentration, Col-0 lateral root is not grown substantially, show that compound 1 may be as effective
Plant growth inhibitor.Many plant growth inhibitors potentially contribute to control crops excessive growth and have such as B9 and Pix
Help increase its yield.Therefore, chemical compounds I is derivative as 2 (5H)-Furanones with strong plant lateral roots growth inhibition performance
Object, it can also be used to which increasing crop yield increases income.
Above description is not limitation of the present invention, and the present invention is also not limited to the example above.The art it is common
Within the essential scope of the present invention, the variations, modifications, additions or substitutions made also should belong to protection of the invention to technical staff
Range.
Claims (6)
1. one kind 2 (5H)-furanone based derivative, it is characterised in that such as I institute of structural formula of 2 (the 5H)-furanone based derivative
Show:
(I).
2. a kind of preparation method of 2 (5H)-furanone based derivative according to claim 1, it is characterised in that specific packet
Include following steps:
(1) fermenting and producing: by deposit number be CCTCC No:M2014086 aspergillus ustus (Aspergillus ustus) scribing line
It brings back to life, then chooses a single colonie and be inoculated into PDB fluid nutrient medium, under the conditions of 27-29 DEG C, 140-160rpm, cultivate 5 days
It is used as seed liquor afterwards；Seed liquor is inoculated into the conical flask equipped with rice medium again, in 27-29 DEG C, is left to ferment 28-32
It；
(2) acquisition of coarse extract: being added methanol into the conical flask after fermentation, 12-18 minutes ultrasonic by solid immersion, stands
After overnight, methanol extract liquid filtered through gauze is removed into solid residue；It, will after solid residue methanol is repeated extraction 3-5 times
Methanol extract liquid is evaporated after merging；Then it is dissolved with water, adds and repeat extraction 4-6 times with the isometric ethyl acetate of water, close
And be concentrated under reduced pressure after extract liquor and remove ethyl acetate, obtain coarse extract；
(3) compound isolates and purifies: after coarse extract methylene chloride and methanol mixed solvent dissolution, adding 200-300 mesh silicon
Glue mixes sample, and the petrol ether/ethyl acetate with volume ratio 1:1 is eluant, eluent, carries out decompression silica gel column chromatography to coarse extract, collection is washed
De- component；By the elution fraction by gel filtration chromatography, after methylene chloride and methanol mixed solvent elution, using in reverse phase
Compression leg chromatographic isolation uses elution ratio for 15-100% methanol/water gradient elution 140 minutes, flow velocity 20ml/min, collects
The flow point that appearance time is 52 minutes, finally the flow point isolates and purifies to obtain 2 (5H)-furans through half preparation reversed-phase high performance liquid chromatography
It mutters ketones derivant, structure is shown in formula I:
(I).
3. a kind of preparation method of 2 (5H)-furanone based derivative according to claim 2, it is characterised in that described
The formula of PDB fluid nutrient medium is as follows: potato 200g, glucose 20g, sea crystal 35g and distilled water 1L；The rice
The formula of culture medium is as follows: rice 100g, sea crystal 3.5g and distilled water 100ml.
4. a kind of preparation method of 2 (5H)-furanone based derivative according to claim 2, it is characterised in that described
The volume ratio of methylene chloride and methanol is 1:1 in methylene chloride and methanol mixed solvent.
5. a kind of preparation method of 2 (5H)-furanone based derivative according to claim 2, it is characterised in that: described
The eluent of half preparation reversed-phase high performance liquid chromatography is that 18:82 is mixed acetonitrile by volume with water.
6. a kind of purposes of 2 (5H)-furanone based derivative according to any one of claims 1-5, it is characterised in that:
Purposes of 2 (the 5H)-furanone based derivatives in terms of preparing plant growth inhibitor.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110229127A (en) * | 2019-07-22 | 2019-09-13 | 海南师范大学 | A kind of butyrolactone compound and the preparation method and application thereof in mangrove endogenetic fungus source |
| CN111533715A (en) * | 2020-04-22 | 2020-08-14 | 南京农业大学 | 2(5H) -furan-2-one derivative, preparation method thereof and application thereof in inhibiting rice tillering |
| CN113264913A (en) * | 2021-04-14 | 2021-08-17 | 宁波大学 | Benzopyrone compound and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106565639A (en) * | 2016-10-14 | 2017-04-19 | 宁波大学 | Tetrahydrofuran compound and preparation method and application thereof |
| CN110229127A (en) * | 2019-07-22 | 2019-09-13 | 海南师范大学 | A kind of butyrolactone compound and the preparation method and application thereof in mangrove endogenetic fungus source |
-
2019
- 2019-03-07 CN CN201910170564.2A patent/CN110003152B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106565639A (en) * | 2016-10-14 | 2017-04-19 | 宁波大学 | Tetrahydrofuran compound and preparation method and application thereof |
| CN110229127A (en) * | 2019-07-22 | 2019-09-13 | 海南师范大学 | A kind of butyrolactone compound and the preparation method and application thereof in mangrove endogenetic fungus source |
Non-Patent Citations (1)
| Title |
|---|
| LIMING HUANG ET AL.: ""A new lateral root growth inhibitor from the sponge-derived fungus Aspergillus sp. LS45"", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110229127A (en) * | 2019-07-22 | 2019-09-13 | 海南师范大学 | A kind of butyrolactone compound and the preparation method and application thereof in mangrove endogenetic fungus source |
| CN111533715A (en) * | 2020-04-22 | 2020-08-14 | 南京农业大学 | 2(5H) -furan-2-one derivative, preparation method thereof and application thereof in inhibiting rice tillering |
| CN113264913A (en) * | 2021-04-14 | 2021-08-17 | 宁波大学 | Benzopyrone compound and preparation method and application thereof |
| CN113264913B (en) * | 2021-04-14 | 2022-06-21 | 宁波大学 | Benzopyrone compound and preparation method and application thereof |
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| CN110003152B (en) | 2022-12-13 |
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