CN108383811A - A kind of furanone derivatives and its extracting method and application - Google Patents
A kind of furanone derivatives and its extracting method and application Download PDFInfo
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Abstract
The invention discloses a kind of furanone derivatives and its extracting method and applications, and Decaisnea fargesii endogenetic fungus DS37 secondary metabolites petrol ether/ethyl acetate/methanol is extracted, and merge extracting solution and filter, recycle mixed solvent, are concentrated under reduced pressure, obtain crude product medicinal extract；Obtained crude product medicinal extract is eluted with the petrol ether/ethyl acetate of different volumes gradient/methanol eluant, eluent respectively on silica gel chromatographic column, obtains tetra- components of A D；By B component medicinal extract on silica gel chromatographic column, it is eluted respectively with the petrol ether/ethyl acetate eluant, eluent of different volumes gradient, obtain six components of B1 B6, B6 components continue on silica gel chromatographic column, it is eluted respectively with the petrol ether/ethyl acetate eluant, eluent of different volumes gradient, nine components of B6.1 B6.9 are obtained, B6.9 components are recrystallized with methanol, obtain furanone derivatives.The present invention isolated furanone derivatives from Decaisnea fargesii endogenetic fungus DS37 secondary metabolites, and the compound has preferable bacteriostatic activity.
Description
Technical field
The present invention relates to furanone derivatives preparation fields, and in particular to a kind of furanone derivatives and its extracting method and
Using.
Background technology
Decaisnea fargesii (Decaisnea insignis (Griff.) Hook.f.＆Thomson) is called cat melon (Qinling Mountains), short
Qi Shu etc. is Lardizabalaceae (Lardiya balaeeae) Decaisnea fargesii platymiscium.Grow thickly the upright shrub of fallen leaves, is distributed widely in China
The west and south and middle part.Plants of Lardizabalaceae Decaisnea fargesii is the traditional civil Chinese herbal medicine in China, acrid flavour, sweet, mild-natured, root and fruit
It is sweet, cool that there is removing heat from the lung to relieve cough, dispelling wind and eliminating dampness, treatment rheumatic arthritis and other effects.So far, the research of Decaisnea fargesii is mainly collected
In in its plant chemical ingredient, and it is relatively fewer to the research of its endogenetic fungus.Endogenetic fungus refers to during growth extremely
It is few to be lived in plant there are one the stage, but cause notable dysgenic fungi without to plant tissue.It is reported that interior
Raw secondary fungus metabolite type mainly has：The compounds such as alkaloid, terpene, steroidal, organic acid all have certain life
Object activity.However have no the report in relation to furanone derivatives in Decaisnea fargesii endogenetic fungus.
Invention content
The purpose of the present invention is to provide a kind of furanone derivatives and its extracting method and applications, above-mentioned existing to overcome
Defect existing for technology, the chemical combination of the present invention isolated structure novel from Decaisnea fargesii endogenetic fungus DS37 secondary metabolites
Object furanone derivatives, and the furanone derivatives have preferable bacteriostatic activity.
In order to achieve the above objectives, the present invention adopts the following technical scheme that：
The chemical structural formula of a kind of furanone derivatives, the furanone derivatives is：
A kind of extracting method of furanone derivatives, includes the following steps：
(1) to be extracted from Decaisnea fargesii endogenetic fungus DS37 solid fermentations object as raw material petroleum ether, ethyl acetate and methanol
Several times, merge extracting solution and filter, recycle mixed solvent, filtrate decompression concentration obtains crude product medicinal extract；
(2) for the crude product medicinal extract for obtaining step (1) on silica gel chromatographic column, it is 1 to use volume gradient respectively:0:0,0:1:0,
0:1:1,0:0:1 petrol ether/ethyl acetate/methanol eluant, eluent is eluted, and tetra- components of A-D are obtained；
(3) for the B component for obtaining step (2) on silica gel chromatographic column, it is 1 to use volume gradient respectively:0,5:1,2:1,1:
1,1:2,0:1 petrol ether/ethyl acetate eluant, eluent is eluted, and six components of B1-B6 are obtained, and B6 components continue in silica gel color
It composes on column, is 1 with volume gradient:0,10:1,5:1,4:1,3:1,2:1,1:1,1:2,0:1 petrol ether/ethyl acetate elution
Agent is eluted, and nine components of B6.1-B6.9 are obtained, and B6.9 components are recrystallized with methanol, obtain furanone derivatives.
Further, further include step (4)：The furanone derivatives that step (3) obtains are taken to be packed into container A after being dissolved in DMSO
In, container A is placed in the container B for filling ether solvent, is then sealed the mouth of container B, standing waits for that crystal is precipitated, and is somebody's turn to do
The monocrystalline of furanone derivatives.
Further, 5mg furanone derivatives are dissolved in the DMSO in step (4) per 20mL.
Further, the petroleum ether, ethyl acetate and methanol are industry standard.
Further, by product petroleum ether/second of drying in the shade after Decaisnea fargesii endogenetic fungus DS37 solid fermentations in step (1)
Acetoacetic ester/methanol extracts 8 times.
A kind of application of furanone derivatives on antibacterial.
Further, the antibacterial inhibiting effect referred to bacterium or fungi.
Further, the antibacterial inhibiting effect referred to streptococcus lactis and Alternaria brassicae.
Compared with prior art, the present invention has technique effect beneficial below：
Decaisnea fargesii endogenetic fungus DS37 secondary metabolites-furanone derivatives of the present invention are a kind of structure novels
Furanones compound, molecular formula C7H8O4, in addition the present invention is by after to Decaisnea fargesii endogenetic fungus DS37 solid fermentations
The secondary metabolite that dries in the shade extracts, and obtains this furanone derivatives, passes through the antibacterial work to furanone derivatives of the present invention
Property test, it is found that the compound has preferable antibacterium and fungi activity, especially to streptococcus lactis (bacterium) and Cabbage Leaf Spot
Bacterium (fungi) has good bacteriostatic activity, is the bacteriostatic active ingredients of Decaisnea fargesii endogenetic fungus DS37 secondary metabolites, therefore,
It can be used for cultural control and Efficacy of Pesticide.
Description of the drawings
Fig. 1 is furanone derivatives of the present invention1H-NMR is composed；
Fig. 2 is furanone derivatives of the present invention13C-NMR is composed；
Fig. 3 is (135 °) spectrums of DEPT of furanone derivatives of the present invention；
Fig. 4 is the spectrum COSY of furanone derivatives of the present invention；
Fig. 5 is the NOESY of furanone derivatives of the present invention；
Fig. 6 is the spectrum HSQC of furanone derivatives of the present invention；
Fig. 7 is the HMBC of furanone derivatives of the present invention；
Fig. 8 is that the HR-ESI-M of furanone derivatives of the present invention is composed；
Fig. 9 is the x-ray crystal structure figure of furanone derivatives of the present invention；
Figure 10 is the structure fragment of furanone derivatives of the present invention, wherein (a) is furanone segment；(b) it is propionic acid segment；
Figure 11 is the structure chart of furanone derivatives of the present invention.
Preservation explanation
The present invention is following to having been carried out from Decaisnea fargesii plant stem portion from one plant of obtained endogenetic fungus Tabin aspergillus DS37
Preservation：
The preservation time：On March 22nd, 2018, preservation place：China, Wuhan.China typical culture collection center
(CCTCC)；Preserving number is CCTCC M 2018147, and Classification And Nomenclature is Tabin aspergillus (Aspergillus tubingensis).
Specific implementation mode
Embodiments of the present invention are described in further detail below：
A kind of Furanones compound, the chemical structural formula of the compound：
The extracting method of the compound is as follows：
(1) with Decaisnea fargesii endogenetic fungus DS37 secondary metabolites (9.2kg) for raw material petrol ether/ethyl acetate/first
Alcohol extracts 8 times, merges extracting solution and filters, recycle mixed solvent, is concentrated under reduced pressure, obtains crude product medicinal extract 1500g；
(2) for the crude product medicinal extract for obtaining step (1) on silica gel chromatographic column, it is 1 to use volume gradient respectively:0:0,0:1:0,
0:1:1,0:0:1 petrol ether/ethyl acetate/methanol eluant, eluent is eluted, and A (110g), B (420g), C (700g), D are obtained
(100g) four components；
(3) it to the B component medicinal extract of step (2), on silica gel chromatographic column, is washed with the petrol ether/ethyl acetate of different gradients
De- agent (1:0,5:1,2:1,1:1,1:2,0:1, v/v) it is eluted, obtains six components of B1-B6, B6 components continue in silica gel
In chromatographic column, with the petrol ether/ethyl acetate (1 of different gradients:0,10:1,5:1,4:1,3:1,2:1,1:1,1:2,0:1,v/
V) eluant, eluent is eluted, and obtains nine components of B6.1-B6.9, and B6.9 components are recrystallized with methanol, are obtained pure
Furanone derivatives 18.2mg.
(4) the furanone derivatives 5mg for taking step (3) to obtain, the DMSO for being dissolved in 20mL are fitted into bottle, bottle are put
In the big bottle for filling ether solvent, then the mouth of big bottle is sealed, standing waits for that crystal is slowly precipitated, and 3 groups of parallel laboratory test obtains
The monocrystalline of the compound.
Decaisnea fargesii endogenetic fungus DS37 secondary metabolites-furanone derivatives prepared by the present invention are that a kind of structure is new
The Furanones compound of grain husk, yet there are no the report for being separated to such compound from the endogenetic fungus of Decaisnea fargesii plant at present,
Also it has no isolated this compound report from other plant and endogenetic fungus, more there are no the side of this artificial synthesized compound
Method.The method that the present invention uses silica gel column chromatography and recrystallization to the product that dries in the shade after Decaisnea fargesii endogenetic fungus DS37 solid fermentations
Separation identifies the Furanones compound of a structure novel, which is to report for the first time.
Novel compound of present invention Decaisnea fargesii endogenetic fungus DS37 secondary metabolites-furanone derivatives are no color chips
Shape crystal, HR-ESI-MS are provided [M-H] at m/z 155.0352-Peak calculates that its molecular formula is C7H8O4,1H and13C nuclear-magnetisms are total
Data of shaking are as shown in table 1, and the crystallographic data of furanone derivatives is as shown in table 2.
1 furanone derivatives A's of table1H and13C nuclear magnetic datas
The crystallographic data of 2 furanone derivatives A of table
By the bacteriostatic activity test to the compounds of this invention, it is found that the compound has preferable antibacterium and fungi to live
Property, especially there is good bacteriostatic activity to streptococcus lactis (bacterium) and Alternaria brassicae (fungi), is Decaisnea fargesii endogenetic fungus
Therefore the bacteriostatic active ingredients of DS37 secondary metabolites can be used for cultural control and Efficacy of Pesticide.
As shown in figures 1-8, by furanone derivatives of the present invention1H-NMR、13C-NMR、DEPT、2D NMR(COSY、
NOESY, HSQC, HMBC) spectrum and HR-ESI-M spectrum learn the compound structure.Specifically：
1H-NMR(400HZ,DMSO-d6) in spectrum, δH12.33 (1H, s), there are an active hydrogens in prompting structure；δH
5.93 (1H, s), there are an olefinic protons in prompting structure；δH4.84 (2H, s), in prompting structure there are one with inhale electricity
The connected methylene of subbase group；δH2.58-2.61 (2H, t, J=8.2Hz) and 2.54-2.57 (2H, t, J=4.6Hz) is prompted
There are two methylene segments in structure.
13C-NMR (100HZ, DMSO-d6) in spectrum, provide 7 carbon signals, wherein δC173.82 being carbonyl carbon with 173.45
Signal；(135 °) of DEPT is composed, and there is also a methine carbon, δ in prompting structureC114.08；Three mesomethylene carbons, δC
73.11,30.99 and 23.45.
Hsqc spectrum provides the information that all hydrogen carbon are connected directly in structure, as shown in table 1.δH2.58-2.61 with δC 23.45
And δH2.54-2.57 with δCThere may be-CH in 30.99 related prompting structures2-CH2Segment.
δ in HMBC spectrumsH4.84 with δC173.82,171.55 is related to 114.08, and there are structure fragments for prompt --- furans
Ketone segment (in such as Figure 10 shown in (a))；δH2.58-2.61 with δC30.99 is related, there is-CH in prompting structure2-CH2Piece
Section；And δH2.54-2.57 with δC173.45 is related, prompts that there are structure fragments --- propionic acid segment (in Figure 10 (b) institute
Show).
In NOESY spectrums, δH5.93 is related to 2.58-2.61, δH4.84 is related to 2.58-2.61, illustrates furanone segment
It is connected with propionic acid segment, the structure of compound A is finally determined.The compound is to have no the new furanone derivatives of document report
Class compound, related NMR data ownership are as shown in table 1.
X-ray crystal structure figure finally determines the stereochemical structure of the compound.
With reference to embodiment, the present invention will be further described：
Decaisnea fargesii endogenetic fungus DS37 secondary metabolite 9.2kg are extracted 8 times with petrol ether/ethyl acetate/methanol, are closed
And extracting solution and filter, mixed solvent is recycled, is concentrated under reduced pressure, obtains crude product medicinal extract 1500g；Obtained crude product medicinal extract is in silica gel color
It composes on column, it is 1 to use volume gradient respectively:0:0,0:1:0,0:1:1,0:0:1 petrol ether/ethyl acetate/methanol eluant, eluent into
Row elution, obtains A (110g), B (420g), C (700g), four components of D (100g)；By B component medicinal extract, in silica gel chromatographic column
On, with the petrol ether/ethyl acetate (1 of different gradients:0,5:1,2:1,1:1,1:2,0:1, v/v) eluant, eluent is eluted, and is obtained
To six components of B1-B6, B6 components continue on silica gel chromatographic column, with the petrol ether/ethyl acetate (1 of different gradients:0,10:
1,5:1,4:1,3:1,2:1,1:1,1:2,0:1, v/v) eluant, eluent is eluted, and nine components of B6.1-B6.9 is obtained, by B6.9
Component is recrystallized with methanol, obtains pure furanone derivatives 18.2mg.Furanone derivatives 5mg is taken, is dissolved in
The DMSO of 20mL is fitted into bottle, bottle is placed in the big bottle for filling ether solvent, is then sealed the mouth of big bottle, standing waits for
Crystal is slowly precipitated, and 3 groups of parallel laboratory test obtains the monocrystalline of the compound.
The antibacterial activity of furanone derivatives A is tested：
1, experiment material
1.1, given the test agent
Furanone derivatives are dissolved with DMSO, are made into the solution of 500 μ g/mL.
1.2, bacterial strain
Two plants of Gram-negative bacterias (Escherichia coli, Pseudomonas aeruginosa), two plants of gram-positive bacterias (staphylococcus aureus,
Streptococcus lactis).
1.3, culture medium
Beef extract 3.0g/L, NaCL 5.0g/L, peptone 10.0g/L, pH 7.0-7.5.
1.4, other materials
96 orifice plates.
2, experimental method
The 100 above-mentioned culture mediums of μ L, 100 μ L a concentration of 1 × 10 are added per hole for 96 orifice plates6The cell suspension of CFU/mL, first
The sample solution of 500 μ g/mL of Kong Zhongjia, makes sample concentration be followed successively by 500 from the first hole to the tenth hole using doubling dilution,
250,125,62.5,31.2,15.6,7.81,3.91,1.95 and 0.975 μ g/mL, 11-holes and the 12nd hole are separately added into
The above-mentioned culture mediums of 100 μ L and DMSO are as a contrast.Select positive control of the streptomycin sulphate as Gram-negative bacteria, penicillin
Positive control of the sodium as gram-positive bacteria.Above-mentioned 3 parallel laboratory tests of every group of carry out, 96 orifice plates are placed in 37 DEG C of incubators
It is incubated 24 hours.
3, experimental result
3 are the results are shown in Table, the results show that furanone derivatives have preferable inhibitory activity, MIC (minimum suppressions to streptococcus lactis
Bacteria concentration) it is 31.2 μ g/mL.
The antifungal activity of furanone derivatives A is tested：
1, experiment material
1.1, given the test agent
Furanone derivatives are dissolved with DMSO, are made into the solution of 500 μ g/mL.
1.2, bacterial strain
Seven plants of plant pathogenic fungis (apple rot pathogen, Alternaria brassicae, Exserohilum turcicum, Alternaria alternates
Bacterium, Sclerotinia sclerotiorum, botrytis cinerea, Peony Anthracnose).
1.3, culture medium
200g potato leaching juices, glucose 20g, water 1000mL.
1.4, other materials
96 orifice plates.
2, experimental method
The 100 above-mentioned culture mediums of μ L, 100 μ L a concentration of 1 × 10 are added per hole for 96 orifice plates6The cell suspension of CFU/mL, first
The sample solution of 500 μ g/mL of Kong Zhongjia, makes sample concentration be followed successively by 500 from the first hole to the tenth hole using doubling dilution,
250,125,62.5,31.2,15.6,7.81,3.91,1.95 and 0.975 μ g/mL, 11-holes and the 12nd hole are separately added into
The above-mentioned culture mediums of 100 μ L and DMSO are as a contrast.Select positive control of the carbendazim as plant pathogenic fungi.Above-mentioned every group into
96 orifice plates are placed in 28 DEG C of incubators and are incubated 48 hours by 3 parallel laboratory tests of row.
3, experimental result
3 are the results are shown in Table, the results show that furanone derivatives have preferable suppression to botrytis cinerea and tobacco brown spot pathogen
System activity, MIC (minimal inhibitory concentration) are 31.2 μ g/mL, have fairly good inhibitory activity, MIC (minimum to Alternaria brassicae
Mlc) it is 15.6 μ g/mL.
The bacteriostatic activity of 3 furanone derivatives of table
Wherein：A:Escherichia coli；B:Pseudomonas aeruginosa；C：Staphylococcus aureus；D：Streptococcus lactis；E：Apple tree is rotted
Germ；F：Alternaria brassicae；G：Exserohilum turcicum；H：Tobacco brown spot pathogen；I：Sclerotinia sclerotiorum；J：Graw mold of tomato
Bacterium；K：Peony Anthracnose；-：Experiment is not set.
Claims (9)
1. a kind of furanone derivatives, which is characterized in that the chemical structural formula of the furanone derivatives is：
2. a kind of extracting method of furanone derivatives described in claim 1, which is characterized in that include the following steps：
(1) several to be extracted from Decaisnea fargesii endogenetic fungus DS37 solid fermentations object as raw material petroleum ether, ethyl acetate and methanol
It is secondary, merge extracting solution and filter, recycle mixed solvent, filtrate decompression concentration obtains crude product medicinal extract；
(2) for the crude product medicinal extract for obtaining step (1) on silica gel chromatographic column, it is 1 to use volume gradient respectively:0:0,0:1:0,0:1:
1,0:0:1 petrol ether/ethyl acetate/methanol eluant, eluent is eluted, and tetra- components of A-D are obtained；
(3) for the B component for obtaining step (2) on silica gel chromatographic column, it is 1 to use volume gradient respectively:0,5:1,2:1,1:1,1:
2,0:1 petrol ether/ethyl acetate eluant, eluent is eluted, and six components of B1-B6 are obtained, and B6 components continue in silica gel chromatographic column
On, it is 1 with volume gradient:0,10:1,5:1,4:1,3:1,2:1,1:1,1:2,0:1 petrol ether/ethyl acetate eluant, eluent into
Row elution, obtains nine components of B6.1-B6.9, B6.9 components is recrystallized with methanol, obtain furanone derivatives.
3. a kind of extracting method of furanone derivatives according to claim 2, which is characterized in that further include step (4)：
It takes the furanone derivatives that step (3) obtains to be fitted into container A after being dissolved in DMSO, container A is placed on to the appearance for filling ether solvent
In device B, then the mouth of container B is sealed, standing waits for that crystal is precipitated, and obtains the monocrystalline of the furanone derivatives.
4. a kind of extracting method of furanone derivatives according to claim 3, which is characterized in that every in step (4)
5mg furanone derivatives are dissolved in the DMSO of 20mL.
5. a kind of extracting method of furanone derivatives according to claim 2, which is characterized in that the petroleum ether,
Ethyl acetate and methanol are industry standard.
6. a kind of extracting method of furanone derivatives according to claim 2, which is characterized in that by cat in step (1)
Product petrol ether/ethyl acetate of drying in the shade/methanol after youngster's dung endogenetic fungus DS37 solid fermentations extracts 8 times.
7. a kind of furanone derivatives described in claim 1, or pass through any one of claim 2-6 furanone derivatives
The application of furanone derivatives prepared by extracting method on antibacterial.
8. the application of furanone derivatives according to claim 7, which is characterized in that the antibacterial finger is to bacterium or fungi
Inhibiting effect.
9. the application of furanone derivatives according to claim 7, which is characterized in that it is described it is antibacterial refer to streptococcus lactis and
The inhibiting effect of Alternaria brassicae.
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| CN111559999A (en) * | 2020-03-05 | 2020-08-21 | 陕西科技大学 | Lactone compound and extraction method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111559999A (en) * | 2020-03-05 | 2020-08-21 | 陕西科技大学 | Lactone compound and extraction method and application thereof |
| CN111559999B (en) * | 2020-03-05 | 2022-02-08 | 陕西科技大学 | Lactone compound and extraction method and application thereof |
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