CN107118218A - The preparation method and its usage of aristolo-lactam class noval chemical compound - Google Patents
The preparation method and its usage of aristolo-lactam class noval chemical compound Download PDFInfo
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- CN107118218A CN107118218A CN201710377875.7A CN201710377875A CN107118218A CN 107118218 A CN107118218 A CN 107118218A CN 201710377875 A CN201710377875 A CN 201710377875A CN 107118218 A CN107118218 A CN 107118218A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
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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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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Abstract
The present invention relates to the preparation method and its usage in smart extraction field, more particularly to aristolo-lactam class noval chemical compound.Comprise the following steps, alcohol extracting is carried out to Aristolochia contorta, and make medicinal extract；With 2.5L distilled water by the abundant dissolved dilution of Aristolochia contorta alcohol-extracted extract of gained, chloroform 2L is extracted, and is extracted 3 times, the extract that is concentrated under reduced pressure obtains corresponding chloroform medicinal extract；Chloroform medicinal extract is through silica gel column chromatography (petroleum ether：Ethyl acetate=100：0‑0：100) after eluting, merge by tlc silica gel plate point plate, cut identical is divided into one group, obtains totally 13 groups of Fr1 13；Cut Fr5 is through silicagel column elution, petroleum ether：Acetone=92:8 obtain Fr5 2, and cut Fr5 23 is afforded through the gel columns of LH 20, then by silicagel column elution, eluent system is petroleum ether ethyl acetate, when volume ratio is 65:The compound M4 purified when 35.Make full use of Aristolochia contorta；M1, M4, M6 have good bactericidal activity.
Description
Technical field
The present invention relates to the preparation method and its use in smart extraction field, more particularly to aristolo-lactam class noval chemical compound
On the way.
Background technology
Aristolochia contorta, alias：Egg Fructus Aristolochiae, fringed iris herb, buffalo gourd basket, tea bag, stream essence, herba aristolochiae, lofty or bottomless imperial, smelly tank
Tank, smelly bell work as, hang basket, cucurbit tank, Latin literary fame：Aristolochia contorta Bunge. Aristolochiaceaes, horse pocket
Bell belongs to herbaceous species, and stem length is hairless up to more than 2 meters, has pod line after doing.Leaf papery, ovate is heart-shaped or triangular shape is heart-shaped, top
Short sharp or blunt, base portion is heart-shaped, and two side slivers are circular, sagging or extension, side full edge, above green, below light green color, the equal nothing in two sides
Hair；Yellow green when ripe, carpopodium is sagging, is ftractureed with fruit；Seed triangular shape is heart-shaped, and taupe is flat, has small wart point, light brown
Film quality wing.The month at florescence 5-7, the fruiting period 8-10 months.
The content of the invention
The purpose of invention：In order to provide a kind of preparation method of the more preferable aristolo-lactam class noval chemical compound of effect, tool
Body purpose is shown in multiple substantial technological effects of specific implementation part.
In order to reach as above purpose, the present invention is adopted the following technical scheme that：
The preparation method of aristolo-lactam class noval chemical compound, it is characterised in that comprise the following steps,
Alcohol extracting is carried out to Aristolochia contorta, and makes medicinal extract；
With 2.5L distilled water by the abundant dissolved dilution of Aristolochia contorta alcohol-extracted extract of gained, chloroform 2L is extracted, extraction
Take 3 times, the extract that is concentrated under reduced pressure obtains corresponding chloroform medicinal extract；
Chloroform medicinal extract is through silica gel column chromatography (petroleum ether：Ethyl acetate=100：0-0：100) after eluting, by thin-layer chromatography
Silica gel plate point plate merges, and cut identical is divided into one group, obtains totally 13 groups of Fr1-13；
Cut Fr5 is through silicagel column elution, petroleum ether：Acetone=92:8 obtain Fr5-2, are afforded through LH-20 gel columns
Cut Fr5-2-3, then by silicagel column elution, eluent system is petroleum ether-ethyl acetate, when volume ratio is 65:Obtained when 35
The noval chemical compound M4 of purifying.It is named as aristololactam X.
Further technical scheme of the invention is that the Aristolochia contorta pre-treatment refers to：Aristolochia contorta sample is positioned over
In baking oven, dry, the sample after drying crushed with pulverizer, obtained coarse powder alcohol soak extraction under 50 degrees celsius,
Extraction 3 times, each 24h filters leaching liquor, and filtrate decompression is concentrated to give alcohol extracting medicinal extract, merges three gained medicinal extract, places
It is standby in being refrigerated in refrigerator.
Further technical scheme of the invention is that the alcohol is methanol.
Further technical scheme of the invention is that cut Fr11 (9.25g) is through silicagel column elution, petroleum ether：Ethyl acetate
=90:10, Fr11-2 is obtained, is eluted through LH-20 gel columns, eluant, eluent is chloroform-methanol=1:1, cut Fr11-2-4 is obtained,
Again pass by LH-20 gel columns and be purified by flash and obtain noval chemical compound M6.It is named as aristololactam Y.
Further technical scheme of the invention is, cut Fr6 (15.76g) through silicagel column elution, eluant, eluent be petroleum ether-
Ethyl acetate, when volume ratio is 90:Cut Fr6-4 and cut Fr6-7 are obtained when 10, cut Fr6-4 is washed by LH-20 gel columns
De-, eluant, eluent is chloroform-methanol, and volume ratio is 1:1, purifying obtains noval chemical compound M1.It is named as aristololactamW.
One or more kinds of purposes in Colletotrichum gloeosporioides Penz in Mango is suppressed in M1, M4, M6.
A kind of material for suppressing Colletotrichum gloeosporioides Penz in Mango, it is characterised in that include the one or more in M1, M4, M6.
Using the present invention of as above technical scheme, had the advantages that relative to prior art：M1, M4, M6 have very well
Bactericidal activity, have preferable inhibition to Colletotrichum gloeosporioides Penz in Mango, fungistatic effect is obvious.
Brief description of the drawings
In order to further illustrate the present invention, it is further illustrated below in conjunction with the accompanying drawings：
Fig. 1 is the production method step schematic diagram of invention；Figprocessing in extraction and
separation of Aristolochia contorta Bunge；Note：S1：Petroleum ether：Ethyl acetate；S2：Chloroform：Methanol
=1:1；S3：Petroleum ether：Acetone；
Fig. 2 is noval chemical compound M1, M4, M6 for inventing molecular structure；
Fig. 3 is the -3from HMBC and of Key partial structures of new compounds 11H-1H
COSY data；
Fig. 4-5 composes carbon spectrogram for noval chemical compound M1 hydrogen；
Fig. 6-7 composes carbon spectrogram for noval chemical compound M4 hydrogen；
Fig. 8-9 composes carbon spectrogram for noval chemical compound M6 hydrogen；
Figure 10 is1H and 13C NMR spectroscopic data for new compounds.a；
Figure 11 is inhibitory activity form of the noval chemical compound to Colletotrichum gloeosporioides Penz in Mango.
Embodiment
The present invention is furture elucidated, it should be understood that following embodiments are merely to illustrate the present invention rather than limitation originally
The scope of invention.
(1) extract and extraction
Aristolochia contorta (10Kg) sample of purchase is positioned in baking oven, dried under 50 degrees celsius, after drying
Sample is crushed with pulverizer, obtained coarse powder (9.652Kg) methanol soak extraction, is extracted 3 times, each 24h, by leaching liquor mistake
Filter, filtrate decompression is concentrated to give methanol and extracts medicinal extract, merges three gained medicinal extract, is positioned over refrigeration in refrigerator standby.
With 2.5L distilled water by the Aristolochia contorta alcohol-extracted extract (920g) of gained fully dissolved dilution.Chloroform 2L is extracted
Take, extract 3 times, the extract that is concentrated under reduced pressure obtains corresponding chloroform medicinal extract (330g).
(2) isolate and purify
Chloroform medicinal extract (330g) is through silica gel column chromatography (petroleum ether：Ethyl acetate=100：0-0：100) after eluting, through excessively thin
Analysis silica gel plate point plate merges layer by layer, and cut identical is divided into one group, obtains totally 13 groups of Fr1-13, Fr2 (8.95g) is through silica gel column layer
Analysis, petroleum ether-ethyl acetate system elution, 65:Fr2-6 cuts are obtained when 35, Fr2-6 elutes (chlorine by LH-20 gel columns
It is imitative：Methanol=1:1) the compound M2 (27.9mg) purified, cut Fr5 (7.42g) is through silicagel column elution, petroleum ether：Third
Ketone=92:8 obtain Fr5-2, and cut Fr5-2-3 is afforded through LH-20 gel columns, then by silicagel column elution, eluent system
For petroleum ether-ethyl acetate, when volume ratio is 65:The compound M4 (28.2mg) purified when 35, cut Fr6 (15.76g)
Through silicagel column elution, eluant, eluent is petroleum ether-ethyl acetate, when volume ratio is 90:Cut Fr6-4 and cut Fr6- are obtained when 10
7, cut Fr6-4 are eluted by LH-20 gel columns, and eluant, eluent is chloroform-methanol, and volume ratio is 1:1, purifying obtains compound M1
(10.4mg), cut Fr6-7 is through silicagel column elution, and eluent petroleum ether-ethyl acetate, volume ratio is 4:Purifyingization when 1
Compound M3 (4.6mg), cut Fr9 (12.58g) is through silicagel column elution, petroleum ether：Ethyl acetate=85:15, Fr9-3 is obtained, is passed through
LH-20 gel columns are eluted, and eluant, eluent is chloroform-methanol=1:1, cut Fr9-3-5 is obtained, then by silica gel column chromatography elution,
Eluant, eluent is petroleum ether-ethyl acetate, and volume ratio is 70:Purifying obtains compound M5 (3.2mg) when 30.Cut Fr11
(9.25g) is through silicagel column elution, petroleum ether：Ethyl acetate=90:10, Fr11-2 is obtained, is eluted through LH-20 gel columns, elution
Agent is chloroform-methanol=1:1, cut Fr11-2-4 is obtained, LH-20 gel columns is again passed by and is purified by flash and obtain compound M6
(15.7mg) and M7 (4.2mg).
Mycelial growth rate method determines bacteriostatic activity of the noval chemical compound to Colletotrichum gloeosporioides Penz in Mango, and test concentrations are 75 μ g/mL.
Testing sample is dissolved with 0.2 μ L dimethyl sulfoxide (DMSO), plus sterilized water is diluted to concentration 1.5mg/mL, take 1mL with
After the quantitative PDA culture medium mixing of 19mL sterilizings, pour into and the malicious culture medium of band is made in a diameter of 6cm culture dishes, in triplicate.With
It is control to add the dimethyl sulphoxide solution of same amount.With diameter 5mm card punch cultured for examination disease fungus bacterium colony
Edge cuts bacteria cake reversal connection in culture medium, and 25 DEG C of culture 60h, with crossing method measurement bacterium colony extension diameter, obtain mycelia
Growth inhibition ratio.
As a result Fig. 6 is seen.When concentration is 75 μ g/mL, noval chemical compound M1 and M6 has certain suppression to Colletotrichum gloeosporioides Penz in Mango
Effect, and noval chemical compound M4 has preferable inhibition to Colletotrichum gloeosporioides Penz in Mango, substantially, bacteriostasis rate reaches fungistatic effect
41.44%.
General principle, principal character and the advantages of the present invention of the present invention has been shown and described above.The technology of this area
Personnel should be recognized that the present invention is not limited to the above embodiments, simply illustrate this hair described in above-described embodiment and specification
Bright principle, without departing from the spirit and scope of the present invention, various changes and modifications of the present invention are possible, these changes
Both fallen within improving in claimed scope.
Claims (8)
1. the preparation method of aristolo-lactam class noval chemical compound, it is characterised in that comprise the following steps,
Alcohol extracting is carried out to Aristolochia contorta, and makes medicinal extract；
With 2.5L distilled water by the abundant dissolved dilution of Aristolochia contorta alcohol-extracted extract of gained, chloroform 2L is extracted, extraction 3
Secondary, the extract that is concentrated under reduced pressure obtains corresponding chloroform medicinal extract；
Chloroform medicinal extract is through silica gel column chromatography (petroleum ether：Ethyl acetate=100：0-0：100) after eluting, by tlc silica gel
Plate point plate merges, and cut identical is divided into one group, obtains totally 13 groups of Fr1-13；
Cut Fr5 is through silicagel column elution, petroleum ether：Acetone=92:8 obtain Fr5-2, and cut is afforded through LH-20 gel columns
Fr5-2-3, then by silicagel column elution, eluent system is petroleum ether-ethyl acetate, when volume ratio is 65:Purified when 35
Noval chemical compound M4.
2. the preparation method of aristolo-lactam class noval chemical compound as claimed in claim 1, it is characterised in that the northern horse pocket
Bell pre-treatment refers to：Aristolochia contorta sample is positioned in baking oven, dried under 50 degrees celsius, by the sample powder after drying
Broken machine is crushed, obtained coarse powder alcohol soak extraction, is extracted 3 times, each 24h filters leaching liquor, filtrate decompression is concentrated to give
Alcohol extracting medicinal extract, merges three gained medicinal extract, is positioned over refrigeration in refrigerator standby.
3. the preparation method of aristolo-lactam class noval chemical compound as claimed in claim 2, it is characterised in that the alcohol is first
Alcohol.
4. the preparation method of aristolo-lactam class noval chemical compound as claimed in claim 1, it is characterised in that cut Fr11
(9.25g) is through silicagel column elution, petroleum ether：Ethyl acetate=90:10, Fr11-2 is obtained, is eluted through LH-20 gel columns, elution
Agent is chloroform-methanol=1:1, cut Fr11-2-4 is obtained, LH-20 gel columns is again passed by and is purified by flash and obtain noval chemical compound
M6。
5. the preparation method of the aristolo-lactam class noval chemical compound as described in claim 1 or 4, it is characterised in that cut
Fr6 (15.76g) is through silicagel column elution, and eluant, eluent is petroleum ether-ethyl acetate, when volume ratio is 90:Cut Fr6- is obtained when 10
4 and cut Fr6-7, cut Fr6-4 are eluted by LH-20 gel columns, and eluant, eluent is chloroform-methanol, and volume ratio is 1:1, purifying
Obtain noval chemical compound M1.
One or more kinds of purposes in Colletotrichum gloeosporioides Penz in Mango is suppressed in 6.M1, M4, M6.
7. a kind of material for suppressing Colletotrichum gloeosporioides Penz in Mango, it is characterised in that include the one or more in M1, M4, M6.
8. purposes of the Aristolochia contorta in the medicament for suppressing Colletotrichum gloeosporioides Penz in Mango.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107354747A (en) * | 2017-08-03 | 2017-11-17 | 东莞市联洲知识产权运营管理有限公司 | It is a kind of using Aristolochia contorta as fabric finishing agent of raw material and preparation method thereof |
| CN107602575A (en) * | 2017-09-19 | 2018-01-19 | 海南大学 | The aristolochic acid of effective preventing and treating Meloidogyne incognita and its separating screening method of derivatives quasi-compound of a kind of potential green |
| CN109232384A (en) * | 2018-09-05 | 2019-01-18 | 海南师范大学 | Aristolo-lactam class compound and its preparation method and application |
| CN109232378A (en) * | 2018-09-05 | 2019-01-18 | 海南师范大学 | The aristolo-lactam class compound with antibacterial activity and its preparation method and application extracted from beak fruit soap badge on a cap |
| CN111620809A (en) * | 2020-06-29 | 2020-09-04 | 海南师范大学 | Aristolochia lactam compound and preparation method and application thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107354747A (en) * | 2017-08-03 | 2017-11-17 | 东莞市联洲知识产权运营管理有限公司 | It is a kind of using Aristolochia contorta as fabric finishing agent of raw material and preparation method thereof |
| CN107602575A (en) * | 2017-09-19 | 2018-01-19 | 海南大学 | The aristolochic acid of effective preventing and treating Meloidogyne incognita and its separating screening method of derivatives quasi-compound of a kind of potential green |
| CN107602575B (en) * | 2017-09-19 | 2019-12-03 | 海南大学 | The aristolochic acid for effectively preventing Meloidogyne incognita of a kind of potential green and its separating screening method of derivatives quasi-compound |
| CN109232384A (en) * | 2018-09-05 | 2019-01-18 | 海南师范大学 | Aristolo-lactam class compound and its preparation method and application |
| CN109232378A (en) * | 2018-09-05 | 2019-01-18 | 海南师范大学 | The aristolo-lactam class compound with antibacterial activity and its preparation method and application extracted from beak fruit soap badge on a cap |
| CN109232384B (en) * | 2018-09-05 | 2022-06-21 | 海南师范大学 | Aristolochia lactam compound and preparation method and application thereof |
| CN109232378B (en) * | 2018-09-05 | 2022-08-02 | 海南师范大学 | Aristolochia lactam compound extracted from Zanthoxylum rostratum and having antibacterial activity, and its preparation method and application |
| CN111620809A (en) * | 2020-06-29 | 2020-09-04 | 海南师范大学 | Aristolochia lactam compound and preparation method and application thereof |
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| CN107118218B (en) | 2019-08-06 |
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