CN107118218B - 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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- CN107118218B CN107118218B CN201710377875.7A CN201710377875A CN107118218B CN 107118218 B CN107118218 B CN 107118218B CN 201710377875 A CN201710377875 A CN 201710377875A CN 107118218 B CN107118218 B CN 107118218B
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- 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 smart extraction field more particularly to the preparation method and its usages of aristolo-lactam class noval chemical compound.It comprises the following steps, alcohol extracting is carried out to Aristolochia contorta, and make medicinal extract；With the distilled water of 2.5L by the resulting abundant dissolved dilution of Aristolochia contorta alcohol-extracted extract, chloroform 2L is extracted, and is extracted 3 times, and extract liquor is concentrated under reduced pressure and obtains corresponding chloroform medicinal extract；Chloroform medicinal extract merges, fraction is identical to be divided into one group, obtains 13 groups of Fr1-13 totally after silica gel column chromatography (petroleum ether: ethyl acetate=100:0-0:100) elution by tlc silica gel plate contact plate；Fraction Fr5 is through silicagel column elution, and petroleum ether: acetone=92:8 obtains Fr5-2, affords fraction Fr5-2-3 through LH-20 gel column, and using silicagel column elution, eluent system is petroleum ether-ethyl acetate, the compound M4 purified when volume ratio is 65:35.Make full use of Aristolochia contorta；M1, M4, M6 have good bactericidal activity.
Description
Technical field
The present invention relates to smart extraction field more particularly to the preparation methods and its use of aristolo-lactam class noval chemical compound
On the way.
Background technique
Aristolochia contorta, alias: egg Fructus Aristolochiae, fringed iris herb, buffalo gourd basket, tea bag, stream essence, herba aristolochiae, lofty or bottomless dragon, smelly tank
Tank, smelly bell work as, hang basket, cucurbit tank, Latin literary fame: Aristolochia contorta Bunge. Aristolochiaceae, horse pocket
Bell category herbaceous species, stem length is hairless up to 2 meters or more, Gan Houyou cannelure line.Leaf papery, ovate is heart-shaped or triangular shape is heart-shaped, top
Short point or blunt, base portion is heart-shaped, and two side slivers are round, sagging or extension, Bian Quanyuan, above green, below light green color, the equal nothing in two sides
Hair；Yellow green when mature, carpopodium is sagging, cracks 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 month.
Summary of the invention
The purpose of invention: in order to provide a kind of preparation method of better 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 purpose as above, the present invention is adopted the following technical scheme that:
The preparation method of aristolo-lactam class noval chemical compound, which is characterized in that comprise the following steps, to Aristolochia contorta into
Row alcohol extracting, and make medicinal extract；
With the distilled water of 2.5L by the resulting abundant dissolved dilution of Aristolochia contorta alcohol-extracted extract, chloroform 2L is extracted, extraction
It takes 3 times, extract liquor is concentrated under reduced pressure and obtains corresponding chloroform medicinal extract；
Chloroform medicinal extract is after silica gel column chromatography (petroleum ether: ethyl acetate=100:0-0:100) elution, by thin-layer chromatography
Silica gel plate contact plate merges, and fraction is identical to be divided into one group, obtains totally 13 groups of Fr1-13；
Fraction Fr5 is through silicagel column elution, and petroleum ether: acetone=92:8 obtains Fr5-2, affords through LH-20 gel column
Fraction Fr5-2-3, using silicagel column elution, eluent system is petroleum ether-ethyl acetate, is obtained when volume ratio is 65:35
The noval chemical compound M4 of purifying.It is named as aristololactamX.
The further technical solution of the present invention is that the Aristolochia contorta pre-treatment refers to: Aristolochia contorta sample is placed in
It in baking oven, is dried under 50 degrees celsius, the sample after drying is crushed with pulverizer, obtained coarse powder alcohol soak extraction,
Extraction 3 times, every time for 24 hours, leaching liquor is filtered, and filtrate decompression is concentrated to get alcohol extracting medicinal extract, is merged gained medicinal extract three times, is placed
It is spare in being refrigerated in refrigerator.
The further technical solution of the present invention is that the alcohol is methanol.
The further technical solution of the present invention is that fraction Fr11 (9.25g) is through silicagel column elution, petroleum ether: ethyl acetate
=90:10, obtains Fr11-2, elutes through LH-20 gel column, and eluant, eluent is chloroform-methanol=1:1, obtains fraction Fr11-2-4,
LH-20 gel column is again passed by be purified by flash to obtain noval chemical compound M6.It is named as aristololactamY.
The further technical solution of the present invention is that for fraction Fr6 (15.76g) through silicagel column elution, eluant, eluent is petroleum ether-
Ethyl acetate, fraction Fr6-4 and fraction Fr6-7 are obtained when volume ratio is 90:10, and fraction Fr6-4 is washed by LH-20 gel column
De-, eluant, eluent is chloroform-methanol, and volume ratio 1:1 is purified and obtained noval chemical compound M1.It is named as aristololactamW.
One or more of M1, M4, M6 are inhibiting the purposes in Colletotrichum gloeosporioides Penz in Mango.
A kind of substance inhibiting Colletotrichum gloeosporioides Penz in Mango, which is characterized in that include one or more of M1, M4, M6.
Using the present invention of technical solution as above, have the advantages that compared with the existing technology: M1, M4, M6 have very well
Bactericidal activity, have preferable inhibitory effect to Colletotrichum gloeosporioides Penz in Mango, fungistatic effect is obvious.
Detailed description of the invention
In order to further illustrate the present invention, it is further illustrated with reference to the accompanying drawing:
Fig. 1 is the production method steps schematic diagram of invention；The extraction and separation process of Aristolochia contorta；Note: S1: petroleum ether:
Ethyl acetate；S2: chloroform: methanol=1:1；S3: petroleum ether: acetone；
Fig. 2 is the molecular structure of noval chemical compound M1, M4, M6 of invention；
Fig. 3 be from HMBC and1H-1The key component structure for the noval chemical compound 1-3 that H COSY data are got；
The hydrogen that Fig. 4-5 is noval chemical compound M1 composes carbon spectrogram；
The hydrogen that Fig. 6-7 is noval chemical compound M4 composes carbon spectrogram；
The hydrogen that Fig. 8-9 is noval chemical compound M6 composes carbon spectrogram；
Figure 10 is noval chemical compound1H and13C spectroscopic data of the nuclear magnetic resonance；1H-NMR (hydrogen spectrum) data are that 400MHz is measured
,13C-NMR (carbon spectrum) data are that 100MHz is measured, and the spectral data of M1 and M4 are to use CDCl3Dissolution measurement, the wave of M6
Modal data is to be dissolved to measure with DMSO-d6；
Figure 11 is inhibitory activity table of the noval chemical compound to Colletotrichum gloeosporioides Penz in Mango.
Specific embodiment
The present invention is furture elucidated, it should be understood that following specific embodiments are merely to illustrate the present invention rather than limitation originally
The range of invention.
(1) it extracts and extracts
Aristolochia contorta (10Kg) sample of purchase is placed in baking oven, is dried under 50 degrees celsius, after drying
Sample is crushed with pulverizer, obtained coarse powder (9.652Kg) methanol soak extraction, is extracted 3 times, every time for 24 hours, by leaching liquor mistake
Filter, filtrate decompression are concentrated to get methanol and extract medicinal extract, merge gained medicinal extract three times, and it is spare to be placed in refrigeration in refrigerator.
With the distilled water of 2.5L by the abundant dissolved dilution of resulting Aristolochia contorta alcohol-extracted extract (920g).Chloroform 2L is extracted
It takes, extracts 3 times, extract liquor is concentrated under reduced pressure and obtains corresponding chloroform medicinal extract (330g).
(2) it isolates and purifies
Chloroform medicinal extract (330g) is after silica gel column chromatography (petroleum ether: ethyl acetate=100:0-0:100) elution, through excessively thin
Analysis silica gel plate contact plate merges layer by layer, and fraction is identical to be divided into one group, obtains totally 13 groups of Fr1-13, Fr2 (8.95g) is through silica gel column layer
Analysis, the elution of petroleum ether-ethyl acetate system obtain Fr2-6 fraction in 65:35, and Fr2-6 elutes (chlorine by LH-20 gel column
It is imitative: methanol=1:1) the compound M2 (27.9mg) that is purified, fraction Fr5 (7.42g) is through silicagel column elution, petroleum ether: third
Ketone=92:8 obtains Fr5-2, fraction Fr5-2-3 is afforded through LH-20 gel column, using silicagel column elution, eluent system
For petroleum ether-ethyl acetate, the compound M4 (28.2mg), fraction Fr6 (15.76g) purified when volume ratio is 65:35
Through silicagel column elution, eluant, eluent is petroleum ether-ethyl acetate, obtains fraction Fr6-4 and fraction Fr6- when volume ratio is 90:10
7, fraction Fr6-4 are eluted by LH-20 gel column, and eluant, eluent is chloroform-methanol, and volume ratio 1:1 is purified and obtained compound M1
(10.4mg), fraction Fr6-7 is through silicagel column elution, eluent petroleum ether-ethyl acetate, purifying when volume ratio is 4:1
It closes object M3 (4.6mg), fraction Fr9 (12.58g) is through silicagel column elution, and petroleum ether: ethyl acetate=85:15 obtains Fr9-3, warp
The elution of LH-20 gel column, eluant, eluent are chloroform-methanol=1:1, obtain fraction Fr9-3-5, elute using silica gel column chromatography,
Eluant, eluent is petroleum ether-ethyl acetate, and volume ratio purifies to obtain compound M5 (3.2mg) when being 70:30.Fraction Fr11
(9.25g) through silicagel column elution, petroleum ether: ethyl acetate=90:10 obtains Fr11-2, elutes through LH-20 gel column, elution
Agent is chloroform-methanol=1:1, obtains fraction Fr11-2-4, again passes by LH-20 gel column and be purified by flash to obtain compound M6
(15.7mg) and M7 (4.2mg).
Mycelial growth rate method measures noval chemical compound to the bacteriostatic activity of Colletotrichum gloeosporioides Penz in Mango, and test concentrations are 75 μ g/mL.
Sample to be tested is dissolved with the dimethyl sulfoxide of 0.2 μ L, sterile water is added to be diluted to concentration 1.5mg/mL, take 1mL with
After the quantitative PDA culture medium mixing of 19mL sterilizing, pouring into diameter is that the malicious culture medium of band is made in 6cm culture dish, in triplicate.With
The dimethyl sulphoxide solution that same amount is added is control.With the punch of diameter 5mm cultured for trying disease fungus bacterium colony
Edge cuts bacteria cake reversal connection in culture medium, and 25 DEG C of culture 60h extend diameter with crossing method measurement bacterium colony, find out mycelia
Growth inhibition ratio.
As a result see Fig. 6.When concentration is 75 μ g/mL, noval chemical compound M1 and M6 has certain inhibition to Colletotrichum gloeosporioides Penz in Mango
Effect, and noval chemical compound M4 has preferable inhibitory effect to Colletotrichum gloeosporioides Penz in Mango, fungistatic effect is obvious, and bacteriostasis rate reaches
41.44%.
The basic principles, main features and advantages of the present invention have been shown and described above.The technology of this field
Personnel should be recognized that the present invention is not limited to the above embodiments, and the above embodiments and description only describe this hairs
Bright principle, without departing from the spirit and scope of the present invention, various changes and improvements may be made to the invention, these variations
It is both fallen in claimed range with improving.
Claims (5)
1. the preparation method of aristolo-lactam class noval chemical compound, which is characterized in that it comprises the following steps,
Alcohol extracting is carried out to Aristolochia contorta, and makes medicinal extract；
With the distilled water of 2.5L by the resulting abundant dissolved dilution of Aristolochia contorta alcohol-extracted extract, chloroform 2L is extracted, extraction 3
It is secondary, extract liquor is concentrated under reduced pressure and obtains corresponding chloroform medicinal extract；
Chloroform medicinal extract is through silica gel column chromatography, petroleum ether: after ethyl acetate -100:0-0:100 elution, by tlc silica gel plate
Contact plate merges, and fraction is identical to be divided into one group, obtains totally 13 groups of Fr1-13；
Fraction Fr5 is through silicagel column elution, and petroleum ether: acetone -92:8 obtains Fr5-2, affords fraction through LH-20 gel column
Fr5-2-3, using silicagel column elution, eluent system is petroleum ether-ethyl acetate, is purified when volume ratio is 65:35
Noval chemical compound M4, M4 be
2. the preparation method of aristolo-lactam class noval chemical compound as described in claim 1, which is characterized in that also comprising to horse
Pocket bell carries out the step of pre-treatment, and the Aristolochia contorta pre-treatment refers to: Aristolochia contorta sample being placed in baking oven, 50 is Celsius
It is dried under the conditions of degree, the sample after drying is crushed with pulverizer, obtained coarse powder alcohol soak extraction, extraction 3 times, every time
For 24 hours, leaching liquor is filtered, filtrate decompression is concentrated to get alcohol extracting medicinal extract, merges gained medicinal extract three times, is placed in refrigeration in refrigerator
It is spare.
3. the preparation method of aristolo-lactam class noval chemical compound as claimed in claim 2, which is characterized in that the alcohol is first
Alcohol.
4.Purposes in the drug that preparation inhibits Colletotrichum gloeosporioides Penz in Mango.
5. a kind of substance for inhibiting Colletotrichum gloeosporioides Penz in Mango, which is characterized in that it is
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| 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 |
| 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 |
| CN109232384B (en) * | 2018-09-05 | 2022-06-21 | 海南师范大学 | Aristolochia lactam compound and preparation method and application thereof |
| 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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| AU2003903909A0 (en) * | 2003-07-25 | 2003-08-07 | Albright & Wilson (Australia) Limited | Production methods |
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| CN101401850A (en) * | 2008-11-11 | 2009-04-08 | 江西本草天工科技有限责任公司 | Piper hancei total alkaloid extract and uses thereof |
| CN102247357A (en) * | 2011-05-19 | 2011-11-23 | 中国人民解放军第二军医大学 | Application of uvarilactam and aristololactam BI in preparation of anticancer medicaments |
| CN106083868A (en) * | 2016-06-13 | 2016-11-09 | 海南大学 | Murraya microphylla branch active component and application thereof |
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