CN101434634B - Cholesterin derivative, as well as preparation method and application thereof - Google Patents
Cholesterin derivative, as well as preparation method and application thereof Download PDFInfo
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- CN101434634B CN101434634B CN2008102384049A CN200810238404A CN101434634B CN 101434634 B CN101434634 B CN 101434634B CN 2008102384049 A CN2008102384049 A CN 2008102384049A CN 200810238404 A CN200810238404 A CN 200810238404A CN 101434634 B CN101434634 B CN 101434634B
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- carboxyl
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- cholesterin
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Abstract
The invention discloses a cholesterol derivative with 19-bit methyl oxidized into carboxyl, and a preparation method and application thereof; during preparation, bud-dichasial junceella juncea is firstly extracted by alcohol; the extract is decompressed and concentrated to obtain an extractum; the extractum suspends in water and then extracted by an organic solvent to obtain extract liquid; after being decompressed and concentrated, the extract liquid is separated by chromatography of silicagel columns, gel chromatography and high-performance liquid phase chromatography to obtain the cholesterol derivative with 19-bit methyl oxidized into the carboxyl. The cholesterol derivative with 19-bit methyl oxidized into the carboxyl and derived from the bud-dichasial junceella juncea has stronger insecticidal activity and can be used for developing biological agricultural chemicals, thus having broad application prospect.
Description
Technical field
The present invention relates to a kind of cholesterin derivative, cholesterin derivative that particularly to relate to a kind of 19 methyl oxidations with insecticidal action be carboxyl and preparation method thereof and application.
Background technology
Since the sixties in 20th century, from gorgonian, separated the active compound obtained many novel structures, mainly comprise diterpenes, steroidal class, alkaloids etc., that its biological activity comprises is antitumor, antibiotic, antiviral, enzyme inhibition etc.The chemical constitution study of gorgonian has been become a popular domain of marine natural product research.
Up to the present, do not see relevant report both at home and abroad to the chemical ingredients of flower bud two divergent wick gorgonian Dichotella gemmacea (valenciennes).More do not see from flower bud two divergent wick gorgonians and to separate the cholesterin derivative that to obtain 19 methyl oxidations be carboxyl, do not see from other biology, to separate to obtain this derivative yet.
Summary of the invention
Cholesterin derivative that to the object of the present invention is to provide a kind of 19 methyl oxidations that derive from flower bud two divergent wick gorgonians be carboxyl and preparation method thereof with as the application of sterilant in biological pesticide, it can satisfy the demand of prior art.
A kind of 19 cholesterin derivatives that methyl oxidation is a carboxyl is characterized in that its structural formula is
R in the formula
1Be alkyl, R
2Be acyl group.
Above-mentioned 19 preparation methods that methyl oxidation is the cholesterin derivative of carboxyl is characterized in that elder generation with flower bud two divergent wick gorgonian ethanol-extracteds, obtains medicinal extract with gained extracting solution concentrating under reduced pressure, and this medicinal extract is suspended in water, and use organic solvent extraction; To use silica gel column chromatography, gel chromatography and preparative high-performance liquid chromatographic separation and purification behind the gained extraction liquid concentrating under reduced pressure, obtain 19 methyl oxidations the cholesterol compounds that is carboxyl.
The application of the cholesterin derivative that 19 above-mentioned methyl oxidations are carboxyl in preparation biological pesticide sterilant.
The present invention obtains 19 cholesterin derivatives that methyl oxidation is a carboxyl from China South Sea flower bud two divergent wick gorgonians, this derivative has insecticidal activity, can be used for developing the biological pesticide sterilant, has a extensive future.
Embodiment
When preparing compound of the present invention, take following each step:
(1) extraction of biological sample: get fresh biological sample flower bud two divergent wick gorgonian 2850g, clean, remove silt, this sample pulverizing back is used 3L 95% (mass percent, down together) ethanol lixiviate 3 times, each 1d earlier with tap water.Merge No. 3 times extracting solution, rotary evaporation is to doing, and with 2L methyl alcohol desalination 3 times, concentrating under reduced pressure gets total medicinal extract.Total medicinal extract extracts respectively 6 times with equal-volume sherwood oil, ethyl acetate and propyl carbinol after diluting with 500mL water, and the concentrating under reduced pressure extraction liquid obtains sherwood oil, ethyl acetate and propyl carbinol medicinal extract, and each medicinal extract sealing is stored in 4 ℃ of refrigerators standby.
Described ethanol can change methyl alcohol, Virahol or propyl carbinol into.
(2) separate: each extracts medicinal extract mutually extract, at first each phase medicinal extract is divided into the close several sections of polarity according to its polarity size through decompression silica gel column chromatography (VLC), separate and purifying with preparative high-performance liquid chromatographic through silica gel column chromatography, gel chromatography then, obtain compound of the present invention.The spectral data of gained compound is listed in table 1.
The nmr spectrum data of table 1 compound 1
The structural formula of the cholesterin derivative that 19 methyl oxidations that present embodiment makes are carboxyl is:
R in the formula
1Be methyl, R
2Be ethanoyl.
Compound of the present invention is to the halogen worm activity experiment that causes death:
Get artemia cysts 15mg and place the 500mL triangular flask, add the seawater 300mL that handled, slowly inflate, hatch 48h in 25 ℃ of water-baths, remove chorion and unhatched ovum, obtain artemia larvae with aerator pump, standby.
The deadly activity experiment of halogen worm is got 24 well culture plates according to the improved method of Solis, and every hole adds the solution (20 the halogen worms in every hole) of the 1mL Halogen worm young, makes the test cultures plate.With crude extract, each organic phase medicinal extract and each monomeric compound, be configured to the solution of 2mg/mL with DMS0/ water, add and cultivate in the plate hole, each crude extract and each phase medicinal extract sample are provided with 100 μ g/mL, 50 μ g/mL, three final concentrations of 10 μ g/mL, each compound is provided with 50 μ g/mL, 25 μ g/mL, three final concentrations of 10 μ g/mL.The sample of each concentration is respectively established three parallel samples again.After cultivating 24h, the dead number of record halogen worm.The deadly active corrected mortality that adopts of halogen worm is represented: corrected mortality %=[(control group survival rate-sample sets survival rate)/and the control group survival rate] * 100%
The cholesterin derivative that 19 methyl oxidations of the present invention are carboxyl is 94.4% at 50 μ g/mL to the lethality rate of halogen worm, is that lethality rate under the 25 μ g/mL is 57.9% in concentration, shows intensive halogen worm and causes death active.
Experiment shows that the cholesterin derivative that 19 methyl oxidations of the present invention are carboxyl shows strong deadly activity to the halogen worm, therefore can be with it as the biological pesticide sterilant.
Claims (3)
1. 19 cholesterin derivatives that methyl oxidation is a carboxylate methyl ester is characterized in that structural formula is
2. described 19 preparation methods that methyl oxidation is the cholesterin derivative of carboxylate methyl ester of claim 1, it is characterized in that earlier with extraction using alcohol flower bud two divergent wick gorgonians, the extracting solution concentrating under reduced pressure is obtained medicinal extract, this medicinal extract is suspended in water, use ethyl acetate extraction; To separate, obtain 19 methyl oxidations the cholesterol analog derivative that is carboxylate methyl ester behind the gained extraction liquid concentrating under reduced pressure with silica gel column chromatography, gel chromatography and preparative high-performance liquid chromatographic.
3. described 19 methyl oxidations of claim 1 application of cholesterin derivative in the preparation sterilant that be carboxylate methyl ester.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008102384049A CN101434634B (en) | 2008-12-07 | 2008-12-07 | Cholesterin derivative, as well as preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008102384049A CN101434634B (en) | 2008-12-07 | 2008-12-07 | Cholesterin derivative, as well as preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101434634A CN101434634A (en) | 2009-05-20 |
| CN101434634B true CN101434634B (en) | 2011-06-29 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2008102384049A Active CN101434634B (en) | 2008-12-07 | 2008-12-07 | Cholesterin derivative, as well as preparation method and application thereof |
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Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105613528A (en) * | 2016-02-05 | 2016-06-01 | 烟台顺隆化工科技有限公司 | Pesticide for controlling Euaresta aequalis |
| CN105519528A (en) * | 2016-02-05 | 2016-04-27 | 烟台顺隆化工科技有限公司 | Insecticide for controlling Lucilia sericata |
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2008
- 2008-12-07 CN CN2008102384049A patent/CN101434634B/en active Active
Non-Patent Citations (1)
| Title |
|---|
| 赵贞贞.2008102384049.《STN检索记录》.2010, * |
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| CN101434634A (en) | 2009-05-20 |
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