CN1049091C - Preparation technology for nimbin - Google Patents
Preparation technology for nimbin Download PDFInfo
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- CN1049091C CN1049091C CN96112529A CN96112529A CN1049091C CN 1049091 C CN1049091 C CN 1049091C CN 96112529 A CN96112529 A CN 96112529A CN 96112529 A CN96112529 A CN 96112529A CN 1049091 C CN1049091 C CN 1049091C
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- water
- nimbin
- extraction
- ethyl acetate
- methyl alcohol
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Abstract
The present invention provides a technology with the advantages of different from the prior art, simple process, low cost, high yield and stable product for preparing nimbin from neem plants, which comprises: using kernels of the neem plants as raw materials, and then orderly processing through the steps of degreasing, extraction distribution, separation on columns, etc., wherein the step of extraction distribution comprises: firstly extracting for 1 to 3 times through soaking in a solution containing methanol and water in the proportion of 4:1 to 9:1 or refluxing, recovering the filtering solution, and then extracting by ethyl acetate in a methanol layer containing the water; the step of separation on columns comprises: processing on a silica gel column for 1 to 2 times through an ethyl acetate layer, processing on a medium pressure column MPLC later, eluting by a solution containing chloroform and propanone in the proportion of 9:1, finally processing through a Rp18 reversed-phase column, and then eluting by a solution containing the methanol and the water in the proportion of 1:1 to obtain the nimbin.
Description
The invention belongs to the natural insecticide field, particularly, relate to the technology of from natural plants, extracting insecticide.
Along with people for some intrinsic characteristics of synthetic pesticide; as contaminated environment, kill and wound nature, understanding that residue is big to the person poultry toxicity; people are to the enhancing of the protection consciousness of self-living environment; natural insecticide is more and more had an optimistic view of by people; natural insecticide active substance is all actively being sought in countries in the world from plant; the research that annual agrochemistry expense in the world has half to be used for insecticide approximately, its importance is conspicuous.Seal chinaberry (Azadirachta indica) plant is a kind of plant green for a long time with very strong insecticidal activity in the Meliaceae plant, is highly active antifeedant for insect and therefrom extract the nimbin for preparing, and its insecticidal activity was familiar with by people before half a century greatly.Systematic science ground research seal chinaberry originates in the latter stage sixties, is a focus of natural insecticide research so far always.External natural product chemistry researcher with seal chinaberry each several part isolation identification a compound surplus 100, and made many biological activity determinations, wherein the strongest with the nimbin activity, be commonly used to evaluation criterion as natural insecticidal activity.The existing report of separation and Extraction nimbin technology from seal chinaberry plant, but there is the flow process complexity, the cost costliness, yield is lower, shortcomings such as products obtained therefrom instability, as E.C. Uebel etc. at Journal of Liquid Chromatography 2 (6) 875-882 (1979), R.BRYAN YAMASAKI is at Journal of Chromatography 356 (1986) 220-226, the technology that W.Kraus reports in Tetrahedron VOL 43 No.12 2828 (1987), all adopt relatively more expensive separation agent and material, as reagent such as acetonitriles, the HPLC of preparation property etc., yield all is less than 0.02%.
The object of the present invention is to provide a kind of unlike the prior art, the technology of from the seal chinaberry, extracting nimbin that flow process is simple, with low cost, yield is higher, product is stable.
The object of the present invention is achieved like this: the kind benevolence with seal chinaberry plant is raw material, makes nimbin with degreasing, extraction distribution, upper prop separating step successively, said degreasing benzinum cold soaking 1-3 time; Said extraction distributes uses earlier methyl alcohol: water 4: 1-9: 1 immersion or refluxing extraction 1-3 time, and filtrate is reclaimed, and uses ethyl acetate extraction in the aqueous methanol layer; Said upper prop separates with silicagel column on ethyl acetate layer 1-2 time, goes up middle compression leg MPLC then, with chloroform: 9: 1 wash-outs of acetone, pass through the Rp18 reversed-phase column at last, with methyl alcohol: 1: 1 wash-out of water get final product nimbin.
In the above-mentioned technology, extract to distribute and can preferably use methyl alcohol: water 6: 1-9: 1 soaks 3 times.
In the above-mentioned technology, extract to distribute and preferably to use methyl alcohol: water 6: 1-9: 1 refluxing extraction 3 times.
Compared with prior art, the beneficial effect of the present invention's existence is as follows:
1, because the present invention adopts ethyl acetate extraction in the extraction allocation step of technology, replaced prior art with chloroform extraction, directly go up the step of HPLC, thereby the solvent cost of using is low, is common solvent, has overcome the shortcoming that makes unstable products with chloroform simultaneously;
2, the present invention on the upper prop separating step has increased in compression leg MPLC step, make efficiency of pcr product reach 0.18%, all higher than prior art yield, as than E.C.Vebel high ten times of the yield of Journal of LiguidChromatagraphy 2 (6) 875 (1979) report, than R BRYAN YAMASAKI high tens of times of the yield of Jouranal of Chromatography 356 (1986) 220-226 report, than W.Kraus also high tens of times of the yield of Tetrahedron VOL 43 No.12 2817 (1987) reports; And product do not change, and stability increases greatly, and it is low to have overcome the prior art efficiency of pcr product, unstable products simultaneously, easily change (as by nimbin (Azadirachtin) configuration to nimbin isomer (Azadirachtinin) transformation) shortcoming.
In order to understand essence of the present invention better, describe technology contents of the present invention in detail with embodiment below, but content of the present invention is not limited thereto.
Embodiment one:
Get seal chinaberry (Azadirachta indica) and plant benevolence 10kg pulverizing, with benzinum cold soaking 3 times, filter residue methyl alcohol: water soaks 3 time at 4: 1, filtrate is reclaimed, in the aqueous methanol layer, use ethyl acetate extraction, silicagel column on the ethyl acetate layer with petroleum ether-ethyl acetate (1: 1) wash-out, is collected with the 250ml/ bottle, with silicagel column on the 21-29 bottle, with benzinum-acetone (2: 1) wash-out, collect with the 50ml/ bottle, with middle compression leg MPLC on the 23-42 bottle, with chloroform: 9: 1 wash-outs of acetone, collect with the 50ml/ bottle, with the 7-13 bottle through the Rp18 reversed-phase column, with methyl alcohol: 1: 1 wash-out of water get final product nimbin 18 grams.
Embodiment two:
Get seal chinaberry (Azadirachta indica) and plant benevolence 20kg pulverizing, with benzinum cold soaking 2 times, filter residue methyl alcohol: water soaks 2 time at 9: 1, filtrate is reclaimed, in the aqueous methanol layer, use ethyl acetate extraction, silicagel column on the ethyl acetate layer with petroleum ether-ethyl acetate (1: 1) wash-out, is collected with the 250ml/ bottle, with silicagel column on the 21-29 bottle, with benzinum-acetone (2: 1) wash-out, collect with the 50ml/ bottle, with middle compression leg MPLC on the 23-42 bottle, with chloroform: 9: 1 wash-outs of acetone, collect with the 50ml/ bottle, with the 7-13 bottle through the Rp18 reversed-phase column, with methyl alcohol: 1: 1 wash-out of water get final product nimbin 36 grams.
Embodiment three:
Get seal chinaberry (Azadirachta indica) and plant benevolence 10kg pulverizing, with benzinum cold soaking 3 times, filter residue methyl alcohol: 4: 1 refluxing extraction of water 3 times, filtrate is reclaimed, in the aqueous methanol layer, use ethyl acetate extraction, silicagel column on the ethyl acetate layer with petroleum ether-ethyl acetate (1: 1) wash-out, is collected with the 250ml/ bottle, with silicagel column on the 21-29 bottle, with benzinum-acetone (2: 1) wash-out, collect with the 50ml/ bottle, with middle compression leg MPLC on the 23-42 bottle, with chloroform: 9: 1 wash-outs of acetone, collect with the 50ml/ bottle, with the 7-13 bottle through the Rp18 reversed-phase column, with methyl alcohol: 1: 1 wash-out of water get final product nimbin 18 grams.
Embodiment four:
Get seal chinaberry (Azadirachta indica) and plant benevolence 30kg pulverizing, with benzinum cold soaking 1 time, filter residue methyl alcohol: water soaks 2 time at 8: 1, filtrate is reclaimed, in the aqueous methanol layer, use ethyl acetate extraction, silicagel column on the ethyl acetate layer with petroleum ether-ethyl acetate (1: 1) wash-out, is collected with the 250ml/ bottle, with silicagel column on the 21-29 bottle, with benzinum-acetone (2: 1) wash-out, collect with the 50ml/ bottle, with middle compression leg MPLC on the 23-42 bottle, with chloroform: 9: 1 wash-outs of acetone, collect with the 50ml/ bottle, with the 7-13 bottle through the Rp18 reversed-phase column, with methyl alcohol: 1: 1 wash-out of water get final product nimbin 52 grams.
Embodiment five:
Get seal chinaberry (Azadirachta indica) and plant benevolence 10kg pulverizing, with benzinum cold soaking 3 times, filter residue methyl alcohol: water soaks 3 time at 6: 1, filtrate is reclaimed, in the aqueous methanol layer, use ethyl acetate extraction, silicagel column on the ethyl acetate layer is with petroleum ether-ethyl acetate (1: 1). wash-out, collect with the 250ml/ bottle, with silicagel column on the 21-29 bottle, with benzinum-acetone (2: 1) wash-out, collect with the 50ml/ bottle, with middle compression leg MPLC on the 23-42 bottle, with chloroform: 9: 1 wash-outs of acetone, collect with the 50ml/ bottle, with the 7-13 bottle through the Rp18 reversed-phase column, with methyl alcohol: 1: 1 wash-out of water get final product nimbin 19 grams.
Claims (3)
1, a kind of technology of from the seal chinaberry, extracting nimbin, with the neem kernel is raw material, make nimbin with degreasing, extraction distribution, upper prop separating step successively, said degreasing benzinum cold soaking 1-3 time, it is characterized in that said extraction distributes elder generation's methyl alcohol: water 4: 1-9: 1 immersion or refluxing extraction 1-3 time, filtrate is reclaimed, and uses ethyl acetate extraction in the aqueous methanol layer; Said upper prop separates with silicagel column on ethyl acetate layer 1-2 time, goes up middle compression leg MPLC then, with chloroform: 9: 1 wash-outs of acetone, pass through the Rp18 reversed-phase column at last, with methyl alcohol: 1: 1 wash-out of water get final product nimbin.
2, extraction process according to claim 1, it is characterized in that extracting distributing and preferably use methyl alcohol: water 6: 1-9: 1 soaks 3 times.
3, extraction process according to claim 1 is characterized in that extracting distributing and preferably uses methyl alcohol: water 6: 1-9: 1 refluxing extraction 3 times.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN96112529A CN1049091C (en) | 1996-09-06 | 1996-09-06 | Preparation technology for nimbin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN96112529A CN1049091C (en) | 1996-09-06 | 1996-09-06 | Preparation technology for nimbin |
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| Publication Number | Publication Date |
|---|---|
| CN1149397A CN1149397A (en) | 1997-05-14 |
| CN1049091C true CN1049091C (en) | 2000-02-09 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN96112529A Expired - Fee Related CN1049091C (en) | 1996-09-06 | 1996-09-06 | Preparation technology for nimbin |
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| Country | Link |
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Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1094040C (en) * | 1999-05-28 | 2002-11-13 | 华南农业大学 | Nimbin mixed pesticide preparation and its preparing method |
| CN100342787C (en) * | 2004-07-28 | 2007-10-17 | 中国科学院生态环境研究中心 | Combination of insect disinfectations containing benzoate of Avermectin in methylamine group and azadirachtin |
| CN101029276B (en) * | 2006-03-03 | 2010-12-22 | 中国林业科学研究院资源昆虫研究所 | Fast method for continuouslly extracting nim oil and nimbin raw medicine from nim seed |
| CN102887911A (en) * | 2012-11-06 | 2013-01-23 | 白林 | Azadirachtin extraction method |
| CN115462391A (en) * | 2022-08-25 | 2022-12-13 | 宁夏农林科学院植物保护研究所（宁夏植物病虫害防治重点实验室） | Agricultural insecticidal composition and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4943434A (en) * | 1987-10-06 | 1990-07-24 | Rohm And Haas Company | Insecticidal hydrogenated neem extracts |
| US5047242A (en) * | 1987-03-04 | 1991-09-10 | Native Plant Institute ("Npi") | Azadirachtin derivative insecticides |
| EP0581467A1 (en) * | 1992-07-27 | 1994-02-02 | Rohm And Haas Company | Stable extracts from neem seeds |
| DE4342625A1 (en) * | 1993-12-14 | 1995-06-22 | Max Planck Gesellschaft | Powdered Meliaceae extracts useful as insecticides |
-
1996
- 1996-09-06 CN CN96112529A patent/CN1049091C/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5047242A (en) * | 1987-03-04 | 1991-09-10 | Native Plant Institute ("Npi") | Azadirachtin derivative insecticides |
| US4943434A (en) * | 1987-10-06 | 1990-07-24 | Rohm And Haas Company | Insecticidal hydrogenated neem extracts |
| EP0581467A1 (en) * | 1992-07-27 | 1994-02-02 | Rohm And Haas Company | Stable extracts from neem seeds |
| CN1084354A (en) * | 1992-07-27 | 1994-03-30 | 罗姆和哈斯公司 | Stable extracts from neem seeds |
| DE4342625A1 (en) * | 1993-12-14 | 1995-06-22 | Max Planck Gesellschaft | Powdered Meliaceae extracts useful as insecticides |
Non-Patent Citations (3)
| Title |
|---|
| JOURMAL OF CHRMATOGPHY VOL356 1986.1.1 R.BRYAN YAMASAKI ET AL ISOLATION AND PURIFICATON OF AZADIRACHTIN FROM NEEM SEEDS USING FLASH CHNOMAT * |
| JOURMAL OF CHRMATOGPHY VOL356 1986.1.1 R.BRYAN YAMASAKI ET AL ISOLATION AND PURIFICATON OF AZADIRACHTIN FROM NEEM SEEDS USING FLASH CHNOMAT;TETRAHEDRON VOL43 NO.12 1987.1.1 W.KRAUS ET AL STRUCTURE DETEMINA-TION BY NMR OF AZADIRACHTIN AND RELATRD COMPOUNDS FORM AZADIRAC HTA * |
| TETRAHEDRON VOL43 NO.12 1987.1.1 W.KRAUS ET AL STRUCTURE DETEMINA-TION BY NMR OF AZADIRACHTIN AND RELATRD COMPOUNDS FORM AZADIRAC HTA * |
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| CN1149397A (en) | 1997-05-14 |
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