CN101849542A - Application of Xylocarpus granatum limonin A serving as Brontispa longissima poisoning agent - Google Patents
Application of Xylocarpus granatum limonin A serving as Brontispa longissima poisoning agent Download PDFInfo
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- CN101849542A CN101849542A CN 201010194053 CN201010194053A CN101849542A CN 101849542 A CN101849542 A CN 101849542A CN 201010194053 CN201010194053 CN 201010194053 CN 201010194053 A CN201010194053 A CN 201010194053A CN 101849542 A CN101849542 A CN 101849542A
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Abstract
The invention discloses an application of Xylocarpus granatum limonin A serving as a Brontispa longissima poisoning agent, the structure thereof is shown as the general formula (I). In the invention, a leaf dipping method is utilized to measure the toxic activity of the Xylocarpus granatum limonin A on the fifth instar larva of Brontispa longissima, and the result shows that the Xylocarpus granatum limonin A has strong toxic effect on the fifth instar larva of the Brontispa longissima. When the concentration for test is 50mg/L, the lethality rate of the fifth instar larva of the Brontispa longissima is 100%, the pest killing effect of the Xylocarpus granatum limonin A with the concentration is a little more preferable to contrast insecticide rotenone and far more preferable to contrast insecticide toosendanin at the same experimental conditions. Thus the Xylocarpus granatum limonin A can be used as the Brontispa longissima poisoning agent and has good toxic effect on the fifth instar larva of the Brontispa longissima. The general formula (I) is shown in the specification.
Description
Technical field:
The present invention relates to the new application of the limonin compound-Xylocarpus granatum limonin A serving of following general formula (I) expression, be specifically related to the application of Xylocarpus granatum limonin A serving, especially as the poisoning agent of Brontispa longissima 5 instar larvaes as Brontispa longissima poisoning agent.
Background technology:
Limonin compound-the Xylocarpus granatum limonin A serving (Xylolimonoid A) of following general formula (I) expression is separated from Cipadessa baecifera Miq in reported first in 2007 and (is seen document: L.S.Gan, X.N.Wang, Y.Wu et al.J.Nat.Prod., 70 (8): 1344-1347 (2007)).
Its general formula is as follows:
General formula (I)
Compound-the Xylocarpus granatum limonin A serving of general formula (I) expression, this compound outward appearance powder that is white in color, molecular formula is C
32H
42O
8, its chemistry 6-deoxidation by name, 3-O-2S-methylbutyryl base-sweitenolide [English name 6-Deoxy, 3-O-2S-methylbutyryl-swietenolide], Chinese Xylocarpus granatum limonin A serving by name.
Up to the present, do not find the report that the compound-Xylocarpus granatum limonin A serving of above-mentioned general formula (I) expression has toxic action to Brontispa longissima Brontispa longissima (Gestro).
Brontispa longissima Brontispa longissima (Gestro) is a kind of external crushing insect of substantial risk.Ating the third place in 19 kinds of forestry quarantine harmful organisms lists of the up-to-date announcement of the State Administration of Forestry, is China's newly-increased two class quarantine harmful organisms of forbidding entering a country in 1992.At present Brontispa longissima in China Hainan Province, Guangdong Province, Taiwan Province and the harm of area, Hong Kong is serious, and have the tendency to spread.This insect babassus such as coconut, betel nut, big yagua of seriously causing harm have constituted serious threat to growth and the breeding of the Palmae ornamental plant of China subtropics even the plantation of area, temperate zone.Domestic chemical prevention and control method mainly is the chemical pesticide that adopts beta-cypermethrin, gives a tongue-lashing synthetic such as worm quinoline, phoxim at present.Though this class agricultural chemicals virulence is strong, instant effect, long-term, a large amount of uses easily cause problems such as residue of pesticide, pesticide resistance, environmental pollution and chronic toxicity.Therefore, research and development high-efficiency low-toxicity, biopesticide nuisanceless, that selectivity is strong have become the new trend and the inevitable demand of current agricultural chemicals development.
The compound of above-mentioned general formula (I) expression is to be produced by plant metabolism, belongs to biopesticide, the variety of problems that exploitation can well overcome above-mentioned synthetic as the poisoning agent of Brontispa longissima chemical pesticide exists as the poisoning agent of Brontispa longissima.
Summary of the invention:
The purpose of this invention is to provide the new application of Xylocarpus granatum limonin A serving as Brontispa longissima poisoning agent.
The present invention has very strong toxic action by larva life experiment confirm Xylocarpus granatum limonin A serving to 5 instar larvaes of Brontispa longissima, therefore can be used as the poisoning agent of Brontispa longissima, thereby has realized purpose of the present invention.
Xylocarpus granatum limonin A serving in of the present invention can obtain by method separation of the prior art, as according to list of references L.S.Gan, X.N.Wang, Y.Wu et al.J.Nat.Prod., 70 (8): the disclosed separating method of 1344-1347 (2007) separates acquisition.
The inventor utilizes modern chromatographic technique to isolate limonin compound Xylocarpus granatum limonin A serving (Xylolimonoid A) from the Xylocarpus Koenig mangrove Xylocarpus moluccensis of India, its separating method is that the seed with Xylocarpus Koenig mangrove Xylocarpus moluccensis is a raw material, pulverize the back alcohol extract, get ethanol extract behind the concentrating under reduced pressure, after ethanol extract adds the water suspendible, use ethyl acetate extraction, the acetic acid ethyl ester extract that concentrating under reduced pressure obtains.This extract is through the purification on normal-phase silica gel column chromatography, it with the chloroform-methanol eluant, eluent from volume ratio 100: 1-5: 1 gradient elution, collecting the chloroform-methanol volume ratio is the cut of 100: 1 wash-outs, then through reverse silica gel column chromatography wash-out, it with the acetonitrile-water eluant, eluent from volume ratio 50: 50-100: 0 gradient elution, collecting the acetonitrile-water volume ratio is the cut of 65: 35 wash-outs, prepare by high performance liquid chromatography at last, with volume ratio is that 53: 47 acetonitrile-water is the eluant, eluent wash-out, separation and purification and obtain compound Xylocarpus granatum limonin A serving (XylolimonoidA.
The present invention adopts leaf dipping method to measure the cytotoxicity of Xylocarpus granatum limonin A serving to Brontispa longissima 5 instar larvaes, and the result shows that this compound has very strong toxic action to Brontispa longissima 5 instar larvaes.When being 50mg/L for examination concentration, the lethality rate of Brontispa longissima 5 instar larvaes is 100%, and under this concentration, under the equal experiment condition, its insecticidal effect is better than contrasting medicament-rotenone slightly, is far superior to contrast medicament-toosendanin, and poisoning the results are shown in Table 1.
Table 1 compound Xylocarpus granatum limonin A serving (Xylolimonoid A) is to the virulence of Brontispa longissima 5 instar larvaes
Above-mentioned experimental result shows that Xylocarpus granatum limonin A serving can be as the poisoning agent of Brontispa longissima, and it has good toxic effect to Brontispa longissima 5 instar larvaes.
Embodiment:
Following examples are to further specify of the present invention, rather than limitation of the present invention.
The preparation of Xylocarpus granatum limonin A serving (Xylolimonoid A):
Seed with 7.0kg India Xylocarpus Koenig plant Xylocarpus moluccensis is a raw material, pulverizes the back and extracts 5 times with the ethanol room temperature of 15kg 95% (volume fraction), gets ethanol extract 1087g behind the concentrating under reduced pressure.After ethanol extract adds the water suspendible, use ethyl acetate extraction 8 times, the acetic acid ethyl ester extract 320g that concentrating under reduced pressure obtains.This extract is through purification on normal-phase silica gel (100-200 order) column chromatography, with the chloroform-methanol elution system from volume ratio 100: 1-5: 1 gradient elution, collecting the chloroform-methanol volume ratio is the cut of 100: 1 wash-outs, after this cut concentrates, then through reverse silica gel (
75 μ m) column chromatography wash-out, with the acetonitrile-water elution system from volume ratio 50: 50-100: 0 gradient elution, collecting the acetonitrile-water volume ratio is the cut of 65: 35 wash-outs, (Waters 600 by the high performance liquid chromatography preparation at last for this cut, chromatographic column YMC 250 * 10mm, i.d., 5 μ m, RP-C18, flow velocity 3ml/min, retention time RT=18.5min), be that 53: 47 acetonitrile-water is the eluant, eluent wash-out with volume ratio, separation and purification and obtain the whitening compound, this compound is accredited as Xylocarpus granatum limonin A serving (XylolimonoidA) through structure.
Structure is identified:
By high resolution mass spectrum (HRTOF-MS) [M+Na] of this compound as can be known
+Be 577.2795, determine that its molecular formula is C
32H
42O
8This compound uv-absorption maximum wavelength is positioned at 210.0nm.Its nuclear magnetic resonance spectrum (
1H NMR,
13C NMR) data and document [L.S.Gan; X.N.Wang; Y.Wu et al.J.Nat.Prod.; 70 (8): 1344-1347 (2007)] contrast of the data of report is consistent; so compound is defined as the 6-deoxidation, 3-O-2S-methylbutyryl base-sweitenolide, English name 6-Deoxy; 3-O-2S-methylbutyryl-swietenolide, Chinese Xylocarpus granatum limonin A serving by name.Its
1H NMR with
13C NMR data see Table 2.
Table 2.
1H,
13C NMR data of Xylolimonoid A. (500MHz for
1H and 125MHz for
13C NMR, Chloroform-d)
Comparative Examples 1:
For trying Brontispa longissima larva model:
System adopts back from Danzhou, Hainan coconut palm for the examination larva, breeds many generations at indoor feeding.5 instar larvaes of the individual size of picking, solid colour are for examination during test.
The cytotoxicity test:
Leaf dipping method is adopted in test, rotenone-acetone soln dipping of the leaf of coconut palm Cocos nucifera Linnaeus being put into 50mg/L took out after 3 seconds, put on the blotting paper and dry, the medicine blade that soaks that will dry is again put into culture dish, then Brontispa longissima 5 instar larvaes of the same size are put into the culture dish that soaks the medicine blade is housed, be covered with filter paper at the bottom of the culture dish and preserve moisture.The culture dish of handling well is placed in the incubator (T:25 ± 1 ℃, RH=70～80%).Make blank with acetone, test repeats 3 times, each 10 larvas.Regular check examination worm death condition is touched polypide with writing brush, is considered as death with complete motionless person.Respectively at adding up dead borer population when 12 hours, 24 hours, 48 hours and 72 hours after the administration, calculate lethality.Its result sees table 1.
Comparative Examples 2:
For trying Brontispa longissima larva model:
System adopts back from Danzhou, Hainan coconut palm for the examination larva, breeds many generations at indoor feeding.5 instar larvaes of the individual size of picking, solid colour are for examination during test.
The cytotoxicity test:
Leaf dipping method is adopted in test, toosendanin-acetone soln dipping of the leaf of coconut palm Cocos nucifera Linnaeus being put into 50mg/L took out after 3 seconds, put on the blotting paper and dry, the medicine blade that soaks that will dry is again put into culture dish, then Brontispa longissima 5 instar larvaes of the same size are put into the culture dish that soaks the medicine blade is housed, be covered with filter paper at the bottom of the culture dish and preserve moisture.The culture dish of handling well is placed in the incubator (T:25 ± 1 ℃, RH=70～80%).Make blank with acetone, test repeats 3 times, each 10 larvas.Regular check examination worm death condition is touched polypide with writing brush, is considered as death with complete motionless person.Respectively at adding up dead borer population when 12 hours, 24 hours, 48 hours and 72 hours after the administration, calculate lethality.Its result sees table 1.
Embodiment 1:
For trying Brontispa longissima larva model:
System adopts back from Danzhou, Hainan coconut palm for the examination larva, breeds many generations at indoor feeding.5 instar larvaes of the individual size of picking, solid colour are for examination during test.
The cytotoxicity test
Leaf dipping method is adopted in test, Xylocarpus granatum limonin A serving-acetone soln dipping of the leaf of coconut palm Cocos nucifera Linnaeus being put into 50mg/L took out after 3 seconds, put on the blotting paper and dry, the medicine blade that soaks that will dry is again put into culture dish, then Brontispa longissima 5 instar larvaes of the same size are put into the culture dish that soaks the medicine blade is housed, be covered with filter paper at the bottom of the culture dish and preserve moisture.The culture dish of handling well is placed in the incubator (T:25 ± 1 ℃, RH=70～80%).Make blank with acetone, test repeats 3 times, each 10 larvas.Regular check examination worm death condition is touched polypide with writing brush, is considered as death with complete motionless person.Respectively at adding up dead borer population when 12 hours, 24 hours, 48 hours and 72 hours after the administration, calculate lethality.Its result sees table 1.
Claims (2)
1. the compound of following general formula (I) expression is as the application of Brontispa longissima poisoning agent:
General formula (I).
2. the compound of general formula according to claim 1 (I) expression is characterized in that as the application of Brontispa longissima poisoning agent described Brontispa longissima is 5 instar larvaes of Brontispa longissima.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447650A (en) * | 2014-12-22 | 2015-03-25 | 胡文杰 | Novel limonin compound and preparation method and medical application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008021368A2 (en) * | 2006-08-11 | 2008-02-21 | The Johns Hopkins University | Compositions and methods for neuroprotection |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008021368A2 (en) * | 2006-08-11 | 2008-02-21 | The Johns Hopkins University | Compositions and methods for neuroprotection |
Non-Patent Citations (2)
| Title |
|---|
| 《Chem. Pharm. Bull.》 20100201 Jing Zhang et al. Mexicanolides from the Seeds of a Krishna Mangrove, Xylocarpus moluccensis 552-555 1-2 第58卷, 第4期 * |
| 《J.Nat.Prod.》 20070407 Li-She Gan et al. Tetranortriterpenoids from Cipadessa baccifera 1344-1347 1-2 第70卷, 第8期 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104447650A (en) * | 2014-12-22 | 2015-03-25 | 胡文杰 | Novel limonin compound and preparation method and medical application thereof |
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Application publication date: 20101006 |