CN101643468B - Quinolinone alkaloid derivant as well as preparation method and application thereof - Google Patents
Quinolinone alkaloid derivant as well as preparation method and application thereof Download PDFInfo
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- CN101643468B CN101643468B CN 200910018322 CN200910018322A CN101643468B CN 101643468 B CN101643468 B CN 101643468B CN 200910018322 CN200910018322 CN 200910018322 CN 200910018322 A CN200910018322 A CN 200910018322A CN 101643468 B CN101643468 B CN 101643468B
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- DWKAQISLZUQZNU-UHFFFAOYSA-N OC(C1=C(c2ccc[nH]2)Nc2ccccc2C1=O)=O Chemical compound OC(C1=C(c2ccc[nH]2)Nc2ccccc2C1=O)=O DWKAQISLZUQZNU-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to a quinolinone alkaloid derivant as well as a preparation method and the application thereof. The preparation method comprises the following steps: firstly, carrying out strain culture for marine fungi in a strain culture medium; then carrying out fermentation culture in a fermentation culture medium; filtering obtained fermentation liquor to obtain thallus; extracting the obtained thallus by an organic solvent; carrying out chromatographic separation for an extracting solution after the extracting solution is concentrated; and concentrating obtained eluent to obtain yellow powder, i.e. the quinolinone alkaloid derivant. The compound has very high killing effect on cotton aphids, diamond back moths and heliothis virescens, can be used as pesticide of microorganisms and also has large-scale production of raw materials and wide application prospect.
Description
Technical field
The present invention relates to a kind of quinolinone alkaloid derivant 2-pyrryl that from the thalline of ocean endogenetic fungus, extract to separate-3-carboxyl-4-quinolinone and preparation method thereof and as the application of microbial pesticide sterilant.
Background technology
Since nineteen twenty-nine was prepared penicillin from fungi since, the meta-bolites of fungi had become the abundant source of medicine, and the microbiotic of most clinical applications all derives from fungus and bacterium.The meta-bolites of fungi also has other pharmaceutical use, as antitumor, and Cardiovarscular, enzyme inhibitors etc.Because the singularity of ocean environment and microorganism are at ecosystem functions, marine microorganism has developed unique metabolic way, the meta-bolites that also provides the Lu Sheng microorganism to provide, people are sent in very big hope to seek new specific medicament and microbial pesticide from marine microorganism.Yet up to the present, not yet see the microbial pesticide sterilant that is obtained to have pharmaceutical use by thalassiomycetes.
Summary of the invention
The object of the present invention is to provide a kind of 2-pyrryl that derives from thalassiomycetes-3-carboxyl-4-quinolinone and preparation method thereof and application as microbial pesticide, it can satisfy the demand of prior art.
A kind of quinolinone alkaloid derivant is characterized in that molecular formula is C
14H
10N
2O
3, structural formula is
The preparation method of above-mentioned quinolinone alkaloid derivant is characterized in that in bacterium culture medium thalassiomycetes being carried out spawn culture first, and fermentation culture in fermention medium with the gained filtering fermentation liquor, obtains thalline again, with gained thalline organic solvent extraction; The concentrated laggard circumstances in which people get things ready for a trip spectrum of extracting solution is separated, and the gained elutriant is concentrated, gets yellow powder, is quinolinone alkaloid derivant.
The application of above-mentioned quinolinone alkaloid derivant in preparation microbial pesticide sterilant.
Quinolinone alkaloid derivant of the present invention has the very strong effect of killing cotten aphid, small cabbage moth and Heliothis virescens, can be used as the microbial pesticide sterilant, and raw material can carry out scale operation, has a extensive future.
Embodiment
When preparing compound of the present invention, take following each step:
(1) in bacterium culture medium, thalassiomycetes (Penicillium sp.ZZF32#) is carried out spawn culture first, used substratum contains glucose 1.0% (weight percentage, lower with), yeast extract paste 0.1%, peptone 0.2%, agar 1.0%, sodium-chlor 0.3%, all the other are water.Be made into the test tube slant during use, above-mentioned fungal bacterial strain is 30 ℃ of lower cultivations 5 days.
Described bacterium culture medium contains glucose 0.1%-5.0%, yeast extract paste 0.01%-1%, peptone 0.01%-1%, agar 0.1%-3.0%, sodium-chlor 0.05%-5%, and all the other are water.Culture temperature is 15-35 ℃, and incubation time is 3-10 days.
(2) fungi strain of above-mentioned cultivation gained carries out fermentation culture, and used fermention medium contains glucose 1.0%, yeast extract paste 0.1%, peptone 0.2%, sodium-chlor 0.3%, and all the other are water.Fungal bacterial strain was cultivated 30 days in 28 ℃.
Described fermention medium contains glucose 0.1%-5.0%, yeast extract paste 0.01%-1%, peptone 0.01%-1%, sodium-chlor 0.05%-5%, and all the other are water.Culture temperature is 15-35 ℃, and incubation time is 7-40 days.
(3) extraction of compound 2-pyrryl-3-carboxyl-4-quinolinone separates
With previous step gained filtering fermentation liquor, obtain thalline; Thalline is with organic solvent methanol extraction 5 times, with the gained extracting solution merge concentrated after, carry out column chromatography or thin-layer chromatography and separate, with the concentrated yellow powder that to get of elutriant, be 2-pyrryl-3-carboxyl-4-quinolinone.
Described organic solvent methyl alcohol can be used propyl carbinol or chloroform or ethanol or ethyl acetate instead.
The spectral data of gained compound
2-pyrryl-3-carboxyl-4-quinolinone: a yellow amorphous powder; Mp 350-352 ℃; UV (CH
3OH) λ
Max(log ε) 214.5 (3.00), 312.5 (1.82), 353.0 (1.80) nm; IR (KBr) v
Max3292,3113,1626,1569,1524,1500,1471,1442,1396,1353,1132,867,777,754cm
-1 1H NMR (DMSO-d
6, 500MHz) δ 16.13 (1H, s, 3-COOH), 12.33 (1H, s, 1-NH), 11.80 (1H, s, 1 '-NH), 8.23 (1H, dd, J=8.0,1.5Hz, H-5), 7.86 (1H, dd, J=8.0,1.5Hz, H-8), 7.81 (1H, ddd, J=8.0,8.0,1.5Hz, H-7), 7.51 (1H, ddd, J=8.0,8.0,1.5Hz, H-6), 7.14 (1H, m, H-3 '), (6.82 1H, m, H-5 '), 6.28 (1H, m, H-4 ');
13CNMR (DMSO-d
6, 125MHz) δ 178.4 (C, C-4), 166.2 (C, 3-COOH), (147.6 C, C-2), 138.8 (C, C-9), 133.7 (CH, C-7), 125.3 (CH, C-6), 124.9 (CH, C-5), (123.6 C, C-2 '), 123.0 (CH, C-3 '), 122.8 (C, C-10), 119.1 (CH, C-8), 113.7 (CH, C-5 '), (108.8 CH, C-4 '), 106.3 (C, C-3); EIMS (pos.) m/z 254[M]
+, 236,210,179,154,127; HREIMS m/z 254.0681 (calcd for C
14H
10N
2O
3, 254.0691).
The structural formula of the 2-pyrryl that the present embodiment makes-3-carboxyl-4-quinolinone is:
The application of compound of the present invention in preparation microbial pesticide sterilant
The insecticidal activity test of compound of the present invention
Insecticidal activity experiment parallel testing three times, the disease and insect of test is respectively cotton aphid (Aphis gossypii), diamondback moth larvae (Plutella xylost) and Heliothis virescens larva (Heliothis virescens).Three kinds of specimen with water dissolution after, equal dilute with water is 1000ppm during test, and each sample is joined respectively in 96 orifice plates, each larva was all cultivated 5-9 days.2-pyrryl of the present invention-3-carboxyl-4-quinolinone is diluted with water to the concentration of 1000ppm, add 0.5ml to above-mentioned orifice plate respectively, measurement result shows, the lethality rate of cotton aphid is 100%, and diamondback moth larvae and Heliothis virescens larva are also shown strong deadly activity.
Experiment shows, 2-pyrryl of the present invention-3-carboxyl-4-quinolinone has the activity that significantly causes death to cotton aphid, diamondback moth larvae and Heliothis virescens larva, therefore can be used as the microbial pesticide sterilant, and raw material can carry out scale operation, have a extensive future.
Claims (5)
1. a quinolinone alkaloid derivant is characterized in that molecular formula is C
14H
10N
2O
3, structural formula is
2. the preparation method of quinolinone alkaloid derivant claimed in claim 1, it is characterized in that in bacterium culture medium, thalassiomycetes Penicillium sp.ZZF32# being carried out spawn culture first, fermentation culture in fermention medium again, with the gained filtering fermentation liquor, obtain thalline, with gained thalline organic solvent extraction; The concentrated laggard circumstances in which people get things ready for a trip spectrum of extracting solution is separated, and the gained elutriant is concentrated, gets yellow powder, is quinolinone alkaloid derivant.
3. preparation method as claimed in claim 2 is characterized in that described bacterium culture medium contains glucose 0.1%-5.0%, yeast extract paste 0.01%-1%, peptone 0.01%-1%, agar 0.1%-3.0%, sodium-chlor 0.05%-5%, and all the other are water.
4. preparation method as claimed in claim 2 is characterized in that described fermention medium contains glucose 0.1%-5.0%, yeast extract paste 0.01%-1%, peptone 0.01%-1%, sodium-chlor 0.05%-5%, and all the other are water.
5. the application of quinolinone alkaloid derivant claimed in claim 1 in preparation microbial pesticide sterilant.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103554090A (en) * | 2013-10-15 | 2014-02-05 | 中国海洋大学 | Terpenoid dihydroquinolone alkaloid compound as well as crystal, preparation method and application thereof as marine anti-fouling agent |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103408490B (en) * | 2013-04-19 | 2016-01-20 | 中国海洋大学 | A kind of preparation method and the application as environmentally friendly marine organisms stain control agent of quinolinone alkaloid |
| CN103554018B (en) * | 2013-10-17 | 2017-10-03 | 中国海洋大学 | A kind of dihydro-quinolinone alkaloid compound and its crystal, preparation method and the application as marine antifoulant |
| CN108623562A (en) * | 2017-03-24 | 2018-10-09 | 中国海洋大学 | A kind of quinolinone alkaloid class compound and its preparation method and application |
| CN108623560A (en) * | 2017-03-24 | 2018-10-09 | 中国海洋大学 | A kind of Quinolone acid analog derivative and its preparation method and application |
| CN108623561A (en) * | 2017-03-24 | 2018-10-09 | 中国海洋大学 | A method of preparing piperazine Nino acid compound |
| CN108617661A (en) * | 2017-03-24 | 2018-10-09 | 中国海洋大学 | A kind of application of alkaloid compound in agricultural drugs |
| WO2023156323A1 (en) | 2022-02-17 | 2023-08-24 | Syngenta Crop Protection Ag | Herbicidal quinolone derivatives |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101012221A (en) * | 2007-01-15 | 2007-08-08 | 朱峰 | Antineoplastic alkaloid |
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| CN101012221A (en) * | 2007-01-15 | 2007-08-08 | 朱峰 | Antineoplastic alkaloid |
Non-Patent Citations (2)
| Title |
|---|
| JP特公平6-70032B2 1994.09.07 |
| M.ABE et al..Quinolactacide,a New Quinolone Insecticide from Penicillium citrinum Thom F 1539.《Biosci.Biotechnol.Biochem.》.2005,第69卷(第6期),第1202-1205页. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103554090A (en) * | 2013-10-15 | 2014-02-05 | 中国海洋大学 | Terpenoid dihydroquinolone alkaloid compound as well as crystal, preparation method and application thereof as marine anti-fouling agent |
| CN103554090B (en) * | 2013-10-15 | 2017-03-15 | 中国海洋大学 | A kind of terpenoid dihydro-quinolinone alkaloid compound and its crystal, preparation method and the application as marine antifoulant |
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