CN104593281A - A plurality of indolocarbazole alkaloids having strong insect disinfestation activities, and production strain thereof - Google Patents

A plurality of indolocarbazole alkaloids having strong insect disinfestation activities, and production strain thereof Download PDF

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CN104593281A
CN104593281A CN201310547718.8A CN201310547718A CN104593281A CN 104593281 A CN104593281 A CN 104593281A CN 201310547718 A CN201310547718 A CN 201310547718A CN 104593281 A CN104593281 A CN 104593281A
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indole carbazole
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王林
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Abstract

The present invention discloses a plurality of indolocarbazole alkaloids having strong insect disinfestation activities, and a production strain of the indolocarbazole alkaloids. The indolocarbazole alkaloid compound production strain CQT14-24 is a marine Streptomyces nitrosporeus CQT14-24 strain, wherein the strain is subjected to artificial culture, and the obtained fermentation product is extracted by the conventional chemical method so as to obtain four indolocarbazole alkaloids and an anthraquinone compound. According to the present invention, the indolocarbazole alkaloids and the one anthraquinone compound provide strong killing effects on a variety of cultivated plant pests, particularly the pests having characteristics of spreading in agriculture and forestry production and serious harm and comprising Pieris rapae, Brevicoryne brassicae, Hyphantria cunea, Plutella xyllostella, Mythimna separate and Helicoverpa armigera, wherein the relative mortality rate achieves 81.9-100%, the polypide is seriously reduced, the growth inhibition rate is 100%, and the imago pupation rate is reduced by 70.4-86.7%; and the strain is subjected to acclimation through the artificial culture, and has characteristics of stable feature, easy culture, simple and feasible operation method, no environmental pollution, short period, cheap raw materials, low production cost, good development prospect, and easy industrialization achieving.

Description

Several indole carbazole alkaloid and producing bacterial strain with strong insecticidal activity
Technical field
The invention belongs to marine microorganism field, several strong insecticidal activity indole carbazole alkaloid and producing bacterial strain specifically, this culture presevation is in China Committee for Culture Collection of Microorganisms's common micro-organisms center (CGMCC), address is No. 3, BeiChen West Road, Chaoyang District, BeiJing City, Institute of Microorganism, Academia Sinica, preservation date on February 25th, 2011, deposit number CGMCC No.4607, Classification And Nomenclature Streptomyces nitrosporus.
background technology
China is large agricultural country, the export of farm produce occupies important ratio in national economy, in recent years, in the world to Pesticide Residue pay attention to day by day, the agricultural chemicals that forbidding limits the use of is more and more, residue criterion improves constantly, and the direct and consequential damage causing China's Agricultural to export because of chemical pesticide residue problem every year all reaches more than tens.Simultaneously, the appearance of the existing pest resistance to insecticide increase of cultivated plant and New harmful insect, and the requirement of country to the agricultural chemicals with autonomous property right improves day by day, also require the sterilant of the constantly high-efficiency low-toxicity that development is new, the new lead compound developing high-efficiency low-toxicity from natural product is the key of initiative novel pesticide.New pesticide poullant is from biology, compared with other biological source pesticide, the advantage that microbial pesticide is low with its development cost, more easily realize industrialization, become the first-selected resource of exploitation novel pesticide both at home and abroad, the searching new texture active substance of microbial source or the New function of existing compound are the important channels of biological pesticide initiative.
Because the impact of insect on cultivated plant is more remarkable than disease, the demand of market to sterilant is stronger, but in existing agricultural chemicals research and development, obtain the probability of strong desinsection lead compound, be far smaller than the lead compound of bacteriostatic activity, namely the compound of strong insecticidal activity is more difficult obtains at nature, be badly in need of exploitation new resources, land microbe research comparatively early, find that the probability of new agricultural microorganism resource obviously reduces, the metabolic type that special habitat, ocean determines microorganism is different from land microorganism, find that the probability of novel pesticide compound will increase greatly, marine microorganism becomes discovery novel pesticide compound new resources and receives much concern.
Summary of the invention
The object of this invention is to provide several indole carbazole alkaloid preparation method with strong insecticidal activity, habitat, the ocean streptomycete CQT14-24 bacterial strain Streptomyces nitrosporus and application thereof that produce this compounds are provided simultaneously, this bacterial strain is preserved in China Committee for Culture Collection of Microorganisms's common micro-organisms center (CGMCC) on February 25th, 2011, preserving number is CGMCC No.4607), the classes of compounds that these actinomycetes produce is enriched, regulated by the formula of artificial culture method, dissimilar active medicinal matter can be obtained, 4 indole carbazole alkaloids provided by the invention and 1 anthraquinone analog compound are to the growth of insect, survive and pupate that all there is very strong restraining effect, there are well exploitation new pesticides potentiality.
The object of the invention is to be realized by following technical scheme, several strong insecticidal activity indole carbazole alkaloid and anthraquinone compounds are prepared, described indole carbazole alkaloid compound producing bacterial strain CQT14-24, for habitat, ocean streptomyces nitrosporeus Streptomyces nitrosporeus, CQT14-24 bacterial strain is through artificial culture, obtain fermented product to extract through conventional chemical processes again, 4 indole carbazole alkaloids and 1 anthraquinone analog compound can be obtained, 5 compounds all have strong lethal effect to various plants insect, and its feature comprises the steps:
1) with its deposit number be: the bacterial strain CQT14-24 of CGMCC No.4607, be placed in following solid medium and cultivate 5 days, then fermentation culture in the fermented liquid proceeding to same recipe, culture medium prescription is: Zulkovsky starch 15-20g, soya bean leaching juice 150-200ml, ooze leaching juice 100-150ml, KNO 31.1-1.5g, K 2hPO 40.4-0.8g, MgSO 40.5-0.8g, NaCl, 12-20g, KCl0.04-0.09g, MgCl 20.23-0.50g, FeSO47H 2o0.01-0.03g, vitamin complex 1mL/L, water 650-750ml, pH7-7.5, not adding agar is nutrient solution, and adding agar 16-19g is solid medium, 25 DEG C-26 DEG C rotating speed 150rpm, and shaking culture obtains fermented product in 11 days, and fermented product is divided into thalline and bacterium liquid;
2) be extracted with ethyl acetate 3 times after bacterium liquid concentrating under reduced pressure, after revolving steaming, obtain medicinal extract; Thalline ethyl acetate supersound extraction, merge with bacterium immersion cream after medicinal extract tlc analysis, reduced pressure chromatography, sherwood oil: acetone (20:1), methylene dichloride: methyl alcohol (1:1), methyl alcohol is wash-out respectively, by methylene dichloride: ODS column separating purification on methyl alcohol, use methyl alcohol respectively: water (2:3) and 100% methanol-eluted fractions, obtain 4 indole carbazole alkaloids and 1 anthraquinone compounds with gel filtration chromatography, HPLC chromatogram conventional isolation techniques.
The structure of 5 described compounds is Des (hydroxyimino)-TAN1030A (1), holyrine A (2), RK-1409 (3), Streptocarbazoles B (4), K1115A (5), wherein compound 1-4 is indole carbazole alkaloid, and 5 is anthraquinone analog compound.
4 described indole carbazole alkaloids and 1 anthraquinone analog compound ordinary method test activity, the cabbage caterpillar (Pieris rapae) common to agricultural and harm is serious, brevicoryne brassicae (Brevicoryne brassicae), fall webworms (Hyphantria cunea), small cabbage moth (Plutella xyllostella), mythimna separata (Mythimna separata), the growth of bollworm (Helicoverpa armigera), survive and pupate that all there is very strong insecticidal activity, its corrected mortality can reach 81.9%-100%, polypide severe decrease, the inhibiting rate of growth is 100%, percentage of pupation reduces 70.4%-86.7%, .
The effect of strong insecticidal activity indole carbazole alkaloid compound of the present invention and producing bacterial strain is:
1, 4 indole carbazole alkaloids and 1 anthraquinone analog compound all have strong lethal effect to multiple cultivated plant insect, specifically producing agroforestry occurs generally, endanger serious cabbage caterpillar (Pieris rapae) brevicoryne brassicae (Brevicoryne brassicae) fall webworms (Hyphantria cunea) small cabbage moth (Plutella xyllostella) mythimna separata (Mythimna separata) and bollworm (Helicoverpa armigera) relative lethality reaches 81.9%-100%, polypide severe decrease, the inhibiting rate of growth is 100%, adult percentage of pupation reduces 70.4%-86.7%.Although these 5 compounds are known compounds, never someone reports that these compounds have insecticidal activity, the invention provides the new activity of these compounds.
2, this bacterial strain is tamed by artificial culture, and stability of characteristics is easily cultivated, and working method is simple and feasible, does not pollute environment, and the cycle is short, raw materials used cheapness, and production cost is low, and DEVELOPMENT PROSPECT is good, easily realizes industrialization.
Specific embodiment
Protection scope of the present invention is not only confined in following examples, and concrete technological step of the present invention is as follows:
Embodiment 1: the preparation of strong insecticidal activity indole carbazole alkaloid and anthraquinone compounds:
Described indole carbazole alkaloid compound producing bacterial strain CQT14-24 is habitat, ocean streptomyces nitrosporeus Streptomyces nitrosporeus, bacterial strain is through artificial culture, obtain fermented product to extract through conventional chemical processes again, can obtain 4 indole carbazole alkaloids and 1 anthraquinone analog compound, its feature comprises the steps:
1) with its deposit number be: the bacterial strain CQT14-24 of CGMCC No.4607, be placed in following solid medium and cultivate 5 days, then fermentation culture in the fermented liquid proceeding to same recipe, culture medium prescription is: Zulkovsky starch 15-20g, soya bean leaching juice 150-200ml, ooze leaching juice 100-150ml, KNO 31.1-1.5g, K 2hPO 40.4-0.8g, MgSO 40.5-0.8g, NaCl, 12-20g, KCl0.04-0.09g, MgCl 20.23-0.50g, FeSO47H 2o0.01-0.03g, vitamin complex 1mL/L, water 650-750ml, pH7-7.5, not adding agar is nutrient solution, and adding agar 16-19g is solid medium, 25 DEG C-26 DEG C rotating speed 150rpm, and shaking culture obtains fermented product in 11 days, and fermented product is divided into thalline and bacterium liquid;
2) be extracted with ethyl acetate 3 times after bacterium liquid concentrating under reduced pressure, after revolving steaming, obtain medicinal extract; Thalline ethyl acetate supersound extraction, merge with bacterium immersion cream after medicinal extract tlc analysis, reduced pressure chromatography, sherwood oil: acetone (20:1), methylene dichloride: methyl alcohol (1:1), methyl alcohol is wash-out respectively, by methylene dichloride: ODS column separating purification on methyl alcohol, use methyl alcohol respectively: water (2:3) and 100% methanol-eluted fractions, obtain 5 compounds with gel filtration chromatography, HPLC chromatogram conventional isolation techniques;
Utilize mass spectrum, nuclear-magnetism, infrared spectrum technique means to carry out parsing to 5 compounds and determine its structure:
Compound S NT-01
Pale yellow powder, mp241 ~ 243 DEG C, 35.2 (c0.34, MeOH), Dragendorff's reagent is positive, and has bluish voilet fluorescence under ultraviolet lamp, ESIMS m/z452.1 [M+1] +, in conjunction with 1h-NMR and 13c-NMR data, deterministic adduct molecule formula is: C 27h 21n 3o 4, 1h-NMR (400MHz, DMSO-d 6) δ: 7.72 (1H, d, J=8.0Hz, H-1), 7.53 (1H, t, J=8.0Hz, H-2), 7.35 (1H, t, J=7.6Hz, H-3), 9.31 (1H, d, J=7.8Hz, H-4), 8.62 (1H, s, H-6), 4.97 (2H, s, H-7), 8.00 (1H, d, J=8.2Hz, H-8), 7.35 (t, J=8.1Hz, H-9), 7.47 (1H, t, J=8.1Hz, H-10), 8.02 (1H, t, J=8.2Hz, H-11), 7.43 (1H, d, J=6.6Hz, H-6 '), 4.01 (1H, dd, J=6.6, 14.1Hz5 '-Ha), 2.67 (1H, d, J=14.1Hz, 5 '-Hb), 5.08 (1H, s, H-3 '), 2.56 (3H, s, 2 '-CH 3), 3.41 (3H, s, 3 '-OCH 3), 13c-NMR (100MHz, DMSO-d 6) δ c109.6 (d, C-1), 126.1 (d, C-2), 120.5 (d, C-3), 126.2 (d, C-4), 123.5 (s, C-4a), 115.8 (s, C-4b), 120.1 (s, C-4c), 172.1 (s, C-5), 45.9 (t, C-7), 133.1 (s, C-7a), 115.1 (s, C-7b), 124.4 (s, C-7c), 121.5 (d, C-8), 121.1 (d, C-9), 125.6 (d, C-10), 116.2 (d, C-11), 140.5 (s, C-11a), 127.4 (s, C-12a), 125.5 (s, C-12b), 136.5 (s, C-13a), 85.1 (d, C-6 '), 46.1 (t, C-5 '), 200.8 (s, C-4 '), 85.6 (d, C-3 '), 99.9 (s, C-2 '), 30.1 (q, C-2 '-CH 3), 59.5 (q, C-3 '-OCH 3) according to above-mentioned data inspection document, determine that structure is Des (hydroxyimino)-TAN1030A,
Compound S NT-02
Pale yellow powder, mp247 ~ 247 DEG C, 40.2 (c0.20, MeOH), have bluish voilet fluorescence under UV-light, Dragendorff's reagent is positive, ESIMS m/z441.1 [M+1] +, in conjunction with 1h-NMR and 13c-NMR data, deterministic adduct molecule formula is: C 26h 24n 4o 3, 1hNMR (400MHz, DMSO-d 6) δ: 7.93 (1H, d, J=8.0Hz, H-1), 7.30 (1H, t, J=7.6Hz, H-2), 7.49 (1H, t, J=7.9Hz, H-3), 9.48 (1H, d, J=7.8Hz, H-4), 8.48 (1H, s, H-6), 4.97 (2H, d, J=5.6Hz, H-7), 8.07 (1H, d, J=8.4Hz, H-8), 7.51 (t, J=8.1Hz, H-9), 7.32 (1H, t, J=8.1Hz, H-10), 7.71 (1H, t, J=8.2Hz, H-11), 6.63 (1H, d, J=10.5Hz, H-6 '), 2.29 (1H, dd, J=10.2, 11.5Hz, H-5 '), 1.88 (1H, dd, J=11.1Hz, H-5 '), 3.60 (1H, brd, J=10.5Hz, H-4 '), 3.82 (1H, brs, H-3 '), 4.55 (1H, q, J=7.5Hz, H-2 '), 1.55 (3H, s, 2 '-CH 3) 13c-NMR (100MHz, DMSO-d 6) δ: 109.9 (d, C-1), 120.0 (d, C-2), 125.5 (d, C-3), 126.2 (d, C-4), 124.8 (s, C-4a), 117.7 (s, C-4b), 119.0 (s, C-4c), 172.7 (s, C-5), 45.7 (t, C-7), 134.5 (s, C-7a), 115.3 (s, C-7b), 122.3 (s, C-7c), 121.6 (d, C-8), 125.7 (d, C-9), 120.2 (d, C-10), 112.0 (d, C-11), 139.2 (s, C-11a), 127.9 (s, C-12a), 122.7 (s, C-12b), 139.0 (s, C-13a), 76.5 (d, C-6 '), 36.3 (t, C-5 '), 46.1 (d, C-4 '), 71.0 (d, C-3 '), 76.8 (d, C-2 '), 14.7 (q, C-2 '-CH 3), according to above-mentioned data inspection document, deterministic laminate structures is holyrine A,
Compound S NT-03
Safran powder, mp236 ~ 238 DEG C, + 37.5 (c0.31, MeOH), have bluish voilet fluorescence under UV-light, Dragendorff's reagent reaction is positive.ESI-MS m/z481.1 [M-H] +in conjunction with 1h-NMR and 13c-NMR data, deterministic adduct molecule formula is: C 28h 24n 4o 4, 1h-NMR (600MHz, DMSO-d 6): δ h7.65 (1H, d, J=7.7Hz, H-1), 7.65 (1H, t, J=7.6Hz, H-2), 7.44 (1H, t, J=7.6Hz, H-3), 9.29 (1H, d, J=7.7Hz, H-4), 11.13 (1H, s, H-6), 9.10 (1H, dd, J=3.4, 7.7Hz, H-8), 7.46 (t, J=7.9Hz, H-9), 7.65 (1H, t, J=7.8Hz, H-10), 8.09 (1H, t, J=8.2Hz, H-11), 6.96 (1H, d, J=8.7Hz, H-6 '), 3.30 (1H, m, 5 '-Ha), 2.16 (1H, m, 5 '-Hb), 4.46 (1H, s, H-3 '), 2.51 (3H, s, 2 '-CH 3), 3.36 (3H, s, 3 '-OCH 3), 2.32 (3H, s, 4-NCH 3), 13c-NMR (125MHz, DMSO-d 6) δ c110.3 (d, C-1), 127.6 (d, C-2), 121.5 (d, C-3), 125.6 (d, C-4), 123.4 (s, C-4a), 115.4 (s, C-4b), 121.4 (s, C-4c), 171.4 (s, C-5), 171.2 (s, C-7), 119.8 (s, C-7a), 116.7 (s, C-7b), 121.9 (s, C-7c), 125.4 (d, C-8), 121.5 (d, C-9), 127.6 (d, C-10), 113.2 (d, C-11), 139.4 (s, C-11a), 131.4 (s, C-12a), 130.3 (s, C-12b), 138.1 (s, C-13a), 81.4 (d, C-6 '), 27.6 (t, C-5 '), 53.6 (d, C-4 '), 80.0 (d, C-3 '), 93.2 (s, C-2 '), 28.3 (q, C-2 '-CH 3), 60.3 (q, C-3 '-OCH 3), 41.0 (C-4 '-NCH 3) above-mentioned comparing document, identify that this compound is RK-1409,
Compound S NT-04
Pale yellow powder, has blue-fluorescence under UV-light, and Dragendorff's reagent is aobvious positive, ESIMS m/z466.1 [M+H]+, -23.5 (c0.40, MeOH), in conjunction with 1H-NMR and 13C-NMR data, deterministic adduct molecule formula is: C28H23N3O4, 1H-NMR (400MHz, DMSO-d6) δ: 7.83 (1H, d, J=8.5Hz, H-1), 7.57 (1H, t, J=7.6Hz, H-2), 7.36 (1H, t, J=7.6Hz, H-3), 9.40 (1H, d, J=8.0Hz, H-4), 8.66 (1H, s, H-6), 5.00 (2H, d, J=2.8Hz, H-7), 8.05 (1H, d, J=7.8Hz, H-8), 7.36 (t, J=7.0Hz, H-9), 7.53 (1H, t, J=7.8Hz, H-10), 8.26 (1H, t, J=8.6Hz, H-11), 1.61 (1H, s, H-6 '), 3.44 (1H, dd, J=6.0.15.6Hz, H-2 '), 3.57 (1H, d, J=14.5Hz, H-2 '), 7.00 (1H, d, J=5.6Hz, H-1 '), 3.59 (3H, s, 3 '-OCH3), 3.16 (3H, s, 4 '-OCH3), 13C-NMR (100MHz, DMSO-d6) δ H110.2 (d, C-1), 126.4 (d, C-2), 121.0 (d, C-3), 126.1 (d, C-4), 123.2 (s, C-4a), 116.2 (s, C-4b), 120.0 (s, C-4c), 172.2 (s, C-5), 45.7 (t, C-7), 133.9 (s, C-7a), 116.7 (s, C-7b), 123.4 (s, C-7c), 121.5 (d, C-8), 121.0 (d, C-9), 126.4 (d, C-10), 115.3 (d, C-11), 141.0 (s, C-11a), 133.2 (s, C-12a), 125.4 (s, C-12b), 139.5 (s, C-13a), 14.7 (q, C-6 '), 142.8 (s, C-5 '), 133.9 (s, C-4 '), 87.8 (s, C-3 '), 37.8 (t, C-2 '), 77.5 (d, C-1 '), 51.5 (q, C-3 ' OCH3), 62.1 (q, C-4 ' OCH3) above-mentioned comparing document, determine that structure is Streptocarbazoles B,
Compound S NT-05
Yellow powder, ESI-MS -m/z325.0, is its quasi-molecular ion peak [M-H] -, be C in conjunction with NMR data determination molecular formula 18h 14o 6, H-NMR and 13c-NMR data show that this compound is anthraquinone component: 1h-NMR (500MHz, DMSO-d 6) δ h7.60 (1H, s, H-4), 7.65 (1H, d, J=7.2Hz, H-5), 7.75 (1H, d, J=7.8Hz, H-6), 7.36 (1H, d, J=8.2Hz, H-7), 4.77 (2H, s, H-11), 3.17 (2H, t, J=7.8Hz, H-11), 1.63 (2H, tq, J=7.4,7.8Hz, H-12), 1.02 (3H, t, J=7.4Hz, H-13) 13c-NMR (125MHz, DMSO-d 6) δ h146.6 (s, C-1), 130.9 (s, C-2), 158.7 (s, C-3), 113.2 (d, C-4), 137.2 (s, C-4a), 118.7 (d, C-5), 136.5 (d, C-6), 124.9 (d, C-7), 162.0 (s, C-8), 117.5 (s, C-8a), 189.6 (s, C-9), 121.9 (s, C-9a), 182.6 (d, C-10), 132.9 (s, C-10a), 34.5 (t, C-11), 24.1 (t, C-12), 15.1 (q, C-13), 168.6 (s, C-14), its spectral data and document comparison, determine that its structure is K1115A.
Embodiment 2: compound produces the insecticidal activity test of common insect pests to several agroforestry
Cabbage caterpillar (Pieris rapae), brevicoryne brassicae (Brevicoryne brassicae), fall webworms (Hyphantria cunea), small cabbage moth (Plutella xyllostella), mythimna separata (Mythimna separata) bollworm (Helicoverpa armigera) ordinary method is fed 2-3 age, first by above-mentioned 5 compounds with 1% DMSO solution dilution to 20 μ g/ml, wild cabbage, maize leaf breaks into leaf butterfly, put within 5 seconds, to take out afterwards for the leaching of reagent liquid and dry, put into the examination worm of hungry 5h respectively, be placed in constant temperature in insectary to raise, often process repetition 3 times, if be only treated to contrast with DMSO, observe examination worm to grow situation, every 24h weighs once, record examination polypide is heavy, calculate and examination worm is grown inhibiting rate, statistical correction mortality ratio after 96h, the percentage of pupation of survival examination worm is observed using cabbage caterpillar as target pest.
Table 15 compound produces the insecticidal activity of common insect pests to 6 kinds of agroforestry
As seen from the above table, 5 indole carbazole alkaloids insect heavier to 6 kinds of agroforestry disserve to produces has higher insecticidal activity, and minimum is 81.9%, the highest by 100%.Find that the restraining effect that these 5 kinds of compounds grow insect is obvious by the investigation of the inhibiting rate that grows to examination worm, within 5 days, all can reach 100%, polypide only has about 1/4th of contrast simultaneously.
The impact of table 25 kind of indole carbazole alkaloid and percentage of pupation heavy on cabbage caterpillar pupa
For examination insect Compound Pupa heavy (g) Percentage of pupation (%)
Cabbage caterpillar (Pieris rapae) 1 0.018 11.3
Cabbage caterpillar (Pieris rapae) 2 0.029 19.7
Cabbage caterpillar (Pieris rapae) 3 0.032 27.6
Cabbage caterpillar (Pieris rapae) 4 0.025 20.8
Cabbage caterpillar (Pieris rapae) 5 0.021 23.6
Contrast 0.094 98.0
From table 2 data, heavy and percentage of pupation has very strong restraining effect to cabbage caterpillar pupa for 5 compounds, and contrast examination worm pupa weighs 0.094, and percentage of pupation reaches 98%, and the heavy 0.018-0.032 of process examination worm pupa, percentage of pupation only has 11.3%-27.6%.Success percentage of pupation reduces 70.4%-86.7%, the above results prove these 5 compounds to the growth of tested insect, survive and pupate that all there is very strong restraining effect, can as the potentiality bacterial strain of development new pesticides.
Although be described above object lesson of the present invention, having a bit is obvious to those skilled in the art, namely can make various changes the present invention and change under the premise without departing from the spirit and scope of the present invention.In protection scope of the present invention, modify for above-described embodiment, add and replace, it does not all exceed protection scope of the present invention.

Claims (3)

1. several indole carbazole alkaloid and producing bacterial strain with strong insecticidal activity, described indole carbazole alkaloid compound producing bacterial strain CQT14-24, for habitat, ocean streptomyces nitrosporeus Streptomyces nitrosporus, CQT14-24 bacterial strain is through artificial culture, obtain fermented product to extract through conventional chemical processes again, can obtain 4 indole carbazole alkaloids and 1 anthraquinone analog compound, 5 compounds all have strong lethal effect to various plants insect, and its feature comprises the steps:
1) with its deposit number be: the bacterial strain CQT14-24 of CGMCC No.4607, be placed in following solid medium and cultivate 5 days, then fermentation culture in the fermented liquid proceeding to same recipe, culture medium prescription is: Zulkovsky starch 15-20g, soya bean leaching juice 150-200ml, ooze leaching juice 100-150ml, KNO 31.1-1.5g, K 2hPO 40.4-0.8g, MgSO 40.5-0.8g, NaCl, 12-20g, KCl0.04-0.09g, MgCl 20.23-0.50g, FeSO47H 2o0.01-0.03g, vitamin complex 1mL/L, water 650-750ml, pH7-7.5, not adding agar is nutrient solution, and adding agar 16-19g is solid medium, 25 DEG C-26 DEG C rotating speed 150rpm, and shaking culture obtains fermented product in 11 days, and fermented product is divided into thalline and bacterium liquid;
2) be extracted with ethyl acetate 3 times after bacterium liquid concentrating under reduced pressure, after revolving steaming, obtain medicinal extract; Thalline ethyl acetate supersound extraction, merge with bacterium immersion cream after medicinal extract tlc analysis, reduced pressure chromatography, sherwood oil: acetone (20: 1), methylene dichloride: methyl alcohol (1: 1), methyl alcohol is wash-out respectively, by methylene dichloride: ODS column separating purification on methyl alcohol, use methyl alcohol respectively: water (2: 3) and 100% methanol-eluted fractions, obtain 4 indole carbazole alkaloids and 1 anthraquinone compounds with gel filtration chromatography, HPLC chromatogram conventional isolation techniques.
2. the preparation method with strong insecticidal activity indole carbazole alkaloid and anthraquinone compounds according to claim 1, it is characterized in that: the structure of 5 described compounds is Des (hydroxyimino)-TAN1030A (1), holyrine A (2), RK-1409 (3), Streptocarbazoles B (4), K1115A (5), wherein compound 1-4 is indole carbazole alkaloid, and 5 is anthraquinone analog compound.
3. several indole carbazole alkaloid and producing bacterial strain with strong insecticidal activity according to claim 1, it is characterized in that: 4 described indole carbazole alkaloids and 1 anthraquinone analog compound ordinary method test activity, the cabbage caterpillar (Pieris rapae) common to agricultural and harm is serious, brevicoryne brassicae (Brevicoryne brassicae), fall webworms (Hyphantria cunea), small cabbage moth (Plutella xyllostella), mythimna separata (Mythimna separata), the growth of bollworm (Helicoverpa armigera), survive and pupate that all there is very strong insecticidal activity, its corrected mortality can reach 81.9%-100%, polypide severe decrease, the inhibiting rate of growth is 100%, percentage of pupation reduces 70.4%-86.7%.
CN201310547718.8A 2013-10-31 2013-10-31 A plurality of indolocarbazole alkaloids having strong insect disinfestation activities, and production strain thereof Pending CN104593281A (en)

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CN114349762B (en) * 2020-10-13 2023-01-03 中国科学院南海海洋研究所 6/6/6/6/5/5 cyclic alkaloid compounds with novel frameworks and application thereof in preparation of antibacterial drugs
CN114009451A (en) * 2021-11-15 2022-02-08 中国科学院南海海洋研究所 Application of deep-sea actinomycetes 11791 in preparation of medicine for preventing and treating lepidoptera pests in agriculture and animal husbandry
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