CN113973831B - Application of camelnine A derivative in treatment of plant virus germ disease - Google Patents
Application of camelnine A derivative in treatment of plant virus germ disease Download PDFInfo
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Abstract
The invention relates to an application of a camelina A derivative in treating plant viruses and germ diseases, and the invention discovers that the camelina A derivatives I-1 to I-17 show good activity of resisting plant viruses and germ and can well inhibit Tobacco Mosaic Virus (TMV) and cucumber wilt, peanut brown spots, apple ring spots, wheat sheath blight, corn small spots, watermelon anthrax, rice bakanae, tomato early blight, wheat gibberella, rice blast, phytophthora capsici, rape sclerotium, cucumber gray mold and rice sheath blight 14 plant germs.
Description
Technical Field
The invention relates to application of camelnine A derivatives in treating plant virus and germ diseases, and belongs to the technical field of agricultural protection.
Background
The camelning alkaloid A is an alkaloid separated from camel artemisia. In 2003, the university of virginia Hecht group of subjects (j.am. Chem. Soc.2003, 125, 13628-13629.) found that camelinine a showed inhibitory effect on mouse tumor cell P388 cell lines in vitro, IC thereof 50 1.8. Mu.g/mL. At the end of 2003, this group of subjects (bioorg. Med. Chem 2004, 12, 6287-6299.) demonstrated that camelinine a was able to stabilize the "DNA-topo I" covalent binary complex between the DNA phosphodiester backbone and topoisomerase I. Thus, it was demonstrated that it has a similar mechanism of action to camptothecin, and is capable of inhibiting the activity of topoisomerase I. In 2004, the university of eastern river, zhongze Ma group (bioorg. Med. Chem. Lett.2004, 14, 1193-1196) and the like reported that camelinine a also exhibited significant inhibitory activity against human topoisomerase II. Camelinine has biological activity on specific human cancer cells, no report on the aspect of preventing and treating plant virus germ diseases of camelinine A exists so far, and camelinine A is enough to be a good lead compound for developing new medicines.
Disclosure of Invention
The invention provides application of camelnine A derivatives I in prevention and treatment of plant virus germ diseases. The camelnine A derivative I of the patent has good activity of resisting plant viruses and pathogens.
The camelning alkali A derivative is shown as a general formula I, and specifically is I-1 to I-17.
Compared with the prior art, the invention discovers that the camelinine A derivatives I-1-I-17 show good plant virus and germ resistance activity, and can well inhibit Tobacco Mosaic Virus (TMV), cucumber wilt, peanut brown spots, apple ring, wheat sheath blight, corn small spots, watermelon anthracnose, rice bakanae, tomato early blight, wheat gibberella, rice blast, phytophthora capsici, rape sclerotium, cucumber gray mold and rice sheath blight 14 plant germs.
Detailed Description
In the examples of the present invention, the structural formulae I-1 to I-4 of camelnine A derivatives were prepared according to the following references: molecular 2012, 17, 11363-11378.I-5 to I-6 are prepared according to the following references: res. Chem. Inter. Med.2016, 42, 1045-1055.I-7 is prepared according to the following references: tetrahedron letters 2012, 53, 2643-2646.I-8 to I-17 are prepared according to the following references: org.Lett.2016, 18, 824-827.
Example 1: experimental data of structural formulas of camelning A derivatives I-1 to I-17
I-1: white solid, melting point 208-210 ℃. 1 H NMR(400MHz，DMSO-d 6 )δ8.78(s，1H)，8.32-8.27(m，2H)，8.18(d，J＝8.1Hz，1H)，7.98-7.89(m，3H)，7.78(t，J＝7.5Hz，1H)，7.68-7.62(m，1H)，5.33(s，2H). 13 C NMR(100MHz，DMSO-d 6 )δ160.2，153.6，152.0，149.5，148.8，135.0，132.3，131.5，133.0，130.2，129.0，128.8，128.5，127.7，126.4，48.0.
I-2: pale red solid, melting point 272-274 ℃. 1 H NMR(400MHz，DMSO-d 6 )δ8.66(s，1H)，8.30(d，J＝7.8Hz，1H)，8.18(d，J＝8.7Hz，1H)，7.96-7.93(m，3H)，7.78-7.74(m，1H)，7.67-7.61(m，1H)，5.31(s，2H)，2.58(s，3H).
I-3: yellow-green solid with melting point of 280-282 ℃. 1 H NMR(400MHz，DMSO-d 6 )δ8.55(s，1H)，8.29(d，J＝7.6Hz，1H)，7.97-7.88(m，2H)，7.68-7.60(m，2H)，7.54(s，1H)，5.28(s，2H)，4.00(d，J＝10.1Hz，6H).
I-4: white solid with melting point > 300 ℃. 1 H NMR(400MHz，DMSO-d 6 )δ8.74(s，1H)，8.35(d，J＝2.2Hz，1H)，8.31-8.28(m，2H)，7.97-7.90(m，3H)，7.68-7.62(m，1H)，5.33(s，2H).
I-5: reddish brown solid with melting point of 188-190 ℃, 1 H NMR(400MHz，DMSO-d 6 )δ8.23-8.18(m，1H)，8.15-8.10(m，1H)，8.02(d，J＝3.3Hz，1H)，7.91-7.85(m，1H)，7.75(d，J＝8.0Hz，1H)，7.53(t，J＝7.1Hz，1H)，7.37-7.30(m，1H)，7.30-7.21(m，4H)，7.18(d，J＝6.8Hz，2H)，6.93(d，J＝8.0Hz，1H)，6.82(t，J＝7.5Hz，1H). 13 C NMR(100MHz，DMSO-d 6 )δ159.7，147.7，147.3，145.1，139.4，135.0，133.7，128.6，128.2，127.2，126.9，126.7，126.2，125.7，119.9，118.8，115.9，115.5，62.5.
i-6: yellow solid, melting point 237-239 ℃, 1 H NMR(400MHz，DMSO-d 6 )δ8.25(d，J＝7.0Hz，1H)，8.09(dd，J＝7.9，1.0Hz，1H)，7.91-7.85(m，1H)，7.79(d，J＝8.0Hz，1H)，7.77-7.70(m，2H)，7.54-7.47(m，1H)，7.38(d，J＝3.8Hz，1H)，7.36-7.29(m，1H)，7.22(dd，J＝8.4，2.1Hz，1H)，6.93-6.83(m，3H). 13 C NMR(100MHz，DMSO-d 6 )δ159.2，147.7，147.3，143.5，135.8，135.1，133.9，133.8，132.4，129.6，127.7，127.3，127.1，126.9，126.4，119.8，119.2，116.2，115.1，60.7.
i-7: yellow solid with a melting point of 200-202 ℃, 1 H NMR(400MHz，DMSO-d 6 )δ9.29(s，1H)，8.72(d，J＝7.9Hz，1H)，8.32(d，J＝7.9Hz，1H)，7.97(t，J＝7.6Hz，1H)，7.90(t，J＝7.5Hz，1H)，7.84(d，J＝7.9Hz，2H)，7.73(t，J＝7.5Hz，1H)，7.60(t，J＝7.5Hz，1H). 13 C NMR(100MHz，DMSO-d 6 )δ158.7，147.1，144.5，142.9，138.1，135.9，133.8，128.9，127.7，127.3，127.0，126.5，125.4，121.2，118.7.
i-8: black solid, melting point 208-210 ℃, 1 H NMR(400MHz，CDCl 3 )δ8.85(d，J＝7.2Hz，1H)，8.42(d，J＝8.0Hz，1H)，7.87-7.72(m，2H)，7.54-7.40(m，3H)，6.91-6.80(m，1H). 13 C NMR(100MHz，CDCl 3 )δ159.0，148.6，147.8，135.1，134.1，127.4，126.9，126.7，126.4，125.3，116.3，112.5.
i-9: yellow solid with a melting point of 164-166 ℃, 1 H NMR(400MHz，CDCl 3 )δ8.89(d，J＝7.5Hz，1H)，8.10(d，J＝8.6Hz，1H)，7.90-7.80(m，1H)，7.69-7.61(m，1H)，7.54(s，2H)，6.97-6.86(m，1H). 13 C NMR(100MHz，CDCl 3 )δ160.9，158.4，158.4(d，J＝3.8Hz)，147.1(d，J＝1.9Hz)，145.4，133.9，129.5(d，J＝8.1Hz)，126.4(d，J＝6.3Hz)，124.5(d，J＝25.1Hz)，117.0(d，J＝8.6Hz)，112.9，111.2(d，J＝23.5Hz).
i-10: yellow solid with melting point of 122-124 ℃, 1 H NMR(400MHz，CDCl 3 )δ8.81(d，J＝7.3Hz，1H)，8.35(d，J＝2.1Hz，1H)，7.76-7.65(m，2H)，7.54-7.41(m，2H)，6.90-6.79(m，1H). 13 C NMR(100MHz，CDCl 3 )δ157.1，146.8，146.1，134.6，133.4，127.7，125.7，125.4，125.3，116.0，112.0.
i-11: yellow solid with a melting point of 135-137 ℃, 1 H NMR(400MHz，CDCl 3 )δ8.88(d，J＝7.4Hz，1H)，8.25(s，1H)，7.75-7.65(m，2H)，7.55-7.45(m，2H)，6.85(s，1H)，2.54(s，3H). 13 C NMR(100MHz，CDCl 3 )δ158.9，147.1，146.7，136.9，135.4，133.6，126.7，126.7，126.3，126.2，116.1，112.3.21.4.
i-12: yellow solid with melting point of 158-160 ℃, 1 H NMR(400MHz，CDCl 3 )δ8.85(d，J＝7.4Hz，1H)，7.77-7.69(m，2H)，7.51-7.40(m，3H)，6.87-6.80(m，1H)，3.94(s，3H). 13 C NMR(100MHz，CDCl 3 )δ158.7，157.4，146.1，143.7，132.8，128.7，126.8，126.4，116.9，112.6，105.1，55.9.
i-13: yellow solid with a melting point of 155-157 ℃, 1 H NMR(400MHz，CDCl 3 )δ9.20(s，1H)，8.45(d，J＝8.1Hz，1H)，7.89(t，J＝7.7Hz，1H)，7.80(d，J＝8.3Hz，1H)，7.58-7.46(m，3H). 13 C NMR(100MHz，CDCl 3 )δ157.5，147.1，145.6，134.7，127.9，126.7，126.5，126.3，125.6(q，J＝5.8Hz)，125.3，121.7(q，J＝342.5Hz)，115.6，115.5.
i-14: yellow solid with a melting point of 162-164 ℃, 1 H NMR(400MHz，CDCl 3 )δ8.99(d，J＝1.8Hz，1H)，8.44(dd，J＝8.2，1.1Hz，1H)，7.88-7.82(m，1H)，7.77(d，J＝8.3Hz，1H)，7.54-7.46(m，2H)，7.38(d，J＝9.6Hz，1H). 13 C NMR(100MHz，CDCl 3 )δ158.0，148.2，145.9，137.5，135.3，127.5，127.4，127.2，126.6，126.0，116.3，107.7.
i-15: yellow solid with a melting point of 148-150 ℃, 1 H NMR(400MHz，DMSO-d 6 )δ8.63(s，1H)，8.31(d，J＝8.1Hz，1H)，7.89(t，J＝7.7Hz，1H)，7.74(d，J＝8.3Hz，1H)，7.62(d，J＝9.3Hz，1H)，7.54-7.46(m，2H)，2.34(s，3H). 13 C NMR(100MHz，CDCl 3 )δ163.1，153.3，151.7，143.3，139.9，131.8，130.5，130.0，128.2，127.8，125.7，120.8，22.9.
i-16: yellow solid with a melting point of 142-144 ℃, 1 H NMR(400MHz，CDCl 3 )δ8.39(d，J＝8.2Hz，1H)，7.95(d，J＝5.0Hz，1H)，7.81(t，J＝7.1Hz，1H)，7.69(d，J＝8.3Hz，1H)，7.47(t，J＝7.6Hz，1H)，6.85(d，J＝5.1Hz，1H). 13 C NMR(100MHz，CDCl 3 )δ158.7，158.1，148.4，135.0，127.1，126.2，125.4，121.2，116.5，109.5.
i-17: white solid with melting point of 188-190 ℃, 1 H NMR(400MHz，CDCl 3 )δ9.05(d，J＝8.5Hz，1H)，8.45(d，J＝7.5Hz，1H)，7.82(t，J＝7.1Hz，1H)，7.75-7.60(m，2H)，7.55-7.41(m，3H). 13 C NMR(100MHz，CDCl 3 )δ159.7，155.9，146.2，135.1，133.9，126.1，125.8，125.7，124.9，124.8，122.7，120.7，118.2，117.6.
example 2: the tobacco mosaic virus resistance activity was measured as follows:
1. virus purification and concentration determination:
the virus purification and concentration measurement are carried out by compiling tobacco mosaic virus SOP standard according to a measuring room generated by elements of university of south China. After 2 times of polyethylene glycol centrifugation treatment, the concentration of the virus crude extract is measured, and the virus crude extract is refrigerated at 4 ℃ for standby.
2. Compound solution preparation:
after weighing, adding DMF to dissolve the raw materials to obtain 1×10 5 Mu g/mL mother liquor, and then diluting the mother liquor to the required concentration by using an aqueous solution containing 1 per mill of Tween 80; the Ningnan mycin preparation is directly diluted by water.
3. Living body protecting action:
3-5 She Qishan Xiyan with uniform growth vigor is selected, the whole plant is sprayed and applied, each treatment is repeated for 3 times, and 1 permillage of Tween 80 aqueous solution is used for comparison. After 24h, the leaf surface is spread with silicon carbide (500 meshes), the whole leaf surface is dipped with a virus liquid by a writing brush, the whole leaf surface is lightly rubbed for 2 times along the branch pulse direction, the lower part of the leaf surface is supported by a palm, the virus concentration is 10 mug/mL, and the leaf surface is washed by running water after inoculation. And after 3d, recording the number of the lesions, and calculating the control effect.
4. In vivo therapeutic action:
3-5 She Qishan Xiyan with uniform growth vigor is selected, the whole leaf of the writing brush is inoculated with virus, the virus concentration is 10 mug/mL, and the whole leaf is washed by running water after inoculation. After leaf surface is dried, spraying and applying the whole plant, repeating for 3 times every treatment, and setting 1%Tween 80 water solution as a control. And after 3d, recording the number of the lesions, and calculating the control effect.
5. In vivo passivation:
selecting 3-5 She Qishan Xie smoke with uniform growth vigor, mixing the medicament with an equal volume of virus juice, inactivating for 30min, performing friction inoculation, wherein the virus concentration is 20 mug/mL, washing with running water after inoculation, repeating for 3 times, and setting 1 milltween 80 water solution for comparison. And counting the number of lesions after 3d, and calculating a result.
Inhibition ratio (%) = [ (control number of dried spots-treated number of dried spots)/control number of dried spots ] ×100%
Firstly, performing in-vivo deactivation, in-vivo treatment and in-vivo protection activity tests of all compounds at a treatment dose of 500 mug/mL, and performing in-vivo deactivation, in-vivo treatment and in-vivo protection activity tests of all compounds with a relative inhibition rate of more than 40% at a treatment dose of 500 mug/mL and in-vivo protection activity tests of all compounds at a treatment dose of 100 mug/mL. The positive control is commercial anti-plant virus agents ribavirin and ningnanmycin.
Table 1 results of test of anti-Tobacco Mosaic Virus (TMV) Activity of Aldriin A derivatives I-1 to I-17
As can be seen from the data in Table one, the camelning base A derivatives I-1 to I-17 all show good anti-TMV activity, and under the condition of 500 mug/mL, the activity of most compounds is equivalent to that of ribavirin, the antiviral activity of I-9 and I-11 is equivalent to that of Ningnanmycin, so that the camelning base A derivatives have great development value.
Example 3: antibacterial activity was tested, and the assay procedure was as follows:
in vitro sterilization test, cell growth rate assay (plate method):
a certain amount of medicament is dissolved in a proper amount of acetone, then the mixture is diluted to a required concentration by using an aqueous solution containing 200 mu g/mL of emulsifier, then 1mL of liquid medicament is respectively absorbed and injected into a culture dish, 9mL of culture medium is respectively added, and a 50 mu g/mL medicament-containing plate is prepared after shaking uniformly, and a plate added with 1mL of sterilized water is used as a blank control. The trays were cut along the outer edge of the mycelium with a punch of 4mm diameter and transferred to a medicated plate. Each treatment was repeated three times. The dishes were placed in a constant temperature incubator at 24.+ -. 1 ℃. After 48 hours, the expanded diameter of each treatment bacterial disc is investigated, the average value is calculated, and the relative antibacterial rate is calculated compared with a blank control.
Table 2 results of in vitro bactericidal activity test of camelnine a derivatives I-1 to I-17:
the camelnine A derivative shows broad-spectrum inhibition activity on 14 tested bacteria at a test concentration of 50 mug/mL. The bacteriostatic activity of the compounds I-12 and I-15 on apple banded is 89% and the bacteriostatic activity of the compounds I-9 and I-15 on apple banded are 91% respectively, and the inhibition rate of the compounds I-9 and I-16 on rice banded is 88% and 100% respectively.
The endpoints and any values of the ranges disclosed herein are not limited to the precise range or value, and are understood to encompass values approaching those ranges or values. For numerical ranges, one or more new numerical ranges may be found between the endpoints of each range, between the endpoint of each range and the individual point value, and between the individual point value, in combination with each other, and are to be considered as specifically disclosed herein.
The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, a number of simple variants of the technical solution of the invention are possible, including combinations of the individual technical features in any other suitable way, which simple variants and combinations should likewise be regarded as being disclosed by the invention, all falling within the scope of protection of the invention.
Claims (2)
1. The application of camelnine A derivative I in treating tobacco mosaic virus is characterized in that the camelnine A derivative I is specifically a compound shown as I-8-I-15, R 1 And R is 2 Is a functional group shown in structures I-8 to I-15:
2. the use of compounds I-8 to I-15 according to claim 1 for the treatment of cucumber fusarium wilt, apple ring rot, wheat sheath blight, watermelon anthracnose, rice bakanae disease, tomato early blight, wheat scab, potato late blight, pepper phytophthora blight, rape sclerotinia or rice sheath blight.
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