CN113004148A - Resveratrol derivative and preparation method and application thereof - Google Patents

Resveratrol derivative and preparation method and application thereof Download PDF

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CN113004148A
CN113004148A CN202110239422.4A CN202110239422A CN113004148A CN 113004148 A CN113004148 A CN 113004148A CN 202110239422 A CN202110239422 A CN 202110239422A CN 113004148 A CN113004148 A CN 113004148A
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resveratrol
resveratrol derivative
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acyl chloride
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CN113004148B (en
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于秀玲
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Linyi University
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Abstract

The invention belongs to the technical field of pesticides, and particularly relates to a resveratrol derivative, and a preparation method and application thereofApplication is carried out. The invention provides a resveratrol derivative, which has a structural formula shown as a formula I or a formula II, wherein R1And R2Is heterocyclic radical, substituted heterocyclic radical, aryl, substituted aryl, branched chain alkyl or cycloalkyl.

Description

Resveratrol derivative and preparation method and application thereof
Technical Field
The invention belongs to the technical field of pesticides, and particularly relates to a resveratrol derivative and a preparation method and application thereof.
Background
Plant viruses are various in types and are widely distributed, plant virus diseases are called plant cancers, and the plant virus diseases are second only to fungi in agricultural production. Most commercial crops suffer from reduced yield or reduced quality to varying degrees due to the damage of plant viruses. Plant viruses are absolutely parasitic in plant cells, and substances, energy and sites required for replication are completely provided by host cells, and have high dependence on the host plant cells. Since plants do not have an intact immune system as animals, the control of plant viral diseases has been a major problem in the control of plant diseases.
Tobacco Mosaic Virus (TMV) is a plant Virus with strong infectivity and great harm. The host range is very wide, and the plant can infect solanaceae plants such as tomato, eggplant, potato, pepper, black nightshade and the like besides tobacco, and can infect more than 300 plants of 30 families such as cucurbitaceae, polygonaceae, cruciferae, leguminosae, lividae, compositae and the like. The focus of scientists has been how to prevent and control tobacco mosaic virus.
Figure BDA0002961587500000011
At present, few effective and satisfactory plant virus inhibitors are available, fewer therapeutic agents are available, and most of the reported agents have the control effect of less than 60% when being actually applied in the field. Ribavirin (ribavirin) is widely used for preventing and treating diseases caused by TMV, but the drug has the inhibition rate of less than 50 percent on the TMV at the concentration of 500 mu g/mL. Ningnanmycin (ningnanmycin) has only a preventive effect and a poor therapeutic effect. NK-007 is also in the industrial development stage. To date, once plants are infected with tobacco mosaic virus, there is no chemical pesticide that can completely cure it. Therefore, the development of more practical and efficient plant virus inhibitors remains a very difficult task.
The natural active substance has diversity, uniqueness and novelty of structure and biological activity, and is an important source for creating new medicines. At present, people find a lot of natural active substances with insecticidal, bactericidal, antiviral and herbicidal effects in wild plant resources, and the development and utilization of the wild plant resources to synthesize biopesticides such as botanical insecticides, bactericides, antiviral agents, herbicides and the like have great development potential and economic value. Pesticides of natural origin are the hot spots for research and development of pesticides. The natural active substances of the pesticides are good lead compounds, and the targeted and personalized modification and improvement of the nature and the deficiency of the natural products are the most important scientific research subjects in the prior pesticide chemist.
Resveratrol (Resveratrol), known by the chemical name 3, 4', 5-trihydroxy-1, 2-stilbene (also known as Resveratrol), is a non-flavonoid natural polyphenol compound containing stilbene structures.
Figure BDA0002961587500000021
Resveratrol is a phytoalexin produced by many plants under fungal, viral, ultraviolet or pathological conditions, and can improve the resistance of plants to pathogens and protect plants. However, resveratrol has poor drug-forming property and cannot be directly developed as a drug.
Disclosure of Invention
In view of the above, the present invention provides a resveratrol derivative. The invention improves the drug property of the resveratrol derivative by modifying resveratrol and introducing other groups. Part of the resveratrol derivatives provided by the invention have better inhibition effect on tobacco mosaic virus and part of the resveratrol derivatives have better insecticidal effect.
In order to solve the technical problems, the invention provides a resveratrol derivative, which has a structural formula shown as a formula I or a formula II:
Figure BDA0002961587500000022
wherein R is1And R2Is heterocyclic radical, substituted heterocyclic radical, aryl, substituted aryl, branched chain alkyl or cycloalkyl.
Preferably, the first and second liquid crystal materials are,the R is1Included
Figure BDA0002961587500000023
Preferably, said R is1Included
Figure BDA0002961587500000024
R' comprises H3CO-、F-、Cl-、Br-、O2N-、CH3-、(CH3)3C-or F3CO-。
Preferably, said R is1Including CH3-CH2-、CH3-CH2-CH2-or
Figure BDA0002961587500000025
Preferably, said R is2Included
Figure BDA0002961587500000031
Preferably, said R is2Included
Figure BDA0002961587500000032
R' includes F-, Cl-, Br-, O2N-、CH3-or (CH)3)3C-。
Preferably, said R is2Including CH3-CH2-、CH2＝CH-、
Figure BDA0002961587500000033
The invention also provides a preparation method of the resveratrol derivative in the technical scheme, which comprises the following steps:
mixing resveratrol, dichloromethane, triethylamine and an acyl chloride-based compound, and carrying out esterification reaction to obtain the resveratrol derivative, wherein the acyl chloride-based compound comprises acyl chloride or sulfonyl chloride, when the acyl chloride-based compound is sulfonyl chloride, the resveratrol derivative with the structure shown in the formula I is obtained, and when the acyl chloride-based compound is acyl chloride, the resveratrol derivative with the structure shown in the formula II is obtained;
the acyl chloride comprises heterocyclic group substituted acyl chloride, substituted heterocyclic group substituted acyl chloride, aryl substituted acyl chloride, substituted aryl substituted acyl chloride, branched chain alkyl substituted acyl chloride or cycloalkyl substituted acyl chloride;
the sulfonyl chloride comprises heterocycle substituted sulfonyl chloride, substituted heterocycle substituted sulfonyl chloride, aryl substituted sulfonyl chloride, substituted aryl substituted sulfonyl chloride, branched chain alkyl substituted sulfonyl chloride or cycloalkyl substituted sulfonyl chloride.
The invention also provides application of the resveratrol derivative in the technical scheme or the application of the resveratrol derivative prepared by the preparation method in the technical scheme in plant disease and pest control.
Preferably, when R is1Is composed of
Figure BDA0002961587500000034
CH3-CH2-or
Figure BDA0002961587500000035
The application is the application of the resveratrol derivative with the structure shown in the formula I in inhibiting tobacco mosaic virus;
when R is2Is composed of
Figure BDA0002961587500000036
CH2＝CH-、CH3-CH2-、
Figure BDA0002961587500000037
The application is the application of the resveratrol derivative with the structure shown in the formula II in inhibiting tobacco mosaic virus.
Preferably, when R is1Is composed of
Figure BDA0002961587500000038
CH3-CH2-CH2-or
Figure BDA0002961587500000039
The application is the application of the resveratrol derivative with the structure shown in the formula I in plant disinsection;
when R is2Is composed of
Figure BDA0002961587500000041
CH3-CH2-、CH2＝CH-、
Figure BDA0002961587500000042
The application is the application of the resveratrol derivative with the structure shown in the formula II in plant disinsection.
Preferably, the application is in plant antibiosis.
The invention provides a resveratrol derivative, which has a structural formula shown as a formula I or a formula II:
Figure BDA0002961587500000043
wherein R is1And R2Is heterocyclic radical, substituted heterocyclic radical, aryl, substituted aryl, branched chain alkyl or cycloalkyl. In the present invention, when R is1Is composed of
Figure BDA0002961587500000044
CH3-CH2-or
Figure BDA0002961587500000045
When the resveratrol derivative with the structure shown in the formula I is used, the resveratrol derivative has a good inhibition effect on tobacco mosaic virus; when the concentration of the mosaic virus is 500 mug/mL, the in-vivo inactivation inhibition rate of the resveratrol derivative on the mosaic virus is 34.5-61.9%. When R is2Is composed of
Figure BDA0002961587500000046
CH2＝CH-、CH3-CH2-、
Figure BDA0002961587500000047
When the resveratrol derivative with the structure shown in the formula II is used, the resveratrol derivative has a good inhibition effect on tobacco mosaic virus; the in-vivo inactivation inhibition rate of the resveratrol derivative on mosaic virus is 49.8-57.2%. In the present invention, when R is1Is composed of
Figure BDA0002961587500000048
CH3-CH2-CH2-or
Figure BDA0002961587500000049
In time, the resveratrol derivative with the structure shown in the formula I has good plant insecticidal property; when R is2Is composed of
Figure BDA0002961587500000051
CH3-CH2-、CH2＝CH-、
Figure BDA0002961587500000052
In addition, the resveratrol derivative with the structure shown in the formula II has good plant insecticidal property.
Detailed Description
The invention provides a resveratrol derivative, which has a structural formula shown as a formula I or a formula II:
Figure BDA0002961587500000053
wherein R is1And R2Is heterocyclic radical, substituted heterocyclic radical, aryl, substituted aryl, branched chain alkyl or cycloalkyl.
In the present invention, when R is1When it is a heterocyclic group, the heterocyclic group preferably includes
Figure BDA0002961587500000054
The resveratrol derivative preferably has a structure shown in a formula I-1:
Figure BDA0002961587500000055
when R is1When substituted aryl, the substituted aryl preferably has a formula comprising
Figure BDA0002961587500000056
R' preferably comprises H3CO-、F-、Cl-、Br-、O2N-、CH3-、(CH3)3C-or F3CO-; the structural formula of the substituted aryl group is more preferably
Figure BDA0002961587500000057
Figure BDA0002961587500000058
The resveratrol derivative is preferably a compound with a structure shown in formulas I-2-I-10:
Figure BDA0002961587500000061
when R is1When it is a branched hydrocarbon group or a cycloalkyl group, the branched hydrocarbon group preferably includes CH3-CH2-or CH3-CH2-CH2Preferably, the resveratrol derivative has a structure shown in a formula I-11 or I-12:
Figure BDA0002961587500000062
said cycloalkyl group preferably comprises
Figure BDA0002961587500000063
The resveratrol derivative is preferably a compound with a structure shown in a formula I-13:
Figure BDA0002961587500000071
in the present invention, when R is2When it is a heterocyclic group, the heterocyclic group preferably includes
Figure BDA0002961587500000072
More preferably
Figure BDA0002961587500000073
The resveratrol derivative preferably has a structure shown in formulas II-1-II-4:
Figure BDA0002961587500000074
when R is2When substituted aryl, the substituted aryl preferably has a formula comprising
Figure BDA0002961587500000075
R' preferably includes F-, Cl-, Br-, O2N-、CH3-or (CH)3)3C-; the structural formula of the substituted aryl group is more preferably
Figure BDA0002961587500000076
The resveratrol derivative preferably has a structure shown in formulas II-5-II-14:
Figure BDA0002961587500000081
when R is2When it is a branched hydrocarbon group or a cycloalkyl group, the branched hydrocarbon group preferably includes CH3-CH2-or CH2CH-; the resveratrol derivative preferably has a structure shown in formulas II-15-II-16:
Figure BDA0002961587500000082
said cycloalkyl group preferably comprises
Figure BDA0002961587500000083
The resveratrol derivative preferably has a structure shown in formulas II-17-II-18:
Figure BDA0002961587500000084
the invention also provides a preparation method of the resveratrol derivative in the technical scheme, which comprises the following steps:
mixing resveratrol, dichloromethane, triethylamine and an acyl chloride-based compound, and carrying out esterification reaction to obtain the resveratrol derivative, wherein the acyl chloride-based compound comprises acyl chloride or sulfonyl chloride, when the acyl chloride-based compound is sulfonyl chloride, the resveratrol derivative with the structure shown in the formula I is obtained, and when the acyl chloride-based compound is acyl chloride, the resveratrol derivative with the structure shown in the formula II is obtained;
the acyl chloride comprises heterocyclic group substituted acyl chloride, substituted heterocyclic group substituted acyl chloride, aryl substituted acyl chloride, substituted aryl substituted acyl chloride, branched chain alkyl substituted acyl chloride or cycloalkyl substituted acyl chloride;
the sulfonyl chloride comprises heterocycle substituted sulfonyl chloride, substituted heterocycle substituted sulfonyl chloride, aryl substituted sulfonyl chloride, substituted aryl substituted sulfonyl chloride, branched chain alkyl substituted sulfonyl chloride or cycloalkyl substituted sulfonyl chloride.
The resveratrol derivative is prepared by mixing resveratrol, dichloromethane, triethylamine and an acyl chloride-based compound, and carrying out esterification reaction, wherein the acyl chloride-based compound comprises acyl chloride or sulfonyl chloride, when the acyl chloride-based compound is sulfonyl chloride, the resveratrol derivative with the structure shown in the formula I is obtained, and when the acyl chloride-based compound is acyl chloride, the resveratrol derivative with the structure shown in the formula II is obtained. In the present invention, the mixing preferably comprises the steps of:
carrying out first mixing on resveratrol and dichloromethane to obtain a resveratrol solution;
carrying out second mixing on the resveratrol solution and triethylamine to obtain a mixed solution;
and dropwise adding acyl chloride or sulfonyl chloride into the mixed solution.
The method comprises the step of carrying out first mixing on resveratrol and dichloromethane to obtain a resveratrol solution. In the invention, the dichloromethane is used as a solvent, and the dichloromethane is preferably anhydrous dichloromethane. The dosage of the dichloromethane is not specially limited, as long as the resveratrol can be completely dissolved. The first mixing is not particularly limited as long as the first mixing can be uniformly mixed.
After the resveratrol solution is obtained, the resveratrol solution and triethylamine are subjected to second mixing to obtain a mixed solution. In the invention, the triethylamine is used as an acid-binding agent to promote the esterification reaction. In the invention, the molar ratio of the resveratrol to the triethylamine is preferably 1: 4-5. The second mixing is not particularly limited as long as the second mixing can be uniformly mixed.
After the mixed solution is obtained, acyl chloride or sulfonyl chloride is dripped into the mixed solution. In the invention, the molar ratio of the resveratrol to the acyl chloride is preferably 1: 4-5. In the invention, the molar ratio of the resveratrol to the sulfonyl chloride is preferably 1: 4-5. In the present invention, the dropwise addition is preferably performed under stirring, and the rotation speed of the stirring is not particularly limited in the present invention, as long as the dropwise addition of the acid chloride or sulfonyl chloride and resveratrol can be sufficiently mixed. In the present invention, the dropwise addition is preferably carried out in an ice-water bath to avoid too rapid esterification. In the invention, the dripping speed is preferably 28-32 drops/min, and more preferably 30 drops/min. The dropping time is not particularly limited, and the dropping can be completed.
In the invention, the temperature of the esterification reaction is preferably room temperature, and more preferably 25-30 ℃. The present invention preferably utilizes TLC to detect the completion of the esterification reaction.
In the invention, the sulfonyl chloride comprises heterocyclic group substituted sulfonyl chloride, substituted heterocyclic group substituted sulfonyl chloride, aryl substituted sulfonyl chloride, substituted aryl substituted sulfonyl chloride, branched chain alkyl substituted sulfonyl chloride or cycloalkyl substituted sulfonyl chloride, and preferably heterocyclic group substituted sulfonyl chloride, aryl substituted sulfonyl chloride, substituted aryl substituted sulfonyl chloride, branched chain alkyl substituted sulfonyl chloride or cycloalkyl substituted sulfonyl chloride. In the present invention, the heterocyclic group-substituted sulfonyl chloride preferably includes
Figure BDA0002961587500000101
The substituted aryl-substituted sulfonyl chloride preferably comprises
Figure BDA0002961587500000102
Figure BDA0002961587500000103
Figure BDA0002961587500000104
The branched alkyl-substituted sulfonyl chloride preferably comprises
Figure BDA0002961587500000105
Figure BDA0002961587500000106
Said cycloalkyl-substituted sulfonyl chloride preferably comprises
Figure BDA0002961587500000107
In the invention, the acyl chloride comprises heterocycle substituted acyl chloride, substituted heterocycle substituted acyl chloride, aryl substituted acyl chloride, substituted aryl substituted acyl chloride, branched alkyl substituted acyl chloride or cycloalkyl substituted acyl chloride, and preferably heterocycle substituted acyl chloride, aryl substituted acyl chloride, substituted aryl substituted acyl chloride, branched alkyl substituted acyl chloride or cycloalkyl substituted acyl chloride. In the present invention, the heterocycle-substituted acid chloride preferably includes
Figure BDA0002961587500000108
The substituted aryl-substituted acid chloride preferably comprises
Figure BDA0002961587500000111
Figure BDA0002961587500000112
The branched hydrocarbyl-substituted acid chloride preferably comprises
Figure BDA0002961587500000113
The cycloalkyl-substituted acid chlorides preferably include
Figure BDA0002961587500000114
Figure BDA0002961587500000115
When the esterification reaction is completed, the present invention also preferably comprises:
mixing the esterification reaction product with water, and then carrying out liquid separation to obtain a first organic phase and a first water phase;
extracting the first water phase twice by using dichloromethane, and combining organic phases obtained by two extractions to obtain a second organic phase;
and combining the first organic phase and the second organic phase, and then sequentially washing, drying, filtering and recrystallizing to obtain the resveratrol derivative.
The present invention does not have any special limitation on the liquid separation and extraction, and the methods known to those skilled in the art can be adopted. In the present invention, the washing solvent is preferably a saturated saline solution; the drying agent is preferably anhydrous sodium sulfate. The suction filtration is not particularly limited in the present invention, and may be performed in a manner known to those skilled in the art. In the present invention, the solvent for recrystallization is preferably a mixture of ethyl acetate and petroleum ether; the volume ratio of the ethyl acetate to the petroleum ether is preferably 1: 20-80, and more preferably 1: 50.
The invention also provides application of the resveratrol derivative in the technical scheme or the application of the resveratrol derivative prepared by the preparation method in the technical scheme in plant disease and pest control. In the invention, the application comprises the application in inhibiting tobacco mosaic virus, the application in plant antibiosis or the application in plant disinsection.
In the present invention, when R is1Is composed of
Figure BDA0002961587500000121
CH3-CH2-or
Figure BDA0002961587500000122
The application is the application of the resveratrol derivative with the structure shown in the formula I in inhibiting tobacco mosaic virus; when R is2Is composed of
Figure BDA0002961587500000123
Figure BDA0002961587500000124
CH2＝CH-、CH3-CH2-、
Figure BDA0002961587500000125
The application is the application of the resveratrol derivative with the structure shown in the formula II in inhibiting tobacco mosaic virus.
In the present invention, when R is1Is composed of
Figure BDA0002961587500000126
CH3-CH2-CH2-or
Figure BDA0002961587500000127
The application refers to the application of the resveratrol derivative with the structure shown in the formula I in plant disinsection; when R is2Is composed of
Figure BDA0002961587500000128
Figure BDA0002961587500000129
CH3-CH2-、CH2＝CH-、
Figure BDA00029615875000001210
The application is the application of the resveratrol derivative with the structure shown in the formula II in plant disinsection. In the present invention, the pesticidal pest preferably includes oriental armyworm, cotton bollworm, corn borer or mosquito larva.
In the invention, the antibacterial strain is preferably a fungus, and the fungus preferably comprises tomato early blight, wheat gibberellic disease, potato late blight, phytophthora capsici, sclerotinia sclerotiorum, cucumber gray mold, rice sheath blight, cucumber wilt, peanut brown spot, apple ring rot, rice bakanae, corn microspore, watermelon anthrax or wheat sheath blight.
In the present invention, the pre-application preferably comprises: and mixing the resveratrol derivative with a solvent to obtain a resveratrol derivative solution. In the present invention, the solvent preferably includes N, N-dimethylformamide and a tween solution. In the present invention, the mixing preferably comprises the steps of:
thirdly, mixing the resveratrol and the N, N-dimethylformamide to obtain resveratrol derivative mother liquor;
and fourthly, mixing the resveratrol derivative mother liquor with 1 per mill of aqueous solution of tween-80 to obtain the resveratrol derivative solution.
The third mixing and the fourth mixing are not particularly limited in the present invention as long as they can be mixed uniformly.
In the invention, when the resveratrol derivative solution is applied to inhibiting tobacco mosaic virus, the concentration of the resveratrol derivative solution is preferably 100-500 mug/mL; when the resveratrol derivative solution is applied to plant antibiosis, the concentration of the resveratrol derivative solution is 50 mug/mL; when the resveratrol derivative solution is applied to plant disinsection, the concentration of the resveratrol derivative solution is preferably 100-600 mu g/mL.
According to the invention, the resveratrol is modified, acyl or sulfonyl is introduced, the stability of the resveratrol is improved, and the resveratrol derivative has good antiviral activity to tobacco mosaic virus and also has good bactericidal activity and insecticidal activity.
In order to further illustrate the present invention, the following embodiments are described in detail, but they should not be construed as limiting the scope of the present invention.
Example 1
Mixing 0.1g resveratrol (0.438mmol) and 20mL dichloromethane (water content of 0%) to obtain resveratrol solution;
mixing the resveratrol solution with 0.22g of triethylamine (2.19mmol) to obtain a mixed solution;
placing the mixed solution in an ice-water bath, stirring, dropwise adding 0.31g of benzoyl chloride (2.19mmol) into the mixed solution at the dropwise adding rate of 30 drops/min, and carrying out esterification reaction at room temperature; mixing the product of the esterification reaction with water for liquid separation to obtain a first organic phase and a first water phase; extracting the first water phase twice by using dichloromethane, and combining organic phases obtained by two extractions to obtain a second organic phase; mixing the first organic phase and the second organic phase, and washing twice by using saturated salt solution; drying the washed product by using anhydrous sodium sulfate, and performing suction filtration to obtain filter residue; mixing the filter residue with a mixture of ethyl acetate and petroleum ether (the volume ratio of ethyl acetate to petroleum ether is 1: 50), and recrystallizing to obtain 0.23g
Figure BDA0002961587500000131
(yield: 96%, melting point: 170 to 172 ℃ C.).
Performing high-resolution mass spectrometric detection on the obtained resveratrol derivative to obtain1H NMR(400MHz,CDCl3)δ8.22(m,6H),7.71–7.61(m,3H),7.60–7.48(m,8H),7.36–7.30(m,2H),7.15(m,5H)；13C NMR(100MHz,CDCl3)δ165.13,164.86,151.70,150.73,139.75,134.56,133.83,133.70,130.27,130.23,129.80,129.45,129.25,128.68,128.63,127.78,127.27,122.09,117.24,114.82；HRMS(ESI)(m/z):calcd for C35H24O6[M+NH4]+558.1911,found 558.1911。
Examples 2 to 19
Resveratrol derivatives were prepared according to the procedure of example 1, the specific acid chloride structures and the amounts used are referenced in table 1.
TABLE 1 Structure and amount of acid chloride used in preparation of resveratrol derivatives
Figure BDA0002961587500000141
Figure BDA0002961587500000151
The results of performing high resolution mass spectrometry on the resveratrol derivatives prepared in examples 2-19 are as follows.
Example 21H NMR(400MHz,CDCl3)δ8.28–8.20(m,6H),7.56(d,J＝8.0Hz,2H),7.31(d,J＝2.0Hz,2H),7.25–7.17(m,8H),7.15–7.04(m,3H)；13C NMR(100MHz,CDCl3)δ164.45(d,J＝119Hz,1C),164.14,151.56,150.62,139.80,134.59,132.89(d,J＝9Hz,1C),132.90,132.80,129.87,127.80,127.24,125.47,122.05,117.24,116.05,115.97,115.83,115.74,114.72；HRMS(ESI)(m/z):calcd for C35H21F3O6[M+NH4]+612.1628,found612.1630。
Example 31H NMR(400MHz,CDCl3)δ8.14–8.07(m,6H),7.55(d,J＝8.4Hz,2H),7.36–7.28(m,8H),7.24–7.02(m,5H),2.46(s,9H)；13C NMR(100MHz,CDCl3)δ165.16,164.89,151.76,150.79,144.64,144.50,139.66,134.50,130.29,130.26,129.73,129.38,129.32,127.72,127.30,126.72,126.54,122.10,117.16,114.86,21.80；HRMS(ESI)(m/z):calcd for C38H30O6[M+NH4]+600.2381,found 600.2379。
Example 41H NMR(400MHz,CDCl3)δ8.14–8.11(m,4H),8.07(d,J＝8.4Hz,2H),7.55–7.47(m,9H),7.30(d,J＝2.0Hz,2H),7.21(d,J＝8.4Hz,2H),7.13–7.04(m,2H)；13C NMR(100MHz,CDCl3)δ164.24,163.96,161.30,151.51,150.58,141.42,140.43,140.26,139.83,134.61,131.89,131.60,129.89,129.38,129.08,129.00,127.81,122.00,117.23,114.62；HRMS(ESI)(m/z):calcd for C35H21Cl3O6[M+NH4]+660.0742,found 660.0731。
Example 51H NMR(400MHz,CDCl3)δ8.08–8.05(m,4H),7.99(d,J＝8.0Hz,2H),7.68–7.65(m,6H),7.55(d,J＝8.4Hz,2H),7.31(d,J＝2.0Hz,2H),7.22(d,J＝8.4Hz,2H),7.17–7.03(m,3H)；13C NMR(100MHz,CDCl3)δ164.43,164.13,161.46,151.48,150.55,139.84,134.61,132.41,132.10,132.01,131.95,131.70,129.90,129.18,128.08,127.82,127.20,122.01,117.25,114.63；HRMS(ESI)(m/z):calcd for C35H21Br3O6[M+NH4]+793.9206,found 793.9171。
Example 61H NMR(400MHz,CDCl3)δ8.42–8.27(m,12H),7.59(d,J＝8.4Hz,2H),7.38(d,J＝2.0Hz,2H),7.27(d,J＝8.0Hz,2H),7.23–7.06(m,3H)；13C NMR(100MHz,CDCl3)δ162.97,151.28,151.09,150.39,140.11,134.79,134.46,131.40,131.37,130.95,130.20,128.86,127.97,127.15,123.89,123.80,123.72,121.91,117.40,114.37；HRMS(ESI)(m/z):calcd for C35H21N3O12[M-OH]-658.1092,found 657.9651。
Example 71H NMR(400MHz,CDCl3)δ8.21–8.15(m,3H),7.57(d,J＝8.4Hz,2H),7.52–7.47(m,3H),7.36–7.31(m,8H),7.22(d,J＝8.4Hz,2H),7.15–7.05(m,3H),2.70(s,6H),2.68(s,3H)；13C NMR(100MHz,CDCl3)δ165.74,165.38,151.70,150.68,141.57,141.43,139.72,134.54,132.96,132.83,132.06,132.01,131.30,131.21,129.75,128.18,127.75,127.29,126.02,125.96,122.19,117.26,114.98,22.07,22.00；HRMS(ESI)(m/z):calcd for C38H30O6[M+NH4]+600.2381,found 600.2379。
Example 81H NMR(400MHz,CDCl3)δ8.04–8.00(m,6H),7.56(d,J＝8.4Hz,2H),7.47–7.38(m,6H),7.32(d,J＝2.0Hz,2H),7.23(t,J＝8.0Hz,2H),7.18–7.04(m,3H),2.46(s,6H),2.45(s,3H)；13C NMR(100MHz,CDCl3)δ165.27,164.98,151.77,150.80,139.72,138.51,138.46,134.56,134.44,130.77,130.72,129.78,129.41,129.23,128.55,128.50,127.75,127.42,127.37,127.32,122.08,117.17,114.80,21.32；HRMS(ESI)(m/z):calcd for C38H30O6[M+NH4]+600.2381,found 600.2379。
Example 91H NMR(400MHz,CDCl3)δ7.59(d,J＝8.4Hz,2H),7.33(d,J＝1.6Hz,2H),7.27–7.24(m,2H),7.17–7.06(m,3H),6.95–6.91(m,6H),2.48(s,12H),2.46(s,6H),2.33(s,6H),2.32(s,3H)；13C NMR(100MHz,CDCl3)δ168.31,167.88,151.62,150.56,140.27,140.09,139.80,135.93,135.69,134.62,129.85,129.51,128.79,128.70,127.86,127.33,121.95,117.04,114.26,21.23,20.24,20.07；HRMS(ESI)(m/z):calcd for C44H42O6[M+NH4]+684.3320,found 684.3316。
Example 101H NMR(400MHz,CDCl3)δ8.16–8.12(m,6H),7.57–7.52(m,8H),7.30(d,J＝2.0Hz,2H),7.21(d,J＝8.6Hz,2H),7.14–7.02(m,3H),1.38(s,18H),1.37(s,9H)；13C NMR(100MHz,CDCl3)δ165.11,164.86,157.62,157.49,151.78,150.80,139.66,134.51,130.18,130.14,129.74,127.74,127.30,126.66,126.47,125.67,125.61,122.12,117.19,114.87,35.25,31.14；HRMS(ESI)(m/z):calcd for C47H48O6[M+NH4]+726.3789,found726.4049。
Example 111H NMR(400MHz,CDCl3)δ7.47(d,J＝8.4Hz,2H),7.13–6.91(m,6H),6.83(t,J＝2.0Hz,1H),1.89–1.79(m,3H),1.22–1.14(m,6H),1.07–0.99(m,6H)；13C NMR(100MHz,CDCl3)δ173.44,173.11,151.40,150.52,139.42,134.36,129.55,127.59,127.19,121.92,116.82,114.50,13.04,9.40,9.35；HRMS(ESI)(m/z):calcd for C26H24O6[M+NH4]+450.1911,found 450.1914。
Example 121H NMR(400MHz,CDCl3)δ7.47(d,J＝8.4Hz,2H),7.08(.m,J＝1.6Hz,3H),7.04(d,J＝5.12Hz,2H),7.00–6.91(m,1H),6.82–6.72(m,1H),2.60–2.50(m,3H),2.12–2.02(m,6H),1.87–1.78(m,6H),1.71–1.68(m,2H),1.65–1.55(m,6H),1.43–1.24(m,10H)；13C NMR(100MHz,CDCl3)δ174.47,174.11,151.56,150.65,139.44,134.34,129.55,127.58,127.20,121.88,116.73,114.42,43.22,28.94,25.72,25.36；HRMS(ESI)(m/z):calcd for C35H42O6[M+NH4]+576.3320,found 576.3323。
Example 131H NMR(400MHz,CDCl3)δ7.93–7.86(m,3H),7.62–7.57(m,6H),7.53(d,J＝8.6Hz,2H),7.46–7.38(m,10H),7.25(d,J＝2.3Hz,2H),7.18(d,J＝8.6Hz,2H),7.15–6.98(m,3H),6.67–6.61(m,3H)；13C NMR(100MHz,CDCl3)δ165.36,165.04,151.52,150.57,147.07,146.80,139.62,134.51,134.16,134.11,130.86,130.79,129.70,129.06,128.98,128.41,128.36,127.73,127.30,121.98,117.19,117.01,114.58；HRMS(ESI)(m/z):calcd for C41H30O6[M+NH4]+636.2381,found 636.2383。
Example 141H NMR(400MHz,CDCl3)δ7.48(d,J＝8.4Hz,2H),7.11(d,J＝2.0Hz,2H),7.10–7.07(m,2H),7.05–6.92(m,2H),6.82(t,J＝2.0Hz,1H),2.63–2.56(m,6H),1.27(t,J＝7.6Hz,9H)；13C NMR(100MHz,CDCl3)δ172.92,172.57,151.41,150.52,139.50,134.39,129.60,127.63,127.20,121.89,116.82,114.41,27.78,9.08,9.05；HRMS(ESI)(m/z):calcd for C23H24O6[M+NH4]+414.1911,found 414.1910。
Example 151H NMR(400MHz,CDCl3)δ7.48(d,J＝8.5Hz,2H),7.13–7.11(m,2H),7.10–7.07(m,2H),7.05–6.93(m,2H),6.84–6.81(m,1H),2.31(s,9H)；13C NMR(100MHz,CDCl3)δ169.45,169.04,151.32,150.44,139.55,134.48,129.67,127.68,127.20,121.91,116.93,114.42,21.14；HRMS(ESI)(m/z):calcd for C23H18O6[M-H2O]+372.0997,found372.1443。
Example 161H NMR(400MHz,CDCl3)δ9.45–9.39(m,3H),8.92–8.85(m,3H),8.51–8.44(m,3H),7.58(d,J＝8.4Hz,1H),7.54–7.47(m,4H),7.37(d,J＝1.6Hz,1H),7.25–7.20(m,2H),7.17–7.14(m,1H),7.12–6.92(m,3H)；13C NMR(100MHz,CDCl3)δ163.79,163.49,154.18,151.36,151.26,137.77,134.74,130.08,127.91,127.76,127.19,125.33,123.65,123.60,121.96,121.85,117.37；HRMS(ESI)(m/z):calcd for C32H21N3O6[M+H]+544.1503,found 544.1505。
Example 171H NMR(400MHz,CDCl3)δ8.34–8.29(m,3H),7.69–7.65(m,3H),7.53(d,J＝8.6Hz,2H),7.40–7.36(m,3H),7.29(d,J＝2.0Hz,2H),7.20(d,J＝8.6Hz,2H),7.16–7.01(m,3H)；13C NMR(100MHz,CDCl3)δ160.96,160.65,151.42,150.47,139.70,134.54,134.35,134.17,132.78,132.56,129.77,128.24,127.76,127.26,126.55,126.45,122.06,117.19,114.74；HRMS(ESI)(m/z):calcd for C29H18O6S3[M+NH4]+576.0604,found 576.0605。
Example 181H NMR(400MHz,CDCl3)δ8.03–7.96(m,3H),7.71–7.65(m,3H),7.54(d,J＝8.3Hz,2H),7.34–7.29(m,2H),7.23(d,J＝8.4Hz,2H),7.20–7.16(m,3H),7.13–7.01(m,3H)；13C NMR(100MHz,CDCl3)δ160.50,160.19,151.27,150.37,139.70,134.99,134.81,134.61,133.88,133.64,132.78,132.52,129.84,128.15,128.09,127.76,127.25,122.01,117.22,114.62；HRMS(ESI)(m/z):calcd for C29H18O6S3[M+NH4]+576.0604,found 576.0605。
Example 191H NMR(400MHz,CDCl3)δ7.73–7.66(m,3H),7.53(d,J＝7.9Hz,2H),7.43–7.37(m,3H),7.32–7.28(m,2H),7.22(d,J＝8.1Hz,2H),7.15–6.98(m,3H),6.64–6.56(m,3H)；13C NMR(100MHz,CDCl3)δ156.83,156.46,150.92,149.99,147.46,147.27,143.89,143.68,139.76,134.65,129.88,127.81,127.23,121.95,119.87,119.63,117.21,114.48,112.32,112.26；HRMS(ESI)(m/z):calcd for C29H18O9[M+NH4]+528.1289,found 528.1291。
From the mass spectrum data of examples 1 to 19, it can be seen that the resveratrol derivatives prepared in examples 1 to 19 were obtained.
Example 20
Mixing 0.3g resveratrol (1.3mmol) and 25mL dichloromethane (water content 0%) to obtain a first solution;
mixing the first solution with 0.506g triethylamine (5.2mmol) to obtain a second solution;
placing the second solution inStirring in an ice-water bath, dropwise adding 1.075g of p-methoxybenzenesulfonyl chloride (5.2mmol) into the second solution at the dropping rate of 30 drops/min, and carrying out esterification reaction at room temperature; mixing the product of the esterification reaction with water for liquid separation to obtain a first organic phase; extracting the water phase obtained by liquid separation twice by using dichloromethane, and combining organic phases obtained by two extractions to obtain a second organic phase; mixing the first organic phase and the second organic phase, and washing twice by using saturated salt solution; drying the washed product by using anhydrous sodium sulfate, and performing suction filtration to obtain filter residue; mixing the filter residue with a mixture of ethyl acetate and petroleum ether (the volume ratio of ethyl acetate to petroleum ether is 1: 50), and recrystallizing to obtain 0.77g
Figure BDA0002961587500000191
(yield: 86%, melting point: 154 to 156 ℃ C.).
Examples 21 to 36
Resveratrol derivatives were prepared according to the procedure of example 20, with specific sulfonyl chloride structures and amounts referenced in table 2.
TABLE 2 Structure of sulfonyl chloride and its amount in preparation of resveratrol derivatives
Figure BDA0002961587500000201
Figure BDA0002961587500000211
The results of high resolution mass spectrometry detection of the resveratrol derivatives prepared in examples 20 to 36 are as follows.
Example 201H NMR(400MHz,CDCl3)δ7.80–7.68(m,6H),7.36(d,J＝8.4Hz,2H),7.05(s,2H),7.03–6.94(m,8H),6.83(d,J＝4.7Hz,2H),6.46(s,1H),3.89(s,9H)；13C NMR(100MHz,CDCl3)δ164.40,164.19,150.05,149.46,139.79,135.10,130.79,130.76,127.86,126.91,126.52,126.04,122.93,119.03,115.75,114.57,114.38,55.84；HRMS(ESI)(m/z):calcd for C35H30O12S3[M+NH4]+756.1238,found 756.1242。
Example 211HNMR(400MHz,CDCl3)δ7.60(d,2H),7.33(d,J＝1.9Hz,2H),7.24(s,2H),7.19–7.06(m,3H),6.97–6.91(m,6H),2.57–2.39(m,18H),2.37–2.27(m,9H)；13C NMR(100MHz,CDCl3)δ168.34,167.90,151.60,150.54,140.28,140.10,139.80,135.93,135.69,134.62,129.85,129.49,128.80,128.70,127.86,127.31,121.95,117.06,114.27,21.25,20.26,20.08；HRMS(ESI)(m/z):calcd for C41H42O9S3[M-C7H6]+684.1527,found 684.3310。
Example 221HNMR(400MHz,CDCl3)δ7.86(dt,J＝6.5,4.5Hz,6H),7.39(d,J＝8.6Hz,2H),7.29–7.19(m,7H),7.09(d,J＝2.1Hz,2H),7.00(d,J＝8.6Hz,2H),6.87(q,J＝16.3Hz,2H),6.55–6.49(m,1H)；13C NMR(100MHz,CDCl3)δ166.25(d,J＝258Hz,1C),166.10(d,J＝256Hz,1C),149.82,149.29,140.16,135.24,131.42(d,J＝10.0Hz,1C),131.39(d,J＝10.0Hz,1C),131.23(d,J＝4.0Hz,1C),130.88(d,J＝4.0Hz,1C),130.50,128.06,126.83,122.81,119.13,117.00,116.78,116.56,115.53；HRMS(ESI)(m/z):calcd for C32H21F3O9S3[M+NH4]+720.0638,found 720.0641。
Example 231HNMR(400MHz,CDCl3)δ7.80–7.73(m,6H),7.58–7.48(m,6H),7.40(d,J＝7.9Hz,2H),7.09(s,2H),7.00(d,J＝7.8Hz,2H),6.94–6.80(m,2H),6.52(d,J＝1.2Hz,1H)；13C NMR(100MHz,CDCl3)δ149.80,149.28,141.55,141.20,140.20,135.26,133.70,133.35,130.57,129.93,129.86,129.81,129.62,128.11,126.84,122.79,119.12,115.46；HRMS(ESI)(m/z):calcd for C32H21Cl3O9S3[M+NH4]+769.9722,found769.9718。
Example 241H NMR(400MHz,CDCl3)δ7.74–7.66(m,12H),7.41(d,J＝8.6Hz,2H),7.08(d,J＝2.0Hz,2H),7.00(d,J＝8.6Hz,2H),6.92–6.81(m,2H),6.53(t,J＝1.9Hz,1H)；13C NMR(100MHz,CDCl3)δ149.81,149.29,140.23,135.28,134.29,133.95,132.82,132.61,130.59,130.16,129.95,129.87,128.14,126.86,122.78,119.10,115.44；HRMS(ESI)(m/z):calcd for C32H21Br3O9S3[M+NH4]+903.8195,found 903.8180。
Example 251H NMR(400MHz,CDCl3)δ8.51–8.44(m,6H),8.19–8.11(m,6H),7.57(d,J＝8.7Hz,2H),7.37(d,J＝2.1Hz,2H),7.26–7.14(m,2H),7.11(d,J＝8.7Hz,2H),6.75(t,J＝2.1Hz,1H)；13C NMR(100MHz,CDCl3)δ151.20,151.07,149.03,148.54,148.38,140.70,139.37,138.81,135.77,130.58,130.08,130.05,128.51,126.92,125.10,125.01,122.49,119.45；HRMS(ESI)(m/z):calcd for C32H21N3O15S3[M+NH4]+801.0473,found 801.0438。
Example 261HNMR(400MHz,CDCl3)δ7.76–7.65(m,6H),7.40–7.30(m,8H),7.05(d,J＝1.6Hz,2H),6.98(d,J＝8.5Hz,2H),6.90–6.76(m,2H),6.47(s,1H),2.46(s,9H)；13C NMR(100MHz,CDCl3)δ150.01,149.43,145.92,145.55,139.81,135.14,132.27,131.86,130.22,129.99,129.84,128.54,128.47,127.87,126.91,122.86,118.99,115.65,21.81,21.77；HRMS(ESI)(m/z):calcd for C35H30O9S3[M+NH4]+708.1390,found708.1397。
Example 271HNMR(400MHz,CDCl3)δ8.14(dd,J＝8.5,2.7Hz,5H),7.59–7.46(m,8H),7.30(d,J＝1.8Hz,2H),7.21(dd,J＝19.9,11.4Hz,3H),7.08(dd,J＝21.3,14.1Hz,3H),1.40–1.36(m,24H),1.35(s,3H)；13C NMR(100MHz,CDCl3)δ165.12,164.87,157.63,157.51,151.80,150.82,139.68,134.52,130.19,130.14,129.75,127.74,127.32,126.68,126.49,125.67,125.62,125.50,122.12,117.19,114.87,35.26,31.14；HRMS(ESI)(m/z):calcd for C44H48O9S3[M-C7H6]+726.1996,found 726.3790。
Example 281HNMR(400MHz,CDCl3)δ7.70–7.58(m,6H),7.53–7.38(m,6H),7.36(d,J＝8.6Hz,2H),7.04(d,J＝2.0Hz,2H),6.99(d,J＝8.6Hz,2H),6.89–6.78(m,2H),6.52(t,J＝2.0Hz,1H),2.44(s,9H)；13C NMR(100MHz,CDCl3)δ149.95,149.39,139.87,139.82,139.63,135.43,135.17,134.78,130.23,129.18,129.04,128.73,128.71,127.88,126.88,125.66,125.58,122.85,119.05,115.68,21.34；HRMS(ESI)(m/z):calcd for C35H30O9S3[M+NH4]+708.1390,found 708.1397。
Example 291HNMR(400MHz,CDCl3)δ7.87–7.80(m,6H),7.74–7.66(m,3H),7.59–7.53(m,6H),7.35(d,J＝8.6Hz,2H),7.04(d,J＝2.0Hz,2H),6.98(d,J＝8.6Hz,2H),6.88–6.76(m,2H),6.49(t,J＝2.0Hz,1H)；13C NMR(100MHz,CDCl3)δ149.93,149.37,139.91,135.29,135.18,134.90,134.65,134.38,130.30,129.40,129.24,128.51,128.46,127.93,126.84,122.83,119.05,115.62；HRMS(ESI)(m/z):calcd for C32H24O9S3[M+NH4]+666.0921,found 666.0918。
Example 301HNMR(400MHz,CDCl3)δ7.84–7.76(m,3H),7.75–7.66(m,3H),7.40(d,J＝8.6Hz,2H),7.35–7.27(m,6H),7.18(d,J＝1.9Hz,2H),7.12(d,J＝8.6Hz,2H),6.94–6.80(m,2H),6.75(s,1H)；13C NMR(100MHz,CDCl3)δ160.64,158.09(d,J＝10.0Hz,1C),149.66,149.11,140.19,137.23(d,J＝8.0Hz,1C),136.92(d,J＝8.0Hz,1C),135.37,131.46,131.38,130.44,128.11,126.88,124.61(d,J＝4.0Hz,1C),124.74(d,J＝4.0Hz,1C),123.14,123.01,122.52,118.98,117.63(d,J＝2.0Hz,1C),117.50(d,J＝2.0Hz,1C),115.11；HRMS(ESI)(m/z):calcd for C32H21F3O9S3[M+NH4]+720.0638,found720.0640。
Example 311HNMR(400MHz,CDCl3)δ7.93–7.88(m,6H),7.41–7.35(m,8H),7.10(d,J＝1.6Hz,2H),7.01(d,J＝8.4Hz,2H),6.93–6.81(m,2H),6.57(s,1H)；13C NMR(100MHz,CDCl3)δ153.62,153.41,149.72,149.23,140.24,135.29,133.38,133.01,130.80,130.77,130.53,130.35,128.08,126.80,122.76,121.01,120.79,119.16,118.86,115.57；HRMS(ESI)(m/z):calcd for C35H21O12F9S3[M+NH4]+918.0390,found 918.0387。
Example 321H NMR(400MHz,CDCl3)δ7.52–7.40(m,17H),7.12(d,J＝8.6Hz,2H),7.08(d,J＝2.0Hz,2H),6.98–6.83(m,2H),6.71(t,J＝2.0Hz,1H),4.54(s,6H)；13C NMR(100MHz,CDCl3)δ149.63,149.01,140.23,135.25,130.96,130.90,130.38,129.54,129.40,129.15,129.07,128.13,127.11,126.89,126.85,122.46,118.63,115.13,57.23,56.95；HRMS(ESI)(m/z):calcd for C35H30O9S3[M+NH4]+708.1390,found 708.1394。
Example 331HNMR(400MHz,CDCl3)δ7.53(d,J＝8.7Hz,2H),7.37(d,J＝2.1Hz,2H),7.30–7.27(m,2H),7.12–7.09(m,1H),7.04–6.86(m,2H),3.39–3.28(m,6H),1.61–1.53(m,9H)；13C NMR(100MHz,CDCl3)δ149.57,140.53,135.30,130.56,128.30,128.09,126.94,122.47,118.70,115.15,45.61,45.23,8.29；HRMS(ESI)(m/z):calcd for C20H24O9S3[M+NH4]+522.0921,found 522.0911。
Example 341HNMR(400MHz,CDCl3)δ7.54(d,J＝7.0Hz,2H),7.37(s,2H),7.30–7.24(m,2H),7.18–6.96(m,3H),3.34–3.23(m,6H),2.12–1.98(m,6H),1.20–1.10(m,9H)；13C NMR(100MHz,CDCl3)δ149.57,148.96,140.50,135.29,130.55,128.29,126.98,122.49,118.71,115.19,52.57,52.27,17.37,12.89,12.86；HRMS(ESI)(m/z):calcd for C23H30O9S3[M+NH4]+564.1390,found 564.1390。
Example 351HNMR(400MHz,CDCl3)δ7.53(d,J＝8.6Hz,2H),7.40(d,J＝1.9Hz,2H),7.32(d,J＝8.6Hz,2H),7.20–7.17(m,1H),7.15–6.98(m,2H),2.69–2.60(m,3H),1.33–1.27(m,6H),1.22–1.13(m,6H)；13C NMR(100MHz,CDCl3)δ150.08,149.50,140.32,135.28,130.51,128.16,126.98,122.76,118.99,115.80,28.01,27.87,6.45,6.30；HRMS(ESI)(m/z):calcd for C23H24O9S3[M+NH4]+558.0921,found 558.0918。
Example 361HNMR(400MHz,CDCl3)δ7.77(d,J＝5.0Hz,2H),7.74(d,J＝5.0Hz,1H),7.65–7.59(m,3H),7.41(d,J＝8.6Hz,2H),7.17–7.11(m,5H),7.05(d,J＝8.6Hz,2H),6.95–6.82(m,2H),6.58(s,1H)；13C NMR(100MHz,CDCl3)δ150.01,149.46,140.05,135.84,135.57,135.39,135.17,134.73,134.58,134.02,130.45,128.01,127.86,127.62,126.93,122.73,119.21,115.45；HRMS(ESI)(m/z):calcd for C26H18O9S6[M+NH4]+683.9613,found 683.9613。
From the mass spectrum data of examples 20 to 36, it can be seen that the resveratrol derivatives prepared in examples 20 to 36 were obtained.
The inhibitory effect of the resveratrol derivatives prepared in examples 9, 10, 14, 15, 17, 19, 21, 24, 29, 33 and 35 on tobacco mosaic virus was examined as follows:
TMV plant virus was purified by the polyethylene glycol precipitation method of Leberman, the extracted virus was a milky white precipitate, and the mass concentration C (mg/mL) of the virus was calculated as A260/3.1 from the A260 absorption.
Preparing a resveratrol derivative solution:
dissolving resveratrol derivative in DMF to obtain resveratrol with mass concentration of 1 × 105Mu g/mL of resveratrol derivative mother liquor, and then diluting the resveratrol derivative mother liquor by using a water solution of Tween-80 with the mass concentration of 1 per mill to obtain resveratrol derivative solutions with the mass concentrations of 500 mu g/mL and 100 mu g/mL respectively.
Preparation of a comparative solution:
dissolving resveratrol in DMF to obtain resveratrol with mass concentration of 1 × 105Mu g/mL of resveratrol mother liquor, and diluting the resveratrol mother liquor with 1 per mill of Tween-80 aqueous solution to obtain solutions with mass concentrations of 500 mu g/mL or 100 mug/mL resveratrol solution;
the medicine ribavirin is directly diluted by water to obtain ribavirin solution with the concentration of 500 mug/mL or 100 mug/mL.
In vivo protection against TMV infection:
selecting 3-5 leaf-period Shanxi tobacco with uniform growth vigor, spraying the whole plant (only spraying uniformly), and repeating the test of each group for 3 times to obtain an average value; meanwhile, the mass percent concentration of the Tween-80 aqueous solution is 1 per mill; after 24h, the leaf surfaces are scattered with carborundum (500 meshes), the virus liquid is dipped by a writing brush, the whole leaf surfaces are lightly wiped for 2 times along the branch vein direction, the lower parts of the leaf surfaces are supported by palms, the virus concentration is 10 mu g/mL, and the inoculated leaf surfaces are washed by running water. The number of lesions was recorded after 3 days and the control effect was calculated and the results are shown in table 3.
In vivo therapeutic effect on TMV infection:
selecting 3-5-leaf Saxismoke with uniform growth vigor, inoculating viruses with the whole leaves of a writing brush, wherein the virus concentration is 10 mu g/mL, and washing with running water after inoculation; after the leaves are harvested, spraying the whole plant (only spraying is uniform), and repeating the test of each group for 3 times to obtain an average value; and setting the mass percent concentration of 1 per mill of Tween-80 aqueous solution as a reference; the number of lesions was recorded after 3 days and the control effect was calculated and the results are shown in Table 3.
In vivo inactivation of TMV infection
Selecting 3-5-leaf-period Saxifraga, mixing and passivating the medicament solution and virus juice with the same volume for 30min, performing friction inoculation, wherein the virus concentration is 20 mug/mL, washing with running water after inoculation, and repeating 3 times for each group of tests to obtain an average value; comparing with 1 per mill Tween-80 aqueous solution; the number of lesions was counted after 3 days, and the results were shown in Table 3.
Y/% ([ (C-a)/C ] × 100, wherein: y is the inhibition rate of the compound on tobacco mosaic virus spots; c is the number of control group lesions, unit: a plurality of; a is the number of lesions in the treatment group, unit: a plurality of; the number of lesions in the control and treatment groups was averaged over 3 replicates in each group.
TABLE 3 resveratrol derivatives inhibiting tobacco mosaic Virus Activity
Figure BDA0002961587500000261
Figure BDA0002961587500000271
As is clear from the data results in table 3, the resveratrol derivatives prepared in examples 9, 10, 14, 15, 17, 19, 21, 24, 29, 33 and 35 had excellent inhibitory effect on tobacco mosaic virus.
The bactericidal performance of the resveratrol derivatives prepared in examples 1-36 was tested as follows:
the plant fungi were inoculated on PDA medium for 7 days, plates with a diameter of 4cm were prepared on the edges of the colonies using a punch, and inoculated on PDA medium containing 50. mu.g/mL and containing no drug for 4 days, the diameters of the colonies were measured, and the percent sterilization by the drug was calculated as compared with the control group, and the results are shown in Table 4. Wherein the fungus comprisesaAverage ofthree replicates.bC, Fusarium oxysporum f.sp.cucumeris (cucumber wilting); h, Cercospora arachidicola hori (peanut brown speck); p, physiosporiracila (apple ring); r.c, Rhizoctonia cerealis (rice sapling); B.M, Bipolaris maydis (corn speckles); W.A, Watermelon anthracnose (Watermelon anthrax); F.M, Fusarium moniliforme (wheat grain withered); A.S, Alternaria solani (tomato early blight); F.G, Fusarium graminearum (Gibberella tritici); p.i., Phytophthora infestans (potato late blight); P.C Phytophthora capsicii (Phytophthora capsici); S.S., sclerotia sclerotiorum (sclerotium napus); r.s, Rhizoctonia solani (rice sheath blight); B.C, Botrytis cinerea (Botrytis cinerea).
TABLE 4 fungicidal Properties of resveratrol derivatives
Figure BDA0002961587500000272
Figure BDA0002961587500000281
Figure BDA0002961587500000291
The data in table 4 show that the resveratrol derivative provided by the invention has certain bactericidal performance.
The insecticidal performance of the resveratrol derivatives prepared in examples 1-3, 6-8, 10-19, 24, 25, 28, 32 and 36 was tested as follows:
activity test of oriental armyworm:
the leaf soaking method comprises the steps of preparing 600 mu g/mL resveratrol derivative solution, soaking leaves with the diameter of about 5-6 cm into the liquid medicine for 6s, taking out, placing on absorbent paper for airing, placing in a specified culture dish, inoculating 10-head 3-year-old larvae, placing in an insect room at 27 +/-1 ℃ for observation for 4 days, and then checking results, wherein the results are shown in Table 5.
Activity test of mosquito larvae:
the test object is the normal group of Culex pipiens which is bred indoors and has light color. Weighing the test medicine in a medicine bottle, adding a proper amount of acetone, and oscillating for dissolving to obtain a mother solution. Diluting with distilled water to desired concentration, selecting 10 4-year-old primary mosquito larvae, pouring into a beaker together with the medicinal liquid, placing into a standard processing chamber, and inspecting the result after 1 day; the results are shown in Table 5 using a blank of aqueous solution containing the test solvent.
Cotton bollworm activity test:
the test was carried out at the bio-testing platform of the pesticide engineering center of southern kaiki university by using the feed-mixing method, and 3mL of the prepared solution was transferred and added to about 27g of freshly prepared feed for cotton bollworms (corn flour, soybean flour, sucrose, agar, yeast powder, vitamins, preservatives) to obtain the desired concentration of ten times dilution. The preparation was mixed and poured into a clean 24-well plate, and then inoculated into 24-day 3-old cotton bollworms after cooling, and the results were examined after 4 days, and are listed in table 5.
Activity test of corn borer:
the leaf dipping method comprises the steps of preparing a solution of 600 mu g/mL, dipping leaves with the diameter of about 5-6 cm into the liquid medicine for 6s, taking out the leaves, putting the leaves on absorbent paper for airing, putting the leaves in a specified culture dish, inoculating 10 larvae of 3 years old, putting the larvae in an insect-raising room with the temperature of 27 +/-1 ℃, observing 4 days, and checking results, wherein the results are shown in Table 5.
TABLE 5 insecticidal Activity of resveratrol derivatives
Figure BDA0002961587500000292
Figure BDA0002961587500000301
As can be seen from the data in Table 5, the resveratrol derivative provided by the invention has certain insecticidal performance.
Although the present invention has been described in detail with reference to the above embodiments, it is only a part of the embodiments of the present invention, not all of the embodiments, and other embodiments can be obtained without inventive step according to the embodiments, and the embodiments are within the scope of the present invention.

Claims (12)

1. A resveratrol derivative has a structural formula shown as formula I or formula II:
Figure FDA0002961587490000011
wherein R is1And R2Is heterocyclic radical, substituted heterocyclic radical, aryl, substituted aryl, branched chain alkyl or cycloalkyl.
2. The resveratrol derivative according to claim 1, wherein R is1Included
Figure FDA0002961587490000012
3. The resveratrol derivative according to claim 1, wherein R is1Included
Figure FDA0002961587490000013
Figure FDA0002961587490000014
R' comprises H3CO-、F-、Cl-、Br-、O2N-、CH3-、(CH3)3C-or F3CO-。
4. The resveratrol derivative according to claim 1, wherein R is1Including CH3-CH2-、CH3-CH2-CH2-or
Figure FDA0002961587490000015
5. The resveratrol derivative according to claim 1, wherein R is2Included
Figure FDA0002961587490000016
Figure FDA0002961587490000017
6. The resveratrol derivative according to claim 1, wherein R is2Included
Figure FDA0002961587490000018
Figure FDA0002961587490000019
R' includes F-, Cl-, Br-, O2N-、CH3-or (CH)3)3C-。
7. The resveratrol derivative according to claim 1, wherein R is2Including CH3-CH2-、CH2＝CH-、
Figure FDA00029615874900000110
8. The method for preparing resveratrol derivative according to any one of claims 1-7, comprising the steps of:
mixing resveratrol, dichloromethane, triethylamine and an acyl chloride-based compound, and carrying out esterification reaction to obtain the resveratrol derivative, wherein the acyl chloride-based compound comprises acyl chloride or sulfonyl chloride, when the acyl chloride-based compound is sulfonyl chloride, the resveratrol derivative with the structure shown in the formula I is obtained, and when the acyl chloride-based compound is acyl chloride, the resveratrol derivative with the structure shown in the formula II is obtained;
the acyl chloride comprises heterocyclic group substituted acyl chloride, substituted heterocyclic group substituted acyl chloride, aryl substituted acyl chloride, substituted aryl substituted acyl chloride, branched chain alkyl substituted acyl chloride or cycloalkyl substituted acyl chloride;
the sulfonyl chloride comprises heterocycle substituted sulfonyl chloride, substituted heterocycle substituted sulfonyl chloride, aryl substituted sulfonyl chloride, substituted aryl substituted sulfonyl chloride, branched chain alkyl substituted sulfonyl chloride or cycloalkyl substituted sulfonyl chloride.
9. The use of the resveratrol derivative according to any one of claims 1-7 or the resveratrol derivative prepared by the preparation method according to claim 8 in the control of plant diseases and insect pests.
10. Use according to claim 9, when R is1Is composed of
Figure FDA0002961587490000021
CH3-CH2-or
Figure FDA0002961587490000022
The application is the application of the resveratrol derivative with the structure shown in the formula I in inhibiting tobacco mosaic virus;
when R is2Is composed of
Figure FDA0002961587490000023
CH2＝CH-、CH3-CH2-、
Figure FDA0002961587490000024
The application is the application of the resveratrol derivative with the structure shown in the formula II in inhibiting tobacco mosaic virus.
11. Use according to claim 9, when R is1Is composed of
Figure FDA0002961587490000025
CH3-CH2-CH2-or
Figure FDA0002961587490000026
The application is the application of the resveratrol derivative with the structure shown in the formula I in plant disinsection;
when R is2Is composed of
Figure FDA0002961587490000031
CH3-CH2-、CH2＝CH-、
Figure FDA0002961587490000032
The application is the application of the resveratrol derivative with the structure shown in the formula II in plant disinsection.
12. Use according to claim 9, characterized in that it is a use in plant antisepsis.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1445216A (en) * 2003-03-03 2003-10-01 中国科学院广州化学研究所 Nicotinic acid ester of resveratrol and its synthetic method
CN102126993A (en) * 2010-12-09 2011-07-20 南昌大学 Resveratrol derivative and application thereof to preparation of antitumor medicaments
CN105126116A (en) * 2015-09-21 2015-12-09 中国科学院长春应用化学研究所 Resveratrol nano-particles and preparation method thereof
CN109422744A (en) * 2017-08-21 2019-03-05 南开大学 Matrine derivative and its synthesis and the application in terms of preventing and treating plant pest

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1445216A (en) * 2003-03-03 2003-10-01 中国科学院广州化学研究所 Nicotinic acid ester of resveratrol and its synthetic method
CN102126993A (en) * 2010-12-09 2011-07-20 南昌大学 Resveratrol derivative and application thereof to preparation of antitumor medicaments
CN105126116A (en) * 2015-09-21 2015-12-09 中国科学院长春应用化学研究所 Resveratrol nano-particles and preparation method thereof
CN109422744A (en) * 2017-08-21 2019-03-05 南开大学 Matrine derivative and its synthesis and the application in terms of preventing and treating plant pest

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DU CHENG ET AL.: "Design, synthesis and antibreast cancer MCF-7 cells biological evaluation of heterocyclic analogs of resveratrol", 《JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH》 *
H. J. YANG ET AL.,: "Synthesis and Anticoagulant Bioactivity of Heterocyclic Derivatives of Resveratrol", 《CHEMISTRY OF NATURAL COMPOUNDS》 *
URBANIAK ALICJA ET AL: "Microwave-Assisted Synthesis of Aromatic and Aliphatic Triesters of Resveratrol", 《SYNTHESIS 》 *

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