刘存芳. 丹皮酚衍生物——3-羟基-1-(2-羟基-4-甲氧基苯)-3-(2'-溴苯)-1-丙酮的合成及其抗菌活性[J]. 农药学学报, 2016, 18(1): 119-123. DOI: 10.16801/j.issn.1008-7303.2016.0015
    引用本文: 刘存芳. 丹皮酚衍生物——3-羟基-1-(2-羟基-4-甲氧基苯)-3-(2'-溴苯)-1-丙酮的合成及其抗菌活性[J]. 农药学学报, 2016, 18(1): 119-123. DOI: 10.16801/j.issn.1008-7303.2016.0015
    LIU Cunfang. Synthesis and antimicrobial activity of a paeonol derivative: 3-hydroxy-1-(2-hydroxy-4-methoxyphenyl)-3-(2'-bromophenyl)-1-acetone[J]. Chinese Journal of Pesticide Science, 2016, 18(1): 119-123. DOI: 10.16801/j.issn.1008-7303.2016.0015
    Citation: LIU Cunfang. Synthesis and antimicrobial activity of a paeonol derivative: 3-hydroxy-1-(2-hydroxy-4-methoxyphenyl)-3-(2'-bromophenyl)-1-acetone[J]. Chinese Journal of Pesticide Science, 2016, 18(1): 119-123. DOI: 10.16801/j.issn.1008-7303.2016.0015

    丹皮酚衍生物——3-羟基-1-(2-羟基-4-甲氧基苯)-3-(2'-溴苯)-1-丙酮的合成及其抗菌活性

    Synthesis and antimicrobial activity of a paeonol derivative: 3-hydroxy-1-(2-hydroxy-4-methoxyphenyl)-3-(2'-bromophenyl)-1-acetone

    • 摘要: 从牡丹根皮中提取丹皮酚,将丹皮酚精制后与2-溴苯甲醛在室温及碱催化下发生亲核加成反应,生成一种丹皮酚衍生物——3-羟基-1-(2-羟基-4-甲氧基苯)-3-(2'-溴苯)-1-丙酮,产率为78.6%,其结构用紫外光谱(UV)、红外光谱(IR)、质谱(MS)及核磁共振谱(NMR),结合元素分析等进行表征。单晶X-衍射(X-ray diffraction)测定结果表明:该晶体属单斜晶系;P2(1)/n空间群;晶胞参数:a=0.99380(15) nm,b=0.80617(12) nm,c=1.9251(3) nm,α=90.0(2)°,β=103.287(2)°,γ=90(2)°,V=1.5010(4) nm3,Dc=1.554 mg/cm3, μ=2.751 mm-1,F(000)=712,Z=4,R1=0.0290,ωR2=0.0660,R(int)=0.0322。该丹皮酚衍生物具有抗菌活性,对植物源真菌油菜菌核病菌Sclerotinia sclerotiorum和番茄灰霉病菌Botrytis cinerea的最小抑菌浓度(MIC)分别为0.36和0.48 g/L,对病源细菌福氏志贺菌Shigella flexneri 51065和金黄色葡萄球菌Staphylococcus aureus ATTCC25925的MIC分别为0.02和0.06 g/L。

       

      Abstract: Paeonol was isolated from the root of Paeonia Suffruicosa. A derivative of paeonol, 3-hydroxy-1-(2-hydroxy-4-methoxyphenyl)-3-(2'-bromophenyl)-1-acetone, was synthesized by nucleophilic addition of paeonol with 2-bromobenzaldehyde at room temperature in a yield of 78.6%. The structure of this compound was identified by UV, IR, MS, NMR and elemental analyses and was confirmed by X-ray analysis. It belongs to monoclinic crystallographic system with space group P2(1)/n and a=0.993 80(15) nm, b=0.806 17(12) nm, c=1.925 1(3) nm, α=90.0(2)°, β=103.287(2)°, γ=90(2)°, V=1.501 0(4) nm3, Dc=1.554 mg/m3, μ=2.751 mm-1, F(000)=712, Z=4, R1=0.029 0, ωR2=0.066 0, R(int)=0.032 2. The minimum inhibitory concentration (MIC) of this compound against plant pathogenic fungi of Sclerotinia sclerotiorum and Botrytis cinerea were 0.36 and 0.48 g/L, and MIC value against Shigella flexneri 51065 and Staphylococcus aureus ATCC25925 were 0.02 and 0.06 g/L, respectively.

       

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