冯俊涛, 张亚梅, 王俊儒, 张兴. 天名精内酯酮衍生物合成及其抑菌活性[J]. 农药学学报, 2007, 9(2): 185-188.
    引用本文: 冯俊涛, 张亚梅, 王俊儒, 张兴. 天名精内酯酮衍生物合成及其抑菌活性[J]. 农药学学报, 2007, 9(2): 185-188.
    shu
    FENG Jun-tao, ZHANG Ya-mei, WANG Jun-ru, ZHANG Xing. Synthesis and Antifugal Activities of Carabrone Derivatives[J]. Chinese Journal of Pesticide Science, 2007, 9(2): 185-188.
    Citation: FENG Jun-tao, ZHANG Ya-mei, WANG Jun-ru, ZHANG Xing. Synthesis and Antifugal Activities of Carabrone Derivatives[J]. Chinese Journal of Pesticide Science, 2007, 9(2): 185-188.
    shu

    天名精内酯酮衍生物合成及其抑菌活性

    Synthesis and Antifugal Activities of Carabrone Derivatives

      摘要
    • 摘要: 根据天名精内酯酮的分子结构特点,用NaBH4/MeOH 选择性还原羰基得到天名精内酯醇和13-甲氧基天名精内酯醇,以MeOH/Mg还原双键得化合物11,13-双氢天名精内酯酮,以NaBH4/I2还原羰基得到卡拉布烷-3(4)-烯-12,8β-内酯,所有还原产物的结构经MS、1H NMR确认。采用悬滴法测定了合成衍生物对黄瓜炭疽病菌孢子萌发的抑制作用,结果表明:天名精内酯酮及其衍生物天名精内酯醇、13-甲氧基天名精内酯醇、11,13-双氢天名精内酯酮、卡拉布烷-3(4)-烯-12,8β-内酯的EC50值依次为7.18、21.67、26.47、40.32和42.67 mg/L。结果初步表明11,13双键和4位羰基均为天名精内酯酮的主要抑菌活性基团,且前者对抑菌活性的影响更明显。

       

      Abstract: Based on the characteristic of carabrone molecule structure,carabrol and 13-methoxycarabrol were obtained by the selective reduction of the saturated carbonyl group with NaBH4/MeOH.11,13-Dihydrocarabrone was synthesized by the selective reduction with MeOH/Mg,and carabran-3(4)-en-12,8β-olide was obtained with NaBH4/I2.The chemical structures of four derivatives were comfirmed by 1H NMR and MS.Their biological activities were assayed with the hanging drop method.The tested compounds showed inhibition effects against the spores germination of Colletotrichum lagenarium.The EC50 values of carabrone and the four derivatives were 7.18,21.67,26.47,40.32 and 42.67 mg/L,respectively.Its proposed that both 11,13-double bond of carabrone and the 4-saturated carbonyl group are the active sites,and the former group had a stronger inhibition effect.

       

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