• 百种中国杰出学术期刊
  • 中国精品科技期刊
  • 中国高校百佳科技期刊
  • 中国高校精品科技期刊
  • 中国国际影响力优秀学术期刊
  • 中国科技核心期刊

留言板

尊敬的读者、作者、审稿人, 关于本刊的投稿、审稿、编辑和出版的任何问题, 您可以本页添加留言。我们将尽快给您答复。谢谢您的支持!

姓名
邮箱
手机号码
标题
留言内容
验证码

天然杀线虫先导化合物Waltherione A类似物的合成及杀线虫活性

张羲 谢世爽 胡展 张北京 刘启凤 丁晓帆 谢佳 邵雨 孙然锋

张羲, 谢世爽, 胡展, 张北京, 刘启凤, 丁晓帆, 谢佳, 邵雨, 孙然锋. 天然杀线虫先导化合物Waltherione A类似物的合成及杀线虫活性[J]. 农药学学报, 2022, 24(2): 272-279. doi: 10.16801/j.issn.1008-7303.2021.0150
引用本文: 张羲, 谢世爽, 胡展, 张北京, 刘启凤, 丁晓帆, 谢佳, 邵雨, 孙然锋. 天然杀线虫先导化合物Waltherione A类似物的合成及杀线虫活性[J]. 农药学学报, 2022, 24(2): 272-279. doi: 10.16801/j.issn.1008-7303.2021.0150
ZHANG Xi, XIE Shishuang, HU Zhan, ZHANG Beijing, LIU Qifeng, DING Xiaofan, XIE Jia, SHAO Yu, SUN Ranfeng. Synthesis and nematicidal activity of natural nematicidal lead compound Waltherione A analogues[J]. Chinese Journal of Pesticide Science, 2022, 24(2): 272-279. doi: 10.16801/j.issn.1008-7303.2021.0150
Citation: ZHANG Xi, XIE Shishuang, HU Zhan, ZHANG Beijing, LIU Qifeng, DING Xiaofan, XIE Jia, SHAO Yu, SUN Ranfeng. Synthesis and nematicidal activity of natural nematicidal lead compound Waltherione A analogues[J]. Chinese Journal of Pesticide Science, 2022, 24(2): 272-279. doi: 10.16801/j.issn.1008-7303.2021.0150

天然杀线虫先导化合物Waltherione A类似物的合成及杀线虫活性

doi: 10.16801/j.issn.1008-7303.2021.0150
基金项目: 国家自然科学基金 (22067004);海南省自然科学基金资助(321CXTD436, 321QN177, 321QN178);海南大学高层次人才引进启动经费 (kyqd1640);海南省烟草公司科技计划(2018003).
详细信息
    作者简介:

    张羲,20090403210004@hainanu.edu.cn

    通讯作者:

    孙然锋,srf18@hainanu.edu.cn.

  • 中图分类号: S482.51;TQ450

Synthesis and nematicidal activity of natural nematicidal lead compound Waltherione A analogues

Funds: the National Natural Science Foundation of China (22067004), Hainan Provincial Natural Science Foundation of China (321CXTD436, 321QN177, 321QN178), Startup Foundation for Introduced Talents of Hainan University (kyqd1640), Annual Science and Technology Project of Hainan Provincial Tobacco Company of CNTC (2018003).
  • 摘要: 为了找出天然杀线虫先导生物碱Waltherione A的关键药效基团并简化其结构,以2,3-二甲氧基苯甲醛和3,4-二甲氧基苯甲醛为原料,经过分子内傅克烷基化反应形成苯并七元氧桥环,并用不同的取代基与桥环相连,合成了12个Waltherione A类似物,其中8个化合物未见文献报道,所有目标化合物的结构均通过核磁共振氢谱(1H NMR)、碳谱(13C NMR)及高分辨质谱(HRMS)确证。采用浸虫法测定了目标化合物对南方根结线虫Meloidogyne incognita的杀虫活性。结果表明:目标化合物杀线虫的活性均低于Waltherione A,其中化合物 A-12 在200 μg/mL下对南方根结线虫2龄幼虫72 h的致死率为69.7%。 A-12 的杀线虫活性高于其他目标化合物,表明芳香取代基与苯并七元氧桥环相连时对化合物活性的提升存在积极作用,这为进一步的结构优化提供了方向。
  • 1  Waltherione A的结构和设计思路

    1.  Structure of Waltherione A and the design strategy

    2  目标化合物的合成路线

    2.  Synthetic routes of target compounds

    3  合成目标化合物A-5的反应机理

    3.  Reaction mechanism of synthesis of target compound A-5

    表  1  化合物A-7~A-13和B-7中R1、R2的结构

    Table  1.   The structures of R1 and R2 in compounds A-7-A-13 and B-7

    化合物
    Compound
    R1R2
    A-7 3,4-(OCH3)2
    B-7 2,3-(OCH3)2
    A-8 3,4-(OCH3)2
    A-9 3,4-(OCH3)2
    A-10 3,4-(OCH3)2
    A-11 3,4-(OCH3)2
    A-12 3,4-(OCH3)2
    A-13 3,4-(OCH3)2
    下载: 导出CSV

    表  2  目标化合物对南方根结线虫的致死活性 (校正死亡率/%)

    Table  2.   Nematicidal activity of the target compounds against Meloidogyne incongnita (Adjusted mortality/%)

    化合物
    Compound
    200 μg/mL 100 μg/mL 50 μg/mL
    24 h48 h72 h 24 h48 h72 h 24 h48 h72 h
    A-5 9.9±0.7 13.8±1.4 14.9±1.1 2.3±0.1 4.3±0.2 4.9±0.6
    A-6 8.3±0.2 12.3±1.5 13.2±0.8 3.4±0.8 4.5±1.1 5.7±0.8
    A-7 12.3±0.4 19.6±0.2 25.3±0.1 5.7±0.3 7.8±0.1 9.3±0.7
    A-8 12.5±0.1 22.6±0.4 28.3±0.2 3.1±0.2 5.8±0.1 9.9±0.8
    A-9 11.7±0.1 18.9±0.6 26.8±0.5 5.2±0.5 6.4±0.1 8.8±0.4
    A-10 11.6±0.2 16.8±0.5 27.1±0.1 2.2±0.6 4.3±0.1 7.8±0.1
    A-11 6.4±0.1 14.2±0.4 19.0±0.2 1.8±0.6 3.6±0.1 6.7±0.6
    A-12 47.8±0.3 64.1±0.5 69.7±1.3 9.0±0.2 17.2±0.1 27.3±0.2 2.2±0.2 11.9±0.5 16.8±0.7
    A-13 9.9±0.2 12.4±0.9 20.0±0.7 2.0±0.9 4.3±0.1 7.0±0.3
    B-5 7.6±0.2 14.7±0.1 15.5±0.1 3.5±0.8 4.7±0.1 5.2±0.6
    B-6 8.1±0.1 13.1±0.3 14.6±0.1 2.4±0.6 3.8±0.1 4.4±0.7
    B-7 10.5±0.6 20.6±0.2 26.3±1.3 4.7±0.1 6.1±0.1 9.4±0.9
    Waltherione A 97.1±1.7 100.0±0.0 100.0±0.0
    阿维菌素 abamectin 100.0±0.0 100.0±0.0 100.0±0.0
    注:“—” 未测试。Note: ' — ' not tested.
    下载: 导出CSV
  • [1] CHEN J X, LI Q X, SONG B A. Chemical nematicides: recent research progress and outlook[J]. J Agric Food Chem, 2020, 68(44): 12175-12188. doi: 10.1021/acs.jafc.0c02871
    [2] HOELZEL S C, VIEIRA E R, GIACOMELLI S R, et al. An unusual quinolinone alkaloid from Waltheria douradinha[J]. Phytochemistry, 2005, 66(10): 1163-1167. doi: 10.1016/j.phytochem.2005.03.019
    [3] DIAS G C, GRESSLER V, HOENZEL S C, et al. Constituents of the roots of Melochia chamaedrys[J]. Phytochemistry, 2007, 68(5): 668-672. doi: 10.1016/j.phytochem.2006.11.004
    [4] GRESSLER V, STÜKER C Z, DIAS G de O C, et al. Quinolone alkaloids from Waltheria douradinha[J]. Phytochemistry, 2008, 69(4): 994-999. doi: 10.1016/j.phytochem.2007.10.018
    [5] JADULCO R C, POND C D, Van WAGONER R M, et al. 4-Quinolone alkaloids from Melochia odorata[J]. J Nat Prod, 2014, 77(1): 183-187. doi: 10.1021/np400847t
    [6] RAHIM A, SAITO Y, FUKUYOSHI S, et al. Paliasanines A-E, 3, 4-methylenedioxyquinoline alkaloids fused with a phenyl-14-oxabicyclo[3.2.1]octane unit from Melochia umbellata var. deglabrata[J]. J Nat Prod, 2020, 83(10): 2931-2939. doi: 10.1021/acs.jnatprod.0c00454
    [7] JANG J Y, LE DANG Q, CHOI G J, et al. Control of root-knot nematodes using Waltheria indica producing 4-quinolone alkaloids[J]. Pest Manag Sci, 2019, 75(8): 2264-2270.
    [8] KIM J, SEO S M, LEE S G, et al. Nematicidal activity of plant essential oils and components from coriander (Coriandrum sativum), oriental sweetgum (Liquidambar orientalis), and valerian (Valeriana wallichii) essential oils against pine wood nematode (Bursaphelenchus xylophilus)[J]. J Agric Food Chem, 2008, 56(16): 7316-7320. doi: 10.1021/jf800780f
    [9] LEWIS A R, REBER K P. Synthesis of antifungal alatanone and trineurone polyketides[J]. Tetrahedron Lett, 2016: 1083-1086.
    [10] TRIANDAFILLIDI I, RAFTOPOULOU M, SAVVIDOU A, et al. Organocatalytic synthesis of lactones by the oxidation of alkenoic acids[J]. ChemCatChem, 2017, 9(21): 4120-4124. doi: 10.1002/cctc.201700837
    [11] Van HORN J D, BURROWS C J. Formation oftrans-3-hydroxy-4-phenylbutyrolactone from trans-styrylacetic acid and aqueous KHSO5[J]. Tetrahedron Lett, 1999, 40(11): 2069-2070. doi: 10.1016/S0040-4039(99)00167-7
    [12] ALBURY A M M, De JOARDER D, JENNINGS M P. Synthesis of (±)-tetramethoxy-sinensigenin A via an intramolecular Marson-type cyclization[J]. Tetrahedron Lett, 2015, 56(23): 3057-3059. doi: 10.1016/j.tetlet.2014.11.030
    [13] CHEN S Y, DICKSON D W. A technique for determining live second-stage juveniles of Heterodera glycines[J]. J Nematol, 2000, 32(1): 117-121.
  • 天然杀线虫先导化合物 Waltherione A 类似物的合成_目标化合物核磁谱图.pdf
  • 加载中
图(3) / 表(2)
计量
  • 文章访问数:  285
  • HTML全文浏览量:  39
  • PDF下载量:  71
  • 被引次数: 0
出版历程
  • 收稿日期:  2021-06-21
  • 录用日期:  2021-09-17
  • 网络出版日期:  2021-10-19
  • 刊出日期:  2022-04-01

目录

    /

    返回文章
    返回