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Development of the Environmentally Benign Agrichemicals and Novel Drug Seeds Based on Natural Allelochemicals

基于天然化感物质的环保农药及新药种子的开发

基本信息

批准号：
16209001
负责人：
SHISHIDO Kozo
金额：
$ 30.37万
依托单位：
The University of Tokushima
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (A)
财政年份：
2004
资助国家：
日本
起止时间：
2004 至 2006
项目状态：
已结题

项目摘要

1. Syntheteic studies on the allelochemicals isolated from sunflower (Helianthus annuus L. var. SH-222) were performed and the following results were obtained.(1) Enantiocontrolled total syntheses of the nine natural heliannuol sesquiterpenoids were completed and the absolute structures were established.(2) The first and enantioselective total syntheses of heliespirones A and C were accomplished by a Lewis acid-mediated carbon-carbon bond forming reaction as a key reaction step, which is a novel transformation.(3) The first and enantioselective total synthesis of sundiversifolide, which has been isolated from sunflower, was accomplished. The synthetic route developed here is convenient and a problem of the supply was solved.(4) Enantiocontrolled total syntheses of breviones A, B and C, which have been isolated from Penicillium brevicompactum Dierckx, were completed. For brevione C, this is the first synthesis and the absolute structure was established.2. Biological evaluations were investigated for the synthesized compounds including natural products.(1) Allelopathic activites for the natural and unnatural compounds synthesized were evaluated using two plants lettuce and timothy. Of these, (+)-and (-)-heliannuol A and (-)-heliannuol C showed strong activity. The compound with the strongest activity was 2-methyl-3-phenylcinnamic acid.(2) Regarding pharmacological activities, (+)-heliannuol D showed a strong NF-kB inhibitory activity. It also should be noted that (+)-brevione A exhibited a strong cytotoxic activity for HCT-116 cell (human colon tumor cell).

1.向日葵化感物质的合成研究变种SH-222），并获得以下结果。(1)完成了9个天然向日葵酚类倍半萜的对映体控制全合成，并确定了其绝对结构。(2)通过刘易斯酸介导的碳-碳键形成反应作为关键反应步骤，首次实现了螺环酮A和C的对映选择性全合成。(3)首次完成了从向日葵中分离得到的向日葵花内酯的对映选择性全合成。该合成路线简便易行，解决了原料供应问题。(4)对从短密青霉（Penicillium brevicompactum Dierckx）中分离得到的短环酮A、B和C进行了对映体控制全合成。对于短叶芹酮C，这是首次合成，并确定了其绝对结构.对合成的化合物包括天然产物进行了生物学评价。(1)以莴苣和梯牧草为试材，研究了合成的天然和非天然化合物的化感活性。其中，（+）-和（-）-向日葵酚A和（-）-向日葵酚C表现出强活性。活性最强的化合物是2-甲基-3-苯基肉桂酸。(2)关于药理活性，（+）-向日葵酚D显示出强的NF-κ B抑制活性。还应该注意的是，（+）-灯盏花素A对HCT-116细胞（人结肠肿瘤细胞）表现出强的细胞毒活性。