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

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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).