| Project/Area Number |
16209001
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| Research Category |
Grant-in-Aid for Scientific Research (A)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | The University of Tokushima |
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Principal Investigator |
SHISHIDO Kozo The University of Tokushima, Institute of Health Biosciences, Professor, 大学院ヘルスバイオサイエンス研究部, 教授 (20006349)
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| Co-Investigator(Kenkyū-buntansha) |
SHINDO Mitsuru Kyusyu University, Institute for Materials Chemistry and Engineering, Associate Professor, 先導化学物質研究所, 助教授 (40226345)
FUJII Yoshiharu National Institute for Agro-Environmental Sciences, Research Leader, 生物環境安全部, 研究リーダー (10354101)
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| Project Period (FY) |
2004 – 2006
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| Project Status |
Completed (Fiscal Year 2006)
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| Budget Amount *help |
¥47,450,000 (Direct Cost: ¥36,500,000、Indirect Cost: ¥10,950,000)
Fiscal Year 2006: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2005: ¥9,490,000 (Direct Cost: ¥7,300,000、Indirect Cost: ¥2,190,000)
Fiscal Year 2004: ¥33,150,000 (Direct Cost: ¥25,500,000、Indirect Cost: ¥7,650,000)
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| Keywords | agrichemical / allolochemical / drug seeds / total synthesis / heliannuols / sundiversifolide / breviones / NF-kB inhibitor / アレロケミマル / ヘリビサボノール / ヘリスピロン / サンディバーホリド / セスキテルペン / エナンチオ選択的合成 / 植物生育阻害活性 / 細胞毒性 / 大腸癌 / 核内転写因子 / 糖尿病 |
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| Research Abstract |
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).
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