Plant Protection Oriented Synthetic Studies on Bioactive Terpenoids

面向植物保护的生物活性萜类化合物的合成研究

• 批准号: 16580088
• 负责人: TAKIKAWA Hirosato
• 金额: $ 2.05万
• 依托单位: Kobe University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2004
• 资助国家: 日本
• 起止时间: 2004 至 2005
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/en/grant/KAKENHI-PROJECT-16580088/
• 关键词: plant protection; terpenoid; allelopathy; total synthesis; 光学分割; 絶対立体配置

In this research, syntheses of bioactive natural terpenoids have been studied. The practical synthetic targets are breviones, annuionones and sundiversifolide. Breviones are allelopathic diterpenoids isolated from Penicillium sp. Annuionones and sundiversifolide are also allelopathic agents isolated from sunflower. These allelopathic terpenoids may have the agricultural potential as environmentally benign herbicides. Thus, the main objective of this research is not only "total synthesis" but also contribution for "plant protection".The representative achievements of this work are as follows :1.The first synthesis of both enantiomers of brevione B was accomplished. The absolute configuration of naturally occurring brevione B was therefore determined.2.The first synthesis of both enantiomers of annuionone A was accomplished. The absolute configuration of naturally occurring annuionone A was therefore determined.3.The formal synthesis of sundiversifolide was achieved by employing Claisen rearrangement as the key step.The detailed bioassay of synthesized samples including synthetic intermediates is now in preparation.

在本研究中，研究了具有生物活性的天然萜类化合物的合成。实用的合成目标是短草酮类、年青酮类和sundiversifolide。 Breviones 是从青霉属 sp 中分离出来的化感作用二萜类化合物。 Annuionones 和 sundiversifolide 也是从向日葵中分离出的化感药剂。这些化感萜类化合物可能具有作为环境友好型除草剂的农业潜力。因此，本研究的主要目的不仅是“全合成”，更是为“植物保护”做出贡献。本工作的代表性成果如下： 1.首次合成了短波维酮B的两种对映体。由此确定了天然存在的短短草酮B的绝对构型。2.完成了年青酮A两种对映体的首次合成。由此确定了天然存在的annuionone A的绝对构型。3.以Claisen重排为关键步骤，实现了sundiversifolide的正式合成。包括合成中间体在内的合成样品的详细生物测定工作正在准备中。

项目成果

Synthetic studies on natural products having useful bioactivity and unique structure

具有有用生物活性和独特结构的天然产物的合成研究

• 发表时间: 2004
• 期刊: Nippon Nogeikagaku Kaishi 78-10
• 作者: A.Shimada;H.Yamane;Y.Kimura;Tomomi Imamura;Tomomi Imamura;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;Hirosato Takikawa;Hirosato Takikawa;滝川浩郷;Hirosato Takikawa;Hirosato Takikawa;Hirosato Takikawa;Hirosato Takikawa;Hirosato Takikawa;Hirosato Takikawa;Hirosato Takikawa;滝川 浩郷;Hirosato Takikawa
• 通讯作者: Hirosato Takikawa

有用な生物活性および特異な構造を有する天然有機化合物の合成研究

具有有用生物活性和独特结构的天然有机化合物的合成研究

• 发表时间: 2004
• 期刊: 日本農芸化学会誌 78巻・10号
• 作者: A.Shimada;H.Yamane;Y.Kimura;Tomomi Imamura;Tomomi Imamura;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;Hirosato Takikawa;Hirosato Takikawa;滝川浩郷;Hirosato Takikawa;Hirosato Takikawa;Hirosato Takikawa;Hirosato Takikawa;Hirosato Takikawa;Hirosato Takikawa;Hirosato Takikawa;滝川 浩郷;Hirosato Takikawa;滝川 浩郷
• 通讯作者: 滝川 浩郷

Synthetic studies on allelopathic terpenoids

化感萜类化合物的合成研究

• 发表时间: 2006
• 期刊: Journal of Synthetic Organic Chemistry, Japan (Yuki Gosei, Kagaku Kyokaishi) 64(in press)
• 作者: A.Shimada;H.Yamane;Y.Kimura;Tomomi Imamura;Tomomi Imamura;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;Hirosato Takikawa;Hirosato Takikawa;滝川浩郷;Hirosato Takikawa;Hirosato Takikawa;Hirosato Takikawa
• 通讯作者: Hirosato Takikawa

Synthesis and absolute configuratin of bevione B, an allelochemical isolated from Penicillium sp.

Bevione B 的合成和绝对配置，bevione B 是一种从青霉菌中分离出来的化感物质。

• 发表时间: 2006
• 期刊: Tetrahedron 62巻・1号
• 作者: A.Shimada;H.Yamane;Y.Kimura;Tomomi Imamura;Tomomi Imamura;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;Hirosato Takikawa
• 通讯作者: Hirosato Takikawa

Synthetic studies on breviones and structurally related natural products

短草酮及结构相关天然产物的合成研究

• 发表时间: 2006
• 期刊: Biosci. Biotechnol. Biochem 70(印刷中)
• 作者: A.Shimada;H.Yamane;Y.Kimura;Tomomi Imamura;Tomomi Imamura;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;N.Takahashi;Hirosato Takikawa;Hirosato Takikawa
• 通讯作者: Hirosato Takikawa