Synthetic Studies on Novel, Natural Anti-Mitotic Agents, Nigricanosides, toward Elucidation of Their Stereochemistry and Biological Activity

新型天然抗有丝分裂剂黑芥苷的合成研究，以阐明其立体化学和生物活性

• 批准号: 21510218
• 负责人: FUJIWARA Kenshu
• 金额: $ 3万
• 依托单位: Hokkaido University
• 依托单位国家: 日本
• 项目类别: Grant-in-Aid for Scientific Research (C)
• 财政年份: 2009
• 资助国家: 日本
• 起止时间: 2009 至 2011
• 项目状态: 已结题
• 来源: https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-21510218/
• 关键词: 生物活性分子の設計; 合成; グリセロ糖脂質; 立体構造解明; ニグリカノシAジメチルエステル; 立体選択的合成; 全合成; エーテル結合性脂質; 酸化脂質; 有糸分裂阻害剤; ニグリカノシドAジメチルエステル; 有糸分裂阻害物質

Nigricanoseides, isolated from the green alga Avrainvillea nigricans, belong to a monogalactosyldiacylglycerol family and exhibit potent growth inhibitory activity against cancer cells. Because of the scarce supply from natural source and the unknown stereochemistry, nigricanosides are not explored biologically in detail. Therefore, studies aiming at the elucidation of their stereochemistry and biological activity have commenced with the partial synthesis of a congener, nigricanoseide A dimethyl ester. As a result, methods for the construction of the two ether linkages have been established, and the stereochemistry of the ether junction between the galactose moiety and the lower acyl chain has been clarified.

从绿色植物Avrainvilleanigricans中分离得到的黑曲霉糖甙属于单半乳糖基甘油二酯家族，对癌细胞具有较强的生长抑制活性。由于天然来源的稀缺性和未知的立体化学，黑果苷没有详细的生物学研究。因此，旨在阐明其立体化学和生物活性的研究已经开始与同系物，黑苷A二甲酯的部分合成。因此，已经建立了用于构建两个醚键的方法，并且已经澄清了半乳糖部分和低级酰基链之间的醚连接的立体化学。

项目成果

Synthetic Studies on Nigricanoside A Dimethyl Ester (2) : An Approach to Construct the Ether Linkage between the Lipid Chains

黑果苷A二甲酯的合成研究(2)：脂质链间醚键的构建方法

• 发表时间: 2010
• 作者: Kenshu Fujiwara;Ayako Kawai;Naoto Kinashi;Hidetoshi Kawai;and Takanori Suzuki
• 通讯作者: and Takanori Suzuki

Improved synthesis of C8-C20 segmentof pectenotoxin-2.

改进果胶毒素-2 C8-C20 片段的合成。

• DOI: 10.1016/j.tetlet.2011.08.051
• 发表时间: 2011
• 期刊: Tetrahedron Lett
• 影响因子: 1.8
• 作者: Kenshu Fujiwara;Yuki Suzuki;Nao Koseki;Shun-ichi Murata;Akio Murai;Hidetoshi Kawai;and Takanori Suzuki
• 通讯作者: and Takanori Suzuki

Model studies for the stereoselective construction of the BC-ring of armatol F based on Ireland-Claisen rearrangement and relay ring-closing olefin metathesis

• DOI: 10.1016/j.tetlet.2010.06.103
• 发表时间: 2010-08-25
• 期刊: TETRAHEDRON LETTERS
• 影响因子: 1.8
• 作者: Fujiwara, Kenshu;Tanaka, Keita;Suzuki, Takanori
• 通讯作者: Suzuki, Takanori

Studies toward the total synthesis of armatol F: stereoselective construction of the C6 and C7 stereocenters and formation of the A-ring skeleton

• DOI: 10.1016/j.tetlet.2010.06.026
• 发表时间: 2010-08-11
• 期刊: TETRAHEDRON LETTERS
• 影响因子: 1.8
• 作者: Fujiwara, Kenshu;Hirose, Yuta;Suzuki, Takanori
• 通讯作者: Suzuki, Takanori

ニグリカノシドAジメチルエステルの合成研究

黑胡椒苷A二甲酯的合成研究

• 发表时间: 2011
• 作者: 木梨尚人;藤原憲秀;河合英敏;鈴木孝紀
• 通讯作者: 鈴木孝紀