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

黑油苷是一种从黑油绿藻中分离出来的单半乳糖二酰基甘油类化合物，具有抑制癌细胞生长的活性。由于天然来源的稀缺和未知的立体化学，黑子皂苷尚未在生物学上进行详细的探索。因此，旨在阐明其立体化学和生物活性的研究已经开始部分合成其同系物，黑油苷a二甲酯。结果，建立了两个醚键的构造方法，并澄清了半乳糖部分与下酰基链之间的醚连接的立体化学性质。

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.