Synthesis and cytotoxic activities of 8- and 6-demethyleucalyptins
Synthesis and cytotoxic activities of 8- and 6-demethyleucalyptins
复制标题
8-和6-去甲基桉树素的合成和细胞毒活性
DOI：
10.1093/bbb/zbac105
复制
发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Kuramochi Kouji
中科院分区：
文献类型：
--
作者：
Asakawa Ryuki;Fuchiyama Kanta;Ishii Yunosuke;Hosaka Keisuke;Kobayashi Atsushi;Shimazaki Kei;Nagasawa Junki;Tsuchida Sayaka;Ushida Kazunari;Matsubayashi Makoto;Furuyama Yuuki;Ohgane Kenji;Kuramochi Kouji
植物中的次级代谢产物影响食草动物的健康，例如以高山植物的叶子和果实为食的日本岩雷鸟。因此，了解高山植物次生代谢产物及其生物活性对保护日本岩雷鸟具有重要意义。我们从日本松鸡的主要食物--平卧卡蜜亚（Kalmia procumbens）的叶子中分离出C-甲基黄酮。通过核磁共振（NMR）数据与文献报道的结果进行比较，推测其结构为8-去甲基甘草素，但不能排除分离得到的化合物为6-去甲基甘草素的可能性。因此，合成了两种异构体。通过与合成化合物的NMR数据比较，明确地确定分离的化合物为8-去甲基丁香苷。8-和6-去甲基丁香素的细胞毒性评价显示，只有前者显示对HCT 116和MRC-5细胞的细胞毒性。本研究不仅提供了容易获得的8-和6-去甲基丁香素，而且还提供了它们的生物信息。
Secondary metabolites in plants influence the health of herbivores such as Japanese rock ptarmigans that feed on the leaves and fruits of alpine plants. Thus, it is important to understand the secondary metabolites of alpine plants and their biological activities for conserving Japanese rock ptarmigans. We isolatedC-methylflavone from the leaves ofKalmia procumbens, on which Japanese rock ptarmigans feed. Although its structure was deduced to be 8-demethyleucalyptin by comparing its nuclear magnetic resonance (NMR) data with the reported ones, the possibility that the isolated compound is 6-demethyleucalyptin cannot be ruled out. Thus, both isomers were synthesized. The isolated compound was unambiguously determined to be 8-demethyleucalyptin by comparing its NMR data with those of the synthetic ones. Cytotoxic evaluation of 8- and 6-demethyleucalyptins revealed that only the former showed cytotoxicity against HCT116 and MRC-5 cells. The present study provides not only easy access to 8- and 6-demethyleucalyptins, but also their biological information.