Tetrahedron Letters ( IF 1.5 ) Pub Date : 2020-03-23 , DOI: 10.1016/j.tetlet.2020.151861 Masaki Yamashita , Yohei Saito , Abdul Rahim , Shuichi Fukuyoshi , Katsunori Miyake , Masuo Goto , Kyoko Nakagawa-Goto
Two new furanoquinolones, 3-oxolunacrine (1) and 2,3-dehydrolunacrine (2), and 22 known quinolones (3–24) were isolated from the methanol extract of the bark of Lunasia amara. The chemical structures of the newly isolated compounds were elucidated from HRMS and various NMR spectroscopic data. Pure (S)- and (R)-isomers of 1, which was obtained as a racemate, were separated by chiral column chromatography. The possibility that racemic 1 occurs naturally was discussed based on a proposed biosynthetic pathway. Selected isolated quinoline alkaloids were evaluated for antiproliferative activities against five human tumor cell lines, including a multidrug-resistant cell line overexpressing p-glycoprotein.
中文翻译:
来自印尼植物Lunasia amara的新型呋喃喹啉酮
从Lunasia amara树皮的甲醇提取物中分离出了两个新的呋喃喹诺酮,3-氧氟尿酸(1)和2,3-脱氢氟纳林(2),以及22种已知的喹诺酮(3-24)。从HRMS和各种NMR光谱数据阐明了新分离出的化合物的化学结构。通过手性柱色谱分离得到作为外消旋物的1的纯(S)-和(R)-异构体。外消旋1的可能性基于提议的生物合成途径讨论了自然发生的情况。评价选择的分离的喹啉生物碱对五种人类肿瘤细胞系的抗增殖活性,包括一种过度表达p-糖蛋白的多药耐药细胞系。