Bioorganic Chemistry ( IF 5.1 ) Pub Date : 2018-09-04 , DOI: 10.1016/j.bioorg.2018.08.034 Si-Bei Wang , Dong-Rong Zhu , Biao Nie , Jing Li , Ying-Jun Zhang , Ling-Yi Kong , Jian-Guang Luo
Ten new withanolides (1–10) and three artificial withanolides (11–13) were isolated from the aerial parts of Tubocapsicum anomalum, together with five known analogues (14–18). Their structures were determined on the basis of extensive spectroscopic and chemical methods. They include seven acnistin–type (1–4, 11, 14 and 15), three withajardin–type (5–7), and eight normal–type (8–10, 12, 13 and 16–18) withanolides. Of normal–type withanolides, a chemical conversion from the 16α,17α–epoxywithanolide (16) to Δ13,14–16α–hydroxywithanolide (18) was achieved by Wagner–Meerwein rearrangement. All isolates were evaluated for their cytotoxicity against four human tumor cell lines (HCT–116, HepG2, MCF–7 and A375). Among them, compounds 1–3, 6–8, 14, 16–18 showed cytotoxic activity with IC50 values of 0.24–8.71 μM.
中文翻译:
臭椿(Tubocapsicum anomalum)地上部分的细胞毒性withanolides
十点新睡茄(1 - 10)和三个人工睡茄(11 - 13)获自的地上部分分离Tubocapsicum anomalum具有五个已知类似物(一起14 - 18)。它们的结构是根据广泛的光谱学和化学方法确定的。它们包括七个acnistin型(14,11,14和15),三个withajardin型(5 - 7),和八个正常型(8 - 10,12,13和16 – 18)的醇化物。正常型睡茄内酯,来自16的化学转化的α,17 α -epoxywithanolide(16),以Δ 13,14 -16 α -hydroxywithanolide(18)通过瓦格纳米尔文重排来实现。评估了所有分离株对四种人类肿瘤细胞系(HCT–116,HepG2,MCF–7和A375)的细胞毒性。其中化合物1 - 3,6 - 8,14,16 - 18显示细胞毒活性与IC 50个的值0.24-8.71 μ M.