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Thiodiketopiperazines with two spirocyclic centers extracted from Botryosphaeria mamane, an endophytic fungus isolated from Bixa orellana L.
Phytochemistry ( IF 3.2 ) Pub Date : 2019-02-01 , DOI: 10.1016/j.phytochem.2018.11.007
Fatima Barakat , Marieke Vansteelandt , Asih Triastuti , Patricia Jargeat , Denis Jacquemin , Jérôme Graton , Kember Mejia , Billy Cabanillas , Laure Vendier , Jean-Luc Stigliani , Mohamed Haddad , Nicolas Fabre

Three thiodiketopiperazines, botryosulfuranols A-C (1-3) were isolated from the endophytic fungus Botryosphaeria mamane. The three compounds present sulfur atoms on α- and β-positions of phenylalanine derived residues and unprecedented two spirocyclic centers at C-4 and C-2'. Their planar structures were determined by spectroscopic analysis and absolute configurations were achieved by X-ray diffraction analysis and ECD and NMR chemical shifts calculations. Botryosulfuranol A (1) was the most cytotoxic compound against four cancer cell lines (HT-29, HepG2, Caco-2, HeLa) and two healthy cell lines (IEC6, Vero) highlighting the importance of an electrophilic center for cell growth inhibition.

中文翻译:

从 Botryosphaeria mamane 中提取的具有两个螺环中心的硫代酮哌嗪,这是一种从 Bixa orellana L. 中分离的内生真菌。

从内生真菌 Botryosphaeria mamane 中分离出三种硫代二酮哌嗪、葡萄硫醇 AC (1-3)。这三种化合物在苯丙氨酸衍生残基的 α- 和 β- 位存在硫原子,并且在 C-4 和 C-2' 处具有前所未有的两个螺环中心。它们的平面结构通过光谱分析确定,绝对构型通过 X 射线衍射分析和 ECD 和 NMR 化学位移计算获得。Botryosulfuranol A (1) 是对四种癌细胞系(HT-29、HepG2、Caco-2、HeLa)和两种健康细胞系(IEC6、Vero)最具细胞毒性的化合物,突出了亲电子中心对细胞生长抑制的重要性。
更新日期:2019-02-01
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