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Stable Catechol Keto Tautomers in Cytotoxic Heterodimeric Cyclic Diarylheptanoids from the Seagrass Zostera marina
Organic Letters ( IF 5.2 ) Pub Date : 2021-09-07 , DOI: 10.1021/acs.orglett.1c02537
Yan Li 1 , Laura Grauso 2 , Silvia Scarpato 3 , Nunzio Antonio Cacciola 4 , Francesca Borrelli 3 , Christian Zidorn 1 , Alfonso Mangoni 3
Affiliation  

Two diarylheptanoid heterodimers, zosterabisphenones A (1) and B (2), were isolated from the seagrass Zostera marina. They feature unprecedented catechol keto tautomers, stable because of steric constraints. Their structure elucidation was based on extensive low-temperature NMR studies and ECD and MS data, with the essential aid of DFT prediction of NMR and ECD spectra. Zosterabisphenone B (2) was selectively cytotoxic against the adenocarcinoma colon cancer cell line HCT116 with IC50 3.6 ± 1.1 μM at 48 h.

中文翻译:

海草带状藻细胞毒性异二聚体环状二芳基庚烷中的稳定儿茶酚酮互变异构体

从海草Zostera marina中分离出两种二芳基庚烷异二聚体,带状双苯酮 A ( 1 ) 和 B ( 2 ) 。它们具有前所未有的儿茶酚酮互变异构体,由于空间限制而稳定。它们的结构解析是基于广泛的低温核磁共振研究和 ECD 和 MS 数据,在 NMR 和 ECD 光谱的 DFT 预测的基本帮助下。Zosterabisphenone B ( 2 ) 对腺癌结肠癌细胞系 HCT116 具有选择性细胞毒性,48 小时时 IC 50 为3.6 ± 1.1 μM。
更新日期:2021-09-17
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