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Arbolodinines A−C, biologically-active aspidofractinine-aspidofractinine, aspidofractinine-strychnan, and kopsine-strychnan bisindole alkaloids from Kopsia arborea
Tetrahedron ( IF 2.1 ) Pub Date : 2020-11-27 , DOI: 10.1016/j.tet.2020.131802
Soon-Kit Wong , Joanne Soon-Yee Yeap , Chun-Hoe Tan , Kae-Shin Sim , Siew-Huah Lim , Yun-Yee Low , Toh-Seok Kam

Three new bisindole alkaloids, arbolodinines A−C, comprising aspidofractinine-aspidofractinine, aspidofractinine-strychnan, and kopsine-strychnan alkaloids, respectively, were isolated from the stem bark extract of the Malayan Kopsia arborea. The structures of the alkaloids were elucidated based on analysis of the spectroscopic data while the absolute configurations were established based on experimental and calculated ECD data. Arbolodinine A is characterized by the union of two aspidofractinine halves with rare and unusual branching from C-5′ of an iminium/carboxylate zwitterion of one aspidofractinine half to the olefinic C-14 of the other aspidofractinine half, while arbolodinines B and C represent first examples of aspidofractinine-strychnan and kopsine-strychnan bisindoles, respectively. Arbolodinine B displayed pronounced cytotoxic effects against an array of human cancer cell lines, including KB, vincristine-resistant KB, PC-3, HCT 116, HT-29, MDA-MB-231, MCF7 and A549 cells with IC50 values ranging from 1.3 to 9.6 μM.



中文翻译:

Arbolodinines A-C,生物活性aspidofractinine-aspidofractinine,aspidofractinine-strychnan,和kopsine-strychnan从双吲哚生物碱蕊木属梓

三个新的双吲哚生物碱,arbolodinines A-C,其包含aspidofractinine-aspidofractinine,aspidofractinine-strychnan,和kopsine-strychnan生物碱,分别从马来亚的树皮提取物中分离蕊木属梓。基于光谱数据的分析阐明了生物碱的结构,而基于实验和计算出的ECD数据建立了绝对构型。Arbolodinine A的特征是两个半胱氨酸吗啡联合,从一个半胱氨酸吗啡的亚胺/羧酸盐两性离子的C-5'到另一个半胱氨酸吗啡的烯属C-14的稀有和不寻常分支,而阿波罗地宁B和C分别代表Aspidofractinine-strychnan和kopsine-strychnan双吲哚的例子。Arbolodinine B对一系列人类癌细胞系具有明显的细胞毒性作用,包括KB,长春新碱抗性KB,PC-3,HCT 116,HT-29,MDA-MB-231,MCF7和A549细胞,IC 50值为1.3至9.6μM。

更新日期:2020-12-17
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