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塞巴斯蒂宁A和B,从巴西海鞘德氏囊海鞘中提取的新型生物活性吡啶吖啶生物碱。

Sebastianines A and B, novel biologically active pyridoacridine alkaloids from the Brazilian ascidian Cystodytes dellechiajei.

作者信息

Torres Yohandra R, Bugni Tim S, Berlinck Roberto G S, Ireland Chris M, Magalhães Alviclér, Ferreira Antonio G, Moreira Da Rocha Rosana

机构信息

Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, CEP 13560-970, São Carlos, SP, Brazil.

出版信息

J Org Chem. 2002 Jul 26;67(15):5429-32. doi: 10.1021/jo011174h.

Abstract

Fractionation of the crude methanol extract of the ascidian Cystodytes dellechiajei collected in Brazil yielded two novel alkaloids, sebastianine A (1) and sebastianine B (2). The structures of both 1 and 2 were established by analysis of spectroscopic data, indicating an unprecedented ring system for both compounds, comprising a pyridoacridine system fused with a pyrrole unit in sebastianine A (1) and a pyridoacridine system fused with a pyrrolidine system condensed with alpha-hydroxyisovaleric acid in sebastianine B (2). Both alkaloids displayed a cytotoxic profile against a panel of HCT-116 colon carcinoma cells indicative of a p53 dependent mechanism.

摘要

对在巴西采集的海鞘类动物德氏囊海鞘(Cystodytes dellechiajei)的粗甲醇提取物进行分馏,得到了两种新生物碱,塞巴斯蒂安碱A(1)和塞巴斯蒂安碱B(2)。通过光谱数据分析确定了1和2的结构,表明这两种化合物都具有前所未有的环系,塞巴斯蒂安碱A(1)包含一个与吡咯单元稠合的吡啶并吖啶体系,而塞巴斯蒂安碱B(2)包含一个与吡咯烷体系稠合且与α-羟基异戊酸缩合的吡啶并吖啶体系。这两种生物碱对一组HCT - 116结肠癌细胞均显示出细胞毒性,表明其作用机制依赖于p53。

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