来自中国南海裸鳃亚目动物黑指纹海兔及其海绵猎物黄海绵的生物活性异喹啉醌生物碱
Bioactive isoquinolinequinone alkaloids from the South China Sea nudibranch Jorunna funebris and its sponge-prey Xestospongia sp.
作者信息
Huang Ren-Yong, Chen Wen-Ting, Kurtán Tibor, Mándi Attila, Ding Jian, Li Jia, Li Xu-Wen, Guo Yue-Wei
机构信息
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, People's Republic of China.
Department of Organic Chemistry, University of Debrecen, PO Box 20, 4010 Debrecen, Hungary.
出版信息
Future Med Chem. 2016 Jan;8(1):17-27. doi: 10.4155/fmc.15.169. Epub 2015 Dec 21.
BACKGROUND
Nudibranchs are slug-like invertebrates, well known as rich sources of biologically active secondary metabolites with highly chemical diversity and complexity. The production of such interesting metabolites was possibly influenced by their diet relationship with sponges such as Xestospongia.
RESULTS
Our continuous investigation of South China Sea nudibranch Jorunna funebris and its sponge-prey Xestospongia sp. led to the isolation of two new and eight known metabolites (1-10). The absolute configurations were determined by time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) method and by the comparison of ECD spectra. In bioassays, 1-4 and 7 showed strong NF-κB inhibitory activity, 4-6 exhibited considerable cytotoxicity against A549 and HL-60 tumor cell lines.
CONCLUSION
Five unusual isoquinolinequinones (3, 7-10) were discovered from both two animals, further confirmed their predator-prey relationship. Preliminary bioassay results and structure-activity relationship studies suggested that several isolated compounds were potential to be drug leads.
背景
裸鳃亚目动物是鼻涕虫状的无脊椎动物，以富含具有高度化学多样性和复杂性的生物活性次生代谢产物而闻名。这类有趣的代谢产物的产生可能受其与如黄海绵属等海绵的饮食关系影响。
结果
我们对南海裸鳃亚目动物线纹背肛海兔及其海绵猎物黄海绵属物种的持续研究，导致分离出两种新的和八种已知的代谢产物（1 - 10）。通过含时密度泛函理论（TDDFT）电子圆二色光谱（ECD）方法并比较ECD光谱确定了绝对构型。在生物测定中，1 - 4和7显示出强烈的核因子κB抑制活性，4 - 6对A549和HL - 60肿瘤细胞系表现出相当大的细胞毒性。
结论
从这两种动物中均发现了五种不寻常的异喹啉醌（3，7 - 10），进一步证实了它们的捕食者 - 猎物关系。初步生物测定结果和构效关系研究表明，几种分离出的化合物有潜力成为药物先导物。
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