Bioactive isoquinolinequinone alkaloids from the South China Sea nudibranch Jorunna funebris and its sponge-prey Xestospongia sp.

被引:37
作者
Huang, Ren-Yong [1 ]
Chen, Wen-Ting [1 ]
Kurtan, Tibor [2 ]
Mandi, Attila [2 ]
Ding, Jian [1 ]
Li, Jia [1 ]
Li, Xu-Wen [1 ]
Guo, Yue-Wei [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
[2] Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary
基金
新加坡国家研究基金会;
关键词
epimer; NF-kappa B signaling pathway; TDDFT ECD; tetrahydroisoquinolinequinone; KAPPA-B; ASSAY;
D O I
10.4155/fmc.15.169
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
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-kappa B 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.
引用
收藏
页码:17 / 27
页数:11
相关论文
共 20 条
[1]  
Avila C., 2007, MOLLUSCS CHEMOECOLOG
[2]   Systematic revision of Jorunna Bergh, 1876 (Nudibranchia: Discodorididae) with a morphological phylogenetic analysis [J].
Camacho-Garcia, Yolanda E. ;
Gosliner, Terrence M. .
JOURNAL OF MOLLUSCAN STUDIES, 2008, 74 :143-181
[3]  
Cimino G, 2005, PHYTOCHEM REV, V3, P285
[4]  
Cimino G, 2001, METABOLITES MARINE O
[5]   Ansellone A, a Sesterterpenoid Isolated from the Nudibranch Cadlina luteromarginata and the Sponge Phorbas sp., Activates the cAMP Signaling Pathway [J].
Daoust, Julie ;
Fontana, Angelo ;
Merchant, Catherine E. ;
de Voogd, Nicole J. ;
Patrick, Brian O. ;
Kieffer, Timothy J. ;
Andersen, Raymond J. .
ORGANIC LETTERS, 2010, 12 (14) :3208-3211
[6]   A new antitumor isoquinoline alkaloid from the marine nudibranch Jorunna funebris [J].
Fontana, A ;
Cavaliere, P ;
Wahidulla, S ;
Naik, CG ;
Cimino, G .
TETRAHEDRON, 2000, 56 (37) :7305-7308
[7]   ANTIMICROBIAL METABOLITES OF THE SPONGE RENIERA SP [J].
FRINCKE, JM ;
FAULKNER, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (01) :265-269
[8]  
Frisch M, 2015, Gaussian 09, revision a 02
[9]   New isoquinolinequinone alkaloids from the South China Sea nudibranch Jorunna funebris and its possible sponge-prey Xestospongia sp. [J].
He, Wen-Fei ;
Li, Yan ;
Feng, Mei-Tang ;
Gavagnin, Margherita ;
Mollo, Ernesto ;
Mao, Shui-Chun ;
Guo, Yue-Wei .
FITOTERAPIA, 2014, 96 :109-114
[10]   Nuclear factor κB is a molecular target for sulforaphane-mediated anti-inflammatory mechanisms [J].
Heiss, E ;
Herhaus, C ;
Klimo, K ;
Bartsch, H ;
Gerhäuser, C .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (34) :32008-32015