Conithiaquinones A and B, Tetracyclic Cytotoxic Meroterpenes from the Mediterranean Ascidian Aplidium conicum

Chemical investigation of the Mediterranean ascidian A. conicum resulted in the isolation of two new meroterpenes, the conithiaquinones A (1) and B (2), in addition to two previously reported chromenols (3 and 4) and conicaquinones (5 and 6). The structures of conithiaquinones A and B were determine...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-06, Vol.2013 (16), p.3241-3246
Main Authors: Menna, Marialuisa, Aiello, Anna, D'Aniello, Filomena, Imperatore, Concetta, Luciano, Paolo, Vitalone, Rocco, Irace, Carlo, Santamaria, Rita
Format: Article
Language:English
Subjects:
Breast cancer
Medicinal chemistry
Natural products
Structure elucidation
Terpenoids
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Summary:Chemical investigation of the Mediterranean ascidian A. conicum resulted in the isolation of two new meroterpenes, the conithiaquinones A (1) and B (2), in addition to two previously reported chromenols (3 and 4) and conicaquinones (5 and 6). The structures of conithiaquinones A and B were determined by interpretation of spectroscopic data, and regiochemical and stereochemical assignments were achieved with the aid of computational methods, including the recently developed DP4 NMR spectral prediction method. Both conithiaquinones A and B showed significant effects on the growth and viability of cells, with 1 showing interesting cytotoxicity against human breast cancer cells. Two meroterpenes, conithiaquinones A (1) and B (2), were isolated from the ascidian A. conicum, and their stereochemical structures were determined with the aid of computational methods, including the recently developed DP4 NMR spectral prediction method. Both conithiaquinones showed significant effects on cell viability, with 1 showing an interesting cytotoxicity against human breast cancer cells.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300260