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Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa

Ibraham, Sabrin and Ebel, Rainer and Wray, Victor and Muller, Werner E.G. and Edrada-Ebel, RuAngelie and Proksch, Peter (2008) Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa. Journal of Natural Products, 71 (8). pp. 1358-1364. ISSN 0163-3864

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Abstract

Chemical investigation of the hexane extract of the sponge Diacarnus megaspinorhabdosa provided a series of new norterpene derivatives including three norditerpene cyclic peroxides, diacarperoxides A, B, and C (1 to 3), four norsesterterpene cyclic peroxides, diacarperoxides D to G (4 to 7), and the acyclic norsesterterpene diacardiol A (8). In addition, known norterpene peroxide congeners were also isolated, which included a known norsesterterpene cyclic peroxide (9), nuapapuin A methyl ester (10), epimuqubilin B (11), methyl-2-epinuapapuinoate (12), and methyl diacarnoate A (13). The structures of the new compounds were established on the basis of one- and two-dimensional NMR spectroscopic studies (1H, 13C, COSY, HMQC, HMBC, and ROESY) as well as by mass spectrometric analyses. The relative configuration of chiral centers at C-2, C-3, and C-6 was assigned by established empirical rules. All compounds were evaluated for their cytotoxic properties in vitro using several human as well as murine cancer cell lines.