Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa.
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 ((1)H, (13)C, 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.
Ibrahim
Sabrin R M
SR
Institut für Pharmazeutische Biologie and Biotechnologie, Heinrich-Heine-Universität Düsseldorf, 40225 Düsseldorf, Germany.
Ebel
Rainer
R
Wray
Victor
V
Müller
Werner E G
WE
Edrada-Ebel
RuAngelie
R
Proksch
Peter
P
D000818:Animals; D006865:Hydrogenation; D009682:Magnetic Resonance Spectroscopy; D010545:Peroxides / Q000737:chemistry / Q000302:isolation & purification*; D011161:Porifera / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization
D010545:Peroxides