Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa

S.R.M. Ibrahim, R. Ebel, V. Wray, W.E.G. Müller, R. Edrada-Ebel, P. Proksch

Research output: Contribution to journalArticle

22 Citations (Scopus)

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 (H, 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.
Original languageEnglish
Pages (from-to)1358-1364
Number of pages7
JournalJournal of Natural Products
Volume71
Issue number8
Early online date2 Aug 2008
DOIs
Publication statusPublished - Aug 2008

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Peroxides
Porifera
Diterpenes
Hexanes
Esters
Cells
Nuclear magnetic resonance
Derivatives
Cell Line
Neoplasms

Cite this

Ibrahim, S. R. M., Ebel, R., Wray, V., Müller, W. E. G., Edrada-Ebel, R., & Proksch, P. (2008). Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa. Journal of Natural Products, 71(8), 1358-1364. https://doi.org/10.1021/np800102u

Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa. / Ibrahim, S.R.M.; Ebel, R.; Wray, V.; Müller, W.E.G.; Edrada-Ebel, R.; Proksch, P.

In: Journal of Natural Products, Vol. 71, No. 8, 08.2008, p. 1358-1364.

Research output: Contribution to journalArticle

Ibrahim, SRM, Ebel, R, Wray, V, Müller, WEG, Edrada-Ebel, R & Proksch, P 2008, 'Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa', Journal of Natural Products, vol. 71, no. 8, pp. 1358-1364. https://doi.org/10.1021/np800102u
Ibrahim, S.R.M. ; Ebel, R. ; Wray, V. ; Müller, W.E.G. ; Edrada-Ebel, R. ; Proksch, P. / Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa. In: Journal of Natural Products. 2008 ; Vol. 71, No. 8. pp. 1358-1364.
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