Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa

Sabrin Ibraham, Rainer Ebel, Victor Wray, Werner E.G. Muller, RuAngelie Edrada-Ebel, Peter 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 (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.
LanguageEnglish
Pages1358-1364
Number of pages6
JournalJournal of Natural Products
Volume71
Issue number8
DOIs
Publication statusPublished - Aug 2008

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

Keywords

  • diacarperoxides
  • norterpene cyclic peroxides
  • sponges
  • diacarnus megaspinorhabdosa
  • plants
  • pharmacology
  • drugs

Cite this

Ibraham, Sabrin ; Ebel, Rainer ; Wray, Victor ; Muller, Werner E.G. ; Edrada-Ebel, RuAngelie ; Proksch, Peter. / 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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Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa. / Ibraham, Sabrin; Ebel, Rainer; Wray, Victor; Muller, Werner E.G.; Edrada-Ebel, RuAngelie; Proksch, Peter.

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

Research output: Contribution to journalArticle

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T1 - Diacarperoxides, norterpene cyclic peroxides from the sponge Diacarnus megaspinorhabdosa

AU - Ibraham, Sabrin

AU - Ebel, Rainer

AU - Wray, Victor

AU - Muller, Werner E.G.

AU - Edrada-Ebel, RuAngelie

AU - Proksch, Peter

PY - 2008/8

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N2 - 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.

AB - 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.

KW - diacarperoxides

KW - norterpene cyclic peroxides

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KW - diacarnus megaspinorhabdosa

KW - plants

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