The constituents of marine sponges. VI. diterpenoid metabolites of the New Zealand sponge chelonaplysilla violacea

Patricia R. Bergquist, Peter Karuso, Peter Karuso

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The sponge Chelonaplysilla violacea, collected from New Zealand coastal waters, contains as major constituents the diterpenoids aplyviolene (1a), norrisolide (2), dendrillolide A (3) aplyroseol-7 (4), spongian-16-one (5), chelonaplysin C (6), and a series of new compounds cheloviolene A-F and cheloviolin. Structures were assigned to cheloviolene A (7), [3aR-[3a, 4(1R*, 3aR*, 8aS*), 5, 6a]]-5-hydroxy-4(1, 4, 4-trimethyl-8-methylenedecahydroazulen-1-yl) tetrahydrofuro [2, 3- b] furan-2(3H)-one, cheloviolene B (8), [3aR-[3a, 4a(1R*, 3aR*, 8aS*), 5, 6a]]-5-hydroxy-4-(1, 4, 4-trimethyl-8-methylenedecahydroazulen-1-yl) tetrahydrofuro [2, 3-b]furan-2(3H)-one, cheloviolene C (9), [1'(1R*, 3aS*, 7aS*), 4]-4-[1-(acetyloxymethyl)-2-(4, 4, 7a-trimethyloctahydro-1H-inden-1-yl)prop-2-enyl] dihydrofuran -2(3H)-one, cheloviolene D (10), methyl [3, 4(1R*, 3aR*, 8aS*)]-5-oxo-4-(1, 4, 4-trimethyl-8-methylenedecahydroazulen-1-yl)tetrahydrofuran-3-acetate, cheloviolene E (11), methyl [3, 4-(1R*, 3aS*, 7aS*)]-5-oxo-4-[1-(4, 4, 7a-trimethyloctahydro-1H-inden-1-yl) ethenyl ]tetrahydrofuran-3-acetate, and cheloviolene F (12), [4, 5(1R*, 3R*, 8aS*)]-4-(acetyloxymethyl)-5-(1, 4, 4-trimethyl-8-methylenedecahydroazulen-1-yl) tetrahydro-2H-pyran-2-one, by using spectroscopic methods; the structure (13) was deduced for cheloviolin, [1S-[1, 5, 6, 8R*(1aS*, 3aS*, 7aS*, 7b-R*)]]-6-acetyloxy-8-(4, 4, 7a-trimethyldecahydrocylopropa[a] naphthalen-la-yl)-2, 7-dioxabicyclo- [3.2.1]octan-3-one.

Original languageEnglish
Pages (from-to)623-632
Number of pages10
JournalAustralian Journal of Chemistry
Volume46
Issue number5
DOIs
Publication statusPublished - 1993
Externally publishedYes

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