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-[3aα,4α(1R*,3aR*,8aS*),5β,6aα]]-5-hydroxy-4(1,4,4-trimethyl-8-methylenedecahydroazulen-1-yl) tetrahydrofuro [2,3- b] furan-2(3H)-one, cheloviolene B (8), [3aR-[3aα,4a(1R*,3aR*, 8aS*),5α,6aα]]-5-hydroxy-4-(1,4,4-trimethyl-8-methylenedecahydroazulen-1-yl) tetrahydrofuro [2,3-b]furan-2(3H)-one, cheloviolene C (9), [1'ξ(1R*,3aS*,7aS*),4ξ]-4-[1′-( acetyloxymethyl )-2′-(4,4,7a-trimethyloctahydro-1H-inden-1-yl)prop-2′-enyl] dihydrofuran -2(3H)-one, cheloviolene D (10), methyl [3α,4α(1R*,3aR*,8aS*)]-5-oxo-4-(1,4,4-trimethyl-8-methylenedecahydroazulen-1-yl)tetrahydrofuran-3-acetate, cheloviolene E (11), methyl [3α,4α-(1R*,3aS*,7aS*)]-5-oxo-4-[1′-(4,4,7a-trimethyloctahydro-1H-inden-1-yl) ethenyl ]tetrahydrofuran-3-acetate, and cheloviolene F (12), [4ξ,5ξ(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-[1α,5α,6α,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.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTChemistry of Sponges, VI. Scalarane Sesterterpenes from Hyatella intestinalisP. Karuso, R. C. Cambie, B. F. Bowden, and Patricia R. BergquistCite this: J. Nat. Prod. 1989, 52, 2, 289–293Publication Date (Print):March 1, 1989Publication History Published online1 July 2004Published inissue 1 March 1989https://pubs.acs.org/doi/10.1021/np50062a012https://doi.org/10.1021/np50062a012research-articleACS PublicationsRequest reuse permissionsArticle Views162Altmetric-Citations13LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

Saponification and methylation of the acidic fraction of an extract of the fruit of the New Zealand tree Pseudopanax arboreum has led to the isolation of a series of ring-A substituted and ring-A seco triterpenoids possessing oleanane or ursane skeletons. These include methyl 3-oxo-24-norurs-12-en-28-oate (1), dimethyl 4-oxo-3,24-dinor- 2,3-secours-12-ene-2,28-dioate (7), methyl 2α,3α,23-trihydroxyolean-12- en-28-oate (10), the ε-lactone of 23-hydroxy-4,17-dimethoxycarbonyl- 2,3-secours-12-en-2-oic acid (15), trimethyl 24-nor-2,3-secours-12-ene- 2,3,28-trioate (20), methyl 2-hydroxy-3-oxo-24-noroleana-1,4,12-trien- 28-oate (26), and methyl 2-hydroxy-3-oxo-24-norursa-1,4,12-trien-28- oate (27) whose parent acids have not hitherto been obtained as natural products. Other compounds are methyl 2α,3α-dihydroxyolean-12-en-28-oate (9), methyl 2α,3α-dihydroxyurs-12-en-28-oate (23), methyl asiatate (24), methyl arjunolate (13), the methoxy artefact (12), and the aryl- substituted methyl cinnamates (28), (29), (30) and (31). Neutral constituents include the esters (1), (9) and (10), stigmasterol and the sesquiterpene spathulenol (32).