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 journalArticleResearchpeer-review

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.

LanguageEnglish
Pages623-632
Number of pages10
JournalAustralian Journal of Chemistry
Volume46
Issue number5
DOIs
Publication statusPublished - 1993
Externally publishedYes

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Diterpenes
Metabolites
Acetates
Pyrans
Water
tetrahydrofuran
furan
aplyviolene
norrisolide

Cite this

@article{f8ad93a0ce5c4375a0a65f6be961d7c4,
title = "The constituents of marine sponges. VI. diterpenoid metabolites of the New Zealand sponge chelonaplysilla violacea",
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.",
author = "Bergquist, {Patricia R.} and Peter Karuso and Peter Karuso",
year = "1993",
doi = "10.1071/CH9930623",
language = "English",
volume = "46",
pages = "623--632",
journal = "Australian Journal of Chemistry",
issn = "0004-9425",
publisher = "CSIRO",
number = "5",

}

The constituents of marine sponges. VI. diterpenoid metabolites of the New Zealand sponge chelonaplysilla violacea. / Bergquist, Patricia R.; Karuso, Peter; Karuso, Peter.

In: Australian Journal of Chemistry, Vol. 46, No. 5, 1993, p. 623-632.

Research output: Contribution to journalArticleResearchpeer-review

TY - JOUR

T1 - The constituents of marine sponges. VI. diterpenoid metabolites of the New Zealand sponge chelonaplysilla violacea

AU - Bergquist, Patricia R.

AU - Karuso, Peter

AU - Karuso, Peter

PY - 1993

Y1 - 1993

N2 - 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.

AB - 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.

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U2 - 10.1071/CH9930623

DO - 10.1071/CH9930623

M3 - Article

VL - 46

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EP - 632

JO - Australian Journal of Chemistry

T2 - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

SN - 0004-9425

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