Expanding the Repertoire of Spongian-16-One Derivatives in Australian Nudibranchs of the Genus <i>Goniobranchus</i> and Evaluation of Their Anatomical Distribution
Extracts of the mantle and viscera of the Indo-Pacific nudibranchs <i>Goniobranchus aureopurpureus</i> and <i>Goniobranchus</i> sp. 1 afforded 11 new diterpenoids (<b>1</b>–<b>11</b>), all of which possess a tetracyclic spongian-16-one scaffold with ex...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-11-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/19/12/680 |
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| author | Louise C. Forster Jack K. Clegg Karen L. Cheney Mary J. Garson |
| author_facet | Louise C. Forster Jack K. Clegg Karen L. Cheney Mary J. Garson |
| author_sort | Louise C. Forster |
| collection | DOAJ |
| description | Extracts of the mantle and viscera of the Indo-Pacific nudibranchs <i>Goniobranchus aureopurpureus</i> and <i>Goniobranchus</i> sp. 1 afforded 11 new diterpenoids (<b>1</b>–<b>11</b>), all of which possess a tetracyclic spongian-16-one scaffold with extensive oxidation at C-6, C-7, C-11, C-12, C-13, and/or C-20. The structures and relative configuration were investigated by NMR experiments, while X-ray crystallography provided the absolute configuration of <b>1</b>, including a 2′<i>S</i> configuration for the 2-methylbutanoate substituent located at C-7. Dissection of animal tissue revealed that the mantle and viscera tissues differed in their metabolite composition with diterpenes <b>1</b>–<b>11</b> present in the mantle tissue of the two nudibranch species. |
| first_indexed | 2024-03-10T03:41:27Z |
| format | Article |
| id | doaj.art-d5494b76f0ae4ba299ba94152ef7e762 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T03:41:27Z |
| publishDate | 2021-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-d5494b76f0ae4ba299ba94152ef7e7622023-11-23T09:18:09ZengMDPI AGMarine Drugs1660-33972021-11-01191268010.3390/md19120680Expanding the Repertoire of Spongian-16-One Derivatives in Australian Nudibranchs of the Genus <i>Goniobranchus</i> and Evaluation of Their Anatomical DistributionLouise C. Forster0Jack K. Clegg1Karen L. Cheney2Mary J. Garson3School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD 4072, AustraliaSchool of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD 4072, AustraliaSchool of Biological Sciences, The University of Queensland, St. Lucia, QLD 4072, AustraliaSchool of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD 4072, AustraliaExtracts of the mantle and viscera of the Indo-Pacific nudibranchs <i>Goniobranchus aureopurpureus</i> and <i>Goniobranchus</i> sp. 1 afforded 11 new diterpenoids (<b>1</b>–<b>11</b>), all of which possess a tetracyclic spongian-16-one scaffold with extensive oxidation at C-6, C-7, C-11, C-12, C-13, and/or C-20. The structures and relative configuration were investigated by NMR experiments, while X-ray crystallography provided the absolute configuration of <b>1</b>, including a 2′<i>S</i> configuration for the 2-methylbutanoate substituent located at C-7. Dissection of animal tissue revealed that the mantle and viscera tissues differed in their metabolite composition with diterpenes <b>1</b>–<b>11</b> present in the mantle tissue of the two nudibranch species.https://www.mdpi.com/1660-3397/19/12/680diterpenesnudibranchChromodorididae<i>Goniobranchus aureopurpureus</i>X-ray crystallography |
| spellingShingle | Louise C. Forster Jack K. Clegg Karen L. Cheney Mary J. Garson Expanding the Repertoire of Spongian-16-One Derivatives in Australian Nudibranchs of the Genus <i>Goniobranchus</i> and Evaluation of Their Anatomical Distribution Marine Drugs diterpenes nudibranch Chromodorididae <i>Goniobranchus aureopurpureus</i> X-ray crystallography |
| title | Expanding the Repertoire of Spongian-16-One Derivatives in Australian Nudibranchs of the Genus <i>Goniobranchus</i> and Evaluation of Their Anatomical Distribution |
| title_full | Expanding the Repertoire of Spongian-16-One Derivatives in Australian Nudibranchs of the Genus <i>Goniobranchus</i> and Evaluation of Their Anatomical Distribution |
| title_fullStr | Expanding the Repertoire of Spongian-16-One Derivatives in Australian Nudibranchs of the Genus <i>Goniobranchus</i> and Evaluation of Their Anatomical Distribution |
| title_full_unstemmed | Expanding the Repertoire of Spongian-16-One Derivatives in Australian Nudibranchs of the Genus <i>Goniobranchus</i> and Evaluation of Their Anatomical Distribution |
| title_short | Expanding the Repertoire of Spongian-16-One Derivatives in Australian Nudibranchs of the Genus <i>Goniobranchus</i> and Evaluation of Their Anatomical Distribution |
| title_sort | expanding the repertoire of spongian 16 one derivatives in australian nudibranchs of the genus i goniobranchus i and evaluation of their anatomical distribution |
| topic | diterpenes nudibranch Chromodorididae <i>Goniobranchus aureopurpureus</i> X-ray crystallography |
| url | https://www.mdpi.com/1660-3397/19/12/680 |
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