Australindolones, New Aminopyrimidine Substituted Indolone Alkaloids from an Antarctic Tunicate <i>Synoicum</i> sp.
Five new alkaloids have been isolated from the lipophilic extract of the Antarctic tunicate <i>Synoicum</i> sp. Deep-sea specimens of <i>Synoicum</i> sp. were collected during a 2011 cruise of the R/V <i>Nathanial B. Palmer</i> to the southern Scotia Arc, Antarcti...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-03-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/20/3/196 |
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| author | Sofia Kokkaliari Kim Pham Nargess Shahbazi Laurent Calcul Lukasz Wojtas Nerida G. Wilson Alexander D. Crawford Bill J. Baker |
| author_facet | Sofia Kokkaliari Kim Pham Nargess Shahbazi Laurent Calcul Lukasz Wojtas Nerida G. Wilson Alexander D. Crawford Bill J. Baker |
| author_sort | Sofia Kokkaliari |
| collection | DOAJ |
| description | Five new alkaloids have been isolated from the lipophilic extract of the Antarctic tunicate <i>Synoicum</i> sp. Deep-sea specimens of <i>Synoicum</i> sp. were collected during a 2011 cruise of the R/V <i>Nathanial B. Palmer</i> to the southern Scotia Arc, Antarctica. Crude extracts from the invertebrates obtained during the cruise were screened in a zebrafish-based phenotypic assay. The <i>Synoicum</i> sp. extract induced embryonic dysmorphology characterized by axis truncation, leading to the isolation of aminopyrimidine substituted indolone (<b>1</b>–<b>4</b>) and indole (<b>5</b>–<b>12</b>) alkaloids. While the primary bioactivity tracked with previously reported meridianins A–G (<b>5</b>–<b>11</b>), further investigation resulted in the isolation and characterization of australindolones A–D (<b>1</b>–<b>4</b>) and the previously unreported meridianin H (<b>12</b>). |
| first_indexed | 2024-03-09T13:31:12Z |
| format | Article |
| id | doaj.art-76fea00d4e554751a6dcf80dc943ada0 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-09T13:31:12Z |
| publishDate | 2022-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-76fea00d4e554751a6dcf80dc943ada02023-11-30T21:18:10ZengMDPI AGMarine Drugs1660-33972022-03-0120319610.3390/md20030196Australindolones, New Aminopyrimidine Substituted Indolone Alkaloids from an Antarctic Tunicate <i>Synoicum</i> sp.Sofia Kokkaliari0Kim Pham1Nargess Shahbazi2Laurent Calcul3Lukasz Wojtas4Nerida G. Wilson5Alexander D. Crawford6Bill J. Baker7Department of Chemistry, University of South Florida, 4202 E. Fowler Ave., CHE205, Tampa, FL 33620, USADepartment of Chemistry, University of South Florida, 4202 E. Fowler Ave., CHE205, Tampa, FL 33620, USADepartment of Preclinical Sciences and Pathology, Norwegian University of Life Sciences (NMBU), 1430 Ås, NorwayDepartment of Chemistry, University of South Florida, 4202 E. Fowler Ave., CHE205, Tampa, FL 33620, USADepartment of Chemistry, University of South Florida, 4202 E. Fowler Ave., CHE205, Tampa, FL 33620, USAResearch & Collections, Western Australia Museum, 49 Kew Street, Welshpool, WA 6106, AustraliaDepartment of Preclinical Sciences and Pathology, Norwegian University of Life Sciences (NMBU), 1430 Ås, NorwayDepartment of Chemistry, University of South Florida, 4202 E. Fowler Ave., CHE205, Tampa, FL 33620, USAFive new alkaloids have been isolated from the lipophilic extract of the Antarctic tunicate <i>Synoicum</i> sp. Deep-sea specimens of <i>Synoicum</i> sp. were collected during a 2011 cruise of the R/V <i>Nathanial B. Palmer</i> to the southern Scotia Arc, Antarctica. Crude extracts from the invertebrates obtained during the cruise were screened in a zebrafish-based phenotypic assay. The <i>Synoicum</i> sp. extract induced embryonic dysmorphology characterized by axis truncation, leading to the isolation of aminopyrimidine substituted indolone (<b>1</b>–<b>4</b>) and indole (<b>5</b>–<b>12</b>) alkaloids. While the primary bioactivity tracked with previously reported meridianins A–G (<b>5</b>–<b>11</b>), further investigation resulted in the isolation and characterization of australindolones A–D (<b>1</b>–<b>4</b>) and the previously unreported meridianin H (<b>12</b>).https://www.mdpi.com/1660-3397/20/3/196ascidiansindole alkaloidszebrafishmeridianins |
| spellingShingle | Sofia Kokkaliari Kim Pham Nargess Shahbazi Laurent Calcul Lukasz Wojtas Nerida G. Wilson Alexander D. Crawford Bill J. Baker Australindolones, New Aminopyrimidine Substituted Indolone Alkaloids from an Antarctic Tunicate <i>Synoicum</i> sp. Marine Drugs ascidians indole alkaloids zebrafish meridianins |
| title | Australindolones, New Aminopyrimidine Substituted Indolone Alkaloids from an Antarctic Tunicate <i>Synoicum</i> sp. |
| title_full | Australindolones, New Aminopyrimidine Substituted Indolone Alkaloids from an Antarctic Tunicate <i>Synoicum</i> sp. |
| title_fullStr | Australindolones, New Aminopyrimidine Substituted Indolone Alkaloids from an Antarctic Tunicate <i>Synoicum</i> sp. |
| title_full_unstemmed | Australindolones, New Aminopyrimidine Substituted Indolone Alkaloids from an Antarctic Tunicate <i>Synoicum</i> sp. |
| title_short | Australindolones, New Aminopyrimidine Substituted Indolone Alkaloids from an Antarctic Tunicate <i>Synoicum</i> sp. |
| title_sort | australindolones new aminopyrimidine substituted indolone alkaloids from an antarctic tunicate i synoicum i sp |
| topic | ascidians indole alkaloids zebrafish meridianins |
| url | https://www.mdpi.com/1660-3397/20/3/196 |
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