Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)
Phyllodesmium longicirrum is the largest aeolidoidean species known to date, and extremely rich in terpenoid chemistry. Herein we report the isolation of a total of 19 secondary metabolites from a single specimen of this species, i.e., steroids 1–4, cembranoid diterpenes 5–13, complex biscembranoids...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2017-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.13.50 |
| _version_ | 1818612358816202752 |
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| author | Alexander Bogdanov Cora Hertzer Stefan Kehraus Samuel Nietzer Sven Rohde Peter J. Schupp Heike Wägele Gabriele M. König |
| author_facet | Alexander Bogdanov Cora Hertzer Stefan Kehraus Samuel Nietzer Sven Rohde Peter J. Schupp Heike Wägele Gabriele M. König |
| author_sort | Alexander Bogdanov |
| collection | DOAJ |
| description | Phyllodesmium longicirrum is the largest aeolidoidean species known to date, and extremely rich in terpenoid chemistry. Herein we report the isolation of a total of 19 secondary metabolites from a single specimen of this species, i.e., steroids 1–4, cembranoid diterpenes 5–13, complex biscembranoids 14 and 15, and the chatancin-type diterpenes 16–19. These compounds resemble those from soft corals of the genus Sarcophyton, of which to date, however, only S. trocheliophorum is described as a food source for P. longicirrum. Fish feeding deterrent activity was determined using the tropical puffer fish Canthigaster solandri, and showed activity for (2S)-isosarcophytoxide (10), cembranoid bisepoxide 12 and 4-oxochatancin (16). Determining the metabolome of P. longicirrum and its bioactivity, makes it evident that this seemingly vulnerable soft bodied animal is well protected from fish by its chemical arsenal. |
| first_indexed | 2024-12-16T15:44:58Z |
| format | Article |
| id | doaj.art-72f26e934d5b4f7badbb792bfd0659bf |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T15:44:58Z |
| publishDate | 2017-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-72f26e934d5b4f7badbb792bfd0659bf2022-12-21T22:25:51ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-03-0113150251910.3762/bjoc.13.501860-5397-13-50Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)Alexander Bogdanov0Cora Hertzer1Stefan Kehraus2Samuel Nietzer3Sven Rohde4Peter J. Schupp5Heike Wägele6Gabriele M. König7Institute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, GermanyInstitute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, GermanyInstitute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, GermanyInstitute for Chemistry and Biology of the Marine Environment (ICBM), Carl-von-Ossietzki University Oldenburg, Schleusenstraße 1, 26382 Wilhelmshaven, GermanyInstitute for Chemistry and Biology of the Marine Environment (ICBM), Carl-von-Ossietzki University Oldenburg, Schleusenstraße 1, 26382 Wilhelmshaven, GermanyInstitute for Chemistry and Biology of the Marine Environment (ICBM), Carl-von-Ossietzki University Oldenburg, Schleusenstraße 1, 26382 Wilhelmshaven, GermanyZoologisches Forschungsmuseum Alexander Koenig, Adenauerallee 160, 53113 Bonn, GermanyInstitute for Pharmaceutical Biology, University of Bonn, Nussallee 6, 53115 Bonn, GermanyPhyllodesmium longicirrum is the largest aeolidoidean species known to date, and extremely rich in terpenoid chemistry. Herein we report the isolation of a total of 19 secondary metabolites from a single specimen of this species, i.e., steroids 1–4, cembranoid diterpenes 5–13, complex biscembranoids 14 and 15, and the chatancin-type diterpenes 16–19. These compounds resemble those from soft corals of the genus Sarcophyton, of which to date, however, only S. trocheliophorum is described as a food source for P. longicirrum. Fish feeding deterrent activity was determined using the tropical puffer fish Canthigaster solandri, and showed activity for (2S)-isosarcophytoxide (10), cembranoid bisepoxide 12 and 4-oxochatancin (16). Determining the metabolome of P. longicirrum and its bioactivity, makes it evident that this seemingly vulnerable soft bodied animal is well protected from fish by its chemical arsenal.https://doi.org/10.3762/bjoc.13.50chemical defensechemoecologynatural compoundsNudibranchiaPhyllodesmium longicirrum |
| spellingShingle | Alexander Bogdanov Cora Hertzer Stefan Kehraus Samuel Nietzer Sven Rohde Peter J. Schupp Heike Wägele Gabriele M. König Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia) Beilstein Journal of Organic Chemistry chemical defense chemoecology natural compounds Nudibranchia Phyllodesmium longicirrum |
| title | Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia) |
| title_full | Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia) |
| title_fullStr | Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia) |
| title_full_unstemmed | Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia) |
| title_short | Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia) |
| title_sort | secondary metabolome and its defensive role in the aeolidoidean phyllodesmium longicirrum gastropoda heterobranchia nudibranchia |
| topic | chemical defense chemoecology natural compounds Nudibranchia Phyllodesmium longicirrum |
| url | https://doi.org/10.3762/bjoc.13.50 |
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