Targeted Isolation of Tsitsikammamines from the Antarctic Deep-Sea Sponge Latrunculia biformis by Molecular Networking and Anticancer Activity
The Antarctic deep-sea sponge Latrunculia (Latrunculia) biformis Kirkpatrick, 1908 (Class Demospongiae Sollas, Order Poecilosclerida Topsent, Latrunculiidae Topsent) was selected for chemical analyses due to its potent anticancer activity. Metabolomic analysis of its crude extract by HRMS/MS-based m...
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2018
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Online Access: | https://doi.org/10.3390/md16080268 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2019-00169-2 https://macau.uni-kiel.de/receive/macau_mods_00000147 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001092/marinedrugs-16-00268-v2.pdf |
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ftunivkiel:oai:macau.uni-kiel.de:macau_mods_00000147 2024-06-23T07:47:55+00:00 Targeted Isolation of Tsitsikammamines from the Antarctic Deep-Sea Sponge Latrunculia biformis by Molecular Networking and Anticancer Activity Li, Fengjie Janussen, Dorte Peifer, Christian Pérez-Victoria, Ignacio Tasdemir, Deniz 2018 https://doi.org/10.3390/md16080268 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2019-00169-2 https://macau.uni-kiel.de/receive/macau_mods_00000147 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001092/marinedrugs-16-00268-v2.pdf eng eng Marine drugs -- Mar Drugs -- 1660-3397 -- 1660-3397 https://doi.org/10.3390/md16080268 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2019-00169-2 https://macau.uni-kiel.de/receive/macau_mods_00000147 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001092/marinedrugs-16-00268-v2.pdf https://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess article ScholarlyArticle ddc:610 Published Version Tumor Cell Line Keratinocytes Animals Humans Porifera Pyrroles Quinolines Doxorubicin Type I DNA Topoisomerases Antineoplastic Agents Molecular Structure Protein Conformation Molecular Models Antarctica Molecular docking Marine sponge Deep-sea Latrunculia Molecular Networking Tsitsikammamine article Text doc-type:Article 2018 ftunivkiel https://doi.org/10.3390/md16080268 2024-06-12T14:19:15Z The Antarctic deep-sea sponge Latrunculia (Latrunculia) biformis Kirkpatrick, 1908 (Class Demospongiae Sollas, Order Poecilosclerida Topsent, Latrunculiidae Topsent) was selected for chemical analyses due to its potent anticancer activity. Metabolomic analysis of its crude extract by HRMS/MS-based molecular networking showed the presence of several clusters of pyrroloiminoquinone alkaloids, i.e., discorhabdin and epinardin-type brominated pyridopyrroloquinolines and tsitsikammamines, the non-brominated bis-pyrroloiminoquinones. Molecular networking approach combined with a bioactivity-guided isolation led to the targeted isolation of the known pyrroloiminoquinone tsitsikammamine A (1) and its new analog 16,17-dehydrotsitsikammamine A (2). The chemical structures of the compounds 1 and 2 were elucidated by spectroscopic analysis (one-dimensional (1D) and two-dimensional (2D) NMR, HR-ESIMS). Due to minute amounts, molecular modeling and docking was used to assess potential affinities to potential targets of the isolated compounds, including DNA intercalation, topoisomerase I-II, and indoleamine 2,3-dioxygenase enzymes. Tsitsikammamines represent a small class of pyrroloiminoquinone alkaloids that have only previously been reported from the South African sponge genus Tsitsikamma Samaai & Kelly and an Australian species of the sponge genus Zyzzya de Laubenfels. This is the first report of tsitsikammamines from the genus Latrunculia du Bocage and the successful application of molecular networking in the identification of comprehensive chemical inventory of L.biformis followed by targeted isolation of new molecules. This study highlights the high productivity of secondary metabolites of Latrunculia sponges and may shed new light on their biosynthetic origin and chemotaxonomy. Article in Journal/Newspaper Antarc* Antarctic Antarctica MACAU: Open Access Repository of Kiel University Antarctic The Antarctic Marine Drugs 16 8 268 |
institution |
Open Polar |
collection |
MACAU: Open Access Repository of Kiel University |
op_collection_id |
ftunivkiel |
language |
English |
topic |
article ScholarlyArticle ddc:610 Published Version Tumor Cell Line Keratinocytes Animals Humans Porifera Pyrroles Quinolines Doxorubicin Type I DNA Topoisomerases Antineoplastic Agents Molecular Structure Protein Conformation Molecular Models Antarctica Molecular docking Marine sponge Deep-sea Latrunculia Molecular Networking Tsitsikammamine |
spellingShingle |
article ScholarlyArticle ddc:610 Published Version Tumor Cell Line Keratinocytes Animals Humans Porifera Pyrroles Quinolines Doxorubicin Type I DNA Topoisomerases Antineoplastic Agents Molecular Structure Protein Conformation Molecular Models Antarctica Molecular docking Marine sponge Deep-sea Latrunculia Molecular Networking Tsitsikammamine Li, Fengjie Janussen, Dorte Peifer, Christian Pérez-Victoria, Ignacio Tasdemir, Deniz Targeted Isolation of Tsitsikammamines from the Antarctic Deep-Sea Sponge Latrunculia biformis by Molecular Networking and Anticancer Activity |
topic_facet |
article ScholarlyArticle ddc:610 Published Version Tumor Cell Line Keratinocytes Animals Humans Porifera Pyrroles Quinolines Doxorubicin Type I DNA Topoisomerases Antineoplastic Agents Molecular Structure Protein Conformation Molecular Models Antarctica Molecular docking Marine sponge Deep-sea Latrunculia Molecular Networking Tsitsikammamine |
description |
The Antarctic deep-sea sponge Latrunculia (Latrunculia) biformis Kirkpatrick, 1908 (Class Demospongiae Sollas, Order Poecilosclerida Topsent, Latrunculiidae Topsent) was selected for chemical analyses due to its potent anticancer activity. Metabolomic analysis of its crude extract by HRMS/MS-based molecular networking showed the presence of several clusters of pyrroloiminoquinone alkaloids, i.e., discorhabdin and epinardin-type brominated pyridopyrroloquinolines and tsitsikammamines, the non-brominated bis-pyrroloiminoquinones. Molecular networking approach combined with a bioactivity-guided isolation led to the targeted isolation of the known pyrroloiminoquinone tsitsikammamine A (1) and its new analog 16,17-dehydrotsitsikammamine A (2). The chemical structures of the compounds 1 and 2 were elucidated by spectroscopic analysis (one-dimensional (1D) and two-dimensional (2D) NMR, HR-ESIMS). Due to minute amounts, molecular modeling and docking was used to assess potential affinities to potential targets of the isolated compounds, including DNA intercalation, topoisomerase I-II, and indoleamine 2,3-dioxygenase enzymes. Tsitsikammamines represent a small class of pyrroloiminoquinone alkaloids that have only previously been reported from the South African sponge genus Tsitsikamma Samaai & Kelly and an Australian species of the sponge genus Zyzzya de Laubenfels. This is the first report of tsitsikammamines from the genus Latrunculia du Bocage and the successful application of molecular networking in the identification of comprehensive chemical inventory of L.biformis followed by targeted isolation of new molecules. This study highlights the high productivity of secondary metabolites of Latrunculia sponges and may shed new light on their biosynthetic origin and chemotaxonomy. |
format |
Article in Journal/Newspaper |
author |
Li, Fengjie Janussen, Dorte Peifer, Christian Pérez-Victoria, Ignacio Tasdemir, Deniz |
author_facet |
Li, Fengjie Janussen, Dorte Peifer, Christian Pérez-Victoria, Ignacio Tasdemir, Deniz |
author_sort |
Li, Fengjie |
title |
Targeted Isolation of Tsitsikammamines from the Antarctic Deep-Sea Sponge Latrunculia biformis by Molecular Networking and Anticancer Activity |
title_short |
Targeted Isolation of Tsitsikammamines from the Antarctic Deep-Sea Sponge Latrunculia biformis by Molecular Networking and Anticancer Activity |
title_full |
Targeted Isolation of Tsitsikammamines from the Antarctic Deep-Sea Sponge Latrunculia biformis by Molecular Networking and Anticancer Activity |
title_fullStr |
Targeted Isolation of Tsitsikammamines from the Antarctic Deep-Sea Sponge Latrunculia biformis by Molecular Networking and Anticancer Activity |
title_full_unstemmed |
Targeted Isolation of Tsitsikammamines from the Antarctic Deep-Sea Sponge Latrunculia biformis by Molecular Networking and Anticancer Activity |
title_sort |
targeted isolation of tsitsikammamines from the antarctic deep-sea sponge latrunculia biformis by molecular networking and anticancer activity |
publishDate |
2018 |
url |
https://doi.org/10.3390/md16080268 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2019-00169-2 https://macau.uni-kiel.de/receive/macau_mods_00000147 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001092/marinedrugs-16-00268-v2.pdf |
geographic |
Antarctic The Antarctic |
geographic_facet |
Antarctic The Antarctic |
genre |
Antarc* Antarctic Antarctica |
genre_facet |
Antarc* Antarctic Antarctica |
op_relation |
Marine drugs -- Mar Drugs -- 1660-3397 -- 1660-3397 https://doi.org/10.3390/md16080268 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2019-00169-2 https://macau.uni-kiel.de/receive/macau_mods_00000147 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001092/marinedrugs-16-00268-v2.pdf |
op_rights |
https://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.3390/md16080268 |
container_title |
Marine Drugs |
container_volume |
16 |
container_issue |
8 |
container_start_page |
268 |
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1802638194201591808 |