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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Published in:Marine Drugs
Main Authors: li, Fengjie, Janussen, Dorte, Pfeifer, Christian, Pérez-Victoria, Ignacio, Tasdemir, Deniz
Language:English
Published: 2018
Subjects:
Online Access:https://repository.publisso.de/resource/frl:6425615
https://doi.org/10.3390/md16080268
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6117724/
https://www.mdpi.com/1660-3397/16/8/268#supplementary
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spelling ftleibnizopen:oai:oai.leibnizopen.de:1iaKVYsBBwLIz6xGOlPC 2023-11-12T04:06:36+01:00 Targeted Isolation of Tsitsikammamines from the Antarctic Deep-Sea Sponge Latrunculia biformis by Molecular Networking and Anticancer Activity li, Fengjie Janussen, Dorte Pfeifer, Christian Pérez-Victoria, Ignacio Tasdemir, Deniz 2018 https://repository.publisso.de/resource/frl:6425615 https://doi.org/10.3390/md16080268 https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6117724/ https://www.mdpi.com/1660-3397/16/8/268#supplementary eng eng https://creativecommons.org/licenses/by/4.0/ Marine drugs, 16(8):268 Antarctica molecular docking tsitsikammamine Latrunculia molecular networking deep-sea marine sponge 2018 ftleibnizopen https://doi.org/10.3390/md16080268 2023-10-22T23:10:26Z 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. Other/Unknown Material Antarc* Antarctic Antarctica Unknown Antarctic The Antarctic Marine Drugs 16 8 268
institution Open Polar
collection Unknown
op_collection_id ftleibnizopen
language English
topic Antarctica
molecular docking
tsitsikammamine
Latrunculia
molecular networking
deep-sea
marine sponge
spellingShingle Antarctica
molecular docking
tsitsikammamine
Latrunculia
molecular networking
deep-sea
marine sponge
li, Fengjie
Janussen, Dorte
Pfeifer, 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 Antarctica
molecular docking
tsitsikammamine
Latrunculia
molecular networking
deep-sea
marine sponge
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.
author li, Fengjie
Janussen, Dorte
Pfeifer, Christian
Pérez-Victoria, Ignacio
Tasdemir, Deniz
author_facet li, Fengjie
Janussen, Dorte
Pfeifer, 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://repository.publisso.de/resource/frl:6425615
https://doi.org/10.3390/md16080268
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6117724/
https://www.mdpi.com/1660-3397/16/8/268#supplementary
geographic Antarctic
The Antarctic
geographic_facet Antarctic
The Antarctic
genre Antarc*
Antarctic
Antarctica
genre_facet Antarc*
Antarctic
Antarctica
op_source Marine drugs, 16(8):268
op_rights https://creativecommons.org/licenses/by/4.0/
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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