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Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina

As part of our search for bioactive metabolites from understudied marine microorganisms, the new chlorinated metabolite chlovalicin B (1) was isolated from liquid cultures of the marine basidiomycete Digitatispora marina, which was collected and isolated from driftwood found at Vannøya, Norway. The...

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Autores principales: Jenssen, Marte, Kristoffersen, Venke, Motiram-Corral, Kumar, Isaksson, Johan, Rämä, Teppo, Andersen, Jeanette H., Hansen, Espen H., Hansen, Kine Østnes
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8703342/
https://www.ncbi.nlm.nih.gov/pubmed/34946641
http://dx.doi.org/10.3390/molecules26247560
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author Jenssen, Marte
Kristoffersen, Venke
Motiram-Corral, Kumar
Isaksson, Johan
Rämä, Teppo
Andersen, Jeanette H.
Hansen, Espen H.
Hansen, Kine Østnes
author_facet Jenssen, Marte
Kristoffersen, Venke
Motiram-Corral, Kumar
Isaksson, Johan
Rämä, Teppo
Andersen, Jeanette H.
Hansen, Espen H.
Hansen, Kine Østnes
author_sort Jenssen, Marte
collection PubMed
description As part of our search for bioactive metabolites from understudied marine microorganisms, the new chlorinated metabolite chlovalicin B (1) was isolated from liquid cultures of the marine basidiomycete Digitatispora marina, which was collected and isolated from driftwood found at Vannøya, Norway. The structure of the novel compound was elucidated by spectroscopic methods including 1D and 2D NMR and analysis of HRMS data, revealing that 1 shares its molecular scaffold with a previously isolated compound, chlovalicin. This represents the first compound isolated from the Digitatispora genus, and the first reported fumagillin/ovalicin-like compound isolated from Basidiomycota. Compound 1 was evaluated for antibacterial activities against a panel of five bacteria, its ability to inhibit bacterial biofilm formation, for antifungal activity against Candida albicans, and for cytotoxic activities against malignant and non-malignant human cell lines. Compound 1 displayed weak cytotoxic activity against the human melanoma cell line A2058 (~50% survival at 50 µM). No activity was detected against biofilm formation or C. albicans at 50 µM, or against bacterial growth at 100 µM nor against the production of cytokines by the human acute monocytic leukemia cell line THP-1 at 50 µM.
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spelling pubmed-87033422021-12-25 Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina Jenssen, Marte Kristoffersen, Venke Motiram-Corral, Kumar Isaksson, Johan Rämä, Teppo Andersen, Jeanette H. Hansen, Espen H. Hansen, Kine Østnes Molecules Article As part of our search for bioactive metabolites from understudied marine microorganisms, the new chlorinated metabolite chlovalicin B (1) was isolated from liquid cultures of the marine basidiomycete Digitatispora marina, which was collected and isolated from driftwood found at Vannøya, Norway. The structure of the novel compound was elucidated by spectroscopic methods including 1D and 2D NMR and analysis of HRMS data, revealing that 1 shares its molecular scaffold with a previously isolated compound, chlovalicin. This represents the first compound isolated from the Digitatispora genus, and the first reported fumagillin/ovalicin-like compound isolated from Basidiomycota. Compound 1 was evaluated for antibacterial activities against a panel of five bacteria, its ability to inhibit bacterial biofilm formation, for antifungal activity against Candida albicans, and for cytotoxic activities against malignant and non-malignant human cell lines. Compound 1 displayed weak cytotoxic activity against the human melanoma cell line A2058 (~50% survival at 50 µM). No activity was detected against biofilm formation or C. albicans at 50 µM, or against bacterial growth at 100 µM nor against the production of cytokines by the human acute monocytic leukemia cell line THP-1 at 50 µM. MDPI 2021-12-13 /pmc/articles/PMC8703342/ /pubmed/34946641 http://dx.doi.org/10.3390/molecules26247560 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Jenssen, Marte
Kristoffersen, Venke
Motiram-Corral, Kumar
Isaksson, Johan
Rämä, Teppo
Andersen, Jeanette H.
Hansen, Espen H.
Hansen, Kine Østnes
Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina
title Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina
title_full Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina
title_fullStr Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina
title_full_unstemmed Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina
title_short Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina
title_sort chlovalicin b, a chlorinated sesquiterpene isolated from the marine mushroom digitatispora marina
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8703342/
https://www.ncbi.nlm.nih.gov/pubmed/34946641
http://dx.doi.org/10.3390/molecules26247560
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