Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom <i>Digitatispora marina</i>
As part of our search for bioactive metabolites from understudied marine microorganisms, the new chlorinated metabolite chlovalicin B (<b>1</b>) was isolated from liquid cultures of the marine basidiomycete <i>Digitatispora marina</i>, which was collected and isolated from dr...
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MDPI AG
2021-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/24/7560 |
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| author | Marte Jenssen Venke Kristoffersen Kumar Motiram-Corral Johan Isaksson Teppo Rämä Jeanette H. Andersen Espen H. Hansen Kine Østnes Hansen |
| author_facet | Marte Jenssen Venke Kristoffersen Kumar Motiram-Corral Johan Isaksson Teppo Rämä Jeanette H. Andersen Espen H. Hansen Kine Østnes Hansen |
| author_sort | Marte Jenssen |
| collection | DOAJ |
| description | As part of our search for bioactive metabolites from understudied marine microorganisms, the new chlorinated metabolite chlovalicin B (<b>1</b>) was isolated from liquid cultures of the marine basidiomycete <i>Digitatispora marina</i>, 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 <b>1</b> shares its molecular scaffold with a previously isolated compound, chlovalicin. This represents the first compound isolated from the <i>Digitatispora</i> genus, and the first reported fumagillin/ovalicin-like compound isolated from Basidiomycota. Compound <b>1</b> was evaluated for antibacterial activities against a panel of five bacteria, its ability to inhibit bacterial biofilm formation, for antifungal activity against <i>Candida albicans</i>, and for cytotoxic activities against malignant and non-malignant human cell lines. Compound <b>1</b> displayed weak cytotoxic activity against the human melanoma cell line A2058 (~50% survival at 50 µM). No activity was detected against biofilm formation or <i>C. albicans</i> 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. |
| first_indexed | 2024-03-10T03:29:30Z |
| format | Article |
| id | doaj.art-a292ef5f7e984afda7ca70f7c940b347 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:29:30Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a292ef5f7e984afda7ca70f7c940b3472023-11-23T09:45:54ZengMDPI AGMolecules1420-30492021-12-012624756010.3390/molecules26247560Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom <i>Digitatispora marina</i>Marte Jenssen0Venke Kristoffersen1Kumar Motiram-Corral2Johan Isaksson3Teppo Rämä4Jeanette H. Andersen5Espen H. Hansen6Kine Østnes Hansen7Marbio, Norwegian College of Fishery Science, UiT—The Arctic University of Norway, N-9037 Tromsø, NorwayMarbio, Norwegian College of Fishery Science, UiT—The Arctic University of Norway, N-9037 Tromsø, NorwayServei de Ressonància Magnètica Nuclear, Universitat Autònoma de Barcelona, Bellaterra, E-08193 Barcelona, SpainDepartment of Chemistry, UiT—The Arctic University of Norway, N-9037 Tromsø, NorwayMarbio, Norwegian College of Fishery Science, UiT—The Arctic University of Norway, N-9037 Tromsø, NorwayMarbio, Norwegian College of Fishery Science, UiT—The Arctic University of Norway, N-9037 Tromsø, NorwayMarbio, Norwegian College of Fishery Science, UiT—The Arctic University of Norway, N-9037 Tromsø, NorwayMarbio, Norwegian College of Fishery Science, UiT—The Arctic University of Norway, N-9037 Tromsø, NorwayAs part of our search for bioactive metabolites from understudied marine microorganisms, the new chlorinated metabolite chlovalicin B (<b>1</b>) was isolated from liquid cultures of the marine basidiomycete <i>Digitatispora marina</i>, 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 <b>1</b> shares its molecular scaffold with a previously isolated compound, chlovalicin. This represents the first compound isolated from the <i>Digitatispora</i> genus, and the first reported fumagillin/ovalicin-like compound isolated from Basidiomycota. Compound <b>1</b> was evaluated for antibacterial activities against a panel of five bacteria, its ability to inhibit bacterial biofilm formation, for antifungal activity against <i>Candida albicans</i>, and for cytotoxic activities against malignant and non-malignant human cell lines. Compound <b>1</b> displayed weak cytotoxic activity against the human melanoma cell line A2058 (~50% survival at 50 µM). No activity was detected against biofilm formation or <i>C. albicans</i> 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.https://www.mdpi.com/1420-3049/26/24/7560<i>Digitatispora marina</i>marine fungus <i>sensu stricto</i>Basidiomycotabioprospectingchlorinated secondary metabolitenatural products |
| spellingShingle | Marte Jenssen Venke Kristoffersen Kumar Motiram-Corral Johan Isaksson Teppo Rämä Jeanette H. Andersen Espen H. Hansen Kine Østnes Hansen Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom <i>Digitatispora marina</i> Molecules <i>Digitatispora marina</i> marine fungus <i>sensu stricto</i> Basidiomycota bioprospecting chlorinated secondary metabolite natural products |
| title | Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom <i>Digitatispora marina</i> |
| title_full | Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom <i>Digitatispora marina</i> |
| title_fullStr | Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom <i>Digitatispora marina</i> |
| title_full_unstemmed | Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom <i>Digitatispora marina</i> |
| title_short | Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom <i>Digitatispora marina</i> |
| title_sort | chlovalicin b a chlorinated sesquiterpene isolated from the marine mushroom i digitatispora marina i |
| topic | <i>Digitatispora marina</i> marine fungus <i>sensu stricto</i> Basidiomycota bioprospecting chlorinated secondary metabolite natural products |
| url | https://www.mdpi.com/1420-3049/26/24/7560 |
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