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. T...
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ftdoajarticles:oai:doaj.org/article:a292ef5f7e984afda7ca70f7c940b347 2023-05-15T18:42:37+02:00 Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina Marte Jenssen Venke Kristoffersen Kumar Motiram-Corral Johan Isaksson Teppo Rämä Jeanette H. Andersen Espen H. Hansen Kine Østnes Hansen 2021-12-01T00:00:00Z https://doi.org/10.3390/molecules26247560 https://doaj.org/article/a292ef5f7e984afda7ca70f7c940b347 EN eng MDPI AG https://www.mdpi.com/1420-3049/26/24/7560 https://doaj.org/toc/1420-3049 doi:10.3390/molecules26247560 1420-3049 https://doaj.org/article/a292ef5f7e984afda7ca70f7c940b347 Molecules, Vol 26, Iss 7560, p 7560 (2021) Digitatispora marina marine fungus sensu stricto Basidiomycota bioprospecting chlorinated secondary metabolite natural products Organic chemistry QD241-441 article 2021 ftdoajarticles https://doi.org/10.3390/molecules26247560 2022-12-31T11:03:00Z 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. Article in Journal/Newspaper Vannøya Directory of Open Access Journals: DOAJ Articles Norway Vannøya ENVELOPE(19.701,19.701,70.182,70.182) Molecules 26 24 7560 |
institution |
Open Polar |
collection |
Directory of Open Access Journals: DOAJ Articles |
op_collection_id |
ftdoajarticles |
language |
English |
topic |
Digitatispora marina marine fungus sensu stricto Basidiomycota bioprospecting chlorinated secondary metabolite natural products Organic chemistry QD241-441 |
spellingShingle |
Digitatispora marina marine fungus sensu stricto Basidiomycota bioprospecting chlorinated secondary metabolite natural products Organic chemistry QD241-441 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 Digitatispora marina |
topic_facet |
Digitatispora marina marine fungus sensu stricto Basidiomycota bioprospecting chlorinated secondary metabolite natural products Organic chemistry QD241-441 |
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. |
format |
Article in Journal/Newspaper |
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 |
title |
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_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_sort |
chlovalicin b, a chlorinated sesquiterpene isolated from the marine mushroom digitatispora marina |
publisher |
MDPI AG |
publishDate |
2021 |
url |
https://doi.org/10.3390/molecules26247560 https://doaj.org/article/a292ef5f7e984afda7ca70f7c940b347 |
long_lat |
ENVELOPE(19.701,19.701,70.182,70.182) |
geographic |
Norway Vannøya |
geographic_facet |
Norway Vannøya |
genre |
Vannøya |
genre_facet |
Vannøya |
op_source |
Molecules, Vol 26, Iss 7560, p 7560 (2021) |
op_relation |
https://www.mdpi.com/1420-3049/26/24/7560 https://doaj.org/toc/1420-3049 doi:10.3390/molecules26247560 1420-3049 https://doaj.org/article/a292ef5f7e984afda7ca70f7c940b347 |
op_doi |
https://doi.org/10.3390/molecules26247560 |
container_title |
Molecules |
container_volume |
26 |
container_issue |
24 |
container_start_page |
7560 |
_version_ |
1766232333104447488 |