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Article

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

by
Marte Jenssen
1,
Venke Kristoffersen
1,
Kumar Motiram-Corral
2,
Johan Isaksson
3,
Teppo Rämä
1,
Jeanette H. Andersen
1,
Espen H. Hansen
1 and
Kine Østnes Hansen
1,*
1
Marbio, Norwegian College of Fishery Science, UiT—The Arctic University of Norway, N-9037 Tromsø, Norway
2
Servei de Ressonància Magnètica Nuclear, Universitat Autònoma de Barcelona, Bellaterra, E-08193 Barcelona, Spain
3
Department of Chemistry, UiT—The Arctic University of Norway, N-9037 Tromsø, Norway
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(24), 7560; https://doi.org/10.3390/molecules26247560
Submission received: 16 November 2021 / Revised: 7 December 2021 / Accepted: 9 December 2021 / Published: 13 December 2021
(This article belongs to the Special Issue Microbial Natural Products 2022)
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Abstract

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.
Keywords: Digitatispora marina; marine fungus sensu stricto; Basidiomycota; bioprospecting; chlorinated secondary metabolite; natural products Digitatispora marina; marine fungus sensu stricto; Basidiomycota; bioprospecting; chlorinated secondary metabolite; natural products

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MDPI and ACS Style

Jenssen, M.; Kristoffersen, V.; Motiram-Corral, K.; Isaksson, J.; Rämä, T.; Andersen, J.H.; Hansen, E.H.; Hansen, K.Ø. Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina. Molecules 2021, 26, 7560. https://doi.org/10.3390/molecules26247560

AMA Style

Jenssen M, Kristoffersen V, Motiram-Corral K, Isaksson J, Rämä T, Andersen JH, Hansen EH, Hansen KØ. Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina. Molecules. 2021; 26(24):7560. https://doi.org/10.3390/molecules26247560

Chicago/Turabian Style

Jenssen, Marte, Venke Kristoffersen, Kumar Motiram-Corral, Johan Isaksson, Teppo Rämä, Jeanette H. Andersen, Espen H. Hansen, and Kine Østnes Hansen. 2021. "Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina" Molecules 26, no. 24: 7560. https://doi.org/10.3390/molecules26247560

APA Style

Jenssen, M., Kristoffersen, V., Motiram-Corral, K., Isaksson, J., Rämä, T., Andersen, J. H., Hansen, E. H., & Hansen, K. Ø. (2021). Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina. Molecules, 26(24), 7560. https://doi.org/10.3390/molecules26247560

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