7b598b43000e2d32f7cc8a7dfdb32e46 molecules-26-07560.pdf 838491fe762b5ce91819cb40e053eb836be1941f molecules-26-07560.pdf 0bdd9c1d3211a96b0e3914d85c4a8357f6b025bf68b13a53f1506bed3b3cd20d molecules-26-07560.pdf Title: Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina Subject: 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 M). No activity was detected against biofilm formation or C. albicans at 50 M, or against bacterial growth at 100 M nor against the production of cytokines by the human acute monocytic leukemia cell line THP-1 at 50 M. Keywords: Digitatispora marina; marine fungus sensu stricto; Basidiomycota; bioprospecting; chlorinated secondary metabolite; natural products Author: Marte Jenssen, Venke Kristoffersen, Kumar Motiram-Corral, Johan Isaksson, Teppo Rämä, Jeanette H. Andersen, Espen H. Hansen and Kine Østnes Hansen Creator: LaTeX with hyperref Producer: pdfTeX-1.40.21 CreationDate: Thu Dec 16 02:44:24 2021 CET ModDate: Thu Dec 16 02:48:19 2021 CET Custom Metadata: no Metadata Stream: no Tagged: no UserProperties: no Suspects: no Form: none JavaScript: no Pages: 8 Encrypted: no Page size: 595.276 x 841.89 pts (A4) Page rot: 0 File size: 730132 bytes Optimized: no PDF version: 1.7 name type encoding emb sub uni object ID ------------------------------------ ----------------- ---------------- --- --- --- --------- TMQPBQ+VnURWPalladioL Type 1 Custom yes yes no 10 0 HIXHLH+EURM10 Type 1 Builtin yes yes no 15 0 DXWKSP+URWPalladioL-Ital Type 1 Custom yes yes no 19 0 DVWXXX+URWPalladioL-Bold Type 1 Custom yes yes no 24 0 YWIKUI+URWPalladioL-BoldItal Type 1 Custom yes yes no 28 0 RLVRKY+URWPalladioL-Roma Type 1 Custom yes yes no 32 0 PUSVWS+TimesNewRomanPS-BoldItalicMT Type 1C WinAnsi yes yes no 40 0 MCBCCI+SourceSansRoman-Regular Type 1C Custom yes yes no 62 0 MCBCCM+SourceSansRoman.613wght Type 1C Custom yes yes no 66 0 MCBCCO+SourceSansRoman-Bold Type 1C Custom yes yes no 70 0 VIWIOF+CMSY10 Type 1 Builtin yes yes no 82 0 GUUOCM+EURB10 Type 1 Builtin yes yes no 89 0 AENJOB+PalatinoLinotype-Bold CID TrueType Identity-H yes yes yes 104 0 AENJPC+PalatinoLinotype-Roman CID TrueType Identity-H yes yes yes 110 0 AENJPD+PalatinoLinotype-Italic CID TrueType Identity-H yes yes yes 116 0 AENKAD+PalatinoLinotype-Italic TrueType WinAnsi yes yes no 122 0 AENKAE+PalatinoLinotype-Bold TrueType WinAnsi yes yes no 125 0 AENKAF+PalatinoLinotype-Roman TrueType WinAnsi yes yes no 128 0 AENJOB+PalatinoLinotype-Bold CID TrueType Identity-H yes yes yes 147 0 AENJPC+PalatinoLinotype-Roman CID TrueType Identity-H yes yes yes 153 0 AENJPD+PalatinoLinotype-Italic CID TrueType Identity-H yes yes yes 159 0 AENKAD+PalatinoLinotype-Italic TrueType WinAnsi yes yes no 165 0 AENKAE+PalatinoLinotype-Bold TrueType WinAnsi yes yes no 168 0 AENKAF+PalatinoLinotype-Roman TrueType WinAnsi yes yes no 171 0 NUUXUW+VnURWPalladioL-Italic Type 1 Custom yes yes no 188 0 Jhove (Rel. 1.28.0, 2023-05-18) Date: 2026-02-12 03:09:05 CET RepresentationInformation: molecules-26-07560.pdf ReportingModule: PDF-hul, Rel. 1.12.4 (2023-03-16) LastModified: 2026-02-11 18:05:15 CET Size: 730132 Format: PDF Version: 1.7 Status: Well-Formed and valid SignatureMatches: PDF-hul MIMEtype: application/pdf PDFMetadata: Objects: 290 FreeObjects: 1 IncrementalUpdates: 0 DocumentCatalog: PageLayout: SinglePage PageMode: UseNone Outlines: Item: Title: Introduction Destination: section.1 Item: Title: Results and Discussion Destination: section.2 Item: Title: Materials and Methods Destination: section.3 Children: Item: Title: General Experimental Procedures Destination: subsection.3.1 Item: Title: Fungal Material and Cultivation Condition Destination: subsection.3.2 Item: Title: Extraction and Isolation Destination: subsection.3.3 Item: Title: Bioactivity Testing of Compound 1 Destination: subsection.3.4 Item: Title: Conclusions Destination: section.4 Item: Title: References Destination: section.4 Info: Title: Chlovalicin B, a Chlorinated Sesquiterpene Isolated from the Marine Mushroom Digitatispora marina Author: Marte Jenssen, Venke Kristoffersen, Kumar Motiram-Corral, Johan Isaksson, Teppo Rämä, Jeanette H. Andersen, Espen H. Hansen and Kine Østnes Hansen Subject: 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 M). No activity was detected against biofilm formation or C. albicans at 50 M, or against bacterial growth at 100 M nor against the production of cytokines by the human acute monocytic leukemia cell line THP-1 at 50 M. 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