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Nostotrebin 6 Related Cyclopentenediones and δ‑Lactones with Broad Activity Spectrum Isolated from the Cultivation Medium of the Cyanobacterium Nostoc sp. CBT1153

Cyanobacteria are an interesting source of biologically active natural products, especially chemically diverse and potent protease inhibitors. On our search for inhibitors of the trypanosomal cysteine protease rhodesain, we identified the homodimeric cyclopentenedione (CPD) nostotrebin 6 (1) and new...

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Published in:Journal of natural products (Washington, D.C.) D.C.), 2020-02, Vol.83 (2), p.392-400
Main Authors: Kossack, Ronja, Breinlinger, Steffen, Nguyen, Trang, Moschny, Julia, Straetener, Jan, Berscheid, Anne, Brötz-Oesterhelt, Heike, Enke, Heike, Schirmeister, Tanja, Niedermeyer, Timo H. J
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cited_by cdi_FETCH-LOGICAL-a348t-fc52efc8e8d1068eca33c417d85ee839e92c81b272f3a92d1443c799d14e24ab3
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creator Kossack, Ronja
Breinlinger, Steffen
Nguyen, Trang
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Schirmeister, Tanja
Niedermeyer, Timo H. J
description Cyanobacteria are an interesting source of biologically active natural products, especially chemically diverse and potent protease inhibitors. On our search for inhibitors of the trypanosomal cysteine protease rhodesain, we identified the homodimeric cyclopentenedione (CPD) nostotrebin 6 (1) and new related monomeric, dimeric, and higher oligomeric compounds as the active substances in the medium extract of Nostoc sp. CBT1153. The oligomeric compounds are composed of two core monomeric structures, a trisubstituted CPD or a trisubstituted unsaturated δ-lactone. Nostotrebin 6 thus far has been the only known cyanobacterial CPD. It has been found to be active in a broad variety of assays, indicating that it might be a pan-assay interference compound (PAIN). Thus, we compared the antibacterial and cytotoxic activities as well as the rhodesain inhibition of selected compounds. Because a compound with a δ-lactone instead of a CPD core structure was equally active as nostotrebin 6, the bioactivities of these compounds seem to be based on the phenolic substructures rather than the CPD moiety. While the dimers were roughly equally potent, the monomer displayed slightly weaker activity, suggesting that the compounds show unspecific activity depending upon the number of free phenolic hydroxy groups per molecule.
doi_str_mv 10.1021/acs.jnatprod.9b00885
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - isolation & purification
Culture Media
Cyclopentanes - chemistry
Cyclopentanes - isolation & purification
Lactones - chemistry
Molecular Structure
Nostoc - chemistry
Phenols - chemistry
title Nostotrebin 6 Related Cyclopentenediones and δ‑Lactones with Broad Activity Spectrum Isolated from the Cultivation Medium of the Cyanobacterium Nostoc sp. CBT1153
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