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Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation

Laying the groundwork on preliminary structure–activity relationship study relating to the disruptive activity of cytochalasan derivatives on mammalian cell actin cytoskeleton, we furthered our study on the cytochalasans of the Dothideomycetes fungus, Sparticola triseptata. A new cytochalasan analog...

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Autores principales: Garcia, Katherine Yasmin M., Quimque, Mark Tristan J., Lambert, Christopher, Schmidt, Katharina, Primahana, Gian, Stradal, Theresia E. B., Ratzenböck, Andreas, Dahse, Hans-Martin, Phukhamsakda, Chayanard, Stadler, Marc, Surup, Frank, Macabeo, Allan Patrick G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9225350/
https://www.ncbi.nlm.nih.gov/pubmed/35736043
http://dx.doi.org/10.3390/jof8060560
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author Garcia, Katherine Yasmin M.
Quimque, Mark Tristan J.
Lambert, Christopher
Schmidt, Katharina
Primahana, Gian
Stradal, Theresia E. B.
Ratzenböck, Andreas
Dahse, Hans-Martin
Phukhamsakda, Chayanard
Stadler, Marc
Surup, Frank
Macabeo, Allan Patrick G.
author_facet Garcia, Katherine Yasmin M.
Quimque, Mark Tristan J.
Lambert, Christopher
Schmidt, Katharina
Primahana, Gian
Stradal, Theresia E. B.
Ratzenböck, Andreas
Dahse, Hans-Martin
Phukhamsakda, Chayanard
Stadler, Marc
Surup, Frank
Macabeo, Allan Patrick G.
author_sort Garcia, Katherine Yasmin M.
collection PubMed
description Laying the groundwork on preliminary structure–activity relationship study relating to the disruptive activity of cytochalasan derivatives on mammalian cell actin cytoskeleton, we furthered our study on the cytochalasans of the Dothideomycetes fungus, Sparticola triseptata. A new cytochalasan analog triseptatin (1), along with the previously described cytochalasans deoxaphomin B (2) and cytochalasin B (3), and polyketide derivatives cis-4-hydroxy-6-deoxyscytalone (4) and 6-hydroxymellein (5) were isolated from the rice culture of S. triseptata. The structure of 1 was elucidated through NMR spectroscopic analysis and high-resolution mass spectrometry (HR-ESI-MS). The relative and absolute configurations were established through analysis of NOESY spectroscopic data and later correlated with experimental electronic circular dichroism and time-dependent density functional theory (ECD–TDDFT) computational analysis. Compounds 1 and 2 showed cytotoxic activities against seven mammalian cell lines (L929, KB3.1, MCF-7, A549, PC-3, SKOV-3, and A431) and antiproliferative effects against the myeloid leukemia K-562 cancer cell line. Both 1 and 2 were shown to possess properties inhibiting the F-actin network, prompting further hypotheses that should to be tested in the future to enable a well-resolved concept of the structural implications determining the bioactivity of the cytochalasin backbone against F-actin.
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spelling pubmed-92253502022-06-24 Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation Garcia, Katherine Yasmin M. Quimque, Mark Tristan J. Lambert, Christopher Schmidt, Katharina Primahana, Gian Stradal, Theresia E. B. Ratzenböck, Andreas Dahse, Hans-Martin Phukhamsakda, Chayanard Stadler, Marc Surup, Frank Macabeo, Allan Patrick G. J Fungi (Basel) Article Laying the groundwork on preliminary structure–activity relationship study relating to the disruptive activity of cytochalasan derivatives on mammalian cell actin cytoskeleton, we furthered our study on the cytochalasans of the Dothideomycetes fungus, Sparticola triseptata. A new cytochalasan analog triseptatin (1), along with the previously described cytochalasans deoxaphomin B (2) and cytochalasin B (3), and polyketide derivatives cis-4-hydroxy-6-deoxyscytalone (4) and 6-hydroxymellein (5) were isolated from the rice culture of S. triseptata. The structure of 1 was elucidated through NMR spectroscopic analysis and high-resolution mass spectrometry (HR-ESI-MS). The relative and absolute configurations were established through analysis of NOESY spectroscopic data and later correlated with experimental electronic circular dichroism and time-dependent density functional theory (ECD–TDDFT) computational analysis. Compounds 1 and 2 showed cytotoxic activities against seven mammalian cell lines (L929, KB3.1, MCF-7, A549, PC-3, SKOV-3, and A431) and antiproliferative effects against the myeloid leukemia K-562 cancer cell line. Both 1 and 2 were shown to possess properties inhibiting the F-actin network, prompting further hypotheses that should to be tested in the future to enable a well-resolved concept of the structural implications determining the bioactivity of the cytochalasin backbone against F-actin. MDPI 2022-05-25 /pmc/articles/PMC9225350/ /pubmed/35736043 http://dx.doi.org/10.3390/jof8060560 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Garcia, Katherine Yasmin M.
Quimque, Mark Tristan J.
Lambert, Christopher
Schmidt, Katharina
Primahana, Gian
Stradal, Theresia E. B.
Ratzenböck, Andreas
Dahse, Hans-Martin
Phukhamsakda, Chayanard
Stadler, Marc
Surup, Frank
Macabeo, Allan Patrick G.
Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation
title Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation
title_full Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation
title_fullStr Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation
title_full_unstemmed Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation
title_short Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation
title_sort antiproliferative and cytotoxic cytochalasins from sparticola triseptata inhibit actin polymerization and aggregation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9225350/
https://www.ncbi.nlm.nih.gov/pubmed/35736043
http://dx.doi.org/10.3390/jof8060560
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