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Article

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

1
The Graduate School, University of Santo Tomas, España Blvd., Manila 1015, Philippines
2
Laboratory for Organic Reactivity, Discovery and Synthesis (LORDS), Research Center for the Natural and Applied Sciences, University of Santo Tomas, España Blvd., Manila 1015, Philippines
3
Chemistry Department, College of Science and Mathematics, Mindanao State University–Iligan Institute of Technology, Tibanga, Iligan City 9200, Philippines
4
Department of Microbial Drugs, Helmholtz Centre for Infection Research and German Centre for Infection Research (DZIF), Partner Site Hannover/Braunschweig, Inhoffenstraße 7, 38124 Braunschweig, Germany
5
Department of Cell Biology, Helmholtz Centre for Infection Research (HZI), Inhoffenstraße 7, 38124 Braunschweig, Germany
6
Research Center for Chemistry, National Research and Innovation Agency (BRIN), Kawasan Puspitek, Serpong, Tangerang Selatan 15314, Indonesia
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Institut für Organische Chemie, Universität Regensburg, Universitätstrasse 31, 93053 Regensburg, Germany
8
Leibniz-Institute for Natural Product Research and Infection Biology, Hans Knöll Institute (HKI), 07745 Jena, Germany
9
Center of Excellence in Fungal Research, Mae Fah Luang University, Chiang Rai 57100, Thailand
10
Institute of Plant Protection, College of Agriculture, Engineering Research Center of Chinese Ministry of Education for Edible and Medicinal Fungi, Jilin Agricultural University, Changchun 130118, China
11
Institute of Microbiology, Technische Universität Braunschweig, Spielmannstraße 7, 38106 Braunschweig, Germany
*
Authors to whom correspondence should be addressed.
Academic Editor: Gary A. Strobel
J. Fungi 2022, 8(6), 560; https://doi.org/10.3390/jof8060560
Received: 27 April 2022 / Revised: 17 May 2022 / Accepted: 20 May 2022 / Published: 25 May 2022
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. View Full-Text
Keywords: Sparticola triseptata; structure elucidation; ECD–TDDFT; antiproliferative; cytotoxic; actin inhibitors Sparticola triseptata; structure elucidation; ECD–TDDFT; antiproliferative; cytotoxic; actin inhibitors
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MDPI and ACS Style

Garcia, K.Y.M.; Quimque, M.T.J.; Lambert, C.; Schmidt, K.; Primahana, G.; Stradal, T.E.B.; Ratzenböck, A.; Dahse, H.-M.; Phukhamsakda, C.; Stadler, M.; Surup, F.; Macabeo, A.P.G. Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation. J. Fungi 2022, 8, 560. https://doi.org/10.3390/jof8060560

AMA Style

Garcia KYM, Quimque MTJ, Lambert C, Schmidt K, Primahana G, Stradal TEB, Ratzenböck A, Dahse H-M, Phukhamsakda C, Stadler M, Surup F, Macabeo APG. Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation. Journal of Fungi. 2022; 8(6):560. https://doi.org/10.3390/jof8060560

Chicago/Turabian Style

Garcia, Katherine Yasmin M., Mark Tristan J. Quimque, Christopher Lambert, Katharina Schmidt, Gian Primahana, Theresia E. B. Stradal, Andreas Ratzenböck, Hans-Martin Dahse, Chayanard Phukhamsakda, Marc Stadler, Frank Surup, and Allan Patrick G. Macabeo. 2022. "Antiproliferative and Cytotoxic Cytochalasins from Sparticola triseptata Inhibit Actin Polymerization and Aggregation" Journal of Fungi 8, no. 6: 560. https://doi.org/10.3390/jof8060560

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