Cytochalasans

Bräse, Stefan; Gläser, Franziska; Kramer, Carsten S.; Lindner, Stephanie; Linsenmeier, Anna M.; Masters, Kye-Simeon; Meister, Anne C.; Ruff, Bettina M.; Zhong, Sabilla

doi:10.1007/978-3-7091-1312-7_14

Cited by 4 publications

(2 citation statements)

References 56 publications

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“…The putatively identified compounds are of the subclass aspocalasin (Figure 4), a group of cytochalasins containing the 2‐methylpropyl group, which is constant in the substituted isoindoline ring 30 . Compounds ( 1 ) and ( 5 ) presented hits with the GNPS library, and compounds ( 2 ), ( 3 ), and ( 4 ) were annotated from the comparison of their MS/MS spectra with the spectra of public databases.…”

Section: Resultsmentioning

confidence: 99%

Ultra‐high‐performance liquid chromatography combined with electrospray ionization quadrupole time‐of‐flight mass spectrometry and molecular networking analysis to investigate the chemodiversity of bioactive extracts of Annona jahnii Saff. fungi from the Brazilian Amazon

Xavier

Odilair

Sousa

et al. 2022

Rapid Comm Mass Spectrometry

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Rationale Annona species are of interest for the isolation of bioactive molecules; however, studies of Annona jahnii Saff. are limited. The exploration of bioactive metabolites of endophytes isolated from this species is unprecedented and allows the preservation of the host plant, in addition to enabling the discovery of compounds with promising biological activities. Methods Ethyl acetate extracts from the cultured media of five fungi were obtained. The antioxidant capacity of the extracts was measured using the 1,1‐diphenyl‐2‐picrylhydrazyl free radical method. Antimicrobial activity was determined using the microdilution method in broth in 96‐well plates. The exploration of the metabolic profile of the extracts and dereplication of the compounds were performed using ultra‐high‐performance liquid chromatography/electrospray ionization/tandem mass spectrometry (UHPLC/ESI‐MS/MS) combined with analysis using molecular networking (MN). Results A total of 1818 MS features were detected in the five selected extracts, of which 39 compounds were putatively identified. The secondary metabolites with the highest abundance were alkaloids, naphthopyrons, and cytochalasins. Other secondary metabolites include fumonisins, coumarin, and a meroterpenoid. Most of these compounds are related to specific biological properties such as antioxidant, anti‐inflammatory, antimicrobial, antiviral, and antitumor activities. Extracts F398 and F403 showed inhibitory activity of the four pathogens tested. Extracts F475 and F506 did not inhibit the growth of Staphylococcus aureus, and F407 did not inhibit the growth of Escherichia coli in addition to having potent antioxidant activity, with IC50 values of 10 μg/mL or less. Conclusions The use of UHPLC/ESI‐MS/MS data combined with MN proved useful in the dereplication of bioactive molecules of complex extracts that are still unexplored. These initial investigations should significantly assist in further research and increase the efficiency and speed in the discovery of new sources of secondary metabolites and new natural products.

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Section: Resultsmentioning

confidence: 99%

Ultra‐high‐performance liquid chromatography combined with electrospray ionization quadrupole time‐of‐flight mass spectrometry and molecular networking analysis to investigate the chemodiversity of bioactive extracts of Annona jahnii Saff. fungi from the Brazilian Amazon

Xavier

Odilair

Sousa

et al. 2022

Rapid Comm Mass Spectrometry

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“…Due to the broad activity spectrum of cytochalasans, further fields of applications, e.g., as pharmaceutical drugs in the clinical context [ 35 ], are discussed in the literature. However, prior to developing cytochalasans for broad-spectrum biotechnological application, a comprehensive and holistic understanding of their complex activities is necessary to be able to mitigate the natural risks associated with the application of an actin cytoskeletal inhibitor, potentially impacting various essential cell biological processes [ 6 , 36 ]. A broad overview of such processes, associated sites of activity, and exemplary images demonstrating the consequences for the intracellular filamentous actin network upon cytochalasan treatment are given in Figure 1 .…”

Section: Introductionmentioning

confidence: 99%

Cytochalasans and Their Impact on Actin Filament Remodeling

et al. 2023

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The eukaryotic actin cytoskeleton comprises the protein itself in its monomeric and filamentous forms, G- and F-actin, as well as multiple interaction partners (actin-binding proteins, ABPs). This gives rise to a temporally and spatially controlled, dynamic network, eliciting a plethora of motility-associated processes. To interfere with the complex inter- and intracellular interactions the actin cytoskeleton confers, small molecular inhibitors have been used, foremost of all to study the relevance of actin filaments and their turnover for various cellular processes. The most prominent inhibitors act by, e.g., sequestering monomers or by interfering with the polymerization of new filaments and the elongation of existing filaments. Among these inhibitors used as tool compounds are the cytochalasans, fungal secondary metabolites known for decades and exploited for their F-actin polymerization inhibitory capabilities. In spite of their application as tool compounds for decades, comprehensive data are lacking that explain (i) how the structural deviances of the more than 400 cytochalasans described to date influence their bioactivity mechanistically and (ii) how the intricate network of ABPs reacts (or adapts) to cytochalasan binding. This review thus aims to summarize the information available concerning the structural features of cytochalasans and their influence on the described activities on cell morphology and actin cytoskeleton organization in eukaryotic cells.

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