Cytochalasans produced by <i>Xylaria karyophthora</i> and their biological activities

Lambert, Christopher; Shao, Lulu; Zeng, Haoxuan; Surup, Frank; Saetang, Praphatsorn; Aime, M. Catherine; Husbands, Dillon R.; Rottner, Klemens; Stradal, Theresia E. B.; Stadler, Marc

doi:10.1080/00275514.2023.2188868

Cited by 7 publications

(10 citation statements)

References 37 publications

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“…Another recent study [ 79 ] reported that the methyl groups in a steric position planar to the six-ring in cytochalasin K Steyn ( 120 , named cytochalasin K in [ 79 ]; see Figure 10 ) were associated with a drastic decrease in activity. This pattern of decreased activity could not be confirmed for this specific configuration in a panel of recently reported cytochalasins sharing an epoxidated macrocyclic backbone ( 110 – 112 , 121 – 127 , see Figure 9 and Figure 11 ) isolated from cultures of Xylaria karyophthora [ 96 ]. However, the steric conformation of the hydroxyl groups attached to the six rings was shown to be important.…”

Section: Correlating Cytochalasan Chemodiversity With the Activity Sp...mentioning

confidence: 79%

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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Section: Correlating Cytochalasan Chemodiversity With the Activity Sp...mentioning

confidence: 79%

Cytochalasans and Their Impact on Actin Filament Remodeling

et al. 2023

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“…The antibiofilm activity was determined according to a literature method. 73 A 1 mL aliquot of P. aeruginosa (PA 14) was taken from −20 °C stock, incubated in 25 mL LB medium (Luria–Bertani Broth) in a 250 mL flask, and kept at 37 °C at 100 rpm overnight. The optical density at 600 nm (OD 600 ) of the culture solution was adjusted to match the turbidity of a 0.1 McFarland standard in M63 medium.…”

Section: Methodsmentioning

confidence: 99%

Silver Organometallics that are Highly Potent Thioredoxin and Glutathione Reductase Inhibitors: Exploring the Correlations of Solution Chemistry with the Strong Antibacterial Effects

Esarev,

Karge,

Zeng

et al. 2024

ACS Infect. Dis.

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The antibacterial activity of silver species is wellestablished; however, their mechanism of action has not been adequately explored. Furthermore, issues of low-molecular silver compounds with cytotoxicity, stability, and solubility hamper their progress to drug leads. We have investigated silver N-heterocyclic carbene (NHC) halido complexes [(NHC)AgX, X = Cl, Br, and I] as a promising new type of antibacterial silver organometallics. Spectroscopic studies and conductometry established a higher stability for the complexes with iodide ligands, and nephelometry indicated that the complexes could be administered in solutions with physiological chloride levels. The complexes showed a broad spectrum of strong activity against pathogenic Gram-negative bacteria. However, there was no significant activity against Gram-positive strains. Further studies clarified that tryptone and yeast extract, as components of the culture media, were responsible for this lack of activity. The reduction of biofilm formation and a strong inhibition of both glutathione and thioredoxin reductases with IC 50 values in the nanomolar range were confirmed for selected compounds. In addition to their improved physicochemical properties, the compounds with iodide ligands did not display cytotoxic effects, unlike the other silver complexes. In summary, silver NHC complexes with iodide secondary ligands represent a useful scaffold for nontoxic silver organometallics with improved physicochemical properties and a distinct mechanism of action that is based on inhibition of thioredoxin and glutathione reductases.

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“…WH2D4 ( Figure 4 ) [ 41 ]. One new compound karyochalasin A ( 138 ) was isolated from the fungus X. karyophthora [ 42 ]. Six new cytochalasins, including curtachalasins X1-X6 ( 139 – 144 ), were obtained from the plant Solanum tuberosum -derived fungus Xylaria curta E10.…”

Section: Structural and Biological Activity Studiesmentioning

confidence: 99%

Structures and Biological Activities of Secondary Metabolites from Xylaria spp.

Chen,

Yu,

Chen

et al. 2024

JoF

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The fungus genus Xylaria is an important source of drug discoveries in scientific fields and in the pharmaceutical industry due to its potential to produce a variety of structured novel and bioactive secondary metabolites. This review prioritizes the structures of the secondary metabolites of Xylaria spp. from 1994 to January 2024 and their relevant biological activities. A total of 445 new compounds, including terpenoids, nitrogen-containing compounds, polyketides, lactones, and other classes, are presented in this review. Remarkably, among these compounds, 177 compounds show various biological activities, including cytotoxic, antimicrobial, anti-inflammatory, antifungal, immunosuppressive, and enzyme-inhibitory activities. This paper will guide further investigations into the structures of novel and potent active natural products derived from Xylaria and their potential contributions to the future development of new natural drug products in the agricultural and medicinal fields.

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Cytochalasans produced by Xylaria karyophthora and their biological activities

Cited by 7 publications

References 37 publications

Cytochalasans and Their Impact on Actin Filament Remodeling

Cytochalasans and Their Impact on Actin Filament Remodeling

Silver Organometallics that are Highly Potent Thioredoxin and Glutathione Reductase Inhibitors: Exploring the Correlations of Solution Chemistry with the Strong Antibacterial Effects

Structures and Biological Activities of Secondary Metabolites from Xylaria spp.

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