Beauvericin K, a New Antifungal Beauvericin Analogue from a Marine-derived <i>Fusarium</i> sp

Xu, Xiuli; Zhao, Shujiang; Yu, Ying; Chen, Zhengkun; Shen, Hui‐Hui; Zhou, Li

doi:10.1177/1934578x1601101213

Cited by 6 publications

(5 citation statements)

References 7 publications

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“…These precursor ions demonstrated similar fragmentations, due to the formation of the product ions at m/z 362, 262, and 134, along with consecutive neutral losses of 161 Da and 100 Da. As an illustration, the precursor ion at m/z 750 generated sequential neutral losses of 161, 100, and 127 Da; the neutral loss of 127 Da suggests that this ion contains an N-leucine/isoleucine unit in place of a phenylalanine unit ( Xu et al, 2016 ). The annotation derived from structure-based propagation for the other ions implies that the modification occurs at the amino acid unit, as indicated by the observed mass differences of 128, 141 and 157 Da.…”

Section: Resultsmentioning

confidence: 99%

Application of feature-based molecular networking and MassQL for the MS/MS fragmentation study of depsipeptides

Selegato,

Zanatta,

Pilon

et al. 2023

Front. Mol. Biosci.

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The Feature-based Molecular Networking (FBMN) is a well-known approach for mapping and identifying structures and analogues. However, in the absence of prior knowledge about the molecular class, assessing specific fragments and clusters requires time-consuming manual validation. This study demonstrates that combining FBMN and Mass Spec Query Language (MassQL) is an effective strategy for accelerating the decoding mass fragmentation pathways and identifying molecules with comparable fragmentation patterns, such as beauvericin and its analogues. To accomplish this objective, a spectral similarity network was built from ESI-MS/MS experiments of Fusarium oxysporum at various collision energies (CIDs) and paired with a MassQL search query for conserved beauvericin ions. FBMN analysis revealed that sodiated and protonated ions clustered differently, with sodiated adducts needing more collision energy and exhibiting a distinct fragmentation pattern. Based on this distinction, two sets of particular fragments were discovered for the identification of these hexadepsipeptides: ([M + H]+) m/z 134, 244, 262, and 362 and ([M + Na]+) m/z 266, 284 and 384. By using these fragments, MassQL accurately found other analogues of the same molecular class and annotated beauvericins that were not classified by FBMN alone. Furthermore, FBMN analysis of sodiated beauvericins at 70 eV revealed subclasses with distinct amino acid residues, allowing distinction between beauvericins (beauvericin and beauvericin D) and two previously unknown structural isomers with an unusual methionine sulfoxide residue. In summary, our integrated method revealed correlations between adduct types and fragmentation patterns, facilitated the detection of beauvericin clusters, including known and novel analogues, and allowed for the differentiation between structural isomers.

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Section: Resultsmentioning

confidence: 99%

Application of feature-based molecular networking and MassQL for the MS/MS fragmentation study of depsipeptides

Selegato,

Zanatta,

Pilon

et al. 2023

Front. Mol. Biosci.

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“…Fusolanones B, isolated from F. solani HDN15–410, was a novel γ‐pyrometer derivative, which exhibited significant activity on Vibrio parahaemolyticus [29]. A novel compound, beauvericin K, which derived from a marine strain Fusarium sp., possessed significant inhibition against the yeast C. albicans [30]. As the research goes further, metabolites with enzyme inhibitory activity in Fusarium sp.…”

Section: Discussionmentioning

confidence: 99%

α‐Glucosidase inhibitory effect of an anthraquinonoid produced by Fusarium incarnatum GDZZ‐G2

Fan

et al. 2022

J Basic Microbiol

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α-Glucosidase is the key enzyme on carbohydrate metabolism, and its bioactive inhibitors are supposed to be an effective therapeutic for type 2 diabetes mellitus. During our continuing study for discovering α-glucosidase inhibitors, a fungus GDZZ-G2 which is derived from a medicinal plant Callicarpa kwangtungensis Chun, exhibited significant inhibition on α-glucosidase. The strain was identified as Fusarium incarnatum by morphological and molecular methods. Further bioassay-guided fractionation result in six known secondary metabolites (1-6). All the compounds except 4 were isolated from F. incarnatum for the first time. Among them, an anthraquinonoid (S)-1,3,6-trihydroxy-7-(1-hydroxyethyl)anthracene-9,10dione (compound 1) exhibited strong inhibitory effect against α-glucosidase (IC 50 = 77.67 ± 0.67 μΜ), compared with acarbose (IC 50 = 711.8 ± 5 μΜ). An enzyme kinetics analysis revealed that compound 1 was an uncompetitive inhibitor. Besides, docking simulations predicted that compound 1 inhibited α-glucosidase substrate complex by binding Gln322, Gly306, Thr307, and Ser329 through hydrogen-bond interactions. Our findings suggested that compound 1 can be considered a lead compound for further modifications and the development of a new effective drug candidate in the treatment of type 2 diabetes mellitus.

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“…FH-146 displayed moderate activity against A. clavatus F318a with a MIC value of 6.25 µg/mL [47]. Six cyclic depsipeptides 89-94 had been isolated from several Fusarium strains and found to have significant inhibitory activities against pathogenic fungi, such as C. albicans [48], C. glabrata, C. krusei, V. ceratosperma, and A. fumigates [49]. Cyclosporin A (91) has long been recognized as an immunosuppressant agent and could inhibit the growth of sensitive fungi after their germination [50,51].…”

Section: Antifungal Secondary Metabolitesmentioning

confidence: 99%

“…Among these Fusarium-derived 1,4-naphthoquinone analogs (109-115), compound 109 showed potent anti-Gram-positive bacteria activity against B. cereus and S. pyogenes with MIC of <1 µg/mL and anti-C. albicans activity with IC 50 (the half maximal inhibitory concentration) of 6.16 µg/mL [14], and 110-115 demonstrated moderate inhibitory effects on S. aureus, C. albicans, and B. subtilis [61]. Bikaverin (116) was found to have anti-E. coli and antifungal (P. notatum, Alternaria humicola, and A. flavus) activity [48,62,63]. Lateropyrone (117) was the same SM as F. acuminatum, F. lateritium, and F. tricinctum and displayed good antibacterial activity against B. subtilis, S. aureus, S. pneumoniae, methicillin-resistant S. aureus, Mycobacterium tuberculosis, and vancomycin-resistant of E. faecalis and significant inhibitory activity towards the growth of C. albicans [64][65][66][67].…”

Section: Both Antibacterial and Antifungal Secondary Metabolitesmentioning

confidence: 99%

Fusarium-Derived Secondary Metabolites with Antimicrobial Effects

Huang

Zhu

et al. 2023

Molecules

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Fungal microbes are important in the creation of new drugs, given their unique genetic and metabolic diversity. As one of the most commonly found fungi in nature, Fusarium spp. has been well regarded as a prolific source of secondary metabolites (SMs) with diverse chemical structures and a broad spectrum of biological properties. However, little information is available concerning their derived SMs with antimicrobial effects. By extensive literature search and data analysis, as many as 185 antimicrobial natural products as SMs had been discovered from Fusarium strains by the end of 2022. This review first provides a comprehensive analysis of these substances in terms of various antimicrobial effects, including antibacterial, antifungal, antiviral, and antiparasitic. Future prospects for the efficient discovery of new bioactive SMs from Fusarium strains are also proposed.

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Beauvericin K, a New Antifungal Beauvericin Analogue from a Marine-derived Fusarium sp

Cited by 6 publications

References 7 publications

Application of feature-based molecular networking and MassQL for the MS/MS fragmentation study of depsipeptides

Application of feature-based molecular networking and MassQL for the MS/MS fragmentation study of depsipeptides

α‐Glucosidase inhibitory effect of an anthraquinonoid produced by Fusarium incarnatum GDZZ‐G2

Fusarium-Derived Secondary Metabolites with Antimicrobial Effects

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