Sequencing of new beauverolides by high‐performance liquid chromatography and mass spectrometry

Kuzma, Marek; Jegorov, Alexandr; Kačer, Petr; Havlı́ček, Vladimı́r

doi:10.1002/jms.213

Cited by 31 publications

(17 citation statements)

References 24 publications

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“…are cyclic tetradepsipeptides containing C 9 - or C 11 -β-hydroxy acid residues [32] (Figure 4a). More than twenty different beauverolides have been identified, and sequencing of beauverolides by tandem mass spectrometry has been well described [32], [33]. The product ion mass spectra we obtained in this study were virtually identical to those in the literature.…”

Section: Resultsmentioning

confidence: 99%

Metabolomics Reveals the Heterogeneous Secretome of Two Entomopathogenic Fungi to Ex Vivo Cultured Insect Tissues

et al. 2013

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Fungal entomopathogens rely on cellular heterogeneity during the different stages of insect host infection. Their pathogenicity is exhibited through the secretion of secondary metabolites, which implies that the infection life history of this group of environmentally important fungi can be revealed using metabolomics. Here metabolomic analysis in combination with ex vivo insect tissue culturing shows that two generalist isolates of the genus Metarhizium and Beauveria, commonly used as biological pesticides, employ significantly different arrays of secondary metabolites during infectious and saprophytic growth. It also reveals that both fungi exhibit tissue specific strategies by a distinguishable metabolite secretion on the insect tissues tested in this study. In addition to showing the important heterogeneous nature of these two entomopathogens, this study also resulted in the discovery of several novel destruxins and beauverolides that have not been described before, most likely because previous surveys did not use insect tissues as a culturing system. While Beauveria secreted these cyclic depsipeptides when encountering live insect tissues, Metarhizium employed them primarily on dead tissue. This implies that, while these fungi employ comparable strategies when it comes to entomopathogenesis, there are most certainly significant differences at the molecular level that deserve to be studied.

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Section: Resultsmentioning

confidence: 99%

Metabolomics Reveals the Heterogeneous Secretome of Two Entomopathogenic Fungi to Ex Vivo Cultured Insect Tissues

et al. 2013

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“…184 In distinct cases, the cyclopeptide ring opening is a selective process resulting in simple product ion mass spectra. 126,152 In the smallest beauverolide described so far and produced by Paecilomyces fumosoroseus, the backbone is specifically opened between C9-ˇ-hydroxy-and Lxx aminoacid residue. The corresponding gross cyclopeptide sequence can consequently be determined (Fig.…”

Section: Mass Spectrometry Of Cyclic Peptidesmentioning

confidence: 99%

Nonribosomal cyclic peptides: specific markers of fungal infections

Jegorov¹,

Hajdúch

Šulc

et al. 2006

J. Mass Spectrom.

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Some cyclic peptides and depsipeptides are synthesized in microorganisms by large multienzymes called nonribosomal peptide synthetases. The structures of peptide products originating in this way are complex and diverse and are microorganism-specific. This work proposes the use of fungal cyclic peptides and depsipeptides as extremely specific markers of fungal infections. Since a reliable molecular tool for diagnosing fungal infections at an early stage is still missing, we present mass spectrometry as a new, modern, broadband (with respect to fungal strain) and specific tool for clinical mycologists. More than 40 different fungal species can be rapidly characterized according to specific families of cyclic peptides, and in some cases, a particular fungal strain can be identified on the basis of its cyclopeptide profile. This paper is also aimed at initiating discussion on the biological role of these secondary metabolites, especially of those synthesized by medically important strains. Proven cytotoxic, anti-inflammatory or immunosuppressive activities of some cyclic peptides indicate that these molecules may contribute to the synergistic array of fungal virulence factors and support microbial invasion during fungal infection. In addition to an overview on recent mass spectrometric protocols for cyclic peptide sequencing, the structures of new peptides from Paecilomyces and Pseudallescheria are presented.

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“…6 Species of entomopathogenic fungi have been described as producers of secondary metabolites, including bioactive non-ribosomal peptides and polyketides. 7 B. bassiana produces the cyclooligomer nonribosomal depsipeptides beauvericins and bassianolide, 8,9 beauveriolides, 10 D, E and F. 25 Bassianolide is another cyclooctadepsipeptide metabolite produced B. bassiana and Lecanicillium lecanii. 9 It is toxic to insects and probably also acts as an ionophore, such as other cyclodepsipeptides.…”

Section: Introductionmentioning

confidence: 99%

“…6 Species of entomopathogenic fungi have been described as producers of secondary metabolites, including bioactive non-ribosomal peptides and polyketides. 7 B. bassiana produces the cyclooligomer nonribosomal depsipeptides beauvericins and bassianolide, 8,9 beauveriolides, 10 tenellin, bassianin, 11 pyridovericin, pyridomacrolidin, 12 oosporein 13 and bassiacridin. 14 In special, beauvericin is an ionophoric cyclodepsipeptide detected in several fungi, mainly Beauveria, Paecilomyces and Fusarium species.…”

Section: Introductionmentioning

confidence: 99%

Larvicidal Activity of Beauveria bassiana Extracts against Aedes aegypti and Identification of Beauvericins

Daniel

Silva

Nakagawa

et al. 2016

J. Braz. Chem. Soc.

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Beauveria bassiana is an entomopathogenic fungus that has been well known for its capacity to act as biopesticide on various disease vectors. The analysis of organic extracts of strains CG71 and UNI40 led to identification of cyclodepsipeptides beauvericin, beauvericin A or F, beauvericin E and bassianolide by ultra-high pressure liquid chromatography-high resolution mass spectrometry in tandem mode (UHPLC-HRMS/MS). The larvicidal activity on 3 rd instar of Aedes aegypti revealed LC 50 0.9887 and 0.4653 ppm in 24 and 48 hours (CG71 methanolic extract), LC 50 0.7834 ppm in 48 hours (CG71 ethyl acetate), LC 50 0.7834 and 1.8149 ppm (UNI 40 for ethyl acetate and methanolic extracts, respectively) in 48 hours. These findings highlight the potential of B. bassiana metabolites for controlling the vector of Dengue and Zika diseases. Keywords: cyclohexadepsipeptides, Dengue, Zika, beauvericins, UHPLC-HRMS/MS IntroductionThe entomopathogenic Beauveria bassiana has a broad host range naturally attacking insects and variety of arthropod species. [1][2][3] Due to this ability, it is used as a biopesticide agent on diverse disease vectors, including crop pests, ticks and mosquitoes. 4,5 The attack on insect cuticle occurs after hyphae of B. bassiana penetrate the insect integument by enzymatic action. 6 Species of entomopathogenic fungi have been described as producers of secondary metabolites, including bioactive non-ribosomal peptides and polyketides. 7 B. bassiana produces the cyclooligomer nonribosomal depsipeptides beauvericins and bassianolide, 8,9 beauveriolides, 10 D, E and F. 25 Bassianolide is another cyclooctadepsipeptide metabolite produced B. bassiana and Lecanicillium lecanii. 9 It is toxic to insects and probably also acts as an ionophore, such as other cyclodepsipeptides. 15 The structural diversity of metabolites from entomopathogenic fungi, associated with diverse biological activities, stimulates the research by on bioactive fungal extracts for controlling insect pests and disease vectors.Larvicidal Activity of Beauveria bassiana Extracts against Aedes aegypti and Identification of Beauvericins J. Braz. Chem. Soc. 1004 Dengue is a viral infection transmitted to humans by Aedes aegypti mosquitoes that became a major concern of the public health sector. 26 There were 96 million apparent dengue infections globally in 2010, of which the Americas contributed 14% (13 million infections) of worldwide and over half developed in Brazil and Mexico. 27 Due to no effective antiviral agents and licensed vaccine for infection, the decrease in transmission depends only on vector control by elimination of artificial and disposable water inundated larvae breeding sites and application of insecticides. 27,28 Furthermore, studies reveal resistance in the vector population to various substances, in Brazil there is an irregular distribution of insecticide resistance. 28 Furthermore, Aedes mosquitoes also transmit Zika virus; attracting worldwide attention in 2016, when the vector caused widespread epidemic cases in Braz...

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Sequencing of new beauverolides by high‐performance liquid chromatography and mass spectrometry

Cited by 31 publications

References 24 publications

Metabolomics Reveals the Heterogeneous Secretome of Two Entomopathogenic Fungi to Ex Vivo Cultured Insect Tissues

Metabolomics Reveals the Heterogeneous Secretome of Two Entomopathogenic Fungi to Ex Vivo Cultured Insect Tissues

Nonribosomal cyclic peptides: specific markers of fungal infections

Larvicidal Activity of Beauveria bassiana Extracts against Aedes aegypti and Identification of Beauvericins

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