Sequencing of cyclodepsipeptides (destruxins) using positive fast atom bombardment desorption tandem mass spectrometry

Lange, Catherine; Mulheim, C.; Vey, A.; Païs, M.

doi:10.1002/bms.1200210108

Cited by 14 publications

(1 citation statement)

References 34 publications

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“…Thirty-nine different destruxins have been reported [10]. The mass spectral fragmentation patterns of destruxins have also been well characterized [34]–[36], and again the product ion mass spectra we obtained in this study were virtually identical to the in-source CID mass spectra previously reported. The D-alpha-hydroxy acid residue, which is a major site of heterogeneity in the destruxins, gives a prominent fragment ion designated D + (34), allowing the identification of this residue.…”

Section: Resultssupporting

confidence: 81%

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: Resultssupporting

confidence: 81%

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

et al. 2013

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Comparison of collisionally activated dissociation mass spectra for the identification of cyclopeptides and cyclodepsipeptides

Cavelier

Enjalbal

Martínez

et al. 1999

Rapid Commun. Mass Spectrom.

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Collisionally activated dissociation (CAD) spectra of protonated molecules of cyclopeptides and cyclodepsipeptides obtained with two different mass spectrometry systems were compared. Fragmentations were obtained either from collisions induced in the ion source of an electrospray mass spectrometer fitted with a single quadrupole by increasing the extracting cone voltage or from collisions with an inert gas in a free-field area of a fast-atom bombardment (FAB) mass spectrometer. Similar fragmentation pathways were produced with the two configurations even though actual tandem mass spectrometry experiments with magnetic and electric sectors provided more information than cone-induced dissociations. However, only the latter mode allowed us to perform mass spectrometric analyses coupled to liquid chromatography (LC/ ESI-MS) at low cost on commercially widespread instruments. Copyright # 1999 John Wiley & Sons, Ltd. Received 15 January 1999; Revised 8 March 1999; Accepted 9 March 1999 The development of fast-atom bombardment (FAB) mass spectrometry 1 provides easy identification of polar compounds in particular of peptides.2 Furthermore, the more recent electrospray ionization (ESI) technique 3 allows the analysis of mixtures by readily coupling mass spectrometry to liquid chromatography (LC/ESI-MS). 4 Although other techniques can be applied for the characterization of linear peptides, the recourse to mass spectrometry is compulsory for the identification of cyclic structures. Indeed such compounds lacking a free N-terminal group are not suitable for Edman degradation or amino acid analysis. Besides, the presence of N-alkylated residues, frequently observed in natural cyclic peptides, hampers the sequence determination by these techniques.Mass spectrometric analysis of cyclopeptides has been reviewed 5 and FAB mass spectra of various cyclopeptides have been studied in our laboratory. 6-11The limited number of fragmentations that are generally observed in the mass spectrum of a peptide led to the use of tandem mass spectrometry 12 to produce relevant sequence information. Nevertheless, in the case of ESI-MS experiments, it has been reported in the literature 13 that characteristic sequence ions can also be produced without the necessity for classical tandem mass spectrometry. It was found that collision-induced dissociation could be achieved by increasing the voltage of the sampling cone before the analyzer entrance. These results were particularly interesting as peptide sequencing could be achieved from LC/ESI-MS undertaken with standard equipment fitted with a single quardrupole. 13 Thus, it seemed interesting to verify whether previous results 6,7 obtained for the cyclic tetrapeptide tentoxin with a double-focusing mass spectrometer of the EB design fitted with a FAB ion source could be reproduced with a single quardrupole ESI mass spectrometer. A second series of cyclic hexapeptides and derived depsipeptides from the destruxin family was also submitted to such comparative studies. Our aim was to assess if the s...

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MS/MS applications in biological problems

Favretto¹,

Traldi²

1993

Mass Spectrometry Reviews

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Sequencing of cyclodepsipeptides (destruxins) using positive fast atom bombardment desorption tandem mass spectrometry

Cited by 14 publications

References 34 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

Comparison of collisionally activated dissociation mass spectra for the identification of cyclopeptides and cyclodepsipeptides

MS/MS applications in biological problems

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