Studies on Metabolites of Mycoparasitic Fungi. V. Ion-Spray Ionization Mass Spectrometric Analysis of Trichokonin-II, a Peptaibol Mixture Obtained from the Culture Broth of Trichoderma koningii.

Huang, Qing; Tezuka, Yasuhiro; Hatanaka, Y.; Kikuchi, Tohru; Nishi, Arasuke; Tubaki, K.

doi:10.1248/cpb.44.590

Cited by 23 publications

(33 citation statements)

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“…y 7 and b 13 ). This is analogous to the case of triple-stage mass spectra, where sequential fragments ('granddaughter' ions) are observed.…”

Section: Terminology For Indicating Sequential Peptide Fragmentsmentioning

confidence: 99%

“…In the present paper we use the modified Roepstoff-Biemann notation of peptide fragmentation, as described in a recent review. 16 The structurally most useful peaks in the spectrum are due to the y 7 (m/z 774) and b 13 (m/z 1149) complementary backbone fragmentation at the 13 Pro residue. The main fragments are often accompanied by satellite peaks at ± 14 and ± 28 u distances (marked with asterisks in Fig.…”

Section: Single-stage Mass Spectrummentioning

confidence: 99%

“…Recently, electrospray ionization mass spectrometry (ESI-MS) combined with low-energy CID experiments on a triple-quadrupole mass spectrometer has been successfully applied to determine the sequence of three closely related peptaibol components in a mixture. [11][12][13] Triple-quadrupole instruments have access only to low-energy collision regimes, however, and have only a moderate resolution. High-energy CID experiments have the advantage of kilovolt collision energies.…”

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confidence: 99%

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Microheterogeneity Characterization of a Paracelsin Mixture fromTrichoderma reesei Using High-energy Collision-induced Dissociation Tandem Mass Spectrometry

Pócsfalvi¹,

Ritieni

Ferranti

et al. 1997

Rapid Commun. Mass Spectrom.

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The microheterogeneity of the paracelsin mixture broth of Trichoderma reesei was analysed using mass spectrometric methods, in particular high-energy collision-induced dissociation (CID) tandem mass spectrometry (MS/MS). Based on the liquid secondary ion mass spectrum of the mixture, there are three main components, with molecular masses M and (M +/- 14), together with two minor components of molecular weight (M +/- 28). The high-energy CID tandem mass spectra of both the protonated and sodiated molecules yielded abundant and characteristic fragment ions, but of very different types. It was found that a paracelsin peptaibol in a mixture could be successfully sequenced based on the tandem mass spectra of its protonated and sodiated molecules or, alternatively, on the tandem mass spectra of its y7 and b13 fragment ions. A terminology for indicating these sequential peptide fragments is proposed. To determine the sequence of new analogues, tandem mass spectra of the y7, (y7 +/- 14), b13, (b13 +/- 14) and (MH +/- 14) positive ions were also taken. Based on these experiments, four new paracelsin components (PA-F, PA-G, PA-H and PA-I) were sequenced successfully. The microheterogeneity of the mixture was found to be more pronounced than had been assumed previously. In these new analogues, besides positions 6 and 9, position 17 is also involved in the exchange. MS/MS studies on minor fragment ions, such as (b13-28) and (b8-14) show further microheterogeneity at positions 3, 5, 10 and 12, which increase the number of possible minor components.

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“…y 7 and b 13 ). This is analogous to the case of triple-stage mass spectra, where sequential fragments ('granddaughter' ions) are observed.…”

Section: Terminology For Indicating Sequential Peptide Fragmentsmentioning

confidence: 99%

Section: Single-stage Mass Spectrummentioning

confidence: 99%

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confidence: 99%

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Microheterogeneity Characterization of a Paracelsin Mixture fromTrichoderma reesei Using High-energy Collision-induced Dissociation Tandem Mass Spectrometry

Pócsfalvi¹,

Ritieni

Ferranti

et al. 1997

Rapid Commun. Mass Spectrom.

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“…We propose the names linopubescin (LPB) A, B, and C for those new compounds 30 -32, respectively, from Trichoderma pubescens ( Tables 4 and 5 Compounds 35 and 36 might be identical with the partial sequences 3 and 4 recently published for T. stromaticum CBS 101875 [3]. The N-terminal sequence, Ac-Aib-AlaAib-Ala-Aib-Aib-Gln-Aib-Val-Aib, comprising positions 1 -10, was first reported for the following 20-residue peptaibols, namely paracelsin C from T. reesei QM 9414 [39], trichosporin B-IVc from T. polysporum TMI 60146 [40], trichokonin VIII from a strain identified as T. koningii [41], and for longibrachins A III and A IV, from T. longibrachiatum M 853431 [42]. The isobaric sequence with Iva 8 instead of Val 8 has not yet been published.…”

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confidence: 97%

Peptaibiomics: Screening for Polypeptide Antibiotics (Peptaibiotics) from Plant-ProtectiveTrichoderma Species

Degenkolb¹,

Gräfenhan²,

Berg³

et al. 2006

C&B

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were selected because of their antagonistic potential against Eutypa dieback and Esca which are fungal diseases of grapevine trunks. These isolates were screened for the production of a group of polypeptide antibiotics named peptaibiotics, including its subgroups peptaibols and lipopeptaibols. Fully-grown fungal cultures on potato-dextrose agar were extracted with CH 2 Cl 2 /MeOH, and these extracts were subjected to SPE using C 18 cartridges. The methanolic eluates were analyzed by on-line LC/ESI-MS n coupling -a method which is referred to as peptaibiomics . New seven-, ten-, and eleven-residue lipopeptaibols, with N-terminal alkanoyl, and Cterminal leucinol or isoleucinol residues were found and named lipostrigocins and lipopubescins. Furthermore, new 18-residue peptaibols named trichostromaticins and 19-residue peptaibols named trichostrigocins were discovered. One peptaibiotic carrying a free C-terminal valine (or isovaline) named trichocompactin XII was also sequenced. These results corroborate the hypothesis that peptaibiotics might contribute to the plant-protective action of their fungal producers. The data also point out that comparison of peptaibiotic sequences is of limited relevance in order to establish chemotaxonomic relationships among species of the genus Trichoderma.

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“…tandyukisins B-D (decalin derivative) cytotoxic [328] trichodenone A, B, C cytotoxic [329] trichodermin trichotecene toxin [319,330] trichodermol (detected in hydrolysed crude extracts) trichotecene toxin [331] trichorzin peptaibol [332] tyrosol bioactive compound [311] verticillol bioactive compound [310] viridiofungin A anti-phytopathogen [333] Trichoderma koningii 6, 4-oxopentyl-2H-pyran-2-one antifungal [334] 6-pentyl-pyranone antifungal [334] 7-O-methylkoninginin D (polyketide derivative) antimicrobial [335] alpha-aminoisobutyric acid [336] amino alcohol (peptaibols) [336] decanolactone antifungal [334] koninginins A, D, E, F, L, M phospholipase A 2 inhibitors [335,337,338] stigmasterol antifungal [334] trichodermaketones A-D (polyketide derivatives) antimicrobial [335,337] trichokonins (peptaibols) antimicrobial [339][340][341] Trichoderma longibranchiatum longibranchins (LGA I-V and LGB II-III) (peptaibols) biooactive compounds [342][343][344][345] Database on potential toxigenic capacities of microorganisms used for industrial production…”

Section: Microorganism Secondary Metabolites Commentsmentioning

confidence: 99%

Database on the taxonomical characterisation and potential toxigenic capacities of microorganisms used for the industrial production of food enzymes and feed additives, which do not have a recommendation for Qualified Presumption of Safety

Benito

Ibáñez

Moncho

et al. 2017

EFSA Supporting Publications

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The present work constitutes the external scientific report of the EFSA open call OC/EFSA/FEED/2015/01. The aim of the call was to provide EFSA with a database from a review on the taxonomical description and potential toxigenic capacities of microorganisms used for the industrial production of feed additives and food enzymes. The review includes microorganisms used as source of feed additives and food enzymes for which EFSA has received or can potentially receive applications for safety assessment, and which have not been recommended for Qualified Presumption of Safety status. The database also comprises the molecular taxonomical identifiers and biosynthetic pathways involved in the production of toxic compounds and the responsible genes. The main result of the project is shown as a database developed according to the EFSA data structure. The methodological aspects and the queries used in the systematic search, as well as the procedure applied for the screening of scientific documents retrieved are described in this report. Details are available in supplementary appendices.In total, 22970 scientific documents were screened in the literature search, from which 411 were initially selected for providing pertinent data for the scope of the project. From the review of the selected articles, 474 bioactive secondary metabolites were recorded and 59 compounds were further studied in order to obtain data on their toxicology and the conditions in which they are produced by the microorganisms used in industrial fermentations. The database generated in this project comprises details that characterise, when available, the production conditions, genes involved and toxicity of these 59 compounds. This provides information that can be used to establish safety measures when using potentially toxigenic microorganisms in industrial fermentations Disclaimer: The present document has been produced and adopted by the bodies identified above as author(s). This task has been carried out exclusively by the author(s) in the context of a contract between the European Food Safety Authority and the author(s), awarded following a tender procedure. The present document is published complying with the transparency principle to which the Authority is subject. It may not be considered as an output adopted by the Authority. The European Food Safety Authority reserves its rights, view and position as regards the issues addressed and the conclusions reached in the present document, without prejudice to the rights of the authors. Acknowledgements:We thank the following EFSA satff: Jaime Aguilera, Margarita Aguilera-Gómez, Jane Richardson, Mario Monguidi and Davide Gibin for their valuable help and collaboration throughout the project. We also would like to thank the members of AINIA: Sonia Porta, Lidia Tomás, Joaquin Espí and Juan Antonio Nieto for providing expertise in biotechnology and molecular biology and contributing with their efforts to achieve the goals of this project, and Violeta Gómez from the University of Navarra for her colla...

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Studies on Metabolites of Mycoparasitic Fungi. V. Ion-Spray Ionization Mass Spectrometric Analysis of Trichokonin-II, a Peptaibol Mixture Obtained from the Culture Broth of Trichoderma koningii.

Cited by 23 publications

References 0 publications

Microheterogeneity Characterization of a Paracelsin Mixture fromTrichoderma reesei Using High-energy Collision-induced Dissociation Tandem Mass Spectrometry

Microheterogeneity Characterization of a Paracelsin Mixture fromTrichoderma reesei Using High-energy Collision-induced Dissociation Tandem Mass Spectrometry

Peptaibiomics: Screening for Polypeptide Antibiotics (Peptaibiotics) from Plant-ProtectiveTrichoderma Species

Database on the taxonomical characterisation and potential toxigenic capacities of microorganisms used for the industrial production of food enzymes and feed additives, which do not have a recommendation for Qualified Presumption of Safety

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