Dereplication of Streptomyces sp AMC 23 polyether ionophore antibiotics by accurate-mass electrospray tandem mass spectrometry

Autor(es)

Crevelin, Eduardo J. ^[1] ; Crotti, Antonio E. M. ^[1] ; Zucchi, Tiago D. ^[2] ; Melo, Itamar S. ^[2] ; Moraes, Luiz A. B. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Fac Filosofia Ciencias & Letras Ribeirao Preto, Dept Quim, BR-14040901 Ribeirao Preto, SP - Brazil

^[2] Empresa Brasileira Pesquisas Agr Embrapa, Lab Microbiol Ambiental, Jaguariuna, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Mass Spectrometry; v. 49, n. 11, p. 1117-1126, NOV 2014.
• Citações Web of Science: 8

Resumo

Actinomycetes, especially those belonging to the genus Streptomyces, are economically important from a biotechnological standpoint: they produce antibiotics, anticancer compounds and a variety of bioactive substances that are potentially applicable in the agrochemical and pharmaceutical industries. This paper combined accurate-mass electrospray tandem mass spectrometry in the full scan and product ion scan modes with compounds library data to identify the major compounds in the crude extract produced by Streptomyces sp. AMC 23; it also investigated how sodiated nonactin ({[}M+Na](+)) fragmented. Most product ions resulted from elimination of 184 mass units due to consecutive McLafferty-type rearrangements. The data allowed identification of four macrotetrolides homologous to nonactin (monactin, isodinactin, isotrinactin/trinactin and tetranactin) as well as three related linear dimer compounds (nonactyl nonactoate, nonactyl homononactoate and homononactyl homononactoate). The major product ions of the sodiated molecules of these compounds also originated from elimination of 184 and 198 mass units. UPLC-MS/MS in the neutral loss scan mode helped to identify these compounds on the basis of the elimination of 184 and 198 mass units. This method aided monitoring of the relative production of these compounds for 32days and revealed that the biosynthetic process began with increased production of linear dimers as compared with macrotetrolides. These data could facilitate dereplication and identification of these compounds in other microbial crude extracts. Copyright (c) 2014 John Wiley \& Sons, Ltd. (AU)

• Processo FAPESP: 13/20094-0 - Avaliação da atividade antiparasitária e inseticida de compostos benzofurânicos e estudo de suas reações de fragmentação em fase gasosa empregando espectrometria de massas sequencial
• Beneficiário: Antônio Eduardo Miller Crotti
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 08/53000-0 - Isolamento e caracterizacao de micoherbicidas com atividade inibidora da fotossintese empregando a espectrometria de massas.
• Beneficiário: Eduardo José Crevelin
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 09/51145-3 - Espectrometria de massas acelerando o processo de identificação e caracterização de metabólitos secundários bioativos produzidos por actinobactérias
• Beneficiário: Luiz Alberto Beraldo de Moraes
• Modalidade de apoio: Auxílio à Pesquisa - Regular