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Molecules 2017, 22(6), 985; doi:10.3390/molecules22060985

A Simple Defined Medium for the Production of True Diketopiperazines in Xylella fastidiosa and Their Identification by Ultra-Fast Liquid Chromatography-Electrospray Ionization Ion Trap Mass Spectrometry

1
Departamento de Química, Universidade Federal de São Carlos, CP 676, 13565-905 São Carlos-SP, Brazil
2
Núcleo Pesquisas em Produtos Naturais e Sintéticos, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, 14040-903 Ribeirão Preto-SP, Brazil
3
Centro APTA Citros Sylvio Moreira, Instituto Agronômico, CP 04, 13490-970 Cordeirópolis-SP, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Thomas J. Schmidt
Received: 30 March 2017 / Revised: 24 May 2017 / Accepted: 8 June 2017 / Published: 13 June 2017
(This article belongs to the Section Natural Products)
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Abstract

Diketopiperazines can be generated by non-enzymatic cyclization of linear dipeptides at extreme temperature or pH, and the complex medium used to culture bacteria and fungi including phytone peptone and trypticase peptone, can also produce cyclic peptides by heat sterilization. As a result, it is not always clear if many diketopiperazines reported in the literature are artifacts formed by the different complex media used in microorganism growth. An ideal method for analysis of these compounds should identify whether they are either synthesized de novo from the products of primary metabolism and deliver true diketopiperazines. A simple defined medium (X. fastidiosa medium or XFM) containing a single carbon source and no preformed amino acids has emerged as a method with a particularly high potential for the grown of X. fastidiosa and to produce genuine natural products. In this work, we identified a range of diketopiperazines from X. fastidiosa 9a5c growth in XFM, using Ultra-Fast Liquid Chromatography coupled with mass spectrometry. Diketopiperazines are reported for the first time from X. fastidiosa, which is responsible for citrus variegated chlorosis. We also report here fatty acids from X. fastidiosa, which were not biologically active as diffusible signals, and the role of diketopiperazines in signal transduction still remains unknown. View Full-Text
Keywords: Xylella fastidiosa; X. fastidiosa medium XFM; diketopiperazines; Ultra-Fast Liquid Chromatograph; mass spectrometry; electrospray ionization Xylella fastidiosa; X. fastidiosa medium XFM; diketopiperazines; Ultra-Fast Liquid Chromatograph; mass spectrometry; electrospray ionization
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Silva, M.M.; Andrade, M.S.; Bauermeister, A.; Merfa, M.V.; Forim, M.R.; Fernandes, J.B.; Vieira, P.C.; Silva, M.F.G.F.; Lopes, N.P.; Machado, M.A.; Souza, A.A. A Simple Defined Medium for the Production of True Diketopiperazines in Xylella fastidiosa and Their Identification by Ultra-Fast Liquid Chromatography-Electrospray Ionization Ion Trap Mass Spectrometry. Molecules 2017, 22, 985.

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