Silva Michelli Massaroli da, Andrade Moacir Dos Santos, Bauermeister Anelize, Merfa Marcus Vinícius, Forim Moacir Rossi, Fernandes João Batista, Vieira Paulo Cezar, Silva Maria Fátima das Graças Fernandes da, Lopes Norberto Peporine, Machado Marcos Antônio, Souza Alessandra Alves de
Departamento de Química, Universidade Federal de São Carlos, CP 676, 13565-905 São Carlos-SP, Brazil.
Núcleo Pesquisas em Produtos Naturais e Sintéticos, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, 14040-903 Ribeirão Preto-SP, Brazil.
Molecules. 2017 Jun 13;22(6):985. doi: 10.3390/molecules22060985.
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 ( 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 and to produce genuine natural products. In this work, we identified a range of diketopiperazines from 9a5c growth in XFM, using Ultra-Fast Liquid Chromatography coupled with mass spectrometry. Diketopiperazines are reported for the first time from , which is responsible for citrus variegated chlorosis. We also report here fatty acids from , which were not biologically active as diffusible signals, and the role of diketopiperazines in signal transduction still remains unknown.
二酮哌嗪可通过线性二肽在极端温度或pH条件下的非酶环化作用生成,用于培养细菌和真菌的复杂培养基(包括植物蛋白胨和胰蛋白胨)在热灭菌时也能产生环肽。因此,文献中报道的许多二酮哌嗪是否是微生物生长过程中所用不同复杂培养基形成的假象并不总是很清楚。分析这些化合物的理想方法应能确定它们是由初级代谢产物从头合成的,还是真正的二酮哌嗪。一种含有单一碳源且无预先形成氨基酸的简单限定培养基(培养基或XFM)已成为一种对[具体微生物名称]生长和产生真正天然产物具有特别高潜力的方法。在这项工作中,我们使用超快速液相色谱-质谱联用技术从XFM中[具体微生物名称]9a5c的生长物中鉴定出一系列二酮哌嗪。首次从引起柑橘杂色黄化病的[具体微生物名称]中报道了二酮哌嗪。我们还在此报道了来自[具体微生物名称]的脂肪酸,它们作为可扩散信号没有生物活性,二酮哌嗪在信号转导中的作用仍然未知。