Dipeptide metabolites from the marine derived bacterium Streptomyces acrymicini

Abstract

A investigação química do extrato bruto obtido a partir do meio de crescimento do actinomiceto Streptomyces acrimycini isolado de sedimentos marinhos levou ao isolamento de dois dipeptídeos: a 8-amino-[1,4]diazonano-2,5-diona (1) e leucil-4-hidroxiprolina (3). Os compostos foram isolados a partir do seu meio de crescimento por uma série de etapas cromatográficas e identificados pela análise de seus dados espectroscópicos. O esqueleto macrocíclico da 8-amino-[1,4]diazonano-2,5-diona foi descrito apenas uma vez nas marinobactinas, sideróforos isolados a partir de uma bactéria marinha do gênero Marinobacter.The chemical investigation of the crude extract obtained from the growth media of the marinederived actinomycete Streptomyces acrimycini isolated from marine sediments led to the isolation of two new dipeptide derivatives: 8-amino-[1,4]diazonane-2,5-dione (1) and leucyl-4-hydroxyproline (3). The dipeptides were isolated from the growth media by a series of chromatographic steps, and identified by analysis of spectroscopic data. The macrocyclic carbon backbone of 8-amino-[1,4]diazonane-2,5-dione has been previously reported only once in marinobactins, siderophores isolated from the marine bacterium Marinobacter sp.

Marine Streptomyces as a novel source of bioactive substances

“…These metabolites are useful as antibiotic and anti-inflammatory agents (Moore et al 1999). Two new dipeptide derivatives, 8-amino-[1, 4]diazonane-2, 5-dione (5) and leucyl-4-hydroxyproline (6) were isolated from marine S. acrimycini and their biological roles are yet to be determined (Hernandez et al 2004). Various peptides produced by marine Streptomyces are displayed in Fig.…”

Evaluating methods for the isolation of marine-derived fungal strains and production of bioactive secondary metabolites

“…A number of new compounds have been previously reported by us (Hernandez et al, 2000;Hernandez et al, 2004;Lira et al, 2006;Pimenta et al, 2010). We have subsequently developed a multi-screening approach in order to obtain and select bioactive extracts from marine-derived fungi culture media (Vita-Marques et al, 2008).…”

Marine Biotechnology in Brazil: Recent Developments and Its Potential for Innovation

“…In the 1990 and 2000s, marine biotechnology in Brazil also included metabolite isolation from marine invertebrates and elucidation of the chemical structures of bioactive compounds (e.g., guanidine alkaloids) from marine organisms (Berlinck et al, 1996;Costa et al, 1996;Chehade et al, 1997), and mariculture (Thompson et al, 1999;Wasielesky et al, 2006;da Silva et al, 2013;Ferreira et al, 2016). In the twenty-first century, Brazilian researchers have explored marine microbial products, including the isolation of biologically active compounds, identification of biosynthetic gene clusters from symbiotic microorganisms, developed diagnostic tools to investigate invertebrate diseases caused by potentially pathogenic marine microbes (Hernandez et al, 2000(Hernandez et al, , 2004Pimenta et al, 2010;Romminger et al, 2012;Trindade-Silva et al, 2012;Ferreira et al, 2016;Nicacio et al, 2017), and evaluated antifouling compounds derived from seaweed (Da Gama et al, 2002), and anti-HIV molecules derived from marine brown alga (Stephens et al, 2017). Some relevant actions in Marine biotechnology in Brazil are summarized in Figure 1 and Table 1.…”