Dereplication of microbial extracts and related analytical technologies

Abstract

Natural products still continue to have an important role as a resource of various biologically active substances. Dereplication is a key process in natural product screening that analyzes the extracts of microbial fermentation broths or plant samples. In this review article, we describe and discuss the analytical techniques of dereplication and related technologies in the following sections: 1. Direct detection from microbial colonies. 2. Ultra high performance liquid chromatography (UHPLC)-MS profiling for library construction. 3. Micro-fractionation to identify active peaks. 4. Quantification of small-amount compounds. 5. Structure identification from small amounts. Using these techniques, the desired compound in the mixture library can be rapidly identified.

A High-Resolution LC-MS-Based Secondary Metabolite Fingerprint Database of Marine Bacteria

“…An important distinction of our database and other resources for natural compound research is that ours is a strain-specific metabolome database, rather than a metabolite database. Unlike databases that focus only on the compounds and their analytical signatures (such as UV and MS2 spectra)2829, our approach captures the whole secondary metabolite profiles of bacterial strains. This enables us to use the entire LC-MS profile for chemical fingerprinting, and can quickly determine whether a newly collected bacterium is similar to an existing strain.…”

A Strategy for the Rapid Identification of Fungal Metabolites and the Discovery of the Antiviral Activity of Pyrenocine a and Harzianopyridone

“…The fraction DLM38-A1B was purified by HPLC using a C 8 reversed-phase column Inertsil C8-4 with an isocratic elution (60:40 MeOH/H 2 O), at a flow rate of 7.5 mL min -1 , and detection at l max 254 nm. This separation led to the isolation of 6.5 mg of (-)-naphthoquinoneimine (8), identified by analysis of spectroscopic data and comparison with literature data. 17 The absolute configuration of (8) )] during 6 minutes; flow rate: 1.0 mL/min; detection at l = 280 nm) led to the isolation of 2.0 mg of leucomelone (13) 22 and of 2.1 mg of atromentin (14).…”

“…[3][4][5][6][7] Data obtained from joint UV, LRMS and 1 H NMR analyses only, and sometimes 13 C NMR, can be used in querying databases such as the Dictionary of Natural Products (DNP), Antimarin, MarinLit, and Molecular Networking, as an effective combination for the rapid identification of known structures. 8,9 The rapid identification of secondary metabolites enables further assessment of structures of interest, particularly of unprecedentedly bioactive known compounds.…”

Produtos naturais marinhos: isolamento e identificação de metabólitos inéditos a partir de fungos endofíticos e cianobactérias utilizando técnicas de eliciação química epigenética e desreplicação via redes moleculares

“…A desreplicação ou a identificação de moléculas conhecidas no início do fluxo de trabalho para triagem de produtos naturais minimiza tempo, esforço e custo (Gerwick, Moore, 2012;Ito, Masubuchi, 2014). Estratégias de desreplicação atuais incluem técnicas hifenadas como CLAE-EM, CLAE-RMN, CLAE-RMN-EM e CLAE-EPS-RMN (Mansson et al, 2010;Johansen et al, 2011;Wubshet et al, 2012 .…”

“…A desreplicação baseada em EM tem sido fundamental para as pipelines modernas relacionadas à desreplicação de produtos naturais (Hou et al, 2012;Kasper et al, 2012;Ito, Masubuchi, 2014). Embora EM seja mais sensível do que RMN, muitas vezes é difícil desreplicar determinado composto de forma confiável, usando apenas valores de massas das moléculas cationizadas, devido ao grande número de resultados encontrados nos bancos de dados .…”