Advances in Techniques for Profiling Crude Extracts and for the Rapid Identificationof Natural Products: Dereplication, Quality Control and Metabolomics

Wolfender, Jean‐Luc; Marti, Guillaume; Queiroz, Emerson Ferreira

doi:10.2174/138527210792927645

Cited by 97 publications

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“…This, however, requires the comparison of MS data obtained with different detection conditions in order to differentiate protonated or deprotonated molecules from adducts or fragments. [24] The use of high-resolution instruments, such as a TOF-MS or FTICR-MS system, enables the direct determination of the molecular formula of crude mixtures. The accuracy of MS measurement, usually below 5 ppm, and the ratio of intensities of the isotopic patterns, together with the use of rules for heuristic filtering of molecular formulae [25] and chemotaxonomic information, allow an efficient mass-based putative metabolite identification and dereplication (Fig.…”

Section: Rapid Identification Of Phytonutrientsmentioning

confidence: 99%

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Advanced Methods for Natural Product Drug Discovery in the Field of Nutraceuticals

Wolfender

Eugster

Bohni

et al. 2011

Chimia

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Advances in analytical methods and bioassay development have helped to push forward the research in natural products. In plant extracts and nutraceuticals, bioactive compounds are part of a complex mixture. The development of high-resolution methods related to HPLC for both chemical and biological profiling has significantly increased the efficiency of classical bioactivity-guided fractionation procedures. Furthermore, the level of sensitivity obtained by these methods give the possibility to work with few micrograms of compound. This represents a key advantage for rapid localisation of the biological activity and subsequent identification of the compounds of interest. The same methods are also used to study the extracts from a metabolomic view point. The possibility to study them as a whole can highlight synergetic effects, which are likely to occur in plant extracts and nutraceuticals. In this paper, the main trends are summarised and the developments made in our laboratory on profiling crude extracts with UHPLC-TOF-MS, natural product identification at the microgram level using microflow NMR and integration of these methods with biological evaluation are highlighted.

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Section: Rapid Identification Of Phytonutrientsmentioning

confidence: 99%

“…For this, NMR used on-line (LC-NMR) or at-line (LC-SPE-NMR, microflow NMR) may contribute to the missing structural information. [24,26] This method is, however, less sensitive and more time-consuming than MS, but is often mandatory to ascertain structure identification.…”

Section: Rapid Identification Of Phytonutrientsmentioning

confidence: 99%

Advanced Methods for Natural Product Drug Discovery in the Field of Nutraceuticals

Wolfender

Eugster

Bohni

et al. 2011

Chimia

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“…Na busca por substâncias bioativas, responsáveis pelas ações farmacológicas, é evidente a necessidade de estudos utilizando abordagens analíticas mais sensíveis, rápidas e eficazes, como as utilizadas na metabolômica (VILLAS-BÔAS et al, 2005;WOLFENDER, 2010;YULIANA, 2011a;VERPOORTE et al, 2005;LANG, 2008). Uma vez que este reflete o fenótipo do organismo, o metaboloma é, dentre as metodologias "omicas" (genômica, proteomica, metabolomica), o que mais fornece informações no que diz respeito a compreensão dos sistemas biológicos.…”

Section: Metabolômicaunclassified

“…É possível realizar a identificação de substâncias com potencial farmacológico em misturas complexas através da correlação de variáveis como atividade biológica e composição química das amostras. Além disso, a identificação das substâncias requeridas é realizada sem a necessidade de isolamento, o qual demanda tempo e recursos financeiros (VILLAS-BÔAS et al,2005;WOLFENDER et al, 2010;WECKWERTH e MORGENTHAL, 2005, ZHANG et al,2015. Para que sejam detectadas as mínimas diferenças químicas entre as amostras, são utilizadas técnicas analíticas hifenadas que possuem grande sensibilidade, eficiência e rapidez, sendo capazes de demonstrar a diversidade química dos extratos proporcionando uma maior representatividade do metaboloma, e essa são a Ressonância Maginética Nuclear (RMN), Espectrometria de Massas (MS) e cromatografia (líquida ou gasosa) de ultra eficiência, preferencialmente acoplada à detectores de UV e analisadores de massa, que aumentam a performance da análise (CHAGAS-PAULA et al, 2015c;YULIANA et al, 2011a;WECKWERTH e MORGENTHAL, 2005).…”

Section: Metabolômicaunclassified

“…Para que sejam detectadas as mínimas diferenças químicas entre as amostras, são utilizadas técnicas analíticas hifenadas que possuem grande sensibilidade, eficiência e rapidez, sendo capazes de demonstrar a diversidade química dos extratos proporcionando uma maior representatividade do metaboloma, e essa são a Ressonância Maginética Nuclear (RMN), Espectrometria de Massas (MS) e cromatografia (líquida ou gasosa) de ultra eficiência, preferencialmente acoplada à detectores de UV e analisadores de massa, que aumentam a performance da análise (CHAGAS-PAULA et al, 2015c;YULIANA et al, 2011a;WECKWERTH e MORGENTHAL, 2005). Na metabolômica, uma técnica de escolha é a cromatografia líquida de alta ou ultra eficiência (HPLC ou UHPLC) acoplada a detector de ultravioleta com arranjo de diodos (UV-DAD) e espectrometria de massas de alta resolução (HRMS) -LC-UV-MS, devido à abrangência de técnica e sua alta sensibilidade (MORITZ e JOHANSSON, 2008;VILLAS-BÔAS et al, 2005, VAN DER KOOY et al, 2009WOLFENDER et al, 2010). Essa é uma das técnicas empregadas em análises de extratos padronizados, de diferentes partes de uma planta, obtidos através de formas variadas, havendo a possibilidade de identificação de inúmeros constituintes químicos em concentrações ínfimas e sem a necessidade de seu isolamento.…”

Section: Metabolômicaunclassified

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Análise metabolômica da bioatividade em vias COX e LOX-dependentes de plantas da subtribo Lychnophorinae

Godinho¹

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Innovative Strategies in the Search for Bioactive Plant Constituents

Queiroz

Wolfender

2014

Encyclopedia of Analytical Chemistry

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Higher plants represent a rich source of new molecules with interesting pharmacological properties that could be used as lead compounds for the development of new drugs. During the past decade, the investigation of the secondary metabolites from plants has led to the introduction of several important new drugs, such as apomorphine (Apokyn ® ) for the treatment of Parkinson's disease, nitisinone (Orphadin ® ) for the treatment of hereditary tyrosinaemia type 1, and miglustat (Zavesca ® ) for the treatment of the Gaucher disease. Success in drug discovery research using plants is dependent on various issues, but plant selection remains key for all types of these studies. The choice of the appropriate plant material is usually based on information from traditional medicine, chemotaxonomic data, field observation, or random collection. Recently, other approaches have been used, such as reverse pharmacognosy induction of new compounds by stress induction or biotransformation. Extraction and enrichment procedures are also key to avoid chemical degradation and detect the active constituents among hundreds of nonactive constituents before submitting the sample for a first biological screening. New high throughput screening (HTS) strategies have been used to rapidly and efficiently evaluate the biological and chemical potentials of complex matrices, such as plant extracts. In this field, the creation of enriched extracts of natural product (NP) fraction libraries, notably using automatic procedures, opens new possibilities for the research of new lead compounds from higher plants. On the other hand, tremendous advances have been made in molecular biology, affording the development of more predictable in vitro and in vivo bioassays. The combination of metabolite profiling and bioassays that can directly be performed on the fractions that are resolved by analytical high performance liquid chromatography (HPLC) provides the possibility of distinguishing between already‐known bioactive compounds and new molecules directly isolated from crude plant extracts (dereplication). Thus, the tedious isolation of compounds of low interest can be avoided and a targeted isolation of new bioactive products or constituents presenting novel or unusual spectroscopic features can be undertaken. The applications, possibilities, and limitations of the latest technologies applied to the study of plant metabolites, as well as future developments expected in this field, are discussed.

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Advances in Techniques for Profiling Crude Extracts and for the Rapid Identificationof Natural Products: Dereplication, Quality Control and Metabolomics

Cited by 97 publications

References 0 publications

Advanced Methods for Natural Product Drug Discovery in the Field of Nutraceuticals

Advanced Methods for Natural Product Drug Discovery in the Field of Nutraceuticals

Análise metabolômica da bioatividade em vias COX e LOX-dependentes de plantas da subtribo Lychnophorinae

Innovative Strategies in the Search for Bioactive Plant Constituents

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