Metabolomics Strategies for the Dereplication of Polyphenols and Other Metabolites in Complex Natural Extracts

Wolfender, Jean‐Luc; Allard, Pierre‐Marie; Kubo, Miwa; Queiroz, Emerson Ferreira

doi:10.1002/9781119427896.ch7

Cited by 5 publications

(6 citation statements)

References 63 publications

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“…In this same way, this work combined different diagrams with molecular networks. Wolfender et al (2019) showed that molecular networking can be used in the identification of polyphenols with library research and cross-checking information with retention time and spectrum comparison in silico [ 41 ]. Pilon et al (2019) showed that the O -glycosylated flavonoid compounds can be well characterized with molecular networking [ 42 ].…”

Section: Discussionmentioning

confidence: 99%

Characterization of Corn Silk Extract Using HPLC/HRMS/MS Analyses and Bioinformatic Data Processing

Fougère

Zubrzycki

Elfakir

et al. 2023

Plants

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In addition to having different biological activities of interest, corn silks play a role in the defense of plants. While benzoxamines and flavonoids have already been identified as molecules of plant defense and growth mechanisms, knowledge on the phytochemical composition of corn silk is lacking. Such knowledge would make it possible to better select the most effective varieties to improve resistance or bioactive properties. In this article, an approach was implemented to map a corn silk extract in two complementary ways. The first one involved working with UHPLC/HRMS data and Kendrick and van Krevelen plots to highlight a homologous series of compounds, such as lipids from 17 to 23 carbons, monoglycosylated flavonoids from 21 to 24 carbons, diglycosylated flavonoids of 26 to 28 carbons and organic acids of 14 to 19 carbons. The second way was to analyze the sample in UHPLC/HRMS2 and to plot mass spectral similarity networks with the GNPS platform and Cytoscape software to refine identification. By combining the information obtained, we were able to propose an identification for 104 detected molecules, including 7 nitrogenous, 28 lipidic and 67 phenolic compounds, leading to the first detailed phytochemical analysis of corn silk extract.

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Section: Discussionmentioning

confidence: 99%

Characterization of Corn Silk Extract Using HPLC/HRMS/MS Analyses and Bioinformatic Data Processing

Fougère

Zubrzycki

Elfakir

et al. 2023

Plants

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“…Several steps are needed for dereplication. With LC‐HRMS technique the main strategies can be grouped as follows (Wolfender et al, 2019): Automated annotation against known compounds; Suspect analysis using known spectral features; Extensive annotation of all compounds with generation of structural hypothesis for unknowns.…”

Section: Metabolomics Overviewmentioning

confidence: 99%

“…The last strategy is based on searching, as exhaustively as possible, the natural product (NP) DBs that mostly contain structures (most of which lack spectral data), in this case the number of putative annotations can be reduced considering the taxonomical information. An interesting application for chemotaxonomy weighting in dereplication of phenols was reported (Wolfender et al, 2019), where taxonomical information was used to reduce the number of putative annotations. However, such comparisons remain largely manual, even though this information is available in some DBs.…”

Section: Metabolomics Overviewmentioning

confidence: 99%

Mass spectrometry‐based metabolomic analysis as a tool for quality control of natural complex products

Mattoli

Gianni

Burico

2022

Mass Spectrometry Reviews

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Metabolomics is an area of intriguing and growing interest. Since the late 1990s, when the first Omic applications appeared to study metabolite's pool (“metabolome”), to understand new aspects of the global regulation of cellular metabolism in biology, there have been many evolutions. Currently, there are many applications in different fields such as clinical, medical, agricultural, and food. In our opinion, it is clear that developments in metabolomics analysis have also been driven by advances in mass spectrometry (MS) technology. As natural complex products (NCPs) are increasingly used around the world as medicines, food supplements, and substance‐based medical devices, their analysis using metabolomic approaches will help to bring more and more rigor to scientific studies and industrial production monitoring. This review is intended to emphasize the importance of metabolomics as a powerful tool for studying NCPs, by which significant advantages can be obtained in terms of elucidation of their composition, biological effects, and quality control. The different approaches of metabolomic analysis, the main and basic techniques of multivariate statistical analysis are also briefly illustrated, to allow an overview of the workflow associated with the metabolomic studies of NCPs. Therefore, various articles and reviews are illustrated and commented as examples of the application of MS‐based metabolomics to NCPs.

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“…The method of molecular networking (MN) was applied to improve the annotation and dereplication of the chromatographic peaks (29). MN was created using the GNPS platform (Global Natural Product Social Molecular Networking) (30).…”

Section: Molecular Networkingmentioning

confidence: 99%

Molecular networking-assisted flavonoid profile of Gypsophila glomerata extract in relation to its protective effects on carbon tetrachloride-induced hepatorenal damage in rats

et al. 2021

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The aim of the study was to provide an in-depth characterization of the methanol-aqueous extract from the aerial parts of Gypsophila glomerata Pall. Ex Adams (Caryophyllaceae) (EGG) and to assess its protective potential on carbon tetrachloride (CCl4)-induced liver and kidney damage in male Wistar rats. Twenty-two flavonoid C-, O- and C,O--glycosides in EGG were annotated by mass spectrometry--based molecular networking; nine of them are reported in this species for the first time. Fourteen-day oral administration of EGG at a dose 200 mg kg−1 bm prevented significantly CCl4-induced liver injury, discerned by an amelioration of the markers of oxidative stress (GSH and MDA) and transaminase activity. EGG decreased the serum level of urea and creatinine as well. The observed improvement of biochemical parameters was supported by histopathological observations. The protective hepatorenal effects of EGG, rich in 2“-О-pentosyl-6-С-hexosyl-apigenin/luteolin/ methylluteolin and their acetyl- and methoxycinnamoyl-derivatives, were comparable with the effects of the positive control silymarin.

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Metabolomics Strategies for the Dereplication of Polyphenols and Other Metabolites in Complex Natural Extracts

Cited by 5 publications

References 63 publications

Characterization of Corn Silk Extract Using HPLC/HRMS/MS Analyses and Bioinformatic Data Processing

Characterization of Corn Silk Extract Using HPLC/HRMS/MS Analyses and Bioinformatic Data Processing

Mass spectrometry‐based metabolomic analysis as a tool for quality control of natural complex products

Molecular networking-assisted flavonoid profile of Gypsophila glomerata extract in relation to its protective effects on carbon tetrachloride-induced hepatorenal damage in rats

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