Molecular networking prospection and characterization of terpenoids and C<sub>15</sub>-acetogenins in Brazilian seaweed extracts

Philippus, Ana Cláudia; Zatelli, Gabriele Andressa; Wanke, Tauana; Barros, Maria Gabriela de A.; Kami, Satomy A.; Lhullier, Cíntia; Armstrong, Lorene; Sandjo, Louis P.; Falkenberg, Miriam

doi:10.1039/c8ra02802h

Cited by 18 publications

(18 citation statements)

References 50 publications

(114 reference statements)

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“…GNPS is being used to network data acquired on a number of different mass spectrometers in a wide variety of exploratory studies, with samples originating from diverse environments and used for various purposes. The environments range from the indoor environment [36][37][38] to dissolved organic matter in the oceans 39 ; from microbes in culture 9,[40][41][42][43] to mouse 44 or human microbiomes 45,46 or infections [47][48][49] ; from clinical samples 22,50,51 to plants 52 , algae 53 , sponges 5,54 , and corals 55 ; as well as a number of other sample types 16,56 . In addition, molecular networking has been applied to NPs discovery from a variety of organisms [57][58][59][60] , forensics 61 , small-molecule identification 24,62 , and biological discovery in hypothesis-driven research 63 .…”

Section: Applications Of the Methodsmentioning

confidence: 99%

Reproducible molecular networking of untargeted mass spectrometry data using GNPS

et al. 2020

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Global Natural Product Social Molecular Networking (GNPS) is an interactive online small molecule-focused tandem mass spectrometry (MS 2 ) data curation and analysis infrastructure. It is intended to provide as much chemical insight as possible into an untargeted MS 2 dataset and to connect this chemical insight to the user's underlying biological questions. This can be performed within one liquid chromatography (LC)-MS 2 experiment or at the repository scale. GNPS-MassIVE is a public data repository for untargeted MS 2 data with sample information (metadata) and annotated MS 2 spectra. These publicly accessible data can be annotated and updated with the GNPS infrastructure keeping a continuous record of all changes. This knowledge is disseminated across all public data; it is a living dataset. Molecular networking-one of the main analysis tools used within the GNPS platform-creates a structured data table that reflects the molecular diversity captured in tandem mass spectrometry experiments by computing the relationships of the MS 2 spectra as spectral similarity. This protocol provides step-by-step instructions for creating reproducible, high-quality molecular networks. For training purposes, the reader is led through a 90-to 120-min procedure that starts by recalling an example public dataset and its sample information and proceeds to creating and interpreting a molecular network. Each data analysis job can be shared or cloned to disseminate the knowledge gained, thus propagating information that can lead to the discovery of molecules, metabolic pathways, and ecosystem/community interactions.

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Section: Applications Of the Methodsmentioning

confidence: 99%

Reproducible molecular networking of untargeted mass spectrometry data using GNPS

et al. 2020

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“…Thus, a visual representation of the structural relationships between natural compounds within crude extracts is generated, where a node within the network represents a compound and the relatedness between two compounds (nodes) is referred to as an edge. Moreover, GNPS allows for the comparison of the tandem MS spectra to the publicly available spectral library for rapid identification of known compounds ( Wang et al, 2016 ; Philippus et al, 2018 ).…”

Section: Introductionmentioning

confidence: 99%

A Metabolomics and Molecular Networking Approach to Elucidate the Structures of Secondary Metabolites Produced by Serratia marcescens Strains

et al. 2021

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An integrated approach that combines reverse-phase high-performance liquid chromatography (RP-HPLC), electrospray ionization mass spectrometry, untargeted ultra-performance liquid chromatography coupled to tandem mass spectrometry (UPLC-MSE) and molecular networking (using the Global Natural Products Social molecular network platform) was used to elucidate the metabolic profiles and chemical structures of the secondary metabolites produced by pigmented (P1) and non-pigmented (NP1) Serratia marcescens (S. marcescens) strains. Tandem mass spectrometry-based molecular networking guided the structural elucidation of 18 compounds for the P1 strain (including 6 serratamolides, 10 glucosamine derivatives, prodigiosin and serratiochelin A) and 15 compounds for the NP1 strain (including 8 serratamolides, 6 glucosamine derivatives and serratiochelin A) using the MSE fragmentation profiles. The serratamolide homologues were comprised of a peptide moiety of two L-serine residues (cyclic or open-ring) linked to two fatty acid chains (lengths of C10, C12, or C12:1). Moreover, the putative structure of a novel open-ring serratamolide homologue was described. The glucosamine derivative homologues (i.e., N-butylglucosamine ester derivatives) consisted of four residues, including glucose/hexose, valine, a fatty acid chain (lengths of C13 – C17 and varying from saturated to unsaturated) and butyric acid. The putative structures of seven novel glucosamine derivative homologues and one glucosamine derivative congener (containing an oxo-hexanoic acid residue instead of a butyric acid residue) were described. Moreover, seven fractions collected during RP-HPLC, with major molecular ions corresponding to prodigiosin, serratamolides (A, B, and C), and glucosamine derivatives (A, C, and E), displayed antimicrobial activity against a clinical Enterococcus faecalis S1 strain using the disc diffusion assay. The minimum inhibitory and bactericidal concentration assays however, revealed that prodigiosin exhibited the greatest antimicrobial potency, followed by glucosamine derivative A and then the serratamolides (A, B, and C). These results provide crucial insight into the secondary metabolic profiles of pigmented and non-pigmented S. marcescens strains and confirms that S. marcescens strains are a promising natural source of novel antimicrobial metabolites.

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“…Seaweeds are currently a popular and common food source around the world as they are rich in nutrients [1]. Seaweeds are reported to contain various substances, including acetogenins [2], oxylipins [3], polyphenols [4], terpenoids [5], steroids [6], and nucleosides [7]. The active compounds in seaweeds have been studied for various biological Mar.…”

Section: Introductionmentioning

confidence: 99%

Sargachromenol Purified from Sargassum horneri Inhibits Inflammatory Responses via Activation of Nrf2/HO-1 Signaling in LPS-Stimulated Macrophages

et al. 2021

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In this study, we isolated sargachromenol (SC) from Sargassum horneri and evaluated its anti-inflammatory effect in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. SC did not show cytotoxicity at all concentrations and effectively increased the cell viability by reducing the nitric oxide (NO) and intracellular reactive oxygen species (ROS) production in LPS-stimulated RAW 264.7 macrophages. In addition, SC decreased the mRNA expression levels of inflammatory cytokines (IL-1β, IL-6, and TNF-α) and inflammatory mediators (iNOS and COX-2). Moreover, SC suppressed the activation of nuclear factor kappa-light-chain-enhancer of activated B cells (NFκB) and mitogen-activated protein kinase (MAPK) signaling, whereas activated the nuclear factor erythroid 2-related factor 2/heme oxygenase-1 (Nrf2/HO-1) signaling in LPS-stimulated RAW 264.7 macrophages. Interestingly, the anti-inflammatory effect of SC was abolished by the inhibition of HO-1 in LPS-stimulated RAW 264.7 macrophages. According to the results, this study suggests that the antioxidant capacity of SC leads to its anti-inflammatory effect and it potentially may be utilized in the nutraceutical and pharmaceutical sectors.

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Molecular networking prospection and characterization of terpenoids and C₁₅-acetogenins in Brazilian seaweed extracts

Abstract: Molecular networking of Brazilian marine algae.

Cited by 18 publications

References 50 publications

Reproducible molecular networking of untargeted mass spectrometry data using GNPS

Reproducible molecular networking of untargeted mass spectrometry data using GNPS

A Metabolomics and Molecular Networking Approach to Elucidate the Structures of Secondary Metabolites Produced by Serratia marcescens Strains

Sargachromenol Purified from Sargassum horneri Inhibits Inflammatory Responses via Activation of Nrf2/HO-1 Signaling in LPS-Stimulated Macrophages

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Molecular networking prospection and characterization of terpenoids and C15-acetogenins in Brazilian seaweed extracts

Abstract: Molecular networking of Brazilian marine algae.

Cited by 18 publications

References 50 publications

Reproducible molecular networking of untargeted mass spectrometry data using GNPS

Reproducible molecular networking of untargeted mass spectrometry data using GNPS

A Metabolomics and Molecular Networking Approach to Elucidate the Structures of Secondary Metabolites Produced by Serratia marcescens Strains

Sargachromenol Purified from Sargassum horneri Inhibits Inflammatory Responses via Activation of Nrf2/HO-1 Signaling in LPS-Stimulated Macrophages

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Molecular networking prospection and characterization of terpenoids and C₁₅-acetogenins in Brazilian seaweed extracts