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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Mass Spectral Similarity Networking and Gas-Phase Fragmentation Reactions in the Structural Analysis of Flavonoid Glycoconjugates

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Pilon, Alan Cesar [1, 2] ; Gu, Haiwei [3, 4] ; Raftery, Daniel [4, 5] ; Bolzani, Vanderlan da Silva [2] ; Lopes, Norberto Peporine [1] ; Castro-Gamboa, Ian [2] ; Carnevale Neto, Fausto [1, 4, 2]
Total Authors: 7
[1] Univ Sao Paulo, Fac Ciencias Farmaceut Ribeirao Preto, Dept Fis & Quim, NPPNS, BR-14040903 Ribeirao Preto, SP - Brazil
[2] Univ Estadual Paulista, UNESP, Dept Quim Organ, Inst Quim, Nucleo Bioensaios Biossintese & Ecofisiol Prod Na, BR-14800900 Araraquara, SP - Brazil
[3] East China Inst Technol, Jiangxi Key Lab Mass Spectrometry & Instrumentat, Nanchang, Jiangxi - Peoples R China
[4] Univ Washington, Northwest Metabol Res Ctr, Dept Anesthesiol & Pain Med, 850 Republican St, Seattle, WA 98109 - USA
[5] Fred Hutchinson Canc Res Ctr, Publ Hlth Sci Div, Seattle, WA 98109 - USA
Total Affiliations: 5
Document type: Journal article
Source: Analytical Chemistry; v. 91, n. 16, p. 10413-10423, AUG 20 2019.
Web of Science Citations: 2

Flavonoids represent an important class of natural products with a central role in plant physiology and human health. Their accurate annotation using untargeted mass spectrometry analysis still relies on differentiating similar chemical scaffolds through spectral matching to reference library spectra. In this work, we combined molecular network analysis with rules for fragment reactions and chemotaxonomy to enhance the annotation of similar flavonoid glyconjugates. Molecular network topology progressively propagated the flavonoid chemical functionalization according to collision induced dissociation (CID) reactions, as the following chemical attributes: aglycone nature, saccharide type and number, and presence of methoxy substituents. This structure-based distribution across the spectral networks revealed the chemical composition of flavonoids across intra-and interspecies and guided the putatively assignment of 64 isomers and isobars in the Chrysobalanaceae plant species, most of which are not accurately annotated by automated untargeted MS2 matching. These proof of concept results demonstrate how molecular networking progressively grouped structurally related molecules according to their product ion scans, abundances, and ratios. The approach can be extrapolated to other classes of metabolites sharing similar structures and diagnostic fragments from tandem mass spectrometry. (AU)

FAPESP's process: 03/02176-7 - Conservation and sustainable use of the diversity from Cerrado and Atlantic Forest: chemical diversity and prospecting for potential drugs - phase II
Grantee:Vanderlan da Silva Bolzani
Support type: BIOTA-FAPESP Program - Thematic Grants
FAPESP's process: 14/12343-2 - Method development and prospection studies of marine biological resources with citotoxic potential based on systems biology
Grantee:Fausto Carnevale Neto
Support type: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 16/13292-8 - Analysis of nitrogen content in antropic influenced areas in Amazon and Atlantic forest using a metabolomic tools.
Grantee:Alan Cesar Pilon
Support type: Scholarships in Brazil - Post-Doctorate
FAPESP's process: 14/50265-3 - Distribution and metabolism of natural and synthetic xenobiotics: from the comprehension of reactional process to tissue imaging generation
Grantee:Norberto Peporine Lopes
Support type: BIOTA-FAPESP Program - Thematic Grants
FAPESP's process: 10/17935-4 - Development of analytical methods of dereplication by NMR and multivaried analysis of metabolomic profile from Solanaceae species with bioactive potential
Grantee:Alan Cesar Pilon
Support type: Scholarships in Brazil - Doctorate
FAPESP's process: 10/07564-9 - Study of Chrysobalanaceae species with cytotoxic activities: Metabolomic analysis for the understanding of sinergistic associations and their micromolecular complexity
Grantee:Fausto Carnevale Neto
Support type: Scholarships in Brazil - Doctorate