An Unprecedented Blue Chromophore Found in Nature using a "Chemistry First" and Molecular Networking Approach: Discovery of Dactylocyanines A-H

Natacha Bonneau; Guanming Chen; David Lachkar; Asmaa Boufridi; Jean-Francois Gallard; Pascal Retailleau; Sylvain Petek; Cécile Debitus; Laurent Evanno; Mehdi A. Beniddir; Erwan Poupon

doi:10.1002/chem.201702336

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An Unprecedented Blue Chromophore Found in Nature using a "Chemistry First" and Molecular Networking Approach: Discovery of Dactylocyanines A-H

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An Unprecedented Blue Chromophore Found in Nature using a "Chemistry First" and Molecular Networking Approach: Discovery of Dactylocyanines A-H

Natacha Bonneau, Guanming Chen, David Lachkar, Asmaa Boufridi, Jean-Francois Gallard, Pascal Retailleau, Sylvain Petek, Cécile Debitus, Laurent Evanno, Mehdi A. Beniddir, …

Chemistry: A European Journal, Vol.23(58), pp.14454-14461

2017

DOI: https://doi.org/10.1002/chem.201702336

PMID: 28815818

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Abstract

Natural products and bioactive compounds

Analytical chemistry

molecular networking

chromophores

cyanines

marine natural dyes

zwitterions

Guided by a "chemistry first" approach using molecular networking, eight new bright-blue colored natural compounds, namely dactylocyanines A-H (3-10), were isolated from the Polynesian marine sponge Dactylospongia metachromia. Starting from ilimaquinone (1), an hemisynthetic phishing probe (2) was prepared for annotating and matching structurally related natural substances in D. metachromia crude extract network. This strategy allowed characterizing for the first time in Nature the blue zwitterionic quinonoid chromophore. The solvatochromic properties of the latter are reported.

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Title: An Unprecedented Blue Chromophore Found in Nature using a "Chemistry First" and Molecular Networking Approach: Discovery of Dactylocyanines A-H
Authors: Natacha Bonneau (Author) - University of Paris-Saclay
Guanming Chen (Author) - University of Paris-Saclay
David Lachkar (Author) - University of Paris-Saclay
Asmaa Boufridi (Author) - University of Paris-Saclay
Jean-Francois Gallard (Author) - University of Paris-Saclay
Pascal Retailleau (Author) - University of Paris-Saclay
Sylvain Petek (Author) - Université de Bretagne Occidentale
Cécile Debitus (Author) - Université de Bretagne Occidentale
Laurent Evanno (Author) - University of Paris-Saclay
Mehdi A. Beniddir (Author) - University of Paris-Saclay
Erwan Poupon (Author) - University of Paris-Saclay
Publication details: Chemistry: A European Journal, Vol.23(58), pp.14454-14461
Publisher: Wiley-VCH Verlag GmBH & Co. KGaA
DOI: 10.1002/chem.201702336
ISSN: 1521-3765
PMID: 28815818
Organisation Unit: University of the Sunshine Coast, Queensland; Centre for Bioinnovation; School of Science, Technology and Engineering; School of Health - Biomedicine
Language: English
Record Identifier: 99650998602621
Output Type: Journal article

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Collaboration types: Domestic collaboration
Web Of Science research areas: Chemistry, Multidisciplinary

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