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25 Aug 10:42

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

by Natacha Bonneau, Guanming Chen, David Lachkar, Asmaa Boufridi, Jean-François Gallard, Pascal Retailleau, Sylvain Petek, Cécile Debitus, Laurent Evanno, Mehdi Beniddir, Erwan Poupon

Abstract

Guided by a “chemistry first” approach using molecular networking, eight new bright-blue colored natural compounds, namely dactylocyanines A–H (310), 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.

Thumbnail image of graphical abstract

Blue-eyed meroterpenes: Guided by a “chemistry first” approach using molecular networking, eight new bright-blue-colored natural compounds, namely dactylocyanines A–H bearing a zwitterionic quinonoid chromophore, were isolated from the Polynesian marine sponge Dactylospongia metachromia.