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

被引：25

作者：

Bonneau, Natacha ^{[1
]}

Chen, Guanming ^{[1
]}

Lachkar, David ^{[1
]}

Boufridi, Asmaa ^{[1
]}

Gallard, Jean-Francois ^{[2
]}

Retailleau, Pascal ^{[2
]}

Petek, Sylvain ^{[3
]}

Debitus, Cecile ^{[3
]}

Evanno, Laurent ^{[1
]}

Beniddir, Mehdi A. ^{[1
]}

Poupon, Erwan ^{[1
]}

机构：

[1] Univ Paris Saclay, Equipe Pharmacognosie Chim Subst Nat BioCIS, CNRS, Univ Paris Sud, 5 Rue JB Clement, F-92290 Chatenay Malabry, France

[2] Univ Paris Saclay, Inst Chim Subst Nat, CNRS, ICSN UPR 2301, 21 Ave Terrasse, F-91198 Gif Sur Yvette, France

[3] Univ Bretagne Occidentale, IUEM, LEMAR, IRD,IFREMER,CNRS, Technopole Brest Iroise Rue Dumont Urville, F-29280 Plouzane, France

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 58期

关键词：

chromophores; cyanines; marine natural dyes; molecular networking; zwitterions; SESQUITERPENOID QUINONES; MARINE SPONGE; GOLGI MEMBRANES; ILIMAQUINONE; NAKIJIQUINONES; VESICULATION; SULFOXIDES; STRATEGY; RESIDUE;

D O I：

10.1002/chem.201702336

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：14454 / 14461

页数：8

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