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A 1000-year-old mystery solved: Unlocking the molecular structure for the medieval blue from Chrozophora tinctoria, also known as folium

2020-04Artigo científico Acesso aberto
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dc.contributor.authorNabais, Paula
dc.contributor.authorOliveira, Joana
dc.contributor.authorPina, Fernando
dc.contributor.authorTeixeira, Natércia
dc.contributor.authorDe Freitas, Victor
dc.contributor.authorBrás, Natércia F.
dc.contributor.authorClemente, A.
dc.contributor.authorRangel, Maria
dc.contributor.authorSilva, Artur M. S.
dc.contributor.authorMelo, Maria João
dc.contributor.institutionLAQV@REQUIMTE
dc.contributor.pblAmerican Association for the Advancement of Science
dc.date.accessioned2020-10-17T00:19:47Z
dc.date.available2020-10-17T00:19:47Z
dc.date.issued2020-04
dc.descriptionUID/QUI/50006/2019 PTDC/LLT-EGL/30984/2017 IF/00225/2015 IF/01355/2014 REQUIMTE/EEC2018/PTDC/QUI-OUT/29925/2017 PTDC/QUI-OUT/29925/2017 PD/BD/105895/2014
dc.description.abstractThe molecular structure of the medieval watercolor known as folium has finally been solved in the 21st century. The interdisciplinary approach taken was the key to producing extracts that had been prepared following medieval instructions, and shows the blue/purple chromophore as the major dye in Chrozophora tinctoria fruits (shell). A multi-analytical characterization of its structure was made using HPLC-DAD-MS, GC-MS, NMR (1H, 13C, COSY, HSQC, HMBC, INADEQUATE), and computational studies. The results demonstrate that the blue compound corresponds to 6'-hydroxy-4,4'-dimethoxy-1,1'-dimethyl-5'-{[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl] oxy}-[3,3'-bipyridine]-2,2',5,6(1H,1'H)-tetraone, a hermidin derivative, which we named chrozophoridin. Experimental data and computational modeling studies show that this mono-glycosylated dimer is represented by two stable isomers (atropisomers). This is an indispensable piece of knowledge for the characterization of this medieval dye in works of art such as medieval manuscript illuminations and for testing its stability and contributes to the preservation of our cultural heritage.en
dc.description.versionpublishersversion
dc.description.versionpublished
dc.format.extent736882
dc.identifier.doi10.1126/sciadv.aaz7772
dc.identifier.issn2375-2548
dc.identifier.otherPURE: 25964500
dc.identifier.otherPURE UUID: 3b723dda-fb77-4114-9a3c-2066b1d718e5
dc.identifier.otherScopus: 85083631173
dc.identifier.otherPubMed: 32426456
dc.identifier.otherPubMedCentral: PMC7164948
dc.identifier.otherWOS: 000528276800040
dc.identifier.otherORCID: /0000-0001-8529-6848/work/82115369
dc.identifier.otherORCID: /0000-0001-7393-6801/work/82156855
dc.identifier.urihttp://hdl.handle.net/10362/105768
dc.identifier.urlhttps://www.scopus.com/pages/publications/85083631173
dc.language.isoeng
dc.peerreviewedyes
dc.subjectGeneral
dc.titleA 1000-year-old mystery solved: Unlocking the molecular structure for the medieval blue from Chrozophora tinctoria, also known as foliumen
dc.typejournal article
degois.publication.issue16
degois.publication.titleScience Advances
degois.publication.volume6
dspace.entity.typePublication
rcaap.rightsopenAccess

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