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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, P.
dc.contributor.authorOliveira, J.
dc.contributor.authorPina, F.
dc.contributor.authorTeixeira, N.
dc.contributor.authorde Freitas, V.
dc.contributor.authorBrás, N. F.
dc.contributor.authorClemente, A.
dc.contributor.authorRangel, M.
dc.contributor.authorSilva, A. M. S.
dc.contributor.authorMelo, M. J.
dc.date.accessioned2021-03-04T15:40:55Z
dc.date.available2021-03-04T15:40:55Z
dc.date.issued2020-04
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.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationP. Nabais, J. Oliveira, F. Pina, N. Teixeira, V. de Freitas, N. F. Bras, A. Clemente, M. Rangel, A. M. S. Silva, M. J. Melo, A 1000-year-old mystery solved: Unlocking the molecular structure for the medieval blue from Chrozophora tinctoria, also known as folium. Sci. Adv. 6, eaaz7772 (2020).pt_PT
dc.identifier.doi10.1126/sciadv.aaz7772pt_PT
dc.identifier.urihttp://hdl.handle.net/10451/46654
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherAmerican Association for the Advancement of Sciencept_PT
dc.relationFCT UID/QUI/50006/2019pt_PT
dc.relationproject STEMMA—From singing to writing—survey on material production and routes of Galician-Portuguese Lyricpt_PT
dc.relationFCT PTDC/LLT-EGL/30984/2017pt_PT
dc.relationFCT IF/00225/2015pt_PT
dc.relationFCT IF/01355/2014pt_PT
dc.relationREQUIMTE/EEC2018/PTDC/QUI-OUT/29925/2017pt_PT
dc.relationFCT PTDC/QUI-OUT/29925/2017pt_PT
dc.relationCORES Ph.D. programme (PD/ BD/105895/2014)pt_PT
dc.rights.urihttp://creativecommons.org/licenses/by-nc/4.0/pt_PT
dc.titleA 1000-year-old mystery solved: Unlocking the molecular structure for the medieval blue from Chrozophora tinctoria, also known as foliumpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.issue16pt_PT
oaire.citation.startPageeaaz7772pt_PT
oaire.citation.titleScience Advancespt_PT
oaire.citation.volume6pt_PT
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT

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