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Identifying Brazilwood's Marker Component, Urolithin C, in Historical Textiles by Surface-Enhanced Raman Spectroscopy

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Identifying Brazilwood's Marker Component, Urolithin C, in Historical Textiles by Surface-Enhanced Raman Spectroscopy heritage Article Identifying Brazilwood’s Marker Component, Urolithin C, in Historical Textiles by Surface-Enhanced Raman Spectroscopy Brenda Doherty 1,* , Ilaria Degano 2 , Aldo Romani 3, Catherine Higgitt 4 , David Peggie 4, Maria Perla Colombini 2 and Costanza Miliani 5 1 CNR Istituto di Scienze e Tecnologie Chimiche (SCITEC), Dipartimento di Chimica, Biologia e Biotechnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy 2 Dipartimento di Chimica e Chimica Industriale, Universitò di Pisa, Via Giuseppe Moruzzi 13, 56124 Pisa, Italy; [email protected] (I.D.); [email protected] (M.P.C.) 3 Centro di Eccellenza SMAArt, Dipartimento di Chimica, Biologia e Biotechnologie, Università degli Studi di Perugia, Via Elce di Sotto 8, 06123 Perugia, Italy; [email protected] 4 Scientific Department, National Gallery London, Trafalgar Square, London WC2N 5DN, UK; [email protected] (C.H.); [email protected] (D.P.) 5 Istituto per la Scienza del Patrimonio Culturali (ISPC-CNR), Via Guglielmo San Felice 8, 80134 Napoli, Italy; [email protected] * Correspondence: [email protected] Abstract: The fugitive nature of the colorants obtained from sappanwood (Caesalpinia sappan L.) or the South American species commonly known as ‘brazilwoods’ (including other Caesalpinia species and Paubrasilia echinata (Lam.)) makes the identification of brazilwood dyes and pigments in historic artefacts analytically challenging. This difficulty has been somewhat alleviated recently by the recognition and structural elucidation of a relatively stable marker component found in Citation: Doherty, B.; Degano, I.; certain brazilwood dyes and pigments—the benzochromenone metabolite urolithin C. This new Romani, A.; Higgitt, C.; Peggie, D.; understanding creates an ideal opportunity to explore the possibilities for urolithin C’s localization Colombini, M.P.; Miliani, C. and identification in historical artefacts using a variety of analytical approaches. Specifically, in this Identifying Brazilwood’s Marker Component, Urolithin C, in Historical work, micro-destructive surface-enhanced Raman spectroscopic methods following a one-sample Textiles by Surface-Enhanced Raman two-step (direct application of the colloid and then subsequent exposure of the same sample to Spectroscopy. Heritage 2021, 4, HF before reapplication of the colloid) approach are utilized for the examination of four historical 1415–1428. https://doi.org/ brazilwood dyed textiles with the results confirmed via HPLC-DAD analysis. It is shown that 10.3390/heritage4030078 characterization of reference urolithin C is possible, and diagnostic features of this molecule can also be traced in faded historical linen, silk and wool textiles, even in the presence of minor quantities of Academic Editor: Lucia Burgio flavonoid, indigoid and tannin components. The exploitation of the same micro-sample through a series of SERS analyses affords a fuller potential for confirming the characterization of this species. Received: 24 June 2021 Accepted: 22 July 2021 Keywords: urolithin C; brazilein; brazilwood marker component; historical textile Published: 25 July 2021 Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in 1. Introduction published maps and institutional affil- iations. Brazilwood dyestuffs and pigments are derived from a number of closely related and often historically confused species of trees of the Leguminosae family. Heartwood from the so-called ‘soluble redwoods’, sappanwood (Caesalpinia sappan L.) from Southeast Asia and several South American species commonly called brazilwoods (including Caesalpinia brasiliensis L. and Paubrasilia echinata (Lam.)), contain brazilin, the main colorant in brazil- Copyright: © 2021 by the authors. Licensee MDPI, Basel, Switzerland. wood dyes. Brazilin (Figure1a) is a tetracyclic homoisoflavonoid which converts to a more This article is an open access article deeply red colored molecule, brazilein, through autoxidation of a hydroxyl group into a distributed under the terms and carbonyl group (Figure1b). Other phenolic components isolated from brazilwood include conditions of the Creative Commons xanthone, coumarin and various chalcones, flavones and other homoisoflavonoids [1]. Attribution (CC BY) license (https:// The fugitive nature of brazilwood has been documented since the Middle Ages, and creativecommons.org/licenses/by/ its use as both a dyestuff and a pigment has been regulated or proscribed as a result, 4.0/). particularly for use as a sole colorant [2]. It was, however, less expensive than other Heritage 2021, 4, 1415–1428. https://doi.org/10.3390/heritage4030078 https://www.mdpi.com/journal/heritage Heritage 2021, 4 FOR PEER REVIEW 2 Heritage 2021, 4 The fugitive nature of brazilwood has been documented since the Middle Ages, 1416and its use as both a dyestuff and a pigment has been regulated or proscribed as a result, par- ticularly for use as a sole colorant [2]. It was, however, less expensive than other natural naturalred dyestuffs red dyestuffs and gave and an attractive gave an attractive color when color fresh, when so found fresh, great so found use as great a textile use dye, as a textilean organic dye, lake an organicpigment lake in manuscripts pigment in manuscripts(where light exposure (where light was exposure less of an was issue) less and of anin paintings. issue) and Evidence in paintings. of the Evidenceuse of brazilw of theood-derived use of brazilwood-derived lake pigments has lake been pigments found in haspaintings been foundby a diverse in paintings range of by artists, a diverse from range Raphael of artists, to Rembrandt from Raphael and Van to RembrandtGogh [3–5]. andFor textiles, Van Gogh the [ 3dyestuff–5]. For was textiles, generally the dyestuff extracted was in generally neutral or extracted basic aqueous in neutral solutions or basic to aqueouswhich the solutions mordanted to whichtextile thewas mordanted added. To textileprepare was brazilwood added. Tolake prepare pigments, brazilwood various lakerecipes pigments, are known. various In some, recipes the are dyestuff known. is Inextracted some, the from dyestuff the raw is material extracted under from alkaline the raw materialconditions, under then alkaline added conditions,with alum to then precipitate added with the alumpigment to precipitate from the solution. the pigment Alterna- from thetively, solution. the dyestuff Alternatively, could be the extracted dyestuff in could a slig behtly extracted acidic solution in a slightly (e.g., acidicalum solution) solution (e.g., and alumthe pigment solution) precipitated and the pigment on addition precipitated of an alkaline on addition solution of or an of alkaline a source solution of calcium or ofcar- a sourcebonate ofor calciumsulphate carbonate [1,6,7]. or sulphate [1,6,7]. The analytical examination examination of of brazilwood’s brazilwood’s main main colorants colorants is isgenerally generally straightfor- straight- forwardward for the for characterization the characterization of unaltered of unaltered homoisoflavonoid homoisoflavonoid constituents constituents by non-destruc- by non- destructivetive FT-Raman FT-Raman and Infrared and Infrared spectroscopies spectroscopies as well asas wellmicro-destructive as micro-destructive chromatographic chromato- graphicmethods methods alike [8–10]. alike However, [8–10]. However, accurately accurately identifying identifying aged and aged faded and brazilwood-based faded brazilwood- baseddyes and dyes pigments and pigments in historic in historic artworks artworks is challenging. is challenging. Brazilwood’s Brazilwood’s renowned renowned lack lack of ofpermanence permanence has has limited limited the identification the identification of severely of severely faded faded brazilwood brazilwood in artefacts, in artefacts, in the inheritage the heritage science science domain, domain, to only to the only most the mostsensitive sensitive and specific and specific micro-destructive micro-destructive tech- techniques,niques, such such as HPLC as HPLC with withspectrophotometric spectrophotometric or mass or massspectrometric spectrometric detection detection [11]. Such [11]. Suchstudies studies have haveindicated indicated the presence the presence of a ofmi anor minor non-dyestuff non-dyestuff component component that that appears appears to tobe bea brazilwood a brazilwood marker, marker, highlighted highlighted by by No Nowikwik [10]. [10]. This This marker marker component has beenbeen recently identifiedidentified as 3,8,9-trihydroxy-6H-benzo[c]chromen-6-one, urolithinurolithin C (Figure1 1c),c), and unequivocally linked to brazilwood byby PeggiePeggie etet al.al. [[12].12]. Figure 1. Molecular structures of (a) brazilin, ((b)) brazileinbrazilein andand ((cc)) markermarker componentcomponent urolithinurolithin C.C. Urolithin C had initially been thought to be aa degradationdegradation productproduct ofof brazilein,brazilein, yetyet its natural and unquantifiedunquantified presence inin thethe heartwoodheartwood hashas beenbeen highlighted,highlighted, suggestingsuggesting its unrelated presence [13]. [13]. Furtherm Furthermore,ore, observations observations by by Peggie Peggie et et al. al. have have established established a alink link between between an an alkaline alkaline extraction extraction method method an andd the the increased increased presence presence of ofurolithin urolithin C in C inbrazilwood brazilwood dyes dyes and and lake lake pigments. pigments. Tamburini Tamburini
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