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Journal of Chromatography a Flavylium Chromophores As Species Markers for Dragon's Blood Resins from Dracaena and Daemonorops

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Journal of Chromatography a Flavylium Chromophores As Species Markers for Dragon's Blood Resins from Dracaena and Daemonorops Journal of Chromatography A, 1209 (2008) 153–161 Contents lists available at ScienceDirect Journal of Chromatography A journal homepage: www.elsevier.com/locate/chroma Flavylium chromophores as species markers for dragon’s blood resins from Dracaena and Daemonorops trees Micaela M. Sousa a,b , Maria J. Melo a,b,∗ , A. Jorge Parola b , J. Sérgio Seixas de Melo c , Fernando Catarino d , Fernando Pina b, Frances E.M. Cook e, Monique S.J. Simmonds e, João A. Lopes f a Department of Conservation and Restoration, Faculty of Sciences and Technology, New University of Lisbon, 2829-516 Monte da Caparica, Portugal b REQUIMTE, CQFB, Chemistry Department, Faculty of Sciences and Technology, New University of Lisbon, 2829-516 Monte da Caparica, Portugal c Department of Chemistry, University of Coimbra, P3004-535 Coimbra, Portugal d Botanical Garden, University of Lisbon, Lisbon, Portugal e Royal Botanic Gardens, Kew, Richmond, Surrey TW9 3AB, UK f REQUIMTE, Servic¸ o de Química-Física, Faculdade de Farmácia, Universidade do Porto, Rua Aníbal Cunha 164, 4099-030 Porto, Portugal article info abstract Article history: A simple and rapid liquid chromatographic method with diode-array UV–vis spectrophotometric detec- Received 20 May 2008 tion has been developed for the authentication of dragon’s blood resins from Dracaena and Daemonorops Received in revised form 28 August 2008 trees. Using this method it was discovered that the flavylium chromophores, which contribute to the red Accepted 3 September 2008 colour of these resins, differ among the species and could be used as markers to differentiate among Available online 7 September 2008 species. A study of parameters, such as time of extraction, proportion of MeOH and pH, was undertaken to optimise the extraction of the flavyliums. This method was then used to make extracts from samples Keywords: of dragon’s blood resin obtained from material of known provenance. From the samples analysed 7,6- Dragon’s blood dihydroxy-5-methoxyflavylium (dracorhodin), 7,4-dihydroxy-5-methoxyflavylium (dracoflavylium) and Red dyes Flavylium chromophores 7,4 -dihydroxyflavylium were selected as species markers for Daemonorops spp., Dracaena draco and Dra- Dracaena caena cinnabari, respectively. The chromatograms from these samples were used to build an HPLC-DAD Daemonorops database. The ability to discriminate among species of dragon’s blood using the single marker compounds Species markers was compared with a principal components analysis of the chromatograms in the HPLC-DAD database. The results from the HPLC-DAD method based on the presence of these flavylium markers was unequivocal. The HPLC-DAD method was subsequently applied to 37 samples of dragon blood resins from the historical samples in the Economic Botany Collection, Royal Botanic Gardens, Kew. The method identified anomalies in how samples in this collection had been labelled. It is clear that the method can be used to evaluate the provenance of samples used in different areas of cultural heritage. It also could be used to monitor the trade of endangered species of dragon’s blood and the species being used in complex formulations of traditional Chinese medicine. © 2008 Elsevier B.V. All rights reserved. 1. Introduction the over exploitation of Dracaena, species of Daemonorops, Cro- ton and Pterocarpus were used as substitutes [5]. The red resin Dragon’s blood is a red resin obtained from species of Dra- is collected from natural exudates that appear in injured areas caena (Dracaenaceae) [1,2], Daemonorops (Palmae) [3,4], Croton on the stem and branches of Dracaena spp. or from a brittle (Euphorbiaceae) and Pterocarpus (Fabaceae) [5]. It has been used red layer formed outside the scaly fruits of Daemonorops spp. for centuries for medicinal [6] and artistic purposes [7].Itis [8]. thought that dragon’s blood was originally produced from species Species of Dracaena used as dragon’s blood included D. draco of Dracaena, especially the dragon tree Dracaena draco. But due to (L.) L. from Madeira, Canary, Cape Verde archipelagos [9], Dracaena cinnabari Balf.f. endemic to Socotra [10], Dracaena ombet Kotschy & Peyr. (synonym Dracaena schizantha Baker) from North-East ∗ tropical Africa and western Arabian peninsula [11] and Dracaena Corresponding author at: Department of Conservation and Restoration, Faculty tamaranae Marrero Rodd., R.S. Almeira & M. Gonzales-Martin of Sciences and Technology, New University of Lisbon, Quinta da Torre, 2829-516 Monte da Caparica, Portugal. Fax: +351 212948322. [12] from Canary Islands. Of these sources, the most frequently E-mail address: [email protected] (M.J. Melo). traded samples of dragon’s blood in Europe were obtained from 0021-9673/$ – see front matter © 2008 Elsevier B.V. All rights reserved. doi:10.1016/j.chroma.2008.09.007 154 M.M. Sousa et al. / J. Chromatogr. A 1209 (2008) 153–161 Table 1 [22,23–27]. In this paper when reference is made to the flavylium Structures for the flavylium compounds responsible for the red colour in dragon’s chromophore in dragon’s blood resin, it is considered to be present blood resins from species of Daemonorops and Dracaena as the red quinoid base [22]. Because compounds with a flavylium chromophore have not been found in the red resins or exudates from the species of Croton and Pterocarpus used as dragon’s blood Dracorhodin [5] they were not studied in this paper. The fact that different flavylium chromophores can be found in samples of Daemonorops [21] and Dracaena draco [23] suggests that these chromophores could be used as markers to differentiate among species. In order to test this hypothesis 47 samples, rep- resentative of three of the most commonly traded dragon’s blood sources in Europe, Dracaena draco, D. cinnabari and Daemonorops Dracorubin draco, were characterised by HPLC-DAD and selected flavylium chromophores were tested as species markers. The results were subsequently applied to 37 samples of dragon’s blood labelled as Daemonorops draco, Daemonorops sp., Dracaena cinnabari, D. draco, D. schizantha and Dracaena sp. from the Economic Botany Collec- tion, Royal Botanic Gardens, Kew (EBC). The EBC contains perhaps the largest and most reliably identified assemblage of dragon’s Dracoflavylium blood resins dating from the 19th century, that were donated by Sir Isaac Bailey Balfour, the Pharmaceutical Society of Great Britain and others [8]. This is the first report of flavylium compounds being used as markers to identify the species origin of dragon’s blood resins. 7,4 -Dihydroxy-flavylium 2. Experimental The chemical structures correspond to the quinoid bases. 2.1. Extraction methods Samples of commercial dragon’s blood resins (Zecchi-Colori e D. cinnabari and D. draco [8,5]. Because of over exploitation both Belli Arti, Florence, Italy) and Dracaena draco collected in Madeira, these species are currently regarded as Vulnerable in the IUCN Portugal were extracted using different extraction parameters. The Red List of Threatened Species [13]. Of the species of Daemonorops parameters studied were: (i) extraction time with 2, 5, 10, 60 and [14] that are sources of dragon’s blood, Daemonorops draco (Willd.) more than 60 min; (ii) solvent polarity using water:methanol solu- Blume (synonym Daemonorops propinqua Becc.) is now grown com- tions, with MeOH in the following percentages (v/v) 100, 75, 50 and mercially for the production of dragon’s blood [5] and is distributed 0%; (iii) pH with 1, 6–7 and >7. After the optimization of a selected from Thailand, to Sumatra and Borneo [15]. Dragon’s blood from parameter, the best result obtained for that parameter was applied Daemonorops draco is imported into China from South-East Asia to the samples. for use in traditional Chinese medicine [16–18], but sometimes Each sample weighed circa 0.2 mg. The samples were placed local species are used including Dracaena cochinchinensis (Lour.) in 1.5 mL Eppendorf tubes (Nirco, Spain) and 400 ␮L of extrac- S.C. Chen (China, S.W. Guangxi to S. Yunnan, to Indochina), Dracaena tion solution was added; the tubes were capped and kept at 25 ◦C, angustifolia Roxb (tropical and subtropical Asia to North Australia mechanical stirring, when necessary. Finally the samples were including Taiwan, Guangdong and Yunnan) and Dracaena cambodi- filtered with 0.45 ␮m Acrodisc syringe filters (Macherey-Nagel, ana Pierre ex Gagnep. (South Hainan to Indochina) [19]. Species Düren, Germany) and analysed by HPLC-DAD. Once the optimal of Croton and Pterocarpus were not usually used historically as extraction method had been developed then it was applied to the dragon’s blood in Europe and Asia, although the use of dragon’s experimental samples. blood from species of Croton has become common in the Americas [5] and could be entering the trade in Europe. Compounds in dragon’s blood resins that could be associ- 2.2. Resin samples ated with the red colour were studied by Brockmann and Junge [20], who attributed the colour to a flavylium, dracorhodin The initial tests to evaluate the HPLC method were undertaken (Table 1), which could be considered as belonging to the group on (i) 33 samples of Dracaena draco obtained from the Jardim of compounds known as anthocyanins. Dracorhodin (7-hydroxy-5- Botânico da Ajuda (Lisbon, Portugal); Jardim Botânico de Lisboa methoxy-6-methylflavylium) was isolated and characterised from (Lisbon, Portugal); Jardim Botânico da Madeira (Madeira, Portu- a commercial source of powdered dragon’s blood resin that was gal); Núcleo de dragoeiros das Neves (Madeira, Portugal); other probably obtained from a species of Daemonorops [21]. More places/gardens in Lisbon and Madeira (Portugal) and from Cape recently another flavylium, called dracoflavylium (7,4-dihydroxy- Verde (Santo Antão, Cape Verde). (ii) Twelve samples of Dracaena 5-methoxyflavylium) (Table 1) was isolated and characterized from cinnabari of which 11 from Socotra were made available by Jindrich D. draco [22]. Pavlis and one was purchased from Kremer (Aichstetten, Germany).
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