Chemotaxonomy of Gonospermum and related genera Jorge Triana a , José Luis Eiroa a , Juan José Ortega a , Francisco León b,d , Ignacio Brouard b , Juan Carlos Hernández b , Francisco Estévez c,d , Jaime Bermejo b, * a Departamento de Química, Universidad de Las Palmas de Gran Canaria, Campus de Tafira, 35017 Las Palmas de Gran Canaria, Canary Islands, Spain b Instituto de Productos Naturales y Agrobiología-C.S.I.C.-Instituto Universitario de Bio-Orgánica ‘‘Antonio González”, Universidad de La Laguna, Av. Astrofísico F. Sánchez 3, 38206 La Laguna, Tenerife, Spain c Departamento de Bioquímica, Facultad de Ciencias de la Salud, Universidad de las Palmas de Gran Canaria, 35016, Las Palmas de Gran Canaria, Spain d Instituto Canario de Investigación del Cáncer (ICIC), plaza Sixto Machado 3, 38009, Tenerife, Spain article info Article history: Received 27 October 2009 Received in revised form 17 December 2009 Available online 22 January 2010 Keywords: Gonospermum fruticosum Gonosperminae Asteraceae Chemotaxonomy Sesquiterpene lactones Sesquiterpene alcohols abstract Aerial parts of Gonospermum fruticosum collected at several locations in the Canary Islands afforded, in addition to known compounds, four sesquiterpene alcohols related to costol and a sesquiterpene lactone, whose structures were established on the basis of their spectroscopic data and chemical transformations. Except for Gonospermum species collected on the island of Tenerife, those collected on the island of El Hierro and, in a previous study those from La Gomera, contain sesquiterpene lactones that can be used as chemotaxonomic markers confirming the inclusion of Gonospermum, Lugoa, and species of Tanacetum endemic to the Canary Islands in a genus that does not support the monophyly of Gonosperminae. Ó 2009 Elsevier Ltd. All rights reserved. 1. Introduction Gonosperminae is one of the 12 presently recognized subtribes of Anthemideae (Asteraceae) and provides one of the putative examples of discontinuous distribution between the Canary Islands and South Africa. As occurred with other members of the Anthemi- deae tribe, the taxonomic classification of these species has been controversial since the established morphological differences are of little taxonomic value. The Gonosperminae (3 genera, 15 species), comprising the three genera Gonospermum Less (Canary Islands), Lugoa (Canary Islands), and Inulanthera (South Africa), were considered a monophyletic group (Bremer and Humphries, 1993). Inulanthera was initially in- cluded in the South African genus Athanasia and subsequently as- signed genus level based on chemical and morphological evidence, allowing a connection to be established between the Ca- narian and South African genera (Källersjö, 1985). However, the phylogenetic analysis of ITS (Internal Transcribed Spacer) se- quences reveals that the Canarian genera are not connected to Inu- lanthera and does not support Gonosperminae monophyly. Rather, the Canarian Gonosperminae seem to be more closely related to the Tanacetum species endemic to the islands than to Inulanthera (Francisco-Ortega et al., 2001), and it has also been recommended that Inulanthera be assigned to subtribe Ursiniinae (Oberprieler et al., 2007). The geographical distribution in the Canary Islands of the sev- eral Gonospermum and Lugoa species is quite different. Whereas Gonospermum fruticosum (Link) Less is widely distributed and is found on three of the islands (Tenerife, La Gomera and El Hierro), Gonospermum gomerae Bolle is restricted to La Gomera, Gonosper- mum canariense (DC.) Less to La Palma, Gonospermum elegans (Cass.) Less to El Hierro, and Lugoa revoluta (Link) DC. to Tenerife, while the three endemic Tanacetum species of Gran Canaria are lo- cated in very specific areas of Gran Canaria (Bramwell and Bram- well, 2001). Based on cytogenetic studies of the nine endemic taxa of Gono- spermum Less, Lugoa DC and Tanacetum L. in the Canary Islands it has recently been proposed that all three taxa be included in the endemic genus Gonospermum (Febles, 2008). Previous chemical study of the Canarian endemics Tanacetum ferulaceum (González et al., 1990), Tanacetum ptarmiciflorum (Gon- zález et al., 1992a), as well as G. canariense (Triana et al., 2000), G. elegans (Triana et al., 2003), G. gomerae and G. fruticosum collected in La Gomera (Triana et al., 2008) and L. revoluta (Triana et al., 2001) showed a high content of similar sesquiterpene lactones (Table 1). However, a chemical study of G. fruticosum collected on Tenerife (González et al., 1992b) afforded sesquiterpene alcohols rather than lactones and thus, in view of the wide distribution of this species, a new study was undertaken using samples from 0031-9422/$ - see front matter Ó 2009 Elsevier Ltd. All rights reserved. doi:10.1016/j.phytochem.2009.12.013 * Corresponding author. Tel.: +34 922 318583; fax: +34 922 318571. E-mail address: jbermejo@ull.es (J. Bermejo). Phytochemistry 71 (2010) 627–634 Contents lists available at ScienceDirect Phytochemistry journal homepage: www.elsevier.com/locate/phytochem