Phenylpropanoids from Thapsia transtagana Abderrahmane Saouf b , Francisco M. Guerra a , Juan J. Rubal a , Zacarı ´as D. Jorge a , Mohamed Akssira b , Fouad Mellouki b , F. Javier Moreno-Dorado a , Guillermo M. Massanet a, * a Departamento de Quı ´mica Orga ´ nica, Facultad de Ciencias, Universidad de Ca ´ diz, Apartado 40, 11510 Puerto Real, Ca ´ diz, Spain b Faculte ´ des Sciences et Techniques, Universite ´ Hassan II Mohammedia, LCBA, UFR C35/97, BP 146 Mohammedia 20650, Morocco Received 24 October 2005; received in revised form 25 January 2006; accepted 27 January 2006 Available online 15 March 2006 Abstract Five phenylpropanoids have been isolated from the roots of Thapsia transtagana. Their structures have been elucidated by spectro- scopic means. Ó 2006 Elsevier Ltd. All rights reserved. Keywords: Phenylpropanoids; Thapsia transtagana; Umbelliferae 1. Introduction Thapsia is a complex genus not only from the taxonom- ical point of view, but also from the nature of the metabo- lites isolated and the distribution in its species (Christensen et al., 1997). Although Tutin described in 1968 in Flora Europaea only three species (Tutin, 1968), new species have later been characterized or differentiated (Pujadas-Salva ´ and Plaza-Arregui, 2003). Thapsia transtagana Brot. (Api- aceae, tribe Laserpitieae) is a perennial herb of 140–180 cm of height and robust stem, distributed along the Western Mediterranean area (Pujadas and Rosello ´ , 2003). Although initially T. transtagana Brot. was classified as synonymous of T. garganica, Christensen et al. proposed their consider- ation as different species (Smitt et al., 1995). Previous stud- ies of T. transtagana have provided thapsigargin-related guaianolides (Rasmussen et al., 1981; Avato et al., 1993), and we recently have reported the isolation of a new class of compounds that have been generically named as tran- staganolides (Saouf et al., 2005). In our search for new natural products in umbefellifer- ous species of both sides of the Gibraltar Strait, we have examined the roots of T. transtagana collected in Bouznika (Morocco). In addition to thapsitranstagin, we have iso- lated five new metabolites with a phenylpropanoid structure. 2. Results and discussion The roots of T. transtagana were extracted with dichlo- romethane in a Soxhlet apparatus yielding an oily residue that was purified by column chromatography using increasing polarities of EtOAc/hexanes mixtures affording compounds 1 (90 mg), 3 (30 mg), 4 (60 mg), 5 (12 mg) and 6 (7 mg) (Fig. 1). Compound 1 showed the molecular ion in its HREIMS spectrum at m/z 350.1365 corresponding to a molecular for- mula of C 18 H 22 O 7 , which accounted for eight degrees of unsaturation. This unsaturation degree was in agreement with the observation in the NMR and IR spectra of the sig- nals corresponding to an aromatic ring, an additional ring formed by methylenedioxy group, two carbonyl groups belonging to two ester groups and two vinylic carbons. 0031-9422/$ - see front matter Ó 2006 Elsevier Ltd. All rights reserved. doi:10.1016/j.phytochem.2006.01.032 * Corresponding author. Tel.: +34 956 016366; fax: +34 956 016288. E-mail address: g.martinez@uca.es (G.M. Massanet). www.elsevier.com/locate/phytochem Phytochemistry 67 (2006) 800–804 PHYTOCHEMISTRY