This work has been digitalized and published in 2013 by Verlag Zeitschrift für Naturforschung in cooperation with the Max Planck Society for the Advancement of Science under a Creative Commons Attribution 4.0 International License. Dieses Werk wurde im Jahr 2013 vom Verlag Zeitschrift für Naturforschung in Zusammenarbeit mit der Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. digitalisiert und unter folgender Lizenz veröffentlicht: Creative Commons Namensnennung 4.0 Lizenz. Two New Eudesmane Alcohols from Jasonia glutinosa Raquel Sánchez-Martínez3, Lucinda Villaescusa-Castillo3, Manuel Bernabéb and Ana Marí a Díaz-Lanza3* a Laboratorio de Farmacognosia, Departamento de Farmacologfa, Facultad de Farmacia, Universidad de Alcala de Henares, 28805 Alcala de Henares, Madrid, Spain b Departamento de Qui'mica Orgänica Biolögica, Instituto de Qui'mica Orgänica General (C. S. I.C), Juan de la Cierva, 3, 28006-Madrid, Spain. Fax: 918854679, E-mail: tfamdl@far- ma.alcala.es * Author for correspondence and reprint requests Z. Naturforsch. 55 c, 693-696 (2000); received April 3/May 15, 2000 Asteraceae, Eudesmane Alcohols, Jasonia glutinosa Two new sesquiterpene alcohols have been isolated from the aerial parts of Jasonia glu tinosa D. C. The structure of these sesquiterpenes were characterized by ID and 2D NMR techniques (DQCOSY, TOCSY, NOESY, HMQC and HMBC) as (llfi)-eudesm-4-en-ll,12- diol and (ll/?)-eudesmane-5a,ll,12-triol. Introduction Jasonia glutinosa D.C, (Chiliadenus saxatilis, Cass.) (Brullo, 1979) (Chiliadenus glutinosus (L) Fourr.) (Greuter et al ., 1989; Merxmüller et al., 1977) is an annual plant occurring in the Mediter ranean littoral area of the Iberian Peninsula, South of France and Malta. It is named “rock tea“ and it is used in spanish traditional medicine as an antispasmodic, anticatarrhal, antihypertensive, hemostatic, antiseptic, antifungic and antiinflama- tory drug (Arteche et al., 1998). Previous phytochemical investigations on J. glu tinosa have revealed the presence of sesquiterpene alcohols (Pacual et al, 1978; Villaescusa-Castillo et al., 1995; Pascual et al., 1980). We report here the isolation and characterization of two new eudes mane alcohols from this species. Results and Discussion The acetone/water extract of aerial parts of J. glutinosa was fractionated by a silica gel column to give two fractions, from which further purifica tion by medium pressure liquid chromatography (MPLC) yielded compounds 1 (5 mg) and 2 (21 mg). The mass spectrum of 1 gave a [M]+ ion at m/z 238, corresponding to a molecular formula C15H260 2. The high resolution 'H-NMR spectrum in methanol-^ contained an AB system centered at 3.44 (J = 11.2), characteristic of a CH2 group linked to an oxygen atom, a multiplet at 6 2.71 and three methyl singlets (6 1.60, 1.08, and 1.02), being the first of them slightly broadened by long range couplings. These couplings and the chemical shift strongly suggested the presence of a methyl group attached to a double bond. The 13C-NMR spectrum of 1 gave 15 signals, and confirmed the occurrence of a double bond (peaks at 6 136.2 and 125.4). The absence of ethylenic protons indicated that it was a tetra-substituted double bond. The multiplicities of the individual 13C peaks, determined using the DEPT (distor tionless enhancement by polarization transfer) pulse sequence, indicated the presence of three methyl, seven methylene, and one methine groups, and four quaternary carbons. The assignment of proton and carbon signals was achieved from DQCOSY and 2D- TOCSY (HOHAHA) (mixing time = 80 ms) experiments, and also from 1H-13C heteronuclear multiple quantum (HMQC) and multiple bond correlations (HMBC). The data ob tained have been gathered in Table I. It was also possible the measurement of some of the coupling constants. For instance, H-7 contained two large couplings (J =12.5 Hz), which indicated an axial proton. All these data, together with the rest of spectroanalytical results, allowed to propose the structure of 1 as (ll/?)-eudesm-4,5-en-ll,12-diol. The structure of compound 1, now found in J. glutinosa, has been reported as obtained in inter mediate steps in partial syntheses of Kudtdiol and Kudtriol (Pascual et al., 1980; Harapanhalli, 1988). The [a]D and 'H-NMR spectral values were prac- 0939 - 5075/2000/0900 - 0693 $ 06.00 © 2000 Verlag der Zeitschrift für Naturforschung. Tübingen ■ www.znaturforsch.com • D