Pergamon 0031-9422(94)00639-3 Phytochemistry, Vol. 38, No. 2, pp. 549-551, 1995 Copyright © 1995 Elsevier Science Ltd Printed in Great Britain. All rights reserved 0031-9422/95 $9.50 + 0.00 ALKALOIDS FROM NARCISSUS TORTUOSUS* JAUME BASTIDA,JUAN MARCOS FERNANDEZ, FRANCESC VILADOMAT,CARLESCODINA and GABRIELDE LA FUENTE~: Departament de Productes Naturals, Facultat de Farmficia, Universitat de Barcelona, E-08028 Barcelona, Spain; tInstituto de Productos Naturales y Agrobiologia, CPNO 'Antonio Gonzfilez', CSIC-Universidad de La Laguna, La Laguna, Tenerife, Spain (Received 7 March 1994) Key Word Index--Narcissus tortuosus; Amaryllidaceae; alkaloids; tortuosine; lycorine; 2DNMR spectroscopy. Abstract--Whole plants of Narcissus tortuosus were found to contain tortuosine and lycorine. Tortuosirm is reported for the first time and its structure was established by spectroscopic methods. INTRODUCTION Narcissus tortuosus, a species belonging to the Pseudonar- cissus section, is notable for its pale and beautifully symmetrical flowers, regularly twisted. Morphologically, it is separable from N. moschatus by its stronger growth and broader foliage, and by its larger and less concolo- rous flowers 1"21.Histological and caryological studies of N. tortuosus have been made recently I-3,4]. In the present paper, we describe the isolation and character- ization of tortuosine (1) and lycorine (2) from whole plants of this species. OMe 2 ,o I,o 114 7 6 11 12 RESULTS AND DISCUSSION The alkaloids were extracted by routine acid-base work-up procedures and after CC (see Experimental) 1 was isolated as yellow crystals. Its HR mass spectrum ([M] + m/z 296.1292) indicated the molecular formula ClsH~sNO 3 which was consistent with a phenantridin- ium structure. Support for this assumption was obtained by comparison with spectroscopic data of the anhydroly- corinium ion, one of the biosynthetic products of Amaryl- lis belladonna most inhibitory to murine 3PS leukaemia [51, and vasconine, a quaternary alkaloid isolated from N. vasconicus [61. The ~H and ~3CNMR spectra were assigned taking into account the correlations observed in 1HCOSY, HMQC [71, HMBC 181 and ROESY [91 experiments. The most characteristic signals of the ~H NMR spectrum (Table 1) were a one proton doublet at 58.13 (J = 1.4 Hz) assigned to H-1 and one broad singlet at 57.59 assigned to H-3, since they showed scalar coupling in the 1H COSY spectrum. Also, the ROESY showed a spacial correlation between H-1 and the one-proton signal at *Part 21 in the series 'Narcissus alkaloids'. For Part 20 see ref. [1]. PRY 38-2-5 OH HO...~ 2 68.34, and between H-1 and the methoxy group at 54.20, allowing us to assign those signals to H-10 and H-2', respectively. Moreover, in the 1H COSY spectrum, the H- 10 signal showed zig-zag coupling to H-6 at 69.55 1"101 and a NOE contour with the methoxy group at 34.33 (H- 9') in the ROESY spectrum. After that, the signals at 549