Journal of Natural Prodrcrts Val. 5 5 , No. 1 , p p . 122-125, January 1992
122
NARCISSUS ALKALOIDS, XIV. (+)-8-O-ACETYLHOMOLYCORINE AND VASCONINE, TWO NOVEL ALKALOIDS FROM NARCISSUS VASCONICUS JAUMEBASTIDA,CARLESC O D I N A ,FRANCESC ~ VILADOMAT,
Dqartament de Prohctes Naturals, Facultat de Fa-a MARIORUBIRALTA,
kbwatwi de Quimica Organica,Fanrltat de F a d i a , Universitatde Barcelona, 08028 BaKelona, Catalonia,Spain JEAN-CHARLES QUIRION,
lnstitut de Cbimie des Substances Naturelles, C . N . R . S . ,91 198 Gifsur-Yvette Cedex, France and BERNARDWENIGER
Lahatoire de Pbatmarognosie, FacultC de Pbatmucie, 67401 Illkircb C&,
France
bsTRAcr.-From the MeOH extract of the whole plants ofNarczssw vascunuus, two previously unreported alkaloids, (+)-8-0-acetylhomolycorine{l)and vasconine 121, have been isolated. The well-known alkaloids (-tlycorine and (+)-homolycorine were also present.
During the course of our chemical investigations on Narcissus alkaloids, we have studied Narcissus uasconicus Fdet. Casas (Amaryllidaceae), a new recently described species growing in Spain (2). No work on the chemical constituents of this plant has been reported so far. The present investigation led to the isolation and structure elucidation of two novel alkaloids, (+)-8-0-acetylhomolycorine E l ] and vasconine E21, along with the well-known alkaloids (-)-lycorine and (+)-homolycorine. Separation and isolation of individual compounds from the MeOH extract of the fresh aerial parts and bulbs of N . uasconicus followed the steps described in the Experimental section. Each alkaloidcontaining fraction was separated by a combination of cc and preparative tlc, and four alkaloids were thus obtained. Extract A yielded (+)-homolycorine, extract C was found to contain (-)lycorine and (+)-8-O-acetylhomolycorine [l],and extract D afforded the alkaloid vasconine 127 as well as additional (-)lycorine.
Compound 1 was obtained as a white crystalline solid, with hrms showing the molecular formula CI9H,,NO5 and { ~ ] * O D + 7 0 . 4 (EtOH, c = O . 5 4 ) . The eims showed a base peak at m/z 109, which is characteristic of the Amaryllidaceae alkaloids of the homolycorine series ( 3 ) . The low abundance of the molecular ion at mlz 343 (
