8th International Electronic Conference on Synthetic Organic Chemistry. ECSOC-8. 1-30 November 2004. http://www.lugo.usc.es/~qoseijas/ECSOC-8/  

[C008]
Universidade de Santiago de Compostela

Mesembrine alkaloids from Narcissus triandrus L.

 VISIT THE CITY OF LUGO

 

Julio A. Seijas,a* M. Pilar Vázquez-Tato,a* M. Teresa Linares,a Pablo Ramil-Rego,b M. Inmaculada Bujánb

 

aDepartamento de Química Orgánica. Universidad de Santiago de Compostela. Facultad de Ciencias. Campus de Lugo. Aptdo. 280. 27080-Lugo. Spain
bDepartamento de Biología Vegetal. Universidad de Santiago de Compostela. Campus de Lugo. Aptdo. 280. 27080-Lugo. Spain.

 

 

    Narcissus plants are known to contain amaryllidaceae alkaloids[1]. In fact there is a large number of phytochemical studies on Narcissus to check their use as potential source of galanthamine, an alkaloid with biological properties as healing in Alzheimer's disease, probably due to its acetylcholinesterase and muscarinic activity[vvv]. As a part our studies on the phytochemistry of endangered plants from Galicia (NW Spain), here we present the results for Narcissus triandrus L. collected from Serra do Xistral (fig. 1).

 

Figure 1

    N. triandrus L. has its habitat extended over N.W. France, Portugal and Spain. To our knowledge[2] there is only one phytochemical study on this plant (garden varieties)[3], where haemanthamine, lycorenin, lycorin, homolycorin, galanthamin and tazetin are identified.
    The aereal parts of Narcissus triandrus were extracted with methanol in a Soxhlet apparatus. The basic extracts were purified by column chromatography with silica gel as adsorbent. Three mesembrine-type of alkaloids were identified: mesembrine (1),  mesembrenol (2) and  mesembrenone (3), this last one in a very small amount. All were characterized on the  basis of their spectroscopic properties.However, none of the previously described alkaloids were found.


 

Figure 2 

1H NMR spectrum
mesembrine mesembrenol

  Up to now only three  amaryllidaceae plants (Hymenocallis arenicola[4], Crinun oliganthum[5] and Narcissus pallidulus,[6]) were described to have Sceletium-type alkaloids (Aizoeceae).

    Mesembrine and analog compounds are serotonin-uptake inhibitors[7] and can be used for the treatment of depressive states, psycological or psychiatric disorder with an anxiety component, alcohol and drug dependence, bulimia nervosa and obsessive-compulsive disorders. Those compounds are also the main component of Sceletium plants that have been used in traditional medicine by Khoisan of South Africa to prepare "kougoed" a fermentative preparation with narcotic-anxyolitic properties.[8]

Acknowledgements


XUNTA DE GALICIA for financial support: PGIDT01PXI26203PR and PR405 A 098/59-0.
 

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2.- SciFinder, 29th October 2004

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4.- Doepke, W.; Sewerin, E.; Trimino, Z. Z.  Chem. 1980, 20, 298-299, Chem. Abstr. 94:30972 1981.

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8.- Smith, M. T.; Crouch, N. R.; Gericke, N.; Hirst, M. J. Ethnopharmacology 1996, 50, 119-130. Smith, M. T.; Field, C. R.; Crouch, N. R.; Hirst, M. Pharm. Biol.1998, 36, 173-179.