Anticancer evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives
- 1.1k Downloads
Plants of the Amaryllidaceae family have been under intense scrutiny for the presence of the specific metabolites responsible for the medicinal properties associated with them. The study began in 1877 with the isolation of alkaloid lycorine from Narcissus pseudonarcissus and since then more than 100 alkaloids, exhibiting diverse biological activities, have been isolated from the Amaryllidaceae plants. Based on the present scientific evidence, it is likely that isocarbostyril constituents of the Amaryllidaceae, such as narciclasine, pancratistatin and their congeners, are the most important metabolites responsible for the therapeutic benefits of these plant species in the folk medical treatment of cancer. Notably, Narcissus poeticus L., used by the ancient Greek physicians, is now known to contain about 0.12 g of narciclasine per kg of fresh bulbs. The focus of the present research work is the chemistry and biology of these compounds as specifically relevant to their potential use in medicine. In particular, the anticancer evaluation of lycorine, narciclasine as well as of other Amaryllidaceae alkaloids and their synthetic derivatives are presented in this paper. The structure–activity relationships among some groups of Amaryllidaceae alkaloids will be discussed.
KeywordsMedicinal plants Amaryllidaceae Alkaloids Lycorine Narciclasine Anticancer activity
This work was carried out within the project “Programma di Scambi Internazionali con Università ed Istituti di Ricerca Stranieri per la Mobilità di Breve Durata di Docenti, Ricercatore e Studiosi”, which is financially supported by the Università di Napoli Federico II anno finanziario 2008. Contribution DISSPAPA 181.
- Cook JW, Loudon JD (1952) The alkaloids. Academic Press, New YorkGoogle Scholar
- Evidente A, Motta A (2001) Bioactive metabolites from phytopathogenic bacteria and plants. In: Atta-ur-Rahaman (ed) Studies in natural products chemistry, vol 26. Elsevier, Amsterdam, pp 581–628 (and references therein cited)Google Scholar
- Evidente A, Iasiello I et al (1984) An improved method for large-scale preparation of lycorine. Chem Ind 348–349Google Scholar
- Evidente A, Andolfi A et al (2005) Minor alkaloids from Clivia nobilis Regel. Alex J Pharm Sci 19:49–53Google Scholar
- Evidente A, Kireev AS et al (2009) Biological evaluation of structurally diverse Amaryllidaceae alkaloids and their synthetic derivatives: discovery of novel leads for anticancer drug design. Planta Med (in press)Google Scholar
- Nagakawa Y, Uyeo S et al (1956) The double bond in lycorine. Chem Ind 1238–1239Google Scholar
- Pettit GR, Melody N et al (1994) Antineoplastic agents. 321. Synthesis of 10b-R-hydroxypancratistatin via narciclasine. J Chem Soc Chem Commun 2725–2726. doi: 10.1039/c39940002725
- Wildman WC (1960) The alkaloids. Academic Press, New YorkGoogle Scholar