Narcissus and Daffodil

8 Narcissus and other Amaryllidaceae
as sources of galanthamine
O.A. Cherkasov and O.N. Tolkachev
INTRODUCTION
The Amaryllidaceae family contains 65 genera and over 860 species. Amaryllidaceae
species are widely distributed in the tropical, sub-tropical and temperate
zones of both hemispheres, and a vast diversity of species is characteristic of
the flora of the South African Cape region, South and Central America and the
Mediterranean coasts. They possess highly decorative characteristics, and have
been used from ancient times in floriculture and medicine (Artyushenko, 1970;
Khamidkhodzhaev, 1984).
Amaryllid plants are very important as ornamentals. They are popular for growing
in parks and gardens, as farm crops and as indoor and greenhouse plants for
winter and spring colour (Artyushenko, 1963; Tsytsin, 1960; Petrov, 1975).
All Amaryllidaceae are rich in alkaloids, the principal biologically active components
of plant extracts. Today over 200 alkaloids have been isolated from plants
of this family. Incidents of animals being poisoned by Amaryllidaceae, due to the
alkaloids contained, have been recorded in the literature: poisonous examples
include Galanthus and Leucojum species (Gusynin, 1955). The presence of alkaloids
in plants is believed to be a protective adaptation, which in Amaryllidaceae is
connected with the seasonal cycle of development, many species growing in early
spring when other genera are only just starting to grow.
Amaryllidaceae have attracted the attention of scientists as the sources of novel
compounds, including potentially valuable alkaloids of medicinal importance. The
chemistry of Amaryllidaceae alkaloids has been reviewed in several reviews and
monographs (Cook and Loudon, 1952; Cherkasov, 1977; Döpke, 1976, 1978;
Wildman, 1960, 1968; Fuganti, 1975; Grundon, 1984, 1985, 1987; Jeffs, 1990;
Lewis, 1990, 1997; Medvedeva et al., 1994; Abduazimov, 1993; Polt, 1996; Ruan,
1988; Yunusov, 1981). The absolute configuration and ring conformation of
(–)-galanthamine have recently been determined by crystallographic methods
(Peeters et al., 1997).
Galanthamine (Figure 8.1), also known as Galanthin and Nivaline Jilkon (Negwer,
1978), is the most important pharmaceutically active compound among the
Amaryllidaceae alkaloids, and it is used in medicine as the hydrobromide. It is
an anticholinesterase agent of low toxicity used in medicine for the treatment of
myasthenia, myopathy, neuritis, residual phenomena after poliomyelitis anterior
acuta (infantile paralysis), psychogenic ‘spinal impotence’, spastic pareses and
progressive muscular dystrophy, and as the antagonist of muscular relaxants in