Narcissus and Daffodil

15 Screening of Amaryllidaceae
for biological activities:
acetylcholinesterase inhibitors
in Narcissus
Kornkanok Ingkaninan, Hubertus Irth and Rob Verpoorte
INTRODUCTION
Narcissus are well-known cultivated plants belonging to the Amaryllidaceae family.
Tyler et al. (1988) classified them as poisonous plants, since ingestion of narcissus
bulbs produces severe gastroenteritis and nervous symptoms. Narcissus plants
contain similar alkaloids which can also be found in other members of the Amaryllidaceae.
The Amaryllidaceae alkaloids have been shown to possess a wide spectrum
of biological activities such as anticholinergic and analgesic (Harvey, 1995),
antimalarial (Likhitwitayawuid et al., 1993), antiviral (Gabrielsen et al., 1992; Lewis,
1996) and anti-neoplastic (Jimenez et al., 1976; Ghosal et al., 1988; Pettit et al.,
1990, 1993). However, galanthamine is so far the only Amaryllidaceae alkaloid
that has gained a wide spread commercial application because of its inhibitory
activity for acetylcholinesterase (AChE).
GALANTHAMINE
Galanthamine is a tertiary amine alkaloid belonging to the phenanthrene group.
It was first isolated from bulbs of Caucasian snowdrop, Galanthus woronowi, in 1952
(Proskurnina and Yakovleva, 1952). It has also been found in various species of
Narcissus (Paskov, 1986; Bastida et al., 1990). The compound was first applied for
medical purpose by Bulgarian and Russian researchers in the 1950s. In 1955,
Mashkovskii reported that galanthamine could reverse tubocurarine-induced
muscle paralysis and potentiate the actions of acetylcholine on skeletal muscles. It
was then used as a potent natural cholinergic substance showing strong AChE
inhibitory activity in both the central and peripheral system, and for the reversal
of the neuromuscular blockade caused by various curare-like agents (Irwin and
Smith, 1960; Cozanitis, 1971; Baraka and Cozanitis, 1973; Cozanitis and Rosenberg,
1974; Krivoi, 1988). This drug has been available for clinical use as Nivalin ®
(Pharmachim, Sofia, Bulgaria) and Galanthamine ® (Medexport, Moscow, USSR).
It was not until 1986, after the cholinergic hypothesis of Alzheimer’s disease was