Narcissus and Daffodil

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Alkaloids of Narcissus 185 tered. When symptoms are severe, atropine sulphate is given by intravenous injection ( Junko et al., 1994). Some Narcissus species can produce harmful effects without being swallowed. Thus, species like N. bulbocodium must not be placed in confined spaces because the scent of the flowers, when present in any quantity, can produce headaches and even vomiting. The association of alkaloids with essential oils is found in oils of patchouli, juniper, orange and jonquil absolute (Maurer, 1994). In turn, N. pseudonarcissus shows irritant and allergenic properties on contact with animals and men (Bruynzeel, 1997; Bruynzeel et al., 1993; De Jong et al., 1998; Gonçalo et al., 1987; Güneser et al., 1996). The compounds responsible for the irritation are not known, but alkaloids are thought to be involved (Gude et al., 1988). Additionally, extracts of the bulbs, when applied to open wounds, can produce staggering, numbness of the whole nervous system and paralysis of the heart. The mucilage secreted by bulbs can also produce harmful effects in plant species such as rose, rice and cabbage, inhibiting seed germination and seedling growth (Bi et al., 1998; Van Doorn, 1998). Traditional medicinal usage Despite their lethal potential, the extracts of various narcissus plants have been used in traditional medicine to treat a variety of medicinal problems. This aspect is covered in Chapter 2 of this volume. Biological activities for extracts of Narcissus Several Narcissus extracts have shown the following activities: antiviral (Abou- Karam and Shier, 1990; Furusawa et al., 1973, 1975; Papas et al., 1973; Ramanathan et al., 1968; Suzuki et al., 1974; Vacik et al., 1979; Van den Berghe et al., 1978), prophage induction (Dornberger and Lich, 1982), antimicrobial (Dornberger and Lich, 1982; Ieven et al., 1979), antifungal (Chaumont and Senet, 1978; Chaumont et al., 1978), cytotoxic (Abou-Karam and Shier, 1990; Furusawa et al., 1973, 1980), antitumour (Furusawa et al., 1972, 1973, 1975; Papas et al., 1973; Suzuki et al., 1974; Wu et al., 1965), antimitotic (Ikram, 1983), hipotensive (Chiu et al., 1992), emetic (Wu et al., 1965), antifertility (Matsui et al., 1967), antinociceptive (Çakici et al., 1997), chronotropic (Chiu et al., 1992), pheromone (Keiser et al., 1975), plant growth inhibitor and allelopathic (Bi et al., 1998; Ceriotti, 1967; Chiu et al., 1992; Van Doorn, 1998). Biological and pharmacological activities of Narcissus compounds The compounds responsible for the majority of the above-mentioned activities are the alkaloids. However, the mannose-binding lectins have also received much interest recently (Barre et al., 1996; Van Damme et al., 1998). The different pharmacological and/or biological properties exhibited by the alkaloids from the genus Narcissus are shown in Table 6.4, but only some of the activities of a reduced number of these alkaloids are known. The most extensively studied effect is that of non-specific inhibition. The relationship of chemical structure
186 J. Bastida and F. Viladomat and biological activity is largely unknown (Chiu et al., 1992), and further studies of several alkaloids still remain to be done for therapeutic purposes. The best-studied alkaloids in this group are galanthamine, lycorine, narciclasine and pretazettine, which possess a diversity of pharmacological activities. Table 6.4 Biological and pharmacological activities of Narcissus alkaloids Alkaloid Activity References 10 caranine * Weak analgesic * Convulsant and hypotensive * Acetylcholinesterase inhibitor * Active against the murine P-388 lymphocytic leukaemia (as acetylcaranine) 53 crinamine * Powerful transient hypotensive in dogs * Respiratory depressant * Moderate antimalarial * Antimicrobial * Moderately active against murine Rauscher viral leukaemia * Cytotoxic against Molt 4 lymphoid and LMTK fibroblastic cell lines * Weak cytotoxic against HepG2 hepatoma 36 dubiusine * Cytotoxic against non-tumoural LMTK cells * Moderately active against Molt 4 lymphoma 69 galanthamine * Powerful analgesic as strong as morphine * Anticonvulsive * Hypotensive * Inductor of hypothermia in rat * Acetylcholinesterase inhibitor with peripheral and central pharmacological effects * Highly selective for acetylcholinesterase versus butyrylcholinesterase (more than 50-fold greater) * Centrally-acting acetylcholinesterase inhibitor which has shown potential for the treatment of Alzheimer’s disease * Attenuates or reverses cognitive deficits induced by drugs – and lesions – in animal models * Acts as noncompetitive nicotinic receptor agonist CHCD, 1996 Pettit et al., 1984 CHCD, 1996 Furusawa et al., 1980 Likhitwitayawuid et al., 1993 Weniger et al., 1995 Weniger et al., 1995 Bores et al., 1996 Chao et al., 1965 CHCD, 1996 Cozanitis, 1977 Cozanitis and Rosenberg, 1974 Cozanitis and Toivakka, 1978 Cozanitis et al., 1983 Fulton and Benfield, 1996 Ghosal et al., 1985b Han et al., 1992 Harvey, 1995 Kewitz, 1996 Mihailova and Yamboliev, 1986 Mihailova et al., 1985 Mihailova et al., 1987 Mihailova et al., 1989 Pereira et al., 1994 Radicheva et al., 1996 Riemann et al., 1994 Schuh, 1976 Storch et al., 1995 Suzuki et al., 1974
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Narcissus and Daffodil
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Narcissus and Daffodil The genus Na
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Contents Preface to the series vii
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Preface to the series There is incr
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Preface My interest in flower-bulb
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Acknowledgements I would like to th
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Gordon R. Hanks Crop and Weed Scien
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Figures 1.1 The effect of bulb stor
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Figures/Plates xvii 7.8 Accumulatio
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Figures/Plates of different segment
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2 G.R. Hanks Information about the
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4 G.R. Hanks (1999), and the polysa
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3 2 4 1 1 3 2 4 5 Flowering in 1976
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8 G.R. Hanks Figure 1.6 Diagrammati
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10 G.R. Hanks (Rees, 1969). When fl
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12 G.R. Hanks Figure 1.8 The relati
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14 G.R. Hanks root system of commer
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16 G.R. Hanks Cremer, M.C., Beijer,
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18 G.R. Hanks Roh, S.M. and Lee, J.
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20 A.C. Dweck Figure 2.1 The narcis
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22 A.C. Dweck Julians Hertfordshire
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24 A.C. Dweck Herefordshire, if daf
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26 A.C. Dweck the basis of an ancie
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28 A.C. Dweck Britten, J. and Holla
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3 Classification of the genus Narci
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(1) (2) (3)
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34 B. Mathew d. Section Jonquillae
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36 B. Mathew N. cyclamineus DC. Flo
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38 B. Mathew 1c. Section Ganymedes
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40 B. Mathew umbel, fragrant; peria
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42 B. Mathew recognition whatsoever
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44 B. Mathew Note: N. elegans shows
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46 B. Mathew ssp. praecox Gatt. and
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(1) (2) (3) (4)
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50 B. Mathew Table 3.1 Horticultura
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52 B. Mathew RHS (1958) The Classif
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54 G.R. Hanks grown for galanthamin
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56 G.R. Hanks such as drying stores
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Table 4.4 Areas of Narcissus cultiv
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60 G.R. Hanks Following planting in
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62 G.R. Hanks lost, resulting in th
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64 G.R. Hanks pathogen-tested nucle
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Figure 4.1 Mean monthly weather dat
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68 G.R. Hanks (as well as natural e
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70 G.R. Hanks compaction and its ef
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72 G.R. Hanks bulbs with base rot)
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74 G.R. Hanks Figure 4.3 Modern fro
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76 G.R. Hanks caution. Higher rates
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78 G.R. Hanks can also be prevented
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80 G.R. Hanks Figure 4.4 A typical
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82 G.R. Hanks Planting date The pra
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84 G.R. Hanks Hanks and Jones, 1986
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86 G.R. Hanks On sloping sites, gro
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88 G.R. Hanks Insecticide and nemat
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90 G.R. Hanks bulb growth, especial
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92 G.R. Hanks Figure 4.7 Changes in
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94 G.R. Hanks methods have been tes
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96 G.R. Hanks the boxes, exiting at
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98 G.R. Hanks usually collected in
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100 G.R. Hanks respond to ethylene
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102 G.R. Hanks using thiabendazole
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104 G.R. Hanks required for the eff
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106 G.R. Hanks and cross-cutting, s
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108 G.R. Hanks In practice, moulds
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110 G.R. Hanks that, with enterpris
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112 G.R. Hanks Balatková, V., Tupy
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114 G.R. Hanks (Narcissus pseudonar
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116 G.R. Hanks Flint, G.J. (1983) E
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118 G.R. Hanks Hanks, G.R. and Rees
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120 G.R. Hanks Khatib, K. al (1996)
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122 G.R. Hanks Luyten, I. (1935) Ve
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124 G.R. Hanks O’Neill, T.M., Man
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126 G.R. Hanks Ruamrungsri, S., Rua
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128 G.R. Hanks Thompson, P.A. (1977
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130 G.R. Hanks Williams, M. (1996)
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132 J.B. Briggs Table 5.1 Typical g
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Page 167 and 168: Table 6.1b Continued Alkaloid name
Page 169 and 170: Table 6.1d Tazettine type O O R1 R2
Page 171 and 172: Table 6.1f Continued MeO Alkaloid n
Page 173 and 174: Table 6.2 Continued Species* Alkalo
Page 183 and 184: 162 J. Bastida and F. Viladomat Tab
Page 193 and 194: Table 6.3 Continued Alkaloid* Formu
Page 195 and 196: Table 6.3 Continued Alkaloid* Formu
Page 197 and 198: 176 J. Bastida and F. Viladomat Tab
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Page 209 and 210: Table 6.4 Continued Alkaloid Activi
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Page 245 and 246: 224 C. Codina Kinetin As observed i
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236 C. Codina mg/g DW mg/g DW 1.4 1
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238 C. Codina mg/g DW mg/g DW 1.5 1
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240 C. Codina Hanks, G.R. and Jones
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8 Narcissus and other Amaryllidacea
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244 O.A. Cherkasov and O.N. Tolkach
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9 Studies on galanthamine extractio
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258 M. Kreh Table 9.1 Results of ga
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260 M. Kreh relation to the qualita
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262 M. Kreh Figure 9.3 Galanthamine
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264 M. Kreh 2.0 flower 2 1 3 4 0 10
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266 M. Kreh • High purity of the
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268 M. Kreh fraction of Narcissus
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H O MeO O MeO H H HO H (1) (3) + 2
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272 M. Kreh Gorinova, N.I., Atanass
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274 R.M. Moraes (Katz and Taneck, 1
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276 R.M. Moraes bulbs of many Narci
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278 R.M. Moraes Galanthamine conten
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280 R.M. Moraes Table 10.2 The effe
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282 R.M. Moraes years, a yield of 1
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284 R.M. Moraes Kosley, R.W., Jr.,
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11 Extraction and quantitative anal
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288 N.P.D. Nanayakkara and J.K. Bas
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Table 11.1 GC and HPLC procedures f
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Table 11.1 Continued References Det
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12 Synthesis of galanthamine and re
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306 V.N. Bulavka and O.N. Tolkachev
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13 Compounds from the genus Narciss
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334 D. Brown with neostigmine the a
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336 D. Brown Absorption Galanthamin
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338 D. Brown Metabolism and excreti
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340 D. Brown were internationally i
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342 D. Brown cortex and hippocampus
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344 D. Brown reasoned that the effi
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346 D. Brown Galanthamine causes br
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348 D. Brown (1994) go on to mentio
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350 D. Brown (Punto Toro and Rift V
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352 D. Brown Furusawa, E., Lum, M.K
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354 D. Brown Snorrason, E. and Stef
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356 D. Brown examination of a brain
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358 D. Brown A successful cholinerg
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Table 14.2 Summary of human trials
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362 D. Brown statistically signific
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364 D. Brown ( Jann, 1998); see Tab
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366 D. Brown REFERENCES Bartus, B.T
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368 D. Brown Wilcock, G.K., Scott,
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370 K. Ingkaninan, H. Irth and R. V
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16 Narcissus lectins Els J.M. Van D
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382 E.J.M. Van Damme and W.J. Peuma
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17 Narcissus in perfumery HISTORY C
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394 C. Remy Figure 17.2 Flower coll
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Figure 17.3 Narcissus flowers sprea
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398 C. Remy CONCLUSION The use of n
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400 C.G. Julian and P.W. Bowers Fig
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406 C.G. Julian and P.W. Bowers sym
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19 Review of pharmaceutical patents
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410 J.R. Murray to certain RNA viru
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412 J.R. Murray occurs in a two-pha
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414 J.R. Murray cognitive function
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416 J.R. Murray given at a time bet
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418 J.R. Murray Hofmannor, D., Mosc
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420 Index Backache, 403 Bacterial d
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422 Index Divisions (classification
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424 Index Leaf numbers, 11 Leaf sco
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426 Index Poet’s cultivars, 34 Po
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428 Index Subgenus (taxonomy); Ajax
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