Narcissus and Daffodil

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Galanthamine extraction 257 whether these differences in galanthamine content resulted from extracting plants at different stages of development or from using plants cultivated in different regions, or were simply due to the low purity of the isolated alkaloid. The screening described below was restricted to bulb tissue, because bulbs are the usual commodity traded and, unlike the aerial parts of the plants, are available in large quantities. The genus Narcissus was of particular interest, since it is indigenous to Europe and material can easily be obtained in quantity from large daffodil cultivars. Narcissus have been described as sources for natural galanthamine several times (Cherkasov, 1977; Cherkasov et al., 1984, 1986, 1988, 1989). Looking specifically for plants which would be available in large quantities, and therefore at a low price, the screening was restricted mainly to the 20 daffodil cultivars most commonly grown in the Netherlands (Erhardt, 1993). The plant material was obtained from cultivars grown around Hillegom and on Texel Island, the Netherlands. The identity of the plants was checked during the flowering period by studying their anatomical and microscopic characteristics. The daffodil cultivars used were identified according to ‘The International Daffodil Checklist’ of the Royal Horticultural Society (Kington, 1989), and, as far as possible, from reference plants and photographs. High-performance liquid chromatography (HPLC) (Kreh, 1995) and gas chromatography (Kreh, 1995; Kreh et al., 1995) were found to be suitable analytical methods for the analysis of alkaloids from Amaryllidaceae. For the quantitative galanthamine screening described below, the following HPLC method was used: Stationary phase: LiChrospher® 60 RP-select B, 5 µm, 250 × 4 mm column (Merck) Eluent A: 2.0 g sodium dodecylsulphate, 2000 ml water, 400 ml acetonitrile and 290 ml 0.05 M phosphoric acid Eluent B: acetonitrile Gradient: 0–25 min 25:75 A:B, 30–45 min linear to 100:0, flow 1ml/min For a detailed description of sample preparation, analytical equipment and quantitative evaluation, see Kreh (1995). The results of the HPLC screening are given in Table 9.1. From the plants tested, several narcissus cultivars were found to be rich in galanthamine. However, in the case of the Galanthus and Leucojum bulbs tested, only low concentrations of galanthamine were found. Differences between these values and those reported in the literature might result from the occurrence of different chemical races (Schulz, 1960) or from the effects of growing on different soils (see below and Gorinova et al., 1993). Such differences were also found in screening Narcissus ‘Fortune’ from Texel Island and from Hillegom, which have different soil types. Narcissus ‘Carlton’, ‘Gigantic Star’, ‘Ice Follies’ and ‘Fortune’ were found to be rich in alkaloids and galanthamine. All of these belong to the group of ‘largecupped’ daffodils (Division 2; Kington, 1989), which might be interesting for a further search for narcissus rich in galanthamine. For all the subsequent studies Narcissus ‘Carlton’ (Figure 9.1) was used, since it fulfils nearly all the requirements for galanthamine production on a large scale. It has been cultivated for many years in large amounts in the Netherlands and
258 M. Kreh Table 9.1 Results of galanthamine screening: percentage content of total alkaloids and galanthamine expressed on a fresh (FW) or dry (DW) weight basis Species or cultivar % Alkaloids % Galanthamine FW DW FW DW Chlidanthus fragrans 0.371 0.531 0.0017 0.0054 Crinum × powellii 0.200 0.231 0 0 Elisena longipetala 0.090 0.162 0 0 Galanthus elwesii 0.113 0.290 0.0084 0.0213 Galanthus nivalis 0.071 0.124 0.0013 0.0031 Ixolirion pallasii 0.003 0.007 0 0 Leucojum aestivum 0.033 0.236 0.0009 0.0065 Leucojum vernum 0.034 0.107 0.0001 0.0001 Narcissus ‘Barrett Browning’ 0.127 0.263 0.0047 0.0096 Narcissus ‘Brougshane’ 0.172 0.503 0.0004 0.0012 Narcissus ‘Carlton’ 0.216 0.555 0.0725 0.1880 Narcissus ‘Dick Wilden’ 0.099 0.230 0.0008 0.0019 Narcissus ‘Dutch Master’ 0.176 0.524 0.0001 0.0001 Narcissus ‘February Gold’ 0.105 0.660 0.0118 0.0780 Narcissus ‘Flower Drift’ 0.109 0.254 0.0163 0.0381 Narcissus ‘Flower Record’ 0.177 0.927 0.0150 0.0800 Narcissus ‘Fortune’ (from Hillegom) 0.140 0.310 0.0224 0.0488 Narcissus ‘Fortune’ (from Texel) 0.174 0.583 0.0208 0.0695 Narcissus ‘Gigantic Star’ 0.157 0.650 0.0290 0.1201 Narcissus ‘Golden Harvest’ 0.161 0.407 0 0 Narcissus ‘Ice Follies’ 0.090 0.264 0.0250 0.0740 Narcissus ‘Minnow’ 0.028 0.079 0.0006 0.0018 Narcissus ‘Salome’ 0.073 0.139 0.0020 0.0038 Narcissus ‘Tête-à-Tête’ 0.066 0.168 0 0 Narcissus ‘Unsurpassable’ 0.225 0.591 0.0004 0.0010 Narcissus ‘Van Sion’ 0.089 0.206 0.0037 0.0086 Narcissus ‘Verger’ 0.055 0.161 0 0 Narcissus ‘Yellow Sun’ 0.138 0.480 0.0035 0.0123 Nerine bowdenii 0.220 0.241 0 0 Sprekelia formosissima 0.011 0.021 0 0 Zephyranthes robusta 0.070 0.090 0.0033 0.0150 the UK with 354 ha in 1988/1989, it was the most cultivated narcissus in the Netherlands, and therefore easy to obtain and cheap (Erhardt, 1993). Narcissus ‘Carlton’ is not especially susceptible to diseases and climate, special winter protection is not necessary, and it has a high rate of multiplication (Jefferson-Brown, 1991). Since nearly all Amaryllidaceae alkaloids previously tested had interesting pharmacological and biological properties, it was the intention to isolate as many different alkaloids as possible from Narcissus ‘Carlton’. Using preparative HPLC, twenty-nine alkaloids were isolated from the bulbs, in addition to galanthamine. The structures of the then unknown natural products 1-O-acetyl-10-norpluviine, 10-norpluviine, O-methyloduline, N-demethylmasonine, 1,10-diacetyl-10-norpluviine and O-acetylgalanthamine were elucidated by modern spectroscopic techniques as well as by conventional analytical methods (Kreh, 1995).
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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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134 J.B. Briggs Table 5.3 Actual gr
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136 J.B. Briggs Table 5.4 Actual co
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138 J.B. Briggs Table 5.5 Capital c
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140 J.B. Briggs ADAS (1987a) Narcis
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142 J. Bastida and F. Viladomat Fig
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Table 6.1 Narcissus alkaloid struct
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Table 6.1b Continued Alkaloid name
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Table 6.1d Tazettine type O O R1 R2
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Table 6.1f Continued MeO Alkaloid n
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Table 6.2 Continued Species* Alkalo
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162 J. Bastida and F. Viladomat Tab
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Table 6.3 Continued Alkaloid* Formu
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Table 6.3 Continued Alkaloid* Formu
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176 J. Bastida and F. Viladomat Tab
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178 J. Bastida and F. Viladomat Cri
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180 J. Bastida and F. Viladomat It
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184 J. Bastida and F. Viladomat is
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186 J. Bastida and F. Viladomat and
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Table 6.4 Continued Alkaloid Activi
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196 J. Bastida and F. Viladomat tac
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198 J. Bastida and F. Viladomat Ang
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200 J. Bastida and F. Viladomat Boi
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202 J. Bastida and F. Viladomat lyc
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204 J. Bastida and F. Viladomat Fug
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Page 261 and 262: 240 C. Codina Hanks, G.R. and Jones
Page 263 and 264: 8 Narcissus and other Amaryllidacea
Page 265 and 266: 244 O.A. Cherkasov and O.N. Tolkach
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Page 281 and 282: 260 M. Kreh relation to the qualita
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Page 291 and 292: H O MeO O MeO H H HO H (1) (3) + 2
Page 293 and 294: 272 M. Kreh Gorinova, N.I., Atanass
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Page 305 and 306: 284 R.M. Moraes Kosley, R.W., Jr.,
Page 307 and 308: 11 Extraction and quantitative anal
Page 309 and 310: 288 N.P.D. Nanayakkara and J.K. Bas
Page 317 and 318: Table 11.1 GC and HPLC procedures f
Page 319 and 320: Table 11.1 Continued References Det
Page 325 and 326: 12 Synthesis of galanthamine and re
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308 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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