Narcissus and Daffodil

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Galanthamine extraction 271 only a few steps. Expensive purification procedures such as chromatography could be completely avoided, and the use of problematic reagents is very limited. This method has been tested with 96 kg of bulbs of Narcissus ‘Carlton’, leading to a further patent (Hille et al., 1996). Galanthamine can be obtained in even higher purity than the drug currently available on the market. ACKNOWLEDGEMENTS The author would like to acknowledge the help and support of Prof. Dr. R. Matusch, who served as mentor for this project. I would also like to thank F. van Elsäcker for his help in harvesting and extracting the plant material, and Lohmann Therapie- Systeme GmbH for financial support of the project. REFERENCES ABDA (1993) Central Database of the German Pharmacists Association, ABDATA-Pharma- Service, Frankfurt, Eschborn. Carroll, P., Furst, G.T., Han, S.Y. and Joullié, M. (1990) Spectroscopic studies on galanthamine and galanthamine methiiodide. Bulletin de la Société Chemique de France, 127, 769–780. Cherkasov, O.A. (1977) Plant sources of galanthamine. Khimiko-Farmatsevticheskii Zhurnal, 11 (6), 84–89 (in Russian). Cherkasov, O.A., Gorbunova, G.M., Margvelashvili, N.N., Maisuradze, N.I. and Tolkachev, O.N. (1986) The content of galanthamine in leaves of Narcissus hybridus hort. Rastitel’nye Resursy, 22 (3), 370–372 (in Russian). Cherkasov, O.A., Maisuradze, N.I., Glyzina, G.S. and Gayevskii, A.V. (1989) Narcissus as a source of raw materials for producing galanthamine. Khimiko-Farmatsevticheskii Zhurnal, 23 (5), 621–623 (in Russian). Cherkasov, O.A., Stikhin, V.A. and Savchuk, V.M. (1984) Content of galanthamine in some Amaryllidaceae species of the flora of the Ukrainian SSR. Rastitel’nye Resursy, 20 (4), 566– 568 (in Russian). Cherkasov, O.A., Tokhtabaeva, G.A., Margvelashvili, N.N., Maisuradze, N.I. and Tolkachev, O.N. (1988) The contents of galanthamine in some cultivars of Narcissus hybridus hort. Rastitel’nye Resursy, 24 (3), 414–420 (in Russian). Chimiko-Pharmazevtitschen Zavod (1959) A Method for Obtaining Galanthamine Hydrobromide. UK Patent No. GB 942 200; Bulgaria Patent Application No. BG 4404. Chimiko-Pharmazevtitschen Zavod (1963) A Method for Obtaining Galanthamine Hydrobromide. UK Patent No. GB 942 200. Cozanitis, D.A. and Rosenberg, P. (1983) Study of the analgesic effects of galanthamine, a cholinesterase inhibitor. Archives Internationales de Pharmacodynamie et de Thérapie, 266, 229–238. Czollner, L., Frantsits, W., Kenburg, B., Hedenig, U., Frohlich, J. and Jordis, U. (1998) New kilogram-synthesis of the Anti-Alzheimer drug (–)-galanthamine. Tetrahedron Letters, 39, 2087–2088. Erhardt, W. (1993) Narzissen. Eugen Ulmer Verlag, Stuttgart. Fitzgerald, D.B., Hartwell, J.L. and Leitner, J. (1958) Tumor-damaging activity in plant families showing antimalarial activity. Journal of the National Cancer Institute, 20, 763–774. Fuganti, C. (1975) The amaryllidaceae alkaloids. In: R.H.F. Manske (ed.), The Alkaloids, Vol. 15, Academic Press, New York.
272 M. Kreh Gorinova, N.I., Atanassov, A.I., Stojanov, D.V. and Tencheva, J. (1993) Influence of chemical composition of soils on the galanthamine content in Leucojum aestivum. Journal of Plant Nutrition, 16 (9), 1631–1636. Han, S.Y., Mayer, S.C., Schweiger, E.J., Davis, B.M. and Joullié, M.M. (1991) Synthesis and biological activity of galanthamine derivatives as acetylcholinesterase inhibitors. Bioorganic and Medicinal Chemistry Letters, 1 (11), 579–580. Hille, T., Hoffmann, H.R., Kreh, M. and Matusch, R. (1996) Verfahren zur Isolierung von Galanthamin. Germany Patent No. DE 195 09 663 A1. Jefferson-Brown, M. (1991) Narcissus. B.T. Batsford Ltd, London. Kington, S. (1989) The International Daffodil Checklist. The Royal Horticultural Society, London. Kreh, M. (1995) Galanthamin und andere Amaryllidaceen Alkaloide. Dissertation, Marburg University. Kreh, M., Matusch, R. and Witte, L. (1995) Capillary gas chromatography-mass spectrometry of Amaryllidaceae alkaloids. Phytochemistry, 38 (3), 773–776. Kreh, M., Müller, U. and Matusch, R. (1994) Bildung, Kristallstruktur und absolute Konfiguration von (–)-N-(Chloromethyl)galanthaminium-chlorid. Helvetica Chimica Acta, 77, 1611–1615. Opitz, K., Lohmann Therapie-Systeme and Hefa-Frenon Arzneimittel (1991) Pharmazeutische Formulierung zur Behandlung des Alkoholismus. Germany Patent No. DE 40 10 079 A1. Paskov, D.S., Dobrev, H. and Nikiforov, N. (1963) Drugs and respiration. In: Proceedings of the 2nd International Pharmacological Meeting, August 1963, Pergamon Press, New York, pp. 113–114. Paskov, D. and Ivanova, Z.C. (1967) Galanthamine Hydrobromide. France Patent No. FR 1 481 003, 670519; Bulgaria Patent No. BG 590 302. Proskurnina, N.F. and Yakovleva, A.P. (1947) Alkaloids from Galanthus woronowii. Zhurnal Obshchei Khimii, 17, 1216–1216 (in Russian). Proskurnina-Shapiro, N.F. and Yakovleva, A.P. (1966a) Isolation of Galanthamine. USSR Patent No. SU 145 583, 661 117, 610 503. Proskurnina-Shapiro, N.F. and Yakovleva, A.P. (1966b) Verfahren zur Gewinnung von Galanthaminhydrobromid aus Pflanzen der Familie der Amaryllidaceen. Germany Patent No. DE 1 193 061. Schulz, B. (1960) Galanthus-Alkaloide, neue Parasympathomimetika. Deutsche Apotheker- Zeitung, 100 (8), 43–43. Schwyzer, J. (1931) Die Fabrikation Pharmazeutischer und Chemisch-technischer Produkte. Julius Springer Verlag, Berlin. Tanahashi, T., Poulev, A. and Zenk, M.H. (1990) Radioimmunoassay for the quantitative determination of galanthamine. Planta Medica, 56, 77–81.
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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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206 J. Bastida and F. Viladomat Han
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208 J. Bastida and F. Viladomat Kin
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210 J. Bastida and F. Viladomat of
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212 J. Bastida and F. Viladomat Sp
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214 J. Bastida and F. Viladomat Wil
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216 C. Codina and, consequently, hi
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218 C. Codina easily lost on transf
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Page 259 and 260: 238 C. Codina mg/g DW mg/g DW 1.5 1
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
Page 277 and 278: 9 Studies on galanthamine extractio
Page 279 and 280: 258 M. Kreh Table 9.1 Results of ga
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Page 291: H O MeO O MeO H H HO H (1) (3) + 2
Page 295 and 296: 274 R.M. Moraes (Katz and Taneck, 1
Page 297 and 298: 276 R.M. Moraes bulbs of many Narci
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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
Page 327 and 328: 306 V.N. Bulavka and O.N. Tolkachev
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322 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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