Narcissus and Daffodil

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Synthesis of galanthamine 331 Vlahov, R., Krikorian, D., Spasov, G., Chinova, M., Parushev, S., Zagorova, M., Tarpanov, V., Vlahov, J., Snatzke, G., Duddeck, H., Schaefer, H.J. and Kieslich, K. (1984) New approaches to the total synthesis of galanthamine. In: Cz. Szantay, A. Gottsegen and G. Kovacz (eds.), 2nd International Conference on Chemistry and Biotechnology of Biologically Active Natural Products, Budapest, August 1983, pp. 251–272 (Studies in Organic Chemistry, Vol. 17, Elsevier Science Publishers). Vlahov, R., Krikorian, D., Spasov, G., Chinova, M., Vlahov, I., Parushev, S., Snatzke, G., Ernst, L., Kieslich, K., Abraham, W.-R. and Shelldrick, W.S. (1989) Synthesis of galanthamine and related alkaloids – new approaches. I. Tetrahedron, 45 (11), 3329–3346. Vlahov, R., Krikorian, D., Zagorova, M., Chinova, M., Parushev, S., Snatzke, G. and Schaefer, H.J. (1978) New approaches to the total synthesis of narwedine-type enones (precursors of Amaryllidaceae alkaloids). In: N.Marekov, I. Ognyanov and A. Orahovats (eds.), 11th IUPAC International Symposium on the Chemistry of Natural Products, BAN, Sofia, Symposium Papers, Vol. 4, Part 2, pp. 251–273. Vlahov, R.J., Krikorian, D.A., Zagorova, M.S., Chinova, M.Kh. and Parushev, S.P. (1980a) Method of Production of Narwedine Type Dienones and their Derivatives. Bulgarian Patent No. 28,324 (Bulletin Izobreteniya, Torgovski Marky, Promishleni Obrazci, Sofia, 1980, No. 4, p. 13) (in Bulgarian). Vlahov, R.J., Krikorian, D.A., Zagorova, M.S., Chinova, M.Kh. and Parushev, S.P. (1980b) Method of Production of Narwedine Type Enones and their Derivatives. Bulgarian Patent No. 28,325 (Bulletin Izobreteniya, Torgovski Marky, Promishleni Obrazci, Sofia, 1980, No. 4, pp. 13–14) (in Bulgarian).
13 Compounds from the genus Narcissus: pharmacology, pharmacokinetics and toxicology David Brown INTRODUCTION The genus Narcissus has yielded several useful or potentially useful compounds, although just one of them, galanthamine, has been investigated in any great detail. As with most modern phytopharmaceuticals, identification, purification and investigation of the active principles have only been accomplished after many years, perhaps centuries, of folk medicine use as whole plant material or crude extracts. For the earliest account of a clinical use of galanthamine one has to go back to ancient Greek times. Homer’s Odyssey has it that the attempts of Circe to poison Odysseus were foiled when Hermes gave Odysseus an antidotal root drawn from the earth, with a black root and milk-like flower, which was difficult for mortals to dig up and which the gods called ‘moly’. On the basis of descriptions of their symptoms (memory loss, hallucinations and delusions that they had been turned into pigs) it has been suggested that the drug which Circe had used to poison Odysseus’ men was a powerful, centrally acting, anticholinergic drug called stramonium, derived from the common plant Datura stramonium. The story is told much more eloquently by Plaitakis and Duvoisin (1983) who postulate that the antidote was derived from the common snowdrop, Galanthus nivalis, which contains the anticholinesterase, galanthamine. This is based on the description of the antidote or ‘moly’ given by Homer and by later Greek texts and recognition that both plants (Datura and Galanthus) would have been a resource native to the area. The authors state that if all this were true, then it represents the oldest recorded use of an anticholinesterase to reverse anticholinergic intoxication. Of course, these accounts refer to snowdrop, not narcissus, but galanthamine is a derivative common to both. Originally isolated from Galanthus nivalis and used clinically under the name ‘Nivalin’, galanthamine can also be derived from Narcissus cultivars (Moraes-Cerdeira et al., 1997) and represents the most pharmacologically interesting and to date, clinically useful compound, to be derived from the genus. There is at the time of writing, considerable interest in galanthamine as a potential treatment for Alzheimer’s disease. This chapter reviews the pharmacology, pharmacokinetics and toxicology of galanthamine in animals and man. The rationale behind its various putative clinical uses is also discussed. Reference is also made to another interesting compound, pretazettine, which has been investigated as an adjunct to cancer chemotherapy. Clinical (phase 2 and 3) trials with galanthamine in Alzheimer’s disease are discussed in the following chapter of this volume.
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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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220 C. Codina they might be more su
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222 C. Codina µ g/g FW µ g/g FW 3
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224 C. Codina Kinetin As observed i
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226 C. Codina Table 7.3 Total produ
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228 C. Codina Accumulation of alkal
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230 C. Codina Accumulation of alkal
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232 C. Codina Effect on growth and
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234 C. Codina mg/g DW mg/g DW 0.90
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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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Page 307 and 308: 11 Extraction and quantitative anal
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Page 357 and 358: 336 D. Brown Absorption Galanthamin
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Page 377 and 378: 356 D. Brown examination of a brain
Page 379 and 380: 358 D. Brown A successful cholinerg
Page 381 and 382: Table 14.2 Summary of human trials
Page 383 and 384: 362 D. Brown statistically signific
Page 385 and 386: 364 D. Brown ( Jann, 1998); see Tab
Page 387 and 388: 366 D. Brown REFERENCES Bartus, B.T
Page 389 and 390: 368 D. Brown Wilcock, G.K., Scott,
Page 391 and 392: 370 K. Ingkaninan, H. Irth and R. V
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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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