Narcissus and Daffodil

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Pharmacology of Narcissus compounds 349 inhibit protein synthesis and prevent the growth of cancer cells and viruses (see Figure 13.1). During antiviral screening of medicinal plants from the Pacific area, Furasawa and co-workers found that the alkaloid pretazettine was active against Rauscher viral leukaemia and spontaneous T-cell leukaemia in mice (Furusawa et al., 1976b, 1979). Pretazettine was inhibitory towards murine retroviruses in cell cultures and in vivo. The compound was shown to inhibit viral reverse transcriptase (Furasawa et al., 1978), and was cytotoxic due to a specific inhibitory action on cellular protein rather than nucleic acid synthesis and therefore active against non-viral transplantable tumours. Later studies established that pretazettine was active against Ehrlich ascites carcinoma – a non-viral, transplantable tumour – in mice (Furusawa et al., 1981) and that the compound enhanced the antitumour activity of a standard combination of adriamycin, 1,3-bis-(2-chloroethyl)-1-nitrosourea (BCNU) and cyclophosphamide – the so-called ABC regimen – when used as an adjuvant to the latter. Significant survival rates were seen in inoculated animals. The authors also demonstrated that pretazettine could inhibit protein synthesis, but not nucleic acid synthesis in human carcinoma cells in vitro. A further interesting finding was that adriamycin pre-treated, human carcinoma cells were more sensitive to pretazettine; therefore the drug could be used at lower doses which were not inhibitory when pretazettine was used on its own. This suggested to the authors that the compound might be useful as adjuvant therapy, eradicating residual tumour cells by preventing the synthesis of proteins, notably DNA polymerase beta, necessary for DNA repair. In addition to the above, preliminary experiments suggested that pretazettine was effective against intraperitoneally inoculated Lewis-lung carcinoma – another non-viral, transplantable tumour – in mice (Furusawa and Furusawa, 1983). Pretazettine was also studied when the inoculation was subcutaneous in singeneic mice, more resistant to chemotherapy (Furusawa and Furusawa, 1986). In the latter model, pretazettine was inhibitory to pulmonary metastases but not growth of the primary tumour or in prolonging life span. The compound was more effective against the primary tumour when combined with standard cytotoxic agents such as adriamycin, cisplatin, 5-fluorouracil, methotrexate and vincristine; these were not effective when administered individually. This indicates that pretazettine may be useful as an adjuvant to induce positive effects from otherwise inactive agents. In allogenic mice, pretazettine inhibited metastases and also prolonged life span. The same group has also investigated the activity of pretazettine against spontaneous T-cell leukaemia in mice compared with that of some established antileukaemic agents. The activity of pretazettine was shown to be superior to methotrexate, 6-thioguanine and adriamycin, but inferior to vincristine. Combination with vincristine, 6-thioguanine and adriamycin was synergistic whereas, combination with methotrexate was not. Pretazettine was also shown to reverse the leukaemia enhancing effect of cyclosporine in this animal model at the preleukaemic stage, although the mechanism was unclear (Furusawa and Furusawa, 1988). The implications of this work for the treatment of similar cancers in man await confirmation by independent study. Pretazettine has been shown to be active against selected RNA-containing flaviviruses (Japanese encephalitis, yellow fever and dengue) and bunyaviruses
350 D. Brown (Punto Toro and Rift Valley fever) in organ culture. Activity in an animal model was not studied (Gabrielsen et al., 1992). This activity may reflect a general ability to inhibit protein synthesis during viral replication. REFERENCES Agarawal, H.C. and Gupta, S.E. (1990) Ocular hypotensive effect of galanthamine hydrobromide: an experimental study. Indian Journal of Pharmacology, 22, 117–118. Bachus, R. (1995) Metabolites of Galanthamine: Origin and Action. Inaugural Dissertation, Faculty of Medicine, Free University of Berlin, Berlin. Baraka, A. and Cozanitis, D. (1973) Galanthamine vs neostigmine for reversal of nondepolarising neuromuscular block in man. Anesthesia and Analgesia, 53, 832–835. Baraka, A. and Harik, S. (1977) Reversal of central anticholinergic syndrome by galanthamine. Journal of the American Medical Association, 238(21), 2293–2294. Barton, D.H.R. and Kirby, G.W. (1960) The synthesis of galanthamine. Proceedings of the Chemical Society, 392–393. Becker, R.E., Morierty, P.L. and Unni, L. (1991) The second generation of cholinesterase inhibitors: clinical and pharmacological effects. In: R. Becker and E. Giacobini (eds.), Cholinergic Basis for Alzheimer Therapy, Birkhauser, Boston, pp. 263–296. Bickel, U., Thomsen, T., Fischer, J.P., Weber, W. and Kewitz, H. (1991a) Galanthamine: pharmacokinetics, tissue distribution and cholinesterase inhibition in brain of mice. Neuropharmacology, 30 (5), 447–454. Bickel, U., Thomsen, T., Weber, W., Fischer, J.P., Bachus, R., Nitz, M. and Kewitz, H. (1991b) Pharmacokinetics of galanthamine in humans and corresponding cholinesterase inhibition. Clinical Pharmacology and Therapeutics, 50 (4), 420–428. Boissier, J.R., Combes, G. and Pagny, J. (1960) La galanthamine, puissant cholinergique naturel. Annals de Pharmacologie, 48, 888–900. Boissier, J.R. and Lesbros, J. (1962) La galanthamine, puissant cholinergic naturel. II – activité anticholinesterasique de la galanthamine et quelques derivés. Annals de Pharmacologie, 52,150–155. Bores, G.M., Huger, F.P., Petko, W., Mutlib, A.E., Camacho, F., Rush, D.K., Selk, D.E., Wolf, V., Kosley, R.W., Davis, L. and Vargas, H.M. (1996) Pharmacological evaluation of novel Alzheimer’s disease therapeutics: acetylcholinesterase inhibitors related to galanthamine. Journal of Pharmacology and Experimental Therapeutics, 277 (2), 728–738. Bores, G.M. and Kosley, R.W. (1996) Galanthamine derivatives for the treatment of Alzheimer’s disease. Drugs of the Future, 21 (6), 621–635. Chaplygina, S.R. and Ilyutchenok, R.Y. (1976) The action of cholinergic drugs in experimental amnesia. Zhurnal Vysshei Nervnoi Deiatelnosti, 26, 1091–1093. Chopin, P. and Brierly, M. (1992) Effects of four noncholinergic cognitive enhancers in comparison with tacrine and galanthamine on scopolamine-induced amnesia in rats. Psychopharmacology, 106, 26–30. Chrusciel, M. and Varagic, V. (1966) The effect of galanthamine on the blood pressure of the rat. British Journal of Pharmacology, 26, 295–310. Cozanitis, D.A. (1971) Experiences with galanthamine hydrobromide as a curare antagonist. Der Anaesthesist, 20, 226–229. Cozanitis, D.A. (1974) Galanthamine hydrobromide vs neostigmine. A plasma cortisol study. Anesthesia, 29 (2), 163–168. Cozanitis, D.A. (1977) Galanthamine hydrobromide, a longer acting anticholinesterase drug, in the treatment of the central effects of scopolamine (hyoscine). Der Anaesthesist, 26, 649–650.
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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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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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Page 325 and 326: 12 Synthesis of galanthamine and re
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Page 367 and 368: 346 D. Brown Galanthamine causes br
Page 369: 348 D. Brown (1994) go on to mentio
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Page 375 and 376: 354 D. Brown Snorrason, E. and Stef
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
Page 401 and 402: 16 Narcissus lectins Els J.M. Van D
Page 403 and 404: 382 E.J.M. Van Damme and W.J. Peuma
Page 413 and 414: 17 Narcissus in perfumery HISTORY C
Page 415 and 416: 394 C. Remy Figure 17.2 Flower coll
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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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