Alkaloids of <strong>Narcissus</strong> 207 Ikram, M. (1983) Screening of medicinal plants of Pakistan for anticancer activity. Fitoterapia, 54, 123–126. Immirzi, A. <strong>and</strong> Fuganti, C. (1971) Crystal structure of narcissidine methiodide. Journal of the Chemical Society (B), 1218–1220. Irie, H., Tsuda, Y. <strong>and</strong> Uyeo, S. (1959) The structure of tazettine. A synthesis of the Emde degradation product derived from tazettamide. Journal of the Chemical Society, 1446–1459. Ishizaki, M., Kai, Y., Makanae, Y. <strong>and</strong> Hoshino, O. (1998) Asynthetic approach toward optically active lycorine: Synthesis of optically active 2-methyllycoranes by radical reaction. ACH Models in Chemistry, 135, 529–552. Jaspersen-Schib, R., Theus, L., Guirguis-Oeschger, M., Gossweiler, B. <strong>and</strong> Meier-Abt, P.J. (1996) Wichtige pflanzenvergiftungen in der Schweiz 1966–1994. Schweizerische Medizinische Wochenschrift, 126, 1085–1098. Jefferson-Brown, M. (1991) <strong>Narcissus</strong>. B.T. Batsford Ltd., London. Jeffs, P.W. (1981) Sceletium alkaloids. In: R.H.F. Manske <strong>and</strong> R.G.A. Rodrigo (eds.), The Alkaloids, vol. 19, Academic Press, New York, pp. 1–80. Jeffs, P.W., Capps, T., Johnson, D.B., Karle, J.M., Martin, N.H. <strong>and</strong> Rauckman, B. (1974) Sceletium alkaloids. VI. Minor alkaloids of S. namaquense <strong>and</strong> S. strictum. Journal of Organic Chemistry, 39, 2703–2710. Jeffs, P.W., Abou-Donia, A., Campau, D. <strong>and</strong> Staiger, D. (1985) Structures of 9-O-demethylhomolycorine <strong>and</strong> 5α-hydroxyhomolycorine. Alkaloids of Crinum defixum, C. scabrum, <strong>and</strong> C. latifolium. Assignment of aromatic substitution patterns from 1 H-coupled 13 C spectra. Journal of Organic Chemistry, 50, 1732–1737. Jeffs, P.W., Mueller, L., Abou-Donia, A.H., Seif el-Din, A.A. <strong>and</strong> Campau, D. (1988) Nobilisine, a new Alkaloid from Clivia nobilis. Journal of Natural Products, 51, 549–554. Jiménez, A., Sánchez, L. <strong>and</strong> Vázquez, D. (1975a) Location of resistance to the alkaloid narciclasine in the 60S ribosomal subunit. FEBS Letters, 55, 53–56. Jiménez, A., Sánchez, L. <strong>and</strong> Vázquez, D. (1975b) Yeast ribosomal sensitivity <strong>and</strong> resistance to the Amaryllidaceae alkaloids. FEBS Letters, 60, 66–70. Jiménez, A., Santos, A., Alonso, G. <strong>and</strong> Vázquez, D. (1976) Inhibitors of protein synthesis in eukaryotic cells. Comparative effects of some Amaryllidaceae alkaloids. Biochimica et Biophysica Acta, 425, 342–348. Junko, I., Akito, T., Yumiko, K. <strong>and</strong> Noriyoshi, O. (1994) Poisoning by Lycoris radiata plants. Pharmaceuticals Monthly, 36, 855–857. Kametani, T., Yamaki, K., Yagi, H. <strong>and</strong> Fukumoto, K. (1969) Studies on the synthesis of heterocyclic compounds. Part CCCXV. Modified total synthesis of (±)-galanthamine through phenol oxidation. Journal of the Chemical Society (C), 2602–2605. Keck, G.E. <strong>and</strong> Fleming, S.A. (1978) Model studies on <strong>Narcissus</strong> alkaloids. Synthetic methodology for the synthesis of lycoricidine analogues. Tetrahedron Letters, 4763–4766. Keiser, I., Harris, E.J., Miyashita, D.H., Jacobson, M. <strong>and</strong> Perdue, R.E. (1975) Attraction of ethyl ether extracts of 232 botanicals to oriental fruit flies, melon flies, <strong>and</strong> mediterranean fruit flies. Lloydia, 38, 141–152. Kewitz, H. (1996) Galanthamine. A viewpoint. Drugs <strong>and</strong> Aging, 9, 66–67. Kewitz, H. (1997) Pharmacokinetics <strong>and</strong> metabolism of galanthamine. Drugs of Today, 33, 265–272. Kihara, M., Koike, T., Imakura, Y., Kida, K., Shingu, T. <strong>and</strong> Kobayashi, S. (1987) Alkaloidal constituents of Hymenocallis rotata Herb. (Amaryllidaceae). Chemical <strong>and</strong> Pharmaceutical Bulletin, 35, 1070–1075. Kihara, M., Xu, L., Konishi, K., Nagao, Y., Kobayashi, S. <strong>and</strong> Shingu, T. (1992) Incartine, a biosynthetic intermediate, from the flowers of Lycoris incarnata. Heterocycles, 34, 1299– 1301. Kihara, M., Ozaki, T., Kobayashi, S. <strong>and</strong> Shingu, T. (1995) Alkaloidal constituents of Leucojum autumnale L. (Amaryllidaceae). Chemical <strong>and</strong> Pharmaceutical Bulletin, 43, 318–320.
208 J. Bastida <strong>and</strong> F. Viladomat Kington, S. (1989) The International <strong>Daffodil</strong> Checklist. Royal Horticultural Society, London. Kinstle, T.H., Wildman, W.C. <strong>and</strong> Brown, C.L. (1966) Mass spectra of Amaryllidaceae alkaloids. The structure of narcissidine. Tetrahedron Letters, 4659–4666. Kirby, G.W. <strong>and</strong> Michael, J. (1973) Stereoselective β-labeling of aromatic amino-acids with deuterium <strong>and</strong> tritium. Journal of the Chemical Society Perkin Transactions I, 115–120. Kirby, G.W. <strong>and</strong> Tiwari, H.P. (1966) Phenol oxidation <strong>and</strong> biosynthesis. Part IX. The biosynthesis of norpluviine <strong>and</strong> galanthine. Journal of the Chemical Society (C), 676–682. Kita, Y., Arisawa, M., Gyoten, M., Nakajima, M., Hamada, R., Tohma, H. <strong>and</strong> Takada, T. (1998) Oxidative intramolecular phenolic coupling reaction induced by a hypervalent iodine (III) reagent: Leading to galanthamine-type Amaryllidaceae alkaloids. Journal of Organic Chemistry, 63, 6625–6633. Kitagawa, T., Taylor, W.I., Uyeo, S. <strong>and</strong> Yajima, H. (1955) The constitution of homolycorine <strong>and</strong> lycorenine. Journal of the Chemical Society, 1066–1068. Kobayashi, S., Ishikawa, H., Kihara, M., Shingu, T. <strong>and</strong> Hashimoto, T. (1977) Isolation of carinatine <strong>and</strong> pretazettine from the bulbs of Zephyranthes carinate Herb. (Amaryllidaceae). Chemical <strong>and</strong> Pharmaceutical Bulletin, 25, 2244–2248. Kobayashi, S., Kihara, M., Shingu, T. <strong>and</strong> Shingu, K. (1980) Transformation of tazettine to pretazettine. Chemical <strong>and</strong> Pharmaceutical Bulletin, 28, 2924–2932. Kobayashi, S., Satoh, K., Numata, A., Shingu, T. <strong>and</strong> Kihara, M. (1991) Alkaloid N-oxides from Lycoris sanguinea. Phytochemistry, 30, 675–677. Kreh, M. <strong>and</strong> Matusch, R. (1995) O-methyloduline <strong>and</strong> N-demethylmasonine, alkaloids from <strong>Narcissus</strong> pseudonarcissus. Phytochemistry, 38, 1533–1535. Kreh, M., Matusch, R. <strong>and</strong> Witte, L. (1995a) Capillary gas chromatography-mass spectrometry of Amaryllidaceae alkaloids. Phytochemistry, 38, 773–776. Kreh, M., Matusch, R. <strong>and</strong> Witte, L. (1995b) Acetylated alkaloids from <strong>Narcissus</strong> pseudonarcissus. Phytochemistry, 40, 1303–1306. Kuriyama, K., Iwata, T., Moriyama, M., Kotera, K., Hamada, Y., Mitsui, R. <strong>and</strong> Takeda, K. (1967) The optical rotatory behaviour of lycorine <strong>and</strong> related compounds. Journal of the Chemical Society (B), 46–53. Kushida, N., Atsumi, S., Koyano, T. <strong>and</strong> Umezawa, K. (1997) Induction of flat morphology in K-ras-transformed fibroblasts by lycorine, an alkaloid isolated from the tropical plant Eucharis gr<strong>and</strong>iflora. Drugs under Experimental <strong>and</strong> Clinical Research, 23, 151–155. Labraña, J., Choy, G., Solans, X., Font-Bardia, M., de la Fuente, G., Viladomat, F., Codina, C. <strong>and</strong> Bastida, J. (1999) Alkaloids from <strong>Narcissus</strong> bujei (Amaryllidaceae). Phytochemistry, 50, 183–188. Laiho, S.M. <strong>and</strong> Fales, H.M. (1964) Narcissamine. A Quasi-racemic alkaloid. Journal of the American Chemical Society, 86, 4434–4438. Laing, M. <strong>and</strong> Clark, R.C. (1974) The crystal <strong>and</strong> molecular structure of the O,O′-dipara-bromobenzoate of brunsvigine, an Amaryllidaceae alkaloid from Brunsvigia cooperii. Tetrahedron Letters, 583–584. Latvala, A., Önür, M.A., Gözler, T., Linden, A., Kivçak, B. <strong>and</strong> Hesse, M. (1995a) Alkaloids of Galanthus elwesii. Phytochemistry, 39, 1229–1240. Latvala, A., Önür, M.A., Gözler, T., Linden, A., Kivçak, B. <strong>and</strong> Hesse, M. (1995b) Nitrogen inversion in 9-O-demethylhomolycorine. Tetrahedron Asymmetry, 6, 361–364. Lewis, J.R. (1998) Amaryllidaceae <strong>and</strong> Sceletium Alkaloids. Natural Product Reports, 15, 107–110. Li, H.Y., Ma, G.E., Xu, Y. <strong>and</strong> Hong, S.H. (1987) Alkaloids of Lycoris guangxiensis. Planta Medica, 53, 259–261. Likhitwitayawuid, K., Angerhofer, C.K., Chai, H., Pezzuto, J.M., Cordell, G.A. <strong>and</strong> Ruangrungsi, N. (1993) Cytotoxic <strong>and</strong> antimalarial alkaloids from the bulbs of Crinum amabile. Journal of Natural Products, 56, 1331–1338. Lin, L.Z., Hu, S.F., Chai, H.B., Pengsuparp, T., Pezzuto, J.M., Cordell, G.A. <strong>and</strong> Ruangrungsi, N. (1995) Lycorine alkaloids from Hymenocallis littoralis. Phytochemistry, 40, 1295–1298.
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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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Table 6.2 Continued Species* Alkalo
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- Page 277 and 278: 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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290 N.P.D. Nanayakkara and J.K. Bas
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292 N.P.D. Nanayakkara and J.K. Bas
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294 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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300 N.P.D. Nanayakkara and J.K. Bas
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302 N.P.D. Nanayakkara and J.K. Bas
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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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308 V.N. Bulavka and O.N. Tolkachev
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310 V.N. Bulavka and O.N. Tolkachev
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312 V.N. Bulavka and O.N. Tolkachev
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314 V.N. Bulavka and O.N. Tolkachev
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316 V.N. Bulavka and O.N. Tolkachev
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318 V.N. Bulavka and O.N. Tolkachev
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320 V.N. Bulavka and O.N. Tolkachev
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322 V.N. Bulavka and O.N. Tolkachev
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324 V.N. Bulavka and O.N. Tolkachev
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326 V.N. Bulavka and O.N. Tolkachev
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328 V.N. Bulavka and O.N. Tolkachev
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330 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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372 K. Ingkaninan, H. Irth and R. V
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374 K. Ingkaninan, H. Irth and R. V
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376 K. Ingkaninan, H. Irth and R. V
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378 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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384 E.J.M. Van Damme and W.J. Peuma
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386 E.J.M. Van Damme and W.J. Peuma
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388 E.J.M. Van Damme and W.J. Peuma
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390 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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402 C.G. Julian and P.W. Bowers Fig
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404 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