Narcissus and Daffodil

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Analysis of Amaryllidaceae alkaloids 299 and CGC have emerged as the most accurate and practical analytical procedures to determine these compounds in natural sources and in biological samples. HPLC was the most widely used technique for this purpose, especially when only one constituent was quantified. Due to the presence of at least one aromatic ring in their chemical structures, Amaryllidaceae alkaloids can be conveniently quantified with high sensitivity by a UV or a fluorescence detector. This method is not always suitable for the routine analysis of Amaryllidaceae alkaloids in natural sources. Usually, alkaloid fractions of Amaryllidaceae contain complex mixtures of compounds with diverse chemical structures and polarities. It is often difficult to achieve good resolution of these mixtures with reasonable peak shapes, even with complex solvent programming. The resolution and peak shapes for a mixture of standards also appear to vary widely under identical experimental conditions for commercially available reversed-phase columns with similar specifications from different suppliers. CGC appears to be a better technique for the simultaneous quantification of several different alkaloids in natural sources. Amaryllidaceae alkaloids can be analysed by this method without any prior derivatisation. However, the method is not applicable to quaternary alkaloids and alkaloid N-oxides. Compounds usually show very sharp peaks and can be detected using a flame ionisation detector (FID), a nitrogen phosphorus detector (NPD) or mass spectrometry (MS). A very high resolution, even for complex mixtures of alkaloids, can be achieved with relatively short capillary columns within a reasonable experimental time. Two of the most common Amaryllidaceae alkaloids, haemanthamine and lycorine, were reported to undergo partial decomposition under GC experimental conditions. These compounds still appear as relatively sharp single peaks, with good concentration/response linearity in a wide range of concentrations, and can be quantified reproducibly. These analyses can be performed with little sample preparation, and are suitable for routine quantitative analysis of Amaryllidaceae alkaloids in natural sources. Useful information on these two analytical procedures is summarised in Table 11.1. ACKNOWLEDGEMENTS We express our gratitude to Dr. Larry Walker for his many suggestions and for reviewing the manuscript. REFERENCES Amico, A., Stefanizzi, L., Bruno, S. and Bonvino, V. (1980) Distribution of lycorine in Sternbergia lutea Ker-Gawl. Quarterly Journal of Crude Drug Research, 18, 27–31. Asoeva, E.Z. and Vergeichik, E.N. (1967) Separation and quantitative determination of alkaloids in Galanthus krasnovii. Nauchnye Doklady Vysshei Shkoly, Biologicheskie Nauki, 7, 98–101 (in Russian) (Chemical Abstracts, 67, 94035). Bagdasarova, I.Ya. (1984) Differential spectrophotometric analysis of galanthamine hydrobromide in drug forms. Farmatsevtichnii Zhurnal (Kiev), 4, 68–69 (in Ukrainian) (Chemical Abstracts, 101, 198267).
300 N.P.D. Nanayakkara and J.K. Bastos Bastos, J.K., Li, X., Nanayakkara, N.P.D., Burandt, C.L., Jr., Moraes-Cerdeira, R.M. and McChesney, J.D. (1996) A rapid quantitative method for the analysis of galanthamine and other Amaryllidaceae alkaloids by capillary column gas chromatography. Journal of Natural Products, 59, 638–640. 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, 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 (St. Louis), 50, 420–428. Bores, G.M., Huger, F.P., Petko, W., Mutlib, A.E., Camacho, F., Rush, D.K., Selk, D.E., Wolf, V., Kosley, R.W., Jr., 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, 728–738. Bruno, S. and De Laurentis, N. (1982) Spectrofluorimetric study of some alkaloids of the Amaryllidaceae family. Bollettino Chimico Farmaceutico, 121, 402–407 (in Italian) (Chemical Abstracts, 98, 104278). Bruno, S., De Laurentis, N., Amico, A. and Stefanizzi, L. (1985) Localization and simultaneous determination of lycorine and tazettine in bulbs of Narcissus tazetta by HPLC. Plantes médicinales et phytothérapie, 19, 211–215. Burgudjiev, Z.T. and Grinberg, M.H. (1993) Spectral study of the alkaloid galanthamine. I. Ultraviolet absorption spectra and fluorescence spectra. Godishnik na Sofiiskiya Universitet “Sv. Kliment Okhridski” Fizicheski Fakultet, 81, 121–133 (in Bulgarian) (Chemical Abstracts, 121, 301116). Claessens, H.A., Lemmens, A.A.G., Sparidans, R.W. and Everaerts, F.M. (1988) Pretreatment of body fluids by preparative isotachophoresis prior to chromatographic analysis. Chromatographia, 26, 351–358. Claessens, H.A., Van Thiel, M., Westra, P. and Soeterboek, A.M. (1983) High-performance liquid chromatographic determination of galanthamine, a long-acting anticholinesterase drug, in serum, urine, and bile. Journal of Chromatography, 275, 345–353. Davey, M.W., Persiau, G., De Bruyn, A., Van Damme, J., Bauw, G. and Van Montagu, M. (1998) Purification of the alkaloid lycorine and simultaneous analysis of ascorbic acid and lycorine by micellar electrokinetic capillary chromatography. Analytical Biochemistry, 257, 80–88. Dobronravova, E.K., Sattarova, A.Kh. and Shakirov, T.T. (1982) Chromatographic behavior of halide salts of alkaloids on alumina. Khimiya Prirodnykh Soedinenii, 1, 127 (in Russian) (Chemical Abstracts, 96, 223354). Eckers, C., Games, D.E., Lewis, E., Rao, K.R.N., Rossiter, M. and Weerasinghe, N.C.A. (1980) Studies of natural products and pesticides and their metabolites by LCMS and other mass spectral methods. Advances in Mass Spectrometry, 8B, 1396–1404. El-Din, A.S., Korany, M., Abou-Donia, A. and Sabry, N.N. (1983) Spectrophotometric and fluorimetric determination of lycorine in Amaryllidaceae species. Acta Pharmaceutica Jugoslavica, 33, 143–147 (Chemical Abstracts, 99, 117286) . Evidente, A., Iasiello, I. and Randazzo, G. (1983) Rapid quantitative analysis of lycorine by reversed-phase high-performance liquid chromatography. Journal of Chromatography, 281, 362–366. Ghous, T. and Townshend, A. (1998) Flow injection determination of neostigmine and galanthamine by immobilised acetylcholinesterase inhibition. Analytica Chimica Acta, 372, 279–286. Gheorghiu, A., Constantinescu, A. and Ionescu-Matiu, E. (1962) Electrophoretic study of some active principals of Leucojum vernum and L. aestivum. Revista Medicala (Targu-Mures, Romania), 8, 54–56 (in Romanian) (Chemical Abstracts, 57, 12903).
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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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246 O.A. Cherkasov and O.N. Tolkach
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Page 277 and 278: 9 Studies on galanthamine extractio
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Page 293 and 294: 272 M. Kreh Gorinova, N.I., Atanass
Page 295 and 296: 274 R.M. Moraes (Katz and Taneck, 1
Page 297 and 298: 276 R.M. Moraes bulbs of many Narci
Page 299 and 300: 278 R.M. Moraes Galanthamine conten
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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: Table 11.1 Continued References Det
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Page 363 and 364: 342 D. Brown cortex and hippocampus
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Page 367 and 368: 346 D. Brown Galanthamine causes br
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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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Narcissus and Daffodil

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