Narcissus and Daffodil

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Figure 6.4 Oxidative phenyl-phenyl coupling in Amaryllidaceae alkaloids. Figure 6.5 Alkaloids proceeding from an ortho-para′ coupling.
166 J. Bastida and F. Viladomat Figure 6.6 Biosynthesis of lycorine (1) with inversion of the configuration. Figure 6.7 Conversion of galanthine (7) to narcissidine (16) via epoxide (86). tritiated lycorine (1) by Narcissus × incomparabilis cv. Deanna Durbin, which not only demonstrates the previously mentioned conversion but also indicates that the C-2 hydroxyl group of lycorine (1) is derived by allylic oxidation of either norpluviine (12) or caranine (10) (Battersby et al., 1964). Regarding the conversion of [2β- 3 H, 8-OMe- 14 C]pluviine (11) into galanthine (7), in Narcissus pseudonarcissus cv. King Alfred, the retention of 79% of the tritium label confirms that hydroxylation of C-2 may occur with inversion of configuration (Harken et al., 1976). It was considered (Fuganti et al., 1974a) that another analogous epoxide 86 could give narcissidine (16) in the way shown by loss of the pro-S hydrogen from C-11, galanthine (7) being a suitable substrate for epoxidation. Labelled [α- 14 C, β- 3 H]-O-methylnorbelladine (80), when fed to Narcissus x incomparabilis cv. Sempre Avanti, afforded galanthine (7) (98% of tritium retention) and narcissidine (16) (46% tritium retention). Loss of hydrogen from C-11 of galanthine (7) was therefore stereospecific. In this decade, Kihara et al. (1992) have isolated a new alkaloid, incartine (86), from flowers of Lycoris incarnata, which could be considered to be the biosynthetic intermediate of this pathway (Figure 6.7). The biological conversion of protocatechuic aldehyde into lycorenine (31), which proceeds via O-methylnorbelladine (80) and norpluviine (12), first involves a reduction of the aldehyde carbonyl, and afterwards, in the generation of lycorenine (31), oxidation of this same carbon atom. The absolute stereochemistry of these processes has been elucidated in subsequent experiments (Fuganti and Mazza, 1973), and the results show that hydrogen addition and removal take place on the re-face of the molecules concerned (Hanson, 1966), the hydrogen initially introduced being the one later removed (Fuganti and Mazza, 1971a). It is noteworthy that norpluviine (12), unlike pluviine (11), is converted in Narcissus pseudonarcissus cv. King Alfred primarily to alkaloids of the homolycorine type. Benzylic oxidation
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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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Page 153 and 154: 132 J.B. Briggs Table 5.1 Typical g
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Page 165 and 166: Table 6.1 Narcissus alkaloid struct
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Page 171 and 172: Table 6.1f Continued MeO Alkaloid n
Page 173 and 174: Table 6.2 Continued Species* Alkalo
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Page 193 and 194: Table 6.3 Continued Alkaloid* Formu
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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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Table 11.1 Continued References Det
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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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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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