201
12
Guirimand G et al (2011) The subcellular organization of strictosidine biosynthesis in Catharanthus roseus
epidermis highlights several trans-tonoplast translocations of intermediate metabolites. FEBS J
278:749–763. https://doi.org/10.1111/j.1742-4658.2010.07994.x
Hagel JM, Facchini PJ (2013) Benzylisoquinoline alkaloid metabolism: a century of discovery and a brave
new world. Plant Cell Physiol 54:647–672. https://doi.org/10.1093/pcp/pct020
Han X et al (2010) The biosynthesis of papaverine proceeds via (S)-reticuline. Phytochemistry 71:1305–
1312. https://doi.org/10.1016/j.phytochem.2010.04.022
Hashimoto T, Matsuda J, Yamada Y (1993) Two-step epoxidation of hyoscyamine to scopolamine is catalyzed by bifunctional hyoscyamine 6 beta-hydroxylase. FEBS Lett 329:35–39
Herbert RB (2003) The biosynthesis of plant alkaloids and nitrogenous microbial metabolitesThis review
and those that preceded it are dedicated to my three teachers who were each a marvellous scientific
inspiration: F. G. Holliman, A. R. Battersby and G. Stork. They were the giants onto whose shoulders I
was privileged to climb. Nat Prod Rep 20:494. https://doi.org/10.1039/b006522f
Horenstein NA, Quadri M, Stokes C, Shoaib M, Papke RL (2017) Cracking the betel nut: cholinergic activity
of areca alkaloids and related compounds nicotine. Tob Res. https://doi.org/10.1093/ntr/ntx187
Huang R, O'Donnell AJ, Barboline JJ, Barkman TJ (2016) Convergent evolution of caffeine in plants by
co- option of exapted ancestral enzymes. Proc Natl Acad Sci U S A 113:10613–10618. https://doi.
org/10.1073/pnas.1602575113
Ilc T, Parage C, Boachon B, Navrot N, Werck-Reichhart D (2016) Monoterpenol oxidative metabolism:
role in plant adaptation and potential applications. Front Plant Sci 7:509. https://doi.org/10.3389/
fpls.2016.00509
Jin Z (2016) Amaryllidaceae and Sceletium alkaloids. Nat Prod Rep. https://doi.org/10.1039/c6np00068a
Jirschitzka J, Schmidt GW, Reichelt M, Schneider B, Gershenzon J, D’Auria JC (2012) Plant tropane alkaloid
biosynthesis evolved independently in the Solanaceae and Erythroxylaceae. Proc Natl Acad Sci U S A
109:10304–10309. https://doi.org/10.1073/pnas.1200473109
Johnston GA (2013) Advantages of an antagonist: bicuculline and other GABA antagonists. Br J Pharmacol
169:328–336. https://doi.org/10.1111/bph.12127
Kajikawa M, Sierro N, Kawaguchi H, Bakaher N, Ivanov NV, Hashimoto T, Shoji T (2017) Genomic insights
into the evolution of the nicotine biosynthesis pathway in tobacco. Plant Physiol 174:999–1011.
https://doi.org/10.1104/pp.17.00070
Kaniakova M, Skrenkova K, Adamek S, Vyskocil F, Krusek J (2014) Different effects of lobeline on neuronal and muscle nicotinic receptors. Eur J Pharmacol 738:352–359. https://doi.org/10.1016/j.
ejphar.2014.05.057
Kohnen KL, Sezgin S, Spiteller M, Hagels H, Kayser O (2018) Localization and organization of scopolamine
biosynthesis in Duboisia myoporoides R. Br. Plant Cell Physiol 59:107–118. https://doi.org/10.1093/
pcp/pcx165
Kramlinger VM, Alvarado Rojas M, Kanamori T, Guengerich FP (2015) Cytochrome P450 3A enzymes catalyze the O6-demethylation of thebaine, a key step in endogenous mammalian morphine biosynthesis. J Biol Chem 290:20200–20210. https://doi.org/10.1074/jbc.M115.665331
Kulma A, Szopa J (2007) Catecholamines are active compounds in plants. Plant Sci 172(3):433–440
Lago J, Rodriguez LP, Blanco L, Vieites JM, Cabado AG (2015) Tetrodotoxin, an extremely potent marine
neurotoxin: distribution, toxicity, origin and therapeutical uses. Mar Drugs 13:6384–6406. https://doi.
org/10.3390/md13106384
Larsson S, Ronsted N (2014) Reviewing Colchicaceae alkaloids – perspectives of evolution on medicinal
chemistry. Curr Top Med Chem 14:274–289
Laue G, Preston CA, Baldwin IT (2000) Fast track to the trichome: induction of N-acyl nornicotines precedes nicotine induction in Nicotiana repanda. Planta 210:510–514. https://doi.org/10.1007/
s004250050038
Laux-Biehlmann A, Mouheiche J, Veriepe J, Goumon Y (2013) Endogenous morphine and its metabolites
in mammals: history, synthesis, localization and perspectives. Neuroscience 233:95–117. https://doi.
org/10.1016/j.neuroscience.2012.12.013
Lee YS, Cho YD (2001) Identification of essential active-site residues in ornithine decarboxylase of
Nicotiana glutinosa decarboxylating both L-ornithine and L-lysine. Biochem J 360:657–665
Lee ST et al (2007) Lupine induced “crooked calf disease” in Washington and Oregon: identification of the
alkaloid profiles in Lupinus sulfureus, Lupinus leucophyllus, and Lupinus sericeus. J Agric Food Chem
55:10649–10655. https://doi.org/10.1021/jf0723110
References
12
Guirimand G et al (2011) The subcellular organization of strictosidine biosynthesis in Catharanthus roseus
epidermis highlights several trans-tonoplast translocations of intermediate metabolites. FEBS J
278:749–763. https://doi.org/10.1111/j.1742-4658.2010.07994.x
Hagel JM, Facchini PJ (2013) Benzylisoquinoline alkaloid metabolism: a century of discovery and a brave
new world. Plant Cell Physiol 54:647–672. https://doi.org/10.1093/pcp/pct020
Han X et al (2010) The biosynthesis of papaverine proceeds via (S)-reticuline. Phytochemistry 71:1305–
1312. https://doi.org/10.1016/j.phytochem.2010.04.022
Hashimoto T, Matsuda J, Yamada Y (1993) Two-step epoxidation of hyoscyamine to scopolamine is catalyzed by bifunctional hyoscyamine 6 beta-hydroxylase. FEBS Lett 329:35–39
Herbert RB (2003) The biosynthesis of plant alkaloids and nitrogenous microbial metabolitesThis review
and those that preceded it are dedicated to my three teachers who were each a marvellous scientific
inspiration: F. G. Holliman, A. R. Battersby and G. Stork. They were the giants onto whose shoulders I
was privileged to climb. Nat Prod Rep 20:494. https://doi.org/10.1039/b006522f
Horenstein NA, Quadri M, Stokes C, Shoaib M, Papke RL (2017) Cracking the betel nut: cholinergic activity
of areca alkaloids and related compounds nicotine. Tob Res. https://doi.org/10.1093/ntr/ntx187
Huang R, O'Donnell AJ, Barboline JJ, Barkman TJ (2016) Convergent evolution of caffeine in plants by
co- option of exapted ancestral enzymes. Proc Natl Acad Sci U S A 113:10613–10618. https://doi.
org/10.1073/pnas.1602575113
Ilc T, Parage C, Boachon B, Navrot N, Werck-Reichhart D (2016) Monoterpenol oxidative metabolism:
role in plant adaptation and potential applications. Front Plant Sci 7:509. https://doi.org/10.3389/
fpls.2016.00509
Jin Z (2016) Amaryllidaceae and Sceletium alkaloids. Nat Prod Rep. https://doi.org/10.1039/c6np00068a
Jirschitzka J, Schmidt GW, Reichelt M, Schneider B, Gershenzon J, D’Auria JC (2012) Plant tropane alkaloid
biosynthesis evolved independently in the Solanaceae and Erythroxylaceae. Proc Natl Acad Sci U S A
109:10304–10309. https://doi.org/10.1073/pnas.1200473109
Johnston GA (2013) Advantages of an antagonist: bicuculline and other GABA antagonists. Br J Pharmacol
169:328–336. https://doi.org/10.1111/bph.12127
Kajikawa M, Sierro N, Kawaguchi H, Bakaher N, Ivanov NV, Hashimoto T, Shoji T (2017) Genomic insights
into the evolution of the nicotine biosynthesis pathway in tobacco. Plant Physiol 174:999–1011.
https://doi.org/10.1104/pp.17.00070
Kaniakova M, Skrenkova K, Adamek S, Vyskocil F, Krusek J (2014) Different effects of lobeline on neuronal and muscle nicotinic receptors. Eur J Pharmacol 738:352–359. https://doi.org/10.1016/j.
ejphar.2014.05.057
Kohnen KL, Sezgin S, Spiteller M, Hagels H, Kayser O (2018) Localization and organization of scopolamine
biosynthesis in Duboisia myoporoides R. Br. Plant Cell Physiol 59:107–118. https://doi.org/10.1093/
pcp/pcx165
Kramlinger VM, Alvarado Rojas M, Kanamori T, Guengerich FP (2015) Cytochrome P450 3A enzymes catalyze the O6-demethylation of thebaine, a key step in endogenous mammalian morphine biosynthesis. J Biol Chem 290:20200–20210. https://doi.org/10.1074/jbc.M115.665331
Kulma A, Szopa J (2007) Catecholamines are active compounds in plants. Plant Sci 172(3):433–440
Lago J, Rodriguez LP, Blanco L, Vieites JM, Cabado AG (2015) Tetrodotoxin, an extremely potent marine
neurotoxin: distribution, toxicity, origin and therapeutical uses. Mar Drugs 13:6384–6406. https://doi.
org/10.3390/md13106384
Larsson S, Ronsted N (2014) Reviewing Colchicaceae alkaloids – perspectives of evolution on medicinal
chemistry. Curr Top Med Chem 14:274–289
Laue G, Preston CA, Baldwin IT (2000) Fast track to the trichome: induction of N-acyl nornicotines precedes nicotine induction in Nicotiana repanda. Planta 210:510–514. https://doi.org/10.1007/
s004250050038
Laux-Biehlmann A, Mouheiche J, Veriepe J, Goumon Y (2013) Endogenous morphine and its metabolites
in mammals: history, synthesis, localization and perspectives. Neuroscience 233:95–117. https://doi.
org/10.1016/j.neuroscience.2012.12.013
Lee YS, Cho YD (2001) Identification of essential active-site residues in ornithine decarboxylase of
Nicotiana glutinosa decarboxylating both L-ornithine and L-lysine. Biochem J 360:657–665
Lee ST et al (2007) Lupine induced “crooked calf disease” in Washington and Oregon: identification of the
alkaloid profiles in Lupinus sulfureus, Lupinus leucophyllus, and Lupinus sericeus. J Agric Food Chem
55:10649–10655. https://doi.org/10.1021/jf0723110
References