200
12
Ashihara H, Sano H, Crozier A (2008) Caffeine and related purine alkaloids: biosynthesis, catabolism,
function and genetic engineering. Phytochemistry 69:841–856. https://doi.org/10.1016/j.phytochem.2007.10.029
Barleben L, Panjikar S, Ruppert M, Koepke J, Stockigt J (2007) Molecular architecture of strictosidine glucosidase: the gateway to the biosynthesis of the monoterpenoid indole alkaloid family. Plant Cell
19:2886–2897. https://doi.org/10.1105/tpc.106.045682
Beaudoin GA, Facchini PJ (2014) Benzylisoquinoline alkaloid biosynthesis in opium poppy. Planta 240:19–
32. https://doi.org/10.1007/s00425-014-2056-8
Bentley KW (2001) β-Phenylethylamines and the isoquinoline alkaloids (July 1999 to June 2000). Nat Prod
Rep 18:148–170. https://doi.org/10.1039/a909672h
Bieri S, Brachet A, Veuthey JL, Christen P (2006) Cocaine distribution in wild Erythroxylum species. J
Ethnopharmacol 103:439–447. https://doi.org/10.1016/j.jep.2005.08.021
Bird DA, Franceschi VR, Facchini PJ (2003) A tale of three cell types: alkaloid biosynthesis is localized to
sieve elements in opium poppy. Plant Cell 15:2626–2635. https://doi.org/10.1105/tpc.015396
Brown TK (2013) Ibogaine in the treatment of substance dependence. Curr Drug Abuse Rev 6:3–16
Bunsupa S, Katayama K, Ikeura E, Oikawa A, Toyooka K, Saito K, Yamazaki M (2012) Lysine decarboxylase
catalyzes the first step of quinolizidine alkaloid biosynthesis and coevolved with alkaloid production
in leguminosae. Plant Cell 24:1202–1216. https://doi.org/10.1105/tpc.112.095885
Bunsupa S, Yamazaki M, Saito K (2016) Lysine-derived alkaloids: overview and update on biosynthesis and
medicinal applications with emphasis on quinolizidine alkaloids. Mini Rev Med Chem 16:1–1. https://
doi.org/10.2174/1389557516666160506151213
Cai B, Jack AM, Lewis RS, Dewey RE, Bush LP (2013) (R)-nicotine biosynthesis, metabolism and translocation in tobacco as determined by nicotine demethylase mutants. Phytochemistry 95:188–196. https://
doi.org/10.1016/j.phytochem.2013.06.012
Chowanski S et al (2016) A review of bioinsecticidal activity of Solanaceae alkaloids. Toxins (Basel):8.
https://doi.org/10.3390/toxins8030060
Courdavault V, Papon N, Clastre M, Giglioli-Guivarc’h N, St-Pierre B, Burlat V (2014) A look inside an alkaloid
multisite plant: the Catharanthus logistics. Curr Opin Plant Biol 19:43–50. https://doi.org/10.1016/j.
pbi.2014.03.010
Croaker A, King GJ, Pyne JH, Anoopkumar-Dukie S, Liu L (2016) Sanguinaria canadensis: traditional medicine, phytochemical composition, biological activities and current uses. Int J Mol Sci 17. https://doi.
org/10.3390/ijms17091414
De Luca V, Salim V, Thamm A, Masada SA, Yu F (2014) Making iridoids/secoiridoids and monoterpenoid indole alkaloids: progress on pathway elucidation. Curr Opin Plant Biol 19:35–42. https://doi.
org/10.1016/j.pbi.2014.03.006
Dehghan E, Shahriari Ahmadi F, Ghotbi Ravandi E, Reed DW, Covello PS, Bahrami AR (2013) An atypical
pattern of accumulation of scopolamine and other tropane alkaloids and expression of alkaloid pathway genes in Hyoscyamus senecionis. Plant Physiol Biochem 70:188–194. https://doi.org/10.1016/j.
plaphy.2013.05.007
Desgagne-Penix I, Facchini PJ (2012) Systematic silencing of benzylisoquinoline alkaloid biosynthetic
genes reveals the major route to papaverine in opium poppy. Plant J 72:331–344. https://doi.
org/10.1111/j.1365-313X.2012.05084.x
Dewey RE, Xie J (2013) Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum. Phytochemistry
94:10–27. https://doi.org/10.1016/j.phytochem.2013.06.002
Drager B (2006) Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism.
Phytochemistry 67:327–337. https://doi.org/10.1016/j.phytochem.2005.12.001
Dugoua JJ, Perri D, Seely D, Mills E, Koren G (2008) Safety and efficacy of blue cohosh (Caulophyllum
thalictroides) during pregnancy and lactation. Can J Clin Pharmacol 15:e66–e73
Dwoskin LP, Crooks PA (2002) A novel mechanism of action and potential use for lobeline as a treatment
for psychostimulant abuse. Biochem Pharmacol 63:89–98
Facchini PJ (2001) Alkaloid biosynthesis in plants: biochemistry, cell biology, molecular regulation, and
metabolic engineering applications. Annu Rev Plant Physiol Plant Mol Biol 52:29–66. https://doi.
org/10.1146/annurev.arplant.52.1.29
Fuell C, Elliott KA, Hanfrey CC, Franceschetti M, Michael AJ (2010) Polyamine biosynthetic diversity in
plants and algae. Plant Physiol Biochem 48:513–520. https://doi.org/10.1016/j.plaphy.2010.02.008
Green BT, Welch KD, Panter KE, Lee ST (2013) Plant toxins that affect nicotinic acetylcholine receptors: a
review. Chem Res Toxicol 26:1129–1138. https://doi.org/10.1021/tx400166f
Chapter 12 · Alkaloids
12
Ashihara H, Sano H, Crozier A (2008) Caffeine and related purine alkaloids: biosynthesis, catabolism,
function and genetic engineering. Phytochemistry 69:841–856. https://doi.org/10.1016/j.phytochem.2007.10.029
Barleben L, Panjikar S, Ruppert M, Koepke J, Stockigt J (2007) Molecular architecture of strictosidine glucosidase: the gateway to the biosynthesis of the monoterpenoid indole alkaloid family. Plant Cell
19:2886–2897. https://doi.org/10.1105/tpc.106.045682
Beaudoin GA, Facchini PJ (2014) Benzylisoquinoline alkaloid biosynthesis in opium poppy. Planta 240:19–
32. https://doi.org/10.1007/s00425-014-2056-8
Bentley KW (2001) β-Phenylethylamines and the isoquinoline alkaloids (July 1999 to June 2000). Nat Prod
Rep 18:148–170. https://doi.org/10.1039/a909672h
Bieri S, Brachet A, Veuthey JL, Christen P (2006) Cocaine distribution in wild Erythroxylum species. J
Ethnopharmacol 103:439–447. https://doi.org/10.1016/j.jep.2005.08.021
Bird DA, Franceschi VR, Facchini PJ (2003) A tale of three cell types: alkaloid biosynthesis is localized to
sieve elements in opium poppy. Plant Cell 15:2626–2635. https://doi.org/10.1105/tpc.015396
Brown TK (2013) Ibogaine in the treatment of substance dependence. Curr Drug Abuse Rev 6:3–16
Bunsupa S, Katayama K, Ikeura E, Oikawa A, Toyooka K, Saito K, Yamazaki M (2012) Lysine decarboxylase
catalyzes the first step of quinolizidine alkaloid biosynthesis and coevolved with alkaloid production
in leguminosae. Plant Cell 24:1202–1216. https://doi.org/10.1105/tpc.112.095885
Bunsupa S, Yamazaki M, Saito K (2016) Lysine-derived alkaloids: overview and update on biosynthesis and
medicinal applications with emphasis on quinolizidine alkaloids. Mini Rev Med Chem 16:1–1. https://
doi.org/10.2174/1389557516666160506151213
Cai B, Jack AM, Lewis RS, Dewey RE, Bush LP (2013) (R)-nicotine biosynthesis, metabolism and translocation in tobacco as determined by nicotine demethylase mutants. Phytochemistry 95:188–196. https://
doi.org/10.1016/j.phytochem.2013.06.012
Chowanski S et al (2016) A review of bioinsecticidal activity of Solanaceae alkaloids. Toxins (Basel):8.
https://doi.org/10.3390/toxins8030060
Courdavault V, Papon N, Clastre M, Giglioli-Guivarc’h N, St-Pierre B, Burlat V (2014) A look inside an alkaloid
multisite plant: the Catharanthus logistics. Curr Opin Plant Biol 19:43–50. https://doi.org/10.1016/j.
pbi.2014.03.010
Croaker A, King GJ, Pyne JH, Anoopkumar-Dukie S, Liu L (2016) Sanguinaria canadensis: traditional medicine, phytochemical composition, biological activities and current uses. Int J Mol Sci 17. https://doi.
org/10.3390/ijms17091414
De Luca V, Salim V, Thamm A, Masada SA, Yu F (2014) Making iridoids/secoiridoids and monoterpenoid indole alkaloids: progress on pathway elucidation. Curr Opin Plant Biol 19:35–42. https://doi.
org/10.1016/j.pbi.2014.03.006
Dehghan E, Shahriari Ahmadi F, Ghotbi Ravandi E, Reed DW, Covello PS, Bahrami AR (2013) An atypical
pattern of accumulation of scopolamine and other tropane alkaloids and expression of alkaloid pathway genes in Hyoscyamus senecionis. Plant Physiol Biochem 70:188–194. https://doi.org/10.1016/j.
plaphy.2013.05.007
Desgagne-Penix I, Facchini PJ (2012) Systematic silencing of benzylisoquinoline alkaloid biosynthetic
genes reveals the major route to papaverine in opium poppy. Plant J 72:331–344. https://doi.
org/10.1111/j.1365-313X.2012.05084.x
Dewey RE, Xie J (2013) Molecular genetics of alkaloid biosynthesis in Nicotiana tabacum. Phytochemistry
94:10–27. https://doi.org/10.1016/j.phytochem.2013.06.002
Drager B (2006) Tropinone reductases, enzymes at the branch point of tropane alkaloid metabolism.
Phytochemistry 67:327–337. https://doi.org/10.1016/j.phytochem.2005.12.001
Dugoua JJ, Perri D, Seely D, Mills E, Koren G (2008) Safety and efficacy of blue cohosh (Caulophyllum
thalictroides) during pregnancy and lactation. Can J Clin Pharmacol 15:e66–e73
Dwoskin LP, Crooks PA (2002) A novel mechanism of action and potential use for lobeline as a treatment
for psychostimulant abuse. Biochem Pharmacol 63:89–98
Facchini PJ (2001) Alkaloid biosynthesis in plants: biochemistry, cell biology, molecular regulation, and
metabolic engineering applications. Annu Rev Plant Physiol Plant Mol Biol 52:29–66. https://doi.
org/10.1146/annurev.arplant.52.1.29
Fuell C, Elliott KA, Hanfrey CC, Franceschetti M, Michael AJ (2010) Polyamine biosynthetic diversity in
plants and algae. Plant Physiol Biochem 48:513–520. https://doi.org/10.1016/j.plaphy.2010.02.008
Green BT, Welch KD, Panter KE, Lee ST (2013) Plant toxins that affect nicotinic acetylcholine receptors: a
review. Chem Res Toxicol 26:1129–1138. https://doi.org/10.1021/tx400166f
Chapter 12 · Alkaloids