202
12
Lee SH, Kim HY, Back SY, Han HK (2018) Piperine-mediated drug interactions and formulation strategy for
piperine: recent advances and future perspectives. Expert Opin Drug Metab Toxicol 14:43–57. https://
doi.org/10.1080/17425255.2018.1418854
Lindigkeit R, Biller A, Buch M, Schiebel HM, Boppre M, Hartmann T (1997) The two facies of pyrrolizidine
alkaloids: the role of the tertiary amine and its N-oxide in chemical defense of insects with acquired
plant alkaloids. Eur J Biochem 245:626–636
Liscombe DK, Facchini PJ (2008) Evolutionary and cellular webs in benzylisoquinoline alkaloid biosynthesis. Curr Opin Biotechnol 19:173–180. https://doi.org/10.1016/j.copbio.2008.02.012
Luk LY, Bunn S, Liscombe DK, Facchini PJ, Tanner ME (2007) Mechanistic studies on norcoclaurine synthase
of benzylisoquinoline alkaloid biosynthesis: an enzymatic Pictet-Spengler reaction. Biochemistry
46:10153–10161. https://doi.org/10.1021/bi700752n
Meghwal M, Goswami TK (2013) Piper nigrum and piperine: an update. Phytother Res 27:1121–1130.
https://doi.org/10.1002/ptr.4972
Mejean A, Paci G, Gautier V, Ploux O (2014) Biosynthesis of anatoxin-a and analogues (anatoxins) in cyanobacteria. Toxicon 91:15–22. https://doi.org/10.1016/j.toxicon.2014.07.016
Ober D, Kaltenegger E (2009) Pyrrolizidine alkaloid biosynthesis, evolution of a pathway in plant secondary metabolism. Phytochemistry 70:1687–1695. https://doi.org/10.1016/j.phytochem.2009.
05.017
Panter KE, Keeler RF (1993) Quinolizidine and piperidine alkaloid teratogens from poisonous plants and
their mechanism of action in animals. Vet Clin North Am Food Anim Pract 9:33–40
Pelagio-Flores R, Ortiz-Castro R, Mendez-Bravo A, Macias-Rodriguez L, Lopez-Bucio J (2011) Serotonin, a
tryptophan-derived signal conserved in plants and animals, regulates root system architecture probably acting as a natural auxin inhibitor in Arabidopsis thaliana. Plant Cell Physiol 52:490–508. https://
doi.org/10.1093/pcp/pcr006
Petersson EV et al (2013) Glycoalkaloid and calystegine levels in table potato cultivars subjected to wounding, light, and heat treatments. J Agric Food Chem 61:5893–5902. https://doi.org/10.1021/jf400318p
Pienkny S, Brandt W, Schmidt J, Kramell R, Ziegler J (2009) Functional characterization of a novel benzylisoquinoline O-methyltransferase suggests its involvement in papaverine biosynthesis in opium
poppy (Papaver somniferum L). Plant J 60:56–67. https://doi.org/10.1111/j.1365-313X.2009.03937.x
Pramod KK, Singh S, Jayabaskaran C (2010) Biochemical and structural characterization of recombinant
hyoscyamine 6beta-hydroxylase from Datura metel L. Plant Physiol Biochem 48:966–970. https://doi.
org/10.1016/j.plaphy.2010.09.003
Rao RB, Hoffman RS (2002) Nicotinic toxicity from tincture of blue cohosh (Caulophyllum thalictroides)
used as an abortifacient. Vet Hum Toxicol 44:221–222
Ren Z et al (2017) The biosynthesis pathway of swainsonine, a new anticancer drug from three endophytic
fungi. J Microbiol Biotechnol 27:1897–1906. https://doi.org/10.4014/jmb.1709.09003
Ruan J, Yang M, Fu P, Ye Y, Lin G (2014) Metabolic activation of pyrrolizidine alkaloids: insights into the
structural and enzymatic basis. Chem Res Toxicol 27:1030–1039. https://doi.org/10.1021/tx500071q
Samanani N, Park SU, Facchini PJ (2005) Cell type-specific localization of transcripts encoding nine consecutive enzymes involved in protoberberine alkaloid biosynthesis. Plant Cell 17:915–926. https://
doi.org/10.1105/tpc.104.028654
Samanani N, Alcantara J, Bourgault R, Zulak KG, Facchini PJ (2006) The role of phloem sieve elements
and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy. Plant J 47:547–563.
https://doi.org/10.1111/j.1365-313X.2006.02801.x
Savage TJ, Smith GJ, Clark AT, Saucedo PN (2012) Condensation of the isoprenoid and amino precursors
in the biosynthesis of domoic acid. Toxicon 59:25–33. https://doi.org/10.1016/j.toxicon.2011.10.010
Schmidt GW et al (2015) The last step in cocaine biosynthesis is catalyzed by a BAHD acyltransferase. Plant
Physiol 167:89–101. https://doi.org/10.1104/pp.114.248187
Scholl Y, Hoke D, Drager B (2001) Calystegines in Calystegia sepium derive from the tropane alkaloid pathway. Phytochemistry 58:883–889
Soares AR, Marchiosi R, Siqueira-Soares Rde C, Barbosa de Lima R, Dantas dos Santos W, Ferrarese-Filho O
(2014) The role of L-DOPA in plants. Plant Signal Behav 9:e28275. https://doi.org/10.4161/psb.28275
Stevens LH, Blom TJ, Verpoorte R (1993) Subcellular localization of tryptophan decarboxylase, strictosidine synthase and strictosidine glucosidase in suspension cultured cells of Catharanthus roseus and
Tabernaemontana divaricata. Plant Cell Rep 12:573–576. https://doi.org/10.1007/BF00233063
Stockigt J, Panjikar S (2007) Structural biology in plant natural product biosynthesis--architecture of
enzymes from monoterpenoid indole and tropane alkaloid biosynthesis. Nat Prod Rep 24:1382–1400.
https://doi.org/10.1039/b711935f
Chapter 12 · Alkaloids
12
Lee SH, Kim HY, Back SY, Han HK (2018) Piperine-mediated drug interactions and formulation strategy for
piperine: recent advances and future perspectives. Expert Opin Drug Metab Toxicol 14:43–57. https://
doi.org/10.1080/17425255.2018.1418854
Lindigkeit R, Biller A, Buch M, Schiebel HM, Boppre M, Hartmann T (1997) The two facies of pyrrolizidine
alkaloids: the role of the tertiary amine and its N-oxide in chemical defense of insects with acquired
plant alkaloids. Eur J Biochem 245:626–636
Liscombe DK, Facchini PJ (2008) Evolutionary and cellular webs in benzylisoquinoline alkaloid biosynthesis. Curr Opin Biotechnol 19:173–180. https://doi.org/10.1016/j.copbio.2008.02.012
Luk LY, Bunn S, Liscombe DK, Facchini PJ, Tanner ME (2007) Mechanistic studies on norcoclaurine synthase
of benzylisoquinoline alkaloid biosynthesis: an enzymatic Pictet-Spengler reaction. Biochemistry
46:10153–10161. https://doi.org/10.1021/bi700752n
Meghwal M, Goswami TK (2013) Piper nigrum and piperine: an update. Phytother Res 27:1121–1130.
https://doi.org/10.1002/ptr.4972
Mejean A, Paci G, Gautier V, Ploux O (2014) Biosynthesis of anatoxin-a and analogues (anatoxins) in cyanobacteria. Toxicon 91:15–22. https://doi.org/10.1016/j.toxicon.2014.07.016
Ober D, Kaltenegger E (2009) Pyrrolizidine alkaloid biosynthesis, evolution of a pathway in plant secondary metabolism. Phytochemistry 70:1687–1695. https://doi.org/10.1016/j.phytochem.2009.
05.017
Panter KE, Keeler RF (1993) Quinolizidine and piperidine alkaloid teratogens from poisonous plants and
their mechanism of action in animals. Vet Clin North Am Food Anim Pract 9:33–40
Pelagio-Flores R, Ortiz-Castro R, Mendez-Bravo A, Macias-Rodriguez L, Lopez-Bucio J (2011) Serotonin, a
tryptophan-derived signal conserved in plants and animals, regulates root system architecture probably acting as a natural auxin inhibitor in Arabidopsis thaliana. Plant Cell Physiol 52:490–508. https://
doi.org/10.1093/pcp/pcr006
Petersson EV et al (2013) Glycoalkaloid and calystegine levels in table potato cultivars subjected to wounding, light, and heat treatments. J Agric Food Chem 61:5893–5902. https://doi.org/10.1021/jf400318p
Pienkny S, Brandt W, Schmidt J, Kramell R, Ziegler J (2009) Functional characterization of a novel benzylisoquinoline O-methyltransferase suggests its involvement in papaverine biosynthesis in opium
poppy (Papaver somniferum L). Plant J 60:56–67. https://doi.org/10.1111/j.1365-313X.2009.03937.x
Pramod KK, Singh S, Jayabaskaran C (2010) Biochemical and structural characterization of recombinant
hyoscyamine 6beta-hydroxylase from Datura metel L. Plant Physiol Biochem 48:966–970. https://doi.
org/10.1016/j.plaphy.2010.09.003
Rao RB, Hoffman RS (2002) Nicotinic toxicity from tincture of blue cohosh (Caulophyllum thalictroides)
used as an abortifacient. Vet Hum Toxicol 44:221–222
Ren Z et al (2017) The biosynthesis pathway of swainsonine, a new anticancer drug from three endophytic
fungi. J Microbiol Biotechnol 27:1897–1906. https://doi.org/10.4014/jmb.1709.09003
Ruan J, Yang M, Fu P, Ye Y, Lin G (2014) Metabolic activation of pyrrolizidine alkaloids: insights into the
structural and enzymatic basis. Chem Res Toxicol 27:1030–1039. https://doi.org/10.1021/tx500071q
Samanani N, Park SU, Facchini PJ (2005) Cell type-specific localization of transcripts encoding nine consecutive enzymes involved in protoberberine alkaloid biosynthesis. Plant Cell 17:915–926. https://
doi.org/10.1105/tpc.104.028654
Samanani N, Alcantara J, Bourgault R, Zulak KG, Facchini PJ (2006) The role of phloem sieve elements
and laticifers in the biosynthesis and accumulation of alkaloids in opium poppy. Plant J 47:547–563.
https://doi.org/10.1111/j.1365-313X.2006.02801.x
Savage TJ, Smith GJ, Clark AT, Saucedo PN (2012) Condensation of the isoprenoid and amino precursors
in the biosynthesis of domoic acid. Toxicon 59:25–33. https://doi.org/10.1016/j.toxicon.2011.10.010
Schmidt GW et al (2015) The last step in cocaine biosynthesis is catalyzed by a BAHD acyltransferase. Plant
Physiol 167:89–101. https://doi.org/10.1104/pp.114.248187
Scholl Y, Hoke D, Drager B (2001) Calystegines in Calystegia sepium derive from the tropane alkaloid pathway. Phytochemistry 58:883–889
Soares AR, Marchiosi R, Siqueira-Soares Rde C, Barbosa de Lima R, Dantas dos Santos W, Ferrarese-Filho O
(2014) The role of L-DOPA in plants. Plant Signal Behav 9:e28275. https://doi.org/10.4161/psb.28275
Stevens LH, Blom TJ, Verpoorte R (1993) Subcellular localization of tryptophan decarboxylase, strictosidine synthase and strictosidine glucosidase in suspension cultured cells of Catharanthus roseus and
Tabernaemontana divaricata. Plant Cell Rep 12:573–576. https://doi.org/10.1007/BF00233063
Stockigt J, Panjikar S (2007) Structural biology in plant natural product biosynthesis--architecture of
enzymes from monoterpenoid indole and tropane alkaloid biosynthesis. Nat Prod Rep 24:1382–1400.
https://doi.org/10.1039/b711935f
Chapter 12 · Alkaloids