192
12
is synthesized in the roots of Nicotiana (Solanaceae) and is then transported to the aerial
parts of the plant where it can also be found in trichomes (Cai et al. 2013). Nicotine levels
in plants rise upon attacks from herbivores, and the pathway is induced by jasmonate and
wounding. Leaves contain higher levels of nornicotine than of nicotine. Furthermore, in
Nicotiana repanda it was shown that in trichomes nornicotine is acylated with fatty acids
Aspartic acid
Arginine
Quinolinic acid
Nicotinic acid
3,6 Dihydronicotinic acid
Ornithine
Putrescine
N-methyl-∆
1 -pyrrolinium
Nicotine
N´-nitrosonornicotine
(carcinogen)
Nornicotine
Acetoacetic acid
Hygrine
Tr opine
2x Acetyl-CoA
Cocaine
Tropane Alkaloids
Pyrrolidine
Alkaloids
Anabasine
Anatabine
Piperdine
Alkaloids
Glycerin 3-phosphate
∆
1 -Piperideine
Tr opinone
Hyoscyamine
Phenyl-lactyl CoA
Scopolamine
Atropine
Calystegines
Pyridine Alkaloids
H
H
O
O
OH
N
N
H
N
N
N
H 2 N
H 2 N
NH 2
N
H
NH
O
OH
OH
O
O
OH
NH 2
NH 2
+
N
. Fig. 12.5 Schematic overview of the biosynthetic pathway of pyridine alkaloids, pyrrolidine alkaloids, tropane alkaloids and piperidine alkaloids and representative members of various subfamilies
Chapter 12 · Alkaloids
12
is synthesized in the roots of Nicotiana (Solanaceae) and is then transported to the aerial
parts of the plant where it can also be found in trichomes (Cai et al. 2013). Nicotine levels
in plants rise upon attacks from herbivores, and the pathway is induced by jasmonate and
wounding. Leaves contain higher levels of nornicotine than of nicotine. Furthermore, in
Nicotiana repanda it was shown that in trichomes nornicotine is acylated with fatty acids
Aspartic acid
Arginine
Quinolinic acid
Nicotinic acid
3,6 Dihydronicotinic acid
Ornithine
Putrescine
N-methyl-∆
1 -pyrrolinium
Nicotine
N´-nitrosonornicotine
(carcinogen)
Nornicotine
Acetoacetic acid
Hygrine
Tr opine
2x Acetyl-CoA
Cocaine
Tropane Alkaloids
Pyrrolidine
Alkaloids
Anabasine
Anatabine
Piperdine
Alkaloids
Glycerin 3-phosphate
∆
1 -Piperideine
Tr opinone
Hyoscyamine
Phenyl-lactyl CoA
Scopolamine
Atropine
Calystegines
Pyridine Alkaloids
H
H
O
O
OH
N
N
H
N
N
N
H 2 N
H 2 N
NH 2
N
H
NH
O
OH
OH
O
O
OH
NH 2
NH 2
+
N
. Fig. 12.5 Schematic overview of the biosynthetic pathway of pyridine alkaloids, pyrrolidine alkaloids, tropane alkaloids and piperidine alkaloids and representative members of various subfamilies
Chapter 12 · Alkaloids