182
12
derived from geraniol (monoterpene, MEP pathway; see 7 Sect. 10.2 in 7 Chap. 10)
(De Luca et al. 2014; Ilc et al. 2016). This results in strictosidine glucoside (. Fig. 12.2).
The condensation is a Pictet-Spengler-type reaction and is mediated by the secologanin
Indole
Isoquinoline
Tropane
Pyridine
Tryptophan
Tyrosine
Ornithine
Aspartate
Pyrrolizidine
Spermidine
Purine
Putrescine
Quinolizidine
Xanthosine
Piperidine
Lysine
Pyrrolidine
2x
N
HO
NH 2
H
N
N
H
COOH
COOH
NH 2
NH 2
NH 2
NH 2
NH 2
NH 2
N
H
OH
OH
O
O
OH
O
H 2 N
H 2 N
O
O
OH
OH
CO 2 H
H 2 N
CO 2 H
H 2 N
H
N
HN
N
H
N
H
N
N
N
N
N
N
N
N
N
N
. Fig. 12.1 Schematic overview of the main alkaloid backbones and their respective precursors. The
structures of the precursors used to form the alkaloids are marked bold. Chains that are removed are circled
Chapter 12 · Alkaloids
12
derived from geraniol (monoterpene, MEP pathway; see 7 Sect. 10.2 in 7 Chap. 10)
(De Luca et al. 2014; Ilc et al. 2016). This results in strictosidine glucoside (. Fig. 12.2).
The condensation is a Pictet-Spengler-type reaction and is mediated by the secologanin
Indole
Isoquinoline
Tropane
Pyridine
Tryptophan
Tyrosine
Ornithine
Aspartate
Pyrrolizidine
Spermidine
Purine
Putrescine
Quinolizidine
Xanthosine
Piperidine
Lysine
Pyrrolidine
2x
N
HO
NH 2
H
N
N
H
COOH
COOH
NH 2
NH 2
NH 2
NH 2
NH 2
NH 2
N
H
OH
OH
O
O
OH
O
H 2 N
H 2 N
O
O
OH
OH
CO 2 H
H 2 N
CO 2 H
H 2 N
H
N
HN
N
H
N
H
N
N
N
N
N
N
N
N
N
N
. Fig. 12.1 Schematic overview of the main alkaloid backbones and their respective precursors. The
structures of the precursors used to form the alkaloids are marked bold. Chains that are removed are circled
Chapter 12 · Alkaloids