Tropane alkaloids

Tropane alkaloids have a tropane (C4N skeleton +) nucleus. Structurally, these alkaloids synthesize as postcursors of pyrrolines (Figure 57). a, 0, y and x in the tropane pathway are the same as in pyrrolines. Typical tropane alkaloids (e.g., atropine, hyoscyamine, cocaine, tropinone, tropine, littorine and cuscohy-grine) have a strong biological activity, especially as neurotransmitters.

CO2M

L-ornithine

Plants

Urea cycle (animals)

Urea

CO2M

N2M N

L-arginine

Urea

Plants

Agmatine

N2M NM

N-carbamoylputrescine

N2M N

L-arginine

Agmatine

CO2M

N2M NM

N-carbamoylputrescine

Hydrolysis of imine functionality in guanidine system

Hydrolysis of urea

Putrescine 2

N-methylation a

SCoA N

N-methyl-A1-pyrrolinium cation

N-methyl-A1-pyrrolinium cation

N -methylputrescine

Figure 56. Structural development of pyrrolidine alkaloids.

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