Abstract
Tropane alkaloids (TA) are valuable secondary plant metabolites which are mostly found in high concentrations in the Solanaceae and Erythroxylaceae families. The TAs, which are characterized by their unique bicyclic tropane ring system, can be divided into three major groups: hyoscyamine and scopolamine, cocaine and calystegines. Although all TAs have the same basic structure, they differ immensely in their biological, chemical and pharmacological properties. Scopolamine, also known as hyoscine, has the largest legitimate market as a pharmacological agent due to its treatment of nausea, vomiting, motion sickness, as well as smooth muscle spasms while cocaine is the 2nd most frequently consumed illicit drug globally. This review provides a comprehensive overview of TAs, highlighting their structural diversity, use in pharmaceutical therapy from both historical and modern perspectives, natural biosynthesis in planta and emerging production possibilities using tissue culture and microbial biosynthesis of these compounds.
Highlights
Alkaloids are naturally occurring compounds containing one or more nitrogen atoms
Tropane alkaloids (TA) are either esters of 3α-tropanole or, to a lesser extent, 3β-tropanole and can be distinguished into three groups: TAs from Solanaceae plants like hyoscyamine and scopolamine, coca alkaloids like cocaine from Erythoxylum coca and the recently discovered calystegines group, which are polyhydroxylated nortropane alkaloids (NTAs) mainly occurring in Convolvulaceae, Solanaceae, Moraceae, Erythrocylaceae and Brassicaceae (Figure 1 Structure of the tropane skeleton and the three major groups of TAs derived from) [2]
Cocaine manifests its effects in the synaptic cleft by inhibiting the dopamine, noradrenaline and serotonin reuptake while scopolamine acts as a competitive muscarinic receptor antagonist
Summary
Alkaloids are naturally occurring compounds containing one or more nitrogen atoms. The name is derived from the basic nature of many members of this group, alkaloids from “alkaline-like”. Tropane alkaloids (TAs) are a specific class of alkaloid and can be defined as all molecules that possess a tropane ring system (Figure 1 Structure of the tropane skeleton (green box) and the three major groups of TAs derived from, green box) [1]. TAs are either esters of 3α-tropanole (tropine) or, to a lesser extent, 3β-tropanole (pseudotropine) and can be distinguished into three groups: TAs from Solanaceae plants like hyoscyamine and scopolamine, coca alkaloids like cocaine from Erythoxylum coca and the recently discovered calystegines group, which are polyhydroxylated nortropane alkaloids (NTAs) mainly occurring in Convolvulaceae, Solanaceae, Moraceae, Erythrocylaceae and Brassicaceae (Figure 1 Structure of the tropane skeleton (green box) and the three major groups of TAs derived from) [2].
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