Tropane Alkaloids: Chemistry, Pharmacology, Biosynthesis and Production

Molecules. 2019 Feb 22;24(4):796. doi: 10.3390/molecules24040796.

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.

Keywords: biosynthesis; biotechnological production; calystegine; chemistry; cocaine; pharmacology; scopolamine; tropane alkaloids.

Publication types

  • Review

MeSH terms

  • Alkaloids / biosynthesis*
  • Alkaloids / chemistry
  • Alkaloids / pharmacology*
  • Erythroxylaceae / chemistry*
  • Gene Expression Regulation, Plant / drug effects
  • Humans
  • Molecular Structure
  • Plant Extracts / biosynthesis
  • Plant Extracts / pharmacology
  • Secondary Metabolism
  • Solanaceae / chemistry*
  • Tropanes / chemical synthesis
  • Tropanes / chemistry
  • Tropanes / pharmacology

Substances

  • Alkaloids
  • Plant Extracts
  • Tropanes