Reviewing Colchicaceae Alkaloids – Perspectives of Evolution on Medicinal Chemistry

Abstract

The subject of chemosystematics has provided insight to both botanical classification and drug development. However, degrees of subjectivity in botanical classifications and limited understanding of the evolution of chemical characters and their biosynthetic pathways has often hampered such studies. In this review an approach of taking phylogenetic classification into account in evaluating colchicine and related phenethylisoquinoline alkaloids from the family Colchicaceae will be applied. Following on the trends of utilizing evolutionary reasoning in inferring mechanisms in eg. drug resistance in cancer and infections, this will exemplify how thinking about evolution can influence selection of plant material in drug lead discovery, and how knowledge about phylogenetic relationships may be used to evaluate predicted biosynthetic pathways.

Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction

“…1 Secondary, N-H bearing, allylic lactams are highly valued synthons for accessing a diverse array of such ring systems embedded within complex structures. In addition, allylic lactams themselves are prevalent scaffolds within bioactive molecules.…”

Phytochemical Profile and Biological Properties of Colchicum triphyllum (Meadow Saffron)

“…Overall, our findings revealed a higher discrimination potential of alkaloids when compared to polyphenols. To date, more than 150 structurally elucidated alkaloids have been described for Colchicaceae genera [24]. In particular, eight distinct structural types of alkaloids characterize the Colchicaceae family, being phenethylisoquinolines (e.g., autumnaline), homoproaporphines (e.g., jolantine), homoaporphines (e.g., merobustine), androcymbines (e.g., szovitsidine), colchicines (e.g., colchicine), allocolchicines (e.g., jerusalemine), lumicolchicines (e.g., γ-lumicolchicine), and homoerythrinans (e.g., taxodine).…”

A Novel Approach for Production of Colchicine as a Plant Secondary Metabolite by in Vitro Plant Cell and Tissue Cultures

“…Plants of both genera Colchicum and Gloriosa contain colchicine in toxic amounts. By applying an approach of taking phylogenetic classification into account for the evaluation, Larsson and Ronsted (2014) assorted Colchicaceae alkaloids under eight different structural types, such as phenethylisoquinolines, homoproaporphines, homoaporphines, androcymbines, colchicines, allocolchicines, lumicolchicines and homoerythrinans [28].…”