Reviewing Colchicaceae alkaloids - perspectives of evolution on medicinal chemistry

Sonny Larsson, Nina Rønsted, Sonny Larsson, Nina Rønsted

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.

Figures

Fig. (1)
Fig. (1)
Hypothetical network of phenethylisoquinoline derived alkaloids based on proposed biosynthesis, feeding experiments and analogies of pathways elucidated for benzylisoquinoline alkaloids. A: phenethylisoquinolines; B: homoproaporphines; C: homoaporphines; D: androcymbines; E: colchicines; F: allocolchicines; G: lumicolchicines; H: dibenzo[d,f]azecines; I: homoerythrinans; and J: cephalotaxines.
Fig. (2)
Fig. (2)
Structural diversity of the phenethylisoquinoline alkaloids in Colchicaceae.
Fig. (3)
Fig. (3)
Structural diversity of the homoproaporphine alkaloids in Colchicaceae.
Fig. (4)
Fig. (4)
Structural diversity of the homoaporphine alkaloids in Colchicaceae.
Fig. (5)
Fig. (5)
Structural diversity of the androcymbine (homomorphinan) alkaloids in Colchicaceae.
Fig. (6)
Fig. (6)
Structural diversity of the colchicine-type alkaloids in Colchicaceae.
Fig. (7)
Fig. (7)
Structural diversity of the allocolchicine alkaloids in Colchicaceae. a) suhailamine may be an isomer of allocolchicine and not a synonym of that compound.
Fig. (8)
Fig. (8)
Structural diversity of the lumicolchicine alkaloids in Colchicaceae.
Fig. (9)
Fig. (9)
Structural diversity of the homoerythrinan alkaloids in Colchicaceae.
Fig. (10)
Fig. (10)
Structural diversity of miscellaneous phenethylisoquinoline alkaloids in Colchicaceae.
Fig. (11)
Fig. (11)
The phylogenetic hypothesis and classification for Colchicaceae modified from Vinnersten and co-workers [46, 47]. The dendrogram clearly shows that the groups not traditionally associated with phenethylisoquinoline alkaloids constitute the basal clades of the family. As further discussed in the text this highlights them as potential new sources of Colchicaceae alkaloids, or even new structural types of phenethylisoquinoline alkaloids.

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