Senecionine

Senecionine
Names
Other names
Aureine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.125.118
KEGG
Properties
C18H25NO5
Density 1.25 g/cm3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Senecionine is an organic compound with the chemical formula C
18H
25NO
5. It is produced by Senecio species and classified as a pyrrolizidine alkaloid. It has a core structure of retronecine which is further esterified by two Isoleucine to form a 12 member lactone ring. The compound is toxic and as alkaloid of the widespread plant Jacobaea vulgaris also problematic for feed stock and human consumption.[1]

Biosynthesis

In Senecio species, biosynthesis of Senecionine starts from L-Arginine or L-ornithine. Since plants don't have decarboxylase enzyme for L-ornithine, it must be first converted into L-Arginine, which can be readily converted to putrescine. Putrescine gains an aminopropyl group from spermidine in an NAD+ fashion to form homospermidine via homospermidine synthase. The detailed mechanism for this step isn't well understood and it is suspected that imine intermediate is involved. Homospermidine undergo a series of reactions to form the 2 five member rings structure of retronecine. Retronecine is further esterified by two L-isoleucine and modified through a couple of steps to senecionine.

Biosynthesis of senecionine

See also

References

  1. ↑ "Pyrrolizidine Alkaloids—Genotoxicity, Metabolism Enzymes, Metabolic Activation, and Mechanisms". doi:10.1081/DMR-120028426.
  • Dewick, M,Paul (Feb 4, 2009). Medicinal Natural Products. wiley online. pp. 324–325. doi:10.1002/9780470742761. ISBN 9780470742761.
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