Secologanin

Secologanin
Names
IUPAC name
Methyl (2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-4-(2-oxoethyl)-3,4-dihydro-2H-pyran-5-carboxylate
Identifiers
19351-63-4
3D model (Jmol) Interactive image
ChEBI CHEBI:18002
ChemSpider 141670
PubChem 161276
Properties
C17H24O10
Molar mass 388.37 g·mol−1
Density 1.42 g/mL
Boiling point 595.5 °C (1,103.9 °F; 868.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Secologanin is a secoiridoid monoterpene synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with dopamine or tryptamine to form ipecac and terpene indole alkaloids, respectively.

Biosynthesis

Secologanin biosynthesis begins from geranyl pyrophosphate (GPP) taken from the mevalonate pathway used to make terpenoids. Recent efforts have characterized the entire secologanin biosynthetic pathway.[1] Secologanin is formed from loganin through the action of the enzyme secologanin synthase. Secologanin is then able to proceed onto produce ipecac and terpene indole alkaloids.[2]

References

  1. Miettinen, Dong, Navrot, Schneider, Burlat, et al. (2014) The seco-iridoid pathway from Catharanthus roseus. Nat Commun. http://www.ncbi.nlm.nih.gov/pmc/articles/pmid/24710322/
  2. "Secologanin Biosynthesis". Retrieved 31 May 2011.
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