Secologanin is a secoiridoid

monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen func ...

synthesized from geranyl pyrophosphate in the mevalonate pathway. Secologanin then proceeds with

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. Dopamine constitutes about 8 ...

tryptamine Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan. The chemical structure is defined by an indole ─ a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the f ...

to form ipecac and terpene indole alkaloids, respectively.

Biosynthesis

Secologanin biosynthesis begins from geranyl pyrophosphate (GPP) taken from the mevalonate pathway used to make

terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes ...

s. Recent efforts have characterized the entire secologanin biosynthetic pathway. Secologanin is formed from loganin through the action of the enzyme

secologanin synthase In enzymology, a secologanin synthase (, was wrongly classified as in the past) is an enzyme that catalyzes the chemical reaction :loganin + NADPH + H+ + O2 \rightleftharpoons secologanin + NADP+ + 2 H2O The 4 substrates of this enzyme are l ...

. Secologanin is then able to proceed onto produce ipecac and terpene indole alkaloids.

References

{{Reflist Glucosides Methyl esters Aldehydes Vinyl compounds