Biosynthetic origin of the 1-oxygen of umbelliferone in the root tissue of sweet potato.

Oxidation of p-coumarate at the ortho-position is a key step to form umbelliferone. A tracer analysis using (18)O2 was performed in order to take information about the formation of umbelliferone in the root tissue of sweet potato. Mass fragmentation experiments revealed incorporation of an 18O atom into the 1-position of umbelliferone.

Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana.

Coumarins are derived via the phenylpropanoid pathway in plants. The 2H-1-benzopyran-2-one core structure of coumarins is formed via the ortho-hydroxylation of cinnamates, trans/cis isomerization of the side chain, and lactonization. Ortho-hydroxylation is a key step in coumarin biosynthesis as a branch point from lignin biosynthesis; however, ortho-hydroxylation of cinnamates is not yet fully understood.