Biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its related anthraquinone in a Sesamum indicum hairy root culture

An isotope administration experiment with [1– 13C]glucose was conducted to clarify the biosynthetic origin of quinone derivatives produced by Sesamum indicum. [Display omitted] ► The geranyl group in geranylnaphthoquinone was formed via the MEP pathway. ► The ring moiety in geranylnaphthoquinone was formed via the shikimate pathway. ► Prenylation occurred at C-2 in 1,4-dihydroxy-2-naphthoate. ► Geranylnaphthoquinone and its related anthraquinone had the same biosynthetic origin. In order to clarify the biosynthetic origin of 2-geranyl-1,4-naphthoquinone and its biogenetically related anthraquinone, which are possible intermediates of anthrasesamones, [1– 13C]glucose was administered to a hairy root culture of Sesamum indicum. The labeling patterns of these quinone derivatives indicated that the naphthoquinone ring and geranyl side-chain of geranylnaphthoquinone were respectively biosynthesized through the shikimate and methylerythritol phosphate pathways, and that these quinone derivatives have the same biosynthetic origin.