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Highlights • p -Coumaric acid stimulates geranylation in dill cultured calli. • Boropinic acid promotes farnesylation in dill calli. • New hypothesis on the prenylation biosynthetic pathway. Abstract Cultured calli from Anethum graveolens L. have been previously shown to biosynthetically manipulate selected precursors having a phenylpropanoid core leading to an increase or a decrease in their prenylation. In this article, an extension of previous studies in this field showing how two other cinnamic acid derivatives, namely p -coumaric acid and boropinic acid, are able to exert similar effects using the same experimental model will be reported. Lyophilized calli from A. graveolens has been powdered and extracted by an overnight maceration with EtOH. Selected oxyprenylated cinnamic acid derivatives were then quantified by HPLC analysis coupled to UV/Vis detection. The effect recorded after administration of p -coumaric acid was similar to that evoked by ferulic acid and consisted in a selective increase of its geranylation. The addition of boropinic acid stimulated the biosynthesis of ferulic acid with longer chain like 4′-farnesyloxyferulic acid. This study demonstrated that administration to cultured calli of phenylpropanoids with no free OH moiety has a deep influence on the prenylation biosynthetic pathways and led to the hypothesis that the elongation of the O -side chain of oxyprenylated cinnamic acid derivatives may occur by addition in sequence of isoprenic units. [ABSTRACT FROM AUTHOR]

In this paper we established the effect on the extent of the geranylation step of selected O- prenyl phenylpropanoids by their biosynthetic precursors (e.g. ferulic acid and umbelliferone) in cultured calli from Anethum graveolens L. Lyophilized vegetable material has been extracted by an overnight maceration with EtOH and 3,3-dimethylallyl, geranyl, and farnesyl derivatives of both ferulic acid and umbelliferone quantified by HPLC analysis coupled to UV/Vis detection. In no case culture media supplemented with the parent molecule provided increases in the biosynthesis of the corresponding prenylated secondary metabolite. Quite surprisingly ferulic acid and umbelliferone exerted opposite effects, the first being an elicitor of the only O- geranylation of phenylpropanoid cores while the latter was seen to largely suppress this biosynthetic step. [ABSTRACT FROM AUTHOR]