Identification and Accumulation of 1-<i>O</i>-<i>trans</i>-Cinnamoyl-β-<scp>d</scp>-glucopyranose in Developing Strawberry Fruit (<i>Fragaria ananassa </i>Duch. Cv. Kent)

Abstract

Strawberry fruit ( Fragaria ananassa Duch. cv. Kent) were discovered as the first food source of 1- O - trans -cinnamoyl-β- d -glucopyranose. Isolation was performed by preparative HPLC of a solid phase desorbate. Identification was carried out by comparing chromatographic properties, NMR spectroscopy data, and specific β-glucosidic cleavage. The accumulation was monitored by HPLC. A sharp rise of the concentration of 1- O - trans -cinnamoyl-β- d -glucopyranose was observed 21 days after anthesis and was related to general phenylpropanoid metabolism. 1- O - trans -Cinnamoyl-β- d -glucopyranose is discussed as a metabolic link between phenylalanine ammonia-lyase-mediated cinnamic acid and 1- O - p -coumaroyl-β- d -glucopyranose formation. The cinnamoyl ester may be the true precursor of volatile cinnamates in strawberry flavor. Keywords: Strawberry; Fragaria ananassa; 1- O - trans -cinnamoyl-β- d -glucopyranose; phenylpropanoid metabolism; glucoconjugate; flavor; HPLC