Emission of 2-phenylethanol from its β-d-glucopyranoside and the biogenesis of these compounds from [2H8] l-phenylalanine in rose flowers

Abstract The hydrolysis of 2-phenylethyl β- d -glucopyranoside ( 3 ) was found to be partially inhibited by feeding with 2-phenyl- N -glucosyl-acetamidiumbromide ( 8 ), a β-glucosidase inhibitor, resulting in a decrease in the diurnal emission of 2-phenylethanol ( 2 ) from Rosa damascena Mill. flowers. Detection of [1,1,2,2′,3′,4′,5′,6′- 2 H 8 ]- 2 and [1,2,2′,3′,4′,5′,6′- 2 H 7 ]- 2 from R . ‘Hoh-Jun’ flowers fed with [1,1,2,2′,3′,4′,5′,6′- 2 H 8 ]- 3 suggested that β-glucosidase, alcohol dehydrogenase, and reductase might be involved in scent emission. Comprehensive GC-SIM analyses revealed that [1,2,2,2′,3′,4′,5′,6′- 2 H 8 ]- 2 and [1,2,2,2′,3′,4′,5′,6′- 2 H 8 ]- 3 must be biosynthesized from [1,2,2,2′,3′,4′,5′6′- 2 H 8 ] l -phenylalanine ( [ 2 H 8 ]- 1 ) with a retention of the deuterium atom at α-position of [ 2 H 8 ]- 1 .