Biotransformation of ( RS)-tropic acid in suspension cultures of Coffea arabica, Datura innoxia, Eucalyptus perriniana and Nicotiana tabacum

Abstract

Suspension cultures of Datura innoxia and Nicotiana tabacum are able to convert ( RS)-tropic acid into its glucose esters (2 RS)-3-hydroxy-2-phenylpropionyl β- d-glucopyranoside and (2 RS)-2- O-(3-hydroxy-2-phenylpropionyl)- d-glucose whereas a cultures of Eucalyptus perriniana converts it into its glucoside (2 RS)-3- O-β- d-glucopyranosyl-2-phenylpropionic acid in addition to glucose esters. Suspension cultures of Coffea arabica converts: ( RS)-tropic acid into its glucose, sucrose and isotrehalose esters and a small amount of its glucoside; ( RS)-2-(4-hydroxyphenyl)propionic acid into its glucose and sucrose esters and a small amount of its glucoside; and ( RS)-ethyl 2-(4-hydroxyphenyl)propionate into its gentiobioside. The formation of sucrose esters and linkage of the aglycone to the C-6 position of glucose are characteristic of the biotransformation of carboxylic acids by suspension cultures of C. arabica. The suspension culture of C. arabica selectively converted ( R)-tropic acid into its isotrehalose ester on administration of ( RS)-tropic acid.