Biotransformation of naringin and naringenin by cultured Eucalyptus perriniana cells

Abstract The biotransformation of naringin and naringenin was investigated using cultured cells of Eucalyptus perriniana . Naringin ( 1 ) was converted into naringenin 7- O -β- d -glucopyranoside ( 2 , 15%), naringenin ( 3 , 1%), naringenin 5,7- O -β- d -diglucopyranoside ( 4 , 15%), naringenin 4′,7- O -β- d -diglucopyranoside ( 5 , 26%), naringenin 7- O -[6- O -(β- d -glucopyranosyl)]-β- d -glucopyranoside ( 6 , β-gentiobioside, 5%), naringenin 7- O -[6- O -(α- l -rhamnopyranosyl)]-β- d -glucopyranoside ( 7 , β-rutinoside, 3%), and 7- O -β- d -gentiobiosyl-4′- O -β- d -glucopyranosylnaringenin ( 8 , 1%) by cultured cells of E. perriniana . On the other hand, 2 (14%), 4 (7%), 5 (13%), 6 (2%), 7 (1%), naringenin 4′- O -β- d -glucopyranoside ( 9 , 4%), naringenin 5- O -β- d -glucopyranoside ( 10 , 2%), and naringenin 4′,5- O -β- d -diglucopyranoside ( 11 , 5%) were isolated from cultured E. perriniana cells, that had been treated with naringenin ( 3 ). Products, 7- O -β- d -gentiobiosyl-4′- O -β- d -glucopyranosylnaringenin ( 8 ) and naringenin 4′,5- O -β- d -diglucopyranoside ( 11 ), were hitherto unknown.