Biotransformation of naringin and naringenin by cultured Eucalyptus perriniana cells.
The biotransformation of naringin and naringenin was investigated using cultured cells of Eucalyptus perriniana. Naringin (1) was converted into naringenin 7-O-beta-D-glucopyranoside (2, 15%), naringenin (3, 1%), naringenin 5,7-O-beta-D-diglucopyranoside (4, 15%), naringenin 4',7-O-beta-D-diglucopyranoside (5, 26%), naringenin 7-O-[6-O-(beta-D-glucopyranosyl)]-beta-d-glucopyranoside (6, beta-gentiobioside, 5%), naringenin 7-O-[6-O-(alpha-l-rhamnopyranosyl)]-beta-D-glucopyranoside (7, beta-rutinoside, 3%), and 7-O-beta-D-gentiobiosyl-4'-O-beta-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-beta-D-glucopyranoside (9, 4%), naringenin 5-O-beta-D-glucopyranoside (10, 2%), and naringenin 4',5-O-beta-D-diglucopyranoside (11, 5%) were isolated from cultured E. perriniana cells, that had been treated with naringenin (3). Products, 7-O-beta-D-gentiobiosyl-4'-O-beta-D-glucopyranosylnaringenin (8) and naringenin 4',5-O-beta-D-diglucopyranoside (11), were hitherto unknown.
Shimoda
Kei
K
Department of Chemistry, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan.
Kubota
Naoji
N
Taniuchi
Koji
K
Sato
Daisuke
D
Nakajima
Nobuyoshi
N
Hamada
Hatsuyuki
H
Hamada
Hiroki
H
D001711:Biotransformation; D002478:Cells, Cultured; D005052:Eucalyptus / Q000166:cytology / Q000378:metabolism*; D044950:Flavanones / Q000378:metabolism* / Q000494:pharmacology; D047309:Flavones / Q000302:isolation & purification* / Q000378:metabolism; D005960:Glucosides / Q000302:isolation & purification* / Q000378:metabolism; D015394:Molecular Structure
D044950:Flavanones; D047309:Flavones; D005960:Glucosides; C005273:naringenin; C005274:naringin