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Biotransformation of naringin and naringenin by cultured Eucalyptus perriniana cells
Authors:Kei Shimoda  Naoji Kubota  Koji Taniuchi  Daisuke Sato  Nobuyoshi Nakajima  Hatsuyuki Hamada  Hiroki Hamada
Institution:1. Department of Chemistry, Faculty of Medicine, Oita University, 1-1 Hasama-machi, Oita 879-5593, Japan;2. Department of Life Science, Faculty of Science, Okayama University of Science, 1-1 Ridai-cho, Okayama 700-0005, Japan;3. Industry, Government, and Academic Promotional Center, Regional Cooperative Research Organization, Okayama Prefectural University, Soja, Okayama 719-1197, Japan;4. National Institute of Fitness and Sports in Kanoya, 1 Shiromizu-cho, Kagoshima 891-2390, Japan
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.
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