Regioselective hydroxylation and glucosylation of flavanones with cultured plant cells of Eucalyptus perriniana.

Ryusuke Hosoda, Yoshiyuki Horio, Kei Shimoda, Manabu Hamada, Hatsuyuki Hamada, Hiroki Hamada

Department of Pharmacology, School of Medicine, Sapporo Medical University, Sapporo 060-8556, Japan.

Natural product communications 2013 Jul

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Cultured plant cells of Eucalyptus perriniana catalyzed reduction, regioselective hydroxylation, and regioselective glycosylation of flavanones. (2S)-Flavanone was converted into (2S)-flavan-4-ol, (2S)-flavan-4,7-diol, (2S)-flavan-7-ol, (2S)-flavan-7-yl glucoside, and (2S)-flavan-7-yl gentiobioside. The cells glucosylated (2S)-flavan-6-ol to (2S)-flavan-6-yl glucoside. (2S)-Flavan-2'-ol was transformed to (2S)-flavan-2',4-diol, (2S)-flavan-2',7-diol, (2S)-flavan-2'-yl glucoside. In addition, (2S)-flavan-4'-ol was transformed to (2S)-flavan-4,4'-diol, (2S)-flavan-4',7-diol, (2S)-flavan-4'-yl glucoside.

Citation

Ryusuke Hosoda, Yoshiyuki Horio, Kei Shimoda, Manabu Hamada, Hatsuyuki Hamada, Hiroki Hamada. Regioselective hydroxylation and glucosylation of flavanones with cultured plant cells of Eucalyptus perriniana. Natural product communications. 2013 Jul;8(7):905-6