in good yield. Euglena gracilis could convert acetophenone to 2-phenylethanol; however, its enantio-excess is very poor (10%) (Takahashi, 1994).
Raspberry ketone (566) and zingerone (574) are the major components of raspberry (Rubus idaeus) and ginger (Zingeber officinale) and these are used as food additive and spice. Two substrates were incubated with the Phytolacca americana cultured cells for 3 days to produce two secondary alcohols (567, 568) as well as five glucosides (569-572) from 566, and a secondary alcohol (576) and four glycoside products (575, 577-579) from 574. In the case of raspberry ketone, phenolic hydroxyl group was preferably glycosylated after the reduction of carbonyl group of the substrate occurred. It is interesting to note that one more hydroxyl group was introduced into the benzene ring to give 568, which were further glycosylated one of the phenolic hydroxyl groups and no glycocide of the secondary alcohol at C2 were obtained (Figure 15.161).
On the other hand, zingerone (574) was converted into 576, followed by glycosylation to give both glucosides (577, 578) of phenolic and secondary hydroxyl groups and a diglucoside (579) of both phenolic and secondary hydroxyl group in the molecule. It is the first report on the introduction of individual glucose residues onto both phenolic and secondary hydroxyl groups by cultured plant cells (Shimoda et al., 2007) (Figure 15.162).
Thymol (580), carvacrol (583), and eugenol (586) were glucosylated by glycosyl transferase of cell-cultured Eucalyptus perriniana to each glucoside (581, 3%; 584, 5%; 587, 7%) and gentiobioside
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