Chem. Pharm. Bull. 53(4) 361—365 (2005)

zogenes are differentiated cells capable of the biosynthesis of secondary metabolites. Hairy roots also have a high rate of proliferation. They are therefore expected to become widely used culture systems for the production of useful secondary metabolites and for studies on the production of biologically active compounds and transformation of organic substrates. We reported the production of a stress compound, umbelliferone, upon treatment of morning glory (Pharbitis nil) hairy roots with CuSO4 and that umbelliferone was highly glucosylated to a glucoside, skimmin, by P. nil hairy roots. We further reported the glucosylation of phenolic compounds, such as coumarin and flavone derivatives by the hairy roots. Many types of secondary metabolites exist as glycosides such as saponines, terpene glycosides, flavone glycosides, and other phenolic glycosides. Some glycosides exist as prebioactive specimens, detoxicated specimens, and bioactive specimens. Thus the biotransformation of various organic substrates to glycosides by plant cell cultures should be useful for supplying glucosides. We are also interested in the glucosylation of other simple phenolic compounds. Vanillin is a common natural product with a benzaldehyde skeleton. The 3and 4-positions of benzaldehyde and acetophenone derivatives correspond to the 6and 7-positions of coumarin derivatives. Thus the biotransformation of benzaldehydeand acetophenone-type derivatives were carried out using P. nil hairy roots. This report deals with the glucosylation of benzaldehydeand acetophenone-type derivatives having phenolic hydroxyl groups or not, and the reduction of a formyl and a carbonyl group of these compounds.