Effect of substituent groups on the glucosyl conjugation of xenobiotic phenols by cultured cells of Gardenia jasminoides

Phenol, nitrophenols and hydroxyphenols added exogenously to Gardenia jasminoides Ellis cell suspension cultures were conjugated to form the corresponding β,d-monoglucosides. The reaction proceeded linearly after the addition of the substrates, indicating participation of constitutive glucosyltransferases in the cultured cells. Nitro substitution, especially in the ortho-position, enhanced the velocity of glucosyl conjugation. Ortho-hydroxyphenol (catechol) was also glucosylated with a higher velocity than phenol.These results suggest that the acidity of a phenolic hydroxyl group and position of a substituent can play important roles in the glucosylation of phenolic compounds by cultured cells of G. jasminoides.