Formation of water-soluble vitamin derivatives from lipophilic vitamins by cultured plant cells

Glycosylation of vitamin E, its homologues, and vitamin A by cultured plant cells of Phytolacca americana and Catharanthus roseus was investigated to produce water-soluble vitamin derivatives. Two new compounds, that is, 2,5,7,8-tetramethyl-2-(4-methylpentyl)chroman-6-yl β-d-glucopyranoside and 2,5,7,8-tetramethyl-2-(4,8-dimethylnonyl)chroman-6-yl β-d-glucopyranoside, together with 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)chroman-6-yl β-d-glucopyranoside were isolated from the cultured cells of P. americana following administration of vitamin E and its homologues, that is, 2,5,7,8-tetramethyl-2-(4-methylpentyl)-6-chromanol, 2,5,7,8-tetramethyl-2-(4,8-dimethylnonyl)-6-chromanol and 2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol (vitamin E). On the other hand, glycosylation by C. roseus gave two new compounds, that is, 2,5,7,8-tetramethyl-2-(4-methylpentyl)chroman-6-yl 6-O-β-d-glucopyranosyl-β-d-glucopyranoside and 2,5,7,8-tetramethyl-2-(4,8-dimethylnonyl)chroman-6-yl 6-O-β-d-glucopyranosyl-β-d-glucopyranoside, as well. Furthermore, conversion of vitamin A (retinol) by these cultured cells afforded retinyl β-d-glucopyranoside.