title: Glucosylation of phenolic compounds by Pharbitis nil hairy roots: I. Glucosylation of coumarin and flavone derivatives.
abstract: Hairy roots of medicinal morning glory (Pharbitis nil) showed potent glucosylation activity against umbelliferone and aesculetin, so the glucosylation activity against several phenolic compounds was tested. Some coumarin derivatives and flavone derivatives having phenolic hydroxyl groups were incubated with the hairy roots. The coumarin derivatives and flavone derivatives almost disappeared from the culture medium in half a day. In the case of the coumarin derivatives, a 7-hydroxyl group was easily glucosylated. A methyl group at C-8 somewhat decreased the glucosylation to a hydroxyl group at C-7 of the coumarin skeleton. The 4-hydroxy coumarin derivatives were changed to acetophenone-type glucosides by incubation with the hairy roots through decarboxylation. Several flavonol derivatives were tested for glucosylation by the hairy roots. 3-Hydroxy flavone, 3.6-dihydroxyflavone and 3,7-dihydroxyflavone were glucosylated to give 3-glucosylated derivatives. Of these, 3,6-dihydroxyflavone was highly glucosylated, but not 3-hydroxyflavone or 3,7-dihydroxyflavone to the same degree. In the case of the flavones, a 3-hydroxy group could be predominantly glucosylated, and hydroxyl groups on the A and B ring of the flavones affected glucosylation by the hairy roots.
authors.affiliation: School of Bioresources, Hiroshima Prefectural University, Shobara, Hiroshima 727-0023, Japan.
authors.forename: Hideki
authors.initials: H
authors.lastname: Kanho
authors.forename: Sayaka
authors.initials: S
authors.lastname: Yaoya
authors.forename: Tomio
authors.initials: T
authors.lastname: Itani
authors.forename: Takahisa
authors.initials: T
authors.lastname: Nakane
authors.forename: Nobuo
authors.initials: N
authors.lastname: Kawahara
authors.forename: Yoichi
authors.initials: Y
authors.lastname: Takase
authors.forename: Kazuo
authors.initials: K
authors.lastname: Masuda
authors.forename: Masanori
authors.initials: M
authors.lastname: Kuroyanagi
mesh_terms: D003374:Coumarins / Q000032:analysis / Q000737:chemistry*; D044948:Flavonols / Q000032:analysis / Q000737:chemistry*; D006031:Glycosylation; D027741:Ipomoea / Q000378:metabolism*; D018517:Plant Roots / Q000378:metabolism*; D010946:Plants, Medicinal / Q000378:metabolism
chemical_list: D003374:Coumarins; D044948:Flavonols; C030123:coumarin