title: [Sugar Chain Construction of Functional Natural Products Using Plant Glucosyltransferases].
abstract: Plant secondary product glycosyltransferases belong to family 1 of the glycosyltransferase superfamily and mediate the transfer of a glycosyl residue from activated nucleotide sugars to lipophilic small molecules, thus affecting the solubility, stability and pharmacological activities of the sugar-accepting compounds. The biotechnological application of plant glycosyltransferases in glycoside synthesis has attracted attention because enzymatic glycosylation offers several advantages over chemical methods, including (1) avoiding the use of harsh conditions and toxic catalysts, (2) providing strict control of regio-and stereo-selectivity and (3) high efficiency. This review describes the in vivo and in vitro glycosylation of natural organic compounds using glycosyltransferases, focusing on our investigation of enzymatic synthesis of curcumin glycosides. Our current efforts toward functional characterization of some glycosyltransferases involved in the biosynthesis of iridoids and crocin, as well as in the sugar chain elongation of quercetin glucosides, are described. Finally, I describe the relationship of the structure of sugar chains and the intestinal absorption which was investigated using chemoenzymatically synthesized quercetin glycosides.
authors.affiliation: Department of Pharmacognosy, Graduate School of Pharmaceutical Sciences, Nagoya City University.
authors.forename: Hajime
authors.initials: H
authors.lastname: Mizukami
mesh_terms: D000818:Animals; D001688:Biological Products / Q000737:chemistry; D002241:Carbohydrates; D002338:Carotenoids / Q000096:biosynthesis; D003474:Curcumin; D005964:Glucosyltransferases; D006027:Glycosides / Q000096:biosynthesis* / Q000737:chemistry*; D006031:Glycosylation; D007408:Intestinal Absorption; D039823:Iridoids; D008968:Molecular Conformation; D010944:Plants / Q000201:enzymology*; D011794:Quercetin / Q000737:chemistry; D051381:Rats; D012995:Solubility
chemical_list: D001688:Biological Products; D002241:Carbohydrates; D006027:Glycosides; D039823:Iridoids; D002338:Carotenoids; C029036:crocin; D011794:Quercetin; D005964:Glucosyltransferases; D003474:Curcumin