title: Malonylation is a key reaction in the metabolism of xenobiotic phenolic glucosides in Arabidopsis and tobacco.
abstract: Tobacco cells (Nicotiana tabacum L.) accumulate harmful naphthols in the form of malonylated glucosides (Taguchi et al., 2005). Here, we showed that the malonylation of glucosides is a system to metabolize xenobiotics and is common to higher plants. Moreover, some plantlets including Arabidopsis thaliana excreted some of the incorporated naphthols into the culture media as their glucosides. In order to analyze the function of malonylation in the metabolism of these xenobiotics, we identified a malonyltransferase gene (At5g39050) responsible for the malonylation of these compounds in A. thaliana. The recombinant enzyme had malonyltransferase activity toward several phenolic glucosides including naphthol glucosides. A knockout mutant of At5g39050 (pmat1) exposed to naphthols accumulated only a few malonylglucosides in the cell, and released larger amounts of simple glucosides into the culture medium. In contrast, forced expression of At5g39050 in the pmat1 mutant resulted in increased malonylglucoside accumulation and decreased glucoside excretion to the media. The results provided clear evidence of whether the release of glucosides or the storage of malonylglucosides was determined by the At5g39050 expression level. A similar event in naphthol metabolism was observed in the tobacco mutant with a suppressed malonyltransferase gene (NtMaT1). These results suggested that malonylation could be a key reaction to separate the way of xenobiotics disposition, that is, release from cell surface or storage in vacuoles.
authors.affiliation: Division of Applied Biology, Faculty of Textile Science and Technology, Shinshu University, 3-15-1 Tokida, Ueda 386-8567, Japan. gtagtag@shinshu-u.ac.jp
authors.forename: Goro
authors.initials: G
authors.lastname: Taguchi
authors.forename: Takahisa
authors.initials: T
authors.lastname: Ubukata
authors.forename: Hatsumi
authors.initials: H
authors.lastname: Nozue
authors.forename: Yuki
authors.initials: Y
authors.lastname: Kobayashi
authors.forename: Maki
authors.initials: M
authors.lastname: Takahi
authors.forename: Hirobumi
authors.initials: H
authors.lastname: Yamamoto
authors.forename: Nobuaki
authors.initials: N
authors.lastname: Hayashida
mesh_terms: D017360:Arabidopsis / Q000378:metabolism*; D029681:Arabidopsis Proteins / Q000145:classification / Q000235:genetics; D005960:Glucosides / Q000378:metabolism*; D008969:Molecular Sequence Data; D009284:Naphthols / Q000378:metabolism; D010636:Phenols / Q000378:metabolism*; D010802:Phylogeny; D010940:Plant Proteins / Q000145:classification / Q000235:genetics; D030821:Plants, Genetically Modified / Q000235:genetics / Q000378:metabolism; D014026:Nicotiana / Q000378:metabolism*; D015262:Xenobiotics / Q000378:metabolism*
chemical_list: D029681:Arabidopsis Proteins; D005960:Glucosides; D009284:Naphthols; D010636:Phenols; D010940:Plant Proteins; D015262:Xenobiotics