P-91 植物の二次代謝機能を利用した超天然型有用配糖体の創出(ポスター発表の部)

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Higher plants accumulate a wide range of glycosides as secondary metabolites, and are capable of conjugating sugar residues not only to endogenous metabolic intermediates but also to xenobiotics. The glycosylation reactions are catalyzed by plant UDP-glycosyltransferases, which transfer sugar moieties from UDP-activated sugar donors to low molecular weight acceptors. Glycosyl conjugation of lipophilic small molecules is an efficient tool to enhance water solubility, to improve stability and thereby to increase bioavailability and modify biological activity. Curcumin is a yellow pigment of turmeric (dried rhizome of Curcuma longa, Zingiberaceae). Although curcumin is an interesting compound as a novel medicine or a lead compound, its low water solubility limits further pharmacological exploration and practical application. Here we investigate that Catharanthus roseus cell suspension cultures are capable of converting exogenously supplied curcumin to a series of unnatural glucosides. The water solubility of curcumin glucosides is increased up to 20-million-fold compared with that of the aglycone, indicating that glucosylation of hydrophobic compounds is a powerful method to enhance water solubility. Furthermore, we describe the isolation of five cDNAs (Catharanthus roseus UDP-glucose glucosyltransferase CaUGT1〜5) from a cDNA library of cultured C. roseus cells, using a homology-based PCR cloning strategy directed at the conserved domain, the Plant Secondary Product Glycosyltransferase (PSPG) motif. Functional expression of the gene products in Escherichia coli demonstrated that CaUGT2 converts curcumin to curcumin monoglucoside and diglucoside, whereas CaUGT3 converts curcumin monoglucoside to curcumin monogentiobioside, gentiotrioside, and gentiotetroside.
天然有機化合物討論会の論文
2008-09-01

P-91 植物の二次代謝機能を利用した超天然型有用配糖体の創出(ポスター発表の部)

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