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(12) Patent Application Publication (10) Pub. No.: US 2010/0323402 A1 Ono Et Al US 201003234O2A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0323402 A1 Ono et al. (43) Pub. Date: Dec. 23, 2010 (54) UDP-GLUCURONYL TRANSFERASE AND Publication Classification POLYNUCLEOTDE ENCODING THE SAME (51) Int. Cl. CI2P 9/60 (2006.01) (75) Inventors: Eiichiro Ono, Osaka (JP); Akio C7H 2L/04 (2006.01) Noguchi, Osaka (JP); Yuko Fukui, C7H 2L/00 (2006.01) Osaka (JP); Masako Mizutani, CI2N 9/10 (2006.01) Osaka (JP) CI2N 15/63 (2006.01) CI2N I/2 (2006.01) Correspondence Address: (52) U.S. Cl. ......... 435/75:536/23.2:536/23.1; 435/193; GREENBLUM & BERNSTEIN, P.L.C. 1950 ROLAND CLARKE PLACE 435/320.1; 435/252.33 RESTON, VA 20191 (US) (57) ABSTRACT The present invention provides a novel UDP-glucuronosyl (73) Assignee: SUNTORY HOLDINGS transferase and a polynucleotide encoding the same (for LIMITED, Osaka (JP) example, a polynucleotide comprising a polynucleotide con sisting of one nucleotide sequence selected from the group (21) Appl. No.: 12/678,161 consisting of the nucleotide sequence at positions 1 to 1359 in the nucleotide sequence represented by SEQ ID NO: 4, the (22) PCT Fled: Sep. 29, 2008 nucleotide sequence at positions 1 to 1365 in the nucleotide PCT NO.: PCT/UP2008/O67613 sequence represented by SEQ ID NO: 10, the nucleotide (86) sequence at positions 1 to 1371 in the nucleotide sequence S371 (c)(1), represented by SEQID NO: 12, and the nucleotide sequence (2), (4) Date: May 12, 2010 at positions 1 to 1371 in the nucleotide sequence represented by SEQ ID NO: 22; or a polynucleotide comprising a poly (30) Foreign Application Priority Data nucleotide encoding a protein having one amino acid sequence selected from the group consisting of SEQID NOS: Oct. 12, 2007 (JP) ................................. 2007-267050 5, 11, 13 and 23), etc. This provides a novel UDP-glucurono Mar 17, 2008 (JP) ................................. 2008-067.185 syltransferase with a broad substrate specificity. Patent Application Publication Dec. 23, 2010 Sheet 1 of 8 US 2010/0323402 A1 Formatted Alignments AmUGTogi Oaa 450 SEUGTaa 448 445 434 Patent Application Publication Dec. 23, 2010 Sheet 2 of 8 US 2010/0323402 A1 Fig. 2 BaiCalein a SCutellarein a Apigenin a Luteolin TriCetin DiOSmetin 3.33. Chrysoeriol is Vitexin ISOVitexin Orientin Kaempferol QuerCetin Myricetins Naringenin AureuSidin Genistein DaidZein Formononetin Catechin Epigallocatechin gallate ESCuletin Coniferyl alcohol ReSVeratrol SC1 SC2 Relative activity (%) Patent Application Publication Dec. 23, 2010 Sheet 3 of 8 US 2010/0323402 A1 Fig. 3 BaiCalein SCutellarein Apigenin Luteolin TriCetin DiOSmetin Chrysoeriol Vitexin SOVitexin Orientin Kaempferol QuerCetin Naringenin AureuSidin Genistein Daidzein Formononetin Catechin Epigallocatechin gallate ESCulletin Coniferyl alcohol ReSVeratrol SC 1 SC2 EC2 O 20 40 60 80 100 120 Relative activity (%) Patent Application Publication Dec. 23, 2010 Sheet 4 of 8 US 2010/0323402 A1 Baicalein SCutellarein Apigenin Luteolin TriCetin DiOSmetin Chrysoeriol Vitexin ISOVitexin Orientin Kaempferol QuerCetin Naringenin Aureusidin Genistein Daidzein Formononetin Catechin Epigallocatechin gallate ESCulletin Coniferyl alcohol ReSVeratrol SC1 SC2 EC2 O 20 40 60 80 100 120 Relative activity (%) Patent Application Publication Dec. 23, 2010 Sheet 5 of 8 US 2010/0323402 A1 Fig. 5 BaiCalein SCutellarein Apigenin Luteolin TriCetin DioSmetin Chrysoeriol Vitexin SOVitexin Orientin Kaempferol QuerCetin Naringenin AureuSidin Genistein DaidZein Formononetin Catechin Epigallocatechin gallate ESCulletin Caffeic acid Resveratrol SC1 SC2 EC2 O 20 40 60 80 100 120 Relative activity (%) Patent Application Publication Dec. 23, 2010 Sheet 6 of 8 US 2010/0323402 A1 Fig. 6 0.0 2.5 5. O 7.5 10.0 2.5 15.0 min Patent Application Publication Dec. 23, 2010 Sheet 7 of 8 US 2010/0323402 A1 Fig. 7 s 3 & 3 Patent Application Publication Dec. 23, 2010 Sheet 8 of 8 US 2010/0323402 A1 1z'g'''. g as sus or narrarass guns in a na narran sesssssssssssssserraneant ?cosit/ Trainiere S '' i i is is elziz (i. st is a i E use E S35 :: US 2010/0323402 A1 Dec. 23, 2010 UDP-GLUCURONYLTRANSFERASE AND is registered in GenBank (Accession No. AB042277) but its POLYNUCLEOTIDE ENCODING THE SAME function remains unconfirmed. 0008. On the other hand, it is known that flavone 7-glucu FIELD OF THE INVENTION ronides which are more diverse than skullcap or “wogon' are accumulated in Perilla frutescens a red-leaf variety with a 0001. The present invention relates to a UDP-glucurono dietary experience (Literature 7: Yamazaki, M. et al. Phy Syltransferase, a polynucleotide encoding the same, a vector tochemistry 62,987-998. 2003). containing the same, a transformant, and so on. Literatures: BACKGROUND OF THE INVENTION 0009. 1. Day, A. J. et al., Free Radic. Res., 35,941-952, 0002 Polyphenolic plant secondary metabolites including 2001 flavonoids and lignans with a rich dietary experience have (0010 2. Moon, J. H. et al., Free Radical Biology & Medi attracted attention as functional materials over the years due cine, 30, 1274-1285, 2001 to their functional properties represented by their antioxida 0011 3. O'Leary, K. A. et al., Biochemical Pharmacology, tive activities, and are already commercially available as 65, 479–491, 2003 health foods. For example, quercetin (flavonoid), OTPP (fla 0012 4. Vander Woude, H. et al., Chem. Res. Toxicol., 17, vonoid), Sesamin (lignan), etc. are representative materials 1520-1530, 2004 for health foods. 0013 5. Gao, Z. et al., Biochemica et Biophysica Acta, 0003. The biosynthetic pathway of flavonoids in plant 1472, 643-650, 1999 cells has been studied since old times. Biosynthetic enzymes (0014) 6. Nagashima S. et al., Phytochemistry, 53,533-538, that catalyze the metabolic pathway and genes encoding the 2OOO. enzymes are isolated, leading to a better understanding of (0015 7. Yamazaki, M. et al., Phytochemistry, 62.987-998, their molecular mechanisms. 2003 0004. On the other hand, knowledge is insufficient on how the plant secondary metabolites would be metabolized to DISCLOSURE OF THE INVENTION exhibit their functions, after their in vivo uptake. 0005. It is known that glycosylation of plant secondary Problems To Be Solved by the Invention metabolites is generally catalyzed by an enzyme belonging to 0016 Under these circumstances, it has been desired to the superfamily called UDP-glycosyltransferase (UGT), irre identify a novel UDP-glucuronosyltransferase having a spective of types of Sugars (glucose, rhamnose, glucuronic broader Substrate specificity and a gene encoding the same. acid, galactose, etc.). Further in the studies of Sesamin, the secondary metabolites are shown to be present in vivo as Means of Solving the Problem glucuronides via catechol metabolites. It is thus considered that the glucuronides would play a part in developing the in 0017. The present invention has been made in view of the Vivo functions of plant secondary metabolites. foregoing circumstances and provides the following UDP 0006. It is confirmed that four monoglucuronides are glucuronosyltransferases and polynucleotides encoding the present as the metabolites of quercetin in mammals (Q-3- same, as well as vectors bearing the same, transformants, and GlcA, Q-7-GlcA, Q-3'-GlcA and Q-4'-GlcA) (Literature 1: SO. O. Day, AJ et al. Free Radic. Res. 35,941-952, 2001, Literature 0018 (1) A polynucleotide of any one of (a) through (f) 2: Moon, J. H. et al. Free Radical Biology & Medicine 30, below: 1274-1285, 2001, Literature 3: O'Leary, K. A. et al. Bio 0019 (a) a polynucleotide comprising a polynucleotide chemical Pharmacology 65, 479–491, 2003, and Literature 4: consisting of one nucleotide sequence selected from the van der Woude, H. et al. Chem. Res. Toxicol. 17, 1520-1530, group consisting of the nucleotide sequence at positions 1 to 2004); in order to understand these functions in vivo, it is 1359 in the nucleotide sequence represented by SEQID NO: necessary to obtain a sufficient amount of compounds to 4, the nucleotide sequence at positions 1 to 1365 in the nucle examine their activities. However, any appropriate UDP-glu otide sequence represented by SEQID NO: 10, the nucleotide curonosyltransferase showing a broad Substrate specificity is sequence at positions 1 to 1371 in the nucleotide sequence unknown so far, and it was actually impossible to chemically represented by SEQID NO: 12, and the nucleotide sequence synthesize a binding site-specific reaction product. at positions 1 to 1371 in the nucleotide sequence represented 0007. The radix of Labiatae Scutellaria baicalensis is by SEQID NO: 22: called skullcap or “wogon' in Japanese, and it is known that 0020 (b) a polynucleotide comprising a polynucleotide 7-glucuronides of highly antioxidative flavones are accumu encoding a protein having one amino acid sequence selected lated therein. According to the borderline of pharmaceuticals from the group consisting of SEQID NOs: 5, 11, 13 and 23; to non-pharmaceuticals, the radix of Scutellaria baicalensis 0021 (c) a polynucleotide comprising a polynucleotide is classified into the pharmaceuticals (Literature 5: Gao, Z. et encoding a protein consisting of an amino acid sequence with al. Biochimica et Biophysica Acta 1472, 643-650. 1999). To deletion, substitution, insertion and/or addition of 1 to 15 date, Sb7GAT is purified from Labiatae Scutellaria baicallen amino acids in one amino acid sequence selected from the sis as flavone 7-glucuronosyltransferase; this enzyme acts group consisting of SEQID NOs: 5, 11, 13 and 23, and having only on flavones with Substituents such as hydroxyl group at a UDP-glucuronosyltransferase activity; the ortho position of the 7-OH flavones (baicalein, scutella 0022 (d) a polynucleotide comprising a polynucleotide rein, etc.) but does not act on apigenin and luteolin which are encoding a protein having an amino acid sequence having a the major flavones and further not on quercetin which is one homology of at least 80% to one amino acid sequence of flavonols (Literature 6: Nagashima S. et al., Phytochemis selected from the group consisting of SEQID NOs: 5, 11, 13 try 53,533-538, 2000).
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