1.0 2011-09-21 01:53:25 UTC 2015-07-21 06:59:41 UTC FDB029293 Xanthurenate-8-O-beta-D-glucoside Xanthurenic acid 8-O-beta-D-glucoside, a fluorescent metabolite, has been isolated from heads of eye-color mutants of Drosophila melanogaster. Only a few mutations cause it to accumulate, viz. cardinal (cd), dark red brown (drb), Henna-recessive (Hnr), purple (pr), Punch2 (Pu2), Punch-Grape (PuGr), and scarlet (st). After purification by ion-exchange chromatography, the spectroscopic, chemical, and enzymatic analyses revealed that it is a novel quinoline derivative. Feeding experiments suggest that this glucoside is synthesized from 3-hydroxykynurenine and that free xanthurenic acid is not a precursor. The results from the analysis for its occurrence in double mutants, together with the fact that xanthurenic acid 8-glucoside share the same precursor as xanthurenic acid and xanthommatin, suggest that xanthurenic acid 8-glucoside formation is closely related to the regulation of the last step in the biosynthesis of xanthommatin.[PMID: 3922986] Xanthurenic acid 8-glucoside is a side metabolite of the tryptophan-xanthommatin pathway in Drosophila. From 3-hydroxykynurenine, two biosynthetic pathways can be envisaged, one via xanthurenic acid, and another via 3-O-glucoside of 3-hydroxykynurenine. Evidence is presented to show that the synthesis takes place via xanthurenic acid. (a) the Drosophila melanogaster vermilion purple mutant (unable to synthesize 3-hydroxykynurenine) synthesizes xanthurenic acid 8-glucoside when fed with xanthurenic acid; and (b) the activities required for its synthesis via xanthurenic acid have been found (3-hydroxykynurenine transaminase and xanthurenic acid:UDP-glucosyltransferase). This is the first time that a UDP-glucosyltransferase activity that utilizes xanthurenic acid has been demonstrated. The enzyme in crude extracts from Drosophila sordidula shows the following characteristics. (a) It has optimal activity at 35 degrees C at pH 7.1 (in buffer Tris-HCl), and in the presence of a divalent cation (Mg2+ or Mn2+); (b) the activity is inhibited by xanthurenic acid (above 1.5 mM), UDP, D-gluconic acid 1,5-lactone, and Triton X-100; (c) it is localized in both the microsomal and the soluble fractions; (d) the specific activity is two times higher in heads than in bodies; and (e) the activity is enhanced in flies fed with phenobarbital. [HMDB] 4,8-dihydroxy-8-O-beta-D-glucoside-quinaldic acid anion 4,8-dihydroxy-8-O-beta-D-glucoside-quinoline-2-carboxylic acid anion 4,8-dihydroxy-8-O-beta-delta-glucoside-quinaldic acid anion 4,8-dihydroxy-8-O-beta-delta-glucoside-quinoline-2-carboxylic acid anion 4,8-dihydroxyquinaldic acid 8-O-beta-D-glucoside 4,8-dihydroxyquinaldic acid 8-O-beta-delta-glucoside 4,8-dihydroxyquinoline-2-carboxylic acid 8-O-beta-D-glucoside 4,8-dihydroxyquinoline-2-carboxylic acid 8-O-beta-delta-glucoside Xan8Glc xanthurenic acid 8-O-beta-D-glucoside xanthurenic acid 8-O-beta-delta-glucoside C16H17NO9 367.3075 367.090331147 4-hydroxy-8-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}quinoline-2-carboxylic acid 4-hydroxy-8-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}quinoline-2-carboxylic acid 97451-32-6 OC[C@H]1O[C@@H](OC2=C3N=C(C=C(O)C3=CC=C2)C(O)=O)[C@@H](O)[C@@H](O)[C@H]1O InChI=1S/C16H17NO9/c18-5-10-12(20)13(21)14(22)16(26-10)25-9-3-1-2-6-8(19)4-7(15(23)24)17-11(6)9/h1-4,10,12-14,16,18,20-22H,5H2,(H,17,19)(H,23,24)/t10-,12+,13+,14+,16-/m1/s1 MYFHOUJDPFBJLH-XGJKELJWSA-N belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Phenolic glycosides Organic compounds Organic oxygen compounds Organooxygen compounds Carbohydrates and carbohydrate conjugates Aromatic heteropolycyclic compounds Acetals Azacyclic compounds Benzenoids Carboxylic acids Heteroaromatic compounds Hexoses Hydrocarbon derivatives Hydroquinolines Hydroquinolones Monocarboxylic acids and derivatives O-glycosyl compounds Organic oxides Organonitrogen compounds Organopnictogen compounds Oxacyclic compounds Oxanes Polyols Primary alcohols Pyridinecarboxylic acids Quinoline carboxylic acids Secondary alcohols Vinylogous amides Acetal Alcohol Aromatic heteropolycyclic compound Azacycle Benzenoid Carboxylic acid Carboxylic acid derivative Dihydroquinoline Dihydroquinolone Heteroaromatic compound Hexose monosaccharide Hydrocarbon derivative Monocarboxylic acid or derivatives Monosaccharide O-glycosyl compound Organic nitrogen compound Organic oxide Organoheterocyclic compound Organonitrogen compound Organopnictogen compound Oxacycle Oxane Phenolic glycoside Polyol Primary alcohol Pyridine Pyridine carboxylic acid Pyridine carboxylic acid or derivatives Quinoline Quinoline-2-carboxylic acid Secondary alcohol Vinylogous amide Solid logp -0.41 ALOGPS logs -1.86 ALOGPS solubility 5.10e+00 g/l ALOGPS logp -0.7 ChemAxon pka_strongest_acidic 0.87 ChemAxon pka_strongest_basic 4.09 ChemAxon iupac 4-hydroxy-8-{[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}quinoline-2-carboxylic acid ChemAxon average_mass 367.3075 ChemAxon mono_mass 367.090331147 ChemAxon smiles OC[C@H]1O[C@@H](OC2=C3N=C(C=C(O)C3=CC=C2)C(O)=O)[C@@H](O)[C@@H](O)[C@H]1O ChemAxon formula C16H17NO9 ChemAxon inchi InChI=1S/C16H17NO9/c18-5-10-12(20)13(21)14(22)16(26-10)25-9-3-1-2-6-8(19)4-7(15(23)24)17-11(6)9/h1-4,10,12-14,16,18,20-22H,5H2,(H,17,19)(H,23,24)/t10-,12+,13+,14+,16-/m1/s1 ChemAxon inchikey MYFHOUJDPFBJLH-XGJKELJWSA-N ChemAxon polar_surface_area 169.8 ChemAxon refractivity 82.97 ChemAxon polarizability 34 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 10 ChemAxon donor_count 6 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 10189 Specdb::CMs 40057 Specdb::CMs 135649 Specdb::CMs 143383 Specdb::MsMs 327631 Specdb::MsMs 327632 Specdb::MsMs 327633 Specdb::MsMs 912754 Specdb::MsMs 912755 Specdb::MsMs 912756 Specdb::MsMs 2283100 Specdb::MsMs 2283101 Specdb::MsMs 2283102 Specdb::MsMs 3085225 Specdb::MsMs 3085226 Specdb::MsMs 3085227 Specdb::NmrOneD 98778 Specdb::NmrOneD 98779 Specdb::NmrOneD 98780 Specdb::NmrOneD 98781 Specdb::NmrOneD 98782 Specdb::NmrOneD 98783 Specdb::NmrOneD 98784 Specdb::NmrOneD 98785 Specdb::NmrOneD 98786 Specdb::NmrOneD 98787 Specdb::NmrOneD 98788 Specdb::NmrOneD 98789 Specdb::NmrOneD 98790 Specdb::NmrOneD 98791 Specdb::NmrOneD 98792 Specdb::NmrOneD 98793 Specdb::NmrOneD 98794 Specdb::NmrOneD 98795 Specdb::NmrOneD 98796 Specdb::NmrOneD 98797 HMDB13118 #<Reference:0x000055ce30e6af60>