Novel human lens metabolites from normal and cataractous human lenses

被引:29
作者
Mizdrak, Jasminka
Hains, Peter G.
Kalinowski, Danuta
Truscott, Roger J. W.
Davies, Michael J.
Jamie, Joanne F. [1 ]
机构
[1] Macquarie Univ, Dept Chem & Biomol Sci, Sydney, NSW 2109, Australia
[2] Save Sight Inst, Sydney, NSW 2001, Australia
[3] Heart Res Inst, Sydney, NSW 2050, Australia
[4] Univ Sydney, Fac Med, Sydney, NSW 2006, Australia
基金
英国医学研究理事会; 澳大利亚研究理事会;
关键词
D O I
10.1016/j.tet.2007.03.133
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-(2-Aminophenyl)-4-oxobutanoic acid, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine have been identified as novel metabolites in normal and cataractous human lenses following total synthesis and comparison with authentic human lens samples. Their structures are consistent with those derived from the major human lens UV filters kynurenine and 3-hydroxykynurenine, and it is proposed that these compounds also play a role as UV filters. These metabolites were isolated in pmol/mg levels (dry mass) in lenses. 4-(2-Amino-3-hydroxyphenyl)-4-oxobutanoic acid and glutathionyl-kynurenine were found to be unstable at physiological pH. Other potential metabolites, glutathionyl-3-hydroxykynurenine, kynurenine yellow and 3-hydroxykynurenine yellow, were not detected in either normal or cataractous lenses. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4990 / 4999
页数:10
相关论文
共 43 条
[1]   Elucidation of a novel polypeptide cross-link involving 3-hydroxykynurenine [J].
Aquilina, JA ;
Carver, JA ;
Truscott, RJW .
BIOCHEMISTRY, 1999, 38 (35) :11455-11464
[2]   Identifying sites of attachment of UV filters to proteins in older human lenses [J].
Aquilina, JA ;
Truscott, RJW .
BIOCHIMICA ET BIOPHYSICA ACTA-PROTEIN STRUCTURE AND MOLECULAR ENZYMOLOGY, 2002, 1596 (01) :6-15
[3]   GASTRIC ANTI-SECRETORY, ANTI-ULCER AND CYTOPROTECTIVE PROPERTIES OF SUBSTITUTED (E)-4-PHENYL- AND HETEROARYL-4-OXO-2-BUTENOIC ACIDS [J].
BIANCHI, M ;
BUTTI, A ;
CHRISTIDIS, Y ;
PERRONNET, J ;
BARZAGHI, F ;
CESANA, R ;
NENCIONI, A .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1988, 23 (01) :45-52
[4]   OXIDATION OF 3-HYDROXYKYNURENINE - AN EPR INVESTIGATION [J].
BOLOGNESE, A ;
BONOMO, RP ;
CHILLEMI, R ;
SCIUTO, S .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (07) :2207-2208
[5]   OXIDATION OF 3-HYDROXYKYNURENINE - A REEXAMINATION [J].
BOLOGNESE, A ;
LIBERATORE, R ;
RIENTE, G ;
SCHERILLO, G .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (04) :1247-1250
[6]  
Bova LM, 2001, INVEST OPHTH VIS SCI, V42, P200
[7]  
BOVA LM, 1999, INVEST OPHTH VIS SCI, V40, P3227
[8]   A NEW L-ALPHA-AMINO ACID FROM LEPIDOPTERA [J].
BROWN, KS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (18) :4202-&
[9]  
BUTENANDT A, 1954, LIEBIGS ANN CHEM, V588, P106
[10]   SYNTHESEN DES 3-HYDROXY-KYNURENINS [J].
BUTENANDT, A ;
HALLMANN, G ;
BECKMANN, R .
CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (06) :1120-1124