Department of Chemistry and Biomolecular Sciences, Macquarie University, Sydney, New South Wales, Australia.
Invest Ophthalmol Vis Sci. 2014 Feb 10;55(2):849-55. doi: 10.1167/iovs.13-13464.
3-Hydroxykynurenine O-β-D-glucoside (3OHKG) protects the lens from UV damage, and novel related species may act analogously. The aim of this study was to detect, quantify, and elucidate the structures of novel 3-hydroxykynurenine glucoside-derived metabolites present in the human lens.
Compounds were detected and quantified by liquid chromatography with tandem mass spectrometry (LC-MS/MS) in 24 human lenses of different ages, of which 22 were normal and two had cataract. Structures of these were confirmed through total synthesis.
3OHKG concentrations decreased with age in the lens nuclei, whereas the levels of three novel species, 4-(2-amino-3-hydroxyphenyl)-2-hydroxy-4-oxobutanoic acid O-β-D-glucoside (3OHKG-W), 3-hydroxykynurenine O-β-D-glucoside yellow (3OHKG-Y), and 2-amino-3-hydroxyacetophenone O-β-D-glucoside (AHAG), increased, though to different extents. In contrast, the concentrations present in the cortex of the lens remained constant with age.
Three novel 3OHKG-derived metabolites have been detected in extracts from human lenses.
3-羟基犬尿氨酸 O-β-D-葡萄糖苷（3OHKG）可保护晶状体免受紫外线损伤，而新型相关物质可能具有类似作用。本研究旨在检测、定量并阐明人眼晶状体中存在的新型 3-羟基犬尿氨酸葡萄糖苷衍生代谢物的结构。
采用液相色谱-串联质谱（LC-MS/MS）法检测 24 个人眼晶状体中的化合物，这些晶状体来自不同年龄的个体，其中 22 个为正常晶状体，2 个患有白内障。通过全合成法对这些结构进行了确证。
3OHKG 在晶状体核中的浓度随年龄的增长而降低，而三种新型物质的水平则有所增加，分别是 4-(2-氨基-3-羟基苯基）-2-羟基-4-氧代丁酸 O-β-D-葡萄糖苷（3OHKG-W）、3-羟基犬尿氨酸 O-β-D-葡萄糖苷黄（3OHKG-Y）和 2-氨基-3-羟基苯乙酮 O-β-D-葡萄糖苷（AHAG），但增加的程度有所不同。相比之下，晶状体皮质中的物质浓度随年龄的增长保持不变。
在人眼晶状体提取物中检测到了三种新型的 3OHKG 衍生代谢物。
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