Detection, quantification, and total synthesis of novel 3-hydroxykynurenine glucoside-derived metabolites present in human lenses

Research output: Contribution to journalJournal articleResearchpeer-review

Standard

Detection, quantification, and total synthesis of novel 3-hydroxykynurenine glucoside-derived metabolites present in human lenses. / Gad, Nicholas A; Mizdrak, Jasminka; Pattison, David I; Davies, Michael Jonathan; Truscott, Roger J W; Jamie, Joanne F.

In: Investigative Ophthalmology & Visual Science, Vol. 55, No. 2, 02.2014, p. 849-55.

Research output: Contribution to journalJournal articleResearchpeer-review

Harvard

Gad, NA, Mizdrak, J, Pattison, DI, Davies, MJ, Truscott, RJW & Jamie, JF 2014, 'Detection, quantification, and total synthesis of novel 3-hydroxykynurenine glucoside-derived metabolites present in human lenses', Investigative Ophthalmology & Visual Science, vol. 55, no. 2, pp. 849-55. https://doi.org/10.1167/iovs.13-13464

APA

Gad, N. A., Mizdrak, J., Pattison, D. I., Davies, M. J., Truscott, R. J. W., & Jamie, J. F. (2014). Detection, quantification, and total synthesis of novel 3-hydroxykynurenine glucoside-derived metabolites present in human lenses. Investigative Ophthalmology & Visual Science, 55(2), 849-55. https://doi.org/10.1167/iovs.13-13464

Vancouver

Gad NA, Mizdrak J, Pattison DI, Davies MJ, Truscott RJW, Jamie JF. Detection, quantification, and total synthesis of novel 3-hydroxykynurenine glucoside-derived metabolites present in human lenses. Investigative Ophthalmology & Visual Science. 2014 Feb;55(2):849-55. https://doi.org/10.1167/iovs.13-13464

Author

Gad, Nicholas A ; Mizdrak, Jasminka ; Pattison, David I ; Davies, Michael Jonathan ; Truscott, Roger J W ; Jamie, Joanne F. / Detection, quantification, and total synthesis of novel 3-hydroxykynurenine glucoside-derived metabolites present in human lenses. In: Investigative Ophthalmology & Visual Science. 2014 ; Vol. 55, No. 2. pp. 849-55.

Bibtex

@article{3c3caf3cbc384e7c8eefb455050858e5,
title = "Detection, quantification, and total synthesis of novel 3-hydroxykynurenine glucoside-derived metabolites present in human lenses",
abstract = "PURPOSE: 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.METHODS: 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.RESULTS: 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.CONCLUSIONS: Three novel 3OHKG-derived metabolites have been detected in extracts from human lenses.",
keywords = "Adolescent, Adult, Aged, Aged, 80 and over, Cataract, Chromatography, High Pressure Liquid, Glucosides, Humans, Lens, Crystalline, Magnetic Resonance Spectroscopy, Middle Aged, Phenylbutyrates, Spectrophotometry, Ultraviolet, Tandem Mass Spectrometry, Young Adult",
author = "Gad, {Nicholas A} and Jasminka Mizdrak and Pattison, {David I} and Davies, {Michael Jonathan} and Truscott, {Roger J W} and Jamie, {Joanne F}",
year = "2014",
month = feb,
doi = "10.1167/iovs.13-13464",
language = "English",
volume = "55",
pages = "849--55",
journal = "Investigative Ophthalmology & Visual Science",
issn = "0146-0404",
publisher = "Association for Research in Vision and Ophthalmology",
number = "2",

}

RIS

TY - JOUR

T1 - Detection, quantification, and total synthesis of novel 3-hydroxykynurenine glucoside-derived metabolites present in human lenses

AU - Gad, Nicholas A

AU - Mizdrak, Jasminka

AU - Pattison, David I

AU - Davies, Michael Jonathan

AU - Truscott, Roger J W

AU - Jamie, Joanne F

PY - 2014/2

Y1 - 2014/2

N2 - PURPOSE: 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.METHODS: 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.RESULTS: 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.CONCLUSIONS: Three novel 3OHKG-derived metabolites have been detected in extracts from human lenses.

AB - PURPOSE: 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.METHODS: 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.RESULTS: 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.CONCLUSIONS: Three novel 3OHKG-derived metabolites have been detected in extracts from human lenses.

KW - Adolescent

KW - Adult

KW - Aged

KW - Aged, 80 and over

KW - Cataract

KW - Chromatography, High Pressure Liquid

KW - Glucosides

KW - Humans

KW - Lens, Crystalline

KW - Magnetic Resonance Spectroscopy

KW - Middle Aged

KW - Phenylbutyrates

KW - Spectrophotometry, Ultraviolet

KW - Tandem Mass Spectrometry

KW - Young Adult

U2 - 10.1167/iovs.13-13464

DO - 10.1167/iovs.13-13464

M3 - Journal article

C2 - 24408982

VL - 55

SP - 849

EP - 855

JO - Investigative Ophthalmology & Visual Science

JF - Investigative Ophthalmology & Visual Science

SN - 0146-0404

IS - 2

ER -

ID: 128973954