| UV filter compounds in human lenses: the origin of 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-beta-D-glucoside. | |
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MedLine Citation:
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PMID: 10586948 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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PURPOSE: To investigate UV filter synthesis in the human lens, in particular the biosynthetic origin of the second most abundant UV filter compound, 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-beta-D-glucoside. METHODS: Human lenses were analyzed by high-performance liquid chromatography (HPLC) after separate incubation with 3H-tryptophan (3H-Trp), beta-benzoylacrylic acid, D,L-alpha-amino-beta-benzoylpropionic acid, or D,L-3-hydroxykynurenine O-beta-D-glucoside. The effect of pH on the model compound D,L-alpha-amino-beta-benzoylpropionic acid and D,L-3-hydroxykynurenine O-beta-D-glucoside was also investigated. RESULTS: UV filters were not detected in fetal lenses, despite a 5-month postnatal lens displaying measurable levels of UV filters. In adults no radiolabel was incorporated into 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-beta-D-glucoside after 3H-Trp incubations. Beta-benzoylacrylic acid was readily reduced in lenses. D,L-alpha-amino-beta-benzoylpropionic acid and D,L-3-hydroxykynurenine O-beta-D-glucoside slowly deaminated at physiological pH and were converted to beta-benzoylpropionic acid and 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-beta-D-glucoside, respectively, after lens incubations. CONCLUSIONS: UV filter biosynthesis appears to be activated at or near birth. Compounds containing the kynurenine side chain slowly deaminate, and in the lens, the newly formed double bond is rapidly reduced. These findings suggest that 4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-beta-D-glucoside is derived from L-3-hydroxykynurenine O-beta-D-glucoside through this deamination-reduction process. The slowness of the deamination presumably accounts for the absence of incorporation of radiolabel from 3H-Trp into 4(2-amino-3-hydroxyphenyl)4-oxobutanoic acid O-beta-D-glucoside. |
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Authors:
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L M Bova; A M Wood; J F Jamie; R J Truscott |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Investigative ophthalmology & visual science Volume: 40 ISSN: 0146-0404 ISO Abbreviation: Invest. Ophthalmol. Vis. Sci. Publication Date: 1999 Dec |
Date Detail:
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Created Date: 1999-12-09 Completed Date: 1999-12-09 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 7703701 Medline TA: Invest Ophthalmol Vis Sci Country: UNITED STATES |
Other Details:
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Languages: eng Pagination: 3237-44 Citation Subset: IM |
Affiliation:
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Australian Cataract Research Foundation, Department of Chemistry, University of Wollongong, New South Wales. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Acrylates
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metabolism Adult Aging / physiology Benzoates / metabolism Chromatography, High Pressure Liquid Deamination Fetus Glucosides / metabolism* Humans Hydrogen-Ion Concentration Infant Kynurenine / analogs & derivatives*, metabolism Lens, Crystalline / metabolism* Middle Aged Phenylbutyrates / metabolism* Propionates / metabolism Tryptophan / metabolism Ultraviolet Rays |
| Chemical | |
Reg. No./Substance:
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0/Acrylates; 0/Benzoates; 0/Glucosides; 0/Phenylbutyrates; 0/Propionates; 0/amino-beta-benzoylpropionic acid; 0/benzoylacrylic acid; 0/benzoylpropionic acid; 156913-43-8/4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid O-glucoside; 343-65-7/Kynurenine; 484-78-6/3-hydroxykynurenine; 73-22-3/Tryptophan |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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