Melanins and lens pigments: a comparative study.
Based on previous findings that lens pigments and melanins share many physicochemical properties, human lens pigments and natural (hair) and synthetic melanins were submitted to oxidation with permanganate under strong acidic conditions. This procedure has been utilized for the characterization of melanins and results in the well defined products, thiazole-4,5-dicarboxylic acid (TDCA) and pyrrole-2,3,5-tricarboxylic acid (PTCA), which can be quantitated by high performance liquid chromatography (HPLC). PTCA is regarded as a marker of black eumelanins and was therefore a main component of synthetic DOPA-eumelanin and dark hair. Its identity was established by synthesis from 5-hydroxyindole-2-carboxylic acid. TDCA derives from pheomelanins and was therefore an important component of red hair and synthetic GSH-pheomelanin. TDCA was identified by its retention time relative to PTCA. The analysis of a series of cataract digests of increasing pigmentation (type I < type IV < type V) and a purified fraction of lens pigments (DE52 pigment) revealed the presence in these preparations of both PTCA and TDCA. The concentration of TDCA significantly increased with the degree of pigmentation of the digests and reached a maximum in the DE52 pigment. The TDCA/PTCA ratio was high in the lens preparations and comparable to that given by hair pheomelanin. These findings support that pheomelanin is an integral part of lens pigments. By comparing the yields of TDCA in GSH-pheomelanin and in the purified lens pigment, a 9% contribution of pheomelanin to the lens pigment was estimated.
Cuevas
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Department of Ophthalmology, School of Medicine, Univeristy of Puerto Rico, San Juan 00936-5067.
García-Castiñeiras
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D002386:Cataract / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D003998:Dicarboxylic Acids / Q000032:analysis* / Q000378:metabolism; D007908:Lens, Crystalline / Q000737:chemistry* / Q000378:metabolism; D008543:Melanins / Q000032:analysis* / Q000378:metabolism; D010860:Pigments, Biological / Q000032:analysis / Q000378:metabolism; D011758:Pyrroles / Q000032:analysis* / Q000378:metabolism; D013844:Thiazoles / Q000032:analysis* / Q000378:metabolism
D003998:Dicarboxylic Acids; D008543:Melanins; D010860:Pigments, Biological; D011758:Pyrroles; D013844:Thiazoles; C083678:thiazole-4,5-dicarboxylic acid; C071226:pyrrole-2,3,5-tricarboxylic acid