Abstract
The fluorescent products formed on reaction of 12-oxo-cis-9-octadecenoic acid (12-keto-oleic acid) with about 20 different amino acids, polylysine and bovine serum albumin (BSA) were studied. Besides glycine, only the basic amino acids histidine, lysine and arginine gave products with strong fluorescence. N-Acetylation of amino acids greatly reduced the fluorescence of their reaction products. The formation of fluorescent products was inhibited strongly by SH-amino acids such as N-acetyl-cysteine and glutathione. Polyacrylamide gel electrophoresis showed that BSA treated with 12-keto-oleic acid was more acidic than untreated or ricinoleic acid-treated BSA, indicating that basic amino acid residues in BSA were modified by reaction with the keto fatty acid. None of the structural analogs of 12-keto-oleic acid tested–12-oxo-trans-10-octadecenoic acid, 12-oxo-octadecanoic acid, 12-hydroxy-cis-9-octadecenoic acid (ricinoleic acid),cis-9-octadecenoic acid (oleic acid) and linoleic acid—reacted with glycine to give a fluorescent product. The fluorescent products formed on reaction of 12-keto-oleic acid methyl ester with benzyl amine and glycine methyl ester were shown to be 8-(N-substituted-4,5-dihydro-4-oxo-5-hexyl-5-hydroxy-2-pyrrolyl) octanoic acid methyl esters. The fluorescence properties of these compounds were attributed to the chromophobic system NC=CC=O which contains 6π electrons. This investigation contributes to insight of the mechanism of formation of fluorescent pigments, probably by a similar reaction of other compounds of the β,γ-unsaturated carbonyl type.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Tappel, A.L. (1973) Fed. Proc. 32, 1870–1974.
Shimasaki, H., Ueta, N., and Privett, O.S. (1980) Lipids 15, 236–241.
Csallany, A.S., and Ayaz, K.L. (1976) Lipids 11, 412–417.
Elleder, M. (1981) in Age Pigments (Sohla, R.S., ed.) pp. 204–203, Elsevier/North-Holland, Amsterdam.
Wolman, M. (1981) in Age Pigments (Sohal, R.S., ed.) pp. 265–275, Elsevier/North-Holland, Amsterdam.
Eldred, G.E., Miller, G.V., and Stark, W.S. (1982) Science 216, 757–759.
Dror, Y., Budowski, P., Bubis, J.J., Sandbank, U., and Wolman, M. (1976) Prog. Neuropathol. 3, 343–357.
Desai, I.D., Fletcher, B.L., and Tappel, A.L. (1975) Lipids 10, 307–309.
Bieri, J.G., Tolliver, T.J., Robinson, W.G. Jr., and Kuwabara, T. (1980) Lipids 15, 10–13.
Manwaring, J.D., and Csallany, A.S. (1981) J. Nutr. 111, 2172–2179.
Csallany, A.S., Ayaz, K.L., and Menken, B.Z. (1984) Lipids 19, 911–915.
Nielsen, H. (1981) Lipids 16, 215–222.
Shimasaki, H., Ueta, N., and Privett, O.S. (1982) Lipids 17, 878–883.
Shimasaki, H., Ueta, N., Mowri, H., and Inoue, K. (1984) Biochim. Biophys. Acta 792, 123–129.
Chio, K.S., and Tappel, A.L. (1969) Biochemistry 8, 2821–2827.
Kokatnur, M.G., Okui, S., Kummerow, F.A., and Scott, H.M. (1960) Proc. Soc. Exp. Biol. Med. 104, 170–171.
Budowski, P., Bartov, I., Dror, Y., and Frankel, E.N. (1979) Lipids 14, 768–772.
Sato, M., and Uchiyama, M. (1972) Chem. Pharm. Bull. 20, 815–822.
Sato, M., and Ichiyama, M. (1971) Chem. Pharm. Bull. 19, 1118–1122.
Sato, M., Fukuzawa, K., and Uchiyama, M. (1972) J. Food Hyg. Soc. Japan 13, 137–140.
Fukuzawa, K., and Sato, M. (1975) J. Nutr. Sci. Vitaminol. 21, 79–88.
Peers, K.E., Coxon, D.T., and Chan, H.W.S. (1984) Lipids 19, 307–313.
Paulson, D.R., Tang, Y.N.F., and Sloan, R.B. (1973) J. Org. Chem. 38, 3967–3968.
Frankel, E.N., Neff, W.E., and Selke, E. (1984) Lipids 19, 790–800.
Nicols, J., and Schipper, E. (1958) J. Am. Chem. Soc. 80, 5705–5710.
Esterbauer, H., Cheeseman, K.H., Dianzani, M.U., Poli, G., and Slater, T.F. (1982) Biochem. J. 208, 129–140.
Yoden, K., Matsuzaki, R., Iio, T., and Tabata, T. (1982) Yakugaku Zasshi 102, 768–773.
Author information
Authors and Affiliations
About this article
Cite this article
Fukuzawa, K., Kishikawa, K., Tokumura, A. et al. Fluorescent pigments by covalent binding of lipid peroxidation by-products to protein and amino acids. Lipids 20, 854–861 (1985). https://doi.org/10.1007/BF02534768
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02534768