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Abstrakty
Alkylresorcinol homologs form stable monomolecular layers at air-water interface. Their interaction with proteins present in the subphase results in an increase of alkylresorcinol molecular packing in the extent dependent upon the protein studied. Strongest effects were observed for proteins with large hydrophobic regions, e.g. glycophorin or serum albumin. Interaction of proteins with alkylresorcinol monolayers is stronger than with phospholipids. A decrease and a shift of intrinsic protein fluorescence upon interaction with the compounds studied support their involvement in alteration of hydrophobic regions. For trypsin, 50% quenching was observed at the alkylresorcinol/trypsin ratio of 0.75. Concomitantly, an apparent inhibition of the enzymatic activity was noted. These results indicate that direct interaction of alkylresorcinols and modulation of enzymatic activities should be recognised as a significant part of the biological effect of these cereal bran components.
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Opis fizyczny
p.241-246,fig.
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autor
- University of Wroclaw, S.Przybyszewskiego 63-77, 51-148 Wroclaw, Poland
Bibliografia
- 1. Tyman, J.H.P. (1991) The chemistry of non-isoprenoid phenolic lipids; in Studies in- natural products chemistry (Atta-ur-Rahman, ed.) pp. 313-381, Elsevier, Amsterdam.
- 2. Wenkert, E., Loeser, E.-M., Mahapatra, S.N., Schenker, F. & Wilson, E.M. (1964) Wheat bran phenols. J. Org. Chem. 29,435-439.
- 3. Wieringa, G. W. (1967) On the occurrence of growth inhibiting substances in rye. Veenman H., Wageningen.
- 4. Briggs, D.E. (1974) Hydrocarbons, phenols and sterols of the testa and pigment strand in the grain of Hordeum distichon. Phytochemistry 13, 987-996.
- 5. Bouillant, M.L., Jacoud, C., Zanella, I., Favrebonvin, J. & Bally, R. (1994) Identification of 5-(12-heptadecenyl)-resorcinol in rice root exudates. Phytochemistry 35, 769-771.
- 6. Kozubek, A. & Demel, R.A. (1980) Permeability changes of erythrocytes and liposomes by 5-(n-alk(en)yl)resorcinols from rye. Biochim. Biophys. Acta 603,220-227.
- 7. Kozubek, A. & Demel, R.A. (1981) The effect of 5-(n-alk(en)yl)resorcinols from rye on membrane structure. Biochim. Biophys. Acta 642, 242-251.
- 8. Kozubek, A. (1984) Haemolytic properties of cereal 5-n-alk(en)yIresorcinols. Z. Naturforsch. 39c, 1132-1136.
- 9. Kozubek, A. (1985) Higher cardol homologues (5-alkenyIresorcinols) from rye affect the red cell membrane-water transport. Z. Naturforsch. 40c, 80-84.
- 10. Kozubek, A. (1987) The effect of 5-(n-alk(en)yl)resorcinols on membranes. I. Characterization of the permeability increase induced by 5-(n-heptadecenyI) resorcinol. Acta Biochim. Polon. 34,357-367.
- 11. Kozubek, A. (1987) The effect of 5-(n-alk(en)yl)resorcinols on membranes. II. Dependence on the aliphatic chain length and unsaturation. Acta Biochim. Polon. 34,387-394.
- 12. Kozubek, A., Jezierski, A. & Sikorski, A.F. (1988) The effect of nonadec(en)ylresorcinol on the fluidity of liposome and erythrocyte membranes. Biochim. Biophys. Acta 944,465-472.
- 13. Hendrich, A.B. & Kozubek, A. (1991) Calorimetric study on the interactions of 5-n-heptadec(en)yIresorcinols from cereal grains with zwitterionic phospholipid (DPPC). Z. Naturforsch. 46c, 423-427.
- 14. Kozubek, A. (1993) Aktywność biologiczna lipidów rezorcynoiowych. Post. Blochem. 39, 264-270 (in Polish).
- 15. Vincieri, F.F., Vinzenzini, M.T. & Vanni, P. (1981) Extraction of active compounds from sarcotesta of Ginkgo biloba seed: inhibition of some dehydrogenase activities. Riv. Ital. EPPOS 63, 79-82.
- 16. Tsuge, N., Mizokami, M., Imai, S., Shimazu, A. & Seto, H. (1992) Adipostatins A and B, new inhibitors of glycerol-3-phosphate dehydrogenase. /. Antibiot. 45,886-891.
- 17. Toyomizu, M., Sugiyama, S., Jin, R.L. & Nakatsu, T. (1993) Alpha-glucosidase and aldose reductase inhibitors: constituents of cashew, Anacardium occidentale, nut shell liquids. Phytother. Res. 7, 252-254.
- 18. Kozubek, A. (1985) Isolation of 5-n-aIkyl, 5-n-alkenyl- and 5-n-alkdienyl- resorcinol ho- mologs from rye grains. Acta Aliment. Polon. 9, 185-198.
- 19. Kunitz, M. (1947) Crystalline soybean trypsin inhibitor. II. General properties. J. Gen. Physiol. 30, 291-310.
- 20. Adam, N.K. (1928) The structure of thin films. Part XI. Oxygenated derivatives of benzene. Proc. Roy. Soc. (Ser. A) 119, 628-644.
- 21. Kato, T., Seki, K. & Kaneko, R. (1986) Insoluble monolayers of irisquinone and its related substances at the air/water interface. }. Colloid Interface Sci. 109,77-89.
- 22. Sikorski, A.F., Michalak, K., Bobrowska, M. & Kozubek, A. (1987) Interaction of spectrin with some amphipatic compounds. Studia Biophys. 121,183-191.
- 23. Kieleczawa, J., Szalewicz, A., Kozubek, A. & Kulig, E. (1987) Effect of resorcinols on electron transport in pea chloroplasts. Progr. Photosynth. Res. 2,585-587.
- 24. Liu, K., Markakis, P. & Smith, D. (1990) Trypsin inhibition by free fatty acids and stearoyl-CoA. J. Agric. Food Chem. 38,1475-1478.
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Bibliografia
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