PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
1995 | 42 | 2 |

Tytuł artykułu

Determination of octanol-water partition coefficients for long-chain homologs of orcinol from cereal grains

Autorzy

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
Polycratic reversed-phase high-performance liquid chromatography (RPHPLC) was used for estimation of the octanol/water partition coefficient for three highly hydrophobic long chain orcinol homologs. The homologs studied (C 15:0, C 17:0 and C 19:0) showed high preference for hydrophobic phase as evidenced by their high octanol/water partition coefficient (log P o/w ) values of 7.02-7.74; 8.71-9.47 and 10.49-11.32 for the 95% prediction interval, respectively. Experimentally estimated values were compared with log P values calculated with the use of several fragmental systems. The experimental values of log P o/w are in best agreement to those calculated with the use of the Klopman system (Klopman, Gv Namboodiri, K. & Schochet, M., 1985, /. Comput. Chem. 6,28-38). The lack of appropriate standard compounds with known log P 0/w in the range over 6 markedly affected the accuracy of experimental determinations.

Wydawca

-

Rocznik

Tom

42

Numer

2

Opis fizyczny

p.247-251,fig.

Twórcy

autor
  • University of Wroclaw, S.Przybyszewskiego 63-77, 51-148 Wroclaw, Poland

Bibliografia

  • 1. Al-Gailany, K.A.S., Houston, J.B. & Bridges, J.B. (1978) Biochem. Pharmacol. 27, 783.
  • 2. Hansch, C. & Leo, A. (1979) Substituent constants for correlation analysis in chemistry and biology. Wiley, New York.
  • 3. Hansch, C. & Fujita, T. (1964) p-8-7i Analysis. A method for the correlation of biological activity and chemical structure. }. Am. Chem. Soc. 86, 1616-1625.
  • 4. Itokawa, H., Totsuka, N., Nakahara, K., Maezuru, M., Takeya, K., Kondo, M., Inamatsu, M. & Morita, H. (1989) A quantitative structure-activity relationship for antitumor activity of long-chain phenols from Ginkgo biloba L. Chem. Pharm. Bull. 37,1619-1621.
  • 5. Komolova, G.S., Gorskaya, I.A., Kaverinskaya, T.V. & Sheveleva, I.D. (1989) Influence of alkylresorcinol on respiration, nucleic acid and protein synthesis in isolated thymocytes. Biokhimiya 54,1847-1851.
  • 6. Kozubek, A. (1984) Haemolytic properties of cereal 5-n-alk(en)ylresorcinols. Z. Naturforsch. 39c, 1132-1136.
  • 7. Kozubek, A. (1985) Higher cardol homologues (5-n-alkenylresorcinols) from rye affect the red cell membrane water transport. Z. Naturforsch. 40c, 80-84.
  • 8. Kozubek, A. (1985) Isolation of 5-n-alkyl, 5-n-alkenyl- and 5-n-alkdienyl-resorcinol homologs from rye grains. Acta Aliment. Polon. 9,185-198.
  • 9. Kozubek, A. & Demel, R.A. (1981) The effect of 5-(n-alk(en)yI)resorcinols from rye on mem­brane structure. Biochim. Biophys. Acta 642, 242-251.
  • 10. 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.
  • 11. 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.
  • 12. Kozubek, A., Nietubyc, M. & Sikorski, A.F. (1992) Modulation of the activities of membrane enzymes by cereal grain resorcinolic lipids. Z. Naturforsch. 47c, 41^46.
  • 13. Kozubek, A. & Wróblewski, Z. (1990) Cereal grain long chain amphiphilic resorcinolic lipids inhibit significantly binding of fibrinogen by platelets whereas short chain resorcinolic lipids and fatty acids do not. Studia Biophys. 139, 177-181.
  • 14. Scannell, R.T., Barr, J.R., Murty, V.S., Reddy, K.S. & Hecht, S.M. (1988) DNA strand scission by naturally occurring 5-aIkylresorcinols. J, Am. Chem. Soc. 110,3650-3651.
  • 15. Shoji, N., Umeyama, A. & Takemoto, T. (1984) Na+-K+-ATPase inhibitors from Lysimachia japonica. J. Nat. Prod. (Lloydia) 47,530-532.
  • 16. 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.
  • 17. Tsuge, N., Mizokami, ML, Imai, S., Shimazu, A. & Seto, H. (1992) Adipostatins A and B, new inhibitors of glycerol-3-phosphate dehydro­genase. J. Antibiot. 45, 886-891.
  • 18. 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. Hal. EPPOS 63, 79-82.
  • 19. Hengtrakul, P., Lorenz, K. & Mathias, M. (1991) Alkylresorcinol homologs in cereal grains. /. Food Comp. Anal. 4,52-57.
  • 20. Mullin, W.J., Wolynetz, M.S. & Emery, J.P. (1992) A comparison of methods for the extraction and quantitation of alk(en)y!resorcinoIs. ]. Food Comp. Anal. 5,216-223.
  • 21. Leo, A., Hansch, C. & Elkins, D. (1971) Partition coefficients and their use. Chem. Rev. 71, 525-613.
  • 22. McCall, J.M. (1975) Liquid-liquid partition coefficients by high-pressure liquid chromatography. J. Med. Chem. 18,549-552.
  • 23. Minick, D.J., Frenz, J.H., Patrick, M.A. & Brent, D.A. (1988) A comprehensive method for determining hydrophobicity constants by reversed-phase high-performance liquid chromatography.}. Med. Chem. 31,1923-1933.
  • 24. Valko, K. (1984) General approach for the estimation of octanol/water partition coefficient by reversed-phase high-performance liquid chromatography. }. Liq. Chromatogr. 7, 1405-1424.
  • 25. Harnisch, M„ Mockel, H.J. & Schultze, G. (1983) Relationship between log Po/w shake-flask values and capacity factors derived from reversed-phase high-performance liquid chromatography for n-alkylbenzenes and some OECD reference substances. }. Chromatogr. 282, 315-332.
  • 26. Braumann, T. (1986) Determination of hydrophobic parameters by reversed-phase liquid chromatography: Theory, experimental techniques, and application in studies on quantitative structure-activity relationships. /. Chromatogr. 373,191-225.
  • 27. Rekker, R.F. & de Kort, H.M. (1979) The hydrophobic fragmental constant; an extension to a 1000 data point set. Eur. }. Med. Chem. 14, 479^88.
  • 28. Klopman, G., Namboodiri, K. & Schochet, M. (1985) Simple method of computing the partition coefficient. ]. Comput. Chem. 6, 28-38.

Typ dokumentu

Bibliografia

Identyfikatory

Identyfikator YADDA

bwmeta1.element.agro-article-7e1aebf4-6bfc-43db-9462-821173a7dfbe
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.