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Phenolic Compounds in Plants of Pharmaceutical Interest

  • H. Wagner
Part of the Recent Advances in Phytochemistry book series (RAPT, volume 12)

Abstract

Nearly all naturally occurring phenolic compounds, including phenol itself and the polyphenolic tannins, possess some biological or pharmacological activity. This is not surprising for the phenolic OH-group has a strong affinity for proteins, and therefore for enzymes. This activity is vividly illustrated by the astringent and tanning activity of vegetable polyphenols on skin proteins. In model experiments with polymeric amides, such as perlon or nylon, it can be shown that the bond energy of the hydrogen bonds between phenols and the amides of the polyamide chain is almost twice high as that between the polyamide chains themselves17(see Fig. 1). In model experiments it can be demonstrated that phenols are actually able to break the bonds between the polyamide chains and penetrate to the inside of the polymers, thus causing the polyamide to swell. This kind of action is used in biochemistry to solubilize proteins and, for example, to separate them from polysaccharides. The elution curves for the removal of various phenols from polyamide show that the strength of binding does not depend solely on the number of phenolic OH-groups. Thus pyrogallol is eluted more rapidly than phenol, or nitrophenol and gallic acid, for example, is more strongly adsorbed than any of these compounds. In addition to the size of the molecule, neighbouring group effects, and delocalizability, the electron donor or acceptor character of a given molecule makes a significant contribution to the bonding ability and the strength of bonding of phenols with biological material. Such relationships can only be described on the basis of molecular biology, and they can only be measured by applying quantum chemical methods.

Keywords

Phenolic Compound Aldose Reductase Coniferyl Alcohol Pharmaceutical Interest Spasmolytic Activity 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Berger, H. and H. Holler. 1957. Scientia pharmaceutica25: 172.Google Scholar
  2. 2.
    Böhm, B. A. 1975. The Flavonoids. (Ed.) J. B. Harborne, T. J. Mabry and H. Mabry. Chapman and Hall, London, p.492.Google Scholar
  3. 3.
    Bohm, K. 1967. Die Flavonoide. (Ed.) Cantor KG, Aulendorf/Wurtt.Google Scholar
  4. 4.
    Braatz, R. and C. C. Schneider. 1976. Symposium on the Pharmacodynamics of Silymarin. Urban and Schwarzenberg-Verlag, München - Berlin - Wien.Google Scholar
  5. 5.
    Chan, B. Y. I., K. K. Cheung and K. M. Li. 1970. Far East Med. J.6: 259.Google Scholar
  6. 6.
    Chawla, H. P. S., P. K. Grover, N. Anand, V. P. Karnboj and A. B. Kar. 1970. J. Med. Chem.23: 54.CrossRefGoogle Scholar
  7. 7.
    Comel, M. and L. Laszt. 1972. Clinical Pharmacology: Flavonoids and Vascular Wall Symposia Angiogica Santorian 4th Int. Symp. Fribourg-Nyon. (Ed.) S. Karger, Basel-Munchen-Paris-London-New York-Sydney.Google Scholar
  8. 8.
    Cordell, G. A. 1977. New Natural Products and Plant Drugs with pharmacological, biological or therapeutical activity. Proceedings in Life Sciences. Springer-Verlag, Berlin-Heidenberg-New York, p. 54.CrossRefGoogle Scholar
  9. 9.
    Dinya, Z. and E. Hetenyi. 1975. Topics in Flavonoid Chemistry and Biochemistry. Proc. of IV. Hung. Bioflavonoid Symposium Keszthely 1973. (Ed.) L. Farkas, M. Gabor and F. Kallay,Akademiai Kiado, Budapest.Google Scholar
  10. 10.
    Dittman, J. H., D. Herrmann and H. Palleske. 1972. Arzneimittel-Forsch. (Drug Res.)12: 1999.Google Scholar
  11. 11.
    Farkas, L., M. Nogradi, A. Gottsegen and F. Antus. 1973. Ung. Patent Amt163.394 Deutsche Offenlegungsschrift 2258.3045.7Google Scholar
  12. 12.
    Farnsworth, N. R. and G. A. Cordell. 1977. Lloydia39: 420.Google Scholar
  13. 13.
    Felix, W. 1972. Dtsch. Med. J.23: 403.PubMedGoogle Scholar
  14. 14.
    Gabor, M. 1974. Pathophysiology and Pharmacology of Capillary Resistance. Akademiai Kiado, Budapest.Google Scholar
  15. 15.
    Gabor, M. 1975. Abriss der Pharmakologie von Flavonoiden, Akademiai Kiado, Budapest.Google Scholar
  16. 16.
    Gordonoff, T. and S. Rodel. 1960. Hippokrates31: 335.PubMedGoogle Scholar
  17. 17.
    Grassmann, W., H. Hormann and A. Hartl. 1956. Makro molekulare Chemie21: 37.CrossRefGoogle Scholar
  18. 18.
    Hahn, G., H. D. Lehmann, M. Kurten, H. Hebel and G. Vogel. 1968. Arzneimittel-Forsch. (Drug Res.)18: 698.Google Scholar
  19. 19.
    Harada, M. and S. Yano. 1975. Chem. Pharm. Bull.23: 941.PubMedCrossRefGoogle Scholar
  20. 20.
    Hayman, S. and J. H. Kinoshita. 1965. J. Biol. Chem.240: 877.PubMedGoogle Scholar
  21. 21.
    Hansel, R. M. Kaloga and A. Pelter. 1976. Tetrahedron Letters. 2241.Google Scholar
  22. 22.
    Holzl, J. Unpublished resulsts.Google Scholar
  23. 23.
    Holzl, J. and A. Strauch. 1977. Planta med.32: 141.PubMedCrossRefGoogle Scholar
  24. 24.
    Hörhammer, L. 1961. Ber. XXI Internat. Kongress Pharmaz. Wissenschaften, Pisa.Google Scholar
  25. 25.
    Horowitz, R. M. and B. Gentili. 1963. U.S. Patent 3.087.821.Google Scholar
  26. 26.
    Inglett, G. E., L. Krbechok, B. Dowling and R. Wanger. 1969. J. Food Science 101.Google Scholar
  27. 27.
    Johnson, G., S. G. Sunderwirth, H. Gibian, A. W. Coulter and F. X. Gassner. 1963. Phytochemistry2: 145.CrossRefGoogle Scholar
  28. 28.
    Jurcic, X. and H. Wagner. 1976. 1. International Congress for Research on Medicinal Plants, München.Google Scholar
  29. 29.
    Kaczmarek, F., B. Ostrowska and K. Szpunar. 1962. Biol. Inst. Roslin Leczniczych8: 111Google Scholar
  30. 30.
    Kaczmarek, F., B. Ostrowska and K. Szpunar. 1963. C.A.58: 14589.Google Scholar
  31. 31.
    Kelley, C. J., J. R. Mahajan, L. C. Brooks, L. A. Neubert, W. R. Brenemann and M. Carmach. 1975. J. Org. Chem.40: 1804.CrossRefGoogle Scholar
  32. 32.
    Kinoshita, J. H. 1974. Invest. Ophthamlmol.33: 713.Google Scholar
  33. 33.
    Kozhina, I. S., B. A. Shukhobodskii, L. A. Klyuchnikova, V. M. Dillman, and E. P. Alpatskaya. 1970. Rastit. Resur. 6: 345.Google Scholar
  34. 34.
    Kozhina, I. S., B. A. Shukhobodskii, L. A. Klyuchnikova, V. M. Dillman, and E. P. Alpatskaya. 1971 C.A.74: 72812.Google Scholar
  35. 35.
    Kupchan, S. M. and E. Bauerschmidt. 1971. Phytochemistry10: 661.CrossRefGoogle Scholar
  36. 36.
    Kupchan, S. M., R. W. Britten, M. F. Ziegler, C. J. Gilmore, R. J. Restivo and R. F. Bryan. 1973. J. Chem. Soc. 1335.Google Scholar
  37. 37.
    Kupchan, S. M., J. R. Knox and M. S. Udayamurthy. 1965. J. Pharm. Sci.54: 929. 614PubMedCrossRefGoogle Scholar
  38. 38.
    Kupchan, S. M., C. W. Siegel, J. R. Knox and M. S. Udayamurthy. 1969. J. Org. Chem.34: 1460.CrossRefGoogle Scholar
  39. 39.
    Lasswell Jr., W. L and C. D. Hufford. 1977. J. Org. Chem. 1295.Google Scholar
  40. 40.
    Le Quesne, P. W., M. P. Pastore and R. F. Raffauf. 1977. Lloydia39: 392.Google Scholar
  41. 41.
    Maehicao, F. and J. Sonnenbichler. 1977. Hoppe-Seyler’s. Z. Physiol. Chem.358: 141.CrossRefGoogle Scholar
  42. 42.
    Maj, J., D. Malec and Z. Lastowski. 1966. Acta Polon. Pharmac.23: 477.Google Scholar
  43. 43.
    Maros, T., L. Seres-Sturm, G. Racz, C. Rettegi, V. V. Kovacs and M. Hints. 1968. Arzneimittel- Forsch. (Drug Res.)18: 884.Google Scholar
  44. 44.
    Matsura, S. Japan Kokai 75: 14,676 (U. 16E41).Appl. 73: 65.390. C.A. 83: 13146a.Google Scholar
  45. 45.
    Meyers, F. H., E. Jawetz and A. Goldfien. 1972. Review of Medical Pharmacology 3rd Ed. Lange Medical Publications, Los Altos, California.Google Scholar
  46. 46.
    Parrot, J.-L. and P. Carni. 1964. Arch. Int. Pharmacodyn. 234.Google Scholar
  47. 47.
    Pelter, A. and R. Hansel. 1975. Chem. Ber.108: 790.CrossRefGoogle Scholar
  48. 48.
    Rajky-Medveczky, G., M. Takacs-Palasti, E. Bolla-Pusztai and J. Szejtli. 1977. Die Nahrung21: 131.PubMedCrossRefGoogle Scholar
  49. 49.
    Reiter, M. 1967. Arzneimittel-Forsch. (Drug Res.)17: 1249.Google Scholar
  50. 50.
    Rewerski, W. and St. Lewak. 1967. Arzneimittel-Forsch. (Drug Res.)17: 490.Google Scholar
  51. 51.
    Rewerski, W., T. Piechocki, M. Rylski and S. Lewak. 1971. Arzneimittel-Forsch. (Drug Res.)21: 886.Google Scholar
  52. 52.
    Rosler, H., A.E. Star and T. J. Mabry. 1971. Phytochemistry10: 450.CrossRefGoogle Scholar
  53. 53.
    Rossi, G. v., E. W. Blackman and M. E. Goldberg. 1957. Amer. J. Pharm,129: 89.PubMedGoogle Scholar
  54. 54.
    Saleh, A. A., G. A. Cordell and N. R. Farnsworth. 1976. Lloydia39: 456.PubMedGoogle Scholar
  55. 55.
    Segelman, A. B., F. P. Segelman, S. D. Varma, H. Wagner and O. Seligmann. J. Pharm. Sci. (in press).Google Scholar
  56. 56.
    Sik, C. J., P. R. Ravikumar, F. C. Huang, C. Bruckner and H. Whitlock Jr. 1976. J. Am. Chem. Soc.98: 17, 5412.CrossRefGoogle Scholar
  57. 57.
    Sonnenbichler, J., J. Mattersberger and H. Rosen. Hoppe-Seyler’s Z. Physiol. Chem. 357: 1171.Google Scholar
  58. 58.
    Sprinkmeyer, L. 1971. Dissertation München.Google Scholar
  59. 59.
    Suolinna, E. M., R. N. Buchsbaum and E. Racker. 1975. Cane. Res. 1865.Google Scholar
  60. 60.
    Suolinna, E. M., D. R. Lang and E. Racker. 1974. J. Nat. Cane. Res. 1515.Google Scholar
  61. 61.
    Varma, S. D. and J. H. Kinoshita. 1974. Biochim. Biophys. Acta 632.Google Scholar
  62. 62.
    Varma, S. D. and J. H. Kinoshita. 1974. Exp. Eye Res.19: 577.PubMedCrossRefGoogle Scholar
  63. 63.
    Varma, S. D., I. Mikani and J. H. Kinoshita. 1975. Science188: 1215.PubMedCrossRefGoogle Scholar
  64. 64.
    Vogel, G. 1971. In: Pharmacognosy and Phytochemistry. (H. Wagner and L. Horhammer, eds.). Springer- Verlag, Berlin-Heidelberg, New York, p. 370–86.CrossRefGoogle Scholar
  65. 65.
    Wagner, H., V. M. Chari, M. Seitz and I. Riess-Maurer. Tetrahedron Letters, (in press).Google Scholar
  66. 66.
    Wagner, H., L. Horhammer and U. Frank. 1970. Arzneimittel-Forsch.20: 705.Google Scholar
  67. 67.
    Wagner, H., L. Horhammer and R. Munster. 1968. Arzneimittel-Forsch. (Drug Res.)18: 688.Google Scholar
  68. 68.
    Wagner, H., I. Maurer, L. Farkas and J. Strelisky. Tetrahedron 33: 1405.Google Scholar
  69. 69.
    Wagner, H., I. Riess-Maurer, L. Farkas and J. Strelisky. 1977. Tetrahedron33: 1411.CrossRefGoogle Scholar
  70. 70.
    Wagner, H., O. Seligmann, M. Seitz, D. J. Abraham, and J. Sonnenbichler. 1971. Tetrahedron Letters 1895.Google Scholar
  71. 71.
    Wagner, H., O. Seligmann, M. Seitz, D.J. Abraham, and J. Sonnenbichler. 1976. Z. Naturforsch.31b: 876.Google Scholar
  72. 72.
    Wagner, H., D. Wittmann and W. Schäfer. 1975. Tetrahedron Letters 547.Google Scholar
  73. 73.
    Wattenberg, L. W. and J. L. Leong. 1970. Cane. Res.30: 1922.Google Scholar
  74. 74.
    Weinges, K., P. Kloss and H. Jaggy. 1972. Arzneimittel-Forsch. (Drug Res.)22: 166.Google Scholar
  75. 75.
    Weinges, K., P. Kloss, G. Trunzler and E. Schuler 1971. Planta Med.4: 61.CrossRefGoogle Scholar
  76. 76.
    Weiss, S. G., M. Tin-Wa, R. E. Perdue, Jr. and N. R. Farnsworth. 1975. J. Pharm. Sci.64: 95. 616Google Scholar
  77. 77.
    Wollenweber, E. and E. Racker. 1976. 1. International Congress for Research on Medicinal Plants, Munich. Abstr. Section A.Google Scholar

Copyright information

© Plenum Press, New York 1979

Authors and Affiliations

  • H. Wagner
    • 1
  1. 1.Institut für Pharmazeutische ArzneimittellehreUniversität MünchenMünchenDeutschland

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