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Metabolism of vitamin A, structure and synthesis of metabolites, and their biological activity (Review)

  • Molecular-Biological Problems in the Creation of Drugs and Study of the Mechanism of Their Action
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Literature cited

  1. J. A. Olson, Vitam. Horm.,26, 1–63 (1968).

    Google Scholar 

  2. H. Mayer, W. Bollag, R. Hänni, et al., Experienta,34, 1105–1119 (1978).

    Google Scholar 

  3. G. Wald, Science,162, 230–239 (1968).

    Google Scholar 

  4. L. M. DeLuca, Vitam. Horm.,35, 1–57 (1977).

    Google Scholar 

  5. G. Wolf and D. Phil, Nutr. Rev.,35, 97–99 (1977).

    Google Scholar 

  6. J. G. Bieri, E. G. McDaniel, and W. E. Rogers, Science,163, 574–578 (1969).

    Google Scholar 

  7. G. A. J. Pitt, in: Garotenoids (O. Isler, ed.), Basel (197.1), pp. 717–742.

  8. M. B. Sporn, N. M. Dunlop, D. L. Nenton, et al., Fed. Proc.,35, 1332–1338 (1976).

    Google Scholar 

  9. A. O. Natanson and I. Ya. Kon', Vopr. Pitan., No. 3, 3–12 (1979).

    Google Scholar 

  10. L. A. Chernukhina, A. G. Khalmuradov, and A. A. Dusheiko, Usp. Sovrem. Biol.,87, 393–403 (1979).

    Google Scholar 

  11. J. E. Smith and D. S. Goodman, Fed. Proc.,38, 2504–2509 (1979).

    Google Scholar 

  12. J. Glover, in: Garotenoids, Oxford (1982), pp. 265–272.

  13. D. S. Goodman, H. S. Huang, M. Kanai, et al., J. Biol. Chem.,242, 3543–3554 (1967).

    Google Scholar 

  14. N. H. Fidge and D. S. Goodman, ibid.,243, 4372–4379 (1968).

    Google Scholar 

  15. L. Rask, H. Arundi, and P. A. Peterson, FEBS Lett.,104, 55–58 (1979).

    Google Scholar 

  16. D. E. Ong and F. Chytil, J. Biol. Chem.,253, 828–832 (1978).

    Google Scholar 

  17. G. Wald and R. Hubbard, Proc. Natl. Acad. Sci. USA,36, 92–102 (1950).

    Google Scholar 

  18. J. T. Arens and D. A. van Dorp, Nature,158, 622–623 (1946).

    Google Scholar 

  19. H. F. DeLuca, Fed. Proc.,38, 2519–2523 (1979).

    Google Scholar 

  20. R. J. Emerich, M. Zile, and H. F. DeLuca, Biochem. J.,102, 606–611 (1967).

    Google Scholar 

  21. M. Zile and H. F. DeLuca, ibid.,97, 180–186 (1965).

    Google Scholar 

  22. M. Zile, R. J. Emerich, and H. F. DeLuca, Biochim. Biophys. Acta,141, 639–641 (1967).

    Google Scholar 

  23. R. D. Zachman and J. A. Olson, Nature,201, 1222–1223 (1964).

    Google Scholar 

  24. P. E. Dunagin, E. H. Meadows, and J. A. Olson, Science,148, 86–87 (1965).

    Google Scholar 

  25. M. Zile, H. K. Schnoes, and H. F. DeLuca, Proc. Natl. Acad. Sci. USA,77, 3230–3233 (1980).

    Google Scholar 

  26. M. Zile, R. C. Inhorn, and H. F. DeLuca, J. Biol. Chem.,257, 3537–3544 (1982).

    Google Scholar 

  27. M. Zile, R. C. Inhorn, and H. F. DeLuca, ibid., 3544–3550.

    Google Scholar 

  28. A. B. Roberts and H. F. DeLuca, Biochem. J.,102, 600–605 (1967).

    Google Scholar 

  29. R. Hänni and F. Bigler, Helv. Chim. Acta,60, 881–887 (1977).

    Google Scholar 

  30. P. R. Sundaresan and G. M. Sundaresan, Int. J. Vitam.,43, 61–69 (1973).

    Google Scholar 

  31. R. Hänni, F. Bigler, W. Meister, et al., Helv. Chim. Acta.,59, 2221–2228 (1976).

    Google Scholar 

  32. P. Rietz, O. Wiss, and F. Weber, Vitam. Horm.,32, 237–249 (1974).

    Google Scholar 

  33. C. A. Frolik, B. N. Swanson, L. L. Dart, et al., Arch. Biochem.,208, 344–352 (1981).

    Google Scholar 

  34. K. L. Skare, H. K. Schnoes, and H. F. DeLuca, Biochemistry,21, 3308–3317 (1982).

    Google Scholar 

  35. K. Jagashita, P. R. Sundarasan, and G. A. Wolf, Nature,203, 410–412 (1964).

    Google Scholar 

  36. J. Ito, M. Zile, H. F. DeLuca, et al., Biochim. Biophys. Acta,369, 338–350 (1974).

    Google Scholar 

  37. A. M. McCormick, J. L. Napoli, H. K. Schnoes, et al., Arch. Biochem.,192, 577–583 (1979).

    Google Scholar 

  38. J. L. Napoli, A. M. McCormick, H. K. Schnoes, et al., Proc. Natl. Acad. Sci. USA,75, 2603–2605 (1978).

    Google Scholar 

  39. A. M. McCormick, J. L. Napoli, H. K. Schnoes, et al., Biochemistry,17, 4085–4090 (1978).

    Google Scholar 

  40. A. M. McCormick and J. L. Napoli, J. Biol. Chem.,257, 1730–1735 (1982).

    Google Scholar 

  41. A. M. McCormick, J. L. Napoli, S. Yoshizawa, et al., Biochem. J.,186, 475–481 (1980).

    Google Scholar 

  42. J. L. Napoli, H. Khalil, and A. M. McCormick, Biochemistry,21, 1942–1949 (1982).

    Google Scholar 

  43. W. K. Sietsema and H. F. DeLuca, J. Biol. Chem.,257, 4265–4270 (1982).

    Google Scholar 

  44. H. F. DeLuca and W. K. Sietsema, Biochem. Biophys. Res. Commun.,90, 1091–1097 (1979).

    Google Scholar 

  45. Ch. Frolik, L. Dart, and M. B. Sporn, Biochim. Biophys. Acta,663, 329–336 (1981).

    Google Scholar 

  46. Ch. Frolik, T. E. Tavela, D. L. Newton, et al., J. Biol. Chem.,253, 7319–7329 (1978).

    Google Scholar 

  47. A. Roberts, L. S. Lamb, and M. B. Sporn, Arch. Biochem.,199, 374–383 (1980).

    Google Scholar 

  48. A. Roberts, M. D. Nichols, D. L. Nenton, et al., J. Biol. Chem.,254, 6296–6302 (1979).

    Google Scholar 

  49. A. Roberts, Ch. Frolik, M. D. Nichols, et al., ibid., 6303–6309.

    Google Scholar 

  50. Ch. Frolik, A. B. Roberts, T. E. Tavela, et al., Biochemistry,18, 2092–2997 (1979).

    Google Scholar 

  51. A. B. Roberts and Ch. Frolik, Fed. Proc.38, 2524–2527 (1979).

    Google Scholar 

  52. Ch. Frolik, P. P. Roller, A. B. Roberts, et al., J. Biol. Chem.,255, 8057–8062 (1980).

    Google Scholar 

  53. W. L. Miller and J. L. Gaylor, ibid.,245, 5375–5381 (1970).

    Google Scholar 

  54. Ch. A. West, Biochem. J.,114, 3P-4P (1969).

    Google Scholar 

  55. D. G. Austin, J. D. Bu'Lock, and D. J. Winstanley, ibid.,113, 34.

    Google Scholar 

  56. H. Van den Ende, Nature,215, 211–212 (1967).

    Google Scholar 

  57. H. Van den Ende and D. Stegwee, Bot. Rev.,37, 22–36 (1971).

    Google Scholar 

  58. G. W. Gooday, Symp. Soc. Gen. Microbiol.,23, 269–296 (1973).

    Google Scholar 

  59. D. G. Austin, J. D. Bu'Lock, and D. Drake, Experienta,26, 348–349 (1970).

    Google Scholar 

  60. J. D. Bu'Lock, B. E. Jones, D. Taylor, et al., J. Gen. Microbiol.,80, 301–306 (1974).

    Google Scholar 

  61. J. D. Bu'Lock, B. E. Jones, and N. Winskill, Chem. Commun., No. 17, 708–709 (1974).

    Google Scholar 

  62. J. D. Bu'Lock, B. E. Jones, and N. Winskill, Pure Appl. Chem.,42, 191–203 (1976).

    Google Scholar 

  63. S. Isoe, Y. Hayase, and T. Sakan, Tetrahedron Lett., 3691–3694 (1971).

  64. J. A. Edwards, V. Schwarz, J. Fajkos, et al., Chem. Commun., 292–294 (1971).

  65. L. A. Vakulova, L. N. Fokina, V. V. Mishchenko, et al., Zh. Obshch. Khim.,45, 2499–2506 (1975).

    Google Scholar 

  66. J. A. Secrist III, C. J. Hickey, and R. S. Norris, J. Org. Chem.,42, 525–527 (1977).

    Google Scholar 

  67. M. P. Prisbylla, K. Takabe, and J. D. White, J. Am. Chem. Soc.,101, 762–763 (1979).

    Google Scholar 

  68. I. M. Yakovleva, L. A. Vakulova, A. R. Bekker, and G. I. Samokhvalov, Zh. Org. Khim.,14, 714–721 (1978).

    Google Scholar 

  69. I. M. Yakovleva, L. A. Vakulova, T. M. Filippova, et al., ibid.,16, 2289–2296 (1980).

    Google Scholar 

  70. I. M. Yakovleva, L. A. Vakulova, V. M. Zhulin, et al., USSR Patent No. 1004350, Otkrytiya, No. 10 (1983).

  71. M. Rosenberger, J. Org. Chem.,47, 1698–1701 (1982).

    Google Scholar 

  72. M. Rosenberger, ibid., 1779–1782.

    Google Scholar 

  73. M. Rosenberger and C. Neukom, ibid., 1782–1785.

    Google Scholar 

  74. P. Entsche and P. Karrer, Helv. Chim. Acta,41, 402 (1958).

    Google Scholar 

  75. W. Bollag and A. Matter, Ann. N. Y. Acad. Sci.,359, 9–24 (1981).

    Google Scholar 

  76. W. Bollag, Experienta,30, 1198–1200 (1974).

    Google Scholar 

  77. W. Bollag and A. Hanck, Acta Vitaminol. (Milano),31, 113–123 (1977).

    Google Scholar 

  78. W. Bollag, Cancer Chemother. Rep.,55, 53–58 (1971).

    Google Scholar 

  79. E. W. Chu and R. A. Malmgren, Cancer Res.,25, 884–895 (1965).

    Google Scholar 

  80. R. Lotan, Biochim. Biophys. Acta,605, 33–91 (1980).

    Google Scholar 

  81. R. Peto, R. Dol, J. D. Buckey, et al., Nature,290, 201–208 (1981).

    Google Scholar 

  82. E. Siefer, G. Retture, J. Padawer, et al., J. Natl. Cancer Inst.,62, 835–840 (1982).

    Google Scholar 

  83. M. M. Mathews-Roth, Oncology,39, 33–37 (1982).

    Google Scholar 

  84. G. Dennert and R. Lotan, Eur. J. Immunol.,8, 23–29 (1978).

    Google Scholar 

  85. R. S. Moon, H. J. Thimpson, P. J. Becci, et al., Cancer Res.,39, 1339–1347 (1979).

    Google Scholar 

  86. D. L. Newton, J. M. Smith, S. L. Phillips, et al., Proc. Am. Assoc., Cancer Res.,20, 120. (1979).

    Google Scholar 

  87. D. L. Newton, W. R. Henderson, and M. B. Sporn, Cancer Res.,40, 3413–3425 (1980).

    Google Scholar 

  88. W. Bollag, Cancer Chemother. Pharmacol.,3, 207–215 (1979).

    Google Scholar 

  89. W. Bollag, Int. J. Vitam.,40, 422–461 (1970).

    Google Scholar 

  90. J. T. Dingl and J. A. Lucy, Biol. Rev.,40, 422–461 (1965).

    Google Scholar 

  91. J. F. Tannock, D. H. Suit, and N. Marshall, J. Natl. Cancer Inst.,48, 731–741 (1972).

    Google Scholar 

  92. P. W. Trown, A. V. Palleroni, O. Bohoslaec, et al., Cancer Res.,40, 212–220 (1980).

    Google Scholar 

  93. P. W. Trown, M. J. Buck, and R. Hansen, Cancer Treat. Rep.,60, 1647–1653 (1976).

    Google Scholar 

  94. T. Kurata and M. Micksche, Oncology,34, 212–215 (1977).

    Google Scholar 

  95. Yu. I. Afanas'ev, V. I. Nozdrin, G. I. Samokhvalov, et al. Vopr. Onkol., No. 3, 77–81 (1983).

    Google Scholar 

  96. M. Micksche, C. Cerni, O. Kokron, et al., Oncology,34, 234–238 (1977).

    Google Scholar 

  97. K. D. Pretsityi and S. B. Vasina, Vopr. Pitan., No. 5, 60–62 (1982).

    Google Scholar 

  98. Y. Fujimaki, J. Cancer Res.,10, 469–477 (1926).

    Google Scholar 

  99. M. B. Sporn, N. M. Dunlop, D. L. Newton, et al., Nature,263, 110–113 (1976).

    Google Scholar 

  100. P. Nettscheim, Can. Med. Assoc. J.,122, 757–765 (1980).

    Google Scholar 

  101. W. Bollag, Eur. J. Cancer,10, 731–737 (1974).

    Google Scholar 

  102. C. J. Grubbs, R. S. Moon, R. A. Squire, et al., Science,198, 743–744 (1977).

    Google Scholar 

  103. M. B. Sporn, G. H. Clamon, N. M. Dunlop, et al., Nature,253, 47–50 (1975).

    Google Scholar 

  104. D. L. Newton, C. A. Frolik, A. B. Roberts, et al., Cancer Res.,38, 1734–1738 (1978).

    Google Scholar 

  105. G. H. Clamon, M. B. Sporn, J. M. Smith, et al., Nature,250, 64–66 (1974).

    Google Scholar 

  106. L. J. Wilkoff, J. C. Peckhman, E. A. Dulmadge, et al., J. Org. Chem.,47, 964–972 (1976).

    Google Scholar 

  107. B. P. Sani and D. L. Hill, ibid., 409–413.

    Google Scholar 

  108. R. Lotan and G. L. Nicolson, J. Natl. Cancer Inst.,59, 1717–1722 (1977).

    Google Scholar 

  109. R. Lotan, Proc. Am. Assoc. Cancer Res.,19, 13 (1978).

    Google Scholar 

  110. L. D. Dion, J. E. Bizlock, and G. E. Gifford, J. Natl. Cancer Inst.,58, 795–801 (1971).

    Google Scholar 

  111. R. Lotan, G. Neumann, and D. Lotan, Cancer Res.,40, 1097–1102 (1980).

    Google Scholar 

  112. J. Lasnitzki, Br. J. Cancer,34, 239–248 (1976).

    Google Scholar 

  113. A. M. Zetten and M. E. R. Zetten, Nature,278, 180–182 (1979).

    Google Scholar 

  114. P. V. Bhat, L. DeLuca, S. Adamo, et al., J. Lipid Res.,20, 357–362 (1979).

    Google Scholar 

  115. S. Adamo, L. DeLuca, I. Akalowsky, et al., J. Natl. Cancer Inst.,62, 1473–1478 (1979).

    Google Scholar 

  116. A. K. Verma, H. M. Rice, B. G. Shapas, et al., Cancer Res.,38, 793–801 (1978).

    Google Scholar 

  117. A. K. Verma and R. K. Boutwell, ibid.,37, 2196–2201 (1977).

    Google Scholar 

  118. P. W. Wertz, T. W. Kensler, G. C. Mueller, et al., Nature,277, 227–229 (1979).

    Google Scholar 

  119. T. W. Kensler, A. K. Verma, R. K. Boutuell, et al., Cancer Res.,38, 2896–2899 (1978).

    Google Scholar 

  120. T. W. Kensler and G. C. Mueller, ibid., 771–774.

    Google Scholar 

  121. A. M. Jetten, Nature,284, 626–629 (1980).

    Google Scholar 

  122. G. J. Todaro, J. E. DeLarco, and M. B. Sporn, Nature,276, 272–274 (1978).

    Google Scholar 

  123. J. E. DeLarco and G. J. Todaro, Proc. Natl. Acad. Sci. USA,75, 4001–4005 (1978).

    Google Scholar 

  124. I. M. Yakovleva, L. A. Vakulova, T. A. Zhidkova, et al., in: Summaries of Reports at the Fifth All-Union Symposium on the Directed Search for Physiologically Active Substances [in Russian], Riga (1983), p. 98.

  125. Yu. I. Afanas'ev, V. I. Nozdrin, M. Z. Bakhshinyan, Byull. Eksp. Biol. Med., No. 4, 76–78 (1982).

    Google Scholar 

  126. Yu. I. Afanas'ev, V. I. Nozdrin, and A. A. Perilov, Vopr. Onkol., No. 12, 84–86 (1979).

    Google Scholar 

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  1. Vitamin Scientific and Industrial Association, Moscow

    I. M. Yakovleva, L. A. Vakulova & G. I. Samokhvalov

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  1. I. M. Yakovleva
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  2. L. A. Vakulova
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Translated from Khimiko-farmatsevticheskii Zhurnal, Vol. 18, No. 4, pp. 391–411, April, 1984.

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Yakovleva, I.M., Vakulova, L.A. & Samokhvalov, G.I. Metabolism of vitamin A, structure and synthesis of metabolites, and their biological activity (Review). Pharm Chem J 18, 213–229 (1984). https://doi.org/10.1007/BF00760699

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