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Chemistry of Natural Compounds

, Volume 27, Issue 5, pp 521–540 | Cite as

High-performance liquid chromatography of alkaloids

  • B. D. Kabulov
  • A. L. D'yakonov
  • S. V. Zalyalieva
Article

Abstract

Literature information on the HPLC of alkaloids, including adsorption, reversed-phase, ion-exchange, ion-pair, and other variants is generalized. Results are given of the chromatographic analysis of various classes of alkaloids with an indication of the conditions of separation, and the columns used, and also of the methods of detection. The advantages and disadvantages of the HPLC variants are discussed. The review includes the literature over the last 14 years.

Keywords

Morphine Alkaloid Papaverine Ergot Alkaloid Thebaine 

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Literature cited

  1. 1.
    R. Verpoorte and A. Baerheim-Svendsen, Pharm. Week.,110, No. 42, 1021 (1975).Google Scholar
  2. 2.
    D. G. Kingston, J. Nat. Prod.,42, 237 (1979).Google Scholar
  3. 3.
    A. Wehrli, J. C. Hildenbrand, H. P. Keller, R. Stampfil, and R. W. Frei, J. Chromatogr.,149, 199 (1978).Google Scholar
  4. 4.
    K. Hostetmann and M. Hostetmann, High-Performance Liquid Chromatography in Biochemistry [Russian translation], Mir, Moscow (1988), p. 660.Google Scholar
  5. 5.
    R. Verpoorte and A. Baerheim-Svendsen, Chromatography of Alkaloids, Part B, Gas Liquid Chromatography and High Performance Liquid Chromatography, Elsevier, Amsterdam (1984).Google Scholar
  6. 6.
    M. Horstmann, J. Chromatogr.,344, 391 (1985).PubMedGoogle Scholar
  7. 7.
    D. V. McCalley, J. Chromatogr.,260, 184 (1983).Google Scholar
  8. 8.
    M. Bauer and G. Untz, J. Chromatogr.,192, 479 (1980).Google Scholar
  9. 9.
    R. Verpoorte, T. Mulder-Krieger, M. J. Verzijl, J. M. Verzijl, and A. Baerheim-Svendsen, J. Chromatogr.,261, 172 (1983).Google Scholar
  10. 10.
    A. T. Keene, L. A. Andersen, and J. D. Phillipson, J. Chromatogr.,260, 123 (1983).Google Scholar
  11. 11.
    Chi-tong Alex Chung, and E. J. Staba, J. Chromatogr.,295, 276 (1984).Google Scholar
  12. 12.
    J. Visser, G. Grasmeijer, and F. Moolenaar, J. Chromatogr.,274, 372 (1983).PubMedGoogle Scholar
  13. 13.
    M. Hutin, A. Cavé, and J. P. Foucher, J. Chromatogr.,268, 125 (1983).Google Scholar
  14. 14.
    P. Vincent and B. F. Engelke, J. Assoc. Offic. Anal. Chem.,62, No. 2, 310 (1979).Google Scholar
  15. 15.
    N. P. Sahu and S. B. Mahato, J. Chromatogr.,238, 525 (1982).Google Scholar
  16. 16.
    J.-P. Fels, P. Lechat, R. Rispe, and W. Cautreels, J. Chromatogr.,308, 273 (1984).PubMedGoogle Scholar
  17. 17.
    R. W. Frei, W. Santi, and M. Thomas, J. Chromatogr.,116, 365 (1976).PubMedGoogle Scholar
  18. 18.
    F. Tagliaro, R. Dorizzi, S. Lafisca, L. Stefani, S. Ferrari, M. Plescia, and M. Marigo, Spectroscopy,3, No. 4–5, 311 (1984).Google Scholar
  19. 19a.
    F. Tagliaro, A. Frigerio, R. Dorizzi, G. Lubli, and M. Marigo, J. Chromatogr.,330, 323 (1985).PubMedGoogle Scholar
  20. 19b.
    P. A. Biondi, T. Simonic, C. Secchi, S. Ronchi, and A. Manzocchi, J. Chromatogr.,309, 151 (1984).PubMedGoogle Scholar
  21. 20.
    A. Wahlländer, E. Renner, and G. Karlagnis, J. Chromatogr.,338, 369 (1985).PubMedGoogle Scholar
  22. 21.
    H.-U. Schulz, I. Trotnow, E. Kraas, and H. Hollandt, Chromatographia,22, Nos. 7–12, 411 (1986).Google Scholar
  23. 22.
    M. Homma, K. Oka, and N. Takahashi, Anal. Chem.,61, No. 7, 784 (1989).PubMedGoogle Scholar
  24. 23.
    B. Pekic, B. Slavica, Z. Lepojevic, and M. Gorunovic, Die Pharmazie,40, 422 (1985).Google Scholar
  25. 24.
    A. H. Lewin, S. R. Parker, and F. I. Carroll, J. Chromatogr.,193, 371 (1980).PubMedGoogle Scholar
  26. 25.
    G. Szepesy, M. Gazdag, L. Szepesy, and I. Fehér, J. Chromatogr.,149, 271 (1978).Google Scholar
  27. 26.
    G. Szepesy, M. Gazdag, and L. Terdy, J. Chromatogr.,191, 101 (1980).Google Scholar
  28. 27.
    C. Eckers, D. E. Gages, and D. N. B. Mallen, Anal. Proc.,19, No. 3, 133 (1982).Google Scholar
  29. 28.
    H. Pötter, M. Hülm, and S. Schumann, J. Chromatogr.,319, 440 (1985).Google Scholar
  30. 29.
    G. Szepesy and M. Gazdag, J. Chromatogr.,205, 57 (1981).Google Scholar
  31. 30.
    B. K. Chowdhury, S. K. Hirani, and P. Bhattacharyya, J. Chromatogr.,369, 258 (1986).Google Scholar
  32. 31.
    I. R. Hunter, M. K. Walden, and E. Heftmann, J. Chromatogr.,198, 363 (1980).Google Scholar
  33. 32.
    G. Holan, W. M. P. Johnson, and K. Rihs, J. Chromatogr.,288, 479 (1984).Google Scholar
  34. 33.
    M. Noguchi, K. Hosoda and H. Suzuki, J. Pharm. Soc. Jpn.,107, No. 5, 372 (1987).Google Scholar
  35. 33b.
    Yuyi Tong, Yaowu Fenzhi Zazhi,10, 279 (1990); Chem. Abstr.,114, 20993b (1991).Google Scholar
  36. 34.
    A. R. Hanks, L. R. Schronk, and T. C. Arnst, J. Liquid Chromatogr.,3, No. 7, 1087 (1980).Google Scholar
  37. 35.
    J. A. Saunders and D. E. Blume, J. Chromatogr.,205, 147 (1981).Google Scholar
  38. 36.
    S. Mousa, G. R. Loon, A. A. Van Houdi, and P. A. Crooks, J. Chromatogr.,347, 405 (1985).PubMedGoogle Scholar
  39. 37.
    Chen-Yie Chien, J. N. Diana, and P. A. Crooks, J. Pharm. Sci.,77, No. 3, 277 (1988).PubMedGoogle Scholar
  40. 38.
    G. N. Chiang, in: Abstracts of Papers at the Pittsburg Conference and Exposition of Analytical Chemistry and Applied Spectroscopy, Atlantic City, N.J., March 10–14, 1986, S. 1, S. A. P. 373.Google Scholar
  41. 39.
    G. Bringmann, S. Schneider, and K. D. Richter, Fresenius Z. Anal. Chem.,329, No. 4, 480 (1987).Google Scholar
  42. 40.
    M. T. Parviainen, J. Chromatogr.,432, 216 (1988).Google Scholar
  43. 41.
    D. V. McCalley, J. Chromatogr.,357, 221 (1986).Google Scholar
  44. 42.
    A. Hermans-Lokkerbol, T. Leer, and R. Verpoorte, J. Chromatogr.,479, 39 (1989).Google Scholar
  45. 43.
    M. A. Johnston, W. J. Smith, J. M. Kennedy, A. R. Lea, and D. M. Hailey, J. Chromatogr.,189, 241 (1980).Google Scholar
  46. 44.
    E. Smith, J. Chromatogr.,299, 233 (1984).PubMedGoogle Scholar
  47. 45.
    K. Mizutani and T. Yamaguchi, Iyakuhin Kenkyu,17, No. 1, 117 (1986); R. J. Ch., 13 G 276 (1986).Google Scholar
  48. 46.
    M. Montagu, P. Levillian, J. C. Chenieux, and M. Rideau, J. Chromatogr.,331, No. 2, 437 (1985).Google Scholar
  49. 47.
    B. L. Poehland, N. Troupe, B. K. Carté, and J. W. Westley, J. Chromatogr.,481, 421 (1989).Google Scholar
  50. 48.
    R. G. Peterson, B. H. Rumack, J. B. Sullivan, and A. Makowski, J. Chromatogr.,188, 420 (1980).Google Scholar
  51. 49.
    I. Válka and V. Simánek, J. Chromatogr.,455, 258 (1988).Google Scholar
  52. 50.
    J. A. Owen and D. S. Sitar, J. Chromatogr.,276, 202 (1983).PubMedGoogle Scholar
  53. 51.
    H. A. H. Billiet, R. Wolters, L. de Galan, and H. Huizer, J. Chromatogr.,368, 351 (1986).PubMedGoogle Scholar
  54. 52.
    I. Fehér, G. Szepesy, and J. Szanto, Magy. Kem. Foly.,85, No. 8, 337 (1979).Google Scholar
  55. 53.
    V. Nitsche and H. Mascher, J. Pharm. Sci.,73, No. 11, 1556 (1984).PubMedGoogle Scholar
  56. 54.
    J. Milo, A. Levy, D. Palevitch, and G. Ladizinsky, J. Chromatogr.,452, 563 (1988).Google Scholar
  57. 55.
    I. N. Paradoyannis and B. Caddy, Anal. Lett.,9, No. 9–10, 1065 (1986).Google Scholar
  58. 56.
    R. Verpoorte, J. M. Verzijl, and A. Baerheim-Svendsen, J. Chromatogr.,283, 401 (1984).Google Scholar
  59. 57.
    I. R. Tebbett, Chromatographia,23, No. 5, 377 (1987).Google Scholar
  60. 58.
    C. Kim, M. B. Speisky, and H. Kalant, J. Chromatogr.,370, 303 (1986).PubMedGoogle Scholar
  61. 59.
    Y. Hashimoto, M. I. Okada, U. Shome, and A. Kato, Anal. Lett.,19, No. 23–24, 2253 (1986).Google Scholar
  62. 60.
    A. Colautti, F. Fontani, and V. Mauricii, J. Pharm. Biochem. Anal.,5, No. 5, 493 (1987).Google Scholar
  63. 61.
    C. Y. Wu, Anal. Chem. Acta,108, 233 (1979).Google Scholar
  64. 62.
    C. Y. Wu and J. J. Wittick, Anal. Chem.,49, No. 3, 359 (1977).PubMedGoogle Scholar
  65. 63.
    J. A. Glasel and R. F. Venn, J. Chromatogr.,213, 337 (1981).Google Scholar
  66. 64.
    Y. Kumagai, T. Ishida, and S. Toki, J. Chromatogr.,421, 155 (1987).PubMedGoogle Scholar
  67. 65.
    J. J. Schneider and P. J. Ravenscroft, J. Chromatogr.,497, 326 (1989).PubMedGoogle Scholar
  68. 66.
    I. S. Lurie and S. M. Carr, J. Liquid Chromatography,9, No. 11, 2485 (1986).Google Scholar
  69. 67.
    W. Zeng, W. Liang, and G. Tu, J. Chromatogr.,408, 426 (1987).PubMedGoogle Scholar
  70. 68.
    K. M. Jensen, J. Chromatogr.,274, 381 (1983).PubMedGoogle Scholar
  71. 69.
    M. Johansson and D. Westerlund, J. Chromatogr.,452, 241 (1988).PubMedGoogle Scholar
  72. 70.
    T. Dzido, J. Chromatogr.,439, 257 (1988).Google Scholar
  73. 71.
    B. Pekic, Z. Lepjevic, B. Slavica, and S. M. Petrovic, Chromatographia,21, No. 1, 227 (1986).Google Scholar
  74. 72.
    T. Veress, Magy. Kem. Folyoikat,92, No. 2, 54 (1986).Google Scholar
  75. 73.
    W. Lindberg, E. Johansson, and K. Johansson, J. Chromatogr.,211, 201 (1981).Google Scholar
  76. 74.
    C. T. Hung, M. Young, and P. K. Gupta, J. Pharm. Sci.,77, No. 8, 719 (1988).PubMedGoogle Scholar
  77. 75.
    C. A. Turner and R. Murphy, J. Chromatogr.,428, 387 (1988).Google Scholar
  78. 76.
    S. P. Joel, R. J. Osborne, and M. L. Slevin, J. Chromatogr.,430, 394 (1988).PubMedGoogle Scholar
  79. 77.
    I. M. A. Beaumont, Anal. Proc.,19, No. 3, 128 (1982).Google Scholar
  80. 78.
    C. A. Geraghty and J. L. Cashaw, J. Chromatogr.,489, 399 (1989).PubMedGoogle Scholar
  81. 79.
    J. L. Cashaw, C. A. Geraghty, B. R. McLaughlin, and V. E. Davis, Anal. Biochem.,162, No. 1, 274 (1987).PubMedGoogle Scholar
  82. 80.
    D. A. Elvidge, G. W. Johnson, and J. R. Harrison, J. Chromatogr.,463, 107 (1989).PubMedGoogle Scholar
  83. 81a.
    M. Hutin, A. Öztekin, A. Cavé, and J. P. Foucher, J. Chromatogr.,265, 139 (1983).Google Scholar
  84. 81b.
    E. Pianezzola, V. Bellotti, E. Fontana, E. Moro, J. Gal, D. M. Desai, J. Chromatogr.,495, 205 (1989).PubMedGoogle Scholar
  85. 82.
    N. R. Ayyangar and S. R. Bhide, J. Chromatogr.,436, 455 (1988).PubMedGoogle Scholar
  86. 83.
    R. V. Smith and M. R. de Moreno, J. Chromatogr.,274, 376 (1983).PubMedGoogle Scholar
  87. 84.
    R. F. Venn and A. Michalkiewicz, J. Chromatogr.,525, 379 (1990).PubMedGoogle Scholar
  88. 85.
    N. R. Ayyangar and S. R. Bhide, J. Chromatogr.,366, 435 (1986).PubMedGoogle Scholar
  89. 86.
    J. Shah and W. D. Mason, Anal. Lett.,20, No. 6, 881 (1987).Google Scholar
  90. 87.
    J. Shah and W. D. Mason, Anal. Lett.,20, No. 9, 1493 (1987).Google Scholar
  91. 88.
    M. S. Greenberg and W. J. Mayer, J. Chromatogr.,169, 321 (1979).PubMedGoogle Scholar
  92. 89.
    H. Terada and Y. Sakabe, J. Chromatogr.,291, 453 (1984).PubMedGoogle Scholar
  93. 90.
    M. B. Kester, C. L. Saccar, M. L. Rocci, and H. C. Mansmann, J. Chromatogr.,380, 99 (1986).PubMedGoogle Scholar
  94. 91.
    N. Daoud, T. Arvidsson, and K.-G. Wahlund, J. Pharm. Biomed. Anal.,4, No. 2, 253 (1986).PubMedGoogle Scholar
  95. 92.
    N. R. Scott, J. Chakraborty, and V. Marks, J. Chromatogr.,375, 321 (1986).PubMedGoogle Scholar
  96. 93.
    S. E. O'Connell and F. J. Zurzola, J. Pharm. Sci.,73, No. 7, 1009 (1984).PubMedGoogle Scholar
  97. 94.
    D. S. Smyly, B. B. Woodward, and E. C. Conrad, J. Assoc. Offic. Anal. Chem.,59, No. 1, 14 (1976).Google Scholar
  98. 95.
    A. Lelo, D. J. Birkett, and J. O. Miners, J. Chromatogr.,430, No. 1, 203 (1988).PubMedGoogle Scholar
  99. 96.
    W. J. Hurst, K. P. Snyder, and R. A. Martin, J. Chromatogr.,318, 408 (1985).PubMedGoogle Scholar
  100. 97.
    R. Hartley, I. J. Smith, and J. R. Cookman, J. Chromatogr.,342, 105 (1985).PubMedGoogle Scholar
  101. 98.
    G. F. Kapke and R. B. Franklin, J. Liquid Chromatogr.,10, No. 2–3, 451 (1987).Google Scholar
  102. 99.
    K. J. Williams, A. Li Wan Po, and W. J. Irwin, J. Chromatogr.,194, 217 (1980).Google Scholar
  103. 100.
    B. Stavric, R. Klassen, and S. G. Gilbert, J. Chromatogr.,310, 107 (1984).PubMedGoogle Scholar
  104. 101.
    S. A. Hotchkiss and J. Caldwell, J. Chromatogr.,423, 179 (1987).PubMedGoogle Scholar
  105. 102.
    M. B. Kester, C. L. Saccar, H. C. Mansmann, J. Chromatogr.,416, 91 (1987).PubMedGoogle Scholar
  106. 103.
    J. R. Miksic and B. Hodes, J. Pharm. Sci.,68, No. 9, 1200 (1979).PubMedGoogle Scholar
  107. 104.
    S. E. Roberts and M. F. Delaney, J. Chromatogr.,242, 364 (1982).Google Scholar
  108. 105.
    S. H. Y. Wong, N. Marzouk, O. Aziz, and S. Sheeran, J. Liquid Chromatogr.,10, No. 2–3, 491 (1987).Google Scholar
  109. 106.
    K. D. R. Setchell, M. B. Welsh, M. J. Klooster, W. F. Balistreri, and C. K. Lim, J. Chromatogr.,385, 267 (1987).PubMedGoogle Scholar
  110. 107.
    J. Thomas, J. Chromatogr.,479, 430 (1989).PubMedGoogle Scholar
  111. 108.
    J. J. Lauff, J. Chromatogr.,417, 99 (1987).PubMedGoogle Scholar
  112. 109.
    J. S. Kennedy, B. W. Leduc, J. M. Scavone, J. S. Harmatz, B. I. Shader, and D. J. Greenblatt, J. Chromatogr.,422, 274 (1987).PubMedGoogle Scholar
  113. 110.
    R. Chiou, R. J. Stubbs, and W. F. Bayne, J. Chromatogr.,422, 281 (1987).PubMedGoogle Scholar
  114. 111.
    Young Han Park, C. Goshorn, and O. Hinsvark, J. Chromatogr.,343, 359 (1985).PubMedGoogle Scholar
  115. 112.
    S. Paphassarang, J. Raynaud, R. P. Godeau, and A. M. Binsard, J. Chromatogr.,319, 412 (1985).Google Scholar
  116. 113.
    F. Rogan, C. M. G. Aragon, and Z. Amit, Abstracts of Papers at the Pittsburg Conference and Exposition of Analytical and Applied Spectroscopy, New Orleans, February 25-March 1 (1985), p. 1, s.a.P. 697.Google Scholar
  117. 114.
    A. Richard and G. Andermann, Die Pharmazie,40, 802 (1985).Google Scholar
  118. 115.
    J. A. Sandberg and G. D. Olsen, J. Chromatogr.,525, 113 (1990).PubMedGoogle Scholar
  119. 116.
    Li-Yi He, Gua-De Zhang, Yu-Yi Tong, K. Sagara, T. Oshima, and T. Yoshida, J. Chromatogr.,481, 428 (1989).Google Scholar
  120. 117.
    A. Al-Shamma, S. Drake, D. L. Flynn, L. A. Mitscher, Y. H. Park, G. S. Rao, A. Simpson, J. K. Swayze, T. Veysoglu, and S. T.-S. Wu, J. Nat. Prod.,44, 745 (1981).PubMedGoogle Scholar
  121. 118.
    B. K. Chowdhury, S. K. Hirani, and D. Ngur, J. Chromatogr.,390, 439 (1987).Google Scholar
  122. 119.
    K. R. Brain and B. B. Thapa, J. Chromatogr.,258, 183 (1983).Google Scholar
  123. 120.
    K. M. Parikh, V. J. Doshi, J. B. Salunkhe, and R. P. Kamath, Indian Drugs,27, No. 1, 64 (1989).Google Scholar
  124. 121.
    L.-A. Pieters and A. J. Vlietinck, J. Liquid Chromatogr.,9, No. 4, 745 (1986).Google Scholar
  125. 122.
    G. P. Dimenna, T. P. Krick, and H. J. Segall, J. Chromatogr.,192, 474 (1980).Google Scholar
  126. 123.
    H. Niwa, H. Ishiwata, and K. Yamada, J. Chromatogr.,192, 146 (1980).Google Scholar
  127. 124.
    D. L. Dunn and R. E. Thompson, J. Chromatogr.,264, 264 (1983).Google Scholar
  128. 125.
    J. M. Kennedy and P. E. McNamara, J. Chromatogr.,212, 331 (1981).PubMedGoogle Scholar
  129. 126.
    K. Saito, K. Kobayashi, S. Ohmiya, H. Otomasu, and I. Murakoshi, J. Chromatogr.,462, 333 (1989).Google Scholar
  130. 127.
    K. Fankel and I. Slad, Fresenius' Z. Anal. Chem.,303, No. 3, 208 (1980).Google Scholar
  131. 128.
    F. Sasse, J. Hammer, and J. Berlin, J. Chromatogr.,194, 234 (1980).Google Scholar
  132. 129.
    G. Szepesy and M. Gazdag, J. Chromatogr.,204, 341 (1981).Google Scholar
  133. 130.
    G. Szepesy and I. Féher, Magy. Kem. Foly.,84, No. 8, 375 (1978).Google Scholar
  134. 131.
    A. N. Scholten and R. W. Frei, J. Chromatogr.,176, 349 (1979).PubMedGoogle Scholar
  135. 132.
    P. Pietta, A. Rava, and E. Catenacci, J. Chromatogr.,210, 149 (1981).PubMedGoogle Scholar
  136. 133.
    P. O. Edlund, J. Chromatogr.,226, 107 (1981).PubMedGoogle Scholar
  137. 134.
    J. D. Phillipson, N. Supavita, and L. A. Anderson, J. Chromatogr.,244, 91 (1981).Google Scholar
  138. 135.
    P. Perera, T. A. Van Beek, and R. Verpoorte, J. Chromatogr.,285, 214 (1984).Google Scholar
  139. 136.
    P. Spiegl and H. Viernstein, J. Chromatogr.,294, 452 (1984).Google Scholar
  140. 137.
    J. P. Chervet and D. Plas, J. Chromatogr.,295, 282 (1984).Google Scholar
  141. 138.
    B. Herényi and S. Göorög, J. Chromatogr.,238, 250 (1982).Google Scholar
  142. 139.
    S. Auriol, V.-P. Ranta, T. Naaranlahti, and S. Lapinjoki, J. Chromatogr.,474, 181 (1989).Google Scholar
  143. 140.
    R. R. Brodie, L. F. Chasseaud, and A. D. Robbins, J. Chromatogr.,415, 423 (1987).PubMedGoogle Scholar
  144. 141.
    S. W. J. Lau, D. Chow, and S. Feldman, J. Chromatogr.,526, 87 (1990).PubMedGoogle Scholar
  145. 142.
    A. Akbari, A. D. Jernigan, P. B. Bush, and N. H. Booth, J. Chromatogr.,361, 400 (1986).PubMedGoogle Scholar
  146. 143.
    C. Dubruc, H. Caqueret, and G. Bianchetti, J. Chromatogr.,204, 335 (1981).PubMedGoogle Scholar
  147. 144.
    J.-P. Renaudin, J. Chromatogr.,291, 165 (1984).Google Scholar
  148. 145.
    B. Diquet, L. Doare, and G. Gaudel, J. Chromatogr.,311, 443 (1984).Google Scholar
  149. 146.
    R. Gill and J. A. Key, J. Chromatogr.,346, 423 (1985).PubMedGoogle Scholar
  150. 147.
    P. Duez, S. Chamart, M. Vanhaelen, R. Vanhaelen-Fastré, M. Hanocq, L. Molle, J. Chromatogr.,356, 334 (1986).Google Scholar
  151. 148.
    D. Drapeau, H. W. Blanch, and C. R. Wilke, J. Chromatogr.,390, 297 (1987).PubMedGoogle Scholar
  152. 149.
    D. E. Vendrig, J. M. Holthuis, and J. Teeuwsen, J. Chromatogr.,424, 83 (1988).PubMedGoogle Scholar
  153. 150.
    D. E. Vendrig and J. M. Holthuis, TrAC: Trends Anal. Chem.,8, 141 (1989).Google Scholar
  154. 151.
    J. Moncrieff, J. Chromatogr.,496, 269 (1989).PubMedGoogle Scholar
  155. 152.
    R. Vanhaelen-Fastré, and M. Vanhaelen, J. Chromatogr.,312, 467 (1984).PubMedGoogle Scholar
  156. 153.
    R. Van der Heijden, P. J. Lamping, P. P. Out, R. Wijnsma, and R. Verpoorte, J. Chromatogr.,396, 287 (1987).Google Scholar
  157. 154.
    P. Kulanthaivel, S. W. Pelletier, J. Chromatogr.,402, 366 (1987).Google Scholar
  158. 155.
    Fuming Xie, Hongcheng Wang, Henling Shu, Jianhu Li, Jirong Jiang, Jenpin Chang, and Yuyuan Hsien, J. Chromatogr.,526, 109 (1990).PubMedGoogle Scholar
  159. 156.
    P. Bellon, P. Canal, J. Bernadou, and G. Soula, J. Chromatogr.,309, 170 (1984).PubMedGoogle Scholar
  160. 157.
    P. G. Crabbe and C. Fryer, J. Chromatogr.,187, 87 (1980).Google Scholar
  161. 158.
    S. C. Morris and T. H. Lee, J. Chromatogr.,219, 403 (1981).Google Scholar
  162. 159a.
    J. K. Reed, J. Gerrie, and K. L. Reed, J. Chromatogr.,356, 450 (1986).Google Scholar
  163. 159b.
    F. Osman and S. L. Sinden, J. Chromatogr.,479, 189 (1989).Google Scholar
  164. 160.
    H. Hikino, C. Konno, H. Watanabe, and O. Ishikawa, J. Chromatogr.,211, 123 (1981).Google Scholar
  165. 161a.
    K. Kobayashi, A. D. Powell, M. Toyoda, and Y. Saito, J. Chromatogr.,462, 357 (1989).Google Scholar
  166. 161b.
    H. Wagner, K. Seehert, H. Sonnenbichler, M. Ilyas, and K. P. Odenthal, Planta Med.,53, 444 (1987).PubMedGoogle Scholar
  167. 162.
    P. Pietta, E. Manera, and P. Ceva, J. Chromatogr.,367, 228 (1986).PubMedGoogle Scholar
  168. 163.
    J. Gal, J. Chromatogr.,307, 220 (1984).Google Scholar
  169. 164.
    A. M. Morad, I. A. Al-Meshal, F. S. El-Feraly, and K. M. Matar, J. Liquid Chromatogr.,11, No. 3, 713 (1988).Google Scholar
  170. 165.
    A. E. Klein and P. J. Davis, J. Chromatogr.,207, 247 (1981).Google Scholar
  171. 166.
    E. Lacy and R. L. Brady, J. Chromatogr.,315, 333 (1984).Google Scholar
  172. 167.
    R. J. Ko, Wen Yen Li, and R. T. Koda, J. Chromatogr.,525, 411 (1990).PubMedGoogle Scholar
  173. 168.
    Zhao Rong Chen, F. Bochner, and A. Somogyi, J. Chromatogr.,491, 367 (1989).PubMedGoogle Scholar
  174. 169.
    M. Avram and C. A. Shanks, J. Chromatogr.,306, 398 (1984).PubMedGoogle Scholar
  175. 170.
    J. Moncrieff, J. Chromatogr.,529, 194 (1990).PubMedGoogle Scholar
  176. 171.
    R. J. Bushway, J. Chromatogr.,247, 180 (1982).PubMedGoogle Scholar
  177. 172.
    K. Saito, M. Horie, Y. Hoshino, N. Nose, H. Nakazawa, J. Chromatogr.,508, 149 (1990).Google Scholar
  178. 173.
    M. Nieder and H. Jaeger, J. Chromatogr.,424, 73 (1988).PubMedGoogle Scholar
  179. 174.
    G. Bianchi and M. Landi, J. Chromatogr.,338, 230 (1985).PubMedGoogle Scholar
  180. 175.
    M. De Smet, S. P. van Belle, G. A. Storme, and D. L. Massart, J. Chromatogr.,345, 309 (1985).PubMedGoogle Scholar
  181. 176.
    M. G. Lee, J. Chromatogr.,312, 473 (1984).PubMedGoogle Scholar
  182. 177.
    M. Rathnawathie and K. A. Buckle, J. Chromatogr.,264, 316 (1983).PubMedGoogle Scholar
  183. 178.
    A. Hobson-Frohock and W. T. E. Edwards, J. Chromatogr.,249, 369 (1982).Google Scholar
  184. 179.
    L. W. Doner and An-Fei Hsu, J. Chromatogr.,253, 120 (1982).Google Scholar
  185. 180.
    M. Flieger, M. Wurst, J. Stuchlik, and Z. Rehacek, J. Chromatogr.,207, 139 (1981).Google Scholar
  186. 181.
    Y. Nobuhara, S. Hirano, K. Namba, and M. Hashimoto, J. Chromatogr.,190, 251 (1980).Google Scholar
  187. 182.
    Jian Zhang, Zhen Tian, and Zhi-Cen Lou, Planta Med.,54, 69 (1988).Google Scholar

Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • B. D. Kabulov
  • A. L. D'yakonov
  • S. V. Zalyalieva

There are no affiliations available

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