Advertisement

Sterol Biosynthesis

  • John D. Weete
Part of the Monographs in Lipid Research book series (MLR)

Abstract

Since the structure of cholesterol was determined in the 1930’s, a large volume of material has been published concerning its biosynthesis. These studies have been reviewed on several occasions.(1–12) As in many other areas of biochemistry, progress was greatly facilitated with the development of 14C-labeled substrates and the chemical synthesis of stereospecifically labeled mevalonic acid enabled even greater advances in the area of sterol biosynthesis. Most of these studies were primarily concerned with the formation of cholesterol by animal systems, and only relatively recently has interest developed in sterol biosynthesis by plants and fungi. The first part of this chapter deals with the formation of squalene and its cyclization to lanosterol, while the latter part is concerned with the biosynthesis of ergosterol by fungi in comparison with sterol formation in plants and animals.

Keywords

Mevalonic Acid Sterol Biosynthesis Fungal Product Isopentenyl Pyrophosphate Fungal System 
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.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    T. W. Goodwin, Biochem. J. 123: 293 (1971).PubMedGoogle Scholar
  2. 2.
    L. J. Goad, in Terpenoids in Plants, ( J. B. Pridham, ed.), Academic Press, New York (1967).Google Scholar
  3. 3.
    E. Heftmann and E. Moseltig, Biochemistry of Steroids, Reinhold Publishing Corp., New York (1960).Google Scholar
  4. 4.
    I. O. Frantz and G. J. Schroepfer, Ann. Rev. Biochem. 36: 691 (1967).PubMedGoogle Scholar
  5. 5.
    G. Popjak and J. W. Cornforth, Biochem. J. 101: 553 (1966).PubMedGoogle Scholar
  6. 6.
    K. Bloch, Science 150: 19 (1965).PubMedGoogle Scholar
  7. 7.
    R. C. Ottke, E. L. Tatum, I. Zakin, and K. Bloch, J. Biol. Chem. 189: 429 (1951).PubMedGoogle Scholar
  8. 8.
    G. E. W. Wolstenholme and M. O’Connor (eds.) Ciba Foundation Symposium on the Biosynthesis of Terpenes and Sterols, Little, Brown and Co., Boston (1959).Google Scholar
  9. 9.
    J. W. Cornforth, J. Lipid Res. 1: 3 (1959).Google Scholar
  10. 10.
    G. Popjak and J. W. Cornforth, in Advances in Enzymology, Vol. 22, p. 281 ( F. F. Nord, ed. ), Interscience, (1960).Google Scholar
  11. 11.
    K. Bloch, Harvey Lectures 48: 68 (1952).PubMedGoogle Scholar
  12. 12.
    R. B. Clayton, Quart. Rev. 19: 168 (1965).Google Scholar
  13. 13.
    K. Folkers, C. H. Skunk, B. O. Linn, F. M. Robinson, P. E. Wittreich, J. W. Huff, J. L. Gilfillan, and H. R. Skeggs, in Biosynthesis of Terpenes and Sterols, Little, Brown and Co., Boston (1959).Google Scholar
  14. 14.
    J. D. Brodie, G. Wasson, and J. W. Porter, J. Biol. Chem. 238: 1294 (1963).PubMedGoogle Scholar
  15. 15.
    B. H. Amdur, H. C. Rilling, and K. Bloch, J. Amer. Chem. Soc. 79: 2646 (1957).Google Scholar
  16. 16.
    T. T. Tchen, J. Amer. Chem. Soc. 79: 6344 (1957).Google Scholar
  17. 17.
    T. T. Tchen, J. Biol. Chem. 233: 1100 (1958).PubMedGoogle Scholar
  18. 18.
    K. Bloch, S. Chaykin, A. H. Phillips, and A. DeWaard, J. Biol. Chem. 234: 2595 (1959).PubMedGoogle Scholar
  19. 19.
    B. W. Agranoff, H. Eggerer, U. Henning, and F. Lynen, J. Biol. Chem. 235: 326 (1960).PubMedGoogle Scholar
  20. 20.
    J. W. Cornforth, K. Clifford, R. Mallaby, and G. T. Phillips, Proc. Roy. Soc. (London) Ser. B 182: 277 (1972).Google Scholar
  21. 21.
    G. Popjak, Biochem. Soc. London Symp. 29: 17 (1970).Google Scholar
  22. 22.
    G. Popjak and J. W. Cornforth, Biochem. J. 101: 553 (1966).PubMedGoogle Scholar
  23. 23.
    J. W. Cornforth, R. H. Cornforth, C. Donninger, and G. Popjak, Proc. Roy. Soc. (London) Ser. B 163: 492 (1966).Google Scholar
  24. 24.
    F. Lynen, H. Eggerer, U. Henning, and I. Kessel, Angew. Chem. 70: 738 (1958).Google Scholar
  25. 25.
    F. Lynen, B. W. Agranoff, H. Eggerer, U. Henning, and E. M. Möslein, Angew. Chem. 71: 657 (1959).Google Scholar
  26. 26.
    B. H. Amdur, H. C. Rilling, and K. Bloch, J. Am. Chem. Soc. 79: 2646 (1957).Google Scholar
  27. 27.
    F. Lynen, H. Eggerer, and U. Henning, Angew. Chem. 70: 638 (1958).Google Scholar
  28. 28.
    H. C. Rilling, J. Biol. Chem. 241: 3233 (1966).PubMedGoogle Scholar
  29. 29.
    W. W. Epstein and H. C. Rilling, J. Biol. Chem. 245: 4597 (1970).PubMedGoogle Scholar
  30. 30.
    L. J. Altman, R. C. Kowerski, and H. C. Rilling, J. Am. Chem. Soc. 93: 1782 (1971).PubMedGoogle Scholar
  31. 31.
    I. Shechter and K. Bloch, J. Biol. Chem. 246: 7690 (1971).PubMedGoogle Scholar
  32. 32.
    I. M. Heilbron, E. D. Kamm, and W. M. Owens, J. Chem. Soc. 1630 (1926).Google Scholar
  33. 33.
    H. J. Channon, Biochem. J. 20: 400 (1926).PubMedGoogle Scholar
  34. 34.
    R. G. Langdon and K. Bloch, J. Biol. Chem. 200: 129 (1953).PubMedGoogle Scholar
  35. 35.
    R. B. Woodward and K. Bloch, J. Am. Chem. Soc. 75: 2023 (1953).Google Scholar
  36. 36.
    E. J. Corey and W. E. Russey, J. Am. Chem. Soc. 88: 4751 (1966).PubMedGoogle Scholar
  37. 37.
    E. J. Corey and W. E. Russey, J. Am. Chem. Soc. 88: 4750 (1966).Google Scholar
  38. 38.
    E. E. van Tamelin, J. D. Willet, R. B. Clayton, and K. E. Lord, J. Am. Chem. Soc. 88: 4752 (1966).Google Scholar
  39. 39.
    P. Benveniste and R. A. Massey-Westropp, Tetrahedron Letters 37: 3553 (1967).Google Scholar
  40. 40.
    L. J. Mulheirn and E. Caspi, J. Biol. Chem. 246: 3948 (1971).PubMedGoogle Scholar
  41. 41.
    J. Shechter, F. W. Sweat, and K. Bloch, Biochem. Biophys. Acta 220: 463 (1970).PubMedGoogle Scholar
  42. 42.
    P. D. G. Dean, P. R. Ortiz de Montellano, K. Bloch, and E. J. Corey, J. Biol. Chem. 242: 3014 (1967).PubMedGoogle Scholar
  43. 43.
    E. I. Mercer and M. W. Johnson, Phytochemistry 8: 2329 (1969).Google Scholar
  44. 44.
    M. von Ardenne, G. Osske, K. Schreiber, K. Steinfelder, and R. Tummler, Kulturpflanze 13: 102 (1965).Google Scholar
  45. 45.
    P. Benveniste, L. Hirth, G. Ourisson, and C. R. Seances, Acad. Agr. Franc. 259: 2284 (1964).Google Scholar
  46. 46.
    L. J. Goad and T. W. Goodwin, Biochem. J. 99: 735 (1966).PubMedGoogle Scholar
  47. 47.
    G. Ponsinet and G. Ourisson, Bull. Soc. Chem. Franc. 3682 (1965).Google Scholar
  48. 48.
    H. Wieland and W. M. Stanley, Ann. Chem. 489: 31 (1931).Google Scholar
  49. 49.
    H. Wieland, H. Pasedach, and A. Ballauf, Ann. Chem. 529: 68 (1937).Google Scholar
  50. 50.
    L. Ruzicka, R. Denss, and O. Jeger, Heir. Chim. Acta 28: 759 (1945).Google Scholar
  51. 51.
    L. Ruzicka, R. Denss, and O. Jeger, Held. Chim. Acta 29: 204 (1946).Google Scholar
  52. 52.
    R. S. Ludwiczak and U. Wrzeciono, Roczniki Chem. 34: 77 (1960).Google Scholar
  53. 53.
    G. Goulston, L. J. Goad, T. W. Goodwin, Biochem. J. 102: 15C (1967).PubMedGoogle Scholar
  54. 54.
    E. Schwenk, G. J. Alexander, C. A. Fish, and T. H. Stoudt, Federation Proc. 14: 752 (1955).Google Scholar
  55. 55.
    E. Kodicek, in CIBA Foundation Symposium on the Biosynthesis of Terpenes and Sterols, p. 173, Churchill, London (1959).Google Scholar
  56. 56.
    E. Schwenk and G. J. Alexander, Arch. Biochem. Biophys. 76: 65 (1958).PubMedGoogle Scholar
  57. 57.
    L. Ruzicka, Experimentia 9: 357 (1953).Google Scholar
  58. 58.
    L. Ruzicka, Proc. Chem. Soc. 341 (1959).Google Scholar
  59. 59.
    R. K. Mudgal, T. T. Tchen, and K. Bloch, J. Am. Chem. Soc. 80: 2589 (1958).Google Scholar
  60. 60.
    J. W. Cornforth, R. H. Cornforth, A. Peter, M. G. Horning, and G. Popjak, Tetrahedron Letters 5: 311 (1959).Google Scholar
  61. 61.
    J. W. Cornforth, R. H. Cornforth, C. Donninger, G. Popjak, Y. Shimizu, S. Ichii, E. Forchielli, and E. Caspi, J. Am. Chem. Soc. 87: 3224 (1965).PubMedGoogle Scholar
  62. 62.
    L. J. Goad and T. W. Goodwin, European J. Biochem. 7: 502 (1969).Google Scholar
  63. 63.
    H. H. Rees, L. J. Goad, and T. W. Goodwin, Biochem. J. 107: 417 (1968).PubMedGoogle Scholar
  64. 64.
    J. D. Weete, Phytochemistry 12: 1843 (1973).Google Scholar
  65. 65.
    J. A. Olsen, Jr., M. Lindberg, and K. Bloch, J. Biol. Chem. 226: 941 (1957).Google Scholar
  66. 66.
    K. Bloch, Science 150: 19 (1965).PubMedGoogle Scholar
  67. 67.
    W. L. Miller, M. E. Kalafer, J. L. Gaylor, and C. V. Delwiche, Biochemistry 6: 2673 (1967).PubMedGoogle Scholar
  68. 68.
    J. A. Olsen, Jr., Ergeb. Physiol. Biol. Chem. Exp. Pharmakol. 56: 173 (1965).Google Scholar
  69. 69.
    R. B. Clayton, Quart. Rey. Biol. 19: 168 (1965).Google Scholar
  70. 70.
    J. L. Gaylor, J. Biol. Chem. 239: 756 (1964).PubMedGoogle Scholar
  71. 71.
    W. L. Miller, D. R. Brady, and J. L. Gaylor, J. Biol. Chem. 246: 5147 (1971).PubMedGoogle Scholar
  72. 72.
    J. T. Moore and J. L. Gaylor, Arch. Biochem. Biophvs. 424: 167 (1968).Google Scholar
  73. 73.
    R. Rahman, K. B. Sharpless, T. A. Spencer, and R. B. Clayton, J. Biol. Chem. 245: 2667 (1970).PubMedGoogle Scholar
  74. 74.
    K. B. Sharpless. T. E. Snyder. T. A. Spencer, K. K. Makeshwari, G. Guhn. and R. B. Clayton, J. Am. Chem. Soc. 90: 6874 (1968).Google Scholar
  75. 75.
    K. B. Sharpless, T. E. Snyder. T. A. Spencer, K. K. Makeshwari, J. A. Nelson, and R. B. Clayton, J. Am. Chem. Soc. 91: 3394 (1969).PubMedGoogle Scholar
  76. 76.
    E. L. Ghisalberti, N. J. DeSouza, H. H. Rees, L. J. Goad, and T. W. Goodwin, Chem. Commun. 1403 (1969).Google Scholar
  77. 77.
    M. Lindberg, F. Gautshi, and K. Bloch, J. Biol. Chem. 238: 1661 (1963).PubMedGoogle Scholar
  78. 78.
    K. Bloch, in CIBA Foundation Symposium of Biosynthesis of Terpenes and Sterols ( G. E. W. Wolstenholme and M. O’Connor, eds.). p. 4. Little Brown Company. Boston (1959).Google Scholar
  79. 79.
    A. C. Sumdell and J. L. Gaylor, J. Biol. Chem. 243: 5546 (1968).Google Scholar
  80. 80.
    A. D. Rahimtula and J. L. Gaylor, J. Biol. Chem. 247: 9 (1972).PubMedGoogle Scholar
  81. 81.
    G. J. Schroepfer, Jr.. B. N. Lutsky, J. A. Martin, S. Huntoon, B. Fourcans, W. H. Lee, and J. Vermition, Proc. Roy. Soc. (London) Ser. B 18013: 113 (1972).Google Scholar
  82. 82.
    W. L. Miller and J. L. Gaylor, J. Biol. Chem. 245: 5369 (1970).PubMedGoogle Scholar
  83. 83.
    W. L. Miller and J. L. Gaylor, J. Biol. Chem. 245: 5375 (1970).PubMedGoogle Scholar
  84. 84.
    G. M. Hornby and G. S. Boyd, Biochem. Biophrs. Res. Commun. 40: 1452 (1970).Google Scholar
  85. 85.
    F. Gautschi and K. Bloch, J. Am. Chem. Soc. 79: 684 (1957).Google Scholar
  86. 86.
    F. Gautschi and K. Bloch, J. Biol. Chem. 233: 1343 (1958).PubMedGoogle Scholar
  87. 87.
    J. A. Gustafsson and P. Eneroth, Proc. Roy. Soc. (London) 180: 179 (1972).Google Scholar
  88. 88.
    J. C. Knight, P. D. Klein, and P. A. Szczepanik, J. Biol. Chem. Ser. B 241: 1502 (1966).Google Scholar
  89. 89.
    D. H. R. Barton, D. M. Harrison, and D. A. Widdowson, Chem. Commun. 17 (1968).Google Scholar
  90. 90.
    P. J. Doyle, G. W. Patterson, S. R. Dutky, and C. F. Cohen, Phytochemistry 10: 2093 (1971).Google Scholar
  91. 91.
    K. Alexander. M. Akhtar, R. B. Board. J. F. McGhie, and D. H. R. Barton, Chem. Commun. 383 (1972).Google Scholar
  92. 92.
    L. Canonica, A. Fiecchi, M. G. Kienle, A. Scala, G. Galli, E. G. Paoletti, and R. Paoletti, J. Am. Chem. Soc. 90: 3597 (1968).PubMedGoogle Scholar
  93. 93.
    M. Akhtar, I. A. Watkinson, A. D. Rahimtula, D. C. Wilton, and K. A. Munday, Chem. Commun. 1406 (1968).Google Scholar
  94. 94.
    M. Akhtar, A. D. Rahimtula, I. A. Watkinson, D. C. Wilton, and K. A. Munday, European J. Biochem. 9: 107 (1969).Google Scholar
  95. 95.
    G. F. Gibbons, L. J. Goad, and T. W. Goodwin, Chem. Commun. 1458 (1968).Google Scholar
  96. 96.
    O. Berseus, Acta Chem. Scand. 19: 325 (1965).PubMedGoogle Scholar
  97. 97.
    L. G. Dickson and G. W. Patterson, Lipids 7: 635 (1972).Google Scholar
  98. 98.
    M. Akhtar, W. A. Brooks, I. A. Watkinson, Biochem. J. 115: 135 (1969).PubMedGoogle Scholar
  99. 99.
    D. J. Frost and J. P. Ward, Rec. Tray. Chim. 89: 1054 (1970).Google Scholar
  100. 100.
    J. D. Weete, J. L. Laseter. and G. C. Lawler, Arch. Biochem. Biopltys. 155: 411 (1973).Google Scholar
  101. 101.
    D. H. R. Barton and T. Bruun, J. Chem. Soc. 2728 (1951).Google Scholar
  102. 102.
    K. A. Mitropoulos and N. B. Myant, Biochem. J. 97: 26C (1965).PubMedGoogle Scholar
  103. 103.
    J. Avigan, D. S. Goodman, and D. Steinberg, J. Biol. Chem. 238: 1283 (1963).PubMedGoogle Scholar
  104. 104.
    J. L. Gaylor, Arch. Biochem. Biophvs. 101: 108 (1963).Google Scholar
  105. 105.
    D. J. Hanahan and S. J. Wakil, J. Am. Chem. Soc. 75: 273 (1953).Google Scholar
  106. 106.
    G. J. Alexander and E. Schwenk, J. Am. Chem. Soc. 79: 4554 (1957).Google Scholar
  107. 107.
    G. J. Alexander and J. Schwenk, J. Biol. Chem. 232: 611 (1958).PubMedGoogle Scholar
  108. 108.
    G. T. Alexander, A. M. Gold, and E. Schwenk, J. Am. Chem. Soc. 79: 2967 (1957).Google Scholar
  109. 109.
    G. T. Alexander, A. M. Gold, and E. Schwenk, J. Biol. Chem. 232: 599 (1958).PubMedGoogle Scholar
  110. 110.
    L. W. Parks, J. Am. Chem. Soc. 80: 2023 (1958).Google Scholar
  111. 111.
    J. R. Turner and L. W. Parks, Biochem. Biophvs. Acta 98: 394 (1965).Google Scholar
  112. 112.
    J. T. Moore Jr. and J. L. Gaylor, J. Biol. Chem. 244: 6334 (1969).PubMedGoogle Scholar
  113. 113.
    R. T. Van Aller, H. Chikamatsu, N.J. DeSouza, J. P. John, and W. R. Nes, J. Biol. Chem. 244: 6645 (1969).PubMedGoogle Scholar
  114. 114.
    E. Lederer, Biochem. J. 93: 449 (1964).PubMedGoogle Scholar
  115. 115.
    E. Lederer, Q. Res. Chem. Soc. 23: 453 (1969).Google Scholar
  116. 116.
    G. Jaurequiberry, J. H. Law, J. McCloskey, and E. Lederer, Biochemistry 4: 347 (1965).Google Scholar
  117. 117.
    M. Akhtar, M. A. Parvez, and P. F. Hunt, Biochem. J. 100: 38C (1966).PubMedGoogle Scholar
  118. 118.
    D. H. R. Barton, D. M. Harrison, and G. P. Moss, Chem. Commun. 595 (1966).Google Scholar
  119. 119.
    Y. Tornita, A. Yomori, and H. Minato, Phytochemistry 9: 555 (1970).Google Scholar
  120. 120.
    M. Castle, G. Blondin, and W. R. Nes, J. Am. Chem. Soc. 85: 3306 (1963).Google Scholar
  121. 121.
    S. Bader, L. Guglialmetti, and D. Arigoni, Proc. Chem. Soc. 16: (1964).Google Scholar
  122. V. R. Villanueva, M. Barbier, and E. Lederer, Bull. Soc. Chim. France 1423: (1964).Google Scholar
  123. 123.
    J. R. Lenton, J. Hall, A. R. H. Smith, E. L. Ghisalberti, H. H. Rees, L. J. Goad, and T. W. Goodwin, Arch. Biochem. Biophys. 143: 664 (1971).PubMedGoogle Scholar
  124. 124.
    M. Lenfant, E. Zissmann, and E. Lederer, Tetrahedron Letters 12: 1049 (1967).PubMedGoogle Scholar
  125. 125.
    K. H. Raab, N. J. DeSouza, and W. R. Nes, Biochem. Biophvs. Acta 152: 742 (1968).Google Scholar
  126. 126.
    L. J. Goad and T. W. Goodwin, Biochem. J. 96: 79P (1965).Google Scholar
  127. 127.
    L. J. Goad and T. W. Goodwin, European J. Biochem. 7: 502 (1969).Google Scholar
  128. 128.
    K. J. Stone and F. W. Hemming, Biochem. J. 96: 14C (1965).PubMedGoogle Scholar
  129. 129.
    H. Katsuki and K. Bloch, J. Biol. Chem. 242: 222 (1967).PubMedGoogle Scholar
  130. 130.
    M. Akhtar, M. A. Parvez, and P. F. Hunt, Biochem. J. 113: 727 (1969).PubMedGoogle Scholar
  131. 131.
    C. W. Shoppee, in Chemistry of the Steroids, Butterworths, London (1964).Google Scholar
  132. 132.
    P. Beveniste, M. J. E. Hewlins, and B. Fritig, European J. Biochem. 9: 526 (1969).Google Scholar
  133. 133.
    L. W. Parks, F. T. Bond, E. D. Thompson, and P. R. Starr, J. Lipid Res. 13: 311 (1972).PubMedGoogle Scholar
  134. 134.
    L. Canonica, A. Fiecchi, M. G. Kienle, A. Scala, G. Galli, E. G. Paoletti, and R. Paoletti, Steroids 11: 749 (1968).PubMedGoogle Scholar
  135. 135.
    L. Canonica, A. Fiecchi, M. G. Kienle, A. Scala, G. Galli, E. G. Paoletti, and R. Paoletti, Steroids 12: 445 (1969).Google Scholar
  136. 136.
    E. Caspi, J. B. Greig, P. J. Ramm, and K. R. Varma, Tetrahedron Letters No. 35 3829 (1968).Google Scholar
  137. 137.
    G. F. Gibbons, L. J. Goad, and T. W. Goodwin, Chem. Commun. 1212 (1968).Google Scholar
  138. 138.
    E. Caspi and P. J. Ramm, Tetrahedron Letters 3: 181 (1969).Google Scholar
  139. 139.
    G. W. Patterson and E. P. Karlander, Plant. Physiol. 42: 1651 (1967).PubMedGoogle Scholar
  140. 140.
    G. W. Patterson and E. P. Karlander, Plant. Physiol. Suppl. S-43: 46 (1968).Google Scholar
  141. 141.
    I. D. Frantz, Jr., A. G. Davison, E. Dulit, and M. L. Mobberly, J. Biol. Chem. 234: 2290 (1959).PubMedGoogle Scholar
  142. 142.
    T. J. Scallen and M. W. Schuster, Steroids 12: 683 (1968).PubMedGoogle Scholar
  143. 143.
    L. J. Goad, G. F. Gibbons, L. Lolger, H. H. Rees, and T. W. Goodwin, Biochem. J. 96: 79 (1969).Google Scholar
  144. 144.
    M. Akhtar and S. Marsh, Biochem. J. 102: 462 (1967).PubMedGoogle Scholar
  145. 145.
    A. M. Paliokas and G. J. Schroepfer, Biochem. Biophvs. Res. Commun. 26: 736 (1967).Google Scholar
  146. 146.
    A. M. Paliokas and G. J. Schroepfer, J. Biol. Chem. 243: 453 (1968).PubMedGoogle Scholar
  147. 147.
    M. Akhtar and M. A. Parvez, Biochem. J. 108: 527 (1968).PubMedGoogle Scholar
  148. 148.
    S. M. Dewhurst and M. Akhtar, Biochem. J. 105: 1187 (1967).PubMedGoogle Scholar
  149. 149.
    T. Bimpson, L. J. Goad, and T. W. Goodwin, Chem. Commun. 297 (1969).Google Scholar
  150. 150.
    R. W. Topham and J. L. Gaylor, Biochem. Biophys. Res. Commun. 27: 644 (1967).PubMedGoogle Scholar
  151. 151.
    R. W. Topham and J. L. Gaylor, J. Biol. Chem. 245: 2319 (1970).PubMedGoogle Scholar
  152. 152.
    R. W. Topham and J. L. Gaylor, Biochem. Biophys. Res. Commun. 47: 180 (1972).PubMedGoogle Scholar
  153. 153.
    J. G. Hamilton and R. N. Castrejon, Federation Proc. 25: 221 (1966).Google Scholar
  154. 154.
    J. M. Zander and E. Caspi, J. Biol. Chem. 245: 1682 (1970).PubMedGoogle Scholar
  155. 155.
    T. Bimpson, Ph.D. Thesis, University of Liverpool, Liverpool, England (1970).Google Scholar
  156. 156.
    A. R. H. Smith, L. J. Goad, and T. W. Goodwin, Chem. Commun. 926 (1968).Google Scholar
  157. 157.
    A. R. H. Smith, L. J. Goad, and T. W. Goodwin, Chem. Commun. 1259 (1968).Google Scholar
  158. 158.
    W. B. Turner, in Fungal Metabolites, Academic Press, New York (1971).Google Scholar
  159. 159.
    G. W. Patterson, Lipids 6: 120 (1971).Google Scholar
  160. 160.
    W. R. Nes, Lipids 6: 219 (1971).PubMedGoogle Scholar
  161. 161.
    C. J. Alexopoulos, Introductor Mycology, 2nd edition, John Wiley & Sons, New York (1962).Google Scholar
  162. 162.
    G. W. Martin, in The Fungi, Vol. 3 (G. C. Ainsworth and A. S. Sussman, eds.), p. 635, Academic Press, New York (1968).Google Scholar
  163. 163.
    R. F. Cain, Mycologia 64: 1 (1972).Google Scholar
  164. 164.
    G. F. Gibbins, L. J. Goad, T. W. Goodwin and W. R. Nes, J. Biol. Chem. 246: 3967 (1967).Google Scholar
  165. 165.
    S. Bartnicki-Garcia, in Phytochentical Phylogeny ( J. B. Harborne, ed.), p. 81, Academic Press, New York (1970).Google Scholar
  166. 166.
    H. K. Adam, I. M. Cambell, and N. J. McCorkendale, Nature 216: 367 (1967).Google Scholar

Copyright information

© Plenum Press, New York 1974

Authors and Affiliations

  • John D. Weete
    • 1
  1. 1.Department of Botany and MicrobiologyAuburn UniversityAuburnUSA

Personalised recommendations