Skip to main content

Abstract

The polyketides form a group of metabolites which are based on patterns of repeating acetate units (Chapter 3). There is another group of metabolites, widespread in nature and rich in diverse chemistry, which is based on another repeating unit: isoprene (4.1).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 16.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Natural Substances Formed Biologically from Mevalonic Acid, (1970), (ed. T. W. Goodwin) Academic Press, New York.

    Google Scholar 

  2. Goodwin, T. W. (1971), in Rodd’s Chemistry of Carbon Compounds, 2nd Ed. (ed. S. Coffey), vol. HE, pp. 54–137.

    Google Scholar 

  3. Goodwin, T. W. (1974), in Rodd’s Chemistry of Carbon Compounds, vol. II Supplement, pp. 237–89.

    Google Scholar 

  4. Hanson, J. R. (1979), in Comprehensive Organic Chemistry (ed. D. H. R. Barton and W. D. Ollis ), Pergamon, Oxford, vol. 5, pp. 989–1023.

    Google Scholar 

  5. Britton, G. (1979), in Comprehensive Organic Chemistry (ed. D. H. R. Barton and W. D. Ollis ), Pergamon, Oxford, vol. 5, pp. 1025–42.

    Google Scholar 

  6. Ruzicka, L. (1959), Proc. Chem. Soc., 341–60.

    Google Scholar 

  7. Tavormina, P. A. and Gibbs, M. H. (1956), J. Amer. Chem. Soc., 78, 6210.

    Article  Google Scholar 

  8. Cornforth, J. W. and Cornforth, R. H. (1970), in Natural Substances Formed Biologically from Mevalonic Acid (ed. T. W. Goodwin), Academic Press, New York, pp. 5–15.

    Google Scholar 

  9. Retey, J., von Stetten, E., Coy, U. and Lynen, F. (1970), Eur. J. Biochem., 15, 72–6.

    Article  Google Scholar 

  10. Popjak, G. and Cornforth, J. W. (1966), Biochem. J., 101, 553–68.

    Google Scholar 

  11. Clayton, R. B. (1965), Quart, Rev. Chem. Soc., 19, 168 - 230.

    Article  Google Scholar 

  12. Mulheim, L.J. and Ramm, P.J. (1972), Chem. Soc. Rev., 1, 259–91.

    Article  Google Scholar 

  13. Goad, L. J. (1970), in Natural Substances Formed Biologically from Mevalonic Acid (ed. T. W. Goodwin), Academic Press, New York, pp. 45–77.

    Google Scholar 

  14. Woodward, R. B. and Bloch, K. (1953), J. Amer. Chem. Soc., 75, 2023–4.

    Article  Google Scholar 

  15. Cornforth, J. W., Gore, I. and Popják, G. (1957), Biochem. J., 65, 94–109.

    Google Scholar 

  16. Popják, G., Edmond, J., Anet, F. A. L. and Easton, N. R. jun.,(1977), J Amer. Chem. Soc., 99, 931–5.

    Article  Google Scholar 

  17. Schechter, I. and Bloch, K. (1971), J. Biol. Chem., 246, 7690 - 6.

    Google Scholar 

  18. Methods in Enzymology (1969), (ed. R. B. Clayton), Academic Press, New York, vol. 15.

    Google Scholar 

  19. van Tamelen, E. E., Willet, J. D., Clayton, R. B. and Lord, K. E. (1966), J. Amer. Chem. Soc., 88, 4752–4.

    Article  Google Scholar 

  20. Corey, E. J., Russey, W. E., Ortiz de Montellano, P. R. (1966), J Amer. Chem. Soc., 88, 4750–1.

    Article  Google Scholar 

  21. van Tamelen, E. E. and Hopla, R. E. (1979), J. Amer. Chem. Soc., 101, 6112–4.

    Article  Google Scholar 

  22. Barton, D. H. R., Mellows, G., Widdowson, D. A. and Wright, J. J. (1971),J Chem. Soc. (C), 1142–8.

    Google Scholar 

  23. Cornforth, J. W., Cornforth, R. H., Pelter, A., Horning, M. G. and Popják, G. (1959), Tetrahedron, 5, 311–39.

    Article  Google Scholar 

  24. Mandgal, R. K., Tchen, T. T. and Bloch, K. (1958), J Amer. Chem. Soc., 80, 2589–90.

    Article  Google Scholar 

  25. Clifford, K. H. and Phillips, G. T. (1976), Eur. J. Biochem., 61, 271–86.

    Article  Google Scholar 

  26. Miller, W. L. and Gaylor, J. L. (1970), J. Biol. Chem., 245, 5375–81.

    Google Scholar 

  27. Hornby, G. M. and Boyd, G. S. (1970), Biochem. Biophys. Res. Comm., 40, 1452–4.

    Article  Google Scholar 

  28. Alexander, K., Akhtar, M., Boar, R. B., McGhie, J. F. and Barton, D. H. R. (1972),J Chem. Soc. Chem. Comm., 383–5.

    Google Scholar 

  29. Caspi, E., Ramm, P. J. and Gain, R. E. (1969), J. Amer. Chem. Soc., 91, 4012–3.

    Article  Google Scholar 

  30. Ramm, P.J. and Caspi, E. (1969), J. Biol. Chem., 244, 6064–73.

    Google Scholar 

  31. Aberhart, D.J. and Caspi, E. (1971), J Biol. Chem., 246, 1387–92.

    Google Scholar 

  32. Wilton, D. C. and Akhtar, M. (1970), Biochem. J., 116, 337–9.

    Google Scholar 

  33. Sih, C. J, and Whitlock, H. W. jun., (1968), Ann. Rev. Biochem., 37, 661–94.

    Article  Google Scholar 

  34. Georghiu, P. E. (1977), Chem. Soc. Rev., 6, 83–107.

    Article  Google Scholar 

  35. de Luca, H. F. and Schnoes, H. K. (1976), Ann. Rev. Biochem., 45, 631–66.

    Article  Google Scholar 

  36. Rees, H. H. and Goodwin, T. W. (1974), Biochem. Soc. Trans., 2, 1027–32.

    Google Scholar 

  37. Barton, D. H. R., Corrie, J. E. T., Marshall, P. J. and Widdowson, D. A. (1973), Bio-org. Chem., 2, 363–73.

    Google Scholar 

  38. Altman, L. J., Han, C. Y., Bertolino, A., Handy, G., Laungani, D., Muller, W., Schwatz, S., Shanker, D., de Wolf, W. H. and Yang, F. ( 1978, J. Amer. Chem. Soc., 100, 3235–7.

    Article  Google Scholar 

  39. Goad, L.J. and Goodwin, T. W. (1972), Progr. Phytochem., 3, 113 - 98.

    Google Scholar 

  40. Knights, B. A. (1973), Chem. Brit., 9, 106–11.

    Google Scholar 

  41. Bimpson, T., Goad, L.J. and Goodwin, T. W. (1969), Chem. Comm., 297–8.

    Google Scholar 

  42. Caspi, E. and Hornby, G. M. (1968), Phytochemistry, 7, 423–7.

    Article  Google Scholar 

  43. Tschesche, R., Hulpke, H. and Fritz, R. (1968), Phytochemistry, 7, 2021–6.

    Article  Google Scholar 

  44. Tschesche, R. and Spindler, M. (1978), Photochemistry, 17, 251–5.

    Article  Google Scholar 

  45. Herbert, R. B. (1979), in The Alkaloids (Specialist Periodical Reports), (ed. M. F. Grundon), The Chemical Society, London, vol. 9, pp. 27–8; and earlier volumes in this series.

    Google Scholar 

  46. Seo, S., Tomita, Y. and Tori, K. (1975), J Chem. Soc. Chem. Comm., 270–1.

    Google Scholar 

  47. Rees, H. H, Britton, G. and Goodwin, T. W. (1968), Biochem. J., 106, 659–65.

    Google Scholar 

  48. Barton, D. H. R., Jarman, T. R., Watson, K. G., Widdowson, D. A., Boar, R. B. and Damps, K. (1974), J. Chem. Soc. Chem. Comm., 861–2.

    Google Scholar 

  49. Caspi, E., Zander, J. M, Greig, J. B., Mallory, F. B, Conner, R. L. and Landrey, J. B. (1968), J Amer. Chem. Soc., 90, 3563–4.

    Article  Google Scholar 

  50. Caspi, E., Greig, J. B. and Zander, J. M. (1968), J Biol. Chem., 109, 931–2.

    Google Scholar 

  51. Barton, D. H. R., Gosden, A. F., Mellows, G. and Widdowson, D. A. (1969), Chem. Comm., 185–6.

    Google Scholar 

  52. Arigoni, D. (1958), Experientia, 14, 153–5.

    Article  Google Scholar 

  53. Ruzicka, L. (1963), Pure Appl. Chem., 6, 493–523.

    Article  Google Scholar 

  54. Clifford, K., Cornforth, J. W., Mallaby, R. and Phillips, G. T. (1971), J. Chem. Soc. Chem. Comm., 1599–600.

    Google Scholar 

  55. Cornforth, J. W. (1969), Quart. Rev. Chem. Soc., 23, 125–40.

    Article  Google Scholar 

  56. Beytia, E., Qureshi, A. A. and Porter, J. W. (1973), J Biol. Chem., 248, 1856–67.

    Google Scholar 

  57. Muscio, F., Carlson, J. P, Kuehl, L. and Rilling, H. C. (1974), J. Biol. Chem., 249, 3746–9.

    Google Scholar 

  58. Popják, G., Ngan, H.-L. and Agnew, W. (1975), Bio-org. Chem., 4, 279–89.

    Google Scholar 

  59. Ortiz de Montellano, P. R., Castillo, R., Vinson, W. and Wei, J. S. (1976), J Amer. Chem. Soc., 98, 3020–1.

    Article  Google Scholar 

  60. Altman, L. J., Kowerski, R. C. and Laungani, D. P. (1978), J Amer. Chem. Soc., 100, 6174–82.

    Article  Google Scholar 

  61. Rilling, H. C., Poulter, C. D., Epstein, W. W. and Larsen, B. (1971), J. Amer. Chem. Soc., 93, 1783–5.

    Article  Google Scholar 

  62. van Tamelen, E. E. and Schwartz, M. A. (1971),J Amer. Chem. Soc., pp. 1780–2.

    Google Scholar 

  63. Cornforth, J. W. (1973), Chem. Soc. Rev., 2, 1–20.

    Article  Google Scholar 

  64. Banthorpe, D. V., Charlwood, B. V. and Francis, M. J. O. (1972), Chem. Rev., 72, 115–49.

    Article  Google Scholar 

  65. Croteau, R., Burbott, A. J. and Loomis, W. D. (1973), Biochem. Biophys. Res. Comm., 50, 1006–12.

    Article  Google Scholar 

  66. Arigoni, D. (1975), Pure Appl. Chem., 41, 219–45.

    Article  Google Scholar 

  67. Banthorpe, D. V. and Ekundayo, O. (1976), Phytochemistry, 15, 109–12.

    Article  Google Scholar 

  68. Banthorpe, D. V., Doonan, S. and Gutowski, J. A. (1977), Phytochemistry, 16, 85–92.

    Article  Google Scholar 

  69. Pattenden, G., Popplestone, C. R. and Storer, R. (1975),J Chem. Soc. Chem. Comm., 290–1.

    Google Scholar 

  70. Murray, M. J. and Hefendehl, F. W. (1973), Phytochemistry, 12, 1875–80.

    Article  Google Scholar 

  71. Yeowell, D. A. and Schmid, H. (1964), Experientia, 20, 250–2.

    Article  Google Scholar 

  72. Cordell, G. A. (1976), Chem. Rev., 76, 425–60.

    Article  Google Scholar 

  73. Evans, R. and Hanson, J. R. (1976),J Chem. Soc. Perkin I, 326–9.

    Google Scholar 

  74. Milborrow, B. V. (1975), Phytochemistry, 14, 123–8.

    Article  Google Scholar 

  75. Morikawa, K., Hirose, Y. and Nozoe, S. (1971), Tetrahedron Lett., 1131–2.

    Google Scholar 

  76. Ballesia, F., Grandi, R., Marchesini, A., Pagnoni, U. M. and Trave, R. (1975), Phytochemistry, 14, 1737–40.

    Article  Google Scholar 

  77. Croteau, R. and Loomis, W. D. (1972), Phytochemistry, 11, 1055–66.

    Article  Google Scholar 

  78. Soucek, M. (1962), Coll. Czech. Chem. Comm., 27, 2929–33.

    Google Scholar 

  79. Baker, F. C. and Brooks, C. J. W. (1976), Phytochemistry, 15, 689–94.

    Article  Google Scholar 

  80. Overton, K. H. and Picken, D.J. (1976),J. Chem. Soc. Chem. Comm., 105–6.

    Google Scholar 

  81. Birnbaum, G. I., Huber, C. P., Post, M. L, Stothers, J. B., Robinson, J. R., Stoessl, A. and Ward, E. W. B. (1976), J. Chem. Soc. Chem. Comm., 330–1.

    Google Scholar 

  82. Cane, D. E. and Levin, R. H. (1976), J. Amer. Chem. Soc., 98, 1183–8.

    Article  Google Scholar 

  83. Canonica, L., Kroszczynski, W., Ranzi, B. M., Rindone, B. and Scolastico, C. (1971), J. Chem. Soc. Chem. Comm., 257

    Google Scholar 

  84. Bedford, C. T., Fairlie, J. C., Knittel, P., Money, T. and Phillips, G. T. (1971), J. Chem. Soc. Chem. Comm., pp. 323–4.

    Google Scholar 

  85. Corbella, S, Gariboldi, P., Jommi, G. and Sisti, M. (1975), J. Chem. Soc. Chem. Comm., 288–9.

    Google Scholar 

  86. Biollaz, M. and Arigoni, D. (1969),J Chem. Soc. Chem. Comm., 633–4.

    Google Scholar 

  87. Corbella, A., Gariboldi, P., Jommi, G. and Scolastico, C. (1969), J. Chem. Soc. Chem. Comm., 634–5.

    Google Scholar 

  88. Edwards, O. E., Douglas, J. L. and Mootoo, B. (1970), Can. J. Chem., 48, 2517–24.

    Article  Google Scholar 

  89. Dorn, F., Bernasconi, P. and Arigoni, D. (1975), Chimia (Switz.), 29, 24–5.

    Google Scholar 

  90. Hanson, J. R. and Nyfeler, R. (1975), J. Chem. Soc. Chem. Comm., 824–5.

    Google Scholar 

  91. Tanabe, M., Suzuki, K. T. and Jankowski, W. C. (1974), Tetrahedron Lett., 2271–4.

    Google Scholar 

  92. Hanson, J. R., Marten, T. and Nyfeler, R. (1976), J. Chem. Soc. Perkin I, 876–80.

    Google Scholar 

  93. Mellows, G, Mantle, P. G., Feline, T. C. and Williams, D.J. (1973), Phytochemistry, 12, 2717–20.

    Article  Google Scholar 

  94. Hikino, H., Miyase, T. and Takemoto, T. (1976), Phytochemistry, 15, 121–3.

    Article  Google Scholar 

  95. Evans, R., Hanson, J. R. and Marten, T. (1976), J. Chem. Soc. Perkin I, 1212–4.

    Google Scholar 

  96. Heinstein, P. F., Herman, D. L., Tove, S. B. and Smith, F. H. (1970), J Biol. Chem., 245, 4658–65.

    Google Scholar 

  97. Banerji, A., Jones, R. B., Mellows, G., Phillips, L. and Sim, K.-Y. (1976), J. Chem. Soc. Perkin. I, 2221–8.

    Google Scholar 

  98. Banerji, A., Hunter, R., Mellows, G., Sim, K. and Barton, D. H. R. (1978), J. Chem. Soc. Chem. Comm., 843–5.

    Google Scholar 

  99. Adams, M. R. and Bu’Lock, J. D. (1975), J. Chem. Soc. Chem. Comm., 389–91.

    Google Scholar 

  100. Polonsky, J., Lukacs, G., Cagnoli-Bellavita, N. and Ceccherelli, P. (1975), Tetrahedron Lett., 481–4.

    Google Scholar 

  101. Achilladelis, B. and Hanson, J. R. (1969), J. Chem. Soc. (C). 2010–4.

    Google Scholar 

  102. Arigoni, D. (1968), Pure Appl Chem., 17, 331–48.

    Article  Google Scholar 

  103. Cross, B. E. (1968), Progress in Phytochem., 1, 195–222.

    Google Scholar 

  104. Graebe, J. E., Hedden, P. and MacMillan, J. (1975),J Chem. Soc. Chem. Comm., 161–3.

    Google Scholar 

  105. Dawson, R. M., Jeffries, P. R. and Knox, J. R. (1975), Phytochemistry, 14, 2593–7.

    Article  Google Scholar 

  106. Evans, R. and Hanson, J. R. (1975),J Chem. Soc. Perkin I, 633–6.

    Google Scholar 

  107. Cordell, G. A. (1974), Phytochemistry, 13, 2343–64.

    Article  Google Scholar 

  108. Goodwin, T. W. (1979), Pure Appl. Chem., 51, 593–6.

    Article  Google Scholar 

  109. Goodwin, T. W. (1972), Biochem. Soc. Symp., 35, 233–44.

    Google Scholar 

  110. McDermott, J. C. B., Britton, G. and Goodwin, T. W. (1973), Biochem. J., 134, 1115–7.

    Google Scholar 

  111. Britton, G., Lockley, W. J. S., Patel, N. J., Goodwin, T. W. and Englert, G. (1977),J Chem. Soc. Chem. Comm., 655–6.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1981 R. B. Herbert

About this chapter

Cite this chapter

Herbert, R.B. (1981). Terpenes and steroids. In: The Biosynthesis of Secondary Metabolites. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-5833-3_4

Download citation

  • DOI: https://doi.org/10.1007/978-94-009-5833-3_4

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-009-5835-7

  • Online ISBN: 978-94-009-5833-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics