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Biosynthesis of marine sterols

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Marine Natural Products — Diversity and Biosynthesis

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 167))

Abstract

Marine sterols have been the subject of intense research since Bergmann first discovered that marine organisms elaborate unique sterols. Much of this research has been directed at the isolation and characterization of novel marine sterols, but recently studies have begun to investigate their biosynthetic origin. The study of an organism and its ability to perform de novo sterol biosynthesis, as well as its metabolic processes such as alkylation, dealkylation, and rearrangement, has provided insight into sterol sequestration and utilization. These efforts to understand the biosynthetic origin of marine sterols are reviewed.

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7 References

  1. Nes WK, McKean ML (1977) Biochemistry of steroids and other isopentanoids, University Park, Baltimore

    Google Scholar 

  2. Kerr RG, Baker BJ (1991) Nat Prod Rep 8:465 and cited references

    Article  Google Scholar 

  3. Goad LJ (1978) In: Scheuer PJ (Ed.) Marine natural products, chemical and biological perspectives, vol 2, Academic, New York, chap 2

    Google Scholar 

  4. Goad LJ (1981) Pure Appl Chem 51:837

    Google Scholar 

  5. Ikekawa N (1985) In: Danielsson H, Sjovall J (eds) Sterols and bile acids, Elsevier, Amsterdam, chap 8

    Google Scholar 

  6. Djerassi C, Silva CJ (1991) Acct Chem Res 24:371

    Article  Google Scholar 

  7. Carlson RMK, Tarchini C, Djerassi C (1980) In: Ananchenko SN (ed) Frontiers in bioorganic chemistry and molecular biology, p 211

    Google Scholar 

  8. Djerassi C, Lam W-K (1991) Accts Chem Res 24:69

    Article  Google Scholar 

  9. D'Auria MV, Paloma LG, Minale L, Riccio R (1991) Tetrahedron Lett 2149

    Google Scholar 

  10. Lawson MP, Stoilov IL, Thompson JE, Djerassi C (1988) Lipids 23:750

    PubMed  Google Scholar 

  11. Herbert RB (1989) The biosynthesis of secondary metabolites, 2nd edn, Chapman and Hall, New York

    Google Scholar 

  12. Voogt PA (1976) Nether J Zoo 26:84

    Google Scholar 

  13. Silva CJ, Wunsche L, Djerassi C (1991) Comp Biochem Physiol 99B:763

    Article  Google Scholar 

  14. De Rosa M, Minale L, Sodano G (1975) Experientia 31:758

    Article  PubMed  Google Scholar 

  15. Cordeiro ML, Djerassi C (1990) J Org Chem 55:2806

    Article  Google Scholar 

  16. Walton MJ, Pennock JF (1972) Biochem J 127:471

    PubMed  Google Scholar 

  17. Ferezou JP, Devys M, Allais JP, Barbier M (1974) Phytochem 13:593

    Article  Google Scholar 

  18. Voogt PA (1975) Comp Biochem Physiol 50B:505

    Article  Google Scholar 

  19. Teshima S, Kanazawa A (1974) Comp Biochem Physiol 47B:555

    Article  Google Scholar 

  20. Beastall GH, Rees HH, Goodwin TW (1971) FEBS Lett 18:175

    Article  PubMed  Google Scholar 

  21. Giner J-L, Wunsche L, Andersen RA, Djerassi C (1991) Biochem Syst Ecol 19:143

    Article  Google Scholar 

  22. Cordeiro ML, Kerr RG, Djerassi C (1988) Tetrahedron Lett 2159

    Google Scholar 

  23. De Rosa M, Minale L, Sodano G (1973) Comp Biochem Physiol 45B:883

    Google Scholar 

  24. Minale L, Ricco R, Scalano O, Fattorusso E, Magno S, Mayol L, Santacroce C (1977) Experientia 33:1550

    Article  PubMed  Google Scholar 

  25. Kerr RG, Stoilov IL, Thompson JE, Djerassi C (1989) Tetrahedron 45:1893

    Article  Google Scholar 

  26. Silva CJ, Wunsche L, Djerassi C (1991) Comp Biochem Physiol 99B:763

    Article  Google Scholar 

  27. Stoilov IL, Bladocha-Moreau M, Thompson JE, Djerassi C (1987) Tetrahedron 43:1987

    Article  Google Scholar 

  28. John V, Stoilov IL, Djerassi C, Karuso P, Poiner A, Scheuer PJ (1989) J Org Chem 54:1642

    Article  Google Scholar 

  29. De Rosa M, Minale L, Sodano G (1976) Experientia 32:1112

    Article  Google Scholar 

  30. Garson MJ, Partali V, Liaaen-Jensen S, Stoilov IL (1988) Comp Biochem Physiol 91B:293

    Google Scholar 

  31. Biblino L, Minale L, Sodano G (1978) J Chem Soc Chem Commun 524

    Google Scholar 

  32. De Stefano A, Sodano G (1980) Experientia 36:630

    Article  Google Scholar 

  33. Malik S, Stoilov IL, Djerassi C (1988) Tetrahedron Lett 4081

    Google Scholar 

  34. Rabinowitz MH, Djerassi C (1992) J Am Chem Soc 114:304

    Article  Google Scholar 

  35. Papov S, Carlson RMK, Wegmann A-M, Djerassi C (1976) Tetrahedron Lett 3491

    Google Scholar 

  36. Bortolotto M, Braekman JC, Daloze D, Losman D, Tursch B (1976) Steroids 28:461.

    Article  PubMed  Google Scholar 

  37. Kashman Y, Carmely S (1980) Tetrahedron Lett 4939

    Google Scholar 

  38. Catalan CAN, Thompson JE, Kokke WCMC, Djerassi C (1985) Tetrahedron 41:1073

    Article  Google Scholar 

  39. Stoilov IL, Thompson JE, Djerassi C (1986) Tetrahedron 42:4147

    Article  Google Scholar 

  40. Stoilov IL, Back TG, Thompson JE, Djerassi C (1986) Tetrahedron 42:4156

    Article  Google Scholar 

  41. Djerassi C, Theobald T, Kokke WCMC, Pak CS, Carlson RMK (1979) Pure Appl Chem 51:1815

    Google Scholar 

  42. Djerassi C (1981) Pure Appl Chem 53:873

    Google Scholar 

  43. Li LN, Sjostrand U, Djerassi C (1981) J Org Chem 46:3867

    Article  Google Scholar 

  44. Gebreyesus TG, Stoilov IL, Luo F-T, Djerassi C (1985) Steroids 45:447

    Article  PubMed  Google Scholar 

  45. Stoilov IL, Thompson JE, Cho J-H, Djerassi C (1986) J Am Chem Soc 108:8235

    Article  Google Scholar 

  46. Li LN, Sjostrand U, Djerassi C (1981) J Am Chem Soc 103:115

    Article  Google Scholar 

  47. Kerr RG, Kerr SL, Djerassi C (1991) J Org Chem 56:63

    Article  Google Scholar 

  48. Kerr RG, Kerr SL, Pettit GR, Herald DL, Groy TL, Djerassi C (1991) J Org Chem 56:58

    Article  Google Scholar 

  49. Malik S, Kerr RG, Djerassi C (1988) J Am Chem Soc 110:6895

    Article  Google Scholar 

  50. Kerr RG, Kerr SL, Malik S, Djerassi C (1992) J Am Chem Soc 114:299

    Article  Google Scholar 

  51. Kerr RG, Baker BJ, Kerr SL, Djerassi C (1990) Tetrahedron Lett 5425

    Google Scholar 

  52. Svoboda JA (1984) In: Nes WD, Fuller G, Tsai L, (eds) Isopentenoids in plants, Marcel Dekker, New York, p 367

    Google Scholar 

  53. Khalil MW, Idler DR (1976) Comp Biochem Physiol 55B:239

    Article  Google Scholar 

  54. Djerassi C, Doss GA (1991) In: Rahman A (ed) Studies in Natural Products Chemistry, Vol. 9, Elsevier, Amsterdam, p 35

    Google Scholar 

  55. Bergmann W, McLean MJ, Lester D (1943) J Org Chem 8:271

    Article  Google Scholar 

  56. Hale RL, Leclercq J, Tursch B, Djerassi C, Gross RA, Westheimer AJ, Gupta KC, Scheuer PJ (1970) J Am Chem Soc 92:2179

    Article  Google Scholar 

  57. Ling NC, Hale RL, Djerassi C (1970) J Am Chem Soc 92:5281

    Article  PubMed  Google Scholar 

  58. Ciereszko LS (1991) Biol Ocean 6:363

    Google Scholar 

  59. Ciereszko LS, Johnson MAW, Schmidt RW, Koons CB (1968) Comp Biochem Physiol 24B:899

    Article  PubMed  Google Scholar 

  60. Kerr RG, Southgate P (1992) Comp Biochem Physiol B in press

    Google Scholar 

  61. Giner J-L, Djerassi C (1991) J Org Chem 56:2357

    Article  Google Scholar 

  62. Sica D, Zollo F (1978) Tetrahedron Lett 837

    Google Scholar 

  63. Cho J-H, Djerassi C (1987) J Chem Soc Perkin Trans 1 1307

    Article  Google Scholar 

  64. Ravi BN, Kokke WCMC, Delseth C, Djerassi C (1978) Tetrahedron Lett 4379

    Google Scholar 

  65. Doss GA, Proudfoot JR, Silva CJ, Djerassi C (1990) J Am Chem Soc 112:305

    Article  Google Scholar 

  66. Djerassi C, Theobald T, Kokke WCMC, Pak CS, Carlson RMK (1979) Pure Appl Chem 51:1815

    Google Scholar 

  67. Fattorusso E, Magno S, Mayol L, Santacroce C, Sica D (1975) Tetrahedron 31:1715

    Article  Google Scholar 

  68. Li LN, Li J-T, Lang RW, Itoh T, Sica D, Djerassi C (1982) J Am Chem Soc 104:6726

    Article  Google Scholar 

  69. Margot C, Catalan CAN, Proudfoot JR, Sodano G, Sica D, Djerassi C (1987) J Chem Soc Chem Commun 1441

    Google Scholar 

  70. Doss GA, Djerassi C (1988) J Am Chem Soc 110:8124

    Article  Google Scholar 

  71. Khalil MW, Durham LJ, Djerassi C, Sica D (1980) J Am Chem Soc 102:2133

    Article  Google Scholar 

  72. Shu AYL, Djerassi C (1987) J Chem Soc Perkin Trans 1 1291

    Article  Google Scholar 

  73. Cho J-H, Djerassi C (1987) J Chem Soc Perkin Trans 1 1307

    Article  Google Scholar 

  74. Bonini C, Kinnel RB, Scheuer PJ, Djerassi C (1983) Tetrahedron Lett 277

    Google Scholar 

  75. Kobayashi M, Mitsuhashi H (1982) Steroids 40:665

    Article  PubMed  Google Scholar 

  76. Catalan CAN, Lakshami V, Schmitz FJ, Djerassi C (1982) Steroids 40:455

    Article  PubMed  Google Scholar 

  77. Kerr RG, Kerr SL (unpublished results)

    Google Scholar 

  78. Catalan CAN, Djerassi C (1983) Tetrahedron Lett 3461

    Google Scholar 

  79. Gurst JE, Sheikh YM, Djerassi C (1973) J Am Chem Soc 95:628

    Article  PubMed  Google Scholar 

  80. Ballantine JA, Williams K, Burke BA (1977) Tetrahedron Lett 1547

    Google Scholar 

  81. Delseth C, Carlson RMK, Djerassi C, Erdman TR, Scheuer PJ (1978) Helv Chim Acta 61:1470

    Article  Google Scholar 

  82. Prinsep MR, Blunt JW, Munro M (1989) J Nat Prod 52:657

    Article  Google Scholar 

  83. Bandurraga MM, Fenical W (1985) Tetrahedron 41:1057

    Article  Google Scholar 

  84. Higgs MD, Faulkner DJ (1977) Steroids 30:379

    Article  PubMed  Google Scholar 

  85. Kingston JF, Gregory B, Fallis AG (1979) J Chem Soc Perkin Trans 1 2064

    Article  Google Scholar 

  86. Ross RA, Scheuer PJ (1979) Tetrahedron Lett 4701

    Google Scholar 

  87. Sheikh YM, Tursch BM, Djerassi C (1972) J Am Chem Soc 94:3278

    Article  PubMed  Google Scholar 

  88. ApSimon JW, Buccini JA, Badripersand S (1973) Can J Chem 51:850

    Google Scholar 

  89. Ikegami S, Kamiya Y, Tamura S (1972) Tetrahedron Lett 1661

    Google Scholar 

  90. Kerr RG, Schulman AL (1992) 1992 Annual Meeting — Florida Sections, American Chemical Society, April 30-May 2, 1992, abstract 19

    Google Scholar 

  91. Schoenmakers HJN (1979) Comp Biochem Physio 63B:179

    Article  Google Scholar 

  92. Voogt PA, Den Besten PJ, Jansen M (1990) Comp Biochem Physiol 97B:555

    Google Scholar 

  93. Garson MJ (1989) Nat Prod Rep 6:143

    Article  Google Scholar 

  94. Withers N (1983) In: Scheuer PJ (ed) Marine natural products, chemical and biological perspectives, vol 5, Academic, New York, chap 3

    Google Scholar 

  95. Tymiak AA, Rinehart KL (1981) J Am Chem Soc 103:6763

    Article  Google Scholar 

  96. Hagadone MR, Scheuer PJ, Holm A (1986) J Am Chem Soc 106:2447

    Article  Google Scholar 

  97. Barnett D, Dean PW, Hart RJ, Lucas JS, Salathe R, Howden MEH (1988) Comp Biochem Physiol 90B:141

    Google Scholar 

  98. Avila C, Ballesteros M, Cimino G, Crispino A, Gavagnin M, Sodano G (1990) Comp Biochem Physiol 97B:363

    Google Scholar 

  99. Giner J-L, Djerassi C (1990) Tetrahedron Lett 5421

    Google Scholar 

  100. Voogt PA, Van Rheenen JWA, Lambert JGD, de Groot BF, Mollema C (1986) Comp Biochem Physiol 84B:397

    Google Scholar 

  101. Voogt PA, Van Rheenen JWA (1986) Comp Biochem Physiol 85B:497

    Article  Google Scholar 

  102. Anderson DG (1985) Comp Biochem Physiol 81B:423

    Google Scholar 

  103. Saliot A, Barbier M (1973) J Exp Mar Bio Ecol 13:207

    Article  Google Scholar 

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Author information

Authors and Affiliations

  1. Department of Chemistry, Florida Institute of Technology, 150 W. University Blvd., 32901, Melbourne, FL, USA

    Bill J. Baker

  2. Department of Chemistry, Florida Atlantic University, 33431, Boca Raton, FL, USA

    Russell G. Kerr

Authors
  1. Bill J. Baker
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  2. Russell G. Kerr
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Paul J. Scheuer

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© 1993 Springer-Verlag

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Baker, B.J., Kerr, R.G. (1993). Biosynthesis of marine sterols. In: Scheuer, P.J. (eds) Marine Natural Products — Diversity and Biosynthesis. Topics in Current Chemistry, vol 167. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0034369

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  • DOI: https://doi.org/10.1007/BFb0034369

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  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-540-56513-0

  • Online ISBN: 978-3-540-47576-7

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