Skip to main content

Diterpenoid Phytoalexins: Biosynthesis and Regulation

  • Chapter
Biochemistry of the Mevalonic Acid Pathway to Terpenoids

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 24))

Abstract

Most fungal and bacterial plant pathogens can establish systemic infections in a very limited range of host plants. Thus, higher plants in general are able to resist infection by most of the fungal and bacterial phytopathogens they may encounter. In cases of general resistance during the interaction of a non-host plant with a microbial pathogen, no obvious symptoms develop in the plant. During other cases of interaction of a non-host plant, or resistant cultivars of a host plant, with a microbial pathogen, a limited necrotic lesion develops rapidly in the host plant after penetration of the microbe. This hypersensitive response is characterized by the rapid death of one or more plant cells at the site of microbial invasion, and the induction of production in still healthy plant cells immediately surrounding this site of a number of new metabolic products.1

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
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. DIXON, R.A. 1986. The phytoalexin response: elicitation, signalling and control of host gene expression. Biol. Rev. Cambridge Philos. Soc. 61:239–291.

    Article  CAS  Google Scholar 

  2. BAILEY, J.A., J. W. MANSFIELD, eds. 1982. Phytoalexins, John Wiley & Sons, New York.

    Google Scholar 

  3. BELL, J.N., T.B. RYDER, V.P.M. WINGATE, J. A. BAILEY, C. J. LAMB. 1986. Differential accumulation of plant defense gene transcripts in a compatible and an incompatible plant-pathogen interaction. Mol. Cell. Biol. 6: 1615–1623.

    PubMed  CAS  Google Scholar 

  4. PAXTON, J. D. 1981. Phytoalexins — a working redefinition. Phytopathol. Z. 101: 106–109.

    Article  Google Scholar 

  5. DIXON, R.A., P.M. DEY, C. J. LAMB 1983. Phytoalexins: enzymology and molecular biology. Adv. in Enz. and Related Area of Mol. Biol. 53: 1–126.

    Google Scholar 

  6. SWAIN, T. 1977. Secondary compounds as protective agents. Annu. Rev. Plant Physiol. 28:479–501.

    Article  CAS  Google Scholar 

  7. ROBINSON, D. R., C. A. WEST. 1970. Biosynthesis of cyclic diterpenes in extracts from seedlings of Ricinus communis L. II. Conversion of geranylgeranyl pyrophosphate into diterpene hydrocarbons and partial purification of cyclization enzymes. Biochemistry 9: 80–89.

    Article  PubMed  CAS  Google Scholar 

  8. SITTON, D., C. A. WEST. 1975. Casbene: an anti-fungal diterpene produced in cell-free extracts of Ricinus communis seedlings. Phytochemistry 14: 1921–1925.

    Article  CAS  Google Scholar 

  9. OU, S.H. 1980. Pathogen variability and host resistance in rice blast disease. Annu. Rev. Phytopathol. 18: 167–187.

    Article  Google Scholar 

  10. CARTWRIGHT, D.W., P.W. LANGCAKE, R.J. PRYCE, D.W. LEWORTHY, J.P. RIDE. 1981. Isolation and characterization of two phytoalexins from rice as momilactones A and B. Phytochemistry 20: 535–537.

    Article  CAS  Google Scholar 

  11. KATO, T., C. KABUTO, N. SASAKI, M. TSUNAGAWA, H. AIZAWA, K. FUJITA, Y. KATO, Y. KITAHARA. 1973. Momilactones, growth inhibitors from rice, Oryza sativa L. Tet. Lett. 3861–3864.

    Google Scholar 

  12. TSUNAGAWA, M., A. OHBA, N. SASAKI, C. KABUTO, T. KATO, Y. KITAHARA, N. TAKAHASHI. 1976. Momilactone C-a minor constituent of growth inhibitors in rice husk. Tet. Lett. 1157–1158.

    Google Scholar 

  13. AKATSUKA, T., O. KODAMA, H. SEKIDO, Y. KONO, S. TAKEUCHI. 1985. Novel phytoalexins (oryzalexins A, B and C) isolated from rice blast leaves infected with Pyricularia oryzae. Part I: isolation, characterization and biological activities of oryzalexins. Agrie. Biol. Chem. 49: 1689–1694.

    Article  CAS  Google Scholar 

  14. KONO, Y., S. TAKEUCHI, O. KODAMA, H. SEKIDO, T. AKATSUKA. 1985. Novel phytoalexins (oryzalexins A, B and C) from rice blast leaves infected with Pyricularia oryzae. Part II: structural studies with oryzalexins. Agric. Biol. Chem. 49: 1695–1701.

    Article  CAS  Google Scholar 

  15. KONO, Y., S. TAKEUCHI, O. KODAMA, T. AKATSUKA. 1984. Absolute configuration of oryzalexin A and structures of its related phytoalexins isolated from rice blast leaves infected with Pyricularia oryzae. Agric. Biol. Chem. 48: 253–255.

    Article  CAS  Google Scholar 

  16. SEKIDO, H., T. ENDO, R. SUGA, O. KODAMA, T. AKATSUKA, Y. KONO, S. TAKEUCHI. 1986. Oryzalexin D (3,7-dihydroxy-(+) sandaracopimaradiene), a new phytoalexin isolated from blast infected rice leaves. J. Pesticide Sci. 11: 369–372.

    Article  CAS  Google Scholar 

  17. KODAMA, O., T. SUZUKI, J. MIYAKAWA, T. AKATSUKA. 1988. Ultraviolet-induced accumulation of phytoalexins in rice leaves. Agric. Biol. Chem. 52: 2469–2473.

    Article  CAS  Google Scholar 

  18. KODAMA, O., A. YAMADA, A. YAMAMOTO, T. TAKEMOTO, T. AKATSUKA. 1988. Induction of phytoalexins with heavy metal ions in rice leaves. Nippon Noyaku Gakkaishi 13: 615–617.

    CAS  Google Scholar 

  19. DUEBER, M.T., W. ADOLF, C. A. WEST. 1978. Biosynthesis of the diterpene phytoalexin casbene. Partial purification and characterization of casbene synthetase from Ricinus communis. Plant Physiol. 62: 598–603.

    Article  PubMed  CAS  Google Scholar 

  20. DUDLEY, M. W., M. T. DUEBER, C.A. WEST. 1986. Biosynthesis of the macrocyclic diterpene in castor bean (Ricinus communis L) seedlings. Changes in enzyme levels induced by fungal infection and intracellular localization of the pathway. Plant Physiol. 81: 335–342.

    Article  PubMed  CAS  Google Scholar 

  21. GREEN, T.R., C.A. WEST. 1974. Purification and characterization of two forms of geranyl transferase from Ricinus communis. Biochemistry 13: 4720–4729.

    Article  PubMed  CAS  Google Scholar 

  22. DUDLEY, M.W., T.R. GREEN, C.A. WEST. 1986. Biosynthesis of the macrocyclic diterpene casbene in castor bean (Ricinus communis L.) seedlings. The purification and properties of farnesyl transferase from elicited seedlings. Plant Physiol. 81: 343–348.

    Article  PubMed  CAS  Google Scholar 

  23. WEST, C.A., 1981. Biosynthesis of diterpenes. Chapter 7 In: Biosynthesis of Isoprenoid Compounds. (J. W. Porter, S. L. Spurgeon, eds.), Vol. 1, John Wiley & Sons, New York. pp. 376–411.

    Google Scholar 

  24. MOESTA, P., C.A. WEST. 1985. Casbene synthetase: regulation of phytoalexin biosynthesis in Ricinus communis L. seedlings. Purification of casbene synthetase and regulation of its biosynthesis during elicitation. Arch. Biochem. Biophys. 238: 325–333.

    Article  PubMed  CAS  Google Scholar 

  25. PARGELLIS, C.A.. 1983. Studies of the prenyl transferases from organelles of Ricinus communis L. Ph.D. Dissertation, University of California, Los Angeles.

    Google Scholar 

  26. STEKOLL, M., C.A. WEST. 1978. Purification and properties of an elicitor of castor bean phytoalexin from culture filtrates of the fungus Rhizopus stolonifer. Plant Physiol. 61: 38–45.

    Article  PubMed  CAS  Google Scholar 

  27. LEE, S.C., C.A. WEST. 1981. Polygalacturonase from Rhizopus stolonifer, an elicitor of casbene synthetase activity in castor bean (Ricinus communis L.) seedlings. Plant Physiol. 67: 633–639.

    Article  PubMed  CAS  Google Scholar 

  28. LEE, S.C., C.A. WEST. 1981. Properties of Rhizopus stolonifer polygalacturonase, an elicitor of casbene synthetase activity in castor bean (Ricinus communis L.) seedlings. Plant Physiol. 67: 640–645.

    Article  PubMed  CAS  Google Scholar 

  29. BRUCE, R.J., C.A. WEST. 1982. Elicitation of casbene synthetase activity in castor bean. The role of pec-tic fragments of the plant cell wall in elicitation by a fungal endopolygalacturonase. Plant Physiol. 69: 1181–1188.

    Article  PubMed  CAS  Google Scholar 

  30. WEST, C.A., P. MOESTA, D.F. JIN, A.F. LOIS, K.A. WICKHAM. 1985. The role of pectic fragments of the plant cell wall in the response to biological stresses. In: Cellular and Molecular Biology of Plant Stress, UCLA Symposia on Molecular and Cellular Biology, New Series, Volume 22, (J.L. Key, T. Kosuge, eds.), Alan R. Liss, New York. pp. 335–349.

    Google Scholar 

  31. WALKER-SIMMONS, M., D. JIN, C.A. WEST, L. HADWIGER, C.A. RYAN. 1984. Comparison of proteinase inhibitor-inducing activities and phytoalexin elicitor activities of a pure fungal endopolygalacturonase, pectic fragments, and chitosans. Plant Physiol. 76: 833–836.

    Article  PubMed  CAS  Google Scholar 

  32. JIN, D.F., C.A. WEST. 1984. Characteristics of galacturonic acid oligomers as elicitors of casbene synthetase activity in castor bean seedlings. Plant Physiol. 74: 989–992.

    Article  PubMed  CAS  Google Scholar 

  33. LOIS, A.F. 1988. Regulation of the casbene synthetase gene during elicitation of castor bean seedlings with pectic fragments. Ph.D. Dissertation, University of California, Los Angeles.

    Google Scholar 

  34. CHAPPELL, J., K. HAHLBROCK. 1984. Transcription of plant defence genes in response to UV light or fungal elicitor. Nature 311: 76–78.

    Article  CAS  Google Scholar 

  35. LAWTON, M.A., C.J. LAMB. 1987. Transcriptional activation of plant defense genes by fungal elicitor, wounding, and infection. Mol. Cell. Biol. 7: 335–341.

    PubMed  CAS  Google Scholar 

  36. MANIARA, G., R. LAINE, J. KUC. 1984. Oligosaccharides from Phytophthora infestans enhance the elicitation of sesquiterpenoid stress metabolites by arachidonic acid in potato. Physiol. Plant Pathol. 24: 177–186.

    Article  CAS  Google Scholar 

  37. DAVIS, K.R., A.G. DARVILL, P. ALBERSHEIM. 1986. Hostpathogen interactions. XXXI. Several biotic and abiotic elicitors act synergistically in the induction of phytoalexin accumulation in soybean. Plant Mol. Biol. 6: 23–32.

    Article  CAS  Google Scholar 

  38. DAVIS, K.R., K. HAHLBROCK. 1987. Induction of defense responses in cultured parsley cells by plant cell wall fragments. Plant Physiol. 85: 1286–1290.

    Article  Google Scholar 

  39. SHECHTER, I., C.A. WEST. 1969. Biosynthesis of gibberellins. IV. Biosynthesis of cyclic diterpenes from trans-geranylgeranyl pyrophosphate. J. Biol. Chem. 244: 3200–3209.

    PubMed  CAS  Google Scholar 

  40. WICKHAM, K.A. 1988. The biosynthesis of diterpenes in rice. Ph.D. Dissertation, University of California, Los Angeles.

    Google Scholar 

  41. WICKHAM, K., C.A. WEST. 1987. Biosynthesis of diterpene phytoalexin precursors in cell-free extracts of rice. In: The Metabolism, Structure and Function of Plant Lipids. (P.K. Stumpf, J. B. Mudd, W.D. Nes, eds.), Plenum Publishing Corp., New York. pp. 123–125.

    Google Scholar 

  42. MATSUYAMA, N., S. WAKIMOTO. 1985. Purification and characterization of anti-blast substance, S-1, formed mainly in blast-resistant lower rice leaves. Ann. Phytopath. Soc. Japan 51: 498–500.

    Article  CAS  Google Scholar 

  43. MATSUYAMA, N., S. WAKIMOTO. 1988. Isolation and identification of diterpenoid anti-blast substances produced in the blast-infected rice leaves. Nippon Shokubutsu Byori Gakkaiho 54: 183–188.

    CAS  Google Scholar 

  44. FROST, R.G., C.A. WEST. 1977. Properties of kaurene synthetase from Marah macrocarpus. Plant Physiol. 59: 22–29.

    Article  PubMed  CAS  Google Scholar 

  45. DUEBER, M.T. 1979. Studies of phytoalexin biosynthesis in castor beans: purification and characterization of casbene synthetase. Ph.D. Dissertation, University of California, Los Angeles.

    Google Scholar 

  46. DARVILL, A.G., P. ALBERSHEIM. 1984. Phytoalexins and their elicitors—a defense against microbial infection in plants. Annu. Rev. Plant Physiol. 35: 243–275.

    Article  CAS  Google Scholar 

  47. BARBER, M.S., J.P. RIDE. 1988. A quantitative test for induced lignification in wounded wheat leaves and its use to survey potential elicitors of the response. Physiol. Mol. Plant Pathol. 32: 185–197.

    Article  CAS  Google Scholar 

  48. KUROSAKI, F., M. AMIN, A. NISHI. 1986. Induction of phytoalexin production and accumulation of phenolic compounds in cultured carrot cells. Physiol. Mol. Plant Pathol. 28: 359–370.

    Article  CAS  Google Scholar 

  49. ROBY D., A. GADELLE, A. TOPPAN. 1987. Chitin oligosac-charides as elicitors of chitinase activity in melon. Biochem. Biophys. Res. Commun. 143: 885–892.

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1990 Plenum Press, New York

About this chapter

Cite this chapter

West, C.A., Lois, A.F., Wickham, K.A., Ren, YY. (1990). Diterpenoid Phytoalexins: Biosynthesis and Regulation. In: Towers, G.H.N., Stafford, H.A. (eds) Biochemistry of the Mevalonic Acid Pathway to Terpenoids. Recent Advances in Phytochemistry, vol 24. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-8789-3_6

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-8789-3_6

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-8791-6

  • Online ISBN: 978-1-4684-8789-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics