Advertisement

Planta

, Volume 182, Issue 1, pp 81–88 | Cite as

Studies on the biosynthesis and metabolism of the phytoalexin lubimin and related compounds in Datura stramonium L.

  • Ian M. Whitehead
  • Anne L. Atkinson
  • David R. Threlfall
Article

Abstract

Arachidonic acid, cellulase, CuSO4, a sonicate of Phytophthora infestans mycelium and a spore suspension of Penicillium chrysogenum all elicited the formation of the sesquiterpenoid phytoalexins lubimin, 3-hydroxylubimin and rishitin in fruit cavities of Datura stramonium. 3-Hydroxylubimin was the predominant phytoalexin formed after treatment of the fruits with arachidonic acid, cellulase and the P. infestans preparation. Copper sulphate was a potent elicitor of lubimin but not 3-hydroxylubimin. The fungus P. chrysogenum metabolized lubimin and 3-hydroxylubimin to 15-dihydrolubimin and 3-hydroxy-15-dihydrolubimin respectively, both in fruit cavities inoculated with spores of this fungus and in pure culture. The 15-dihydrolubimin formed in the fruits by the fungus was further metabolized (by the fruits) to both isolubimin and 3-hydroxy-15-dihydrolubimin. The precursor-product relationships between all of the subject compounds was investigated by feeding experiments with 3H-labelled compounds. 2-Dehydro-[15-3H1]lubimin was rapidly and efficiently incorporated into lubimin and may be the direct precursor of lubimin in planta. 3-Hydroxy[2-3H1]lubimin was incorporated into the nor-eudesmane rishitin but 10-epi-3-hydroxy[2-3H1]lubimin was not. An updated scheme for the biosynthesis and metabolism of lubimin and related compounds in infected tissues of solanaceous plants is presented.

Key words

Datura Elicitor Host and fungal metabolism Lubimin 3-hydroxylase Penicillium Phytoalexin Sesquiterpenoid phytoalexins 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Rostock, R.M., Kuć, J.A. (1981) Eicosapentaenoic and arachidonic acids from Phytophthora infestans elicit fungitoxic sesquiterpenoids in the potato. Science 212, 67Google Scholar
  2. Coolbear, T., Threlfall, D.R. (1985) The biosynthesis of lubimin from [1-14C]isoopentenyl pyrophosphate by cell-free extracts of potato tuber tissue inoculated with an elicitor preparation from Phytophthora infestans. Phytochemistry 24, 1963–1971Google Scholar
  3. Desjardins, A.E., Gardner, H.W., Plattner, R.D. (1989) Detoxification of the potato phytoalexin lubimin by Gibberella pulicaris. Phytochemistry 28, 431–437Google Scholar
  4. Ewing, D.F., Whitehead, I.M., Atkinson, A.L., Threlfall, D.R. (1990) 1H NMR Study of the stereochemistry of lubimin and related vetispirane sesquiterpenoids. J. Chem. Soc. Perkin Trans. 2, 343–348Google Scholar
  5. Kalan, E.B., Osman, S.F. (1976) Isolubimin: a possible precursor of lubimin in infected potato slices. Phytochemistry 15, 775–776Google Scholar
  6. Kalan, E.B., Patterson, J.M., Schwarz, D.P. (1976) Metabolism of isolubimin and hydroxylmethyllubimin by potato tuber slices. (Abstr.) Plant Physiol. 57, Suppl., 91Google Scholar
  7. Katsui, N., Matsunaga, A., Kitakara, H., Yagihashi, F., Murai, A., Masamune, T., Sato, N. (1977) Lubimin and oxylubimin. The structure elucidation. Bull. Chem. Soc. Jpn. 50, 1217–1225Google Scholar
  8. Katsui, N., Yagihasi, F., Murai, A., Masamune, T. (1978) Structure of oxyglutinosone and epioxylubimin, stress metabolites from diseased potato tubers. Chem. Lett. 1205–1206Google Scholar
  9. Murai, A. (1987) Phytoalexin chemistry and action. In: Pesticide science and biotechnology (Proc. Int. Congr. Pestic. Chem.), p. 81, Greenhalgh, R., Roberts, T.T., eds. Blackwell, Oxford, UKGoogle Scholar
  10. Sato, K., Ishiguri, Y., Doke, N., Tomiyama, K., Yagishashi, F., Murai, A., Katsui, N., Masamune, T. (1978) Biosynthesis of the sesquiterpenoid phytoalexin rishitin from acetate via oxylubimin in potato. Phytochemistry 17, 1901–1902Google Scholar
  11. Stoessl, A., Stothers, J.B. (1980) 2-Epi and 15-dihydro-2-epi-lubimin: new stress compounds from the potato. Can. J. Chem. 58, 2069–2072Google Scholar
  12. Stoessl, A., Stothers, J.B. (1981) A carbon-13 biosynthetic study of stress metabolites from potatoes: the origin of isolubimin. Can. J. Bot. 59, 637–639Google Scholar
  13. Stoessl, A., Stothers, J.B., Ward, E.W.B. (1978) Biosynthetic studies of stress metabolites from potatoes: incorporation of sodium acetate-13C2 into 10 sesquiterpenes. Can. J. Chem. 56, 645–653Google Scholar
  14. Threlfall, D.R., Whitehead, I.M. (1988a) Co-ordinated inhibition of squalene synthetase and induction of enzymes of sesquiterpenoid phytoalexin biosynthesis in cultures of Nicotiana tabacum. Phytochemistry 27, 2567–2580Google Scholar
  15. Threlfall, D.R., Whitehead, I.M. (1988b) The use of biotic and abiotic elicitors to induce the formation of secondary plant products in cell suspension cultures of solanaceous plants. Biochem. Soc. Trans. 16, 71–75Google Scholar
  16. Threlfall, D.R., Whitehead, I.M. (1988c) The use of metals ions to induce the formation of secondary products in plant tissue culture. In: Manipulating secondary metabolism in culture, p. 51–56, R.J. Robins, M.J.C. Rhodes, eds. Cambridge University PressGoogle Scholar
  17. Tomioka, H., Takai, K., Oshima, K., Nozaki, H. (1981) Selective oxidation of a primary hydroxyl in the presence of a secondary one. Tetrahedron Lett. 22, 1605–1608Google Scholar
  18. Waldi, D. (1965) Spray reagents for thin-layer chromatography. In: Thin Layer Chromatography, p. 485, Stahl, E., ed. Springer, Berlin Heidelberg New YorkGoogle Scholar
  19. Ward, E.W.B., Stoessl, A. (1973) Postinfectional inhibitors from plants. III. Detoxification of capsidiol, an antifungal compound from peppers. Phytopathology 62, 1186–1187Google Scholar
  20. Ward, E.W.B., Stoessl, A. (1976) Phytoalexins from potatoes: evidence for the conversion of lubimin to 15-dihydrolubimin by fungi. Phytopathology 67, 468–471Google Scholar
  21. Ward, E.W.B., Unwin, C.H., Hill, J., Stoessl, A. (1976a) Sesquiterpenoid phytoalexins from fruits of eggplants. Phytopathology 65, 859–863Google Scholar
  22. Ward, E.W.B., Unwin, C.H., Rock, G.L., Stoessl, A. (1976b) Post-infectional inhibitors from plants. XXIII. Sesquiterpenoid phytoalexins from fruits capsules of Datura stramonium. Can. J. Bot. 54, 25–29Google Scholar
  23. Watson, D.G., Brooks, C.J.W. (1984) Formation of capsidiol in Capsicum annuum fruits in response to non-specific elicitors. Physiol. Plant Pathol. 24, 331–337Google Scholar
  24. Whitehead, I.M., Threlfall, D.R., Ewing, D.F. (1987) Cis-9, 10-dihydrocapsenone: a possible catabolite of capsidiol from cell suspension cultures of Capsicum annuum. Phytochemistry 26, 1367–1369Google Scholar
  25. Whitehead, I.M., Ewing, D.F., Threlfall, D.R. (1988) Sesquiterpenoids related to the phytoalexin debneyol from elicited cell suspension cultures of Nicotiana tabacum. Phytochemistry 27, 1365–1370Google Scholar
  26. Whitehead, I.M., Threlfall, D.R., Ewing, D.F. (1989a) 5-Epi-aristolochene is a common precursor of the sequiterpenoid phytoalexins capsidiol and debneyol. Phytochemistry 28, 775–779Google Scholar
  27. Whitehead, I.M., Ewing, D.F., Threlfall, D.R., Cane, D.E., Prabhakaran, P.C. (1989b) Synthesis of (+)-5-epi-aristolochene and (+)-1-deoxycapsidiol from capsidiol. Phytochemistry 29, 479–482Google Scholar

Copyright information

© Springer-Verlag 1990

Authors and Affiliations

  • Ian M. Whitehead
    • 1
  • Anne L. Atkinson
    • 1
  • David R. Threlfall
    • 1
  1. 1.Department of Applied Biology, School of Life SciencesUniversity of HullHullUK

Personalised recommendations