Skip to main content
Log in

Synthesis and antifungal activity of analogues of naturally occurring botrydial precursors

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

Analog compounds of the proposed intermediates of the biogenetic pathway to botrydial have been synthesized. These compounds were tested for their potential antifungal activity against the phytopathogenBotrytis cinerea. Our results showed a fungistatic effect of some compounds on mycelium growth. The most significant effect was exerted by 2-α-hydroxy-2,3-dihydro-1-epiprobotrydial, which inhibited growth ofB. cinerea. Some aspects of structure-activity relationships are discussed.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Arpin, N., Favre-Bonvin, J., andThivend, S. 1977. Structure de la mycosporine 2, nouvelle molecule, isolée deBotrytis cinerea.Tetrahedron Lett. 10:819–820.

    Article  Google Scholar 

  • Bradshaw, A.P.W., andHanson, J.R. 1980. Three new sesquiterpenoid metabolites ofBotrytis cinerea.J. Chem. Soc., Perkin I 1980:741–743.

  • Coley-Smith, J.R., Verhoeff, K., andJarvis, W.R. 1980. The Biology of Botrytis. Academic Press, London. pp 42–63.

    Google Scholar 

  • Collado, I.G., Aleu, J., Macias-Sánchez, A.J., andHernández-Galán, R. 1994. Inhibition ofBotrytis cinerea by new sesquiterpenoid compound from unusual rearrangement of isocaryophyllene.J. Nat. Prod. 57:738–746.

    Article  Google Scholar 

  • Cuevas, O., andHanson, J.R. 1977. Norbotrydial acetate, a nor-sesquiterpenoid aldehyde fromBotrytis cinerea.Phytochemistry 16:1061–1062.

    Article  Google Scholar 

  • Cutler, H.G., Springer, J.P., Arrendale, R.F., Arison, B.H., Cole, P.D., andRoberts, R.G. 1988. Cinereain: A novel metabolite with plant growth regulating properties fromBotrytis cinerea.Agric. Biol. Chem. 52:1725–1733.

    Google Scholar 

  • Fehlhaber, H.-W., Geipel, R., Mercker, H.-S., Tschesche, R., andWelmar, K. 1974. Botrydial, ein Sesquiterpen-Antibiotikum aus der Nährlösung des Pilzes Botrytis cinerea.Chem. Ber. 107:1720–1730.

    Google Scholar 

  • Gollnick, K., andSchade, G. 1970. The structure of an isocaryophyllene rearrangement product, 1,5,9,9-tetramethyl tricycle [6,2,1,04,11]undec-5-ene: X-ray analysis of the dibromo derivative.J. Chem. Soc., Chem. Commun. 1970:248–249.

  • Hanson, J.R. 1981. The biosynthesis of some sesquiterpenoids.Pure Appl. Chem. 53:1155–1162 (and references therein).

    Google Scholar 

  • Kaiser, R., andLamparsky, D. 1976. Constituents of verbena oil. Part 2. Caryophyllene 2,6-β-oxide, a new sesquiterpenoid compound from the oil ofLippia citriodora Kunth.Helv. Chim. Acta 59:1803–1808.

    Article  Google Scholar 

  • Khomenko, T.M., Bagryanskaya, I.Y., Gatilov, Y.V., Korchagina, D.V., Gatilova, V.P., Dubovenko, Z.V., andBarkhash, V.A. 1985. Molecular rearrangements of isocaryophyllene in a superacid.Zh. Org. Khim. 21:677–678.

    Google Scholar 

  • Kimata, T., Natsume, M., andMarumo, S. 1985. Botrydienal, a new phytotoxin and its related metabolites, dehydrobotrydienal and deacetyldihydrobotrydial produced byBotrytis cinerea.Tetrahedron Lett. 26:2097–2100.

    Article  Google Scholar 

  • Kimura, Y., Fujioka, H., Nakajima, H., Hamasaki, T., Irie, M., Fukuyama, K., andIsogai, A. 1986. Isolation, X-ray structure and biological activity of deacetyldihydrobotrydial produced byBotrytis squamosa.Agric. Biol. Chem. 50:2123–2135.

    Google Scholar 

  • Lindner, H.J., andGross, B.v. 1977. Die Kristall-und Molekülstruktur von Dihydrobotrydial.Chem. Ber. 107:3332–3336.

    Google Scholar 

  • Overeem, J.C., andVan Dijkman, A. 1968. Botrallin, a novel quinone produced byBotrytis alli.Recueil 87:940–944.

    Google Scholar 

  • Patil, I.S., Kulkarni, S., andHegde, R.K. 1986. Bioassay of fungicides againstDrechlera Sorokiniana (Sacc).Pesticides 1986:30–31.

    Google Scholar 

  • Suga, T., Hirata, T., Utsumi, R., andYosjioka, T. 1984. The metabolites ofBotrytis cinerea.J. Sci. Hiroshima Univ., Ser A 48:75–79.

    Google Scholar 

  • Welmar, K., Tschesche, R., andBreitmaier, E. 1979. Botrylacton, ein neuer Wirkstoff aus der Nährlösung des PilzesBotrytis cinerea, 2.Chem. Ber. 112:3598–3602.

    Google Scholar 

  • Whealer, B.E.J. 1969. An Introduction to Plant Diseases. John Wiley, London, pp. 187–188.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Collado, I.G., Aleu, J., Macías-Sánchez, A.J. et al. Synthesis and antifungal activity of analogues of naturally occurring botrydial precursors. J Chem Ecol 20, 2631–2644 (1994). https://doi.org/10.1007/BF02036197

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02036197

Key words

Navigation