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Journal of Chemical Ecology

, Volume 11, Issue 2, pp 251–263 | Cite as

A multichemical defense mechanism of bitter oliveOlea europaea (oleaceae)

Is oleuropein a phytoalexin precursor?
  • Isao Kubo
  • Akiko Matsumoto
  • Ichiro Takase
Article

Abstract

Olea europaea (Oleaceae) is resistant in nature to insect and microbe attack. Two types of chemical protection were found in the foliage. One type is the bitterseco-iridoid glycosides oleuropein (1) and ligstroside (2); The other is a physical barrier of crystalline oleanolic acid (4) that coats the leaf surface. Theseco-iridoid glycosides were isolated using two different countercurrent chromatographies: rotation locular countercurrent chromatography (RLCC) and droplet countercurrent chromatography (DCCC). The dimethyl ester (III) was shown to be an artifact. This is the first isolation of ligstroside fromO. europaea. In an antimicrobial test by the paper disk method againstBacillus subtilis, Saccharomyces cerevisiae, andEscherichia coli, compounds I, II, and III inhibited a growth ofB. subtilis at pH 7. Similar tests under the influence of β-glucosidase suggest an aglycone of oleuropein, either the hemiacetal (i) or the possible enal-aldehyde (ii), could be the active intermediate. This intermediate could be produced rapidly in response to microorganism invasion. Oleuropein producing such a postinfection active intermediate could be referred to as a phytoalexin precursor.

Key words

Olea europaea (Oleaceae) oleuropein ligstroside oleanolic acid rotation locular countercurrent chromatography (RLCC) droplet countercurrent chromatography (DCCC) chemical barrier multichemical defense mechanism enal-aldehyde active intermediate phytoalexin precursor 

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References

  1. Asaka, Y., Kamikawa, T., Kubota, T., andSakamoto, H. 1972. Structures of seco-iridoids fromLigstrum obtusifolium Steb. et Zucc.Chem. Lett. 00:141–144.Google Scholar
  2. Cruess, W.V., andAlsberg, C.L. 1934. The bitter glucoside of the olive.J. Am. Chem. Soc. 56:2115–2117.Google Scholar
  3. Fleming, H.P., Walter, W.M., Jr., andEtchells, J.L. 1973. Antimicrobial properties of oleuropein and products of its hydrolysis from green olives.Appl. Microbiol. 26:777–782.PubMedGoogle Scholar
  4. Hostettmann, K. 1980. Droplet countercurrent chromatography and its application to the preparative scale separation of natural products.Planta Med. 39:1–18.Google Scholar
  5. Indue, H., Yoshida, T., Tobita, S., Tanaka, K., andNishioka, T. 1970. Absolute Struktur des Oleuropeins und einiger verwandter Glucoside.Tetrhaderon Lett. 29:2459–2464.Google Scholar
  6. Kubo, I. andMatsumoto, A., 1984. Secreted oleanolic acid on the cuticle ofOlea europaea (Oleaceae); a chemical barrier to fungus attack.Experientia. 40:937–938.Google Scholar
  7. Kubo, I., Klocke, J.A., Ganjian, I., Ichikawa, N., andMatsumoto, T. 1983. Efficient isolation of phytoecdysones fromAjuga plants by high-performance liquid chromatography and droplet countercurrent chromatography.J. Chromatogr. 257:157–161.Google Scholar
  8. Kubo, I., Matsumoto, T., andKlocke, J.A. 1984. Multichemical resistances of the coniferPodocarpus gracilior (Podocarpaceae) to insect attack.J. Chem. Ecol. 10:547–559.Google Scholar
  9. Panizzi, L., Scarpati, M.L., andOriente, G. 1960. Constituzione della oleuropeina, glucoside amaro e ad azione iptensiva dell'olivo.Gazz. Chim. Ital. 90:1449–1485.Google Scholar
  10. Romualda, C., Pietro, M., andLucio, P. 1974. Triterpenes in husks ofOlea europaea.Phytochemistry 13:1551–1552.Google Scholar
  11. Roncero, A.V., andJaner, M.L. 1969. Acidos triterpenicos del olivo.Grasas Aceites 20:133–138.Google Scholar
  12. Sticher, O. 1969. Iridoide.Pharm. Acta Helv. 44:453.PubMedGoogle Scholar
  13. Taniguchi, M., Adachi, T., Haraguchi, H., Oi, S., andKubo, I. 1983. Physiological activity of warburganal and its reactivity with sulfhydryl groups.J. Bochem. 94:149–154.Google Scholar
  14. Walter, W.M. Jr., Fleming, H.P., andEtchelis, J.L. 1973. Preparation of antimicrobial compounds by hydrolysis of oleuropein from green olives.Appl. Microbiol. 26:773–776.PubMedGoogle Scholar

Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • Isao Kubo
    • 1
  • Akiko Matsumoto
    • 1
  • Ichiro Takase
    • 1
  1. 1.Division of Entomology and Parasitology, College of Natural ResourcesUniversity of CaliforniaBerkeley

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