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Azetidine-2-carboxylic acid: A naturally occurring inhibitor ofSpodoptera littoralis (boisd.) (Lepidoptera: Noctuidae)

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Abstract

Ruscus hypoglossum andUrginea maritima (Liliaceae) are highly resistant toSpodoptera littoralis. The foliage of these plants contains a proline analog, L-azetidine-2-carboxylic acid (AZA): inUrginea at a concentration of 1.7% of fresh weight and inRuscus at a concentration of 0.019%. The concentration of AZA inUrginea accounts for its lethal effects onS. littoralis larvae and for the direct effect of an acetone-soluble 80% methanol extract on adultS. littoralis, as evidenced by reduced viability of eggs deposited. The toxicity ofRuscus extracts is only partly attributable to AZA content.

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References

  1. 1.

    Baum, B.J.,Troxler, R.F.,Kagan, H.M.,Grasso, J.A.,Faris, B. andFranzblau, C. (1973) Incorporation of L-azetidine-2-carboxylic acid into hemoglobin in rabbit reticulocytes.Biochim. biophys. Res. Commun. 53: 1350–1356.

  2. 2.

    Bombardelli, E.,Bonati, A.,Gabetta, B. andMustich, G. (1971) Glycosides from rhizomes ofRuscus aculeatus L.Fitoterapia 42: 127–136.

  3. 3.

    Fowden, L. (1956) Azetidine-2-carboxylic acid: a new cyclic amino acid occurring in plants.Biochem. J. 64: 323–332.

  4. 4.

    Fowden, L. (1963) Amino-acid analogues and the growth of seedlings.J. exp. Bot. 14: 387–398.

  5. 5.

    Fowden, L. andRichmond, M.K. (1963) Replacement of proline by azetidine-2-carboxylic acid during biosynthesis of protein.Biochim. biophys. Acta 71: 459–461.

  6. 6.

    Fraenkel, G.S. (1959) The raison d’être of secondary plant substances.Science, N. Y. 129: 1466–1470.

  7. 7.

    Hegnauer, R. (1970) Cardenolide und Bufadienolide (= Cardadienolide).Planta Med. 19: 138–153.

  8. 8.

    Hewitt, E.J. andNotton, B.A. (1967) Inhibition by L-azetidine-2-earboxylic acid of induction of nitrate reductase in plants and its reversal by L-proline.Phytochemistry 6: 1329–1335.

  9. 9.

    Jacobson, M. andCrosby, D.G. (1971) Naturally Occurring Insecticides. Marcel Dekker Inc., New York.

  10. 10.

    Kerwar, S.S.,Marcel, R.J. andSalvador, R.A. (1975) Reduction of prolyl hydroxylase activity in L-929 fibroblasts by proline analogs.Biochem. biophys. Res. Comm. 66: 1275–1280.

  11. 11.

    Lane, J.M.,Dehm, P. andProckop, D.J. (1971) Effect of the proline analog azetidine-2-carboxylic acid on collagen synthesisin vivo. I. Arrest of collagen accumulation in growing chick embryos.Biochim. biophys. Acta 236: 517–527.

  12. 12.

    Panova, D.,Nikolov, S. andAkhtardzhiev, Khr. (1974) Steroid Sapogenine und Stcrole ausRuscus hypoglossum.Planta Med. 26: 90–93.

  13. 13.

    Richmond, M.H. (1962) The effect of amino acid analogues on growth and protein synthesis in microorganisms.Bacteriol. Rev. 26: 398–420.

  14. 14.

    Sannie, C. etLapin, H. (1955) Sur une nouvelle sapogenine sterolique: la ruscogenine, extraite des rhizomes deRuscus aculeatus L.C.r.Acad. Sci. 241: 1498–1500.

  15. 15.

    Steward, F.C.,Pollard, J.K.,Patchett, A.A. andWitkop, B. (1958) The effect of selected nitrogen compounds on the growth of plant tissue cultures.Biochim. biophys. Acta 28: 308–317.

  16. 16.

    Takeuchi, T. andProckop, D.J. (1969) Biosynthesis of abnormal collagens with amino acid analogues. 1. Incorporation of L-azetidine-2-carboxylic acid and cis-4-fluoro-L-proline into protocollagen and collagen.Biochim. biophys. Acta 175: 142–155.

  17. 17.

    Troxler, R.F. andBrown, A.S. (1974) Metabolism of L-azetidine-2-carboxylic acid in the algaCyanidium caldarium.Biochim. biophys. Acta 366: 341–349.

  18. 18.

    Uitto, J. andProckop, D.J. (1974) Incorporation of proline analogs into collagen polypeptides. Effects on the production of extracellular procollagen and on the stability of the triple-helical structure of the molecule.Biochim. biophys. Acta 336: 234–251.

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Correspondence to Esther Hassid or S. W. Applebaum or Yehudith Birk.

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Hassid, E., Applebaum, S.W. & Birk, Y. Azetidine-2-carboxylic acid: A naturally occurring inhibitor ofSpodoptera littoralis (boisd.) (Lepidoptera: Noctuidae). Phytoparasitica 4, 173 (1976). https://doi.org/10.1007/BF02981084

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Key words

  • Ruscus hypoglossum
  • Urginea maritima
  • Spodoptera littoralis
  • azetidine-2-carboxylic acid
  • non-protein amino acids