l-Canavanine: a higher plant insecticidal allelochemical

Summary.

l-Canavanine, l-2-amino-4-(guanidinooxy)butyric acid, is a potentially toxic nonprotein amino acid of certain leguminous plants. Many species are prolific canavanine producers; they divert enormous nitrogen resource to the storage of this single natural product. Canavanine, a highly effective protective allelochemical, provides a formidable chemical barrier to predation and disease.

The accumulated experimental evidence leaves little doubt that the key element in the ability of canavanine to function as an effective protective allelochemical is its subtle structural mimicry of arginine which makes it an effective substrate for amino acid activation and aminoacylation, and its marked diminution in basicity relative to arginine which mediates the production of structural aberrant, dysfunctional canavanyl proteins.

The biological burdens of canavanyl protein formation by canavanine-treated Manduca sexta larvae were carried throughout their remaining life cycle. Protein-based sequestration of canavanine prevented turnover and clearance of the free amino acid, and undoubtedly contributed significantly to the antimetabolic character of this protective allelochemical.

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

Author information

Affiliations

Authors

Additional information

Received February 1, 2000 Accepted June 4, 2000

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Rosenthal, G. l-Canavanine: a higher plant insecticidal allelochemical. Amino Acids 21, 319–330 (2001). https://doi.org/10.1007/s007260170017

Download citation

  • Keywords: Amino acids
  • l-Canavanine
  • Allelochemical
  • Natural products