L-Canavanine: a higher plant insecticidal allelochemical
- PMID: 11764412
- DOI: 10.1007/s007260170017
L-Canavanine: a higher plant insecticidal allelochemical
Abstract
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.
Similar articles
-
Aberrant, canavanyl protein formation and the ability to tolerate or utilize L-canavanine.Experientia. 1987 May 15;43(5):558-61. doi: 10.1007/BF02143585. Experientia. 1987. PMID: 3582574
-
Biochemical insight into insecticidal properties ofL-Canavanine, a higher plant protective allelochemical.J Chem Ecol. 1986 May;12(5):1145-56. doi: 10.1007/BF01639001. J Chem Ecol. 1986. PMID: 24307052
-
L-homoarginine studies provide insight into the antimetabolic properties of L-canavanine.Insect Biochem Mol Biol. 1996 Apr;26(4):389-94. doi: 10.1016/0965-1748(95)00106-9. Insect Biochem Mol Biol. 1996. PMID: 8814786
-
The biological effects and mode of action of L-canavanine, a structural analogue of L-arginine.Q Rev Biol. 1977 Jun;52(2):155-78. doi: 10.1086/409853. Q Rev Biol. 1977. PMID: 331385 Review.
-
The mechanism of L-canavanine cytotoxicity: arginyl tRNA synthetase as a novel target for anticancer drug discovery.J Enzyme Inhib Med Chem. 2003 Oct;18(5):383-94. doi: 10.1080/1475636031000152277. J Enzyme Inhib Med Chem. 2003. PMID: 14692504 Review.
Cited by
-
Canavanine utilization via homoserine and hydroxyguanidine by a PLP-dependent γ-lyase in Pseudomonadaceae and Rhizobiales.RSC Chem Biol. 2022 Aug 25;3(10):1240-1250. doi: 10.1039/d2cb00128d. eCollection 2022 Oct 5. RSC Chem Biol. 2022. PMID: 36320885 Free PMC article.
-
Dual mechanism for bitter avoidance in Drosophila.J Neurosci. 2015 Mar 4;35(9):3990-4004. doi: 10.1523/JNEUROSCI.1312-14.2015. J Neurosci. 2015. PMID: 25740527 Free PMC article.
-
Reassignment of a rare sense codon to a non-canonical amino acid in Escherichia coli.Nucleic Acids Res. 2015 Sep 18;43(16):8111-22. doi: 10.1093/nar/gkv787. Epub 2015 Aug 3. Nucleic Acids Res. 2015. PMID: 26240376 Free PMC article.
-
Cyanamide is biosynthesized from L-canavanine in plants.Sci Rep. 2015 May 27;5:10527. doi: 10.1038/srep10527. Sci Rep. 2015. PMID: 26013398 Free PMC article.
-
Gustatory receptors required for avoiding the insecticide L-canavanine.J Neurosci. 2012 Jan 25;32(4):1429-35. doi: 10.1523/JNEUROSCI.4630-11.2012. J Neurosci. 2012. PMID: 22279227 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
