l-Canavanine: a higher plant insecticidal allelochemical

  title={l-Canavanine: a higher plant insecticidal allelochemical},
  author={Gerald A. Rosenthal},
  journal={Amino Acids},
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… 
l-Canavanine: How does a simple non-protein amino acid inhibit cellular function in a diverse living system?
In higher plants, CAN has recently been used as a tool to study the regulation or modulation of polyamine–NO cross-talk, and seems to have the highest toxic properties.
Allelochemicals and activities in a replanted Chinese fir (Cunninghamia lanceolata (Lamb.) Hook) tree ecosystem.
The results suggest that phenolics and friedelin are not key allelochemicals since they are weakly phytotoxic and are detected in low concentrations in the replanted Chinese fir tree ecosystem, while cyclic dipeptide is a highly active alle Lochemical with a phytOToxic effect that limits offspring growth in the Replanted Chinese Fir tree ecosystem.
Quantification of Canavanine, 2-Aminoethanol, and Cyanamide in Aphis craccivora and its Host Plants, Robinia pseudoacacia and Vicia angustifolia: Effects of These Compounds on Larval Survivorship of Harmonia axyridis
Results indicate that the toxicity of A. craccivora infesting the two host plants is at least partly due to cyanamide, which is present in the toxic A. pseudoacacia, and canavanine, 2-aminoethanol, and cyanamide exhibited 10–100 times stronger toxicity.
Plant Insecticide L-Canavanine Repels Drosophila via the Insect Orphan GPCR DmX
These findings show that the DmX receptor, which does not belong to the Gr family, fulfills a gustatory function necessary to avoid eating a natural toxin.
Cyanamide is biosynthesized from l-canavanine in plants
Cyanamide had long been recognized as a synthetic compound but more recently has been found as a natural product from several leguminous plants. This compound’s biosynthetic pathway, as yet
Overview of the potent cyanobacterial neurotoxin β-methylamino-L-alanine (BMAA) and its analytical determination
The aim of this review is to focus on the methods of extraction and analysis of the neurotoxic non-protein amino acid BMAA, and considers the neurotoxicity, aetiology, and diverse sources and routes of exposure to BMAA.


L-Canavanine and protein synthesis in the tobacco hornworm Manduca sexta.
  • G. Rosenthal, D. Dahlman
  • Biology
    Proceedings of the National Academy of Sciences of the United States of America
  • 1986
L-Canavanine, a nonprotein amino acid of certain leguminous plants, manifests potent insecticidal properties in a canavanine-sensitive insect such as the tobacco hornworm Manduca sexta (L.)
Insecticidal properties of some derivatives of L-canavanine
The 1-methyl and 1-ethyl esters of L-canavanine were synthesized to determine if enhancing canavanine's hydrophobicity might increase its bioavailability, and it was revealed that these esters are less toxic thanCanavanine ; the ethyl ester disrupted larval growth more than did the methyl analogue.
The Natural Abundance Of L-Canavanine, An Active Anticancer Agent, in Alfalfa, Medicago Sativa (L.)
Alfalfa seed canavanine content was comparable to the levels found in the seeds of representative members of the genus Canavalia, which are amongst the more abundance sources of this antimetabolite.
The biochemical basis for L-canavanine tolerance by the tobacco budworm Heliothis virescens (Noctuidae).
The tobacco budworm, Heliothis virescens (Noctuidae), a destructive insect pest, is remarkably resistant to L-canavanine, L-2-amino-4-(guanidinooxy)butyric acid, an arginine antimetabolite that is a
Effect of Long-Chained Esters on the Insecticidal Properties of L-Canavanine.
The ability of the several esters of L-canavanine, a potentially insecticidal natural product of leguminous plants, to enhance the potency of the parent compound was evaluated with the propyl, butyl,
Studies of L-canavanine incorporation into insectan lysozyme.
The Biological Effects and Mode of Action of L-Canavanine, a Structural Analogue of L-Arginine
  • G. Rosenthal
  • Biology, Chemistry
    The Quarterly Review of Biology
  • 1977
Canavanine is a highly toxic secondary plant constituent that probably functions as an allelochemic agent that deters the feeding activity of phytophagous insects and other herbivores.
Biochemical Ecology of Canavanine‐Eating Seed Predators
Analysis of larval Coleoptera in northwestern Guanacaste Province in Costa Rica revealed that certain biochemical capacities required by canavanine—feeding insects may have existed prior to their exposure to dietaryCanavanine.