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discounted EARLY registration ends Dec 31, 2014
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Pathway: ricinine degradation

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis Nitrogen-Containing Secondary Compounds Biosynthesis Alkaloids Biosynthesis

Some taxa known to possess this pathway include ? : Pseudomonas , Ricinus communis

Expected Taxonomic Range: Bacteria , Eukaryota

Summary:
Ricinine is a cyano-pyridone alkaloid produced by some plants. It was first identified in the leaves and the pericarp of the fruits of the toxic plant castor bean (Ricinus communis) [Bogdashevskaia52, Bogdashevskaia54, Grimme75] (hence the name), but it is also produced by other plants including Aparisthmium cordatum [Souza13], Jatropha gossypiifolia, Piper nigrum, Nicotiana tabacum and other plant species belonging to the Solanaceae family [Bullangpoti11].

In low doses ricinine acts as a central nervous system stimulant, and in higher doses it is lethal. The therapeutic index of ricinine is of the order of 200 [Janssen64, Ferraz00, Ferraz99].

Ricinine should not be confused with ricin, a toxic protein that is also produced by Ricinus communis, and is found in the seeds.

Degradation of ricinine in the living plant has been known for a long time [Waller69]. Experiments in castor bean plants have shown that ricinine concentration decreases in the leaves upon aging when grown in nitrogen depleted soil. Despite the fact that the degradation of ricinine in the plant has been under investigation for several decades, it is still not well understood. Ricinine is rapidly utilized by castor cotyledons grown in the dark and degradation of ricinine in cell-free system of young castor plants has been demonstrated [Waller65]. However, no enzymes have been isolated.

This pathway describes the bacterial hydrolysis of ricinine, as described in several bacterial strains of Pseudomonads [Waller72, Skursky69].

Credits:
Created 30-Sep-2011 by Pujar A , Boyce Thompson Institute


References

Bogdashevskaia52: Bogdashevskaia OV (1952). "[Formation of ricinine and castor oil]." Dokl Akad Nauk SSSR 82(6);1001-3. PMID: 14916779

Bogdashevskaia54: Bogdashevskaia OV (1954). "[Biologic biosynthesis of ricinine]." Dokl Akad Nauk SSSR 99(5);853-4. PMID: 14365610

Bullangpoti11: Bullangpoti, V, Khumrungsee, N, Pluempanupat, W, Kainoh, Y, Saguanpong, U. (2011). "Toxicity of ethyl acetate extract and ricinine from Jatropha gossypifolia senescent leaves against Spodoptera exigua Hubner (Lepidoptera: Noctuidae)." Journal of Pestcide Science 36: 260-263.

Ferraz00: Ferraz AC, Pereira LF, Ribeiro RL, Wolfman C, Medina JH, Scorza FA, Santos NF, Cavalheiro EA, Da Cunha C (2000). "Ricinine-elicited seizures. A novel chemical model of convulsive seizures." Pharmacol Biochem Behav 65(4);577-83. PMID: 10764909

Ferraz99: Ferraz AC, Angelucci ME, Da Costa ML, Batista IR, De Oliveira BH, Da Cunha C (1999). "Pharmacological evaluation of ricinine, a central nervous system stimulant isolated from Ricinus communis." Pharmacol Biochem Behav 63(3);367-75. PMID: 10418776

Grimme75: Grimme U (1975). "[Final examination nursing care study of a child with severe acidosis and concurrently a convulsion]." Dtsch Krankenpflegez 28(11);645-7. PMID: 1041877

Janssen64: Janssen C (1964). "[Note on ricinine, toxin from Ricinus seeds]." Bull Soc Chim Biol (Paris) 46;317-22. PMID: 14165547

Skursky69: Skursky L, Burleson D, Waller GR (1969). "Interconversion of ricinine and n-demethylricinine in senescent and green castor plant leaves." J Biol Chem 244(12);3238-42. PMID: 5792659

Souza13: Souza KM, Guilhon GM, Santos LS, Cascaes MM, Secco RS, Brasil DS, Andrade EH, Marinho PS, Freire LR, Muller AH (2013). "Ricinine and other constituents of Aparisthmium cordatum (Euphorbiaceae)." Nat Prod Res 27(4-5);364-70. PMID: 22708684

Waller65: Waller GR, Tang MS, Scott MR, Goldberg FJ, Mayes JS, Auda H (1965). "Metabolism of ricinine in the castor plant." Plant Physiol 40(5);803-7. PMID: 5829600

Waller69: Waller GR, Lee JL (1969). "Metabolism of the alpha-Pyridone Ring of Ricinine in Ricinus communis L." Plant Physiol 44(4);522-6. PMID: 16657095

Waller72: Waller GR, Skursky L (1972). "Translocation and Metabolism of Ricinine in the Castor Bean Plant, Ricinus communis L." Plant Physiol 50(5);622-6. PMID: 16658229

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Hook64: Hook RH, Robinson WG (1964). "Ricinine nitrilase. II. Purification and properties." J Biol Chem 239;4263-7. PMID: 14247680

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sun Dec 21, 2014, biocyc11.