862 Lotaustralin Epilotaustralin is found in cereals and cereal products. Epilotaustralin is isolated from Triticum monococcum (wheat). 534-67-8 4626626 C11H19NO6 261.121240 White powder. 139°C Oral Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97) Upon exposure to enzymes and gut flora in the human intestine, lotaustralin can decompose to the toxic chemical hydrogen cyanide. This occurs via the enzyme linamarase, which is found in the cell wall of the plant. Chewing of the plant allows the enzyme to contact the lotaustralin converting it into acetone cyanohydrin, which then spontaneously decomposes to hydrogen cyanide. (L630, L1240) Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96) No indication of carcinogenicity to humans (not listed by IARC). Lotaustralin is a plant toxin found in the roots and leaves of plants such as cassava (Manihot esculenta), lima bean (Phaseolus lunatus), roseroot (Rhodiola rosea) and white clover (Trifolium repens). (L1240) Dietary exposure to lotaustralin has been reported as a risk factor in developing glucose intolerance and diabetes. It may also cause the upper motor neuron disease known as konzo. (L630, L1240) Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97) 2009-06-10T21:44:10Z 2026-04-06T01:54:26Z Cyanogenic beta-glucosidase (P26205) (L630) http://en.wikipedia.org/wiki/Lotaustralin C08334 C001556 Lotaustralin true Cyanogenic beta-glucosidase (P26205) (L630) [H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(O[C@](C)(CC)C#N)[C@]1([H])O C11H19NO6 InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3/t6-,7-,8+,9-,10+,11-/m1/s1 WEWBWVMTOYUPHH-QHAQEBJBSA-N 261.2717 261.121237345 Exogenous Solid HMDB33865 3817241 CHEM000743 DTXSID30897501 NS00094436 (2R)-2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanenitrile