37338-80-0
Chemical Structure
Orellanine
- CAS. Nr.: 37338-80-0
- Formula:C10H8N2O6
- Molecular Weight:252.18
IUPAC Name: 3,3',4,4'-tetrahydroxy-[2,2'-bipyridine] 1,1'-dioxide
InChIKey: JEWWXPOUSBVQKG-UHFFFAOYSA-N
SMILES: [O-][N+]1=CC=C(O)C(O)=C1C2=C(O)C(O)=CC=[N+]2[O-]
Biological Activity: Orellanine, a nephrotoxic alkaloid found in Cortinarius orellanus, is an orally active and selective non-competitive inhibitor of alkaline phosphatase. Orellanine chelates iron, generates reactive oxygen species (ROS), induces DNA scission, forms ortho-semiquinone radicals, downregulates antioxidant defenses, and inhibits mitochondrial function. Orellanine induces caspase 8/9-mediated apoptosis. Orellanine inhibits synthesis of proteins, RNA, DNA, and mitochondrial protein synthesis, with metabolic activation required for cell-free protein synthesis inhibition. Orellanine can be used for the research of metastatic clear cell renal cell carcinoma, acute renal failure, chronic renal insufficiency, and kidney damage[1][2][3].
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Orellanine | 98.0% | Orellanine, a nephrotoxic alkaloid found in Cortinarius orellanus, is an orally active and selective non-competitive inhibitor of alkaline phosphatase. Orellanine chelates iron, generates reactive oxygen species (ROS), induces DNA scission, forms ortho-semiquinone radicals, downregulates antioxidant defenses, and inhibits mitochondrial function. Orellanine induces caspase 8/9-mediated apoptosis. Orellanine inhibits synthesis of proteins, RNA, DNA, and mitochondrial protein synthesis, with metabolic activation required for cell-free protein synthesis inhibition. Orellanine can be used for the research of metastatic clear cell renal cell carcinoma, acute renal failure, chronic renal insufficiency, and kidney damage. | ||||||||||||||||||||
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- [1]. Lyons MJ, et al. Orellanine: From Fungal Origin to a Potential Future Cancer Treatment. J Nat Prod. 2023;86(6):1620-1631. [Content Brief]
- [2]. Dinis-Oliveira RJ, et al. Human and experimental toxicology of orellanine. Hum Exp Toxicol. 2016;35(9):1016-1029. [Content Brief]
- [3]. Richard JM, et al. Orellanine inhibits protein synthesis in Madin-Darby canine kidney cells, in rat liver mitochondria, and in vitro: indication for its activation prior to in vitro inhibition. Toxicology. 1991;67(1):53-62. [Content Brief]
Keywords
