Orellanine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 584940

CAS#: 37338-80-0

Description: Orellanine is isolated from Cortinarius orellanus and targets renal clear cell carcinoma.

Chemical Structure

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Orellanine
CAS# 37338-80-0
Instruction

Theoretical Analysis

MedKoo Cat#: 584940
Name: Orellanine
CAS#: 37338-80-0
Chemical Formula: C10H8N2O6
Exact Mass: 252.04
Molecular Weight: 252.182
Elemental Analysis: C, 47.63; H, 3.20; N, 11.11; O, 38.07

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Orellanine

IUPAC/Chemical Name: (2,2'-Bipyridine)-3,3',4,4'-tetrol, 1,1'-dioxide

InChi Key: JEWWXPOUSBVQKG-UHFFFAOYSA-N

InChi Code: InChI=1S/C10H8N2O6/c13-5-1-3-11(17)7(9(5)15)8-10(16)6(14)2-4-12(8)18/h1-4,13-16H

SMILES Code: OC1=C(C2=C(O)C(O)=CC=[N+]2[O-])[N+]([O-])=CC=C1O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 252.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Buvall L, Hedman H, Khramova A, Najar D, Bergwall L, Ebefors K, Sihlbom C, Lundstam S, Herrmann A, Wallentin H, Roos E, Nilsson UA, Johansson M, Törnell J, Haraldsson B, Nyström J. Orellanine specifically targets renal clear cell carcinoma. Oncotarget. 2017 Jul 25;8(53):91085-91098. doi: 10.18632/oncotarget.19555. eCollection 2017 Oct 31. PubMed PMID: 29207627; PubMed Central PMCID: PMC5710908.

2: Shao D, Tang S, Healy RA, Imerman PM, Schrunk DE, Rumbeiha WK. A novel orellanine containing mushroom Cortinarius armillatus. Toxicon. 2016 May;114:65-74. doi: 10.1016/j.toxicon.2016.02.010. Epub 2016 Feb 23. PubMed PMID: 26915341.

3: Anantharam P, Shao D, Imerman PM, Burrough E, Schrunk D, Sedkhuu T, Tang S, Rumbeiha W. Improved Tissue-Based Analytical Test Methods for Orellanine, a Biomarker of Cortinarius Mushroom Intoxication. Toxins (Basel). 2016 May 21;8(5). pii: E158. doi: 10.3390/toxins8050158. PubMed PMID: 27213453; PubMed Central PMCID: PMC4885072.

4: Dinis-Oliveira RJ, Soares M, Rocha-Pereira C, Carvalho F. Human and experimental toxicology of orellanine. Hum Exp Toxicol. 2016 Sep;35(9):1016-29. doi: 10.1177/0960327115613845. Epub 2015 Nov 9. Review. PubMed PMID: 26553321.

5: Herrmann A, Hedman H, Rosén J, Jansson D, Haraldsson B, Hellenäs KE. Analysis of the mushroom nephrotoxin orellanine and its glucosides. J Nat Prod. 2012 Oct 26;75(10):1690-6. doi: 10.1021/np300135k. Epub 2012 Oct 9. PubMed PMID: 23046414.

6: Oubrahim H, Richard JM, Cantin-Esnault D. Peroxidase-mediated oxidation, a possible pathway for activation of the fungal nephrotoxin orellanine and related compounds. ESR and spin-trapping studies. Free Radic Res. 1998 May;28(5):497-505. PubMed PMID: 9702530.

7: Najar D, Haraldsson B, Thorsell A, Sihlbom C, Nyström J, Ebefors K. Pharmacokinetic Properties of the Nephrotoxin Orellanine in Rats. Toxins (Basel). 2018 Aug 17;10(8). pii: E333. doi: 10.3390/toxins10080333. PubMed PMID: 30126099; PubMed Central PMCID: PMC6116018.

8: Nilsson UA, Nyström J, Buvall L, Ebefors K, Björnson-Granqvist A, Holmdahl J, Haraldsson B. The fungal nephrotoxin orellanine simultaneously increases oxidative stress and down-regulates cellular defenses. Free Radic Biol Med. 2008 Apr 15;44(8):1562-9. doi: 10.1016/j.freeradbiomed.2008.01.017. Epub 2008 Jan 31. PubMed PMID: 18279679.

9: Richard JM, Louis J, Cantin D. Nephrotoxicity of orellanine, a toxin from the mushroom Cortinarius orellanus. Arch Toxicol. 1988;62(2-3):242-5. PubMed PMID: 3196164.

10: Hedman H, Holmdahl J, Mölne J, Ebefors K, Haraldsson B, Nyström J. Long-term clinical outcome for patients poisoned by the fungal nephrotoxin orellanine. BMC Nephrol. 2017 Apr 3;18(1):121. doi: 10.1186/s12882-017-0533-6. PubMed PMID: 28372584; PubMed Central PMCID: PMC5379567.

11: Koller GE, Høiland K, Janak K, Størmer FC. The presence of orellanine in spores and basidiocarp from Cortinarius orellanus and Cortinarius rubellus. Mycologia. 2002 Sep-Oct;94(5):752-6. PubMed PMID: 21156548.

12: Richard JM, Cantin-Esnault D, Jeunet A. First electron spin resonance evidence for the production of semiquinone and oxygen free radicals from orellanine, a mushroom nephrotoxin. Free Radic Biol Med. 1995 Oct;19(4):417-29. PubMed PMID: 7590391.

13: Nagaraja P, Thangavelu A, Nair H, Kumwenda M. Successful living related kidney transplantation for end-stage renal failure caused by orellanine syndrome. QJM. 2015 May;108(5):413-5. doi: 10.1093/qjmed/hcs201. Epub 2012 Oct 24. PubMed PMID: 23097388.

14: Richard JM, Ravanel P, Cantin D. Phytotoxicity of orellanine, a mushroom toxin. Toxicon. 1987;25(3):350-4. PubMed PMID: 3590215.

15: Fulde K, Böhler J, Keller E, Frahm AW. Efficiency of haemoperfusion materials at removing the fungal toxin orellanine from human plasma. Pharmazie. 1998 Jan;53(1):58-9. PubMed PMID: 9476259.

16: Richard JM, Taillandier G, Ramos MN, Galdino SL, Da Rocha Pitta I. [QSAR analysis of the toxicity of a series of pyridines related to the mushroom toxin orellanine: comparison of the results obtained with physico-chemical, steric and quantal parameters]. Pharmazie. 1990 Oct;45(10):771-4. French. PubMed PMID: 2089389.

17: Oubrahim H, Richard JM, Cantin-Esnault D, Seigle-Murandi F, Trécourt F. Novel methods for identification and quantification of the mushroom nephrotoxin orellanine. Thin-layer chromatography and electrophoresis screening of mushrooms with electron spin resonance determination of the toxin. J Chromatogr A. 1997 Jan 10;758(1):145-57. PubMed PMID: 9181972.

18: Richard JM, Taillandier G, Benoit-Guyod JL. A quantitative structure-activity relationship study on substituted pyridines as a contribution to the knowledge of the toxic effects of orellanine, a toxin from the mushroom Cortinarius orellanus. Toxicon. 1985;23(5):815-24. PubMed PMID: 4089876.

19: Karlson-Stiber C, Persson H. Cytotoxic fungi--an overview. Toxicon. 2003 Sep 15;42(4):339-49. Review. PubMed PMID: 14505933.

20: Spiteller P, Spiteller M, Steglich W. Occurrence of the fungal toxin orellanine as a diglucoside and investigation of its biosynthesis. Angew Chem Int Ed Engl. 2003 Jun 30;42(25):2864-7. PubMed PMID: 12833343.