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Alternariol monomethyl ether

BVT-0323-C500 500 µg $70.00
BVT-0323-M001 1 mg $100.00
BVT-0323-M005 5 mg $350.00
BVT-0323-M010 10 mg $630.00
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Additional Information

Product Data
Synonyms 9-O-Methylalternariol; Djalonensone; AME; BRN 0253553; 3,7-Dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one
Properties
Formula C15H12O5
MW 272.3
CAS 26894-49-5
Source/Host Chemicals Isolated from Alternaria sp.
Purity ≥98% (HPLC)
Appearance Off-white to light brown solid.
Solubility Soluble in methanol, dichloromethane or methylene chloride.
Identity Determined by 1H-NMR.
Origin Manufactured by BioViotica.
InChi Key LCSDQFNUYFTXMT-UHFFFAOYSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage +4°C
Handling Advice Keep cool and dry.
Use/Stability Stable for at least 1 year after receipt when stored at -20°C. After reconstitution protect from light at -20°C.
Documents
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Product Description

  • Mycotoxin.
  • Antifungal.
  • Phytotoxic.
  • Shown to possess DNA strand-breaking activity.
  • Inhibits the activity of topoisomerase IIα (Topo IIα) in mammalian cells.
  • Antiviral (Herpes simplex).
  • Hepatitis C NS3-4A protease inhibitor.

Product References

  1. Studies in the biochemistry of micro-organisms. 90. Alternariol and alternariol monomethyl ether, metabolic products of Alternariatenuis: H. Raistrick, et al.; Biochem. J. 55, 421 (1953)
  2. Light inhibits the production of alternariol and alternariol monomethyl ether in Alternaria alternata: K. Soderhall, et al.; Appl. Environ. Microbiol. 36, 655 (1978)
  3. Toxicity of the Alternaria metabolites alternariol, alternariol methyl ether, altenuene, and tenuazonic acid in the chicken embryo assay: G.F. Griffin & F.S. Chu; Appl. Environ. Microbiol. 46, 1420 (1983)
  4. Evaluation of alternariol and alternariol methyl ether for mutagenic activity in Salmonella typhimurium: V.M. Davis & M.E. Stack; Appl. Environ. Microbiol. 60, 3901 (1994)
  5. Alternariol acts as a topoisomerase poison preferentially affecting the IIα isoform.: M. Fehr, et al.; Mol. Nutr. Food Res. 53, 441 (2009)
  6. Mechanism of Alternariol monomethyl ether-induced mitochondrial apoptosis in human colon carcinoma cells: F. Bensassi, et al.; Toxicology 290, 230 (2011)
  7. Heptaketides with antiviral activity from three endolichenic fungal strains Nigrospora sp., Alternaria sp. and Phialophora sp.: J.-W. He, et al.; Fitoterapia 83, 1087 (2012)
  8. Alternariol 9-O-methyl ether: S. Dasari, et al.; Acta Crystallographica, Section E 68, o1471 (2012)
  9. The Fungal Phytotoxin Alternariol 9-Methyl Ether and Some of Its Synthetic Analogues Inhibit the Photosynthetic Electron Transport Chain: A. Demuner, et al.; J. Nat. Prod. 76, 2234 (2013)
  10. Modulation of the cellular redox status by the Alternaria toxins alternariol and alternariol monomethyl ether: C. Tiessen, et al.; Toxicol. Lett 216, 23 (2013)
  11. Mycotoxins from Alternaria: toxicological implications: C. Dall'Asta, et al.; Adv. Mol. Toxicol. 8, 107 (2014)
  12. Mycotoxins as antagonistic or supporting agents in the interaction between phytopathogenic Fusarium and Alternaria fungi: M. E. H. Mueller, et al.; World Mycotoxin J. 8, 311 (2015)
  13. Combined effects of alternariols mixture on human colon carcinoma cells: F. Bensassi, et al.; Toxicol. Mech. Meth. 25, 56 (2015)
  14. Alternariol derivatives from Alternaria alternata, an endophytic fungus residing in red sea soft coral, inhibit HCV NS3/4A protease: U. Hawas, et al.; Appl. Biochem. Microbiol. 51, 579 (2015)
  15. Impact of Alternaria toxins on CYP1A1 expression in different human tumor cells and relevance for genotoxicity: G. Pahlke, et al.; Toxicol. Lett. 240, 93 (2016)
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