Alternariol

CHF 65.00
In stock
BVT-0465-M0011 mgCHF 65.00
BVT-0465-M0055 mgCHF 195.00
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Product Details
Synonyms AOH; NSC 638263; 3,4',5-Trihydroxy-6'-methyldibenzo-α-pyrone
Product Type Chemical
Properties
Formula

C14H10O5

MW 258.2
CAS 641-38-3
RTECS HP8757000
Source/Host Chemicals Isolated from Alternaria sp.
Purity Chemicals ≥98% (HPLC)
Appearance Light brown solid.
Solubility Soluble in DMSO (20mg/ml) or DMF. Slightly soluble in acetone (1mg/ml).
Identity Determined by 1H-NMR.
Declaration Manufactured by BioViotica.
InChi Key CEBXXEKPIIDJHL-UHFFFAOYSA-N
Smiles OC1=CC(C2=C(C)C=C(O)C=C2O3)=C(C(O)=C1)C3=O
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 +4°C.
After reconstitution protect from light at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • Mycotoxin.
  • Phytotoxin.
  • Shows cytotoxic, teratogenic, mutagenic and genotoxic properties by DNA intercalation.
  • Induces several types of DNA damage, including oxidative DNA damage, single-stranded DNA breaks (SSB) and double-strand, through AOH-induced ROS production and interaction with DNA topoisomerase.
  • Inhibits the activity of topoisomerase IIα in mammalian cells.
  • Induces cell growth arrest in G2/M phase.
  • GSK-3β inhibitor (sub-μM IC50 values).
  • Antiviral activity (herpes simplex).
  • Hepatitis C NS3-4A protease inhibitor.
  • Induces cytochrome P450 1A1 expression and apoptosis in mouse hepatoma cells.
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. Alternariol, a dibenzopyrone mycotoxin of Alternaria spp., is a new photosensitizing and DNA cross-linking agent: F. DiCosmo & N.A. Straus; Experientia 41, 1188 (1985)
  3. 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)
  4. Alternariol acts as a topoisomerase poison preferentially affecting the IIα isoform.: M. Fehr, et al.; Mol. Nutr. Food Res. 53, 441 (2009)
  5. Mechanism of Alternariol monomethyl ether-induced mitochondrial apoptosis in human colon carcinoma cells: F. Bensassi, et al.; Toxicology 290, 230 (2011)
  6. 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)
  7. Alternariol: D. Siegel, et al.; Acta Crystallogr. Sec. E Struct. Rep. Online 66, o1366 (2010)
  8. 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)
  9. Modulation of the cellular redox status by the Alternaria toxins alternariol and alternariol monomethyl ether: C. Tiessen, et al.; Toxicol. Lett. 216, 23 (2013)
  10. Mycotoxins from Alternaria: toxicological implications: C. Dall'Asta, et al.; Adv. Mol. Toxicol. 8, 107 (2014)
  11. 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)
  12. Marine fungi as producers of benzocoumarins, a new class of inhibitors of glycogen-synthase-kinase 3β: J. Wiese, et al.; Mar. Drugs 2016, 14 (2016)
  13. Involvement of p38MAPK-ATF2 signaling pathway in alternariol induced DNA polymerase β expression: Z. Jimin, et al.; Oncol. Lett. 12, 675 (2016)
  14. Alternariol induce toxicity via cell death and mitochondrial damage on Caco-2 cells: C. Fernandez-Blanco, et al.; Food Chem. Toxicol. 88, 32 (2016)
  15. Mechanisms of Action and Toxicity of the Mycotoxin Alternariol: A Review: A. Solhaug, et al.; Basic Clin. Pharmacol. Toxicol. 119, 533 (2016)
  16. The Alternaria alternata Mycotoxin alternariol suppresses lipopolysaccharide-induced inflammation: S. Grover & C. B. Lawrence; Int. J. Mol. Sci. 2017, 18 (2017)
  17. Impact of phase I metabolism on uptake, oxidative stress and genotoxicity of the emerging mycotoxin alternariol and its monomethyl ether in esophageal cells: C. Tiessen, et al.; Arch. Toxicol. 91, 1213 (2017)
  18. Dual effectiveness of alternaria but not fusarium mycotoxins against human topoisomerase II and bacterial gyrase: K. Jarolim, et al.; Arch. Toxicol. 91, 2007 (2017)
  19. Genistein and delphinidin antagonize the genotoxic effects of the mycotoxin alternariol in human colon carcinoma cells: G. Aichinger, et al.; Mol. Nutr. Food Res. 2017, 61 (2017)
  20. Nonsteroidal mycotoxin alternariol is a full androgen agonist in the yeast reporter androgen bioassay: S. Stypula-Trebas, et al.; Environ. Toxicol. Pharmacol. 55, 208 (2017)
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