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Alternariol

Catalog No.
C5061
A mycotoxin with antifungal and phytotoxic activity
Grouped product items
Size Price Stock Qty
1mg
Special Price $48.60 Regular Price $108.00
Ship with 5-10 days
5mg
Special Price $145.35 Regular Price $323.00
Ship with 5-10 days
For scientific research use only and should not be used for diagnostic or medical purposes.

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Background

Alternariol (AOH) is a toxic metabolite produced by Alternaria alternata and A. tenuissima, which grow on corn, rice, fruits, vegetables and oilseed. Mycotoxins are biologically active secondary fungal metabolites found as contaminants of food- and feedstuff [1].

Alternariol (0.8 μM) inhibited P4 secretion. Alternariol (1.6 μM) significantly reduced cell viability [1]. Alternariol (0.8 μM) reduced the expression of P450scc protein. Alternariol (1.6 μM) significantly reduced the abundance of α-tubulin and also clearly affected actin protein concentrations. Alternariol specifically inhibited P4 secretion in cultured porcine granulosa cells [1]. Twelve hours of light exposure was sufficient to decrease significantly the production of alternariol [2]. Light inhibited the production of alternariol in Alternaria alternate [2]. Alternariol was preferentially metabolized by cytochrome P450 (CYP) 1A1 and 1A2. Alternariol enhanced the levels of CYP1A1 in murine hepatoma cells (Hepa-1c1c7) but not in cells with inactivated AhR (Hepa-1c1c12) or ARNT (Hepa-1c1c4). Alternariol showed no effects on the production of reactive oxygen species but reduced cell counts in Hepa-1c1c7 cells after 24 and 48 h. At 48 h, AOH increased apoptosis dependent on AhR and ARNT [3].

References:
[1] Tiemann U, Tomek W, Schneider F, et al.  The mycotoxins alternariol and alternariol methyl ether negatively affect progesterone synthesis in porcine granulosa cells in vitro[J]. Toxicology Letters, 2009, 186(2): 139-145.
[2] Sderhll K, Svensson E, Unestam T.  Light inhibits the production of alternariol and alternariol monomethyl ether in Alternaria alternata[J]. Applied and environmental microbiology, 1978, 36(5): 655-657.
[3] Schreck I, Deigendesch U, Burkhardt B, et al.  The Alternaria mycotoxins alternariol and alternariol methyl ether induce cytochrome P450 1A1 and apoptosis in murine hepatoma cells dependent on the aryl hydrocarbon receptor[J]. Archives of toxicology, 2012, 86(4): 625-632.

Chemical Properties

Physical AppearanceA crystalline solid
StorageStore at -20°C
M.Wt258.2
Cas No.641-38-3
FormulaC14H10O5
SynonymsAOH,NSC 638263
Solubility≤0.5mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide
Chemical Name3,7,9-trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one
SDFDownload SDF
Canonical SMILESCC1=C(C2=C(C(O3)=O)C(O)=CC(O)=C2)C3=CC(O)=C1
Shipping ConditionSmall Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
General tips We do not recommend long-term storage for the solution, please use it up soon.

Quality Control

Quality Control & MSDS

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Chemical structure

Alternariol