A pentahydroanthraquinone with diverse biological activities
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Isomer(s)
27466Bostrycin
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Altersolanol A

Item No. 44642

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1R,2S,3R,4S-tetrahydro-1,2,3,4,5-pentahydroxy-7-methoxy-2-methyl-9,10-anthracenedione
CAS Number
22268-16-2
Synonyms
  • NSC 173943
Molecular Formula
C16H16O8
Formula Weight
336.3
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: Slightly soluble: 0.1-1 mg/mlWater: Slightly soluble: 0.1-1 mg/ml
SMILES
O[C@H]1C2=C(C(C3=CC(OC)=CC(O)=C3C2=O)=O)[C@@H](O)[C@@](O)(C)[C@@H]1O
InChi Code
InChI=1S/C16H16O8/c1-16(23)14(21)10-9(13(20)15(16)22)12(19)8-6(11(10)18)3-5(24-2)4-7(8)17/h3-4,13-15,17,20-23H,1-2H3/t13-,14+,15+,16-/m0/s1
InChi Key
VSMBLBOUQJNJIL-JJXSEGSLSA-N
Origin
Fungus/Sarocladium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $145

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    Product Description

    Altersolanol A is a pentahydroanthraquinone originally isolated from A. solani that has diverse biological activities.1,2,3,4 It is an activator of mitochondrial NADH oxidase and increases the activity of mitochondrial NADH oxidase isolated from primary tobacco cells (N. rustica).2 Altersolanol A is cytotoxic to L5178Y lymphoma cells (IC50 = 2.53 µM).3 It induces cell cycle arrest in the sub-G1 phase, decreases TNF-α-induced NF-κB transcriptional activity, and reduces cell migration and invasion in K562 chronic myeloid leukemia (CML) cells when used at a concentration of 25 µM.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Stoessl, S. Some metabolites of Alternaria solani. Can. J. Chem. 47(5), 767-776 (1969).

    2. Haraguchi, H., Abo, T., Fukuda, A., et al. Mode of phytotoxic action of altersolanols. Phytochem. 43(5), 989-992 (1996).

    3. Liu, Y., Marmann, A., Abdel-Aziz, M.S., et al. Tetrahydroanthraquinone derivatives from the endophytic fungus Stemphylium globuliferum. Eur. J. Org. Chem. 2015(12), 2646-2653 (2015).

    4. Teiten, M.-H., Mack, F., Debbab, A., et al. Anticancer effect of altersolanol A, a metabolite produced by the endophytic fungus Stemphylium globuliferum, mediated by its pro-apoptotic and anti-invasive potential via the inhibition of NF-κB activity. Bioorg. Med. Chem. 21(13), 3850-3858 (2013).