An anthraquinone with diverse biological activities
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Aurantioobtusin

Item No. 27481

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,3,7-trihydroxy-2,8-dimethoxy-6-methyl-9,10-anthracenedione
CAS Number
67979-25-3
Molecular Formula
C17H14O7
Formula Weight
330.3
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/ml
λmax
287, 389 nm
SMILES
OC1=C(OC)C(O)=C(C(C(C(OC)=C(O)C(C)=C2)=C2C3=O)=O)C3=C1
InChi Code
InChI=1S/C17H14O7/c1-6-4-7-11(17(24-3)12(6)19)14(21)10-8(13(7)20)5-9(18)16(23-2)15(10)22/h4-5,18-19,22H,1-3H3
InChi Key
RNXZPKOEJUFJON-UHFFFAOYSA-N
Origin
Plant/Cassia tora Linn.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $72

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    5 mg

    $215

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    10 mg

    $358

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    25 mg

    $626

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    Product Description

    Aurantioobtusin is an anthraquinone originally isolated from Cassia seeds with diverse biological activities.1,2,3,4,5 It inhibits rat lens aldose reductase (RLAR) in vitro (IC50 = 13.6 μM).1 Aurantioobtusin (10 and 100 μM) activates the aryl hydrocarbon receptor (AhR) in a concentration-dependent manner.2 It inhibits rat platelet aggregation induced by arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607), ADP, and collagen.3 Aurantioobtusin induces vasorelaxation in isolated precontracted rat mesenteric artery rings, an effect that is inhibited by the PI3K inhibitor LY290042 or inhibition of endothelial nitric oxide synthase (eNOS).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Jang, D.S., Lee, G.Y., Kim, Y.S., et al. Anthraquinones from the seeds of Cassia tora with inhibitory activity on protein glycation and aldose reductase. Biol. Pharm. Bull. 30(11), 2207-2210 (2007).

    2. Amakura, Y., Yoshimura, M., Takaoka, M., et al. Characterization of natural aryl hydrocarbon receptor agonists from cassia seed and rosemary. Molecules 19(4), 4956-4966 (2014).

    3. Yun-Choi, H.S., Kim, J.H., and Takido, M. Potential inhibitors of platelet aggregation from plant sources, V. Anthraquinones from seeds of Cassia obtusifolia and related compounds. J. Nat. Prod. 53(3), 630-633 (1990).

    4. Li, S., Li, Q., Lv, X., et al. Aurantio-obtusin relaxes systemic arteries through endothelial PI3K/AKT/eNOS-dependent signaling pathway in rats. J. Pharmacol. Sci. 128(3), 108-115 (2015).

    5. Mbatchou, V.C., Tchouassi, D.P., Dickson, R.A., et al. Mosquito larvicidal activity of Cassia tora seed extract and its key anthraquinones aurantio-obtusin and obtusin. Parasit. Vectors 10(1), 562 (2017).