A flavonoid glycoside with diverse biological activities
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Avicularin

Item No. 33918

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(α-L-arabinofuranosyloxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
CAS Number
572-30-5
Synonyms
  • Quercetin 3-O-α-L-arabinofuranoside
Molecular Formula
C20H18O11
Formula Weight
434.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 30 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): insolu
λmax
258, 359 nm
SMILES
O=C(C(O[C@@H]1O[C@@H](CO)[C@H](O)[C@H]1O)=C(C2=CC(O)=C(C=C2)O)OC3=CC(O)=C4)C3=C4O
InChi Code
InChI=1S/C20H18O11/c21-6-13-15(26)17(28)20(30-13)31-19-16(27)14-11(25)4-8(22)5-12(14)29-18(19)7-1-2-9(23)10(24)3-7/h1-5,13,15,17,20-26,28H,6H2/t13-,15-,17+,20-/m0/s1
InChi Key
BDCDNTVZSILEOY-UXYNSRGZSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $54

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    5 mg

    $250

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    10 mg

    $341

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    25 mg

    $783

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    Cayman Chemical
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    Product Description

    Avicularin is a flavonoid glycoside that has been found in R. sachalinensis and has diverse biological activities.1,2,3,4,5 It inhibits fatty acid synthase (FASN) and aldose reductase (IC50s = 6.15 and 19.05 µM for the chicken liver and human enzymes, respectively).1,2 Avicularin scavenges DPPH and superoxide radicals, as well as inhibits copper-induced oxidation of LDL in cell-free assays (IC50s = 64.3, 6, and 3.8 µM, respectively).3 It inhibits LPS-induced increases in nitric oxide (NO) and prostaglandin E2 (PGE2; Item No. 14010) production in RAW 264.7 macrophages when used at concentrations ranging from 30 to 300 µM.4 Avicularin (100 µg/ml) inhibits the proliferation, migration, and invasion of, as well as induces apoptosis and cell cycle arrest at the G0/G1 phase in, Huh7 hepatocellular carcinoma cells.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Abramson, H.N. The lipogenesis pathway as a cancer target. J. Med. Chem. 54(16), 5615-5638 (2011).

    2. Naeem, S., Hylands, P., and Barlow, D. Construction of an Indonesian herbal constituents database and its use in Random Forest modelling in a search for inhibitors of aldose reductase. Bioorg. Med. Chem. 20(3), 1251-1258 (2012).

    3. Zhang, X., Thuong, P.T., Jin, W., et al. Antioxidant activity of anthraquinones and flavonoids from flower of Reynoutria sachalinensis. Arch. Pharm. Res. 28(1), 22-27 (2005).

    4. Vo, V.A., Lee, J.-W., Chang, J.-E., et al. Avicularin inhibits lipopolysaccharide-induced inflammatory response by suppressing ERK phosphorylation in RAW 264.7 macrophages. Biomol. Ther. (Seoul) 20(6), 532-537 (2012).

    5. Wang, Z., Li, F., Quan, Y., et al. Avicularin ameliorates human hepatocellular carcinoma via the regulation of NF‑κB/COX‑2/PPAR‑γ activities. Mol. Med. Rep. 19(6), 5417-5423 (2019).