A flavonoid glycoside with diverse biological activities
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Vicenin-2

Item No. 33403

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6,8-di-β-D-glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
23666-13-9
Synonyms
  • Vicenin II
  • Violantin
Molecular Formula
C27H30O15
Formula Weight
594.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
λmax
218, 274, 335 nm
SMILES
OC[C@H]([C@H]([C@@H]([C@H]1O)O)O)O[C@H]1C2=C3OC(C4=CC=C(O)C=C4)=CC(C3=C(O)C([C@H]5[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O5)=C2O)=O
InChi Code
InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2/t12-,13-,17-,18-,21+,22+,23-,24-,26+,27+/m1/s1
InChi Key
FIAAVMJLAGNUKW-VQVVXJKKSA-N
Origin
Plant/Desmodium styracifolium
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

    $162

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    10 mg

    $244

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    25 mg

    $472

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    Product Description

    Vicenin-2 is a polyketide synthase-derived flavonoid glycoside that has been found in C. subternata and has diverse biological activities.1,2,3,4,5 It inhibits thrombin-induced aggregation of isolated mouse platelets when used at concentrations ranging from 2 to 30 µM, as well as increases tail bleeding time in mice when administered at a dose of 35.7 µg/animal.2 Vicenin-2 (1 mg/kg) reduces tumor growth in a PC3 prostate cancer mouse xenograft model.3 It decreases trabecular separation, as well as increases trabecular thickness and area, in an ovariectomized rat model of osteoporosis.4 Vicenin-2 (50 mg/kg) decreases ulceration and increases colon weight and length in a mouse model of colitis induced by dextran sulfate (DSS; Item No. 23250).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kitamura, K., Ando, Y., Matsumoto, T., et al. Total synthesis of aryl C-glycoside natural products: Strategies and tactics. Chem. Rev. 118(4), 1495-1598 (2018).

    2. Lee, W., and Bae, J.-S. Antithrombotic and antiplatelet activities of vicenin-2. Blood Coagul. Fibrinolysis 26(6), 628-634 (2015).

    3. Nagaprashantha, L.D., Vatsyayan, R., Singhal, J., et al. Anti-cancer effects of novel flavonoid vicenin-2 as a single agent and in synergistic combination with docetaxel in prostate cancer. Biochem. Pharmacol. 82(9), 1100-1109 (2011).

    4. Zhang, Z., Zhao, Q., Liu, T., et al. Effect of vicenin-2 on ovariectomy-induced osteoporosis in rats. Biomed. Pharmacother. 129, 110474 (2020).

    5. Yin, Y., Ye, L., Niu, Z., et al. Anti-inflammatory effects of Vicenin-2 on dextran sulfate sodium-induced colitis in mice. Drug Dev. Res. 80(5), 546-555 (2019).