A flavonoid with anticancer and vasorelaxant activities
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Trifolirhizin

Item No. 34655

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
β-D-glucopyranoside, 6aR,12aR-dihydro-6H-[1,3]dioxolo[5,6]benzofuro[3,2-c][1]benzopyran-3-yl
CAS Number
6807-83-6
Synonyms
  • (–)-Maackiain-3-O-glucoside
  • Sophojaponicin B1
Molecular Formula
C22H22O10
Formula Weight
446.4
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetone: SolubleMethanol: Slightly soluble
SMILES
[H][C@]1(C2=CC(OCO3)=C3C=C2O4)[C@]4([H])C5=CC=C(C=C5OC1)O[C@@H]6O[C@@H]([C@H]([C@@H]([C@H]6O)O)O)CO
InChi Code
InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2/t12-,17+,18+,19-,20+,21-,22+/m0/s1
InChi Key
VGSYCWGXBYZLLE-QEEQPWONSA-N
Origin
Plant/Trifolium pratense
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $37

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    10 mg

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    25 mg

    $493

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    Cayman Chemical
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    Product Description

    Trifolirhizin is a flavonoid that has been found in S. flavescens and has anticancer and vasorelaxant activities.1,2 It induces the accumulation of LC3 puncta, a marker of autophagy, in HCT116 and SW620 cells, as well as inhibits proliferation of B16/F10 murine melanoma and human A2780 ovarian and MKN45 gastric cancer cells when used at a concentration of 20 µM.1 Trifolirhizin (10 m/kg) induces intratumor apoptosis and necrosis and reduces tumor weight and volume in a colorectal cancer mouse xenograft model. It also induces relaxation in precontracted isolated mouse aortic rings in a β2-adrenergic receptor-independent manner when used at concentrations ranging from 0.2 to 20 µg/ml.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sun, D., Tao, W., Zhang, F., et al. Trifolirhizin induces autophagy-dependent apoptosis in colon cancer via AMPK/mTOR signaling. Signal Transduct. Target. Ther. 5(1), 174 (2020).

    2. Yang, N., Liang, B., Srivastava, K., et al. The Sophora flavescens flavonoid compound trifolirhizin inhibits acetylcholine induced airway smooth muscle contraction. Phytochemistry 95, 259-267 (2013).