A dihydrochalcone glucoside with diverse biological activities
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Trilobatin

Item No. 25837

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[4-(β-D-glucopyranosyloxy)-2,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone
CAS Number
4192-90-9
Synonyms
  • Phloretin-4-O-glucoside
Molecular Formula
C21H24O10
Formula Weight
436.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 25 mg/mlEthanol: 20 mg/mlPBS (pH 7.2): 0.1 mg/ml
λmax
225, 283 nm
SMILES
OC1=CC=C(CCC(C2=C(O)C=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C2O)=O)C=C1
InChi Code
InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-12-7-14(25)17(15(26)8-12)13(24)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-23,25-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
InChi Key
GSTCPEBQYSOEHV-QNDFHXLGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $73

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    5 mg

    $267

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    10 mg

    $356

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    Product Description

    Trilobatin is a dihydrochalcone glucoside and derivative of phloretin (Item No. 14452) that has been found in Rooibos (A. linearis) tea and has diverse biological activities.1,2,3,4,5 It reduces survival of Bel 7402 and HepG2 cancer cells when used at a concentration of 100 μM.2 Trilobatin increases superoxide dismutase (SOD) and glutathione peroxidase (GPX) activity (EC50s = 129 and 128 μM, respectively) and inhibits lipid peroxidation (IC50 = 88 μM) in rat liver homogenates.3 Pretreatment with trilobatin reduces hydrogen peroxide-induced cell death and production of mitochondrial reactive oxygen species (ROS), prevents reduction in the mitochondrial membrane potential, and increases the activity of GPX, SOD2, and isocitrate dehydrogenase 2 (IDH2) in PC12 neuronal cells.4 Trilobatin inhibits infection by various HIV-1 strains (IC50s = 2.91-27.11 μM) without inducing cytotoxicity in target cells.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Stander, M.A., Van Wyk, B.-E., Taylor, M.J.C., et al. Analysis of phenolic compounds in rooibos tea (Aspalathus linearis) with a comparison of flavonoid-based compounds in natural populations of plants from different regions. J. Agric. Food Chem. 65(47), 10270-10281 (2017).

    2. Qin, X., Xing, Y.F., Zhou, Z., et al. Dihydrochalcone compounds isolated from crabapple leaves showed anticancer effects on human cancer cell lines. Moleules 20(12), 21193-21203 (2015).

    3. Yang, W.-M., Liu, J.-K., Qin, X.-D., et al. Antioxidant activities of three dihydrochalcone glucosides from leaves of Lithocarpus pachyphyllus. Z. Naturforsch. C. 59(7-8), 481-484 (2004).

    4. Gao, J., Liu, S., Xu, F., et al. Trilobatin protects against oxidative injury in neuronal PC12 cells through regulating mitochondrial ROS homeostasis mediated by AMPK/Nrf2/Sirt3 signaling pathway. Front. Mol. Neurosci. 11:267, (2018).

    5. Yin, S., Zhang, X., Lai, F., et al. Trilobatin as an HIV-1 entry inhibitor targeting the HIV-1 Gp41 envelope. FEBS Lett. 592(13), 2361-2377 (2018).