A biflavonoid with diverse biological activities
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3,8'-Biapigenin

Item No. 34143

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,5′,7,7′-tetrahydroxy-2,2′-bis(4-hydroxyphenyl)-[3,8′-bi-4H-1-benzopyran]-4,4′-dione
CAS Number
101140-06-1
Synonyms
  • I3,II8-Biapigenin
  • 3,8"-Biapigenin
Molecular Formula
C30H18O10
Formula Weight
538.5
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Alcohol: soluble
SMILES
O=C1C=C(C2=CC=C(O)C=C2)OC3=C1C(O)=CC(O)=C3C4=C(C5=CC=C(O)C=C5)OC6=C(C(O)=CC(O)=C6)C4=O
InChi Code
InChI=1S/C30H18O10/c31-15-5-1-13(2-6-15)22-12-21(37)24-19(35)11-20(36)26(30(24)39-22)27-28(38)25-18(34)9-17(33)10-23(25)40-29(27)14-3-7-16(32)8-4-14/h1-12,31-36H
InChi Key
IQAMTZLKUHMPPE-UHFFFAOYSA-N
Origin
Plant/Unidentified sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    3,8'-Biapigenin is a polyketide synthase-derived biflavonoid that has been found in Hypericum and has diverse biological activities.1,2,3,4,5 It inhibits protein tyrosine phosphatase 1B (PTP1B; IC50 = 4.5 µM) and stimulates glucose uptake in 3T3-L1 adipocyte cells when used at concentrations of 5 and 10 µM.2 3,8'-Biapigenin inhibits the cytochrome P450 (CYP) isoforms CYP3A4, CYP2C9, and CYP1A2 (Kis = 0.038, 0.32, and 0.95 µM, respectively).3 It reverses cell death induced by kainate and NMDA in isolated rat embryonic hippocampal neurons when used at a concentration of 10 µM.4 3,8'-Biapigenin (8 mg/kg) decreases carrageenan-induced paw edema and protects against gastric lesions induced by indomethacin (Item No. 70270) in rats.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Weng, J.-K., and Noel, J.P. Chemodiversity in Selaginella: A reference system for parallel and convergent metabolic evolution in terrestrial plants. Front. Plant Sci. 4, 119 (2013).

    2. Nguyen, P.-H., Ji, D.-J., Han, Y.-R., et al. Selaginellin and biflavonoids as protein tyrosine phosphatase 1B inhibitors from Selaginella tamariscina and their glucose uptake stimulatory effects. Bioorg. Med. Chem. 23(13), 3730-3737 (2015).

    3. Obach, R.S. Inhibition of human cytochrome P450 enzymes by constituents of St. John’s wort, an herbal preparation used in the treatment of depression. J. Pharmacol. Exp. Ther. 294(1), 88-95 (2000).

    4. Silva, B., Oliveira, P.J., Dias, A.S., et al. Quercetin, kaempferol and biapigenin from Hypericum perforatum are neuroprotective against excitotoxic insults. Neurotox. Res. 13(3-4), 265-279 (2008).

    5. Zdunić, G., Gođevac, D., Milenković, M., et al. Evaluation of Hypericum perforatum oil extracts for an antiinflammatory and gastroprotective activity in rats. Phytother. Res. 23(11), 1559-1564 (2009).