A biflavonoid with diverse biological activities
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Amentoflavone

Item No. 21779

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
8-[5-(5,7-dihydroxy-4-oxo-4H-1-benzopyran-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
CAS Number
1617-53-4
Synonyms
  • Didemethyl Ginkgetin
  • NSC 295677
Molecular Formula
C30H18O10
Formula Weight
538.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMF:PBS (pH 7.2) (1:4): 0.1 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/ml
λmax
269, 335 nm
SMILES
O=C1C=C(C2=CC=C(O)C=C2)OC3=C1C(O)=CC(O)=C3C4=CC(C5=CC(C(C(O)=CC(O)=C6)=C6O5)=O)=CC=C4O
InChi Code
InChI=1S/C30H18O10/c31-15-4-1-13(2-5-15)24-12-23(38)29-21(36)10-20(35)27(30(29)40-24)17-7-14(3-6-18(17)33)25-11-22(37)28-19(34)8-16(32)9-26(28)39-25/h1-12,31-36H
InChi Key
YUSWMAULDXZHPY-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    10 mg

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    25 mg

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    Product Description

    Amentoflavone is a biflavonoid originally isolated from Selaginella. It has a wide variety of biological effects including antibacterial, antioxidant, antiviral, antidiabetic, and neuroprotective activities.1,2,3,4 Amentoflavone has antiviral activity against the influenza A subtypes H1N1 and H3N2, influenza B, and herpes simplex virus 1 (EC50s = 3.1 and 4.3, 0.56, and 17.9 µg/ml, respectively).5 It has antidiabetic effects such that it dose-dependently increases insulin receptor phosphorylation and activation and inhibits hydrolysis of p-nitrophenyl phosphate (p-NPP) catalyzed by protein tyrosine phosphatase 1B (PTP1B; IC50 = 7.3 µM).6 Amentoflavone reduces the time mice spend immobile in the forced swim test, a measure of antidepressant efficacy, in a dose-dependent manner.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hwang, J.H., Choi, H., Woo, E.-R., et al. Antibacterial effect of amentoflavone and its synergistic effect with antibiotics. J. Microbiol. Biotechnol. 23(7), 953-958 (2013).

    2. Yu, S., Yan, H., Zhang, L., et al. A Review on the phytochemistry, pharmacology, and pharmacokinetics of amentoflavone, a naturally-occurring biflavonoid. Molcecules 16;22(2), (2017).

    3. Lee, S., Kim, H., Kang, J.-W., et al. The biflavonoid amentoflavone induces apoptosis via suppressing E7 expression, cell cycle arrest at sub-G₁ phase, and mitochondria-emanated intrinsic pathways in human cervical cancer cells. J. Med. Chem. 14(7), 808-816 (2011).

    4. Zhang, Z., Sun, T., Niu, J.-g., et al. Amentoflavone protects hippocampal neurons: anti-inflammatory, antioxidative, and antiapoptotic effects. Neural. Regen. Res. 10(7), 1125-1133 (2015).

    5. Lin, Y.-M., Flavin, M.T., Schure, R., et al. Antiviral activities of biflavonoids. Planta. Med. 65(2), 120-125 (1999).

    6. Na, M., Kim, K.A., Oh, H., et al. Protein tyrosine phosphatase 1B inhibitory activity of amentoflavone and its cellular effect on tyrosine phosphorylation of insulin receptors. Biol. Pharm. Bull. 30(2), 379-381 (2007).

    7. Ishola, I.O., Chatterjee, M., Tota, S., et al. Antidepressant and anxiolytic effects of amentoflavone isolated from Cnestis ferruginea in mice. Pharmacol. Biochem. Behav. 103(2), 322-331 (2012).