An anthroquinone derivative
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Hypericin

Item No. 11334

Technical Information
Formal Name
1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-phenanthro[1,10,9,8-opqra]perylene-7,14-dione
CAS Number
548-04-9
Synonyms
  • NSC 407313
Molecular Formula
C30H16O8
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH 7.2) (1:3): 0.25 mg/mlEthanol: slightly soluble
λmax
217, 286, 328, 385, 476, 511, 548, 591 nm
SMILES
CC1=C(C2=C3C(O)=C1)C4=C(C)C=C(O)C5=C4C6=C2C(C(C7=C(O)C=C(O)C(C5=O)=C76)=C(O)C=C8O)=C8C3=O
InChi Code
InChI=1S/C30H16O8/c1-7-3-9(31)19-23-15(7)16-8(2)4-10(32)20-24(16)28-26-18(12(34)6-14(36)22(26)30(20)38)17-11(33)5-13(35)21(29(19)37)25(17)27(23)28/h3-6,31-36H,1-2H3
InChi Key
BTXNYTINYBABQR-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    An anthroquinone derivative that is naturally found in the flower of H. perforatum (St. John’s wort) and has antidepressant, antiviral, and anticancer activities.1,2 Hypericin inhibits neuronal uptake of serotonin, norepinephrine, dopamine, GABA and L-glutamate, contributing to its antidepressant effects.3 It exerts broad spectrum phototoxic affects (IC50 = 140 - 1,570 nM) through induction of apoptotic signaling and formation of reactive oxygen species (ROS) in cancer cells.4 Hypericin also has in vitro activity, which can be enhanced with photo-activation, against a variety of viruses including HIV, influenza virus, hepatitis C, murine cytolomegalovirus, and herpes viruses.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wölfle, U., Seelinger, G., and Schempp, C.M. Topical application of St. John’s wort (Hypericum perforatum). Planta Med. 80(2-3), 109-120 (2014).

    2. Jendželovská, Z., Jendželovský, R., Kuchárová, B., et alHypericin in the light and in the dark: Two sides of the same coin. Front. Plant Sci. 7(560), (2016).

    3. Butterweck, V., Christoffel, V., Nahrstedt, A., et alStep by step removal of hyperforin and hypericin: Activity profile of different Hypericum preparations in behavioral models. Life Sci. 73(5), 627-639 (2003).

    4. Momekov, G.F., D., Zheleva-Dimitrova, D., Nedialkov, P., et alCytotoxic effects of hyperatomarin, a prenylated phloroglucinol from Hypericum annulatum Moris subsp. annulatum, in a panel of malignant cell lines. Phytomedicine 15(11), 1010-1015 (2008).

    5. Jacobson, J.M., Feinman, L., Liebes, L., et alPharmacokinetics, safety, and antiviral effects of hypericin, a derivative of St. John’s wort plant, in patients with chronic hepatitis C virus infection. Antimicrob. Agents and Chemother. 45(2), 517-524 (2001).