A natural product with anti-inflammatory and anti-tumor activity
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Enantiomer(s)
25058Alkannin
Isomer(s)
34355Shikalkin
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Shikonin

Item No. 14751

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,8-dihydroxy-2-[(1R)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthalenedione
CAS Number
517-89-5
Synonyms
  • C.I. 75535
  • Isoarnebin 4
  • NSC 252844
Molecular Formula
C16H16O5
Formula Weight
288.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 16 mg/mlDMF:PBS (pH 7.2) (1:5): 0.16 mg/mlDMSO: 11 mg/mlEthanol: 2 mg/ml
λmax
214, 278, 515 nm
SMILES
OC1=C2C(C(C=C([C@@](O)([H])C/C=C(C)\C)C2=O)=O)=C(O)C=C1
InChi Code
InChI=1S/C16H16O5/c1-8(2)3-4-10(17)9-7-13(20)14-11(18)5-6-12(19)15(14)16(9)21/h3,5-7,10,17-19H,4H2,1-2H3/t10-/m1/s1
InChi Key
NEZONWMXZKDMKF-SNVBAGLBSA-N
Origin
Plant/Arnebiae radix
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $36

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    10 mg

    $63

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    50 mg

    $203

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    100 mg

    $369

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Shikonin is a naturally occurring naphthoquinine isolated from the dried root of L. erythrorhizon, an herb used in traditional Chinese medicine. It increases glucose uptake by adipocytes and myocytes and inhibits the activity of phosphatase and tensin homolog (PTEN; IC50 = 2.7 µM).1,2 It inhibits glycolysis in cancer cells by inhibiting tumor-specific pyruvate kinase M2 (IC50 = 0.3 µM).3 Shikonin induces cell death consistent with necroptosis in MCF-7 and HEK293 cancer cell lines.4 It inhibits leukocyte migration, downregulates chemokine receptor expression, and inhibits HIV-1 replication at nanomolar concentrations.5 Shikonin exhibits anti-inflammatory activity, reducing joint swelling and cartilage destruction in a mouse model of collagen-induced arthritis.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kamei, R., Kitagawa, Y., Kadokura, M., et al. Shikonin stimulates glucose uptake in 3T3-L1 adipocytes via an insulin-independent tyrosine kinase pathway. Biochem. Biophys. Res. Commun. 292(3), 642-651 (2002).

    2. Nigorikawa, K., Yoshikawa, K., Sasaki, T., et al. A naphthoquinone derivative, shikonin, has insulin-like actions by inhibiting both phosphatase and tensin homolog deleted on chromosome 10 and tyrosine phosphatases. Mol. Pharmacol. 70(3), 1143-1149 (2006).

    3. Chen, J., Xie, J., Jiang, Z., et al. Shikonin and its analogs inhibit cancer cell glycolysis by targeting tumor pyruvate kinase-M2. Oncogene 30(42), 4297-4306 (2011).

    4. Han, W., Li, L., Qiu, S., et al. Shikonin circumvents cancer drug resistance by induction of a necroptotic death. Mol. Cancer Ther. 6(5), 1641-1649 (2007).

    5. Chen, X., Yang, L., Zhang, N., et al. Shikonin, a component of chinese herbal medicine, inhibits chemokine receptor function and suppresses human immunodeficiency virus type 1. Antimicrob. Agents Chemother. 47(9), 2810-2816 (2003).

    6. Kim, Y.O., Hong, S.J., and Yim, S.V. The efficacy of shikonin on cartilage protection in a mouse model of rheumatoid arthritis. Korean J. Physiol. Pharmacol. 14(4), 199-204 (2010).