A naphthoquinone with diverse biological activities
Related Products
Enantiomer(s)
14751Shikonin
Isomer(s)
34355Shikalkin
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Alkannin

Item No. 25058

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5,8-dihydroxy-2-[(1S)-1-hydroxy-4-methyl-3-penten-1-yl]-1,4-naphthalenedione
CAS Number
517-88-4
Synonyms
  • (–)-Alkannin
  • NSC 94524
Molecular Formula
C16H16O5
Formula Weight
288.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 5 mg/ml
λmax
215, 250, 279, 516, 555 nm
SMILES
OC1=C2C(C(C=C([C@H](C/C=C(C)/C)O)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-/m0/s1
InChi Key
NEZONWMXZKDMKF-JTQLQIEISA-N
Origin
Plant/Arnebia sinensis
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    1 mg

    $37

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    5 mg

    $81

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    10 mg

    $124

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    25 mg

    $262

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    Product Description

    Alkannin is a naphthoquinone and enantiomer of shikonin (Item No. 14751) that has been found in A. tinctoria and has diverse biological activities.1,2,3,4,5 It inhibits tumor-specific pyruvate kinase M2 (PKM2; IC50 = 0.3 μM) with 20- and 10-fold selectivity over PKM1 and pyruvate kinase L (PKL), respectively.1 Alkannin inhibits proliferation of HCT116 and SW480 colorectal cancer cells with IC50 values of 2.38 and 4.53 μM, respectively.2 It halts the cell cycle at the G1 phase and induces apoptosis in HCT116 cells when used at a concentration of 3 μM. Alkannin (1 μM) increases levels of Hsp70 in untreated and UVB-irradiated HaCaT cells as well as inhibits UVB-induced DNA fragmentation and caspase-3 activity in HaCaT cells.3 It is active against methicillin-sensitive and -resistant S. aureus (MICs = 6.25 μg/ml) as well as vancomycin-sensitive and -resistant E. faecalis (MICs = 50 and 25 μg/ml, respectively).4 Alkannin scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; Item No. 14805) radicals in a cell-free assay (EC50 = 22 ppm).5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. 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).

    2. Huu Tung, N., Du, G.-J., Wang, C.-Z., et al. Naphthoquinone components from Alkanna tinctoria (L.) Tausch show significant antiproliferative effects on human colorectal cancer cells. Phytother. Res. 27(1), 66-70 (2013).

    3. Yoshihisa, Y., Hassan, M.A., Furusawa, Y., et al. Alkannin, HSP70 inducer, protects against UVB-induced apoptosis in human keratinocytes. PLoS One 7(10), e47903 (2012).

    4. Shen, C.-C., Syu, W.-J., Li, S.-Y., et al. Antimicrobial activities of naphthazarins from Arnebia euchroma. J. Nat. Prod. 65(12), 1857-1862 (2002).

    5. Assimopoulou, A.N., and Papageorgiou, V.P. Radical scavenging activity of Alkanna tinctoria root extracts and their main constituents, hydroxynaphthoquinones. Phytother. Res. 19(2), 141-147 (2005).