Shikonin

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). It inhibits glycolysis in cancer cells by inhibiting tumor-specific pyruvate kinase M2 (IC50 = 0.3 µM). Shikonin induces cell death consistent with necroptosis in MCF-7 and HEK293 cancer cell lines. It inhibits leukocyte migration, downregulates chemokine receptor expression, and inhibits HIV-1 replication at nanomolar concentrations. Shikonin exhibits anti-inflammatory activity, reducing joint swelling and cartilage destruction in a mouse model of collagen-induced arthritis.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: DMF: 16 mg/ml, DMF:PBS (pH 7.2) (1:5): 0.16 mg/ml, DMSO: 11 mg/ml, Ethanol: 2 mg/ml. lambdamax: 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.