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S7576 Sigma

Shikonin

≥98% (HPLC)

Synonym: (±)-Alkannin, (±)-Shikalkin, (±)-Shikonin, (±)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone

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Properties

Related Categories Cell Biology, Nutrition Research, Phenols, Phytochemicals by Chemical Classification, Phytochemicals in Herbal Medicine or Traditional Chinese Medicine (TCM) More...
assay   ≥98% (HPLC)
form   powder or solid
color   red to brown
solubility   methanol: soluble1 mg/mL
storage temp.   2-8°C

Description

Packaging

10 mg in glass bottle

50 mg in poly bottle

Biochem/physiol Actions

Naphthoquinone isolated from Arnebia sp. Used as an anti-inflammatory treatment in traditional chinese medicine (TCM). Inhibits chemokine receptor function and suppresses HIV-1.† Circumvents cancer drug resistance by induction of cell death through a necroptotic pathway.† Treatment of cancer cells with shikonin suppressed glycolysis via the inhibition of pyruvate kinase M2 (PKM2).

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Articles

Oncogenes and Tumor Suppressors Reprogram Metabolism

Proliferating cells require the biosynthesis of structural components for biomass production and for genomic replication. This requires a reprogramming of the metabolic pathways to ensure nutrients s...
Keywords: Aerobic, Antitumor agents, Apoptosis, Biofiles, Cancer, Citric Acid Cycle, Degradations, Environmental, Events, Gene expression, Glycolysis, Growth factors, Metabolic Pathways, Metabolism, Metabolites, Nucleotide Synthesis, PAGE, Pentose phosphate pathway, Phosphorylations, Support

Traditional Medicinals and Cancer

Traditional Chinese Medicine (TCM) is a healing art that has been practiced for thousands of years. The practice of TCM is a holistic approach that includes the use of herbal preparations, acupunctur...
Lynn Stephenson, Product Specialist, Sigma® Life Science and Chloe McClanahan, Product Manager, Sigma Life Science
Biofiles Vol. 8, No. 6
Keywords: Analgesics, Antitumor agents, Apoptosis, Cancer, Drug discovery, Fractionation, High performance liquid chromatography, Metabolites, Metabolomics, Nuclear magnetic resonance spectroscopy, Pharmaceutical

Peer-Reviewed Papers

References

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Ferroxitosis: A cell death from modulation of oxidative phosphorylation and PKM2-dependent glycolysis in melanoma. Lakhter AJ, Hamilton J, Dagher PC, et al. Oncotarget 5(24), 12694-703, (2014)

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Shikonin and its analogs inhibit cancer cell glycolysis by targeting tumor pyruvate kiase-M2. Chen, J. et al. Oncogene 30, 4297-4306, (2011)

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

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

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Shikonin induces immunogenic cell death in tumor cells and enhances dendritic cell-based cancer vaccine. Chen HM, Wang PH, Chen SS, et al. Cancer Immunol. Immunother. 61(11), 1989-2002, (2012)

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[Tissue cultures of Lithospermum erythrorhizon and biosynthesis of shikonin derivatives]. Fan HX and Zhu WH Yao Xue Xue Bao 23(9), 716-20, (1988)

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[Growth and accumulation of shikonin compounds of two kinds of cells in suspension culture of Arnebia euchroma]. Wang S, Xie T, Ye HC, et al. Zhongguo Zhong Yao Za Zhi 38(8), 1138-44, (2013)

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[Compare the composition and content of Arnebiae radix and the stem residues]. Zhou J, Tang XM, Wang C, et al. Zhong Yao Cai 35(3), 361-6, (2012)

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[Antitumor effect research progress of shikonin and its derivatives]. Zhu MY, Wang RB, Zhou W, et al. Yao Xue Xue Bao 47(5), 588-93, (2012)

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[Rationality for dynamic detection of shikonin of Arnerbia euchroma in industrial process]. Wei YJ, Wang M, Xu QF, et al. Zhong Yao Cai 34(7), 1129-33, (2011)

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In vitro and in vivo anticancer effects of Lithospermum erythrorhizon extract on B16F10 murine melanoma. Rajasekar S, Park da J, Park C, et al. J. Ethnopharmacol. 144(2), 335-45, (2012)

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Shikonin ameliorates cerulein-induced acute pancreatitis in mice. Xiong J, Ni J, Hu G, et al. J. Ethnopharmacol. 145(2), 573-80, (2013)

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Novel multiple apoptotic mechanism of shikonin in human glioma cells. Chen CH, Lin ML, Ong PL, et al. Ann. Surg. Oncol. 19(9), 3097-106, (2012)

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Shikonin, a Chinese plant-derived naphthoquinone, induces apoptosis in hepatocellular carcinoma cells through reactive oxygen species: A potential new treatment for hepatocellular carcinoma. Gong K and Li W Free Radic. Biol. Med. 51(12), 2259-71, (2011)

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Shikonin suppresses tumor growth and synergizes with gemcitabine in a pancreatic cancer xenograft model: Involvement of NF-κB signaling pathway. Wang Y, Zhou Y, Jia G, et al. Biochem. Pharmacol. 88(3), 322-33, (2014)

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Chimeric advanced drug delivery nano systems (chi-aDDnSs) for shikonin combining dendritic and liposomal technology. Kontogiannopoulos KN, Assimopoulou AN, Hatziantoniou S, et al. Int. J. Pharm. 422(1-2), 381-9, (2012)

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Chemical inducers of heat shock proteins derived from medicinal plants and cytoprotective genes response. Ahmed K, Furusawa Y, Tabuchi Y, et al. Int. J. Hyperthermia 28(1), 1-8, (2012)

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Shikonin enhances efficacy of a gene-based cancer vaccine via induction of RANTES. Chen HM, Wang PH, Aravindaram K, et al. J. Biomed. Sci. 19, 42, (2012)

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Traditional chinese medicine remedy to jury: the pharmacological basis for the use of shikonin as an anticancer therapy. Andújar I, Recio MC, Giner RM, et al. Curr. Med. Chem. 20(23), 2892-8, (2013)

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Shikonin attenuates lung cancer cell adhesion to extracellular matrix and metastasis by inhibiting integrin β1 expression and the ERK1/2 signaling pathway. Wang H, Wu C, Wan S, et al. Toxicology 308, 104-12, (2013)

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Shikonin and its derivatives: a patent review. Wang R, Yin R, Zhou W, et al. Expert Opin. Ther. Pat. 22(9), 977-97, (2012)

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PKM2 inhibitor shikonin suppresses TPA-induced mitochondrial malfunction and proliferation of skin epidermal JB6 cells. Li W, Liu J, and Zhao Y Mol. Carcinog. 53(5), 403-12, (2014)

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Cellular pharmacology studies of shikonin derivatives. Chen X, Yang L, Oppenheim JJ, et al. Phytother Res. 16(3), 199-209, (2002)

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Quinones derived from plant secondary metabolites as anti-cancer agents. Lu JJ, Bao JL, Wu GS, et al. Anticancer Agents Med. Chem. 13(3), 456-63, (2013)

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Anticancer agent shikonin is an incompetent inducer of cancer drug resistance. Wu H, Xie J, Pan Q, et al. PLoS ONE 8(1), e52706, (2013)

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Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin. He H, Bai LP, and Jiang ZH Bioorg. Med. Chem. Lett. 22(4), 1582-6, (2012)

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Selective and slow-binding inhibition of shikonin derivatives isolated from Lithospermum erythrorhizon on glycosyl hydrolase 33 and 34 sialidases. Kim JY, Jeong HJ, Park JY, et al. Bioorg. Med. Chem. 20(5), 1740-8, (2012)

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Shikonin attenuates lipopolysaccharide-induced acute lung injury in mice. Bai GZ, Yu HT, Ni YF, et al. J. Surg. Res. 182(2), 303-11, (2013)

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The critical role of redox homeostasis in shikonin-induced HL-60 cell differentiation via unique modulation of the Nrf2/ARE pathway. Zhang B, Chen N, Chen H, et al. Oxid. Med. Cell. Longev. 2012, 781516, (2012)

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The molecular mechanisms and gene expression profiling for shikonin-induced apoptotic and necroptotic cell death in U937 cells. Piao JL, Cui ZG, Furusawa Y, et al. Chem. Biol. Interact. 205(2), 119-27, (2013)

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Compounds from Arnebia euchroma and their related anti-HCV and antibacterial activities. Li HM, Tang YL, Zhang ZH, et al. Planta Med. 78(1), 39-45, (2012)

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Inhibitory effect of Shikonin on Candida albicans growth. Miao H, Zhao L, Li C, et al. Biol. Pharm. Bull. 35(11), 1956-63, (2012)

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Screening for novel quorum-sensing inhibitors to interfere with the formation of Pseudomonas aeruginosa biofilm. Ding X, Yin B, Qian L, et al. J. Med. Microbiol. 60(Pt 12), 1827-34, (2011)

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Optimization of shikonin homogenate extraction from Arnebia euchroma using response surface methodology. Liu T, Ma C, Yang L, et al. Molecules 18(1), 466-81, (2013)

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Glutathione-S-transferase enhances proliferation-migration and protects against shikonin-induced cell death in breast cancer cells. He S, Liao TT, Chen YT, et al. Kaohsiung J. Med. Sci. 27(11), 477-84, (2011)

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Ionization of shikonin derivatives using negative-ion electrospray mass spectrometry: [M-H]- versus [M + e]•-. Zhang Y, Xiao S, Li X, et al. J. Mass Spectrom. 47(5), 581-5, (2012)

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