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ProductsBack/Shikonin [517-89-5]
Chemical Structure
Chemical Structure
Chemical Structure

Shikonin [517-89-5]

Research Use Only
AG-CN2-0487
AdipoGen Life Sciences
CAS Number517-89-5
DownloadMSDS
Product group Chemicals
Estimated Purity>98%
Molecular Weight288.3
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Shikonin [517-89-5]
  • Delivery Days Customer
    10
  • CAS Number
    517-89-5
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Hazard Information
    Warning
  • Molecular Formula
    C16H16O5
  • Molecular Weight
    288.3
  • Scientific Description
    Anticancer compound. Inhibits TNF-alpha-induced and B-16 melanoma-induced angiogenesis. Induces apoptosis and RIP1- and RIP3-dependent necroptosis in several cancer cells. Circumvents cancer antidrug resistance through the necroptosis pathway. Proteasome inhibitor. Autophagy inducer. Topoisomerase I inhibitor. Inhibits glycolysis in cancer cells by inhibiting tumor-specific pyruvate kinase M2 (PKM2). Anti-inflammatory compound. Inhibits leukocyte migration, downregulates chemokine receptor expression, and inhibits HIV-1 replication. Inhibits the activation of NLRP3 and AIM2 inflammasome. Shown to directly target caspase-1 and as a inhibitor of PKM2 to block PKM2-mediated glycolysis that promotes inflammasome activation by modulating EIF2AK2 phosphorylation in macrophages. Antioxidant. Free radical scavenger. Directly inhibits nitric oxide synthase (NOS). Regulator of systemic glucose tolerance, energy balance and adiposity/obesity. Adipogenesis inhibitor. Shown to inhibit fat accumulation in adipocytes. Antibacterial and antifungal agent. Shown to potentially inhibit the 33.8-kDa Main Protease (Mpro)/3C-like Protease of SARS-CoV-2, consequently inhibiting viral transcription and replication and possibly inhibiting spread of COVID-19. - Chemical. CAS: 517-89-5. Formula: C16H16O5. MW: 288.3. Isolated from Alkanna sp. Anticancer compound. Inhibits TNF-alpha-induced and B-16 melanoma-induced angiogenesis. Induces apoptosis and RIP1- and RIP3-dependent necroptosis in several cancer cells. Circumvents cancer antidrug resistance through the necroptosis pathway. Proteasome inhibitor. Autophagy inducer. Topoisomerase I inhibitor. Inhibits glycolysis in cancer cells by inhibiting tumor-specific pyruvate kinase M2 (PKM2). Anti-inflammatory compound. Inhibits leukocyte migration, downregulates chemokine receptor expression, and inhibits HIV-1 replication. Inhibits the activation of NLRP3 and AIM2 inflammasome. Shown to directly target caspase-1 and as a inhibitor of PKM2 to block PKM2-mediated glycolysis that promotes inflammasome activation by modulating EIF2AK2 phosphorylation in macrophages. Antioxidant. Free radical scavenger. Directly inhibits nitric oxide synthase (NOS). Regulator of systemic glucose tolerance, energy balance and adiposity/obesity. Adipogenesis inhibitor. Shown to inhibit fat accumulation in adipocytes. Antibacterial and antifungal agent.
  • SMILES
    OC1=C2C(C(C=C([C@H](O)C/C=C(C)/C)C2=O)=O)=C(O)C=C1
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    12352200

References

  • Antitumor activity of shikonin and its derivatives: U. Sankawa, et al.; Chem. Pharm. Bull. (Tokyo) 25, 2392 (1977)
  • A comparative study on anti-inflammatory activities of the enantiomers, shikonin and alkannin: S. Tanaka, et al.; J. Nat. Prod. 49, 466 (1986)
  • Shikonin, an ingredient of Lithospermum erythrorhizon, inhibits angiogenesis in vivo and in vitro: T. Hisa, et al.; Anticancer Res. 18, 783 (1998)
  • Shikonin, a component of antiinflammatory Chinese herbal medicine, selectively blocks chemokine binding to CC chemokine receptor-1: X. Chen, et al.; Int. Immunopharmacol. 1, 229 (2001)
  • Shikonin, a component of chinese herbal medicine, inhibits chemokine receptor function and suppresses human immunodeficiency virus type 1: X. Chen, et al.; Antimicrob. Agents Chemother. 47, 2810 (2003)
  • Induction of apoptosis by shikonin through a ROS/JNK-mediated process in Bcr/Abl-positive chronic myelogenous leukemia (CML) cells: X. Mao, et al.; Cell Res. 18, 879 (2008)
  • Dual role of shikonin in early and late stages of collagen type II arthritis: Q. Dai, et al.; Mol. Biol. Rep. 36, 1597 (2009)
  • Shikonin exerts antitumor activity via proteasome inhibition and cell death induction in vitro and in vivo: H. Yang, et al.; Int. J. Cancer 124, 2450 (2009)
  • Shikonin inhibits fat accumulation in 3T3-L1 adipocytes: H. Lee, et al.; Phytother. Res. 24, 344 (2010)
  • Shikonin directly inhibits nitric oxide synthases: possible targets that affect thoracic aorta relaxation response and nitric oxide release from RAW 264.7 macrophages: L.S. Yoshida, et al.; J. Pharmacol. Sci. 112, 343 (2010)