Chemical Structure
Shikonin [517-89-5]
AG-CN2-0487
Overview
- SupplierAdipoGen Life Sciences
- Product NameShikonin
- Delivery Days Customer10
- CAS Number517-89-5
- CertificationResearch Use Only
- Estimated Purity>98%
- Hazard InformationWarning
- Molecular FormulaC16H16O5
- Molecular Weight288.3
- Scientific DescriptionAnticancer 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.
- SMILESOC1=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
- UNSPSC12352200
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)