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Shikonin

AG-CN2-0487-M010 10 mg INQ
AG-CN2-0487-M050 50 mg INQ
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Additional Information

Product Data
Synonyms (+)-Shikonin; (R)-Shikonin; Tokyo Violet; NSC 252844; Isoarnebin 4; C.I. 75535; (R)-5,8-Dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione
Properties
Formula C16H16O5
MW 288.3
CAS 517-89-5
Source/Host Isolated from Alkanna sp.
Purity ≥98% (HPLC)
Appearance Purple red solid.
Solubility Soluble in DMSO or DMF. Sparingly soluble in ethanol, methanol or water.
Identity Determined by 1H-NMR.
InChi Key NEZONWMXZKDMKF-SNVBAGLBSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry. Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
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Product Description

  • Anticancer compound. Inhibits TNF-α-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.

Product References

  1. Antitumor activity of shikonin and its derivatives: U.  Sankawa, et al.; Chem. Pharm. Bull. (Tokyo) 25, 2392 (1977)
  2. A comparative study on anti-inflammatory activities of the enantiomers, shikonin and alkannin: S. Tanaka, et al.; J. Nat. Prod. 49, 466 (1986)
  3. Shikonin, an ingredient of Lithospermum erythrorhizon, inhibits angiogenesis in vivo and in vitro: T. Hisa, et al.; Anticancer Res. 18, 783 (1998)
  4. 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)
  5. 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)
  6. 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)
  7. Dual role of shikonin in early and late stages of collagen type II arthritis: Q. Dai, et al.; Mol. Biol. Rep. 36, 1597 (2009)
  8. 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)
  9. Shikonin inhibits fat accumulation in 3T3-L1 adipocytes: H. Lee, et al.; Phytother. Res. 24, 344 (2010)
  10. 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)
  11. Shikonin inhibits adipogenesis by modulation of the WNT/β-catenin pathway: H. Lee, et al.; Life Sci. 88, 294 (2011)
  12. Shikonin and its analogs inhibit cancer cell glycolysis by targeting tumor pyruvate kinase-M2: J. Chen, et al.; Oncogene 30, 4297 (2011)
  13. Shikonin directly targets mitochondria and causes mitochondrial dysfunction in cancer cells: B. Wiench, et al.; Evid. Based Complement Alternat. Med. 2012, 726025 (2012)
  14. Inhibitory effect of Shikonin on Candida albicans growth: H. Miao, et al.; Biol. Pharm. Bull. 35, 1956 (2012)
  15. Topoisomerase I inhibitors, shikonin and topotecan, inhibit growth and induce apoptosis of glioma cells and glioma stem cells: F.L. Zhang, et al.; PLoS One 8, e81815 (2013)
  16. The anti-tumor effect of shikonin on osteosarcoma by inducing RIP1 and RIP3 dependent necroptosis: Z. Fu, et al.; BMC Cancer 13, 580 (2013)
  17. Evaluation of radical scavenging properties of shikonin: L.S. Yoshida, et al.; J. Clin. Biochem. Nutr. 55, 90 (2014)
  18. Shikonin promotes autophagy in BXPC-3 human pancreatic cancer cells through the PI3K/Akt signaling pathway: S. Shi & H. Cao; Oncol. Lett. 8, 1087 (2014)
  19. The Mechanism Underlying the Antibacterial Activity of Shikonin against Methicillin-Resistant Staphylococcus aureus: Y.S. Lee, et al.; Evid. Based Complement Alternat. Med. 2015, 520578 (2015)
  20. Decreased adiposity and enhanced glucose tolerance in shikonin treated mice: A. Bettaieb, et al.; Obesity 23, 2269 (2015)
  21. Shikonin Suppresses NLRP3 and AIM2 Inflammasomes by Direct Inhibition of Caspase-1: J. Zorman, et al.; PLoS One 11, e0159826 (2016)
  22. PKM2-dependent glycolysis promotes NLRP3 and AIM2 inflammasome activation: M. Xie, et al.; Nat. Commun. 7, 13280 (2016)
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