S7576

Shikonin

≥98% (HPLC)

• Synonym(s): (±)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone, (±)-Alkannin, (±)-Shikalkin, (±)-Shikonin
• Empirical Formula (Hill Notation): C₁₆H₁₆O₅
• CAS Number: 54952-43-1
• Molecular Weight: 288.30
• NACRES: NA.25
• PubChem Substance ID: 329824586
• UNSPSC Code: 12352200
• MDL number: MFCD00016668

Properties

• Quality Segment: 200
• assay: ≥98% (HPLC)
• form: powder or solid
• color: red to brown
• solubility: methanol: 1 mg/mL
• application(s): metabolomics; vitamins, nutraceuticals, and natural products
• storage temp.: 2-8°C
• SMILES string: C\C(C)=C\CC(O)C1=CC(=O)c2c(O)ccc(O)c2C1=O
• 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
• InChI key: NEZONWMXZKDMKF-UHFFFAOYSA-N

Description

General description

Shikonin is a major phytochemical compound extracted from the roots of Lithospermum erythrorhizon.[1] It is a natural anthraquinone derivative.[2]

Application

Shikonin has been used:

• to enhance the anti-tumor activity of gefitinib on tyrosine kinase receptor epidermal growth factor receptor (EGFR) in wild-type lung cancer cells[3]
• as an inhibitor of renal aerobic glycosis and a potential[4]
• as an anti-inflammatory agent to test its role to improve lipopolysaccharide (LPS)-induced cardiac dysfunction[5]
• to stimulate bone marrow-derived macrophages (BMDMs) to test the effect of Interferon regulatory factor 1 on cell death[6]

Biochem/physiol Actions

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).

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).

Shikonin is a potent anti-fungal agent against C. albicans biofilms.[7] It displays anti-oxidant and chemotherapeutic properties on human glioma cells.[8]

Safety Information

• pictograms: GHS07,GHS09
• signalword: Warning
• hcodes: H302,H400
• pcodes: P273 - P301 + P312 + P330
• Hazard Classifications: Acute Tox. 4 Oral - Aquatic Acute 1
• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable