S7576
Shikonin
≥98% (HPLC)
Synonym(s):
(±)-5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone, (±)-Alkannin, (±)-Shikalkin, (±)-Shikonin
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About This Item
Empirical Formula (Hill Notation):
C16H16O5
CAS Number:
Molecular Weight:
288.30
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Quality Segment
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
General description
Shikonin is a major phytochemical compound extracted from the roots of Lithospermum erythrorhizon. It is a natural anthraquinone derivative.
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
- as an inhibitor of renal aerobic glycosis and a potential
- as an anti-inflammatory agent to test its role to improve lipopolysaccharide (LPS)-induced cardiac dysfunction
- to stimulate bone marrow-derived macrophages (BMDMs) to test the effect of Interferon regulatory factor 1 on cell death
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. It displays anti-oxidant and chemotherapeutic properties on human glioma cells.
signalword
Warning
hcodes
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
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