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:
Product Name
Shikonin, ≥98% (HPLC)
InChI key
NEZONWMXZKDMKF-UHFFFAOYSA-N
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
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
Quality Level
Related Categories
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.
General description
Shikonin is a major phytochemical compound extracted from the roots of Lithospermum erythrorhizon. It is a natural anthraquinone derivative.
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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Ke Gong et al.
Free radical biology & medicine, 51(12), 2259-2271 (2011-10-21)
Although shikonin, a naphthoquinone derivative, has showed anti-cancer activity, its precise molecular anti-tumor mechanism remains to be elucidated. In this study, we investigated the effects of shikonin on human hepatocellular carcinoma (HCC) in vitro and in vivo. Our results showed
Konstantinos N Kontogiannopoulos et al.
International journal of pharmaceutics, 422(1-2), 381-389 (2011-10-08)
The interest of drug delivery has focused on the creation of new formulations with improved properties, taking much attention to the drug release from the carrier. Liposomes have already been commercialized, while dendrimers and hyperbranched polymers are emerging as potentially
Yongwei Wang et al.
Biochemical pharmacology, 88(3), 322-333 (2014-02-14)
Although gemcitabine is currently the best chemotherapeutic agent available for the treatment of advanced pancreatic cancer, eventual failure of response is a significant clinical problem. Therefore, novel therapeutic approaches against this disease are highly needed. The aim of this study
Jen-Tsung Yang et al.
PloS one, 9(4), e94180-e94180 (2014-04-10)
Shikonin is a quinone-containing natural product that induces the apoptotic death of some cancer cell lines in culture through increasing intracellular reactive oxygen species (ROS). Quinone-based drugs have shown potential in the clinic, making shikonin an interesting compound to study.
Hui-Ming Chen et al.
Cancer immunology, immunotherapy : CII, 61(11), 1989-2002 (2012-04-25)
Immunogenic cell death is characterized by damage-associated molecular patterns, which can enhance the maturation and antigen uptake of dendritic cells. Shikonin, an anti-inflammatory and antitumor phytochemical, was exploited here as an adjuvant for dendritic cell-based cancer vaccines via induction of
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