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(-)-Alkannin

Catalog No. T4958 CAS 517-88-4

Synonyms: Alkannin, Shikonin

(-)-Alkannin (Shikonin) is a natural red naphthoquinone pigment, has antimicrobial, anti-tumor, and anti-inflammatory effects; a purified shikonin preparation is widely used for the production of medicinals, cosmetics, and some food products; shikonin also enters into the antiinflammatory ointment and cream compositions used for the treatment of burns. It can suppress the cell viability, adhesion, invasion and migratory ability of MGC-803 cells through TLR2- or NF-κB-mediated pathway.

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(-)-Alkannin, CAS 517-88-4

Pack Size	Availability	Price/USD	Quantity
20 mg	In stock	$ 60.00
1 mL * 10 mM (in DMSO)	In stock	$ 50.00

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Purity: 99.81%

Purity: 98.28%

Biological Description

Chemical Properties

Storage & Solubility Information

Description	(-)-Alkannin (Shikonin) is a natural red naphthoquinone pigment, has antimicrobial, anti-tumor, and anti-inflammatory effects; a purified shikonin preparation is widely used for the production of medicinals, cosmetics, and some food products; shikonin also enters into the antiinflammatory ointment and cream compositions used for the treatment of burns. It can suppress the cell viability, adhesion, invasion and migratory ability of MGC-803 cells through TLR2- or NF-κB-mediated pathway.
In vitro	3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay was performed for cell viability and adhesion ability of MGC-803 cells. Cell scratch repair experiments were conducted for the determination of migration ability while transwell assay for cell invasion ability. Western blot analysis and real-time polymerase chain reaction assay were used for the detection of protein and mRNA expressions. Fifty per cent inhibitory concentration of Shikonin on MGC-803 cells was 1.854?μm. Shikonin (1?μm) inhibited significantly the adhesion, invasion and migratory ability of MGC-803 cells. Interestingly, Shikonin in the presence or absence of anti-Toll-like receptor 2 (TLR2) antibody (2?μg) and nuclear factor-kappa B (NF-κB) inhibitor MG-132 (10?μm) could decrease these ability of MGC-803 cells markedly, as well as the expression levels of matrix metalloproteinases (MMP)-2, MMP-7, TLR2 and p65 NF-κB. In addition, the co-incubation of Shikonin and anti-TLR2/MG-132 has a significant stronger activity than anti-TLR2 or MG-132 alone.
Kinase Assay	Histamine release from basophils stimulated with anti-IgE antibody was analyzed fluorimetrically. Syk and Lyn kinase activities were tested in Vitro with recombinant proteins and analyzed by off-chip mobility shift assay. Shikonin dose-dependently inhibited the histamine release from basophils induced by anti-IgE antibody (IC50 = 2.6 +/- 1.0 microM; mean +/- SEM). A search for the target(s) of Shikonin in the signal cascade of IgE-mediated activation showed that it strongly inhibits Syk (IC50 = 7.8 microM, in the recombinant kinase assay), which plays a pivotal role in the degranulation response. A less significant inhibition was found for Lyn, which phosphorylates FcepsilonRI-betagamma subunits and also Syk.
Source	Natural Products > Boraginaceae > Lithospermum

Synonyms	Alkannin, Shikonin
Molecular Weight	288.3
Formula	C16H16O5
CAS No.	517-88-4

Storage

keep away from direct sunlight

Powder: -20°C for 3 years | In solvent: -80°C for 1 year

Solubility Information

DMSO: 50 mg/mL (173.43 mM)

References and Literature

1. Takano-Ohmuro H , Yoshida L S , Yuda Y , et al. Shikonin inhibits IgE-mediated histamine release by human basophils and Syk kinase activity[J]. Inflammation Research, 2008, 57(10):484-488. 2. Liu J P , Liu D , Gu J F , et al. Shikonin inhibits the cell viability, adhesion, invasion and migration of the human gastric cancer cell line MGC‐803 via the Toll‐like receptor 2/nuclear factor‐kappa B pathway[J]. Journal of Pharmacy & Pharmacology, 2015, 67(8):1143-1155. 3. Gara R K , Srivastava V K , Duggal S , et al. Shikonin selectively induces apoptosis in human prostate cancer cells through the endoplasmic reticulum stress and mitochondrial apoptotic pathway[J]. Journal of Biomedical Science, 2015, 22(1):26. 4. Qu D , Xu X , Zhang M , et al. Cbl participates in shikonin-induced apoptosis by negatively regulating phosphoinositide 3-kinase/protein kinase B signaling. Molecular Medicine Reports, 2015. 6. Xue W, et al. Alkannin Inhibited Hepatic Inflammation in Diabetic Db/Db Mice. Cell Physiol Biochem. 2018;45(6):2461-2470. 7. Xu J, Wang Q, Leung E L H, et al. Compound C620-0696, a new potent inhibitor targeting BPTF, the chromatin-remodeling factor in non-small-cell lung cancer[J]. Frontiers of Medicine. 2020, 14(1): 60-67.

Citations

1. Zhang Z Z, Wen C H, Jia M, et al. Alkannin exerts antitumor properties in cutaneous squamous cell carcinoma by inducing apoptosis and shifting the M1/M2 polarization of tumor‐associated macrophages by upregulating PTEN. The Kaohsiung Journal of Medical Sciences. 2022 2. Xu J, Wang Q, Leung E L H, et al. Compound C620-0696, a new potent inhibitor targeting BPTF, the chromatin-remodeling factor in non-small-cell lung cancer. Frontiers of Medicine. 2020, 14(1): 60-67.

Related compound libraries

This product is contained In the following compound libraries：

Anti-Cancer Active Compound Library Anti-Tumor Natural Product Library Anti-Fibrosis Compound Library Stem Cell Differentiation Compound Library Anti-Cancer Compound Library Anti-Ovarian Cancer Compound Library Anti-Liver Cancer Compound Library Oxidation-Reduction Compound Library Anti-Pancreatic Cancer Compound Library Antidepressant Compound Library

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Keywords

(-)-Alkannin 517-88-4 Apoptosis PI3K/Akt/mTOR signaling PI3K Inhibitor ()Alkannin Alkannin inhibit Shikonin ( ) Alkannin inhibitor

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