(+-)-Shikonin

• CAT Number: I036298
• CAS Number: 54952-43-1
• Molecular Formula: C16H16O5
• Molecular Weight: 288.3
• Purity: 98%
• Synonyms: (+-)-Alkannin, (+-)-Shikonin, Arnebin-4, Shikonin
• Target: Disease Research Fields
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)- (9CI)
• 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
• InChIKey: NEZONWMXZKDMKF-UHFFFAOYSA-N
• SMILES: CC(=CCC(C1=CC(=O)c2c(ccc(c2C1=O)O)O)O)C

(+/-)-Shikonin (Cat.No:I036298) is a natural compound derived from the root of Lithospermum erythrorhizon. It possesses various pharmacological activities, including anti-inflammatory, antioxidant, and anticancer properties. (+/-)-Shikonin has shown potential in preclinical studies for its ability to inhibit tumor growth and modulate immune responses, making it a promising candidate for further research in cancer therapeutics.

Reference

1: Qiu HY, Fu JY, Yang MK, Han HW, Wang PF, Zhang YH, Lin HY, Tang CY, Qi JL, Yang RW, Wang XM, Zhu HL, Yang YH. Identification of new shikonin derivatives as STAT3 inhibitors. Biochem Pharmacol. 2017 Dec 15;146:74-86. doi: 10.1016/j.bcp.2017.10.009. Epub 2017 Oct 21. PubMed PMID: 29066190.
2: Zhai T, Hei Z, Ma Q, Liang H, Xu Y, Zhang Y, Jin L, Han C, Wang J. Shikonin induces apoptosis and G0/G1 phase arrest of gallbladder cancer cells via the JNK signaling pathway. Oncol Rep. 2017 Dec;38(6):3473-3480. doi: 10.3892/or.2017.6038. Epub 2017 Oct 17. PubMed PMID: 29039581.
3: Lu B, Gong X, Wang ZQ, Ding Y, Wang C, Luo TF, Piao MH, Meng FK, Chi GF, Luo YN, Ge PF. Shikonin induces glioma cell necroptosis in vitro by ROS overproduction and promoting RIP1/RIP3 necrosome formation. Acta Pharmacol Sin. 2017 Nov;38(11):1543-1553. doi: 10.1038/aps.2017.112. Epub 2017 Aug 17. PubMed PMID: 28816233; PubMed Central PMCID: PMC5672068.
4: Yang J, Wang Z, Chen DL. Shikonin ameliorates isoproterenol (ISO)-induced myocardial damage through suppressing fibrosis, inflammation, apoptosis and ER stress. Biomed Pharmacother. 2017 Sep;93:1343-1357. doi: 10.1016/j.biopha.2017.06.086. Epub 2017 Jul 24. PubMed PMID: 28753907.
5: Zhou G, Yang Z, Wang X, Tao R, Zhou Y. TRAIL Enhances Shikonin Induced Apoptosis through ROS/JNK Signaling in Cholangiocarcinoma Cells. Cell Physiol Biochem. 2017;42(3):1073-1086. doi: 10.1159/000478758. Epub 2017 Jun 29. PubMed PMID: 28662515.
6: Kim HJ, Hwang KE, Park DS, Oh SH, Jun HY, Yoon KH, Jeong ET, Kim HR, Kim YS. Shikonin-induced necroptosis is enhanced by the inhibition of autophagy in non-small cell lung cancer cells. J Transl Med. 2017 May 31;15(1):123. doi: 10.1186/s12967-017-1223-7. PubMed PMID: 28569199; PubMed Central PMCID: PMC5452303.
7: Wang TY, Zhou QL, Li M, Shang YX. Shikonin alleviates allergic airway remodeling by inhibiting the ERK-NF-κB signaling pathway. Int Immunopharmacol. 2017 Jul;48:169-179. doi: 10.1016/j.intimp.2017.05.011. Epub 2017 May 15. PubMed PMID: 28521243.
8: Li X, Fan XX, Jiang ZB, Loo WT, Yao XJ, Leung EL, Chow LW, Liu L. Shikonin inhibits gefitinib-resistant non-small cell lung cancer by inhibiting TrxR and activating the EGFR proteasomal degradation pathway. Pharmacol Res. 2017 Jan;115:45-55. doi: 10.1016/j.phrs.2016.11.011. Epub 2016 Nov 15. PubMed PMID: 27864022.
9: Jeung YJ, Kim HG, Ahn J, Lee HJ, Lee SB, Won M, Jung CR, Im JY, Kim BK, Park SK, Son MJ, Chung KS. Shikonin induces apoptosis of lung cancer cells via activation of FOXO3a/EGR1/SIRT1 signaling antagonized by p300. Biochim Biophys Acta. 2016 Nov;1863(11):2584-2593. doi: 10.1016/j.bbamcr.2016.07.005. Epub 2016 Jul 21. PubMed PMID: 27452907.