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Chemical Compound Review

shikonin     5,8-dihydroxy-2-[(1R)-1- hydroxy-4-methyl...

Synonyms: Shikonine, Isoarnebin 4, CHEMBL9470, SureCN33969, CCRIS 6492, ...
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Disease relevance of shikonin


High impact information on shikonin

  • We demonstrated that shikonin-inhibitory response was retained in the core TNF-alpha promoter region containing the TATA box and a 48-bp downstream sequence relative to the transcription start site [5].
  • Further our results indicated that shikonin suppressed the basal transcription and activator-regulated transcription of TNF-alpha by inhibiting the binding of transcription factor IID protein complex (TATA box-binding protein) to TATA box [5].
  • Shikonin inhibited the phosphatidylinositol 3,4,5-triphosphate (PtdIns-3,4,5-P3) phosphatase activity of recombinant phosphatase and tensin homolog deleted on chromosome 10 (PTEN) with an IC50 value of 2.7 microM [6].
  • A naphthoquinone derivative, shikonin, has insulin-like actions by inhibiting both phosphatase and tensin homolog deleted on chromosome 10 and tyrosine phosphatases [6].
  • Its effect on tyrosine phosphorylation in intact cells was far weaker than that of pervanadate, a widely used tyrosine phosphatase inhibitor, despite the observation that the effect of shikonin on PKB was more potent than that of pervanadate [6].

Biological context of shikonin


Anatomical context of shikonin


Associations of shikonin with other chemical compounds


Gene context of shikonin


Analytical, diagnostic and therapeutic context of shikonin


  1. Shikonin, a component of chinese herbal medicine, inhibits chemokine receptor function and suppresses human immunodeficiency virus type 1. Chen, X., Yang, L., Zhang, N., Turpin, J.A., Buckheit, R.W., Osterling, C., Oppenheim, J.J., Howard, O.M. Antimicrob. Agents Chemother. (2003) [Pubmed]
  2. Involvement of reactive oxygen species, but not mitochondrial permeability transition in the apoptotic induction of human SK-Hep-1 hepatoma cells by shikonin. Chen, C.H., Chern, C.L., Lin, C.C., Lu, F.J., Shih, M.K., Hsieh, P.Y., Liu, T.Z. Planta Med. (2003) [Pubmed]
  3. Beta-hydroxyisovalerylshikonin is a novel and potent inhibitor of protein tyrosine kinases. Hashimoto, S., Xu, Y., Masuda, Y., Aiuchi, T., Nakajo, S., Uehara, Y., Shibuya, M., Yamori, T., Nakaya, K. Jpn. J. Cancer Res. (2002) [Pubmed]
  4. Shikonin modulates cell proliferation by inhibiting epidermal growth factor receptor signaling in human epidermoid carcinoma cells. Singh, F., Gao, D., Lebwohl, M.G., Wei, H. Cancer Lett. (2003) [Pubmed]
  5. Shikonins, phytocompounds from Lithospermum erythrorhizon, inhibit the transcriptional activation of human tumor necrosis factor alpha promoter in vivo. Staniforth, V., Wang, S.Y., Shyur, L.F., Yang, N.S. J. Biol. Chem. (2004) [Pubmed]
  6. A naphthoquinone derivative, shikonin, has insulin-like actions by inhibiting both phosphatase and tensin homolog deleted on chromosome 10 and tyrosine phosphatases. Nigorikawa, K., Yoshikawa, K., Sasaki, T., Iida, E., Tsukamoto, M., Murakami, H., Maehama, T., Hazeki, K., Hazeki, O. Mol. Pharmacol. (2006) [Pubmed]
  7. Acylshikonin analogues: synthesis and inhibition of DNA topoisomerase-I. Ahn, B.Z., Baik, K.U., Kweon, G.R., Lim, K., Hwang, B.D. J. Med. Chem. (1995) [Pubmed]
  8. Regulatory role of microsomal 3-hydroxy-3-methylglutaryl-coenzyme A reductase for shikonin biosynthesis in Lithospermum erythrorhizon cell suspension cultures. Lange, B.M., Severin, K., Bechthold, A., Heide, L. Planta (1998) [Pubmed]
  9. Molecular cloning and characterization of a cDNA encoding a novel apoplastic protein preferentially expressed in a shikonin-producing callus strain of Lithospermum erythrorhizon. Yamamura, Y., Sahin, F.P., Nagatsu, A., Mizukami, H. Plant Cell Physiol. (2003) [Pubmed]
  10. Impairment of vascular function of rat thoracic aorta in an endothelium-dependent manner by shikonin/alkannin and derivatives isolated from roots of Macrotomia euchroma. Hu, C.M., Cheng, Y.W., Cheng, H.W., Kang, J.J. Planta Med. (2004) [Pubmed]
  11. A novel dark-inducible protein, LeDI-2, and its involvement in root-specific secondary metabolism in Lithospermum erythrorhizon. Yazaki, K., Matsuoka, H., Shimomura, K., Bechthold, A., Sato, F. Plant Physiol. (2001) [Pubmed]
  12. Geranylhydroquinone 3"-hydroxylase, a cytochrome P-450 monooxygenase from Lithospermum erythrorhizon cell suspension cultures. Yamamoto, H., Inoue, K., Li, S.M., Heide, L. Planta (2000) [Pubmed]
  13. Inhibition of platelet aggregation by shikonin derivatives isolated from Arnebia euchroma. Chang, Y.S., Kuo, S.C., Weng, S.H., Jan, S.C., Ko, F.N., Teng, C.M. Planta Med. (1993) [Pubmed]
  14. New naphthoquinones from Arnebia hispidissima roots. Shukla, Y.N., Srivastava, A., Singh, S.C., Kumar, S. Planta Med. (2001) [Pubmed]
  15. Phosphorylated extracellular signal-regulated kinase up-regulated p53 expression in shikonin-induced HeLa cell apoptosis. Wu, Z., Wu, L.J., Tashiro, S., Onodera, S., Ikejima, T. Chin. Med. J. (2005) [Pubmed]
  16. Shikonin, a component of antiinflammatory Chinese herbal medicine, selectively blocks chemokine binding to CC chemokine receptor-1. Chen, X., Oppenheim, J., Howard, O.M. Int. Immunopharmacol. (2001) [Pubmed]
  17. Human ACAT inhibitory effects of shikonin derivatives from Lithospermum erythrorhizon. An, S., Park, Y.D., Paik, Y.K., Jeong, T.S., Lee, W.S. Bioorg. Med. Chem. Lett. (2007) [Pubmed]
  18. 4-Hydroxybenzoate 3-geranyltransferase from Lithospermum erythrorhizon: purification of a plant membrane-bound prenyltransferase. Mühlenweg, A., Melzer, M., Li, S.M., Heide, L. Planta (1998) [Pubmed]
  19. Genetic engineering of shikonin biosynthesis hairy root cultures of Lithospermum erythrorhizon transformed with the bacterial ubiC gene. Sommer, S., Köhle, A., Yazaki, K., Shimomura, K., Bechthold, A., Heide, L. Plant Mol. Biol. (1999) [Pubmed]
  20. Shikonin, an ingredient of Lithospermum erythrorhizon induced apoptosis in HL60 human premyelocytic leukemia cell line. Yoon, Y., Kim, Y.O., Lim, N.Y., Jeon, W.K., Sung, H.J. Planta Med. (1999) [Pubmed]
  21. Antimicrobial activities of naphthazarins from Arnebia euchroma. Shen, C.C., Syu, W.J., Li, S.Y., Lin, C.H., Lee, G.H., Sun, C.M. J. Nat. Prod. (2002) [Pubmed]
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