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Chemical Compound Review

Alkannin     5,8-dihydroxy-2-(1-hydroxy-4- methyl-pent-3...

Synonyms: Anchusin, shikonin, SHIKALKIN, ARNEBIN-4, ALKANNIN, 1-, ...
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Disease relevance of NSC94524

  • Bioassay-directed fractionation of extract of Arnebia euchroma led to the isolation of alkannin (1), shikonin (2), and their derivatives (3-8) as the active principles against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE) [1].
  • Shikonin and alkannin produced a dose-dependent acceleration of the cotton pellet-induced granuloma formation and this accelerating potency of both compounds on the proliferation of granulation tissue was about the same 5 and 10 d after implantation of the cotton pellet [2].

High impact information on NSC94524

  • Alkannin, shikonin (A/S) and their derivatives are enantiomeric hydroxynaphthoquinone red pigments found in the roots of almost 150 species of the Boraginaceae family [3].
  • In order to better understand the molecular aspects of the cytotoxic action mechanisms, the cytotoxicity of alkannin derivatives, 1-10, on five human tumor cell lines were examined and their standard redox potentials in aprotic medium were tested by means of cyclic voltammetry [4].
  • Oligomeric alkannin and shikonin are formed during biosynthesis of these bioactive secondary metabolites in Boraginaceaous root plants, during tissue culture production of A/S, during alkaline hydrolysis of A/S esters and also thermal treatment of A/S [5].
  • Antitumor activity of shikonin, alkannin and their derivatives. II. X-ray analysis of cyclo-alkannin leucoacetate, tautomerism of alkannin and cyclo-alkannin and antitumor activity of alkannin derivatives [6].
  • Sodium dodecyl sulfate resulted in microcapsules with desirable morphological and physicochemical characteristics, while acacia and tragacanth gums were not indicated as surfactants in alkannin microencapsulation since they gave a high release rate and a great extent of particle size, respectively [7].

Anatomical context of NSC94524

  • The present study was carried out to compare the accelerating effect of shikonin and alkannin and to elucidate the expression of CD antigen and histological changes on the proliferation of granulation tissue in rats [2].

Analytical, diagnostic and therapeutic context of NSC94524


  1. 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]
  2. Study of the accelerating effect of shikonin and alkannin on the proliferation of granulation tissue in rats. Ozaki, Y., Sakaguchi, I., Tujimura, M., Ikeda, N., Nakayama, M., Kato, Y., Suzuki, H., Satake, M. Biol. Pharm. Bull. (1998) [Pubmed]
  3. Analysis of alkannin derivatives from Alkanna species by high-performance liquid chromatography/photodiode array/mass spectrometry. Assimopoulou, A.N., Karapanagiotis, I., Vasiliou, A., Kokkini, S., Papageorgiou, V.P. Biomed. Chromatogr. (2006) [Pubmed]
  4. The molecular mechanisms involved in the cytotoxicity of alkannin derivatives. Wu, H.Q., Huang, Z.S., Bu, X.Z., Shen, Y.D., Zhang, Z.L., Xie, B.F., Liu, Z.C., Gu, L.Q., Chan, A.S. European journal of medicinal chemistry. (2005) [Pubmed]
  5. Structure determination of oligomeric alkannin and shikonin derivatives. Spyros, A., Assimopoulou, A.N., Papageorgiou, V.P. Biomed. Chromatogr. (2005) [Pubmed]
  6. Antitumor activity of shikonin, alkannin and their derivatives. II. X-ray analysis of cyclo-alkannin leucoacetate, tautomerism of alkannin and cyclo-alkannin and antitumor activity of alkannin derivatives. Sankawa, U., Otsuka, H., Kataoka, Y., Iitaka, Y., Hoshi, A., Kuretani, K. Chem. Pharm. Bull. (1981) [Pubmed]
  7. Preparation and release studies of alkannin-containing microcapsules. Assimopoulou, A.N., Papageorgiou, V.P. Journal of microencapsulation. (2004) [Pubmed]
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