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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
Chemical Compound Review

Terrein     4,5-dihydroxy-3-[(E)-prop-1- enyl]cyclopent...

Synonyms: AC1NSYFE, SureCN12658627, NSC-291308, NSC291308, 582-46-7, ...
 
 
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High impact information on Terrein

  • The proposed approach also simultaneously verifies the molecular conformation of the two hydroxy groups in terrein established by X-ray data [1].
  • Terrein also reduced the tyrosinase protein level for at least 72 h [2].
  • We then investigated whether terrein influences the extracellular signal-regulated protein kinase (ERK) pathway and the expression of microphthalmia-associated transcription factor (MITF), which is required for tyrosinase expression [2].
  • To elucidate the correlation between ERK pathway activation and a decreased MITF transcriptional level, PD98059, a specific inhibitor of the ERK pathway, was applied before terrein treatment and found to abrogate the terrein-induced MITF attenuation [2].
  • In this study, we found for the first time that terrein has a strong hypopigmentary effect in a spontaneously immortalized mouse melanocyte cell line, Mel-Ab [2].
 

Biological context of Terrein

  • Terrein was found to induce sustained ERK activation and MITF down-regulation, and luciferase assays showed that terrein inhibits MITF promoter activity in a dose-dependent manner [2].
 

Gene context of Terrein

  • These results suggest that terrein reduces melanin synthesis by reducing tyrosinase production via ERK activation, and that this is followed by MITF down-regulation [2].
  • Emericella venezuelensis produces aflatoxin B1, sterigmatocystin, and terrein and compounds with chromophores of the shamixanthone, emerin and desertorin type of compounds [3].

References

  1. Characterization of stereochemistry and molecular conformation using solid-state NMR tensors. Harper, J.K., Mulgrew, A.E., Li, J.Y., Barich, D.H., Strobel, G.A., Grant, D.M. J. Am. Chem. Soc. (2001) [Pubmed]
  2. Terrein: a new melanogenesis inhibitor and its mechanism. Park, S.H., Kim, D.S., Kim, W.G., Ryoo, I.J., Lee, D.H., Huh, C.H., Youn, S.W., Yoo, I.D., Park, K.C. Cell. Mol. Life Sci. (2004) [Pubmed]
  3. Emericella venezuelensis, a new species with stellate ascospores producing sterigmatocystin and aflatoxin B1. Frisvad, J.C., Samson, R.A. Syst. Appl. Microbiol. (2004) [Pubmed]
 
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