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Chemical Compound Review

AC1NUTIY     (4R,4aR,6R)-4,4a-dimethyl-6- prop-1-en-2-yl...

Synonyms: CPD-4664, CHEBI:23925, LMPR0103270004, C19708, epi-aristolochene, ...
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Disease relevance of epi-aristolochene


High impact information on epi-aristolochene

  • Sequence comparisons with a sesquiterpene cyclase, epi-aristolochene synthase from tobacco, and a diterpene cyclase, casbene synthase from castor bean, demonstrated a significant degree of similarity between these three terpenoid cyclase types, the first three examples of this large family of catalysts to be described from higher plants [2].
  • Finally, the two deduced amino acid sequences were modeled, and the resulting protein models were compared with the crystal structure of tobacco (Nicotiana tabacum) 5-epi-aristolochene synthase, which forms germacrene A as an enzyme-bound intermediate en route to 5-epi-aristolochene [3].
  • The structural basis for this coupled isomerization-cyclization reaction sequence can be inferred by homology modeling of (-)-4S-limonene synthase based on the three-dimensional structure of the sesquiterpene cyclase epi-aristolochene synthase [Starks, C. M., Back, K., Chappell, J., and Noel, J. P. (1997) Science 277, 1815-1820] [4].
  • The utility of this coupled assay was extended by examining the relative efficiency of the EAH enzyme to catalyze hydroxylations of different sesquiterpene skeletons generated by other terpene synthases [5].
  • Capsidiol and deoxycapsidiol biosyntheses were readily measured in coupled assays consisting of 5-epi-aristolochene synthase and EAH as determined by the incorporation of radiolabeled farnesyl diphosphate into thin-layer chromatography-isolated products and verified by gas chromatography-mass spectrometry analysis [5].

Biological context of epi-aristolochene


Anatomical context of epi-aristolochene

  • To define functional and mechanistic features of the EAH enzyme, the utility of a coupled assay using readily available sesquiterpene synthases and microsomes from yeast overexpressing the EAH enzyme was determined [5].

Associations of epi-aristolochene with other chemical compounds


Analytical, diagnostic and therapeutic context of epi-aristolochene


  1. The in vivo synthesis of plant sesquiterpenes by Escherichia coli. Martin, V.J., Yoshikuni, Y., Keasling, J.D. Biotechnol. Bioeng. (2001) [Pubmed]
  2. 4S-limonene synthase from the oil glands of spearmint (Mentha spicata). cDNA isolation, characterization, and bacterial expression of the catalytically active monoterpene cyclase. Colby, S.M., Alonso, W.R., Katahira, E.J., McGarvey, D.J., Croteau, R. J. Biol. Chem. (1993) [Pubmed]
  3. Isolation and characterization of two germacrene A synthase cDNA clones from chicory. Bouwmeester, H.J., Kodde, J., Verstappen, F.W., Altug, I.G., de Kraker, J.W., Wallaart, T.E. Plant Physiol. (2002) [Pubmed]
  4. Truncation of limonene synthase preprotein provides a fully active 'pseudomature' form of this monoterpene cyclase and reveals the function of the amino-terminal arginine pair. Williams, D.C., McGarvey, D.J., Katahira, E.J., Croteau, R. Biochemistry (1998) [Pubmed]
  5. Probing sesquiterpene hydroxylase activities in a coupled assay with terpene synthases. Greenhagen, B.T., Griggs, P., Takahashi, S., Ralston, L., Chappell, J. Arch. Biochem. Biophys. (2003) [Pubmed]
  6. Gene expression of 5-epi-aristolochene synthase and formation of capsidiol in roots of Nicotiana attenuata and N. sylvestris. Bohlmann, J., Stauber, E.J., Krock, B., Oldham, N.J., Gershenzon, J., Baldwin, I.T. Phytochemistry (2002) [Pubmed]
  7. Point mutation of (+)-germacrene A synthase from Ixeris dentata. Chang, Y.J., Jin, J., Nam, H.Y., Kim, S.U. Biotechnol. Lett. (2005) [Pubmed]
  8. Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1,3-dihydroxylase from tobacco (Nicotiana tabacum). Ralston, L., Kwon, S.T., Schoenbeck, M., Ralston, J., Schenk, D.J., Coates, R.M., Chappell, J. Arch. Biochem. Biophys. (2001) [Pubmed]
  9. (+)-(10R)-Germacrene A synthase from goldenrod, Solidago canadensis; cDNA isolation, bacterial expression and functional analysis. Prosser, I., Phillips, A.L., Gittings, S., Lewis, M.J., Hooper, A.M., Pickett, J.A., Beale, M.H. Phytochemistry (2002) [Pubmed]
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