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Chemical Compound Review

aristolochene     (4S,4aR,6S)-4,4a-dimethyl-6- prop-1-en-2-yl...

Synonyms: CHEBI:43445, AC1LCV31, LMPR0103270003, C02004, 123408-96-8, ...
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Disease relevance of aristolochene

  • The aristolochene synthase gene (Ari1) of P. roqueforti has previously been cloned and expressed at low levels as a protein A-aristolochene synthase fusion protein in Escherichia coli [1].

High impact information on aristolochene


Chemical compound and disease context of aristolochene

  • Cloning of the resultant construct into Escherichia coli XL1-Blue and subcloning into the expression host E. coli BL21(DE3)/pLysS gave, after induction with IPTG, soluble aristolochene synthase as 5-10% of total protein [6].

Biological context of aristolochene

  • Aristolochene synthase was encoded by an open reading frame (ORF) of 960 bp, corresponding to a protein of 320 amino acids with a predicted M(D) of 36,480 [6].
  • Using PCR to amplify the aristolochene synthase gene (Aril) from A. terreus genomic DNA revealed the presence of 2 introns, identical in relative location but different in both sequence and length compared to the corresponding Ari1 gene of P. roqueforti [6].
  • A second round of PCR using specific primers was used to prepare a (32)P-labeled 180-bp segment, which was used to screen an A. terreus cDNA library prepared using lambdaZapII, resulting in the identification and sequencing of the A. terreus aristolochene synthase cDNA [6].

Anatomical context of aristolochene

  • We have now used the polymerase chain reaction to amplify the aristolochene synthase coding sequence using engineered primers which produced dsDNA carrying an EcoRI restriction site and the T7 gene 10 ribosome binding site and translational spacer element immediately upstream of the ATG start codon and a BamHI site adjacent to the TAA stop codon [1].

Associations of aristolochene with other chemical compounds

  • The mechanistic details of the cyclisation of farnesylpyrophosphate (FPP) by aristolochene synthase (AS) from Penicillium roqueforti have only recently begun to emerge, mainly through the analysis of the reaction products generated by AS-mutants [7].

Gene context of aristolochene

  • A mutant of Aristolochene Synthase (AS), in which Tyr 92 was replaced by Val, produced the alicyclic beta-(E)-farnesene as the major product, indicating that cyclisation of FPP is controlled by Tyr 92 in AS [8].

Analytical, diagnostic and therapeutic context of aristolochene


  1. Overexpression in Escherichia coli of soluble aristolochene synthase from Penicillium roqueforti. Cane, D.E., Wu, Z., Proctor, R.H., Hohn, T.M. Arch. Biochem. Biophys. (1993) [Pubmed]
  2. Crystal structure determination of aristolochene synthase from the blue cheese mold, Penicillium roqueforti. Caruthers, J.M., Kang, I., Rynkiewicz, M.J., Cane, D.E., Christianson, D.W. J. Biol. Chem. (2000) [Pubmed]
  3. Aristolochene synthase: mechanistic analysis of active site residues by site-directed mutagenesis. Felicetti, B., Cane, D.E. J. Am. Chem. Soc. (2004) [Pubmed]
  4. Germacrene A is a product of the aristolochene synthase-mediated conversion of farnesylpyrophosphate to aristolochene. Calvert, M.J., Ashton, P.R., Allemann, R.K. J. Am. Chem. Soc. (2002) [Pubmed]
  5. Dual role for phenylalanine 178 during catalysis by aristolochene synthase. Forcat, S., Allemann, R.K. Chem. Commun. (Camb.) (2004) [Pubmed]
  6. Aristolochene synthase: purification, molecular cloning, high-level expression in Escherichia coli, and characterization of the Aspergillus terreus cyclase. Cane, D.E., Kang, I. Arch. Biochem. Biophys. (2000) [Pubmed]
  7. Stabilisation of transition states prior to and following eudesmane cation in aristolochene synthase. Forcat, S., Allemann, R.K. Org. Biomol. Chem. (2006) [Pubmed]
  8. Tyrosine 92 of aristolochene synthase directs cyclisation of farnesyl pyrophosphate. Calvert, M.J., Taylor, S.E., Allemann, R.K. Chem. Commun. (Camb.) (2002) [Pubmed]
  9. Aristolochene synthase. Isolation, characterization, and bacterial expression of a sesquiterpenoid biosynthetic gene (Ari1) from Penicillium roqueforti. Proctor, R.H., Hohn, T.M. J. Biol. Chem. (1993) [Pubmed]
  10. Purification and characterization of the sesquiterpene cyclase aristolochene synthase from Penicillium roqueforti. Hohn, T.M., Plattner, R.D. Arch. Biochem. Biophys. (1989) [Pubmed]
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