A pinoresinol-lariciresinol reductase homologue from the creosote bush (Larrea tridentata) catalyzes the efficient in vitro conversion of p-coumaryl/coniferyl alcohol esters into the allylphenols chavicol/eugenol, but not the propenylphenols p-anol/isoeugenol

Arch Biochem Biophys. 2007 Sep 1;465(1):209-18. doi: 10.1016/j.abb.2007.06.002. Epub 2007 Jun 9.


The creosote bush (Larrea tridentata) accumulates a complex mixture of 8-8' regiospecifically linked lignans, of which the potent antioxidant nordihydroguaiaretic acid (NDGA) is the most abundant. Its tetra-O-methyl derivative (M4N) is showing considerable promise in the treatment of refractory (hard-to-treat) brain and central nervous system tumors. NDGA and related 9,9'-deoxygenated lignans are thought to be formed by dimerization of allyl/propenyl phenols, phenylpropanoid compounds that lack C-9 oxygenation, thus differentiating them from the more common monolignol-derived lignans. In our ongoing studies dedicated towards elucidating the biochemical pathway to NDGA and its congeners, a pinoresinol-lariciresinol reductase homologue was isolated from L. tridentata, with the protein obtained in functional recombinant form. This protein efficiently catalyzes the conversion of p-coumaryl and coniferyl alcohol esters into the corresponding allylphenols, chavicol and eugenol; neither of their propenylphenol regioisomers, p-anol and isoeugenol, are formed during this enzyme reaction.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Allylbenzene Derivatives
  • Amino Acid Sequence
  • Anisoles / chemistry*
  • Catalysis
  • Coumaric Acids
  • Enzyme Activation
  • Esters
  • Eugenol / analogs & derivatives
  • Eugenol / chemistry*
  • Isoenzymes / chemistry*
  • Isoenzymes / metabolism
  • Larrea / enzymology*
  • Molecular Sequence Data
  • Oxidoreductases / chemistry*
  • Phenols / chemistry*
  • Propionates / chemistry*


  • Allylbenzene Derivatives
  • Anisoles
  • Coumaric Acids
  • Esters
  • Isoenzymes
  • Phenols
  • Propionates
  • Eugenol
  • isoeugenol
  • estragole
  • coniferyl alcohol
  • Oxidoreductases
  • lariciresinol reductase
  • pinoresinol reductase
  • p-coumaric acid