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.
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.
Vassão
Daniel G
DG
Institute of Biological Chemistry, Washington State University, 467 Clark Hall, Pullman, WA 99164-6340, USA.
Kim
Sung-Jin
SJ
Milhollan
Jessica K
JK
Eichinger
Dietmar
D
Davin
Laurence B
LB
Lewis
Norman G
NG
D000081248:Allylbenzene Derivatives; D000595:Amino Acid Sequence; D000840:Anisoles / Q000737:chemistry*; D002384:Catalysis; D003373:Coumaric Acids; D004789:Enzyme Activation; D004952:Esters; D005054:Eugenol / Q000031:analogs & derivatives / Q000737:chemistry*; D007527:Isoenzymes / Q000737:chemistry* / Q000378:metabolism; D032442:Larrea / Q000201:enzymology*; D008969:Molecular Sequence Data; D010088:Oxidoreductases / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry*; D011422:Propionates / Q000737:chemistry*
D000081248:Allylbenzene Derivatives; D000840:Anisoles; D003373:Coumaric Acids; D004952:Esters; D007527:Isoenzymes; D010636:Phenols; D011422:Propionates; D005054:Eugenol; C036643:isoeugenol; C007633:estragole; C010559:coniferyl alcohol; D010088:Oxidoreductases; C084968:lariciresinol reductase; C084969:pinoresinol reductase; C495469:p-coumaric acid