Stable Isotope-labeling Studies on the Oxidative Coupling of Caffeic Acid via o-Quinone.

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  • TAZAKI Hiroyuki
    Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine
  • TAGUCHI Daisuke
    Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine
  • HAYASHIDA Takaomi
    Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine
  • NABETA Kensuke
    Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine

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The formation of ortho-quinone from ortho-diphenol is a key step in its dimerization. An NMR analysis of the oxidation of 3,4-dihydroxycinnamic acid (caffein acid) by NaIO4 revealed the formation of 3-(3',4'-dioxo-1',5'-cyclohexadienyl) propenoic acid (o-quinone) prior to the formation of furofuran-type lignan 4,8-exo-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione. Both electrolytic and enzymatic oxidation of caffeic acid also generated o-quinone. The yields of o-quinone from caffeic acid were quantified by NMR and HPLC analyses. A stable isotope-labeling study of the formation of lignans directly proved the random radical coupling of semiquinone radicals formed from a set of caffeic acid and o-quinone.

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