Stable Isotope-labeling Studies on the Oxidative Coupling of Caffeic Acid via o-Quinone(Organic Chemistry)

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概要

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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 (caffeic acid) by NaIO_4 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.

• 社団法人日本農芸化学会の論文
• 2001-12-23

著者

• Tazaki Hiroyuki

  Department of Veterinary and Animal Science ,Nippon Veterinary and Life Science University

• Tazaki Hiroyuki

  Applied Plant Research Laboratory Yokohama Center Japan Tobacco Inc.

• 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

• Nabeta Kensuke

  Department Of Agricultural Chemistry Obihiro University Of Agriculture And Veterinary Medicine

• Taguchi Daisuke

  Department Of Bioresource Science Obihiro University Of Agriculture And Veterinary Medicine

• Tazaki Hiroyuki

  Department Of Bioresource Chemistry Obihiro University Of Agriculture And Veterinary Medicine

• Hayashida Takaomi

  Department Of Bioresource Science Obihiro University Of Agriculture And Veterinary Medicine

• Nabeta K

  Obihiro Univ. Agriculture And Veterinary Medicine Obihiro Jpn

• Tazaki H

  Department Of Veterinary Science Nippon Veterinary And Life Science University

• TAZAKI Hiroyuki

  Department of Agricultural Chemistry, Faculty of Agriculture, Hokkaido University

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