Electrolytic reduction of abscisic acid methyl ester and its free acid.

• 平井, 伸博

• Iwami, Kumiko

• Horiuchi, Mari

• Kano, Kenji

• Todoroki, Yasushi

• Ohigashi, Hajime

抄録

Abscisic acid (ABA, 1), a plant hormone, has electrophilicity derived almost entirely from the side-chain, 3-methylpenta-2, 4-dienoic acid. The electrochemical property of ABA was investigated by analysis of its cathodic reaction. ABA methyl ester (1-Me) was reduced at a peak potential of -1.6 V to give a unique and unstable bicyclic compound (5-Me) as a major product at pH 3 and 7. This finding showed that an electron was absorbed in the conjugated dienecarboxyl group, and that C-5 with a high electron density attacked C-2' through an intramolecular nucleophilic addition. At pH 10, in addition to 5-Me, a compound 4-Me was formed by isomerization of 5-Me under alkaline conditions. For a cathodic reaction of ABA at pH 3 and 7, compound 5 was a major product as well as in the case of ABA methyl ester. However, at pH 10, a dimer (6) with an epoxy group, 1'-deoxy-ABA (7) and other compounds were formed instead of compounds 4 and 5. Compounds 4 and 5 were biologically inactive, suggesting the importance of the electrophilic side-chain of ABA for biological activity.

収録刊行物

• Phytochemistry

  Phytochemistry 80 89-98, 2012-08

  Elsevier B.V.

キーワード

• Abscisic acid
• Electrolysis
• Electrophilicity
• Cathodic reduction
• Phaseic acid

詳細情報

• CRID: 1050001335739775360
• NII論文ID: 120004873777
• NII書誌ID: AA11537190
• ISSN: 00319422
• HANDLE: 2433/160136
• 本文言語コード: en
• 資料種別: journal article
• データソース種別:
  • IRDB
  • CiNii Articles