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j.phytochem.2012.04.010.pdf | 672.68 kB | Adobe PDF | 見る/開く |
タイトル: | Electrolytic reduction of abscisic acid methyl ester and its free acid. |
著者: | Hirai, Nobuhiro Iwami, Kumiko Horiuchi, Mari Kano, Kenji Todoroki, Yasushi Ohigashi, Hajime |
著者名の別形: | 平井, 伸博 |
キーワード: | Abscisic acid Electrolysis Electrophilicity Cathodic reduction Phaseic acid |
発行日: | Aug-2012 |
出版者: | Elsevier B.V. |
誌名: | Phytochemistry |
巻: | 80 |
開始ページ: | 89 |
終了ページ: | 98 |
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. |
著作権等: | © 2012 Elsevier Ltd. この論文は出版社版でありません。引用の際には出版社版をご確認ご利用ください。 This is not the published version. Please cite only the published version. |
URI: | http://hdl.handle.net/2433/160136 |
DOI(出版社版): | 10.1016/j.phytochem.2012.04.010 |
PubMed ID: | 22621775 |
出現コレクション: | 学術雑誌掲載論文等 |
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