2022年3月3日
Occurrence of Z-2-oxo-4-methyl-3-pentene-1,5-dioic acid and its regioisomer 4-methylene-2-oxo-glutaric acid in tulip tissues
Zeitschrift für Naturforschung C
- ,
- 巻
- 77
- 号
- 7-8
- 開始ページ
- 317
- 終了ページ
- 330
- 記述言語
- 掲載種別
- 研究論文(学術雑誌)
- DOI
- 10.1515/znc-2021-0282
- 出版者・発行元
- Walter de Gruyter GmbH
Abstract
Although Z-2-oxo-4-methyl-3-pentene-1,5-dioic acid (Z-OMPD) has been identified as a major dicarboxylic acid in tulip tissues, its biosynthetic pathway has not been elucidated. Herein, Z-OMPD was isolated from tulip leaves and chemically synthesized. Comparisons of these samples revealed that Z-OMPD exists as a tautomeric mixture at physiological pH. As a regioisomer of Z-OMPD, we enzymatically and chemically prepared 4-methylene-2-oxo-glutaric acid (4-MEOG) for the first time. Using these compounds as standards, the occurrence of Z-OMPD and 4-MEOG in various tissues of the tulip cultivar “Murasakizuisho” was evaluated directly and by 2,4-dinitrophenylhydrazone derivatization. Z-OMPD was found to be abundant in the aerial tissues, whereas 4-MEOG was almost absent from all tissues. Stability analyses of Z-OMPD and 4-MEOG revealed that no double bond isomerization occurred at physiological pH, suggesting that enzyme systems are responsible for Z-OMPD biosynthesis in tulip tissues.
Although Z-2-oxo-4-methyl-3-pentene-1,5-dioic acid (Z-OMPD) has been identified as a major dicarboxylic acid in tulip tissues, its biosynthetic pathway has not been elucidated. Herein, Z-OMPD was isolated from tulip leaves and chemically synthesized. Comparisons of these samples revealed that Z-OMPD exists as a tautomeric mixture at physiological pH. As a regioisomer of Z-OMPD, we enzymatically and chemically prepared 4-methylene-2-oxo-glutaric acid (4-MEOG) for the first time. Using these compounds as standards, the occurrence of Z-OMPD and 4-MEOG in various tissues of the tulip cultivar “Murasakizuisho” was evaluated directly and by 2,4-dinitrophenylhydrazone derivatization. Z-OMPD was found to be abundant in the aerial tissues, whereas 4-MEOG was almost absent from all tissues. Stability analyses of Z-OMPD and 4-MEOG revealed that no double bond isomerization occurred at physiological pH, suggesting that enzyme systems are responsible for Z-OMPD biosynthesis in tulip tissues.
- リンク情報
- ID情報
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- DOI : 10.1515/znc-2021-0282
- ISSN : 0939-5075
- eISSN : 1865-7125