Ionylideneacetic Acids and Abscisic Acid Biosynthesis by Cercospora rosicola

スポンサーリンク

概要

• 論文の詳細を見る

• Several compounds having the basic α-ionylideneacetic acid structure were tested in Cercospora rosicola resuspensions. At 100μM, all the compounds inhibited abscisic acid (ABA) biosynthesis. Time studies with unlabelled and deuterated (2Z, 4E)- and (2E, 4E)-α-ionylideneacetic acids showed rapid conversions into both (2Z, 4E)- and (2E, 4E)-4-keto-α-ionylideneacetic acids as major products. Incorporation of the label into ABA was specific for the 2Z, 4E-isomer. Minor products, identified by GC-MS, were (2Z, 4E)- and (2E, 4E)-4-hydroxy-α-ionylideneacetic acids and (2Z, 4E)-1-hydroxy-α-ionylideneacetic acid. The conversion to (2Z, 4E)-1-hydroxy-α-xionylideneacetic acid has not been previously reported and was specific for the 2Z, 4E-isomer. A time study for the conversion of methyl esters of [2H3]-(2Z, 4E)- and [2H3]-(2E, 4E)-4-keto-α-ionylideneacetates showed a slow introduction of the 1-hydroxyl group and specificity for 2Z, 4E-isomer. Conversion of the ethyl esters of (2Z, 4E)- and (ZE, 4E)-1-hydroxy-α-ionylideneacetates into the ethyl esters of both ABA and (2E, 4E)-ABA demonstrated that ABA can be formed by oxidation of the 4-position after the insertion of the 1-hydroxy group. The ethyl 1-hydroxy acids were also isomerized to the corresponding ethyl (2Z, 4E)- and ethyl (2E, 4E)-3-hydroxy-β-ionylideneacetates. Ethyl (2Z, 4E)-1-hydroxy acid also gave small amounts of ethyl 1, 4-trans-diol of ABA. These results suggest that ABA may be formed through a (2Z, 4E)-1-hydroxy-α-ionylidene-type intermediate in addition to the previously proposed route through (2Z, 4E)-4-ketoa-α-ionylideneacetic acid.

• 社団法人 日本農芸化学会の論文

著者

• NELSON Mary

  USD A, ARS, Fruit and Vegetable Chemistry Laboratory

• NORMAN Shirley

  USD A, ARS, Fruit and Vegetable Chemistry Laboratory

• POLING Stephen

  USD A, ARS, Fruit and Vegetable Chemistry Laboratory

• MAIER V.

  USD A, ARS, Fruit and Vegetable Chemistry Laboratory

関連論文

• Farnesyl and α-Ionylideneethyl Tertiary and Quaternary Amines: Their Influence on Abscisic Acid Biosynthesis by Cercospora rosicola
• Ionylideneacetic Acids and Abscisic Acid Biosynthesis by Cercospora rosicola

スポンサーリンク