12-oxo phytodienoic acid

12-Oxo phytodienoic acid (12-oxo PDA) 是具有生物活性的 7-epi jasmonic acid 的直接前体。12-Oxo phytodienoic acid 在介导对病原体和害虫的抗性中起非依赖性作用。

13-epi-12-oxo Phytodienoic acid (13-epi-12-oxo PDA) is a lipoxygenase metabolite of α-linolenic acid in the leaves of green plants such as corn. ω-3 and ω-6 polyunsaturated fatty acids in plants are substrates for plant lipoxygenases. 12-oxo PDA is one of the best studied end metabolites of this enzymatic pathway. While the initial enzymatic product and major isomer of 12-oxo PDA contains side chains in the cis position, both being β to the ring, the upper side chain attached at C-13, can and frequently does, isomerize when 12-oxo PDA is extracted, isolated, or stored. 13-epi-12-oxo PDA is the product of this isomerization.

1dinor-12-oxo-Phytodienoic acid (dinor-OPDA) serves as an intermediate in the biosynthesis of jasmonic acid from hexadecatrienoic acid, playing a crucial role in the jasmonate pathway in plants. This pathway oxygenates and modifies certain unsaturated fatty acids to produce plant hormones critical for processes such as senescence, flower development, mechanotransduction, and response to herbivory. Additionally, dinor-OPDA can be incorporated into glycerolipids and galactolipids, including specific arabidopsides.

(±)-7-epiJasmonic acid, the primary metabolite in the 12-oxo phytodienoic acid pathway of 13(S)-hydroperoxy linolenic acid metabolism in plants, is synthesized initially as the more active (+)-7-epijasmonic acid. It quickly epimerizes to the more stable (−)-7-jasmonic acid isomer, demonstrating its biological relevance. Acting as a plant growth regulator, (±)-7-epiJasmonic acid triggers various signal transduction pathways, which can either promote growth or inhibit it, likely as a response to stress conditions.