Description
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.
1 12-
oxo PDA is one of the best studied end metabolites of this enzymatic pathway.
2 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.
References
1. Crombie, L., and Mistry, K.M.
Synthesis of 12-oxophytodienoic acid (12-oxoPDA) and the compounds of its enzymic degradation cascade in plants, OPC-8:0, -6:0, -4:0 and -2:0 (epi-jasmonic acid), as their methyl esters Journal of the Chemical Society 1,1981-1991(1991).
2. Hamberg, M., and Gardner, H.W.
Oxylipin pathway to jasmonates: Biochemistry and biological significance Biochim. Biophys. Acta 1165(1),1-18(1992).
