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

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Farnesyl and α-ionylideneethyl compounds with tertiary and quaternary amine functional groups were synthesized and their effects on abscisic acid (ABA) biosynthesis of Cercospora rosicola observed. The trimethylammonium compounds were lethal at 100μM and inhibitory at 10 μM, but lesser amounts of α-ionylideneethyltrimethylammonium iodide enhanced ABA biosynthesis. N, N-Dimethylfarnesylamine had little effect on ABA biosynthesis. N, N-Dimethyl (2Z, 4E)- and (2E, 4E)-α-ionylideneethylamines inhibited ABA biosynthesis at 100μM but had no or little effect at lower concentrations. Farnesol and farnesylpyrophosphate (FPP) enhanced ABA biosynthesis. FPP appears to be both a precursor and an inducer and farnesol is an inducer of ABA biosynthesis. N, N-Dimethyl (2Z, 4E)- and (2E, 4E)-α-ionylideneethylamines were converted to N, N-dimethyl (2Z, 4E))- and (2E, 4E)-4-keto-α-ionylideneethylamines, respectively. These conversions are analogous to those reported for α-ionone and α-ionylideneacetic acids and show that basic as well as acidic and neutral compounds with α-ionone type rings can undergo oxidation at the 4-position. α-Ionylideneacetic acids inhibited growth of C. rosicola and the dimethylamines enhanced growth. Complete feedback inhibition was obtained with 400 μM of ABA.
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