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Abstract Methods are described which allow the synthesis of several plant indole alkaloids and their metabolites at different scales. Compounds synthesized include gramine (1) (3-di-methylaminomethylindole) which is directly derived from indole, while its biosynthetic precursors 3-aminomethylindole (3) and 3-methylaminomethylindole (2) as well as indole-3-carboxylic acid (7) are synthesized via indole-3-aldehyde (6). Slight changes of the experimental conditions allow syntheses with high yields not only at the molar but also at the μmolar level. This is extremely useful when isotope labelled compounds of high specific radioactivity are required for studies of plant metabolism.

Cell suspension cultures of Hordeum vulgare were shown to contain N-methyltyramine, hordenine and gramine. Cell cultures of barley as well as of wheat, parsley, soybean, mungbean and chick pea degraded the phenylethylamines hordenine, tyramine and dopamine to CO,. Intermediates were N-methyltyramine and p-hydroxyphenylacetic acid, p-hydroxybenzoic acid and 3, 4dihydroxyphenylacetic acid, respectively. Oxidative polymerisation of phenylethylamines and intermediate phenols was also observed. Phenylethylamine catabolism in plants and animals seems to be similar. Results are taken from the Ph. D. thesis of E. MEYER, Munster 1977. IAA = B-indoleacetic aci,d, N A A = a-naphthylacetic acid, 2,4-D = 2,4-dichloroacetic acid, BAP = 6-benzylaminopurine, TLC = thin layer chromatography, GLC = gas liquid dlromatography, pCPA = p-chlorphenoxyacetic acid, PC = paper chromatography.