Degradation of Phenylethylamines in Plant Cell Suspension Cultures

Abstract

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.

Cytokinin Antagonist Activity of Substituted Phenethylamines in Plant Cell Culture

“…A wide variety of substituted phenethylamines have been identified in plants, including norepinephrine (3,12), tyramine (9,24), dopamine (13,19), adrenaline and dopa (1 1), N-methyl tyramine (22), and octopamine (16,26). Although these compounds have been extensively studied in insects, mollusks, and crustaceans for their neurotransmitter properties (6,18), their functions in plants remain relatively obscure.…”

“…A wide variety of substituted phenethylamines have been identified in plants, including norepinephrine (3, 12), tyramine (9, 24), dopamine (13,19), adrenaline and dopa (1 1), N-methyl tyramine (22), and octopamine (16,26 Tobacco (Nicotiana tabacuum cv H425), cotton (Gossypium hirsutum cv DPL6 1), corn (Zea mays var A188), soybean (Glycine max cv Hardin, Williams, Peking, and Essex), and sunflower (Helianthus annuus L.) seeds were sterilized with commercial bleach (4-6% NaOCl) diluted 1:5 with water for 10 min, washed three times with sterile distilled water, and germinated on filter paper.…”

Aromatic Monoamine-Induced Immediate Oxidative Burst Leading to an Increase in Cytosolic Ca2+ Concentration in Tobacco Suspension Culture

“…PEA and tyramine are the major monoamine constituents of tobacco and other plant tissues (Smith 1977, Slocum et al 1989. The metabolism (Endress et al 1984) and catabolism (Meyer and Barz 1978) of PEA and its derivatives seem to be similar in plants and animals. Applewhite (1973) has investigated the distribution of norepinephrine and serotonin in several so called 'action plants' and found that these two compounds are very abundant in the organs of movement, pulvini and tendrils, suggesting their role as 'plant neural transmitters'.…”

On the Degradation of Nicotine in Nicotiana Cell Suspension Cultures

“…In view of strong N-demethylation reactions of foreign compounds previously found in cell cultures [25] further enzymatic experiments with (methyl-i4C)-nicotine will have to show whether the enzyme(s) involved are specific for nicotine. Such studies will possibly also explain the puzzling observation of incorporation of label from the methylgroup of nicotine (table I) or hordenine [25] into oligomeric and polymeric material. Such reactions have so far never been observed in 0-demethylation studies in cell cultures [26, 271 where the liberated 0-methylgroups were quantitatively oxidized to CO,.…”