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Main Conclusion: Exogenous phenylalanine stunted annual ryegrass but not switchgrass or winter grain rye, with deuterium incorporation up to 3% from phenyalanine-d 8 . Toxicity to duckweed varied with illumination intensity and glucose uptake. Isotopic labeling of biomolecules through biosynthesis from deuterated precursors has successfully been employed for both structural studies and metabolic analysis. Phenylalanine is the precursor of many products synthesized by plants, including the monolignols used for synthesis of lignin. Possible allelochemical effects of phenylalanine have not been reported, although its deamination product cinnamic acid is known to have deleterious effects on root elongation and growth of several plant species. The effects of phenylalanine and its deuterated analog phenylalanine-d 8 added to growth media were studied for annual ryegrass (Lolium multiflorum), winter grain rye (Secale cereale), and switchgrass (Panicum virgatum) cultivated under hydroponic conditions. Growth of annual ryegrass was inhibited by phenylalanine while switchgrass and rye were not significantly affected. Growth was less affected by deuterated phenylalanine-d 8 than by its protiated counterpart, which may be a typical deuterium kinetic isotope effect resulting in slower enzymatic reaction rates. Deuterium incorporation levels of 2-3% were achieved in biomass of switchgrass and annual ryegrass. Both protiated and deuterated phenylalanine were moderately toxic (IC25 values 0.6 and 0.8 mM, respectively) to duckweed (Lemna minor) grown using a 12 h diurnal cycle under photoautotrophic conditions. A significant increase in toxicity, greater for the deuterated form, was noted when duckweed was grown under higher intensity, full spectrum illumination with a metal halide lamp compared to fluorescent plant growth lamps emitting in the blue and red spectral regions. Supplementation with glucose increased toxicity of phenylalanine consistent with synergy between hexose and amino acid uptake that has been reported for duckweed.

To characterize the range of variation in lignan content and composition caused by genotype and environment, seven dietary lignans, i.e., 7-hydroxymatairesinol, secoisolariciresinol, matairesinol, lariciresinol, pinoresinol, medioresinol, and syringaresinol, were analyzed by high-performance liquid chromatography-tandem mass spectrometry in whole-grain extracts of cereal samples collected at eight locations in Finland. In all, 28 winter rye, 73 spring wheat, and 55 spring oat samples were analyzed, representing 6, 9, and 5 cultivars, respectively. The total lignan content showed huge variations within the same cereal species: the range was 2500-6700 microg/100 g in the rye samples, 340-2270 microg/100 g in the wheat samples, and 820-2550 microg/100 g in the oat samples. The variations seemed to depend largely upon genetic differences. In rye, also environmental conditions affected the lignan content through grain size; smaller grains had significantly lower total lignan, syringaresinol, and lariciresinol content than larger grains. This study shows that varying cereal lignan concentrations reported in different studies may be, besides differences in analytical methods, largely dependent upon natural variations.