PubMed · 5439235
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R G Cooke, J G Down. 1970. Naturally occurring optically active flavans.. https://doi.org/10.1016/s0040-4039(01)97900-6
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Here we demonstrate the application of 3-D NMR spectroscopy to structural studies of humic substances, the most abundant of organic compounds on earth. The increased spectral dispersion provided by the additional dimension is proven to be highly advantageous in separating the overlapping signals observed in 2-D spectra. Assignments of the major aliphatic structures and selected aromatic moieties are given as examples. We find that in a forest soil fulvic acid the major aliphatic materials are likely derived from leaf cuticles and further demonstrate that lignin signatures can be identified among the aromatic species. Once identified from the 3-D spectra, these structures can be assigned using the partial information available in 2-D, and in some cases, in the 1-D spectra. These signals are demonstrated to be characteristic to given samples of natural organic matter, and the case is made for their use as indicators of terrestrial biomarkers in mixtures of compounds with unknown origins.
The retention of phenol, o-cresol, 2,4-dichlorophenol (DCP), and their peroxidase-catalyzed polymerization products was evaluated on two surface soils. The extractability of the parent solutes and their polymerization products was also investigated. (14)C-Labeled radioisotopes were used to quantify the contaminant retained on soil as water-extractable, methanol-extractable, humic/fulvic (HA/FA) acid-bound, and soil/humin bound. Between 2 and 20% of the solute retained on soil after a 7-day contact period remained bound to the HA/FA and soil/humin components in unamended soils; in the presence of peroxidase this amount was as high as 40-75%. The alkali-extractable HA/FA component contained the largest fraction of radioactivity in peroxidase-amended soils. Whereas the soil organic matter content was the predominant factor controlling the extent of sorption of the parent phenols, the clay content and particle surface area appeared to contribute to the retention of the polymerization products. High molecular weight oligomers produced during peroxidase-mediated polymerization of phenols associate strongly with soil components and are likely incorporated into the soil organic matter via oxidative coupling reactions.
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