The chemistry and biochemistry of organic components in the soil solutions of wheat rhizospheres

Advances in Agronomy

Volumn 121, Issue , 2013, Pages 179-251

  Monreal, Carlos M ^a   Schnitzer, Morris ^a  

^a AGRICULTURE AND AGRI FOOD CANADA   (Canada)

Author keywords

Biochemical function; Chemical compounds; Humic substances; Mass spectrometry; Soil solution; Wheat rhizosphere exudates

Indexed keywords

EID: 84879254262     PISSN: 00652113     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-407685-3.00004-9     Document Type: Chapter

References (209)

1. Adom K.K., Liu R.H. Antioxidant activity of grains. J. Agric. Food Chem. 2002, 50:6182-6187.
2. Aguilar J.M.M., Ashby A.M., Richards A.J.M., Loake G.J., Watson M.D., Shaw C.H. Chemotaxis of Rhizobium leguminosarum bv Phaseoli towards flavonoid inducers of the symbiotic nodulation genes. J. Gen. Microbiol. 1988, 134:2741-2746.
3. Alberts B., Johnson A., Lewis J., Raff M., Roberts K., Walter P. Molecular Biology of the Cell 2002, 1616. Garland Science, New York. fourth ed.
4. Allan M. Darwin and His Flowers 1977, 278-290. Faber and Faber, London.
5. Amelung W. Nitrogen biomarkers and their fate in soil. J. Plant Nutr. Soil Sci. 2003, 166:677-686.
6. Amelung W., Zhang X., Flach K.W. Amino acids in grassland soils: climatic effects on concentrations and chirality. Geoderma 2006, 130:207-217.
7. Aniszewski T. Alkaloids-Secrets of Life: Alkaloid Chemistry, Biological Significance, Applications and Ecological Significance Role 2007, 316. Elsevier Amsterdam, The Netherlands. first ed.
8. Anraku Y. Transport and utilization of amino acids by bacteria. Microorganisms and Nitrogen Sources: Transport and Utilization of Amino Acids, Peptides, Proteins and Related Substrates 1980, 9-34. John Wiley and Sons, New York. J.W. Payne (Ed.).
9. Austin M.B., Noel J.P. The chalcone synthase superfamily of type III polyketide synthases. Nat. Prod. Rep. 2003, 20:79-110.
10. Bais H.P., Weir T.L., Perry L.G., Gilroy S., Vivanco J.M. The role of root exudates in rhizosphere interactions with plants and other organisms. Annu. Rev. Plant Biol. 2006, 57:233-266.
11. Barber D.A., Gunn K.B. The effect of mechanical forces on the exudation of organic substances by the roots of cereal plants grown under sterile conditions. New Phytol. 1974, 73:39-45.
12. Barber D.A., Martin J.K. The release of organic substances by cereal roots into soil. New Phytol. 1976, 76:69-80.
13. Beck H.C., Hansen A.M., Lauritsen F.R. Novel pyrazine metabolites found in polymyxin biosynthesis by Paenibacillus polymyxa. FEMS Microbiol. Lett. 2003, 220:67-73.
14. Beckey H.D. Principles of Field Ionization and Field Desorption Mass Spectrometry 1977, 335. Pergamon Press, Oxford, UK.
15. Begley T.P., Kinsland C., Mehl R.A., Osterman A., Dorrestein P. The biosynthesis of nicotinamide adenine dinucleotides in bacteria. Vitam. Horm. 2001, 61:103-119.
16. Beneviste P. Sterol biosynthesis. Annu. Rev. Plant Physiol. 1986, 37:275-308.
17. Beneviste P. Biosynthesis and accumulation of sterols. Annu. Rev. Plant Biol. 2004, 55:429-457.
18. Bennett J.W. From molecular genetics and secondary metabolism to molecular metabolites and secondary genetics. Can. J. Bot. 1995, 73:S917-S924.
19. Bergé J.-P., Barnathan G. Fatty acids from lipids of marine organisms: molecular biodiversity, roles as biomarkers, biologically active compounds, and economical aspects. Adv. Biochem. Eng. Biotechnol. 2005, 96:49-125.
20. Bernards M.A. Demystifying suberin. Can. J. Bot. 2002, 80:227-240.
21. Bernards M.A., Lopez M.L., Zajicek J., Lewis N.G. Hydroxycinnamic acid derived polymers constitute the polyaromatic domain of suberin. J. Biol. Chem. 1995, 270:7382-7386.
22. Bertin C., Yang X., Weston L.A. The role of root exudates and allelochemicals in the rhizosphere. Plant Soil 2003, 256:67-83.
23. Bird C.W., Lynch J.M. Formation of hydrocarbons by microorganisms. Chem. Soc. Rev. 1974, 3:309-328.
24. Blunt S.A., Silver J.C. Molecular cloning and characterization of two distinct hsp85 sequences from the steroid responsive fungus Achlya ambisexualis. Curr. Genet. 1991, 19:383-388.
25. Bolaños-Vásquez M.C., Werner D. Effects of Rhizobium tropici, R. etli, and R. leguminosarum bv. phaseoli on nod gene-inducing flavonoids in root exudates of Phaseolus vulgaris. Mol. Plant Microbe Interact. 1997, 10:339-346.
26. Bollina V., Kumaraswany G.K., Kushalappa A.C., Choo T.M., Dion Y., Rioux S., Faubert D., Hamzehzarghani H. Mass spectrometry-based metabolomics application to identify quantitative resistance-related metabolites in barley against Fusarium head blight. Mol. Plant Pathol. 2010, 11:769-782.
27. Boyd S.A., Shelton D.R., Berry D., Tiedje J.M. Anaerobic degradation of phenolic compounds in digested sludge. Appl. Environ. Microbiol. 1983, 46:50-54.
28. Brown E.G. Ring Nitrogen and Key Biomolecules 1998, 243. Kluwer Academic Publishers, Dordrecht, The Netherlands.
29. Brown E.G., Diffin F. Biosynthesis and metabolism of pyrazole by Cucumis sativus: enzymic cyclization and dehydrogeneation of 1,3 diamino propane. Phytochemistry 1990, 29:469-478.
30. Buetal D.E., Levedahl B.H. Responses of microorganisms to sterols and steroids. Annu. Rev. Microbiol. 1964, 18:167-194.
31. 13 acids. Physiol. Plantarum. 1950, 3:175-184.
32. Cerniglia C.E. Biodegradation of polycyclic aromatic hydrocarbons. Biodegradation 1992, 3:351-368.
33. Chakraborty D.P., Roy S. Carbazole alkaloids IV. Progress in the Chemistry of Natural Products 2003, 245. Springer-Verlag, Wien, Austria. W. Herz, H. Falk, G.W. Kirby (Eds.).
34. Chiavari G., Galletti G.C. Pyrolysis-gas chromatography/mass spectrometry of amino acids. J. Anal. Appl. Pyrolysis 1992, 24:123-137.
35. Collins P.A., Knowles C.J. The utilization of nitriles and amides by Nocardia rhodochrous. J. Gen. Microbiol. 1983, 129:711-718.
36. Conn E.E. Cyanogenic glycosides. Encyclopedia of Plant Physiology 1980, vol. 8:461-492. Springer, Berlin. E.A. Bell, B.V. Chapman (Eds.).
37. Conn E.E. Biosynthesis of cyanogenic glycosides. Cyanide in Biology 1981, 183-196. Academic Press, London. B. Vennesland (Ed.).
38. Corcuera L.J. Effects of indole alkaloids from gramineae on aphids. Phytochemistry 1984, 23:539-541.
39. Crozier A., Lean M.E.J., McDonald M.S., Black C. Quantitative analysis of the flavonoid content of commercial tomatoes, onions, lettuce, and celery. J. Agric. Food Chem. 1997, 45:590-595.
40. Dakora F.D., Phillips D.A. Root exudates as mediators of mineral acquisition in low-nutrient environments. Plant Soil 2002, 245:35-47.
41. Darwent M.J., Paterson E., McDonald A.J.S., Tomos A.D. Biosensor reporting of root exudation from Hordeum vulgare in relation to shoot nitrate concentration. J. Exp. Bot. 2003, 54:325-334.
42. Das A., Khosla C. Biosynthesis of aromatic polyketides in bacteria. Acc. Chem. Res. 2009, 42:631-639.
43. Da Silva M.F., Soares M.S., Fernandes J.B., Viera P.C. Alkyl, aryl, alkylarylquinoline, and related alkaloids. Alkaloids Chem. Biol. 2007, 64:139-214.
44. Davis R.H., Nahrstedt A. Biosynthesis of cyanogenic glucosides in butterflies and moths: effective incorporation of 2-methylpropanenitrile and 2-methylethylbutanenitrile into linamarin and lotaustralin y Zygaenaand Heliconius species (Lepidoptera). Insect Biochem. 1987, 17:689-693.
45. de Souza W., Rodrigues J.C.F. Sterol biosynthesis pathway as target for anti-trypanosomatid drugs. Interdiscip. Perspect. Infect. Dis. 2009, 2009:1-19.
46. Dettmer K., Aronov P.A., Hammock B.D. Mass spectrometry-based metabolomics. Mass Spectrom. Rev. 2007, 26:51-78.
47. Dhillon J., Shivaraman N. Biodegradation of cyanide compounds by a Pseudomonas species (S1). Can. J. Microbiol. 1999, 45:201-208.
48. Dickschat J.S., Wickel S., Bolten C.J., Nawrath T., Schulz S., Wittmann C. Pyrazine biosynthesis in Corynebacterium glutamicum. Eur. J. Org. Chem. 2010, 2010:2687-2695.
49. Fabre N., Rustan I., de Hoffman E., Quetin-Leclerq J. Determination of flavone, flavonol, and flavanone aglycones by negative ion liquid chromatography electrospray ion trap mass spectrometry. J. Am. Soc. Mass Spectrom. 2001, 12:707-715.
50. Fetzner S. Bacterial degradation of pyridine, indole, quinoline, and their derivatives under different redox conditions. Appl. Microbiol. Biotechnol. 1998, 49:237-250.
51. Finch P., Hayes M.H.B., Stacey M. The biochemistry of soil polysaccharides. Soil Biochemistry 1971, vol. 2:257-319. Marcel Dekker Inc., New York. A.D. Maclaren, J. Skujins (Eds.).
52. Firn R.D., Jones C.G. Natural products: a simple model to explain chemical diversity. Nat. Prod. Rep. 2003, 20:382-391.
53. Flaig, W.J.A., 1988. Generation of model chemical precursors. In: Frimmel, F.H., Christman, R.F. (Eds.), Humic Substances and Their Role in the Environment 45. Report of the Dahlem workshop. John Wiley & Sons, USA, pp. 75-92.
54. Flaig W., Beutelspacher H., Rietz E. Chemical composition and physical properties of humic substances. Soil Components. I. Organic components 1975, 1-211. Springer, New York. J.E. Grieseking (Ed.).
55. 27 apocarotenoids, shedding light on the functional role of CCD1. Plant Phys. 2008, 148:1267-1282.
56. Foster J.W., Moat A.G. Nicotinamide adenine dinucleotide biosynthesis and pyridine nucleotide cycle metabolism in microbial systems. Microbiol. Rev. 1980, 44:83-105.
57. Frey M., Stettner C., Paré P.W., Schmelz E.A., Tumlinson J.H., Gierl A. An herbivore elicitor activates the gene for indole emission in maize. Proc. Natl. Acad. Sci. USA 2000, 97:14801-14806.
58. Funa N., Ozawa H., Hirata A., Horinouchi S. Phenolic lipid synthesis by type III polyketide synthases is essential for cyst formation in Azotobacter vinelandii. Proc. Natl. Acad. Sci. USA 2006, 103:6356-6361.
59. Geoghegan M., Brian R.C. Influence of bacterial polysaccharides on aggregate formation in soils. Nature 1946, 158:837.
60. Ghorab M.M., Abdel-Hamide S.G., Farrag A.A. Synthesis of quinolines, pyranoquinolines, furoquinolines, thieno-quinoline and theyr effect on the ultrastructure of some pathogenic microorganisms. Acta Pol. Pharm. 2001, 58:175-184.
61. Goosen N., Huinen R.G.M., van de Putte P. A 24-amino-acid polypeptide is essential for the biosynthesis of the coenzyme pyrrolo-quinoline-quinone. J. Bacteriol. 1992, 174:1426-1427.
62. Gördes D., Kolukisaoglu U., Thurow K. Uptake and conversion of D-amino acids in Arabidopsis thaliana. Amino Acids 2011, 40:553-563.
63. Graça J., Pereira H. Suberin in potato periderm: glycerol, long chain monomers, and glyceryl and feruloyl dimers. J. Agric. Food Chem. 2000, 48:5476-5483.
64. Graça J., Santos S. Glycerol-derived ester oligomers from cork suberin. Chem. Phys. Lipids 2007, 144:96-107.
65. Graham J.H., Linderman R.G. Ethylene production by ectomycorrhizal fungi, fusarium oxysporum f.sp. pini, and by aseptically synthesized ectomycorrhizae and fusarium-infected Douglas-fir roots. Can. J. Microbiol. 1980, 26:1340-1347.
66. Grifoll M., Selifonov S.A., Getlin C.V., Chapman P.J. Actions of a versatile fluorene-degrading bacterial isolate on polycyclic aromatic compounds. Appl. Environ. Microbiol. 1995, 61:3711-3723.
67. Grotewold E. The Science of Flavonoids 2006, 279. Springer Science+Business Media Inc., New York, NY.
68. Gudjónsdóttir S. Growth-promoting effects of fatty acids on excised wheat roots and oat coleoptiles. Phys. Plant. 1966, 19:523-540.
69. Guirguis M.A., Kunc F., Vancura V. Presence and oxidation of amino acids in the rhizosphere and non-rhizosphere soil. Folia Microiol. (Praha) 1969, 14:1-12.
70. Guo B.-Y., Peng Z.-L., Han F., Shan X.-Q. Study of low-molecular weight organic acids in maize roots under the stress of cadmium using capillary zone electrophoresis. J. Sep. Sci. 2007, 30:2742-2747.
71. Guo W., Li D., Tao Y., Gao P., Hu J. Isolation and description of a stable carbazole degrading microbial consortium consisting of Chryseobacterium sp. NCY and Achromobacter sp. NCW. Curr. Microbiol. 2008, 57:251-257.
72. Guy R.K. Inhibition of sonic hedge-hog autoprocessing in cultured mammalian cells by sterol deprivation. Proc. Natl. Acad. Sci. USA 2000, 97:7307-7312.
73. Han J., Chan H.W.S., Calvin M. Biosynthesis of alkanes in Nostoc muscorum. J. Am. Chem. Soc. 1969, 21:5156-5159.
74. Hartman M.A. Sterol metabolism and function in higher plants. Lipid Metabolism and Membrane Biogenesis 2003, 183-211. Top. Curr, Genet, 6. G. Daum (Ed.).
75. Harwood J.L. Fatty acid biosynthesis. Plant Lipids: Biology, Utilisation and Manipulation 2005, 27-66. Blackwell Publishing, Oxford. D.J. Murphy (Ed.).
76. Hassan S., Mathesius U. The role of flavonoids in root-rhizosphere signalling: opportunities and challenges for improving plant-microbe interactions. J. Exp. Bot. 2012, 63:3429-3444. 10.1093/jxb/err430.
77. Hatfield R., Vermerris W. Lignin formation in plants. The dilemma of linkage specificity. Plant Physiol. 2001, 126:1351-1357.
78. Hempfling R., Schulten H.-R. Chemical characterization of organic matter in forest soils by Curie-point pyrolysis-field ionization mass spectrometry. Org. Geochem. 1990, 15:131-145.
79. Hendrix J.W. Sterols in growth and reproduction of fungi. Annu. Rev. Phytopathol. 1970, 8:111-130.
80. Henry H.A.L., Jefferies R.L. Free amino acid, ammonium and nitrate concentrations in soil solutions of a grazed coastal marsh in relation to plant growth. Plant Cell Environ. 2002, 25:665-675.
81. Hertweck C. The biosynthetic logic of polyketide diversity. Angew. Chem. Int. Ed. Engl. 2009, 48:4688-4716.
82. Hill P.W., Quilliam R.S., DeLuca T.H., Farrar J., Farrell M., Roberts P., Newsham K.K., Hopkins D.W., Bardgett R.D., Jones D.L. Acquisition and assimilation of nitrogen as peptide-bound and D-enantiomers of amino acids by wheat. PLoS One 2011, 6:1-4.
83. Hill P.W., Farrar J., Roberts P., Farrell M., Grant H., Newsham K.K., Hopkins D.W., Bardgett R.D., Jones D.L. Vascular plant success in a warming Antarctic may be due to efficient nitrogen acquisition. Nat. Clim. Chang. 2011, 1:50-53.
84. Holman R.T., Nichols P.C. Characterization of the lipids of some orchids. Phytochemistry 1972, 11:333-337.
85. Hopwood D.A. Genetic contributions to understanding polyketides synthases. Chem. Rev. 1997, 97:2465-2497.
86. Horbowicz M., Chrzanowski G., Koczkodaji D., Mitus J. The effect of methyl jasmonate vapors on content of phenolic compounds in seedlings of common buckwheat (Fagopyrum esculentum Moench). Acta Soc. Bot. Pol. 2011, 80:5-9.
87. Horiguchi G., Fuse T., Kawakami N., Kodama H., Iba K. Temperature-dependent translational regulation of the ER ω-3 fatty acid desaturase gene in wheat root tips. Plant J. 2000, 24:805-813.
88. Jokic A., Schulten H.R., Cutler J.N., Schnitzer M., Huang P.M. A significant abiotic pathway for the formation of unknown nitrogen in nature. Geophys. Res. Lett. 2004, 31:L05502.
89. Kaneshiro T., Kuo T.M., Nakamura L.K. Conversion of unsaturated fatty acids by bacteria isolated from compost. Curr. Microbiol. 1999, 38:250-255.
90. Karpen H.E., Bukowski J.T., Hughes T., Gratton J.P., Sessa W.C., Gailani M.R. The sonic hedgehog receptor patched associates with caveolin-1 in cholesterol rich microdomains of the plasma membrane. J. Biol. Chem. 2001, 276:19503-19511.
91. Kefeli V.I., Kalevitch M.V., Borsari B. Phenolic cycle in plants and environment. J. Cell Mol. Biol. 2003, 2:13-18.
92. Kenrick P. The origin of roots. The Hidden Half 2002, 1-2. Marcel Dekker Inc., New York. Y. Waisel, A. Eschel, L. Kafkafi (Eds.).
93. Kidd P.S., Llugany M., Poschenrieder C., Gunsé B., Barceló J. The role of root exudates in aluminium resistance and silicon-induced amelioration of aluminium toxicity in three variety of maize (Zea mays L.). J. Exp. Bot. 2001, 52:1339-1352.
94. Kim S.H., Ko H., Bang H.S., Park S.H., Kima D.G., Kwon H.C., Kim S.Y., Shin J., Oh D.J. Coprismycins A and B, neuroprotective phenylpyridines from the dung beetle-associated bacterium, Streptomyces sp. Bioorg. Med. Chem. Lett. 2011, 21:5715-5718.
95. Knölker H.-J., Reddy K.R. Isolation and synthesis of biologically active carbazole alkaloids. Chem. Rev. 2002, 102:4303-4327.
96. Kobayashi M., Nagasawa T., Yamada H. Nitrilase of Rhodococcus rhodochrous J1. Purification and characterization. Eur. J. Biochem. 1989, 182:349-356.
97. Kodicek E., Worden A.N. The effect of unsaturated fatty acids on Lactobacillus helveticus and other Gram-positive micro-organisms. Biochem. J. 1945, 39:78-85.
98. Kögel I., Hempfling R., Zech R., Hatcher P.G., Schulten H.-R. Chemical composition of the organic matter in forest soils. I. Forest litter. Soil Sci. 1988, 146:126-136.
99. Koyama G., Maeda K., Umezawa H. The structural studies of formycin and formycin B. Tetrahedron Lett. 1966, 6:597-602.
100. Labinger J.A., Bercaw J.E. Understanding and exploiting C-H bond activation. Nature 2002, 417:507-514.
101. Ladygina N., Dedyukhina E.G., Vainshtein M.B. A review on microbial synthesis of hydrocarbons. Process Biochem. 2006, 41:1001-1014.
102. Lattanzio V., Lattanzio V.M.T., Cardinali A. Role of phenolics in the resistance mechanisms of plants against fungal pathogens and insects. Phytochemistry: Advances in Research 2006, 23-67. Research SingPost, Kerala, India. F. Imperato (Ed.).
103. Lautru S., Song L., Demange L., Lombès T., Galons H., Challis G.L., Pernodet J.L. A sweet origin for the key Congocidine precursor 4-acetamidopyrrole-2-carboxylate. Angew. Chem. Int. Ed. Engl. 2012, 51:1-6.
104. Lehninger A.L. Principles of Biochemistry 1982, 1011. Worth Publishers, Inc., New York.
105. Leinhos V., Vacek O. Biosynthesis of auxins by phosphate-solubilizing rhizobacteria from wheat and rye. Microbiol. Res. 1994, 149:31-35.
106. Leinweber P., Eckhardt K.-U., Fischer H., Kuzyakov Y. A new rapid micro-method for the molecular-chemical characterization of rhizodeposits by field-ionization mass spectrometry. Rapid Commun. Mass Spectrom. 2008, 22:1230-1234.
107. Leistner E., Zenk M.H. Mevalonic acid a precursor of the substituted benzenoid ring of rubiaceae-anthraquinones. Tetrahedron Lett. 1968, 9:1395-1396.
108. Liang Y., Gardner D.R., Miller C.D., Chen D., Anderson A.J., Weimer B.C., Sims R.C. Study of biochemical pathways and enzymes involved in pyrene degradation by Micobacterium sp. strain KMS. Appl. Environ. Microbiol. 2006, 72:7821-7828.
109. Lichtenhaler H.K., Schwender J., Disch A., Rohmer M. Biosynthesis of isoprenoids in higher plant chloroplasts proceeds via a mevalonate-independent pathway. FEBS Lett. 1997, 400:271-274.
110. Lin C., Shen B., Xu Z., Köllner T.G., Degenhardt J., Dooner H.K. Characterization of the monoterpene synthase gene tps26, the Ortholog of a Gene induced by insect herbivory in maize. Plant Phys. 2008, 146:940-951.
111. Lin S.-M., Tang Y.L., Lin C.L. Efficient bioconversion of compactin to pravastatin by thequinoline-degrading microorganism Pseudonocardia carboxydivorans isolated from petroleum-contaminated soil. Bioresour. Technol. 2011, 102:10187-10193.
112. Liu L., Greaver T.L. A global perspective on below-ground carbon dynamics under nitrogen enrichment. Ecol. Lett. 2010, 13:819-828.
113. Liu S.M., Jones W.J., Rogers J.E. Influence of redox potential on the anaerobic biotransformation of nitrogen-hetero-cyclic compounds in anoxic freshwater sediments. Appl. Microbiol. Biotechnol. 1994, 41:717-724.
114. Lobastova T.G., Sukhodolskaya G.V., Nikolayeva V.M., Baskunov B.P., Turchin K.F., Donova M.V. Hydroxylation of carbazoles by Aspergillus flavus VKM F-1024. FEMS Microbiol. Lett. 2004, 235:51-56.
115. Lynch J.M. Production and phytotoxicity of acetic acid in anaerobic soils containing plant residues. Soil Biol. Biochem. 1978, 10:131-135.
116. Lynch J.M., Gunn K.B., Panting L.M. On the concentration of acetic acid in straw and soil. Plant Soil 1980, 56:93-98.
117. Marschner H. Mineral Nutrition in Higher Plants 1995, Academic Press Ltd., London. second ed.
118. Martin J.P., Richards S.J., Haider K. Properties and decomposition and binding action in soil "humic acid" synthesized by Epicoccum nigrum. Soil Sci. Soc. Am. Proc. 1967, 31:657-662.
119. Mattey M., Harle E.M. Aerobic metabolism of pyrazine compounds by a Pseudomonas species. Biochem. Soc. Trans. 1976, 4:492-494.
120. McMurry J.E., Begley T.P. The Organic Chemistry of Biological Pathways 2005, 477. Roberts and Company Publishers, Colorado.
121. McRae G., Monreal C.M. LC-MS/MS quantitative analysis of fifteen reducing sugars in soil solutions extracted from crop rhizospheres. Anal. Bioanal. Chem. 2011, 400:2205-2215.
122. Metz J.G., Roessler P., Faccioti D., Levering C., Dittrich F., Lassner M., Valentine R., Lardizabel K., Domergue F., Yamada A., Yazawa K., Knauff V., Browse J. Production of polyunsaturated fatty acids by polyketide synthases in both prokaryotes and eukaryotes. Science 2001, 293:290-293.
123. Meyer A., Fischer H., Kuzyakov Y., Fischer K. Improved RP-HPLC and anion-exchange chromatography methods for the determination of amino acids and carbohydrates in soil solutions. J. Plant Nutr. Soil Sci. 2008, 171:917-926.
124. Miethling R., Hecht V., Deckwer W.D. Microbial degradation of quinoline: kinetic studies with Comamonas aci-dovorans DSM 6426. Biotechnol. Bioeng. 1993, 42:589-595.
125. Mitchell R., MacLanahan D., Hurt D., Dalgarn D., Newman D.W. Fatty acids of roots of selected species. Ohio J. Sci. 1974, 74:150-154.
126. Moire L., Schmutz A., Buchala A., Yan B., Stark R.E., Ryser U. Glycerol is a suberin monomer. New experimental evidence for an old hypothesis. Plant Physiol. 1999, 119:1137-1146.
127. Monreal C.M., McGill W.B. Kinetic analysis of cystine cycling through the solution of a Gray Luvisol and an Andept soil. Soil Biol. Biochem. 1989, 21:671-679.
128. Monreal C.M., McGill W.B. The effects of soil amendments on the dynamics of free cystine cycling at steady-state through the solutions of a Black Chernozemic and Andept soil. Soil Biol. Biochem. 1989, 21:695-701.
129. Müller R., Rappert S. Pyrazines: Occurrence, formation and biodegradation. Appl. Microbiol. Biotechnol. 2010, 85:1315-1320.
130. Nakano C., Ozawa H., Akanuma G., Funa N., Horinouchi S. Biosynthesis of aliphatic polyketides by type III polyketide synthase and methyltransferase in Bacillus subtilis. J. Bacteriol. 2009, 191:4916-4923.
131. O'Loughlin E.J., Khermeyer S.R., Sims G.K. Isolation, characterization, and substrate utilization of a quinoline-degrading bacterium. Int. Biodeterior. Biodegradation 1996, 38:107-118.
132. Olsson P.A. Signature fatty acids provide tools for determination of the distribution and interactions of mycorrhizal fungi in soil. FEMS Microbiol. Ecol. 1999, 29:303-310.
133. Ouchiyama N., Zhang Y., Omori T., Kodama T. Biodegradation of carbazole by Pseudomonas sp. CA06 and CA10. Biosci. Biotechnol. Biochem. 1993, 57:455-460.
134. Packter N.M., Steward M.W. Studies on the biosynthesis of phenols in fungi. Biosynthesis of 3,4-dimethoxy-6-methyltoluquinol and gliorosein in Gliocladium roseum I.M.I. 93 065. Biochem. J. 1967, 102:122-132.
135. Park M.O. New pathway for long-chain n-alkane synthesis via 1-alcohol in Vibrio furnissii M1. J. Bacteriol. 2005, 187:1426-1429.
136. Patten C.L., Glick B.R. Bacterial biosynthesis of indole-3-acetic acid. Can. J. Microbiol. 1996, 42:207-220.
137. Pearson A., Budin M., Brocks J.J. Phylogenetic and biochemical evidence for sterol synthesis in the bacterium Gemmata obscuriglobus. Proc. Natl. Acad. Sci. USA 2003, 100:15352-15357.
138. Pereria W.E., Rostad C.E., Updegraff D.M., Bennett J.L. Fate and movement of azaarenes and their anaerobic bio-transformation products in an aquifer contaminated by wood-treatment chemicals. Environ. Toxicol. Chem. 1987, 6:163-176.
139. Pollard M., Beisson F., Li Y., Ohlrogge J.B. Building lipid barriers: Biosynthesis of cutin and suberin. Trends Plant Sci. 2008, 13:236-246.
140. Polya G. Biochemical Targets of Plant Bioactive Compounds. A Pharmacological Reference Guide to Sites of Action and Biological Effects 2003, 847. Taylor and Francis Ltd., CRC Press, London.
141. Ponce M.A., Scervino J.M., Erra-Balsells R., Ocampo J.A., Godeas A.M. Flavonoids from shoots, roots and roots exudates of Brassica alba. Phytochemistry 2004, 65:3131-3134.
142. Poulsen M., Oh D.C., Clardy J., Currie C.R. Chemical analyses of wasp-associated Streptomyces bacteria reveal a prolific potential for natural products discovery. PLoS One 2011, 6:1-8.
143. Quastel J.H. Soil metabolism. Annu. Rev. Plant Phys. 1965, 16:217-240.
144. Rappert S., Botsch K.C., Nagorny S., Francke W., Müller R. Degradation of 2,3-diethyl-5-methylpyrazine by a newly discovered bacterium, Mycobacterium sp. strain DM-11. Appl. Environ. Microbiol. 2006, 72:1437-1444.
145. Redshaw E.S., Zalik S. Changes in lipids of cereal seedlings during vernalization. Can. J. Biochem. 1968, 46:1093-1097.
146. Resnick S.M., Torok D.S., Gibson D.T. Oxidation of carbazole to 3-hydroxycarbazole by naphthalene 1,2-dioxygenase and biphenyl 2,3-dioxygenase. FEMS Microbiol. Lett. 1993, 113:297-302.
147. Rillig M.C., Mummey D.L. Mycorrhizas and soil structure. New Phytol. 2006, 171:41-53.
148. Rohmer M., Bouvier-Nave P., Ourisson G. Distribution of hopanoid triterpenes in prokaryotes. J. Gen. Microbiol. 1984, 130:1137-1150.
149. Rojo F. Degradation of alkanes by bacteria. Environ. Microbiol. 2009, 11:2477-2490.
150. Rovira A.D. Plant root excretions in relation to the rhizosphere effect. Plant Soil 1956, 7:178-194.
151. Rovira A.D., McDougall M. Microbiological and biochemical aspects of the rhizosphere. Soil Biochemistry 1967, vol 1:417-463. Marcel Dekker Inc., New York, Chapter 16, p. 509. A.D. Mclaren, G.H. Peterson (Eds.).
152. Salas M.L., Corcuera L.J. Effect of environment on gramine content in barley leaves and susceptibility to the aphid Schizaphis Graminum. Phytochemistry 1991, 30:3237-3240.
153. Sasse F., Steinmetz H., Höfle G., Reichenbach H. Archazolids, new cytotoxic macrolactones from Archangium gephyra (Myxobacteria). Production, isolation, physico-chemical and biological properties. J. Antibiot. (Tokyo) 2003, 56:520-525.
154. Schaller H. The role of sterols in plant growth and development. Prog. Lipid Res. 2003, 42:163-175.
155. Schirmer A., Rude M.A., Li X., Popova E., del Cardavre S.B. Microbial biosynthesis of alkanes. Science 2010, 329:559-562.
156. Schlichting A., Leinweber P. New evidence for the molecular-chemical diversity of potato plant rhizodeposits obtained by pyrolysis-field ionisation mass spectrometry. Phytochem. Anal. 2009, 20:1-13.
157. Schmidt A.W., Reddy K.R., Knölker H.-J. Occurrence, biogenesis, and synthesis of biologically active carbazole alkaloids. Chem. Rev. 2011, 112:3193-3328.
158. Schnitzer M. A lifetime perspective on the chemistry of soil organic matter. Adv. Agron. 2000, 68:1-58.
159. Schnitzer M., Khan S.U. Humic Substances in the Environment 1972, Dekker, New York.
160. Schnitzer M., Monreal C.M. Quo vadis soil organic matter research? A biological link to the chemistry of humification. Adv. Agron. 2011, 113:139-213.
161. Schnitzer M., Schulten H.R. The analysis of soil organic matter by pyrolysis-field ionization mass spectrometry. Soil Sci. Soc. Am. J. 1992, 56:1811-1817.
162. Schnitzer M., Schulten H.-R. Analysis of organic matter in soil extracts and whole soils by pyrolysis-mass spectrometry. Adv. Agron. 1995, 55:168-217.
163. Schnitzer M., Schulten H.-R. New ideas on the chemical make-up of soil humic and fulvic acids. Future Prospects for Soil Chemistry 1998, 153-177. Soil Science Society of America, Madison, WI, Special publication No. 55. P.M. Huang, D.L. Sparks, S.A. Boyd (Eds.).
164. Schröter H.B., Neumann D., Katritzky A.R., Swinbourne F.J. Withasomine, a pyrazole alkaloid from Withania somnifera. Tetrahedron 1966, 22:2895-2897.
165. Schulten H.-R. Relevance of analytical pyrolysis studies to biomass conversion. J. Anal. Appl. Pyrolysis 1984, 12:149-187.
166. Schulten H.-R. Relevance of analytical pyrolysis studies to biomass conversion. J. Anal. Appl. Pyrolysis 1987, 6:251-272.
167. Schulten H.-R. Pyrolysis of soft ionization mass spectrometry of aquatic/terrestrial humic substances and soils. J. Anal. Appl. Pyrolysis 1987, 12:149-187.
168. Schulten H.-R. Analytical pyrolysis and computational chemistry of aquatic humic substances and dissolved organic matter. J. Anal. Appl. Pyrolysis 1999, 49:385-415.
169. Schulten H.-R., Schnitzer M. The chemistry of soil organic nitrogen: A review. Biol. Fertil. Soils 1998, 26:1-15.
170. Schulten H.-R., Hempfling R., Zech W. Discriminating horizons in a moder profile by Field Ionization mass spectrometry and pattern recognition. Geoderma 1988, 41:211-222.
171. Schulz S., Dickschat J.S. Bacterial volatiles: the smell of small organisms. Nat. Prod. Rep. 2007, 24:814-842.
172. Schwarz G., Senghas E., Erben E., Schäfer B., Lingens F., Höke H. Microbial metabolism of quinoline and related compounds: I. Isolation and characterization of quinoline-degrading bacteria. Syst. Appl. Microbiol. 1988, 10:185-190.
173. Seo J.S., Keum Y.S., Cho I.K., Li Q.X. Degradation of dibenzothiophene and carbazole by Arthrobacter sp. P1-1. Int. Biodeterior. Biodegradation 2006, 58:36-43.
174. Seo J.S., Keum Y.S., Li Q.X. Bacterial degradation of aromatic compounds. Int. J. Environ. Res. Public Health 2009, 6:278-309.
175. Siebenberg S., Burkard N., Knuplesch A., Gust B., Grond S., Heide L. Two pathways for pyrrole formation in Coumermycin A1 biosynthesis: The central pyrrole moiety is formed from L-threonine. Chembiochem 2011, 12:2677-2685.
176. Simpson A.J., McNally D.J., Simpson M.J. NMR spectroscopy in environmental research: from molecular interactions to global processes. Prog. Nucl. Magn. Reson. Spectrosc. 2011, 58:97-175.
177. Singh G.B., Srivastava S., Gupta S., Gupta N. Evaluation of carbazole degradation by Enterobacter sp. isolated from hydrocarbon contaminated soil. Recent Res. Sci. Technol. 2011, 3:44-48.
178. Sorge C., Schnitzer M., Schulten H.-R. In-source pyrolysis-field ionization mass spectrometry and Curie-point pyrolysis-gas chromatography/mass spectrometry of amino acids in humic substances and soils. Biol. Fertil. Soils 1993, 16:100-110.
179. Sparks D.L. Environmental Soil Chemistry 1995, 81-90. Academic Press, San Diego.
180. Stafford H.A. Flavonoid Metabolism 1990, 298. CRC Press, Boca Raton, FL.
181. Stein W.J., Wand S.J.E., Holcroft D.M., Jacobs G. Anthocyanins in vegetative tissues: A proposed unified function in photoprotection. New Phytol. 2002, 155:349-361.
182. Steinkellner S., Lendzemo V., Langer I., Schweiger P., Khaosaad T., Toussaint J.P., Vierheilig H. Flavonoids and strigolactones in root exudates as signals in symbiotic and pathogenic plant-fungus interactions. Molecules 2007, 12:1290-1306.
183. Svoboda J.A., Weirich G.F. Sterol metabolism in the tobacco hornworm, Manduca sexta. Lipids 1995, 30:263-267.
184. Tarr J.B., Arditti J. Niacin biosynthesis in seedlings of Zea mays. Plant Physiol. 1982, 69:553-556.
185. Tolonen A., Uusitalo J. Fast screening method for the analysis of total flavonoid content in plants and foodstuffs by high-performance liquid chromatography/electrospray ionization time-of-flight mass spectrometry with polarity switching. Rapid Commun. Mass Spectrom. 2004, 18:3113-3122.
186. Turiel E., Martín-Esteban A., Tadeo J.L. Multiresidue analysis of quinolones and fluoroquinolones in soil by ultrasonic-assisted extraction in small columns and HPLC-UV. Anal. Chim. Acta 2006, 562:30-35.
187. Turlings T.C.J., Tumlinson J.H., Lewis W.J. Exploitation of herbivore-induced plant odors by host-seeking parasitic wasps. Science 1990, 250:1251-1253.
188. Turlings T.C.J., McCall P.J., Alborn H.T., Tumlinson J.H. An elicitor in caterpillar oral secretions that induces corn seedlings to emit chemical signals attractive to parasitic wasps. J. Chem. Ecol. 1993, 19:411-425.
189. Uren N.C. Types, amounts, and possible functions of compounds released into the rhizosphere by soil-grown plants. The Rhizosphere 2001, 19-40. Marcel Dekker Inc., New York. R. Pinton, Z. Varanini, P. Nannipieri (Eds.).
190. Vairavamurthy A., Wang S. Organic nitrogen in geomacromolecules: insights on speciation and transformation with Kedge XANES spectroscopy. Environ. Sci. Technol. 2002, 36:3050-3057.
191. VanCura V., Hovadik A. Composition of root exudates in the course of plant development. Plant Microbes Relationships 1965, 21-25. Czechoslovakia Academy of Sciences, Prague. J. Macura, V. VanCura (Eds.).
192. Van der Kaaden A., Boon J.J., de Leeuw J.W., Lange F., Schuyl P.J.W., Schulten H.-R., Bahr U. Comparison of analytical pyrolysis techniques in the characterization of chitin. Anal. Chem. 1984, 56:2160-2165.
193. Van Onckelen H., Prinsen E., Inzc D., Riidelsheim R., Van Lijsebettens M., Follin A., Schell J., Van Montagu M., De Greef J. Agrobacterium T-DNA gene 1 codes for tryptophan 2monooxygenase activity in tobacco crown gall cells. FEBS Lett. 1986, 198:357-360.
194. Veldstra H. Considerations on the interaction of ergons and their 'substrates'. Biochim. Biophys. Acta 1947, 1:364-378.
195. Vivanco J.M., Guimarães R.L., Flores H. Underground plant metabolism: The biosynthetic potential of roots. Plant Roots: The Hidden Half 2002, 1573-1608. Marcel Dekker Inc., New York, Chapter 58. Y. Waisel, A. Eshel, U. Kafkaki (Eds.).
196. Von Wettstein D., Gough S., Kannangara C.G. Chlorophyll biosynthesis. Plant Cell 1995, 7:1039-1057.
197. Wagner R., Czerny M., Bielohradsky J., Grosch W. Structure-odour-activity relationships of alkylpyrazines. Z. Lebensm. Unters Forsch. A 1999, 208:308-316.
198. Walsh C.T., Garneau-Tsodikova S., Howard-Jones A.R. Biological formation of pyrroles: Nature's logic and enzymatic machinery. Nat. Prod. Rep. 2006, 23:517-531.
199. Wang X., Kolattukudy P.E. Solubilization and purification of aldehyde generating fatty acid acyl-CoA reductase from green algae Botryococcus braunii. FEBS Lett. 1995, 370:15-18.
200. Weete J.D. Sterols of the fungi: Distribution and biosynthesis. Phytochemistry 1973, 12:1843-1864.
201. Wentzel A., Ellingsen T.E., Kotlar H.K., Zotchev S.B., Throne-Holst M. Bacterial metabolism of longchain n-alkanes. Appl. Microbiol. Biotechnol. 2007, 76:1209-1221.
202. Weston L.A., Ryan P.R., Watt M. Mechanisms for cellular transport and release of allelochemicals from plant roots into the rhizosphere. J. Exp. Bot. 2012, 63:3445-3454.
203. White D.C., Stair J.O., Ringelberg D.B. Quantitative comparisons of in situ microbial biodiversity by signature biomarker analysis. J. Ind. Microbiol. 1997, 17:185-196.
204. Willemot C., Hope H.J., Williams R.J., Michaud R. Changes in fatty acid composition of winter wheat during frost hardening. Cryobiology 1977, 14:87-93.
205. Winkel-Shirley B. Biosynthesis of flavonoids and effects of stress. Curr. Opin. Plant Biol. 2002, 5:218-223.
206. Yang K.S., Waller G.R. Biosynthesis of the pyridine ring of ricinine from quinolinic acid glycerol and aspartic acid. Phytochemistry 1965, 4:881-889.
207. Yang X.E., Bligar V.C., Foster J.C., Martens D.C. Accumulation and transport of nickel in relation to organic acids in ryegrass and maize grown with different nickel levels. Plant Soil 1997, 196:271-276.
208. Yoneyama K., Xie X., Yoneyama K., Takeuchi Y. Strigolactones: Structures and biological activities. Pest Manag. Sci. 2009, 65:467-470.
209. Zhang Y.-M., White S.W., Rock C.O. Inhibiting bacterial fatty acid synthesis. J. Biol. Chem. 2006, 281:17541-17544.