Abstract
Micro-organisms have been amongst the organisms of choice, both for the study of the oxidative catabolism of aromatic compounds, and in the elucidation of the biogenesis of benzene nuclei. The salient features of the biochemistry of these two processes have now become clearer, mainly as a result of work carried out during the past decade. It transpires that there is apparently no close connection between them; the degradative pathways of aromatic-ring fission are entirely different from those employed by micro-organisms in their biosyntheses.
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Literature
Ames, B.W., and H.K. Mitchell: The biosynthesis of histidine. J. of Biol. Chem. 212, 687–696 (1955).
Arnow, L. E.: The formation of dopa by the exposure of tyrosine solutions to ultra-violet radiations. J. of Biol. Chem. 120, 151–153 (1937).
Destruction of phenylalanine by ultraviolet radiant energy. Proc. Soc. Exper. Biol. a. Med. 49, 578-579 (1942).
Audits, L. J.: A new soil perfusion apparatus. Nature (Lond.) 158, 419 (1946).
Biological detoxication of 2:4-dichlorophenoxyacetic acid in soils; isolation of an effective organism. Nature (Lond.) 166, 356 (1950).
The biological detoxication of hormone herbicides in soil. Plant a. Soil 3, 170-192 (1951).
The decomposition of 2:4-dichlorophenoxy-acetic acid and 2-methyl-4-chlorophenoxyacetic acid in the soil. J. Sci. Food Agricult. 3, 268-274 (1952).
Audtts, L. J., and K. V. Symonds: Further studies on the breakdown of 2:4-dichlorophenoxyacetic acid by a soil bacterium. Ann. Appl. Biol. 42, 174–182 (1955).
Beadle, G. W., H.K. Mitchell and J. F. Nyc: Kynurenine as intermediate in the formation of nicotinic acid from tryptophan by Neurospora. Proc. Nat. Acad. Sci. U.S.A. 33, 155–158 (1947).
Beadle, G. W., and E. L. Tatttm: Genetic control of biochemical reactions in Neurospora. Proc. Nat. Acad. Sci. U.S.A. 27, 499–506 (1941).
Bell, G. R.: On the photochemical degradation of 2:4-d and structurally related compounds in the presence and absence of riboflavin. Bot. Gaz. 118, 133–136 (1956).
Beijerinck, M. W.: Verzamelde Geschriften, Delft 1–6 (1921-1940).
Bergey, D.H.: Manual of Determinative Bacteriology. (Arranged by a Committee of the Society of American Bacteriologists), 6th Ed. Baltimore: Williams & Wilkins Co. 1948.
Bernhard, K., u. E. Gressly: Zur Oxydation des Benzolrings im Tierkörper. Helvet. chim. Acta 24, 83–87 (1941).
Bernheim, F.: The oxidation of benzoic acid and related substances by certain Mycobacteria. J. of Biol. Chem. 143, 383–389 (1942).
The effect of substituted benzoic acids on adaptive enzyme formation in a Mycobacterium. J. of Biol. Chem. 203, 775-780 (1953).
Birch, A. J., and F. W. Donovan: Studies in relation to biosynthesis. Austral. J. Chem. 6, Parts 1, 2, 3, 360–378 (1953).
Birch, A. J., F. W. Donovan and F. Moewus: Biogenesis of flavonoids in Chlamydomonas eugametos. Nature (Lond.) 172, 902–904 (1953).
Birch, A. J., R. A. Massy-Westropp and C.J. Moye: Studies in relation to biosynthesis. VII. 2-Hydroxy-6-methylbenzoic acid in Penicillium griseofulvum Dierckx. Austral. J. Chem. 8, 539–544 (1955).
Birch, A. J., R. A. Massy-Westropp, R. W. Rickards and Herchel Smith: The conversion of acetic acid into griseofulvin in Penicillium griseofulvum Dierckx. Proc. Chem. Soc. 1957, 98.
Birch, A. J., and C. J. Moye: Studies in relation to biosynthesis. Part X. A synthesis of lumichrome from non-benzenoid precursors. J. Chem. Soc. (Lond.) 1957, 412-414.
Bloom, B. M., and G. M. Shull: Epoxidation of unsaturated steroids by micro-organisms. J. Amer. Chem. Soc. 77, 5767 (1955). [See also S. H. Eppstein, P. D. Meister, H. C. Murray and D. H. Peterson, Microbiological transformations of steroids and their applications to the synthesis of hormones. Vitamins a. Hormones 14, 359-432 (1956), ed. by R. S. Harris, G. F. Marrian and K. V. Thimann. New York: Academic Press, Inc.].
Boeseken, J., u. R. Engelberts: Formation of cis-cis-muconic acid and phenoquinone in the oxidation of phenol with peracetic acid. Proc. Acad. Sci. Amsterdam 34, 1292 (1931).
Boeseken, J., and C.F. Metz: L’oxydation de quelques phenols par l’acide peracetique. Un passage de la série aromatique à la serie aliphatique. Rec. Trav. chim. Pays-Bas (Amsterd.) 54, 345–352 (1935).
Bourquelot, E. E., et G. Bertrand: La laccase dans les champignons. C. r. Soc. Biol. Paris 121, 783–786 (1895).
Boyland, E.: The biological significance of metabolism of polycyclic hydrocarbons. Biochem. Soc. Symposia 1950, No 5, 40–54.
Brown, E. G., T. W. Goodwin and S. Pendlington: Studies on the biosynthesis of riboflavin metabolism and flavinogenesis in Eremothecium ashbyii. Biochemie. J. 61, 37–46 (1955).
Brown, J.P., and E. B. McCall: Some chlorinated hydroxy-phenoxyacetic acids. J. Chem. Soc. (Lond.) 1955, 3681-3687.
Buswell, A. M.: Chemistry of water and sewage treatment. Amer. Chem. Soc, Monogr. Ser. No 38, Chem. Catalogue 1928.
Buswell, A.M., and C. S. Boruff: The relation between the chemical composition of organic matter and the quality and quantity of gas produced during sludge digestion. Sewage Works J. 4, 454–460 (1932).
Fermentation products from cornstalks. Ind. Eng. Chem. 22, 931 (1930).
The anaerobic fermentation of lignin. J. Amer. Chem. Soc. 56, 886-888, 1751 (1934).
Cavill, G. W. K., and D. L. Ford: The chemistry of plant growth regulators, Part 1. 2:4-Dichloro-6-hydroxyphenoxyacetic acid and related compounds. J. Chem. Soc. (Lond.) 1954, 565-568.
Cohn, M., J. Monod, M. R. Pollock, S. Spiegelman and R. Y. Stanier: Terminology of enzyme formation. Nature (Lond.) 172, 1096 (1953).
Collie, J. N.: Derivatives of the multiple keton group. J. Chem. Soc. (Lond.) 1907, 1806-1813.
Collins, F. M., and C. M. Sims: A compact soil perfusion apparatus. Nature (Lond.) 178, 1073 (1956).
Coulson, C.B., and W.C. Evans: Unpublished observations 1957.
Czekalowski, J. W., and B. Szkarzynski: The breakdown of phenols and related compounds by bacteria. J. Gen. Microbiol. 2, 231–238 (1948).
Dagley, S., Mona E. Fewster and F. C. Happold: The bacterial oxidation of aromatic compounds. J. Gen. Microbiol. 8, 1–7 (1953).
Dagley, S., and M. D. Patel: Oxidation of ρ-cresol and related compounds by a Pseudomonas. Biochemie. J. 66, 227–233 (1957).
Dalgliesh, C. E.: Nonspecific formation of hydroxylated metabolites of the aromatic amino acids. Arch. of Biochem. a. Biophysics 58, 214–226 (1955).
Davis, B. D.: The isolation of biochemically deficient mutants of bacteria by means of penicillin. Proc. Nat. Acad. Sci. U.S.A. 35, 1–10 (1949).
Nutritionally deficient bacterial mutants isolated by means of penicillin. Experientia (Basel) 6, 41-50 (1950).
Aromatic biosynthesis. 1. The rôle of shikimic acid. J. of Biol. Chem. 191, 315-325 (1951).
Intermediates in the biosynthesis of amino-acids. Symposium sur le métabolisme microbien. II. Congr. Internat. de Biochemie, p. 32-40, 1952.
Aromatic biosynthesis. Preferential conversion in incompletely blocked mutants of a common precursor of several metabolites. J. Bacter. 64, 729-748 (1952).
Biosynthesis of the aromatic amino-acids. Symposium on Amino Acid Metabolism, edit. W. D. McEleoy and B. Glass. Baltimore: Johns Hopkins Press 1955.
Perspectives and Horizons in Microbiology, edit. by S. A. Waksman. New Brunswick: Rutgers Univ. Press 1955.
Some aspects of amino-acid biosynthesis in micro-organisms. Federat. Proc. 14, 691-695 (1955).
Intermediates in amino-acid biosynthesis. Adv. Enzymol. 16, 247-312 (1955).
Davis, B. D., C. Gilvarg and S. Mitsuhashi: Enzymes of aromatic biosynthesis. In Methods of Enzymology, edit, by S. P. Colowick and N. P. Kaplan, vol. 2, p. 300–311. New York: Academic Press 1955.
Davis, B. D., and Elizabeth S. Mingioli: Aromatic biosynthesis. VII. Accumulation of two derivatives of shikimic acid by bacterial mutants. J. Bacter. 66, 129–136 (1953).
Dooren de Jong, L. E. den: Bijdrage tot de kennis van het mineralisatieproces. Thesis, Delft 1926.
Drummond, Sir J. C., and I. L. Finar: Muconic acid as a metabolic product of benzene. Biochemic. J. 32, 79–84 (1938).
Eadie, G. S., F. Bernheim and R.J. Fitzgerald: The kinetics of the oxidation of benzoic acid by certain Mycobacteria. J. of Biol. Chem. 176, 857–862 (1948).
Ehrensvard, G.: On the origin of aromatic structures. Symposium sur le métabolisme microbien. II. Congr. Internat. de Biochemie, p. 72-85. 1952.
Ehrensvärd, G., L. Reio, E. Saluste and R. Stjernholm: Acetic acid metabolism in Torulopsis utilis. J. of Biol. Chem. 189, 93–108 (1951).
Eisner, Ulli, J. A. Elvidge and R. P. Linstead: Unsaturated lactones and related substances. Part V. Dihydro-ß-ketomuconic acid, and carboxylactones of the protoanemonin type. J. Chem. Soc. (Lond.) 1951, 1501-1512.
Elvidge, J. A., R. P. Linstead, P. Sims and B. A. Orkin: The third isomeric (cis-trans-) muconic acid. J. Chem. Soc. (Lond.) 1950, 2235-2241.
Erikson, D.: Studies on some lake-mud strains of Micromonospora. J. Bacter. 41, 277–300 (1941).
Evans, R. A., W. H. Parr and W. C. Evans: Chromatography of phenols. Nature (Lond.) 164, 674 (1949).
Evans, W. C.: Oxidation of phenol and benzoic acid by some soil bacteria. Biochemic. J. 41, 373–382 (1947).
The early intermediate formed in the oxidative metabolism of phthalic acid by certain soil bacteria. Biochemie. J. 61, x (1955).
Biochemistry of the oxidative metabolism of aromatic compounds by micro-organisms. Annual Rep. Chem. Soc. (Lond.) 53, 279-294 (1956).
Evans, W. C., and H. N. Fernley: Unpublished observations 1957.
Evans, W. C., and F. C. Happold: The utilization of phenol by bacteria. J. Soc. Chem. Industr. 58, 55 (1939).
Evans, W. C., and P. Moss: The metabolism of the herbicide ρ-chlorophenoxy-acetic acid by a soil micro-organism-isolation of a β-chloromuconic acid on ring fission. Biochemie. J. 65, 8p (1957).
Evans, W. C., and B. S. W. Smith: The oxidation of aromatic compounds by soil bacteria. Biochemie. J. 49, x (1951).
The photochemical in-activation and microbial metabolism of the chlorophenoxyacetic acid herbicides. Biochemie. J. 57, xxx (1954).
Evans, W. C., B. S. W. Smith, R. P. Linstead and J. A. Elvidge: Chemistry of the oxidative metabolism of certain aromatic compounds by micro-organisms. Nature (Lond.) 168, 772–775 (1951).
Fahreus, G.: On the oxidation of phenolic compounds by wood-rotting fungi. Kgl. Lantbrukgs-Hogskol. Ann. 16, 618–629 (1939).
Fawcett, C. H., J. M. A. Ingram and R. L. Wain: β-Oxidation of ω-phenoxyalkylcarboxylic acids in the flax plant. Nature (Lond.) 170, 887–888 (1952).
Feigl, F.: Spot Tests, Vol. 2: Organic Applications. London: Elsevier Publ. Co. 1954.
Fildes, Sir P.: Indole as a precursor in the synthesis of trypto-phan by bacteria. Brit. J. Exper. Path. 21, 315–319 (1940).
Fischer, H. F., E. E. Conn, B. Vennesland and F. H. Westheimer: The enzymatic transfer of hydrogen. J. of Biol. Chem. 202, 687–697 (1953).
Fischer, H. O. L., u. G. Dangschat: Übergang der Chinasäure in Shikimisäure. Naturwiss. 26, 562–563 (1938).
Fitzgerald, R. J., F. Bernheim and Dorothea B. Fitzgerald: The inhibition by streptomycin of adaptive enzyme formation in Mycobacteria. J. of Biol. Chem. 175, 195–200 (1948).
Fowler, G. J., E. Ardern and W. T. Lockett: The oxidation of phenol by certain bacteria in pure culture. Proc. Roy. Soc. Lond., Ser. B 83, 149–156 (1911).
Geissman, T. A., and J. B. Harborne: The chemistry of flower pigmentation in Antirrhinum maw. Arch, of Biochem. a. Biophysics 55, 447–454 (1955).
Geissman, T. A., and T. Swain: Biosynthesis of flavonoid compounds in higher plants. Chem. a. Ind. 1957, 984.
Ghosh, J. J., E. Adams and B.D. Davis: Tyrosine biosynthesis in E.coli; conversion of prephenic acid (PPA) to ρ-hydroxyphenyllactic acid (HPL). Federat. Proc. 15, 261 (1956).
Gilvarg, C., and K. Bloch: Synthesis of phenylalanine and tyrosine in yeast. J. Amer. Chem. Soc. 72, 5791–5792 (1950).
Federat. Proc. 10, 189 (1951).
Gordon, J., and J. W. McLeod: Quoted by F. C. Happold in: A system of Bacteriology in Relation to Medicine, Vol. 9, p. 163. 1931. Medical Research Council, Pub. H. M. S. O.
Gordon, M. F. A. Haskins and H.K. Mitchell: The growth promoting properties of quinic acid. Proc. Nat. Acad. Sci. U.S.A. 36, 427–430 (1950).
Gottlieb, S., and M. Pelczar Microbial aspects of lignin degradation. Bacter. Rev. 15, 55–76 (1951).
Gray, P. H. H., and H. G. Thornton: Soil bacteria that decompose certain aromatic compounds. Zbl. Bakter., 2. Abt. 73, 74–96 (1928).
Gross, S. R., R.D. Gafford and E.L. Tatum: The metabolism of protocatechuic acid by Neurospora crassa. J. of Biol. Chem. 219, 781–796 (1956).
Gross, S. R., and E. L. Tatum: Structural specificity of inducers of protocatechuic acid oxidase synthesis in Neurospora. Science (Lancaster, Pa.) 122, 1141 (1955).
Gunsalus, I. C., G.F. Gunsalus and R.Y. Stanier: The enzymatic conversion of mandelic acid to benzoic acid. J. Bacter. 66, Parts 1, 2, 3, 4, 538–553 (1953).
Gunter, Shirley E.: The enzymatic oxidation of ρ-hydroxymandelic acid to ρ-hydroxybenzoic acid. J. Bacter. 66, 341–346 (1953).
Hansen, J. R., and K. P. Buchholtz: Inactivation of 2:4-d by riboflavin in light. Weeds (J. Assoc. Reg. Weed Control Con.) 1, 237–242 (1952).
Happold, F. C: The correlation of the oxidation of certain phenols and of dimethyl-ρ-phenylenediamine by bacterial suspensions. Biochemic. J. 24, 1737–1743 (1930).
The oxidation of aromatic rings by micro-organisms in metabolism. Biochem. Soc. Symposia 1950, No 5, 85-96.
Happold, F. C., and A. Key: The bacterial purification of gasworks’ liquors. The action of the liquors on the bacterial flora of sewage. J. of Hyg. 32, 573–580 (1932).
Haskins, F. A., and H.K. Mitchell: Evidence for a tryptophan cycle in Neurospora. Proc. Nat. Acad. Sci. U.S.A. 35, 500–506 (1949).
Hayaishi, O., and Z. Hashimoto: Pyrocatechase. A new enzyme catalyzing the breakdown of pyrocatechin. Med. J. Osaka Univ. 2, 33–36 (1950).
Hayaishi, O., M. Katagiri and S. Rothberg: Mechanism of the pyrocatechase reaction. J. Amer. Chem. Soc. 77, 5450–5451 (1955).
Hayaishi, O., and R. Y. Stanier: The bacterial oxidation of tryptophan. Enzymatic activities of cell-free extracts from bacteria employing the aromatic pathway. J. Bacter. 62, 691–709 (1951).
The kynureninase of Pseudomonas fluorescens. J. of Biol. Chem. 195, 735-740 (1952).
Hayano, M., M. Lindberg, R. Dorfman, J. Hancock and W. Doeting: On the mechanism of the C-11-β-hydroxy-lation of steroids; a study with H2 18O and 18O2. Arch, of Biochem. a. Biophysics 59, 529–531 (1955).
Henderson, L. M.: Quinolinic acid metabolism. 1. J. of Biol. Chem. 178, 1005–1006 (1949).
Quinolinic acid metabolism. 2. Replacement of nicotinic acid for the growth of the rat and Neurospora. J. of Biol. Chem. 181, 677-685 (1949).
Henderson, Moira E. K., and V. C. Farmer: Utilization by soil fungi of ρ-hydroxybenzaldehyde, ferulic acid, syringaldehyde, and vanillin. J. Gen. Microbiol. 12, 37–46 (1955).
Hockenhtjll, D. J. D., A. D. Walker, G. D. Wilkin and F. G. Winder: Oxidation of phenylacetic acid by Penicillium chrysogenum. Biochemie. J. 50, 605–609 (1952).
Hopkins, Sir F. G., and S.W. Cole: Constitution of tryptophan. J. of Physiol. 29, 451–466 (1903).
Horecker, B. L., P. Z. Smyrniotis, H. H. Hiatt and P.A. Marks: Tetrose phosphate and the formation of sedoheptulose-diphosphate. J. of Biol. Chem. 212, 827–836 (1955).
Hughes, D. E.: A press for disrupting bacteria and other micro-organisms. Brit. J. Exper. Path. 32, 97–109 (1951).
6-Hydroxynicotinic acid as an intermediate in the oxidation of nicotinic acid by Pseudomonas fluorescens. Biochem. et Biophysica Acta 9, 226-227 (1952).
Hunt, A. L., D. E. Hughes and J. M. Lowenstein: The hydroxylation of nicotinic acid by Pseudomonas fluorescens. Biochemie. J. 66, 2P (1957).
Isono, M.: Oxidative metabolism of phenylacetic acid by Penicillium chrysogenum. J. Agricult. Chem. Soc. Japan 27, Parts 1–4, 193–301 (1953); 28, Parts 5–6, 196-205 (1954).
Jacobs, S. E.: The influence of antiseptics on the bacterial and protozoan population of greenhouse soils. I. Naphthalene. Ann. Appl. Biol. 18, 98–136 (1931).
Jaffe, M.: Über die Aufspaltung des Benzolrings im Organismus. Z. physiol. Chem. 62, 58–67 (1909).
Jakoby, W., and D. M. Bonner: Kynureninase from Neurospora: purification and properties. J. of Biol. Chem. 205, 699–707 (1953).
Jakoby, W., and D. M. Bonner: Kynureninase from Neurospora: interaction of enzyme with substrates, coenzyme, and amines. J. of Biol. Chem. 205, 709–715 (1953).
Jensen, H. L., and K. Gundersen: Biological decomposition of aromatic nitro-compounds. Nature (Lond.) 175, 341 (1955).
Acta agricult. scand. (Stockh.) 6, 100-114 (1956).
Jensen, H. L., and H. I. Petersen: Decomposition of hormone herbicides by bacteria. Acta agricult. scand. (Stockh.) 2, 215–231 (1952).
Jones, J. D., B. S. W. Smith and W. C. Evans: Homogentisic acid an intermediate in the metabolism of tyrosine by the aromatic ring-splitting micro-organisms. Biochemie. J. 51, xi (1952).
Kalan, E. B., B. D. Davis, P. R. Srinivasan and D. B. Sprinson: The conversion of various carbohydrates to 5-dehydro-shikimic acid by bacterial extracts. J. of Biol. Chem. 223, 907–912 (1956).
Kalan, E. B., and P. R. Srinivasan: Synthesis of 5-dehydro-shikimic acid from carbohydrates in a cell-free extract. Symposium on Amino Acid Metabolism, edit. by W. D. McElroy and B. Glass, p. 826–830. Baltimore: Johns Hopkins Press 1955.
Karlsson, J. L., and H. A. Barker: Evidence against the occurrence of a tricarboxylic acid cycle in Azotobacter agilis. J. of Biol. Chem. 175, 913–921 (1948).
Karstrom, H.: Enzymatische Adaptation bei Mikroorganismen. Erg. Enzymforsch. 7, 350–376 (1937/38). See also: Adaptation in Micro-organisms, Third Symp. Soc. Gen. Microbiol., edit. by E. F. Gale and E. Davis, Cambridge, Eng.: Cambridge Univ. Press 1953 and The Microbe’s Contribution to Biology by A. J. Kluyver, and C.B. van Niel. Cambridge, Mass.: Harvard Univ. Press 1956.
Katagiri, M., and O. Hayaishi: Enzymatic degradation of β-ketoadipic acid. J. of Biol. Chem. 226, 439–448 (1957).
Katagiri, M., and R. Sato: Accumulation of phenylalanine by a phenylalanine mutant of Escherichia coli. Science (Lancaster, Pa.) 118, 250 (1953).
Kilby, B. A.: The formation of β-ketoadipic acid by bacterial fission of aromatic rings. Biochemic. J. 43, v (1948); 49, 671–677 (1951).
Kluyver, A. J.: The Chemical Activities of Micro-organisms. London: Univ. Press 1931.
Kluyver. A. J., and J. C. M. van Zijp: The production of homogentisic acid out of phenylacetic acid by Aspergillus niger. Antonie van Leeuwenhoek J. Microbiol. Serol. 17, 315–324 (1951).
Knox, W. E.: A Symposium on Amino Acid Metabolism. Edit, by W. D. McElroy and B. Glass. Baltimore: Johns Hopkins Press 1955.
Methods in Enzymology. Edit. by S. P. Colowick and N.O. Kaplan, vol. 2. New York: Academic Press 1955.
Kubowitz, F.: Über die chemische Zusammensetzung der Kartoffeloxydase. Biochem. Z. 292, 221–229 (1937).
Landa, S., and J. Eliasek: Biological degradation of phenols. Chem. Listy 47, 622–629, 1066-1070 (1953); 50, 1834-1839 (1956).
Lederberg, J., and N. Zinder: Isolation of biochemically deficient mutants of bacteria by penicillin. J. Amer. Chem. Soc. 70, 4267–4268 (1948).
Lees, H., and J. H. Quastel: A new technique for the study of soil sterilization. Chem. a. Ind. 1944, 238-239.
Loew, O.: Über das Verhalten der Chinasäure zu den Spaltpilzen. Ber. chem. Ges. 14, 450–452 (1881).
MacDonald, D. L., R. Y. Stanier and J. L. Ingraham: The enzymatic formation of β-carboxymuconic acid. J. of Biol. Chem. 210, 809–820 (1954).
Martinon: Action of hydrogen peroxide on the phenols. Bull. Soc. Chim. 2, 43, 155–158 (1885).
Mason, H. S.: Comparative biochemistry of the phenolase complex. Adv. Enzymol. 16, 105–184 (1955).
Mason, H. S., I. Onopryenko and D. Buhler: Hydroxylation: the activation of oxygen by peroxidase. Biochim. et Biophysica Acta 24, 225 (1957).
Mehler, A. H.: A Symposium on Amino Acid Metabolism, edit. by W. D. McElroy and B. Glass, p. 882–908. Baltimore: Johns Hopkins Press 1955.
Miller, L. P.: Induced formation of ß-gentiobiosides in gladiolus corms and tomato plants treated with chemicals. Science (Lancaster, Pa.) 92, 42–43 (1940).
Mitoma, C., and L. C. Leeper: Enzymatic conversion of phenylalanine to tyrosine. Federat. Proc. 13, 266 (1954).
Mitoma, C., H. S. Posner, H. C. Reitz and S. Udenfriend: Enzymatic hydroxylation of aromatic compounds. Arch. of Biochem. a. Biophysics 61, 431–441 (1956).
Mitsuhashi, S., and B. D. Davis: Aromatic biosynthesis. XII. Conversion of 5-dehydroquinic acid to 5-dehydroshikimic acid by 5-dehydroquinase. Biochim. et Biophysica Acta 15, 54–61 (1954).
Aromatic biosynthesis. XIII. Conversion of quinic acid to 5-dehydroquinic acid by quinic dehydrogenase. Biochim. et Biophysica Acta 15, 268-280 (1954).
Moore, F. W.: The utilization of pyridine by micro-organisms. J. Gen. Microbiol. 3, 143–146 (1949).
Murphy, J. F., and R. W. Stone: The bacterial dissimilation of naphthalene. Canad. J. Microbiol. 1, 579–588 (1954/55).
Neunhoeffer, O.: Über Ringsprengung an o-Mtrophenolen durch Schwefelsäure. Ber. chem. Ges. 68, 1774–1781 (1935).
Nord, F.F., W.J. Schubert and S. N. Acerbo: On the mechanism of lignification. Naturwiss. 2, 35–36 (1957).
Nyc, J. F., H. K. Mitchell, E. Liefer and W. H. Langham: The use of isotopic carbon in a study of the metabolism of anthranilic acid in Neurospora. J. of Biol. Chem. 179, 783–787 (1949).
Ogston, A. G.: Interpretations of experiments on metabolic processes using isotopic tracer elements. Nature (Lond.) 162, 963 (1948).
Parke, D. V., and R.T. Williams: The metabolism of benzene. The muconic acid excreted by rabbits receiving benzene. Determination of the isomeric muconic acids. Biochemie. J. 51, 339–348 (1952).
Parr, W. H., R. A. Evans and W. C. Evans: The mechanism of the bacterial oxidation of certain aromatic compounds, together with the preparation of a cell-free enzyme system which accomplishes ring-cleavage. Biochemie. J. 45, xxix (1949).
Partridge, C. W. H., D.M. Bonner and C. Yanofsky: A quantitative study of the relationship between tryptophan and niacin in Neurospora. J. of Biol. Chem. 194, 269–278 (1952).
Perrier, A.: Fermentation of compounds of the cyclic series and the formation of humus substances. Ann. Sci. Agronom. (4) 30, 321–350 (1913).
Plaut, G. W. E.: Biosynthesis of riboflavin. J. of Biol. Chem. 211, 111–116 (1954).
Potter, V. R., and C. Heidelberger: Biosynthesis of “asymmetric” citric acid; a substantiation of the Ogston concept. Nature (Lond.) 164, 180–181 (1949).
Raper, H. S.: The aerobic oxidases. Physiologic. Rev. 8, 245–282 (1928).
Note on the oxidation of tyrosine, tyramine, and phenylalanine with hydrogen peroxide. Biochemie. J. 26, 2000-2004 (1932).
Rhuland, L. E., and R. C. Bard: The rôle of anthranilic acid in the nutrition of Lactobacillus arabinosus. J. Bacter. 63, 133–143 (1952).
Robinson, Sir R.: The Structural Relations of Natural Products. Oxford: Clarendon Press 1955.
Rogoff, M. H., and J. J. Reid: Bacterial decomposition of 2:4-d. J. Bacter. 71, 303–307 (1956).
Rogoff, M. H., and I. Wender: The microbiology of coal. I. Bacterial oxidation of phenanthrene. J. Bacter. 73, 264 (1957).
3-Hydroxy-2-naphthoic acid as an intermediate in bacterial dissimilation of anthracene. J. Bacter. 74, 108 (1957).
Roof, Betty S., Theodora J. Lannon and J. C. Turner: Bacterial oxidation of salicylic acid and related antirheumatic phenolic acids. Proc. Soc. Exper. Biol. a. Med. 84, 38–41 (1953).
Salamon, I.I., and B.D. Davis: Aromatic biosynthesis. IX. The isolation of a precursor of shikimic acid. J. Amer. Chem. Soc. 75, 5567–5571 (1953).
Saunders, B. H.: Peroxidase. Action and uses in organic synthesis. Roy. Inst. Chem. Monogr. 1957, No 1, 1–27.
Schubert, W. J., and F.F. Nord: Lignification. Adv. Enzymol. 18, 349–378 (1957).
Schultze, W. H.: A new method of testing the reducing and oxidizing power of bacteria. Zbl. Bakter., 1. Abt. 56, 544–545 (1910).
Shigettra, H. T., and D. B. Sprinson: Biosynthesis of shikimic acid from labelled compounds. Federat. Proc. 11, 286 (1952).
Simmonds, S.: The metabolism of phenylalanine and tyrosine in mutant strains of Escherichia coli. J. of Biol. Chem. 185, 755–762 (1950).
Simpson, J. R.: M. Sc. Thesis, Univ. of Wales 1954.
Simpson, J. R., and W.C. Evans: The metabolism of nitrophenols by certain bacteria. Biochemic. J. 55, xxiv (1953).
Sistrom, W. R., and R. Y. Stanier: The mechanism of formation of β-ketoadipic acid by bacteria. J. of Biol. Chem. 210, 821–836 (1954).
Enzymatic conversion of two geometrical isomers into enantiomorphs. Nature (Lond.) 174, 513-514 (1954).
Sleeper, B. P.: The bacterial oxidation of aromatic compounds. Metabolism of benzoic acid labelled with 14C. J. Bacter. 62, 657–662 (1951).
Sleeper, B. P., and R. Y. Stanier: The bacterial oxidation of aromatic compounds. 1. Adaptive patterns with respect to polyphenolic compounds. J. Bacter. 59, 117–127 (1950).
Smith, B. S. W.: Ph.D. Thesis, Univ. of Wales 1954.
Smith, B. S. W., J.D. Jones and W. C. Evans: Aromatic oxidative metabolism of certain benzene ring compounds by soil bacteria. Biochemie. J. 50, xxviii (1952).
Snell, E. E.: Growth promotion on trypto-phan-deficient media by o-aminobenzoic acid and its attempted reversal with orthoanilamide. Arch, of Biochem. 2, 389–394 (1943).
Sohngen, N. L.: Het onstaan en verdwijnen van waterstof en methaan onder den invloed van het organische leven. Thesis, Delft 1906.
Spiegelman, S., and A.M. Campbell: The significance of induced enzyme formation. In: Currents in Biochemical Research, edit. D.E. Green, p. 115–161. New York: Inter-science Pub. Inc. 1956.
Sprinson, D. B.: The rôle of carbohydrates in the biosynthesis of aromatic compounds. In: Essays in Biochemistry, p. 259–269, edit. S. Graff. New York: J. Wiley & Sons, Inc. 1956.
Srinivasan, P. R., H. T. Shigeura, M. Sprecher, D. B. Sprinson and B. D. Davis: The biosynthesis of shikimic acid from d-glucose. J. of Biol. Chem. 220, 477–497 (1956).
Srinivasan, P. R., D. B. Sprinson, E. B. Kalan and B. D. Davis: The enzymatic conversion of sedoheptulose-1:7-diphosphate to shikimic acid. J. of Biol. Chem. 223, 913–920 (1956).
Stanier, R. Y.: Simultaneous adaptation. A new technique for the study of metabolic pathways. J. Bacter. 54, 339–348 (1947).
The oxidation of aromatic compounds by fluorescent Pseudomonas. J. Bacter. 55, 477-494 (1948).
Problems of bacterial oxidative metabolism. Bacter. Rev. 14, 179-197 (1950).
The bacterial oxidation of aromatic compounds. Symposium sur le métabolisme microbien: II. Congr. Internat. de Biochemie, p. 64-71. 1952.
Aspects of synthesis and order in growth. (3) The plasticity of enzymatic patterns in microbial cells, edit. by Dorothea Rudnick, p. 43-67. Princeton, New Jersey: Princeton Univ. Press 1955.
Cleavage of aromatic rings with eventual formation of β-ketoadipic acid. In: Methods in Enzymology, vol. 2, p. 273-287; vol. 3, p. 614-620, edit. by S. P. Colowick and N. O. Kaplan. New York: Academic Press Inc. 1955, 1957.
Stanier, R. Y., and O. Hayaishi: The bacterial oxidation of trypto-phan: a study in comparative biochemistry. Science (Lancaster, Pa.) 114, 326–330 (1951).
Stanier, R. Y., O. Hayaishi and Martha Tsuchida: The bacterial oxidation of tryptophan. A general survey of the pathways. J. Bacter. 62, 355–366 (1951).
Stanier, R. Y., and J. L. Ingraham: Protocatechuic acid oxidase. J. of Biol. Chem. 210, 799–808 (1954).
Stanier, R. Y., and Martha Tsuchida: Adaptive enzymatic patterns in the bacterial oxidation of tryptophan. J. Bacter. 58, 45–60 (1949).
Stapp, C., u. G. Spicher: Untersuchungen über die Wirkung von 2:4-d im Boden. IV. Mitt. Flavobacterium peregrinum n.sp. und seines Fähigkeit zum Abbau des Hormones. Zbl. Bakter., II. Abt. 108, 113 (1954).
Steenson, T. I., and N. Walker: Observations on the bacterial oxidation of chlorophen-oxyacetic acids. Plant a. Soil 8, 17–32 (1956); see also J. Gen. Microbiol. 16, 146-155 (1957).
Stephenson, M.: Bacterial Metabolism, 3rd. edit. London: Longmans, Green and Co. 1949.
C. N. Hinshelwood, The chemical kinetics of the bacterial cell. Oxford: Clarendon Press 1946.
Strawinski, R. J.: The dissimilation of pure hydrocarbons by members of the genus Pseudomonas. Thesis, Pennsylvania State College 1943.
Strawinski, R. J., and R. W. Stone: The utilization of hydrocarbons by bacteria. J. Bacter. 40, 461 (1940).
Conditions governing the oxidation of naphthalene and the chemical analysis of its products. J. Bacter. 45, 16 (1943).
Stormer, K.: Über die Wirkung des Schwefelkohlenstoffs und ähnlicher Stoffe auf den Boden. Zbl. Bakter., II. Abt. 20, 282–286 (1908).
Stowe, B. B.: The production of indoleacetic acid by bacteria. Biochemic. J. 61, ix (1955).
Suda, M., K. Hashimoto, H. Matsuoka and T. Kamahora: Further studies on pyrocatechase. Med. J. Osaka Univ. 2, 43–49 (1951).
Suda, M., O. Hayaishi and Y. Oda: Studies of enzyme adaptation. Tokyo Symp. Enzyme Chem. 1, 79–84 (1949).
Studies on adaptation. Successive adaptation with special reference to the metabolism of tryptophan. Med. J. Osaka Univ. 2, 21-31 (1950).
Suda, M., H. Matsuoka and T. Kamahora: Enzymatic formation of ß-ketoadipic acid. Med. J. Osaka Univ. 3, 125–128 (1952).
Suda, M., and Y. Taxeda: Metabolism of tyrosine. Application of the successive adaptation of bacteria for the analysis of the enzymatic breakdown of tyrosine. Med. J. Osaka Univ. 2, 37–40 (1950).
Tattersfield, F.: The decomposition of naphthalene in the soil and the effect upou its insecticidal action. Ann. Appl. Biol. 15, 57–80 (1928).
Tatum, E. L., R. W. Barratt, N. Fries and D. Bonner: Biochemical mutant strains of Neurospora produced by physical and chemical treatment. Amer. J. Bot. 37, 38–46 (1950).
Tatum, E. L., and D. M. Bonner: Indole and serine in the biosynthesis and breakdown of tryptophan. Proc. Nat. Acad. Sci. U.S.A. 30, 30–37 (1944).
Tatum, E. L., D. M. Bonner and G. W. Beadle: Anthranilic acid and the biosynthesis of indole and tryptophan by Neurospora. Arch. of Biochem. 3, 477–478 (1944).
Tatum, E. L., and S. R. Gross: Incorporation of carbon atoms 1 and 6 of glucose into protocatechuic acid by Neurospora. J. of Biol. Chem. 219, 797–807 (1956).
Tatum, E. L., S. R. Gross, G. Ehrensvard and L. Garnjobst: Synthesis of aromatic compounds by Neurospora. Proc. Nat. Acad. Sci. U.S.A. 40, 271–276 (1954).
Tausson, V. O.: Basic Principles of Plant Bioenergetics. Collected works of V. O. Tausson, publishing house of Acad. Sciences of U.S.S.R. (1950), edit. N. A. Maximov.
Thimann, K. V.: On the plant growth hormone produced by Rhizopus suinus. J. of Biol. Chem. 109, 279–291 (1935).
Treccani, R. Benetti and A. Schiesser: Action of some Flavobacteria on benzoic acid and various phenols. IV. Internat. Congr. Soil Sci., vol. 1, p. 186–190. Groningen (Netherlands): Publ. Heitsema Bro. 1950.
Treccani, V., N. Walker and G.H. Wiltshire: The metabolism of naphthalene by soil bacteria. J. Gen. Microbiol. 11, 341–348 (1954).
Udenfriend, S., C.T. Clarke, J. Axelrod and B. B. Brodie: Ascorbic acid in aromatic hydroxylation. 1. A model system for aromatic hydroxylation. J. of Biol. Chem. 208, 731–739 (1954).
Udenfriend, S., and J. R. Cooper: The enzymatic conversion of phenylalanine to tyrosine. J. of Biol. Chem. 194, 503–511 (1952).
Udenfriend, S., and C. Mitoma: Conversion of phenylalanine to tyrosine. A Symposium on Amino Acid Metabolism, edit, by W. D. McElroy and B. Glass. Baltimore: Johns Hopkins Press 1955.
Umbreit, W., W. A. Wood and I. C. Gunsalus: The activity of pyridoxal phosphate in tryptophan formation by cell-free enzyme preparations. J. of Biol. Chem. 165, 731–732 (1946).
Underhill, E. W., J. Watkin and A. C. Neish: Biosynthesis of quer-cetin in buckwheat. Parts I and II. Canad. J. Biochem. a. Physiol. 35, 219–237 (1957).
Wagner, R.: Über Benzolbakterien. Z. Gärungsphysiol. 4, 289–319 (1914).
Walker, N., and W. C. Evans: Metabolism of the monohydroxybenzoic acids by soil bacteria. Biochemie. J. 52, xxiii (1952).
Walker, N., and G.H. Wiltshire: The breakdown of naphthalene by a soil bacterium. J. Gen. Microbiol. 8, 273–276 (1953); 12, 478-483 (1955).
Webley, D. M., R. B. Duff and V. C. Farmer: Formation of a β-hydroxy acid as an intermediate in the microbiological conversion of monochlorophenoxybutyric acids to the corresponding substituted acetic acids. Nature (Lond.) 179, 1130 (1957).
Weiss, U., B. D. Davis and Elizabeth S. Mingioli: Aromatic biosynthesis. X. Identification of an early precursor as 5-dehydroquinic acid. J. Amer. Chem. Soc. 75, 5572–5576 (1953).
Weiss, U., C. Gilvarg, Elizabeth S. Mingioli and B.D. Davis: Aromatic biosynthesis. XI. The aromatic step in the synthesis of phenylalanine. Science (Lancaster, Pa.) 119, 774–775 (1954).
Weiss, U., and Elizabeth S. Mingioli: Aromatic biosynthesis. XV. The isolation and identification of shikimic acid-5-phosphate. J. Amer. Chem. Soc. 78, 2894–2898 (1956).
Winogradsky, S.: Microbiologie du sol. Oeuvres completes. Paris: Masson&Cie. 1949.
Wiss, O., u. G. Bettendorf: 2. Die Isolierung und vorläufige Charakterisierung des primären Oxydationsproduktes der 3-Hydroxy-anthranilsäure. Z. physiol. Chem. 306, 145–153 (1957).
Wiss, O., H. Simmer u. H. Peters: Über die Umwandlung der 3-Hydroxy-anthranilsäure in Chinolinsäure und Nicotinsäure im tierischen Organismus. 1. Die enzy-matische Oxydation der 3-Hydroxy-anthranilsäure. Z. physiol. Chem. 304, 221–231 (1956).
Wortmann, J.: Diastatic ferment of bacteria. Z. physiol. Chem. 6, 287–329 (1882).
Yaniv, H., and C. Gilvarg: Aromatic biosynthesis. XIV. 5-Dehydroshikimic acid reductase. J. of Biol. Chem. 213, 787–795 (1955).
Yanofsky, C: Tryptophan desmo-lase of Neurospora: Partial purification and properties. J. of Biol. Chem. 194, 279–286 (1952).
The absence of a tryptophan-niacin relationship in Escherichia coli and Bacillus subtilis. J. Bacter. 68, 577-584 (1954).
Tryptophan and niacin synthesis in various organisms. Symp. on Amino Acid Metabolism, edit. W. D. McElroy and B. Glass, p. 930-939. Baltimore: Johns Hopkins Press 1955.
On the conversion of anthranilic acid to indole. Science (Lancaster, Pa.) 121, 138 (1955).
J. of Biol. Chem. 223, 171-184 (1956).
Enzymatic studies with a series of tryptophan auxotrophs of E. coli. J. of Biol. Chem. 224,783-792 (1957).
Young, L.: The oxidation of polycyclic hydrocarbons in the animal body. Biochem. Soc. Symp. 1950, No 5, 27-39.
Zobell, C. E.: Action of micro-organisms on hydrocarbons. Bacter. Rev. 10, No 1-2, 1–49 (1946).
Adv. Enzymol. 10, 443-486 (1950).
Anchel, M.: Identification of the antibiotic substance from Cassia reticulata aus 4,5-dihydroxyanthraquinone-2-carboxylic acid. J. biol. Chem. 177, 169–177 (1949).
Andreae, S. R., and W. A. Andreae: Metabolism of scopoletin by healthy and virus-infected potato tubers. Canad. J. Res. 26, 31–44 (1948).
Arnow, L. E.: The formation of dopa by the exposure of tyrosine solutions to ultra-violet radiations. J. biol. Chem. 120, 151–153 (1937).
Destruction of phenylalanine by ultraviolet radiant energy. Proc. Soc. exp. Biol. 49, 578-579 (1942).
Asano, M., and K. Yamaguti: Über die Konstitution des Embelins. J. pharma-ceut. Soc. Jap. 60, 34, 237 (1940). Zit. nach Hoffmann-Ostenhof 1955.
Auterhoff, H.: Vergleichende Untersuchungen der Rinden von Rhamnus frangula und Rhamnus purshiana. IV. Mitt.: Anthrachinone. Arzneimittel-Forsch. 3, 137–139 (1953).
Baker, D., and H. Nelson: Tyrosinase and plant respiration. J. gen. Physiol. 26, 269–276 (1943).
Barnes, R. A., and N. N. Gerber: The antifungal agent from Osage orange wood. J. Amer. chem. Soc. 77, 3259–3262 (1955).
Bate-Smith, E. C., and T. N. Morris: Food Science. A Symposium on Quality and Preservation of Foods. New York: Cambridge University Press 1952.
Beevers, H.: The oxidation of reduced diphospho-pyridine nucleotide by an ascorbate system from cucumber. Plant Physiol. 29, 265–269 (1954).
Bernthsen, A.: Über das Juglon. Ber. dtsch. chem. Ges. 17, 1945 (1884).
Bertrand, D.: Bull. Soc. Chim. biol. (Paris) 26, 40 (1944). Zit. nach Dawson u. Tarpley 1951.
Oxydation von Cystein durch Laccase. C. R. Acad. Sci. (Paris) 224, 605-607 (1947).
Chem. Zbl. 118, 879 (1947).
Birch, A. J.: Biosynthetic relations of some natural phenolic and enolic compounds. Fortschr. Chem. organ. Naturstoffe 14, 186–216 (1957).
Birch, A. J., and F. W. Donovan: Studies in relation to biosynthesis. Aust. J. Chem. 6, 360–378 (1953).
Bohlmann, F., u. H. J. Mannhardt: Acetylenverbindungen im Pflanzenreich. Fortschr. Chem. organ. Naturstoffe 14, 1–70 (1957).
Bonner, J., and A. W. Galston: Toxic substances from the culture media of guayule which may inhibit growth. Bot. Gaz. 106, 185–198 (1944).
Bonner, J., and S. G. Wildman: Enzymatic mechanisms 1 Ein gewisser positiver Selektionswert liegt, wie neuerdings von Rudorf und Schwarze beobachtet wurde, insofern vor, als auf dem Feld cumarinarme Pflanzen von Hasen eindeutig stärker befressen werden als Pflanzen mit normalem Cumaringehalt. in the respiration of spinach leaves. Arch. Biochem. 10, 497–518 (1946).
Boswell, J. G., and G. C. Whiting: A study of the polyphenoloxidase systems in potato tubers. Ann. Botany N. S. 2, 847–863 (1938).
Bourton et Robiquet: Sur la semence de moutarde. J. Pharmacie (II) 17, 279–308 (1831).
Branch, G. E. K., and M. Calvin: The Theory of Organic Chemistry. New York: Prentice-Hall 1941.
Brockmann, H.: Photodynamisch wirksame Pflanzenfarbstoffe. Fortschr. Chem. organ. Naturstoffe 14, 141–185 (1957).
Brown, St. A., and A. C. Neish: Shikimic acid as a precursor in lignin biosynthesis. Nature (Lond.) 175, 688–689 (1955).
Studies of lignin biosynthesis using isotopic carbon. IV. Formation from some aromatic monomers. Canad. J. Biochem. 33, 948-962 (1955).
Studies of lignin biosynthesis using isotopic carbon. V. Comparative studies on different plant species. Canad. J. Biochem. 34, 769-778 (1956).
Bu’Lock, J. D.: Acetylenic compounds as natural products. Quart. Rev. chem. Soc. 10, 371 (1956).
Christiansen-Weniger, E.: Versuche zur stoffwechselphysiologischen Beeinflussung der Reaktion der Kartoffelknolle auf Phytophthora infestans de By. Phytopath. Z. 25, 153–180 (1956).
Daglish, C: The isolation and identification of a hydrojuglone glycoside occurring in the walnut. Biochem. J. 47, 452–457 (1950).
The determination and occurrence of a hydrojuglone glucoside in the walnut. Biochem. J. 47, 458-462 (1950).
Dalgliesh, C. E.: Non specific formation of hydroxylated metabolites of the aromatic amino acids. Arch. Biochem. 58, 214–226 (1955).
Danner, H.: Zur Physiologie des Arbutins. Bot. Archiv 41, 168–202 (1940).
Daube, F. W.: Ber. dtsch. chem. Ges. 3, 609 (1870). Zit. nach Skinner 1955.
Davis, B. D.: Intermediates in amino-acid-biosynthesis. Advanc. Enzymol. 16, 247–312 (1955).
Dawson, C. R., and N. B. Tarpley: Copper oxidases. In: J. B. Sumner and K. Myrbäck, The Enzymes, vol. II, p. 454–498. New York: Academic Press 1951.
DeSaint-Rat, L., H. R. Oliver et J. Chouteau: Bull. Acad. Méd. (Paris) 130, 57 (1946). Zit. nach Skinner 1955.
Dulong d’Astafort: J. pharm. Sci. access. Paris 14, 441 (1829). Zit. nach Skinner 1955.
Eberhardt, F.: Über die Beziehungen zwischen Atmung und Anthocyansynthese. Planta (Berl.) 43, 253–287 (1954).
Über fluoreszierende Verbindungen in der Wurzel des Hafers. Z. Bot. 43, 405-422 (1955).
Eichbaum, F. W.: Biological properties of ana-cardic acid (o-pentadecadienyl-salicylic acid) and related compounds. Mem. Inst. Butanan 19, 71–133 (1946). Ref. Biol. Abstr. 21, Nr. 25364 (1947).
Eiger, I. Z., and C. R. Dawson: Sweet potato phenolase. Preparation, properties and determination of protein content. Arch. Biochem. 21, 194–209 (1949).
Erdtman, H.: Die phenolischen Inhaltsstoffe des Kiefernkernholzes, ihre physiologische Bedeutung und hemmende Einwirkung auf die normale Aufschließung des Kiefernkernholzes nach dem Sulfitverfahren. Liebigs Ann. 539, 116–127 (1939).
Natural Tropolones. In: Moderne Methoden der Pflanzenanalyse, Bd. III, S. 351-358. Berlin-Göttingen-Heidelberg: Springer 1955.
Evans, M. G., J. Gergely and J. de Heer: Trans. Faraday Soc. 45, 312 (1949). Zit. nach Mason
Evans, M. G., and J. de Heer: Quart. Rev. 4, 94 (1950). Zit. nach Mason 1955.
Fawcett, C. H., J. M. A. Ingram and R. L. Wain: β-Oxidation of ω-phenoxyalkyl-carboxylic acids in the flax plant. Nature (Lond.) 170, 887–888 (1952).
Friedrich, H.: Hydrojuglon und Vitamin C in der Walnuß (Juglans regia). Pharmazie 8, 90–94 (1953).
Untersuchungen über den Gerbstoff von Bergenia-Arten und seine Beziehungen zum Arbutin. Pharmazie 9, 138-155, 240-251 (1954).
Untersuchungen über phenolische Inhaltsstoffe von Pyrus communis L. 1. Mitt.: Zusammenstellung der bisherigen Veröffentlichungen. Pharmazie 12, 691–693 (1957).
Untersuchungen über die phenolischen Inhaltsstoffe von Pyrus communis L. 2. Mitt.: Der Arbutingehalt der Birnenblätter. Pharmazie 12, 831–834 (1957).
Fuchs, W. H.: Ein Beitrag zur pathologischen Physiologie. Angew. Bot. 30, 141–146 (1956).
Geissman, T. A.: The flavonoid constituents of normal and virus-infected peach and cherry leaves. Arch. Biochem. 60, 21–26 (1956).
Geissman, T. A., and D. K. Fukushima: J. Amer. chem. Soc. 70, 1686 (1948). Zit. nach Underhill, Watkin u. Neish 1957b.
Geissman, T. A., and J. B. Harborne: The chemistry of flower pigmentation in Antirrhinum majus. IV. The albino (-mm-nn) form. Arch. Biochem. 55, 447–454 (1955).
Geissman, T. A., and E. Hinreiner: Theories of the biogenesis of flavonoid compounds. Bot. Rev. 18, 77–244 (1952).
Geissman, T. A., and T. Swain: Biosynthesis of flavonoid compounds in higher plants. Chem. and Ind. 1957, 984.
Gildemeister, E., u. F. Hoffmann: Die ätherischen Öle, 3. Aufl. Leipzig: Schimmel & Co. 1928-1931. 3 Bände.
Gilman, H., P. R. van Ess and R. R. Burtner: The constitution of carlinaoxide. J. Amer. chem. Soc. 55, 3461 (1933). Zit. nach Bohlmann u. Mannhardt 1957.
Goris, A., et M. Mascré: Sur l’existence, dans le Primula officinalis Jacq., de deux nouveaux glucosides dédoublables par un ferment. C. R. Acad. Sci. (Paris) 149, 947–950 (1910).
Grahle, A.: Untersuchungen zur Gewinnung einheimischer Arzneipfanzen. I. Der Anthraglykosidgehalt der Kreuzdornbeeren und seine Veränderungen während der Fruchtreife und bei der Ernte. Süddtsch. Apoth.-Ztg. 86, 51–56 (1946).
Griffiths, A. B.: Chem. News 49, 90 (1884).
Nach F. Czapek, Biochemie der Pflanzen, Bd. III, S. 449. Jena: Gustav Fischer 1925.
Grimal, E.: Sur l’essence de bois de Thuja articulata d’Algérie. C. R. Acad. Sci. (Paris) 139, 927 (1904).
Grisebach, H.: Zur Biogenese des Cyanidins. I. Mitt. Z. Naturforsch. 12b, 227–231 (1957).
Grundon, M.F., and F.E. King: Chlorophorin, a constituent of Iroko, the timber of Chlorophora excelsa. Nature (Lond.) 163, 564–565 (1949).
Hasegawa, M., S. Yoshida and T. Nakagawa: Shikimic acid in plant leaves. Kakagu Science 24, 421–422 (1954).
Hérissey, H., u. J. Cheymol: Gewinnung und Eigenschaften des Geins, des Eugenol liefernden Glucosids in Gewm urbanum L. C. R. Acad. Sci. (Paris) 180, 384, 386 (1925). Ref. Chem. Zbl. 1925 I, 1749.
Hérissey, M., et H. J. Laforest: Sur un hétéroside extrait du Laurier du Portugal, Cerasus lusitanica. C. R. Acad. Sci. (Paris) 194, 1095–1097 (1932).
Herrmann, K.: Über Kaffeesäure und Chloro-gensäure. Pharmazie 11, 433–449 (1956).
Hesse, O.: Pharm. J. 1, 325 (1895). Zit. nach Skinner 1955.
Hewitt, L. F.: Oxidation-Reduction Potentials in Bacteriology and Biochemistry. Edinburgh: Livingstone 1950.
Hieke, K.: Der Anthrachinonstoff-wechsel in Polygonaceen. Bot. Archiv 41, 113–158 (1940).
Hoffmann-Ostenhof, O.: Vorkommen und biochemisches Verhalten der Chinone. Fortschr. Chem. organ. Naturstoffe 6, 154–241 (1950).
Ein-und zweikernige Chinone. In: Moderne Methoden der Pflanzenanalyse, Bd. III, S. 359-391. Berlin-Göttingen-Heidelberg: Springer 1955.
Hooker, S. C.: The constitution of “lapachic acid” (lapachol) and its derivatives. J. chem. Soc. 61, 611 (1892).
The constitution of lapachol and its derivatives. J. chem. Soc. 69, 1355 (1896).
Imai, K.: Studies on the essential oil of Artemisia capillaris Thunb. III. Antifungal activity of the essential oil. Structure of antifungal principle capillin. J. pharmaceut. Soc. Jap. 76, 405 (1956). Zit. nach Bohlmann u. Mannhardt.
Iwanof-Gajewsky: Ber. dtsch. chem. Ges. 3, 624 (1870). Zit. nach Skinner 1955.
James, W. O.: Plant Respiration. Oxford: Clarendon Press 1953.
James, W. O.: The terminal oxidase in the respiration of the embryos and young roots of barley. Proc. roy. Soc. B 141, 289–299 (1953).
James, W. O., E. A. H. Roberts, H. Beevers and P. C. de Kock: The secondary oxidation of amino acids by the catechol oxidase of belladonna. Biochem. J. 43, 626–636 (1948).
Johnson, G., and L. A. Schaal: Relation of chlorogenic acid to scab resistance in potatoes. Science 115, 627–629 (1952).
Accumulation of phenolic substances and ascorbic acid in potato tuber tissue upon injury and their possible role in disease resistance. Amer. Potato J. 34, 200-209 (1957).
Joslyn, M. A., and J. D. Ponting: Enzymes catalyzed oxidative browning of fruit products. Advanc. Food Res. 3, III (1951).
Karrer, W.: Über das Vorkommen von 2,6-Dimethoxychinon in Adonis vernalis. Helv. chim. Acta 93, 1424 (1930).
Keilin, D., and T. Mann: Nature (Lond.) 145, 304 (1940).
Kenkare, U. W., and K. Sohonie: The “phenolase” from brinjal (Solanum melongena). Current Sci. 20, 268–269 (1951).
Kjaer, A.: Secondary organic sulfur compounds of plants. In: Handbuch der Pflanzenphysiologie, Bd. IX, S. 64–88. Berlin-Göttingen-Heidelberg: Springer 1958.
Klein, G., E. Siersch u. H. Linser: Zum mikrochemischen Nachweis freier Phenole in der Pflanze. Ost. bot. Z. 80, 223–249 (1931).
Kötter, Cl.: Das Auftreten sekundärer Pflanzenstoffe im Verlauf der Wundperidermbildung bei Kartoffeln. Diss. Göttingen 1957.
Koninck, L. de: Über das Phloridzin (Phlorrhizin). Liebigs Ann. 15, 75–77 (1835).
Weitere Notiz über das Phloridzin. Liebigs Ann. 15, 258-263 (1835).
Kubowitz, F.: Über die chemische Zusammensetzung der Kartoffeloxydase. Biochem. Z. 292, 221–229 (1937).
Spaltung und Resynthese der Polyphenoloxydase und des Hämocyanins. Biochem. Z. 299, 32-57 (1938).
Kuc, J., R. E. Menze, A. J. Ullstrup and F. W. Quackenbush: Chlorogenic and caff eic acids as f ungistatic agents produced by potatoes in response to inoculation with Helminthosporium carbonum. J. Amer. chem. Soc. 78, 3123 (1956).
Kursanow, A. L.: Synthese und Umwandlung der Gerbstoffe in der Teepflanze. Berlin: Verlag Volk u. Gesundheit 1954.
Die Gerbstoffe der Teepflanze. In: Die Kulturpflanze, Beih. 1, S. 29-48. Berlin: Akademie-Verlag 1955.
Lampe, V.: Ber. dtsch. chem. Ges. 51, 1347 (1918). Zit. nach Skinner 1955.
Lang, W.: Zur Physiologie der Naphthochinone und Gerbstoffe in Pflanzen. Pharm. Zentralh. 80, 713–716 (1939).
Lardy, H.A. (Ed.): Respiratory Enzymes. Minneapolis: Burgess 1949.
Lerner, N. H.: Polyphenoloxidase and the respiration of ivy leaves. J. exp. Bot. 5, 79–90 (1954).
Levy, H., and A. Schade: Terminal oxidase system of potato tuber respiration. Arch. Biochem. 19, 273–286 (1948).
Lindstedt, G., and A. Misiorny: Constituents of pine heartwood. XXV. Investigation of forty-eight Pinus species by paper partition chromatography. Acta chem. scand. 5, 121 (1951).
Constituents of pine heart-wood. XXVIII. Investigation of four additioned Pinus species by paper partition chromatography. Acta chem. scand. 6, 744-746 (1952).
Link, G. K. K., and R. M. Klein: Studies on the metabolism of plant neoplasms. II. The terminal oxidase patterns of crown-gall and auxin tumors of tomato. Bot. Gaz. 113, 190–195 (1951).
Link, K. P., H. R. Angell and J. C. Walker: The isolation of protocatechuic acid from pigmented onion scales and its significance in relation to disease resistance in onions. J. biol. Chem. 81, 369–375 (1929).
Link, K. P., and J. C. Walker: The isolation of catechol from pigmented onion scales and its significance in relation to disease resistance in onions. J. biol. Chem. 100, 379–383 (1933).
Little, J. E., T. J. Sproston and M. W. Foote: Isolation and antifungal action of naturally occurring 2-methoxy-l,4-naphthoquinone. J. biol. Chem. 174, 335–342 (1948).
Mason, H. S.: Comparative biochemistry of the phenolase complex. Advanc. Enzymol. 16, 105–184 (1955).
Mason, H. S., J. Onopryrenko and D. Buhler: Hydroxylation: the activation of oxygen by peroxidase. Biochim. biophys. Acta 24, 225–226 (1957).
Merz, K. W., u. R. Preuss: Konstitution und Synthese von Taxicatin. Arch. Pharm. (Weinheim) 279, 134–148 (1941).
Mitoma, C., and L. C. Leeper: Enzymatic conversion of phenylalanin to tyrosine. Fed. Proc. 13, 266 (1954).
Mitoma, C, H. S. Posner, H. C. Reitz and S. Udenfriend: Enzymatic hydroxylation of aromatic compounds. Arch. Bio-chem. 61, 431–441 (1956).
Mothes, K., u. H. Kala: Die Wurzel als Bildungsstätte für Cumarine. Naturwissenschaften 42, 159 (1955).
Naghski, J., M.J. Copley and J.F. Couch: The antibacterial action of flavonols. J. Bact. 54, 34 (1947).
Effect of flavonols on the bacteriostatic action of dicoumarol. Science 105, 125-126 (1947).
Newton, R., and J. A. Anderson: Studies on the nature of rust resistance in wheat. IV. Phenolic compounds of the wheat plant. Canad. J. Res. 1, 86–99 (1929).
Niethammer, A.: Mikroskopie und Mikrochemie bekannter heimischer Früchte. Planta (Berl.) 12, 399–413 (1931).
Nozoe, T.: Natural tropolones and some related troponoids. Fortschr. Chem. organ. Naturstoffe 13, 222–301 (1956).
Onslow, M. W.: Principles of Plant Biochemistry, S. 130. Cambridge: University Press 1931.
Oppenheimer, C., and K. G. Stern: Biological Oxidation. New York: Nordemann 1939.
Paech, K.: Biochemie und Physiologie der sekundären Pflanzenstoffe. Berlin-Göttingen-Heidelberg: Springer 1950.
Stoffwechsel organischer Verbindungen. II. Fortschr. Bot. 17, 578-620 (1954).
Paech, K., u. F. Eberhardt: Untersuchungen zur Biosynthese der Anthocyane. Z. Naturforsch. 7b, 669–670 (1952).
Perkin, A. G., and J. J. Hummel: J. chem. Soc. Trans. 69, 1295 (1896).
Proc. chem. Soc. 12, 144 (1896). Zit. nach Skinner 1955.
Picard, P.: Le violutoside, nouveau glucoside à salicylate de méthyle, retiré du Viola cornuta. C. R. Acad. Sci. (Paris) 182, 1167–1169 (1926).
Pisek, A.: Chemie des Zellsaftes. In: Handbuch der Pflanzenphysiologie, Bd. I, S. 614–626. Berlin-Göttingen-Heidelberg: Springer 1955.
Politis, J.: Cytological researches on the mode of formation of chlorogenic acid. Rev. Cytol. Cytophysiol. vég. 10, 229–235 (1948).
Price, J. R., and R. Robinson: A new natural pigment of the naphthalene series. Nature (Lond.) 142, 147 (1938).
Preisler, P. W.: Cold Spr. Harb. Symp. quant. Biol. 7, 94 (1939).
Raper, H. S.: Note on the oxidation of tyrosine, tyramine, and phenylalanine with hydrogen peroxide. Biochem. J. 26, 2000–2004 (1932).
Rennie, E.H.: Glycyphyllin, the sweet principle of Smilax glycyphylla. J. chem. Soc. 49, 857–865 (1886).
Robbins, W. J., F. Kavanagh and J. D. Thayer: Antibiotic activity of Cassia reticulata Willd. Bull. Torrey Bot. Club 74, 287–292 (1947).
Roberts, E. A. H., and D. J. Wood: The separation of polyphenols in tea leaf by paper chromatography with water as a mobile solvent. Biochem. J. 49 (Proc.), XXXIII (1951).
A study of polyphenols in tea leaf by paper chromatography. Biochem. J. 49, 414-422 (1951).
Roberts, R. B., P. H. Abelson, D. B. Cowie, E. T. Bolton and R.J. Britten: Carnegie Inst. Wash. Publ. 607, 406 (1955). Zit. nach Underhill, Watkin u. Neish 1957b.
Robinson, E. S., and J. M. Nelson: The tyrosine-tyrosinase reaction and aerobic plant respiration. Arch. Biochem. 4, 111–117 (1944).
Rubin, B. A., u. E. W. Arzichowskaja: Biochemische Charakteristik der Widerstandsfähigkeit der Pflanzen gegenüber Mikroorganismen. Berlin: Akademie-Verlag 1953.
Ruckenbrod, H.: Untersuchungen über den Umsatz der Chlorogensäure in höheren Pflanzen. Planta (Berl.) 46, 19–45 (1955).
Rudorf, W., u. P. Schwarze: Beiträge zur Züchtung eines cumarinfreien Steinklees und Untersuchungen über Cumarin und verwandte Verbindungen. Z. Pflanzenzüchtung 39, 245–274 (1958).
Ruelius, H. W., u. A. Gauhe: Isolierung und Konstitution eines Hydrojuglonglucosids aus den grünen Schalen der Walnuß. Liebigs Ann. 571, 69–75 (1951).
Ruhemann, S., u. S. Skinner: Ber. dtsch. chem. Ges. 20, 1861 (1867). Zit. nach Skinner 1955.
Schade, A., and H. Levy: Changes in the terminal oxidase pattern of potato tissue associates with time of suspension in water. Arch. Biochem. 20, 211–219 (1949).
Scheibe, A., u. G. Hülsmann: Über das Auftreten bitterstoffarmer Pflanzen von Melilotus albus in der C2-Generation nach Behandlung mit mutagenen Chemikalien. Naturwissenschaften 44, 17–18 (1957).
Schmid, H.: Natürlich vorkommende Chromone. Fortschr. Chem. organ. Naturstoffe 11, 124–179 (1954).
Schmid, H., u. Th. M. Meijer: Über die Konstitution des Eugenons. Helv. chim. Acta 31, 748–752 (1948).
Schmid, W.: Anthraglykoside und Dianthrone. In: Moderne Methoden der Pflanzenanalyse, Bd. III, S. 549–564. Berlin-Göttingen-Heidelberg: Springer 1955.
Schratz, E.: Pharmakognostische Untersuchungen am Medizinal-Rhabarber (Rheum palmatum L.). Pharmazie 11, 138–150 (1956).
Schraufstätter, E., and H. Bernt: Antibacterial action of curcumin and related compounds. Nature (Lond.) 164, 456–457 (1949).
Schwarze, P.: Beobachtungen über Bildung und Abbau des Sinapins im Raps. Unveröffentlicht.
Über das freie und gebundene Cumarin des Steinklees. Unveröffentlicht.
Semmler, F. W.: Zusammensetzung des ätherischen Öles der Eberwurzel (Carlina acaulis L.). Ber. dtsch. chem. Ges. 39, 726 (1906).
Shimokoriyama, M., and S. Hattori: J. Amer. chem. Soc. 75, 2277 (1953). Zit. nach Underhill, Watkin u. Neish 1957b.
Shiroya, M., and S. Hattori: Studies on the browning and blackening of plant tissues. III. Occurrence in the leaves of Dahlia and several other plants of chlorogenic acid as the principal browning agent. Physiol. Plantarum (Cph.) 8, 358–369 (1953).
Shiroya, M., T. Shiroya and S. Hattori: Studies on the browning and blackening of plant tissues. IV. Chlorogenic acid in the leaves of Nicotiana tabacum. Physiol. Plantarum (Cph.) 8, 594–605 (1955).
Siebs, E.: Untersuchungen über die Schorfresistenz von Birnen. III. Stofflicher Hinweis auf die Grundlagen der Blattschorfresistenz. Phytopath. Z. 23, 37–48 (1955).
Singer, T. P., and E. B. Kearney: In: Neurath u. Bailey, The proteins, vol. II, A, p. 123. New York: Academic Press 1954.
Skinner, P.A.: Antibiotics. In: Moderne Methoden der Pflanzenanalyse, Bd. III, S. 626–725. Berlin-Göttingen-Heidelberg: Springer 1955.
Smith, W. K.: Transfer from Melilotus dentata to M. alba of the genes for reduction in coumarin content. Genetics 33, 124–125 (1948).
Sörensen, J. S., and N. A. Sörensen: Studies related to naturally occurring acetylene compounds. XVII. Four new polyacetylenes from garden varieties of Coreopsis. Acta chem. scand. 8, 1741 (1954).
Sörensen, N. A.: Acetylenic compounds from plants of the compositae family. Chem. and Ind. 1953, 240.
Stadelmann, R., et A. Mirimanoff: Contribution à la phytochimie du péricarpe de Juglans regia. Phyton 2, 1–7 (1950).
Städeler, G.: Chem. Gaz. 6, 29, 58 (1848). Zit. nach Skinner 1955.
Stevens, G. de, and F. F. Nord: Natural phenyl-propane derivatives. In: Moderne Methoden der Pflanzenanalyse, Bd. III, S. 392–427. Berlin-Göttingen-Heidelberg: Springer 1955.
Stoll, A., B. Becker u. W. Kussmaul: Die Isolierung der Anthraglykoside aus Sennadrogen. Helv. chim. Acta 32, 1892–1903 (1949).
Stoll, A., u. E. Jucker: Heteroside. Aufbau und Vorkommen. In: Handbuch der Pflanzenphysiologie, Bd. VI, S. 534–779. Berlin-Göttingen-Heidelberg: Springer 1958.
Thies, W., u. C. Wehmer: Systematische Verbreitung und Vorkommen der ätherischen Öle und ihrer Bestandteile. In: Handbuch der Pflanzenanalyse, Bd. III/2, S. 571–666. Wien: Springer 1932.
Thimann, K. V., C. S. Yocum and D. P. Hackett: Terminal oxidases and growth in plant tissues. III. Terminal oxidation in potato tuber tissue. Arch. Biochem. 53, 239–257 (1954).
Thomas, H. K.: Ätherische Öle. In: Handbuch der Pflanzenanalyse, Bd. II/1, S. 453–570. Wien: Springer 1932.
Tissières, A.: Localization of polyphenoloxidase in the chloroplasts of Beta vulgaris. Nature (Lond.) 162, 340–342 (1948).
Tutin, F., and H. W. B. Clewer: J. chem. Soc. 99, 946 (1911). Zit. nach Skinner 1955.
Tyron, K.: Scopoletin in differentiating and non differentiating cultured tobacco tissue. Science 123, 590 (1956).
Udenfriend, S., C. T. Clarke, J. Axelrod and B. B. Brodie: Ascorbic acid in aromatic hydroxylation. I. A model system for aromatic hydroxylation. J. biol. Chem. 208, 731–739 (1954).
Underhill, E. W., J. E. Watkin and A. C. Neish: Biosynthesis of quercetin in buckwheat. Part. I. Canad. J. Biochem. 35, 219–228 (1957).
Uritani, J., and J. Hoshiya: Coumarin substances from sweet potato and their physiology. J. agric. chem. Soc. Jap. 27, 161–174 (1953).
Virtanen, A. I., P. K. Hietala and Ö. Wahlroos: Antimicrobial substances in cereals and fodder plants. Arch. Biochem. 69, 486–500 (1957).
Waage, Th.: Über das Vorkommen und die Rolle des Phloroglucins in der Pflanze. Ber. dtsch. bot. Ges. 8, 250–292 (1890).
Wailes, P.C.: The occurrence of acetylenic compounds in nature. Rev. Pure Appl. Chem. 6, 61 (1956).
Walker, J. C., and M. A. Stahmann: Chemical nature of disease resistance in plants. Ann. Rev. Plant Physiol. 6, 351–366 (1955).
Watkin, J. E., E. W. Underhill and A. C. Neish: Biosynthesis of quercetin in buckwheat. Part II. Canad. J. Biochem. 35, 229–237 (1957).
Webster, G. C.: The effect of carbon monoxide on respiration in higher plants. Plant Physiol. 29, 399–400 (1954).
Weevers, Th.: Die physiologische Bedeutung einiger Glykoside. Rec. Trav. bot. néerl. 7, 1–54 (1910).
Wehmer, C., W. Thies u. M. Hadders: Vorkommen und systematische Verbreitung der Phenole und Chinone. In: Handbuch der Pflanzenanalyse, Bd. H/1, S. 345–362. Wien: Springer 1932.
Wood, J. G., and D. H. Cruickshank: Changes in amounts of some amino-acids during starvation of grass leaves, and their bearing on the nature of the relationship between proteins and amino acids. Aust. J. exp. Biol. med. Sci. 22, 111–123 (1944). Zit. J. Bonner, Plant Biochemistry. New York: Academic Press 1950.
Wosilait, W. D., and A. Nason: Pyridine nucleotide-quinone reductase. I. Purification and properties of the enzyme from pea seeds. J. biol. Chem. 206, 255–270 (1954).
Wosilait, W. D., A. Nason and A. J. Terrell: Pyridine nucleotide-quinone reductase. II. Role in electron transport. J. biol. Chem. 206, 271–282 (1954).
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Evans, C., Schwarze, P. (1958). Phenole, Chinone und die biogene Bildung von Benzolkernen. In: Der Stoffwechsel Sekundärer Pflanzenstoffe / The Metabolism of Secondary Plant Products. Handbuch der Pflanzenphysiologie / Encyclopedia of Plant Physiology, vol 10. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-26784-4_14
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