Metabolism of Aromatic Compounds. Part 1. Bacterial Oxidation of Three Isomers of Monohydroxybenzoic Acids.

Transcription

1 Metabolism of Aromatic Compounds. Part 1. Bacterial Oxidation of Three Isomers of Monohydroxybenzoic Acids. By Kei ARIMA, Kazuo KOMAGATA and Shigehiko MINODA (Laberatory of Microbiology, Department of Agricultural Chemistry, Faculty of Agriculture, University of Tokyo)

2 Table 1. Assimilation of Aromatic Compounds by Isolated Bacteria _??_ Visible growth after 24 hr. + Visible growth after 48 hr. -- non Visible growth * Aerobacter aerogenes ATCC 8724 ** Detail studies of these strains will be published in Part II of this report. Components in Warburg's vessel. Main compartment 0.5 cc Cell suspension (2 `2.5mg as dry cell) 0.5 cc M/15 Phosphate buffer (ph 7.2) Center well 0.2 cc 10% KOH Side arm 0.2 cc M/100 Substrate* Temp. of, bath 30 cc * Aromatic acids were added as Na salts

3 Ps. ovalis var. S-5 Ps. ovalis var. S-5 Fig. 1. Oxidation of salicylate and related compounds by the cells of Ps. ovalis var. S-5 adapted to salicylate. Fig. 2. Relationship between oxygen uptake and concentration of salicylate and catechol by the cells of Pss ovalis var S-5 adapted to salicylate. Table 2. Non-enzymatic Oxidation of 2. 3-DOBA.

4 Micro. urea Ps. dacunhae Fig. 3. Oxidation of m-oh-benzoate and re lated compounds by the cells of Miro. ureae adapted to m-oh-benzoate. Fig. 4. Oxidation of m-oh-benzoate and related compounds by the cells of Ps. dacunhae adapted to m-ohbenzoate. Scheme II Ps. ovalis var. S-5 Fig. 5. Oxidation of p-oh-benzoate and related compounds by the cells of Ps. ovalis var. S-5 adapted to p-ohbenzoate.

5 Scheme III. Fig. 6. Adaptive lag time to several compounds by the cells of Ps. ovalis var. S-5 grown on bouillon (1) WAGNER, R.: Z. f. Garungsphysiol., 4, 289 (1914). (2), (3) STANIER, R. Y.: J. Bact., 54, 339 (1947); 55, 477 (1948). (4) SLEEPER, B. P. et al. ibid., 59, 117 (5) SLEEPER, B. P. et al.: ibid., (6) STANIER, R. Y. et al.: ibid., 59, 137 (7) STANIER, R. Y.: ibid., 59, 527 (8) SLEEPER, B. P.: ibid., 62, 567 (1951). (9) STANIER R. Y. et al.: ibid., 58, 45 (1949). (10) STANIER, et al.,: ibid., 62, 355 (1951). (11) STANIER, R. Y. et al.: ibid., 62, 367 (1951). (12) HAYAISHI, O. et at. ibid., 62, 691 (1951). (13) TSUCHIDA, M. et al. ibid., 64, 49

6 (16) SUDA, M. et al.: J. Biochem, (Japan), 37, 355 (1950) (17) SUDA, M. et al.: ibid., 37, 375 (18) HAYAISHI, O. et al.: ibid., 37, 371 (19) EVANS, W. C.: J. Soc. Chem. Ind. London, 58, 55 (1939). (20) EVANS, W. C.: Biochem. J. 41, 373 (1947). (21) EVANS, W. C. et al.: ibid., 49, prvc. x (1951). (22) SMITH, B. S. P.: ibid., 50, proc. xxviii (1951). (23) JOHNES, J. P. et al.: ibid., 51, proc. xi (1952). (24) KILBY, B. A.: ibid., 43, proc. x(1948). (25) KILBY, B. A. ibid., 49, 671 (1951). (26) GRAY, P. H. H. et al.: Zentbl. f. Bakt., II, 73, 74 (1928). (27) TAUSSON, W. O.: Planta, 4, 214 (1927). (28) TAUSSON, W. O.: Planta, 5, 239 (1928). (29) TAUSSON, W. O.: ibid, 7, 735 (1929). Summary (30) BUTKIWITSCH, Wl.: Biochem. Z., 145. (31) BUTKIWITSCH, W1.: ibid., 159, 395 (1925). (32) PERwOZWANSKY: Zentbl. f. Bakt., II, 81, 372 (1930). (33) BEMHAUER, K. et al.: Biochem. Z., 249, 223 (1932). (34) BEMHAUER, K. et al.: ibid., 280, 394 (1935). (35) TERUI, G. et al.: Technology Report of the Osaka Univ., 2 (54), 283 (1952). (42) WALTER, et al.: Bio chem. J. 52, proc. xxiii (1952). (43) DEN DOORENDE. JVNG. L. E.: Bijdrage tot de Kennis van Lut mineralsatiproces. (1926). (44) KRAMER, N. et al.: Arch. Biochem.,, 26, 401 (46) THOMPSON, P. E. et al. Antibiotics. and Chemotherapy, 3, ) About 130 bacterial strains which can utilize various aromatic compounds as the sole car bon source were isolated from soils and sewages. And their metabolic specificity and strength of metabolic activity against various aromatic compounds were shown in Table 1. Strains which exhibited strong decomposing power on some compounds were used for the present experiments. 2) The metabolic pathways of oxidative decomposition of three isomers of monohydroxybenzoic acid by simultaneous or successive adaptation technique were studied, and the foliwoing schemes were proposed by using several strains in each pathway. a) Salicylic acid b) m-hydroxybenzoic acid c) p-hydroxybenzoic acid 3) Among these pathways, oxidative pathways of m-hydroxybenzoic acid via protocatechuic acid and gentisic acid were originally proposed by the present authors. Thus it was manifes ted for the first time that there exist two pathways, i. e. pathway via protocatechu re and

7 pathway via gentisate, in oxidative decomposition of m-hydroxybenzoic acid by bacteria. 4) Oxidative decomposition of salicylic acid-legally admitted to add in sake-by Hiochi bact eria and the same decomposition of p-hydroxybenzoic alkyl esters-widely used for the fungicide of Shoyu-by p-hydroxybenzoic acid adapted bacteria were neither recognized.