Identification of phenyldecanoic acid as a constituent of triacylglycerols and wax ester produced by Rhodococcus opacus PD630.

Phenyldecane supported growth and lipid accumulation of Rhodococcus opacus PD630 during cultivation under nitrogen-limiting conditions. The results of this study suggested that the hydrocarbon phenyldecane was degraded by monoterminal oxidation, followed by beta-oxidation of the alkyl side-chain to phenylacetic acid, and by an additional degradative route for the oxidation of the latter to intermediates of the central metabolism. alpha-Oxidation of phenyldecanoic acid also occurred to some extent. Phenyldecanoic acid, the monoterminal oxidation product, was also utilized for the biosynthesis of a novel wax ester and novel triacylglycerols. The formation of the wax ester phenyldecylphenyldecanoate probably resulted from the condensation of phenyldecanoic acid and phenyldecanol, which were produced as metabolites during the catabolism of phenyldecane. Two types of triacylglycerol were detected in phenyldecane-grown cells of strain PD630. Triacylglycerols containing only odd- and even-numbered aliphatic fatty acids, as well as triacylglycerols in which one fatty acid was replaced by a phenyldecanoic acid residue, occurred. Other phenyl intermediates, such as phenylacetic acid, phenylpropionic acid, 4-hydroxyphenylpropionic acid, protocatechuate and homogentisic acid, were excreted into the medium during cultivation on phenyldecane. On the basis of the results obtained, pathways for the catabolism and assimilation of phenyldecane by R. opacus PD630 are discussed.

[1]  Mark R. Smith.  The biodegradation of aromatic hydrocarbons by bacteria , 2004, Biodegradation.

[2]  H. Schlegel,et al.  Ein Submersverfahren zur Kultur wasserstoffoxydierender Bakterien: Wachstumsphysiologische Untersuchungen , 2004, Archiv für Mikrobiologie.

[3]  O. Pucci,et al.  Biosynthesis of fatty acids and triacylglycerols by 2,6,10,14-tetramethyl pentadecane-grown cells of Nocardia globerula 432. , 2001, FEMS microbiology letters.

[4]  A. Steinbüchel,et al.  Accumulation and mobilization of storage lipids by Rhodococcus opacus PD630 and Rhodococcus ruber NCIMB 40126 , 2000, Applied Microbiology and Biotechnology.

[5]  S. Stymne,et al.  Phospholipid:diacylglycerol acyltransferase: an enzyme that catalyzes the acyl-CoA-independent formation of triacylglycerol in yeast and plants. , 2000, Proceedings of the National Academy of Sciences of the United States of America.

[6]  A. Steinbüchel,et al.  Rhodococcus opacus strain PD630 as a new source of high-value single-cell oil? Isolation and characterization of triacylglycerols and other storage lipids. , 2000, Microbiology.

[7]  J. García,et al.  Novel Biodegradable Aromatic Plastics from a Bacterial Source , 1999, The Journal of Biological Chemistry.

[8]  P. Golyshin,et al.  Characterization of antarctic hydrocarbon-degrading bacteria capable of producing bioemulsifiers. , 1999, The new microbiologica.

[9]  E. Moore,et al.  Microcosm Enrichment of Biphenyl-Degrading Microbial Communities from Soils and Sediments , 1998, Applied and Environmental Microbiology.

[10]  L. Whyte,et al.  Biodegradation of Variable-Chain-Length Alkanes at Low Temperatures by a Psychrotrophic Rhodococcussp , 1998, Applied and Environmental Microbiology.

[11]  E. Díaz,et al.  Molecular characterization of the phenylacetic acid catabolic pathway in Pseudomonas putida U: the phenylacetyl-CoA catabolon. , 1998, Proceedings of the National Academy of Sciences of the United States of America.

[12]  A. Steinbüchel,et al.  Molecular characterization of genes of Pseudomonas sp. strain HR199 involved in bioconversion of vanillin to protocatechuate , 1997, Journal of bacteriology.

[13]  A. Steinbüchel,et al.  Accumulation of storage lipids in species of Rhodococcus and Nocardia and effect of inhibitors and polyethylene glycol , 1997 .

[14]  A. Steinbüchel,et al.  Formation of intracytoplasmic lipid inclusions by Rhodococcus opacus strain PD630 , 1996, Archives of Microbiology.

[15]  A. Steinbüchel,et al.  FORMATION OF INTRACYTOPLASMIC LIPID INCLUSION BY RHODOCOOCUS OPACUS PD630 , 1996 .

[16]  B. Poolman,et al.  Mechanisms of membrane toxicity of hydrocarbons. , 1995, Microbiological reviews.

[17]  C. A. Fewson,et al.  Biotransformations catalyzed by the genus Rhodococcus. , 1994, Critical reviews in biotechnology.

[18]  W. Finnerty.  The biology and genetics of the genus Rhodococcus. , 1992, Annual review of microbiology.

[19]  S. W. Li,et al.  Isolation and Characterization of a Subsurface Bacterium Capable of Growth on Toluene, Naphthalene, and Other Aromatic Compounds , 1991, Applied and environmental microbiology.

[20]  R. Lenz,et al.  An unusual bacterial polyester with a phenyl pendant group , 1990 .

[21]  R. Gross,et al.  Pseudomonas oleovorans as a Source of Poly(β-Hydroxyalkanoates) for Potential Applications as Biodegradable Polyesters , 1988, Applied and environmental microbiology.

[22]  D. Gibson.  Microbial degradation of hydrocarbons , 1982 .

[23]  F. Sariaslani,et al.  Microbial degradation of hydrocarbons. Catabolism of 1-phenylalkanes by Nocardia salmonicolor. , 1974, Biochemical Journal.