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Catabolism of dl-α-phenylhydracrylic, phenylacetic and 3- and 4-hydroxyphenylacetic acid via homogentisic acid in a Flavobacterium sp.

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Abstract

A degradation pathway for dl-α-phenylhydracrylic, phenylacetic, 3- and 4-hydroxyphenylacetic acid by a Flavobacterium is presented. Experiments with washed cells and enzyme studies revealed that dl-α-phenylhydracrylic acid in an initial reaction was oxidatively decarboxylated to phenylacetaldehyde. Whole cells oxidized both stereoisomers of phenylhydracrylic acid at different rates. The product phenylacetaldehyde in turn was oxidized to phenylacetic acid. No hydroxylation of phenylacetic acid was detected in cell extracts, but on the basis of experiments with washed cells it is assumed that phenylacetic acid is mainly metabolized via 3-hydroxyphenylacetic acid. This latter product was subsequently hydroxylated yielding the ring-cleavage substrate homogentisate. 4-Hydroxyphenylacetic acid was also degraded via homogentisate. Ringcleavage of homogentisate gave maleylacetoacetate which was further degraded through a glutathione-dependent pathway. Homoprotocatechuate was not an intermediate in the metabolism of dl-phenylhydracrylic acid, phenylacetic, 3- and 4-hydroxyphenylacetic acid metabolism, but it could be hydroxylated aspecifically to 2,4,5-trihydroxyphenylacetic acid by the action of the 3-hydroxyphenylacetic acid-6-hydroxylase.

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Abbreviations

HPLC:

high-performance liquid chromatography

PHA:

phenylhydracrylic acid

PA:

phenylacetic acid

HPA:

hyxdroxyphenylacetic acid

PMS:

phenazine methosulphate

PMA:

phenylmalonic acid

GSH:

glutathione

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Authors and Affiliations

  1. Division of Industrial Microbiology Department of Food Science, Agricultural University, De Dreijen 12, 6703 CT, Wageningen, The Netherlands

    W. J. J. van den Tweel, J. P. Smits & J. A. M. de Bont

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  1. W. J. J. van den Tweel
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  2. J. P. Smits
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  3. J. A. M. de Bont
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van den Tweel, W.J.J., Smits, J.P. & de Bont, J.A.M. Catabolism of dl-α-phenylhydracrylic, phenylacetic and 3- and 4-hydroxyphenylacetic acid via homogentisic acid in a Flavobacterium sp.. Arch. Microbiol. 149, 207–213 (1988). https://doi.org/10.1007/BF00422006

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  • DOI: https://doi.org/10.1007/BF00422006

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