Skip to main content
NCBI home page
Journal of Bacteriology logoLink to Journal of Bacteriology
. 1975 Jun;122(3):866–873. doi: 10.1128/jb.122.3.866-873.1975

Microbial metabolism of phenolic amines: degradation of dl-synephrine by an unidentified arthrobacter.

N A Devi, R K Kutty, V N Vasantharajan, P V Subba RAO
PMCID: PMC246136  PMID: 1150621

Abstract

Microorganisms capable of degrading dl-synephrine were isolated from soil of Citrus gardens by enrichment culture, with dl-synephrine as the sole source of carbon and nitrogen. An organism which appears to be an arthrobacter, but which cannot be identified with any of the presently recognized species was predominant in these isolates. It was found to metabolize synephrine by a pathway involving p-hydroxyphenylacetaldehyde, p-hydroxyphenylacetic acid, and 3,4-dihydroxyphenylacetic acid as intermediates. Some of the enzymes of this pathway were demonstrated in cell-free extracts. An aromatic oxygenase, which could also be readily obtained in a cell-free system, was found to degrade 3,4-dihydroxyphenylacetic acid by meta cleavage.

Full text

PDF
866

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. ADACHI K., TAKEDA Y., SENOH S., KITA H. METABOLISM OF P-HYDROXYPHENYLACETIC ACID IN PSEUDOMONAS OVALIS. Biochim Biophys Acta. 1964 Dec 9;93:483–493. doi: 10.1016/0304-4165(64)90332-0. [DOI] [PubMed] [Google Scholar]
  2. AXELROD J. Enzymatic formations of adrenaline and other catechols from monophenols. Science. 1963 May 3;140(3566):499–500. doi: 10.1126/science.140.3566.499. [DOI] [PubMed] [Google Scholar]
  3. Adachi T., Murooka Y., Harada T. Derepression of arylsulfatase synthesis in Aerobacter aerogenes by tyramine. J Bacteriol. 1973 Oct;116(1):19–24. doi: 10.1128/jb.116.1.19-24.1973. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Blakley E. R., Halvorson H., Kurz W. The microbial production and some characteristics of delta-carboxymethyl-alpha-hydroxymuconic semialdehyde. Can J Microbiol. 1967 Feb;13(2):159–165. doi: 10.1139/m67-022. [DOI] [PubMed] [Google Scholar]
  5. Conn H. J., Dimmick I. Soil Bacteria Similar in Morphology to Mycobacterium and Corynebacterium. J Bacteriol. 1947 Sep;54(3):291–303. doi: 10.1128/jb.54.3.291-303.1947. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. DAGLEY S., WOOD J. M. OXIDATION OF PHENYLACETIC ACID BY A PSEUDOMONAS. Biochim Biophys Acta. 1965 May 18;99:383–385. doi: 10.1016/s0926-6593(65)80140-0. [DOI] [PubMed] [Google Scholar]
  7. LEEPER L. C., WEISSBACH H., UDENFRIEND S. Studies on the metabolism of norepinephrine, epinephrine and their o-methyl analogs by partially purified enzyme preparations. Arch Biochem Biophys. 1958 Oct;77(2):417–427. doi: 10.1016/0003-9861(58)90089-4. [DOI] [PubMed] [Google Scholar]
  8. PISANO J. J., OATES J. A., Jr, KARMEN A., SJOERDSMA A., UDENFRIEND S. Identification of p-hydroxy-alpha-(methylaminomethyl) benzyl alcohol (synephrine) in human urine. J Biol Chem. 1961 Mar;236:898–901. [PubMed] [Google Scholar]
  9. Robbins J. H. Preparation and properties of p-hydroxyphenylacetaldehyde and 3-methoxy-4-hydroxyphenylacetaldehyde. Arch Biochem Biophys. 1966 Jun;114(3):576–584. doi: 10.1016/0003-9861(66)90382-1. [DOI] [PubMed] [Google Scholar]
  10. SENTHESHANMUGANATHAN S., ELSDEN S. R. The mechanism of the formation of tyrosol by Saccharomyces cerevisiae. Biochem J. 1958 Jun;69(2):210–218. doi: 10.1042/bj0690210. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. STEWART I., WHEATON T. A. I-OCTOPAMINE IN CITRUS: ISOLATION AND IDENTIFICATION. Science. 1964 Jul 3;145(3627):60–61. doi: 10.1126/science.145.3627.60. [DOI] [PubMed] [Google Scholar]
  12. Sparnins V. L., Chapman P. J., Dagley S. Bacterial degradation of 4-hydroxyphenylacetic acid and homoprotocatechuic acid. J Bacteriol. 1974 Oct;120(1):159–167. doi: 10.1128/jb.120.1.159-167.1974. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Tate R. L., Ensign J. C. A new species of Arthrobacter which degrades picolinic acid. Can J Microbiol. 1974 May;20(5):691–694. doi: 10.1139/m74-105. [DOI] [PubMed] [Google Scholar]
  14. Wheaton T. A., Stewart I. Quantitative analysis of phenolic amines using ion-exchange chromatography. Anal Biochem. 1965 Sep;12(3):585–592. doi: 10.1016/0003-2697(65)90226-5. [DOI] [PubMed] [Google Scholar]
  15. Wheaton T. A., Stewart I. The distribution of tyramine, N-methyltyramine, hordenine, octopamine, and synephrine in higher plants. Lloydia. 1970 Jun;33(2):244–254. [PubMed] [Google Scholar]

Articles from Journal of Bacteriology are provided here courtesy of American Society for Microbiology (ASM)

RESOURCES