Literature DB >> 5378382

Microbiological degradation of bile acids. Ring A cleavage and 7alpha, 12alpha-dehydroxylation of cholic acid by Arthrobacter simplex.

S Hayakawa, Y Kanematsu, T Fujiwara.   

Abstract

The metabolism of cholic acid by Arthrobacter simplex was investigated. This organism effected both ring a cleavage and elimination of the hydroxyl groups at C-7 and C-12 and gave a new metabolite, (4R)-4-[4alpha-(2-carboxyethyl)-3aalpha-hexahydro-7abeta-methyl-5-oxoindan-1beta-yl]valeric acid, which was isolated and identified through its partial synthesis. A degradative pathway of cholic acid into this metabolite is tentatively proposed, and the possibility that the proposed pathway could be extended to the cholic acid degradation by other microorganisms besides A. simplex is discussed. The possibility that the observed reactions in vitro could occur during the metabolism of bile acids in vivo is considered.

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Year:  1969        PMID: 5378382      PMCID: PMC1185096          DOI: 10.1042/bj1150249

Source DB:  PubMed          Journal:  Biochem J        ISSN: 0264-6021            Impact factor:   3.857


  7 in total

1.  TRANSFORMATION OF CHOLIC ACID IN VITRO BY CORYNEBACTERIUM SIMPLEX. BILE ACIDS AND STEROIDS. 132.

Authors:  S HAYAKAWA; B SAMUELSSON
Journal:  J Biol Chem       Date:  1964-01       Impact factor: 5.157

2.  Microbiological degradation of cholic acid.

Authors:  S HAYAKAWA; T FUJII; Y SABURI; T EGUCHI
Journal:  Nature       Date:  1957-03-09       Impact factor: 49.962

3.  An alternative pathway for the degradation of cholic acid by micro-organisms.

Authors:  S HAYAKAWA; Y SABURI; K TAMAKI; H HOSHIJIMA
Journal:  Nature       Date:  1958-03-29       Impact factor: 49.962

4.  Studies on the microbiological degradation of steroid ring A.

Authors:  A W Coulter; P Talalay
Journal:  J Biol Chem       Date:  1968-06-25       Impact factor: 5.157

5.  Amino-acid conjugation in bacteria.

Authors:  S Hayakawa; T Fujiwara; H Tsuchikawa
Journal:  Nature       Date:  1968-09-14       Impact factor: 49.962

6.  In vivo metabolism of 3beta-acetoxychol-5-enoci-24-14C acid in the rat.

Authors:  F Nakada; R Oshio; S Sasaki; H Yamasaki; N Yamaga
Journal:  J Biochem       Date:  1968-10       Impact factor: 3.387

7.  New dehydroxylation reaction observed in the microbiological degradation pathway of cholic acid.

Authors:  S Hayakawa; Y Kanematsu; T Fujiwara
Journal:  Nature       Date:  1967-04-29       Impact factor: 49.962

  7 in total
  12 in total

1.  Bioconversion of Lithocholic Acid Under Anaerobic Conditions by Pseudomonas sp. Strain NCIB 10590.

Authors:  R W Owen; R F Bilton
Journal:  Appl Environ Microbiol       Date:  1984-09       Impact factor: 4.792

2.  Microbiological degradation of bile acids. The preparation of some hypothetical metabolites involved in cholic acid degradation.

Authors:  S Hayakawa; Y Kanematsu; T Fujiwara; H Kako
Journal:  Biochem J       Date:  1976-03-15       Impact factor: 3.857

3.  Microbiological degradation of bile acids. The preparation of hexahydroindane derivatives as substrates for studying cholic acid degradation.

Authors:  S Hayakawa; T Takata; T Fujiwara; S Hashimoto
Journal:  Biochem J       Date:  1977-06-15       Impact factor: 3.857

4.  Microbiological degradation of bile acids. Metabolites formed from 3-(3a alpha-hexahydro-7a beta-methyl-1,5-dioxoindan-4 alpha-yl) propionic acid by Streptomyces rubescens.

Authors:  S Hashimoto; S Hayakawa
Journal:  Biochem J       Date:  1977-06-15       Impact factor: 3.857

5.  Incubation of human fecal homogenates with 4-14-C-cholesterol.

Authors:  P D Wood; D Hatoff
Journal:  Lipids       Date:  1970-08       Impact factor: 1.880

6.  The metabolism of lithocholic acid and lithocholic acid-3-alpha-sulfate by human fecal bacteria.

Authors:  S P Borriello; R W Owen
Journal:  Lipids       Date:  1982-07       Impact factor: 1.880

7.  Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by Streptomyces rubescens.

Authors:  S Hayakawa; S Hashimoto; T Onaka
Journal:  Biochem J       Date:  1976-12-15       Impact factor: 3.857

8.  Microbiological degradation of bile acids. The conjugation of a certain cholic acid metabolite with amino acids in Corynebacterium equi.

Authors:  S Hayakawa; T Fujiwara; H Kako
Journal:  Biochem J       Date:  1976-12-15       Impact factor: 3.857

9.  Identification of 9α-hydroxy-17-oxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid in steroid degradation by Comamonas testosteroni TA441 and its conversion to the corresponding 6-en-5-oyl coenzyme A (CoA) involving open reading frame 28 (ORF28)- and ORF30-encoded acyl-CoA dehydrogenases.

Authors:  Masae Horinouchi; Toshiaki Hayashi; Hiroyuki Koshino; Michal Malon; Hiroshi Hirota; Toshiaki Kudo
Journal:  J Bacteriol       Date:  2014-08-04       Impact factor: 3.490

10.  Nucleotide sequence and regulation of a gene involved in bile acid 7-dehydroxylation by Eubacterium sp. strain VPI 12708.

Authors:  J P Coleman; W B White; M Lijewski; P B Hylemon
Journal:  J Bacteriol       Date:  1988-05       Impact factor: 3.490

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