Microbial Production of Ursodeoxycholic Acid from Lithocholic Acid by
            <i>Fusarium equiseti</i>
            M41

Sawada, Haruji; Kulprecha, Songsri; Nilubol, Naline; Yoshida, Takemi; Kinoshita, Shinichi; Taguchi, Hiroyasu

doi:10.1128/aem.44.6.1249-1252.1982

Cited by 34 publications

(14 citation statements)

References 12 publications

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“…Therefore, for the design of a biotransformation study involving hydrophobic substrates, it is critical to consider the adsorption capacity of each microorganism. From our experience in the screening of bile acid transformers (16,22), a high binding capacity for bile acids is a prerequisite for the high transformation of the substrate.…”

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confidence: 99%

“…In studying the biotransformation of steroidal compounds (13,(15)(16)(17)22), we found Fusarium equiseti M41 to transform lithocholic acid (LCA) into ursodeoxycholic acid (UDCA), a gallstone solubilizer that is effective in humans (20,24). We found that this fungus required a concentration of LCA higher than is necessary for it to be soluble in water for its efficient conversion to UDCA, and that insoluble LCA particles attached to the mycelia of F. equiseti M41.…”

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Adsorption of Lithocholic Acid to Fusarium equiseti M41 as an Essential Process in Its Conversion to Ursodeoxycholic Acid

Nihira

Nishino

Maehara

et al. 1988

Appl Environ Microbiol

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Fusarium equiseti M41 converts lithocholic acid to ursodeoxycholic acid. Adsorption of lithocholic acid particles to mycelia of F. equiseti M41 is essential in the conversion of lithocholic acid to ursodeoxycholic acid. Production of ursodeoxycholic acid was negligible when particles of lithocholic acid were absent. As the concentration of lithocholic acid particles increased, both the amount of mycelium-bound lithocholic acid and the production of ursodeoxycholic acid increased hyperbolically (K1/2 = 1.9 g/liter and K = 1.9 g/liter. A fluorescent lithocholic acid derivative was used to confirm that insoluble particles of litl;PcTolic

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Adsorption of Lithocholic Acid to Fusarium equiseti M41 as an Essential Process in Its Conversion to Ursodeoxycholic Acid

Nihira

Nishino

Maehara

et al. 1988

Appl Environ Microbiol

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“…Assay. Bile acid content was determined gas chromatographically after derivatization with hexafluoroisopropanol and trifluoroacetic anhydride (17) as described before (25), using cholic acid as an internal standard. The relative retension times of UDCA, LCA, and a by-product against cholic acid were 0.67, 0.29, and 0.89, respectively.…”

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“…In a previous paper (25) we reported the formation of UDCA, using one-step transformation from lithocholic acid (LCA; 3ot-hydroxy-5,B-cholanic acid), by Fusarium equiseti M41. In this paper we report the optimization of biotransformation of LCA into UDCA.…”

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Optimum conditions for ursodeoxycholic acid production from lithocholic acid by Fusarium equiseti M41

Kulprecha¹,

Ueda²,

Nihira³

et al. 1985

Appl Environ Microbiol

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Ursodeoxycholic acid dissolves cholesterol gallstones in humans. In the present study optimum conditions for ursodeoxycholic acid production by Fusarium equiseti M41 were studied. Resting mycelia of F. equiseti M41 showed maximum conversion at 28°C, pH 8.0, and dissolved oxygen tension of higher than 60% saturation. Monovalent cations, such as Na+, K+, and Rb+, stimulated the conversion rate more than twofold. In the presence of 0.5 M KCI, the initial uptake rate and equilibrium concentration of lithocholic acid (substrate) were enhanced by 5.7-and 1.7-fold, respectively. We confirmed that enzyme activity catalyzing 7fi-hydroxylation of lithocholic acid was induced by substrate lithocholic acid. The activity in the mycelium was controlled by dissolved oxygen tension during cultivation: with a dissolved oxygen tension of 15% and over, the activity peak appeared at 25 h of cultivation, whereas the peak was delayed to 34 and 50 h with 5 and 0% dissolved oxygen tension, respectively. After reaching the maximum, the 70i-hydroxylation activity in the mycelium declined rapidly at pH 7.0, but the decline was retarded by increasing the pH to 8.0. Several combinations of operations, such as pH shift (from pH 7 to 8), addition of 0.5 M KCI, and dissolved oxygen control, were applied to the production of ursodeoxycholic acid in a jar fermentor, and a much larger amount of ursodeoxycholic acid (1.2 g/liter) was produced within 96 h of cultivation.

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“…Research with steroid biotransformations by intestinal bacteria has emphasized the three major classes of steroids which pass through the GI tract; these are the bile acids (43,78,92,94,103), cholesterol (18,39,143,147), and steroid hormones (14,16,154). Although this review will almost exclusively deal with bacteria, it should be noted that protozoa and fungi can also play an important role in steroid biotransformations (21,60,121).…”

Section: Bacterial Transformations Of Steroids In the Gastrointestinamentioning

confidence: 99%

C-10(19) oxidation of vitamin D by anaerobic gastrointestinal bacteria

Gardner

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Importance and implications Bile Cholesterol Other biologically important steroids 28 Vitamin D Vitamin D Importance and implications Metabolism Biological activity Enterohepatic cycling of vitamin D Requirements and toxicity SECTION I. FACTORS AFFECTING THE PRODUCTION OF 5(E) 19-NOR-lO-KETO-VITAMIN D3 BY RUMEN BACTERIA 46 MATERIALS AND METHODS 49 General 49 Steroids 49 Enzymes 50 Extraction and Chromatography 50 Preparation of Media 51 Assay Conditions 52 iii Rumen Fluid Studies 52 Oxygen studies 53 Preincubation treatments Mixed Culture Studies Filtration Time study Glucose inhibition Isolation of Clostridium sp. Strain A264 Pure Culture Studies Glucose inhibition studies Cysteine Studies RESULTS Rumen Fluid Studies BHI Broth Culture Studies DISCUSSION 62 LITERATURE CITED SECTION II. THE BIOLOGICAL ASSESSMENT OF VITAMIN Dg METABOLITES PRODUCED BY RUMEN BACTERIA 80 Biological Evaluation Preparation "of Bacterial Culture Medium Isolation of Clostridium sp. Strain A264 Rumen Fluid Assay Conditions Extraction and Chromatography RESULTS 91

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Microbial Production of Ursodeoxycholic Acid from Lithocholic Acid by Fusarium equiseti M41

Abstract: A fungus identified as Fusarium equiseti was isolated from soil and found to carry out 7,3-hydroxylation of lithocholic acid to ursodeoxycholic acid (35% yield; 350 mg/liter) in 112 h.

Cited by 34 publications

References 12 publications

Adsorption of Lithocholic Acid to Fusarium equiseti M41 as an Essential Process in Its Conversion to Ursodeoxycholic Acid

Adsorption of Lithocholic Acid to Fusarium equiseti M41 as an Essential Process in Its Conversion to Ursodeoxycholic Acid

Optimum conditions for ursodeoxycholic acid production from lithocholic acid by Fusarium equiseti M41

C-10(19) oxidation of vitamin D by anaerobic gastrointestinal bacteria

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