Microbiological degradation of bile acids. Nitrogenous hexahydroindane derivatives formed from cholic acid by <i>Streptomyces rubescens</i>

Hayakawa, Shinya; Hashimoto, Shigeru; Onaka, Tadamasa

doi:10.1042/bj1600745

Cited by 12 publications

(23 citation statements)

References 10 publications

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“…This, and the NMR data in particular, indicated that the compound could be the 6-lactam compound (14B) [NMR,6 7.47 (1 H, broad s, disappears after D 2 0 exchange, NH), 4.77 (1 H, d of d, J2,2 Hz, C(6)H), 4.49 (1 H d of d, J2,2 Hz, C(7a)H), 1.02 (s, 7aPCH3). This structural derivation is supported by comparison with the spectral data published for the &lactam (14A) by Hayakawa et al (1976). In particular, compound (14A) is reported to have a Amax.…”

Section: Isolation Of the Intermediates Formed By M U I7 From Deoxysupporting

confidence: 62%

Steroid Catechol Degradation: Disecoandrostane Intermediates Accumulated by Pseudomonas Transposon Mutant Strains

Leppik¹

1989

Microbiology

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Eleven transposon mutant strains affected in bile acid catabolism were each found to form yellow, muconic-like intermediates from bile acids. To characterize these unstable intermediates, media from the growth of one of these mutants with deoxycholic acid was treated with ammonia, then the crude product was methylated with diazomethane. Four compounds were subsequently isolated; spectral evidence suggested that they were methyl 12 alpha-hydroxy-3-oxo-23,24-dinorchola-1,4-dien-22-oate, methyl 4-aza-12 beta-hydroxy-9(10)-secoandrosta-1,3,5-triene-9,17-dione-3-carboxyl ate, 4-aza-9 alpha, 12 beta-dihydroxy-9(10)-secoandrosta-1,3,5-trien-17-one-3- methyl carboxylate and 4 alpha-[3'-propionic acid]-5-amino-7 beta-hydroxy-7 alpha beta-methyl- 3a alpha, 4,7,7a-tetrahydro-1-indanone-delta-lactam. It is proposed that the mutants are blocked in the utilization of such muconic-like compounds as the 3,12 beta-dihydroxy-5,9,17-trioxo-4(5),9(10)- disecoandrostal (10),2-dien-4-oic acid formed from deoxycholic acid. A further mutant was examined, which converted deoxycholic acid to 12 alpha-hydroxyandrosta-1,4-dien-3,17-dione, but accumulated yellow products from steroids which lacked a 12 alpha-hydroxy function, such as chenodeoxycholic acid. The products from the latter acid were treated as above; spectral evidence suggested that the two compounds isolated were methyl 4-aza-7-hydroxy-9(10)-secoandrosta-1,3,5- triene-9,17-dione-3-carboxylate and 4 alpha-[1'alpha-hydroxy-3'-propionic acid]-5-amino-7a beta-methyl-3a alpha,4,7,7a-tetrahydro-1-indanone-delta-lactam.

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Section: Isolation Of the Intermediates Formed By M U I7 From Deoxysupporting

confidence: 62%

Steroid Catechol Degradation: Disecoandrostane Intermediates Accumulated by Pseudomonas Transposon Mutant Strains

Leppik¹

1989

Microbiology

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“…This suggests that the degradation of these bile acids with this organism also follows this 9,lO-seco-phenol pathway containing the 6a-, 701-or 12a-dehydroxylation discussed above and produces 46. S. rubescens converted cholic acid ( 1 ) into 46 and several enaminolactam derivatives, which were described as a general formula 50 in Scheme 6 and postulated to be formed from the corresponding 8-oxocarboxylic acids 37, 46 and 51, in addition to 5, 6, 7 and 8 in Scheme 1 (HAYAKAWA et al 1976b foniicd ti) t h i b organi 11. L must iiiention here the soinen hat peculiar biodegradability of iiiicroorganisnis 1% I ch can 1itiii.w cholic acid as a carbon source.…”

Section: Formation and Degradation Of Perhydroindane Derivativesmentioning

confidence: 99%

Microbial transformation of bile acids. A unified scheme for bile acid degradation, and hydroxylation of bile acids

Hayakawa

1982

J of Basic Microbiology

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Through the isolation and identification of a wide variety of degradation products formed from bile acids by microorganisms, a unified scheme for the complete degradation of bile acids to carbon dioxide and water has been proposed and discussed. The proposed degradative pathways mainly consist of the following steps: natural C24 3‐hydroxy bile acids → 3‐oxo bile acids → Δ4‐3‐oxo bile acids → → C16 or C18 perhydroindane derivative (at least in two ways) → → (4→)‐4‐methyl‐5‐oxo‐octanedioic acid (at least in three ways) → → CO2 and H2O. A microbial hydroxylation method for the preparation of bile acid samples was investigated which could be used as reference standards in the analysis of bile acids in biological materials and also as materials for studying the function of bile acids. The particular fungi, Curcularia lunata NRRL‐2380, Helicostylum piriforme ATTC‐8992 and Pestalotia foedans ATCC‐11817 effected the 1β‐, 11β‐, 12β‐, 15α‐ or 15β‐hydroxylation of certain bile acids and gave the following products: 1β,3α‐, 3α,12β‐ and 3α,15β‐dihydroxy‐5β‐cholan −24‐oic acids, 3α,12β,15α‐ and 3α,12β, 15β‐trihydroxy‐5β‐cholan‐24‐oic acids and 12β,15β‐dihydroxy‐3‐oxo‐5β‐cholan‐24‐oic acid from‐lithocholic acid; 1β,3α,12α‐ and 3α,12α,15β‐trihydroxy‐5β‐cholan‐24‐oic acids and 3α, 11β‐dihydroxy‐12‐oxo‐5β‐cholan‐24‐oic acid from deoxycholic acid; 3α, 7α, 12β‐trihydroxy‐5β‐cholan‐24‐oic acid 3α,7α,12β, 15α‐tetrahydroxy‐5β‐cholan‐24‐oic acid from chenodeoxycholic acid; 3α‐6α,12β‐ and 3α,6α, 15β‐trihydroxy‐5β‐cholan‐24‐oic acids from hyodeoxycholic acid; 3α, 7β, 12β trihydroxy‐5β‐cholan‐24‐oic acid from ursodeoxycholic acid; 3α,12β‐dihydroxy‐7‐oxo‐5β‐cholan‐24‐oic acid from 3α‐hydroxy‐7‐oxo‐5β‐cholan‐24‐oic acid. Some of these products were new compounds and their structures were determine.

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“…Secosteroids with novel molecular structures have also been obtained after the ring cleavage [14], [15]. Thus, microbial cleavage of steroid rings A-D has been reported to give unusual products that could not be synthesized by conventional chemical syntheses [16]. A sequential ring opening and modification of the steroid nucleus resulting in innovative products has been proposed by Hayakawa [17].…”

Section: Introductionmentioning

confidence: 97%

Transformation of chenodeoxycholic acid by thermophilic Geobacillus stearothermophilus

Afzal

Oommen

Al-Awadi

2011

Biotech and App Biochem

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We performed a series of experiments with Geobacillus stearothermophilus, a thermophile isolated from oil-contaminated soil in the Kuwaiti desert. The organism has a good potential for the transformation of a broad spectrum of organic molecules such as steroids, amino acids, and aromatic hydrocarbons. In the present study, we tested its potential for the transformation of a bile component, chenodeoxycholic acid (CDCA). Five transformed products, namely, cholic acid, methylcholate, methylchenodeoxycholate, 3α-hydroxy-7-oxo-5β-cholanic acid, and 7α-hydroxy-3-oxo-5β-cholanic acid, were the major transformation products catalyzed by G. stearothermophilus. Under aerobic conditions, no evidence of side chain degradation, ring cleavage, or dehydrogenation was found among the metabolites of CDCA. CDCA transformation by a thermophile is reported for the first time.

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

Cited by 12 publications

References 10 publications

Steroid Catechol Degradation: Disecoandrostane Intermediates Accumulated by Pseudomonas Transposon Mutant Strains

Steroid Catechol Degradation: Disecoandrostane Intermediates Accumulated by Pseudomonas Transposon Mutant Strains

Microbial transformation of bile acids. A unified scheme for bile acid degradation, and hydroxylation of bile acids

Transformation of chenodeoxycholic acid by thermophilic Geobacillus stearothermophilus

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