Deoxycholic acid degradation by a pseudomonas sp: Phenolic and neutral products

Leppik, R A

doi:10.1016/s0040-4020(01)98940-9

Cited by 19 publications

(27 citation statements)

References 9 publications

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“…Intermediates involved in the degradation of deoxycholic acid with this organism are not isolated yet but at least three of them are probably 11, 12 and 12a-hydroxy-3-oxo-5/?-cholan-24-oic acid (13) as discussed later. This possibility is supported by the work of LEPPIK (1981a( , 1981b( ) and BILTON etal. (1981 who isolated and identified 11, 12, 13 and many other products formed from 2 by Pseudomonas spp.…”

Section: Side Chain Shortening and Slight Modification Of Ringmentioning

confidence: 65%

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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Section: Side Chain Shortening and Slight Modification Of Ringmentioning

confidence: 65%

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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“…The first report of such secosteroids was by Dodson & Muir (1958), who isolated the secophenol4A after fermentation of androst-4-ene-3,17-dione by a Pseudomonas sp. Similar secophenols have been isolated from other androstane substrates (Schubert et al, 1960;Wang & Sih, 1963), from progesterone (Schubert et al, 1961), and from bile acids (Leppik, 1981 ;Park, 1984).…”

Section: Discussionmentioning

confidence: 55%

“…The difference in the mass spectral patterns c 1 OH, 202N. (Leppik, 1981), and those that contain a 9-hydroxy function, such as compound (15) (Fig. 4), is striking, and is indicative of the strong influence that the 9-keto function has on the fragmentation pattern.…”

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

confidence: 96%

“…This results in the dehydrogenation of the A ring, and in side-chain removal, to produce the epimeric androstane compounds (2) and (3) (Leppik, 1983, and references therein). The B ring is then opened, to give initially the secophenol (4) (Leppik, 1981;Park, 1984), then the secocatechol (5) (Park et al, 1988). This is followed by removal of the A ring carbons (except C-5) as the next, and most degraded, pathway intermediate to have been reported is the &lactone of the indane acid (8) (Leppik, 1981).…”

Section: Introductionmentioning

confidence: 99%

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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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“…The mechanisms of degradation of these intermediates are still unclear. Meanwhile, the 6-1actones corresponding to the methylperhydroindan-5-one-4-a-propionates are often isolated amongst the diverse steroid catabolites from wild-type strains (Schubert et al 1961(Schubert et al , 1965Wang and Sih 1963;Hashimoto and Hayakawa 1977) and from mutants (Sch6mer et al 1978;Nakamatsu et al 1980;Leppik 1981;Ferreira et al 1984;Miclo et al 1986b).…”

Section: Introductionmentioning

confidence: 99%

Catabolism of methylperhydroindanedione propionate by Rhodococcus equi: evidence of a MEPHIP-reductase activity

Miclo¹,

Germain²

1990

Appl Microbiol Biotechnol

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Catabolism of methylperhydroindanedione proprionate (MEPHIP), an intermediate in steroid nucleus degradation, begins in Rhodococcus equi by reduction of the 5-keto group to a 5a-hydroxy group. This reaction is carried out in two steps: the first is an activation of MEPHIP by coenzyme A (CoA) and ATP; the second is the reduced nicotine adenine dinucleotide phosphate (NADPH) dependent reduction of the resultant MEPHIP-CoA by a dehydrogenase. This ME-PHIP-reductase activity appears only after induction by steroids or by MEPHIP itself.

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Deoxycholic acid degradation by a pseudomonas sp: Phenolic and neutral products

Cited by 19 publications

References 9 publications

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

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

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

Catabolism of methylperhydroindanedione propionate by Rhodococcus equi: evidence of a MEPHIP-reductase activity

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