Microsomal dehydrogenation of cis- and trans-acenaphthene-1,2-diol to acenaphthenequinone

Drummond, Elizabeth C.; Hopkins, R. P.

doi:10.1042/bj1130013pa

Cited by 24 publications

(8 citation statements)

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“…The existing literature on bacterial and mammalian metabolism of acenaphthene indicates the formation of metabolites 1-acenaphthenol, 1-acenaphthenone, acenaphthene-cis-1,2diol, 2-hydroxyacenaphthenone, and acenaphthenequinone (9,11,15,16,26,27). The oxidation of acenaphthene by Beijeinckia sp.…”

Section: -mentioning

confidence: 99%

Fungal metabolism of acenaphthene by Cunninghamella elegans

Pothuluri

Freeman

Evans

et al. 1992

Appl Environ Microbiol

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The filamentous fungus Cunninghamella elegans ATCC 36112 metabolized within 72 h of incubation approximately 64% of the [1,8-14Clacenaphthene added. The radioactive metabolites were extracted with ethyl acetate and separated by thin-layer chromatography and reversed-phase high-performance liquid chromatography. Seven metabolites were identified by 1H nuclear magnetic resonance, UV, and mass spectral techniques as 6-hydroxyacenaphthenone (24.8%), 1,2-acenaphthenedione (19.9%), trans-1,2-dihydroxyacenaphthene (10.3%), 1,5-dihydroxyacenaphthene (2.7%), 1-acenaphthenol (2.4%), 1-acenaphthenone (2.1%), and cis-1,2dihydroxyacenaphthene (1.8%). Parallel experiments with rat liver microsomes indicated that the major metabolite formed from acenaphthene by rat liver microsomes was l-acenaphthenone. The fungal metabolism of acenaphthene was similar to bacterial and mammalian metabolism, since the primary site of enzymatic attack was on the two carbons of the five-member ring.

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Section: -mentioning

confidence: 99%

Fungal metabolism of acenaphthene by Cunninghamella elegans

Pothuluri

Freeman

Evans

et al. 1992

Appl Environ Microbiol

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“…The dehydrogenation of ci8-and tran8-acenaphthene-1,2-diol to acenaphthenequinone by a rat liver microsomal preparation was demonstrated by Drummond & Hopkins (1969). Ayengar, Hayaishi, Nakajima & Tomida (1959) partially purified an enzyme (catechol reductase, EC 1.3.1.5) from acetone-dried rabbit liver powder that dehydrogenates tranm-1,2-dihydrobenzene-1,2-diol to 1,2-dihydroxybenzene in the presence of NADP+, and a similar reaction would be involved in the oxidation of the acenaphthenediols to acenaphthenequinone if 1,2-dihydroxyacenaphthylene were the initial dehydrogenation product.…”

Section: 2-diol By Soluble Preparations From Ratmentioning

confidence: 99%

Oxidation of cis- and trans-acenaphthene-1,2-diol by soluble preparations from rat liver

Drummond¹,

Callaghan²,

Hopkins³

1971

Biochemical Journal

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For the past 2 years an on-line computer has been used for hospital biochemistry. Currently the system covers 80% of the work load of the laboratory (250000tests/annum).Standard AutoAnalyzers are used as basic analytical instruments and these are coupled to a PDP 8/S computer. The system collects data simultaneously from 12 test channels fed from six sample channels. Input of command instructions, the collection and processing of data and the output of results occur as time-shared processes. Results are identified by specimen laboratory accession number entered into the system manually. Each test channel is calibrated in terms of a third-order polynomial expressing the assay value as a function of the peak readings. Correction is applied for calibration drift and specimen interaction. Factors that were considered in the design ofthe system and the main features of the program are presented and discussed. COMMUNICATIONSOxidation of cis-and trans-Acenaphthene- 1,2-diol by Soluble Preparations from RatLiver By ELIZABETH C. DRUMMOND, P. CALLAGHAN andThe dehydrogenation of ci8-and tran8-acenaphthene-1,2-diol to acenaphthenequinone by a rat liver microsomal preparation was demonstrated by Drummond & Hopkins (1969). Ayengar, Hayaishi, Nakajima & Tomida (1959) partially purified an enzyme (catechol reductase, EC 1.3.1.5) from acetone-dried rabbit liver powder that dehydrogenates tranm-1,2-dihydrobenzene-1,2-diol to 1,2-dihydroxybenzene in the presence of NADP+, and a similar reaction would be involved in the oxidation of the acenaphthenediols to acenaphthenequinone if 1,2-dihydroxyacenaphthylene were the initial dehydrogenation product.In the present work a preparation was obtained from acetone-dried rat liver powder that dehydrogenates trans-acenaphthene-1,2-diol in the presence of NADP+. The preparation was assayed by following the increase in extinction at 340nm due to the diol oxidation product and NADPH in 50mM-tris-HCl, pH9.0, at 37°C. The preparation was made by chromatographing the 100 0OOg supernatant of a suspension of the acetone-dried powder in 0.15M-potassium chloride on Sephadex G-25 equilibrated with lOmM-tris-HCl, pH8.0. This removes endogenous cofactor-reducing activity. The protein eluate was further chromatographed on DEAE-cellulose equilibrated in the same buffer, the column being eluted with a sodium chloride gradient. A fraction was obtained with nine times the specific activity of the Sephadex G-25 eluate. This preparation differed from the microsomal system in that it catalysed the oxidation of trans-acenaphthene-1,2-diol more readily than that of the 08-isomer, and required NADP+, and not NAD+, as cofactor. A preparation with these properties was also obtained from the 1000OOg supernatant of a homogenate of rat liver. An almost identical protein elution profile was obtained from the DEAE-cellulose column, and a similar degree of purification was achieved.After incubation of tran8-acenaphthene-1,2-diol and NADP+ at 370C with a preparation of the soluble enzyme at pH 9.0 for 2h, acenaphthenequinon...

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“…1, U.K. After the administration of acenaphthene, acenaphthylene and cisand trans-acenaphthene-1,2diol to rats, 1,8-naphthalic acid was isolated, as its anhydride, from the acidified urine of the dosed animals (Chang & Young, 1943;Hopkins, Brooks & Young, 1962;Hopkins & Young, 1966). Following the suggestion of Hopkins (1968) that oxidation of the acenaphthene-1,2-diols to 1,8-naphthalic acid might involve an initial dehydrogenation step, acenaphthenequinone was isolated from a microsomal incubation of the acenaphthene-1,2-diols in the presence of NAD+ (Drummond & Hopkins, 1969). Drummond, Callaghan & Hopkins (1971) have demonstrated that there are at least two systems in rat liver that dehydrogenate acenaphthene-1,2-diol, one in the microsomal fraction and another in the soluble fraction.…”

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confidence: 99%