Cholesterol oxidases: Properties and applications

Smith, Andrew G.; Brooks, C. J. W.

doi:10.1016/0022-4731(76)90071-6

Cited by 94 publications

(16 citation statements)

References 50 publications

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“…Other methods used to prepare 1 from cholesterol include the use of trifluoromethanesulfonic anhydride/dlmethyl sulfoxide, which gave 1 in 51% yield (21), and trifluoroacetic acid/dimethyl sulfoxide, which gave As-3-one (2) and A4-3-one (1) a 2:1 ratio (22). In addition, the conversion of cholesterol to 1 can be achieved using cholesterol oxidase derived from micra bial sources (2,23).…”

Section: Resultsmentioning

confidence: 99%

A facile chemical synthesis of cholest‐4‐en‐3‐one. Carbon‐13 nuclear magnetic resonance spectral properties of cholest‐4‐en‐3‐one and cholest‐5‐en‐3‐one

Parish

Honda

Chitrakorn

et al. 1991

Lipids

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This paper presents a simplified method for the chemical synthesis of cholest‐4‐en‐3‐one, which is a naturally occurring steroid and a salient intermediate in steroid chemistry. Pyridinium chlorochromate (PCC) in refluxing benzene has been found to be an effective and convenient reagent for the oxidation and concomitant isomerization of cholest‐5‐en‐3β‐ol (cholesterol) to cholest‐4‐en‐3‐one in high yield. Also described are the carbon‐13 nuclear magnetic resonance spectral properties of cholest‐4‐en‐3‐one and of the isolated reaction intermediate cholest‐5‐en‐3‐one.

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Section: Resultsmentioning

confidence: 99%

A facile chemical synthesis of cholest‐4‐en‐3‐one. Carbon‐13 nuclear magnetic resonance spectral properties of cholest‐4‐en‐3‐one and cholest‐5‐en‐3‐one

Parish

Honda

Chitrakorn

et al. 1991

Lipids

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“…The radioactive tissue lipids of cecum and colon (<2% of total radioactivity) consisted about half of coprositostanol. This metabolite was identified by TLC and GLC as well as by its poor conversion to the corresponding 3-oxo steroids using cholesterol oxidase (28,29).…”

Section: Resultsmentioning

confidence: 99%

Metabolism of sitosteryl β‐D‐glucoside and its nutritional effects in rats

Weber¹

1988

Lipids

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[4-14C]Sitosteryl beta-D-glucoside, intragastrically administered to rats, was not absorbed by the intestinal mucosa. At three hr after the application, radioactivity was concentrated almost exclusively in the digesta of stomach, small intestine as well as cecum and colon, whereas only low proportions of radioactively labeled compounds were found in the various tissues of the gastrointestinal tract. Minor proportions of labeled metabolites of [4-14C]sitosteryl beta-D-glucoside, such as sitosterol and sitosteryl esters, were formed in the small intestine in vivo and in slices of small intestine in vitro. In the tissues of cecum and colon as well as the digesta derived from them, high proportions of labeled coprositostanol, i.e. 24 alpha-ethyl-5 beta-cholestan-3 beta-ol, that obviously had been formed by bacterial degradation of the substrate were detected. The feeding of sitosteryl beta-D-glucoside (0.5 g/kg body weight X day) over a period of four weeks did not alter significantly body weights or organ weights of rats. Analyses of steryl lipids of the various organs and tissues confirmed the findings obtained with the radioactive substrate: neither sitosteryl beta-D-glucoside nor sitosterol or sitosteryl esters derived therefrom had been transported in appreciable amounts to organs and tissues outside the alimentary canal during the feeding period. Minor proportions of unmetabolized sitosteryl beta-D-glucoside were detected in the tissues of stomach and intestine, whereas large proportions of the substrate were found in feces of rats that had received the sitosteryl beta-D-glucoside-containing diet; coprositostanol was found in feces of these animals in high proportions as well.(ABSTRACT TRUNCATED AT 250 WORDS)

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Section: Introductionmentioning

confidence: 99%

“…The bacterial degradation of cholesterol has been known to occur by a cholesterol oxidase (cholesterol : oxygen oxidoreductase, EC 1.1.3.6), the enzyme which catalyses the oxidation of cholesterol to 4-cholesten-3-one, along with the reduction of oxygen to hydrogen peroxide (Smith and Brooks 1976). A variety of other micro-organisms producing cholesterol oxidase has also been reported, including Brevibacterium (Uwajima et al 1974), Corynebacterium (Shirokano et al 1977), Pseudomonas (Aono et al 1994), Rhodococcus (Watanabe et al 1986;Kreit et al 1994;Sojo et al 1997), Schizophyllum (Fukuyama and Miyake 1979) and Streptomyces spp.…”

Section: Introductionmentioning

confidence: 99%

Degradation of cholesterol by Bacillus subtilis SFF34 isolated from Korean traditional fermented flatfish

Kim

Rhee

Park

2002

Lett Appl Microbiol

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Aims: To examine cholesterol degradation by Bacillus subtilis SFF34. Methods and Results: Cholesterol degradation and cholesterol oxidase production by B. subtilis SFF34 were investigated in a medium containing 0AE2% cholesterol. In addition, the oxidized product of cholesterol by the purified cholesterol oxidase was detected using a gas chromatograph. Cholesterol oxidase production reached its maximal level (3AE14 U ml )1 ) after 24 h of incubation in the cholesterol medium. The residual cholesterol content reduced to 0AE98 mg g )1 after 60 h of cultivation in the cholesterol medium. Two cholesterol oxidases were purified from the culture supernatant fluid and their reaction product against cholesterol was identified as 4-cholesten-3-one. Conclusions: B. subtilis SFF34 degraded cholesterol and produced a high level of extracellular cholesterol oxidase. Significance and Impact of the Study: Bacillus subtilis will be very useful for the reduction of cholesterol in many fermented foods and as a source of cholesterol oxidase.

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Cholesterol oxidases: Properties and applications

Cited by 94 publications

References 50 publications

A facile chemical synthesis of cholest‐4‐en‐3‐one. Carbon‐13 nuclear magnetic resonance spectral properties of cholest‐4‐en‐3‐one and cholest‐5‐en‐3‐one

A facile chemical synthesis of cholest‐4‐en‐3‐one. Carbon‐13 nuclear magnetic resonance spectral properties of cholest‐4‐en‐3‐one and cholest‐5‐en‐3‐one

Metabolism of sitosteryl β‐D‐glucoside and its nutritional effects in rats

Degradation of cholesterol by Bacillus subtilis SFF34 isolated from Korean traditional fermented flatfish

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