The conversion of 23,24-dinor-chol-5-en-3β-ol into steroid hormones

Tait, A. D.

doi:10.1042/bj1280467

Cited by 27 publications

(3 citation statements)

References 8 publications

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“…This is particularly clear with the pig testis mitochondria. It is clear from these results and from earlier studies (Luttrell et al, 1972;Tait, 1972;Hochberg et al, 1974) that the cholesterol side-chain-cleavage system is capable of cleaving a wide variety of substrates with the formation of pregnenolone. One of the difficulties in interpreting these anid earlier results is clearly the heterogeneous nature ofthe preparations used.…”

Section: $ -E Ic)supporting

confidence: 58%

Oxidation of cholesterol and cholesterol analogues by mitochondrial preparations of steroid-hormone-producing tissue

Arthur

Blair

Boyd

et al. 1976

Biochemical Journal

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The rate of oxidation of cholesterol and its analogues to pregnenolone (3beta-hydroxypregn-5-en-20-one) by various mitochondrial preparations was measured. Sterols with the cholest-5-en-3beta-ol ring system and saturated side chains of different lengths were converted into pregnenolone rat rates similar to that of cholesterol. This marked lack of mitochondrial specificity towards the steroid side chains is in direct contrast with the rat liver microsomal cholesterol 7alpha-hydroxylase, which has a high specificity for the side chain. Steroids that retain the ring system, but contain hydroxyl groups at various points in the side chain, are converted into pregnenolone at rates three to eight times higher than in cholesterol. The results are discussed with reference to current ideas on the mechanism of the side-chain cleavage of cholesterol. The results are discussed with reference to current ideas on the mechanism of the side-chain cleavage of cholesterol.

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Section: $ -E Ic)supporting

confidence: 58%

Oxidation of cholesterol and cholesterol analogues by mitochondrial preparations of steroid-hormone-producing tissue

Arthur

Blair

Boyd

et al. 1976

Biochemical Journal

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“…6. In 1972, Tait [26] reported that an enzyme present in the microsomes from rat testes could in in vitro incubation convert 20-methyl-pregnen-5-en-3␤-ol into the C 19 -steroids, testosterone and androstenedione (Path A). In 1976, Hochberg et al [27] reported that testicular microsomes converted 20-deoxy-pregnenolone into testosterone (Path B).…”

Section: Does Cholesterol Serve As An In Situ Substrate For P-450 21 mentioning

confidence: 99%

“…6. Conversions using microsomes from rat testes A [26] and B [27]. then incubated for 2 h with the tritiated sterol.…”

Section: Some New Proposals For the Oxidative Processes Involved In Smentioning

confidence: 99%

Other conceivable renditions of some of the oxidative processes used in the biosynthesis of steroid hormones

Lieberman

Kaushik

2006

The Journal of Steroid Biochemistry and Molecular Biology

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Gas chromatographic and gas chromatographic/tandem mass spectrometric characterization of precursors on the sesterterpene pathway for steroid biosynthesis

Tait

Abbs

Teale³

et al. 1989

Biol. Mass Spectrom.

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An increasing amount of evidence is accumulating to support the proposal that steroidogenesis can occur by a sesterterpene pathway as well as the cholesterol pathway. Key intermediates on the sesterterpene pathway are 23,24-dinor-5-cholen-3 beta-ol (guneribol) and some of its metabolites, e.g. 23,24-dinor-4-cholen-3-one (guneribone). It has been reported that these intermediates are biosynthesized and converted to steroid hormones by a range of endocrine tissues in vitro. Monitoring the pentafluorobenzyloxime derivatives by negative ion chemical ionization mass spectrometry in the electron capture mode provided evidence for the presence of guneribone in extracts of bovine testicular and human adrenal tumour tissue. Complementary evidence was obtained from gas chromatographic/tandem mass spectrometric data generated on a triple-quadrupole instrument by monitoring daughter ions (in the multiple ion detection, MID mode) of the molecular anion of derivatized guneribone in both standards and tissue extracts. The present findings that sesterterpene pathway intermediates are present as endogenous compounds in tissue extracts, together with the previously reported radiochemical data, give further support to the sesterterpene pathway hypothesis.

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The conversion of 23,24-dinor-chol-5-en-3β-ol into steroid hormones

Cited by 27 publications

References 8 publications

Oxidation of cholesterol and cholesterol analogues by mitochondrial preparations of steroid-hormone-producing tissue

Oxidation of cholesterol and cholesterol analogues by mitochondrial preparations of steroid-hormone-producing tissue

Other conceivable renditions of some of the oxidative processes used in the biosynthesis of steroid hormones

Gas chromatographic and gas chromatographic/tandem mass spectrometric characterization of precursors on the sesterterpene pathway for steroid biosynthesis

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