16-不饱和C19 3-氧代类固醇作为公猪睾丸中的代谢中间体。
16-unsaturated C 19 3-oxo steroids as metabolic intermediates in boar testis.
作者信息
Brophy P J, Gower B D
出版信息
Biochem J. 1972 Jul;128(4):945-52. doi: 10.1042/bj1280945.
Abstract
- The formation of the two 16-unsaturated alcohols 5alpha-androst-16-en-3alpha-ol and 5alpha-androst-16-en-3beta-ol from [5alpha-(3)H]5alpha-androst-16-en-3-one has been demonstrated in boar testis homogenates. 2. The optimum yield (23%) of the 3alpha-alcohol was obtained in the presence of NADPH, whereas that for the 3beta-alcohol (74%) was obtained when NADH was the added cofactor. 3. The two alcohols were not interconvertible. 4. Prolonged storage of boar testis tissue at -20 degrees C abolished the ability to form all androst-16-enes except androsta-4,16-dien-3-one from [4-(14)C]progesterone. 5. The production of 5alpha-androst-16-en-3-one and the two alcohols from [7alpha-(3)H]androsta-4,16-dien-3-one only occurred when fresh tissue was used, whereas reduction of [5alpha-(3)H]5alpha-androst-16-en-3-one was unaffected by storage of testis at -20 degrees C. 6. NADPH was the preferred cofactor for the reduction of androsta-4,16-dien-3-one. 7. The previously established conversion of androsta-5,16-dien-3beta-ol into androsta-4,16-dien-3-one was shown to be reversible, NADH and NADPH being equally effective cofactors. 8. Pathways of biosynthesis of 5alpha-androst-16-en-3alpha- and 3beta-ols, with the C(19) 3-oxo steroids as intermediates, are presented.
摘要
- 在公猪睾丸匀浆中已证实由[5α-(3)H]5α-雄甾-16-烯-3-酮形成两种16-不饱和醇，即5α-雄甾-16-烯-3α-醇和5α-雄甾-16-烯-3β-醇。2. 在NADPH存在下，3α-醇的最佳产率（23%）得以实现，而当添加NADH作为辅因子时，3β-醇的最佳产率（74%）得以实现。3. 这两种醇不能相互转化。4. 将公猪睾丸组织在-20℃下长期保存，消除了由[4-(14)C]孕酮形成除雄甾-4,16-二烯-3-酮之外的所有雄甾-16-烯的能力。5. 仅当使用新鲜组织时，才会由[7α-(3)H]雄甾-4,16-二烯-3-酮产生5α-雄甾-16-烯-3-酮和这两种醇，而睾丸在-20℃下保存并不影响[5α-(3)H]5α-雄甾-16-烯-3-酮的还原。6. NADPH是还原雄甾-4,16-二烯-3-酮的首选辅因子。7. 先前确定的雄甾-5,16-二烯-3β-醇向雄甾-4,16-二烯-3-酮的转化被证明是可逆的，NADH和NADPH作为辅因子同样有效。8. 提出了以C(19) 3-氧代类固醇为中间体的5α-雄甾-16-烯-3α-醇和3β-醇的生物合成途径。
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本文引用的文献
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J Endocrinol. 1961 Dec;23:253-60. doi: 10.1677/joe.0.0230253.
2
Studies on the biosynthesis of 16-dehydro steroids. The metabolism of [4-14C]pregnenolone by boar adrenal and testis tissue in vitro.16-脱氢甾体生物合成的研究。[4-¹⁴C]孕烯醇酮在体外经公猪肾上腺和睾丸组织的代谢。
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Application of thin-layer chromatographic techniques to the separation of delta-16-C-19-steroids and related compounds.薄层色谱技术在δ-16-C-19-甾体及相关化合物分离中的应用。
Anal Biochem. 1967 Jul;20(1):77-85. doi: 10.1016/0003-2697(67)90267-9.
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Androgen steroids associated with boar odour as an aid to the detection of oestrus in pig artificial insemination.与公猪异味相关的雄激素类固醇作为猪人工授精中检测发情的辅助手段。
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