二苯并[a,h]蒽（±）反式-1,2-二氢二醇和屈（±）反式-3,4-二氢二醇向邻位二氢二醇环氧化物的代谢转化。
Metabolic conversion of dibenz[a,h]anthracene (+/-)trans-1,2-dihydrodiol and chrysene (+/-)trans-3,4-dihydrodiol to vicinal dihydrodiol epoxides.
作者信息
Chou M W, Fu P P, Yang S K
出版信息
Proc Natl Acad Sci U S A. 1981 Jul;78(7):4270-3. doi: 10.1073/pnas.78.7.4270.
Abstract
The hydroxyl groups of dibenz[a,h]anthracene trans-1,2-dihydrodiol and chrysene trans-3,4-dihydrodiol are known to be predominantly in quasi-axial conformations. These dihydrodiols were metabolized by liver microsomes from 3-methylcholanthrene-pretreated rats to form 1,2,3,4-tetrahydrotetrols as the major products. The major metabolites of the dihydrodiols were isolated by reversed-phase high-performance liquid chromatography and identified by ultraviolet--visible absorption and mass spectral analyses. The results indicate that axial hydroxyl groups of dibenz[a,h]anthracene trans-1,2-dihydrodiol and of chrysene trans-3,4-dihydrodiol do not direct metabolism away from their respective vicinal double bond.
摘要
已知二苯并[a,h]蒽反式-1,2-二氢二醇和屈反式-3,4-二氢二醇的羟基主要处于准轴向构象。这些二氢二醇由经3-甲基胆蒽预处理大鼠的肝微粒体代谢，形成1,2,3,4-四氢四醇作为主要产物。通过反相高效液相色谱法分离二氢二醇的主要代谢产物，并通过紫外-可见吸收和质谱分析进行鉴定。结果表明，二苯并[a,h]蒽反式-1,2-二氢二醇和屈反式-3,4-二氢二醇的轴向羟基不会使代谢偏离其各自的邻位双键。
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1
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J Biol Chem. 1951 Nov;193(1):265-75.
2
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3
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Biochem Biophys Res Commun. 1981 Feb 27;98(4):961-9. doi: 10.1016/0006-291x(81)91204-3.
4
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Chem Biol Interact. 1980 Feb;29(2):169-88. doi: 10.1016/0009-2797(80)90031-9.
5
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6
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FEBS Lett. 1974 Oct 1;47(1):34-8. doi: 10.1016/0014-5793(74)80420-5.
7
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8
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9
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10
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