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全反式视黄酰β-葡萄糖醛酸苷的化学合成。

Chemical synthesis of all-trans retinoyl beta-glucuronide.

作者信息

Barua A B, Olson J A

出版信息

J Lipid Res. 1985 Oct;26(10):1277-82.

PMID:3906006
Abstract

All-trans retinoyl fluoride reacts with the 3,6-lactone of glucuronic acid in slightly alkaline solution to give the lactone of retinoyl beta-glucuronide, along with other retinoyl glucurono-lactones, in about 60% yield. Hydrolysis of the lactone with very dilute alkali gives the free acid, retinoyl beta-glucuronide, in about 80% yield. Pure all-trans retinoyl beta-glucuronide (overall yield: 20-25%) was obtained free from other isomeric and anomeric forms by reverse-phase high pressure liquid chromatography. Retinoyl beta-glucuronide was characterized by UV-visible, infrared, and 1H-NMR spectra, by elementary analysis, by mass spectra, and by its susceptibility to hydrolysis by bacterial beta-glucuronidase.

摘要

全反式视黄酰氟在微碱性溶液中与葡萄糖醛酸的3,6-内酯反应,生成视黄酰β-葡萄糖醛酸内酯以及其他视黄酰葡萄糖醛酸内酯,产率约为60%。用极稀的碱水解内酯,得到游离酸视黄酰β-葡萄糖醛酸,产率约为80%。通过反相高压液相色谱法得到了不含其他异构体和异头物形式的纯全反式视黄酰β-葡萄糖醛酸(总产率:20 - 25%)。视黄酰β-葡萄糖醛酸通过紫外可见光谱、红外光谱、1H - NMR光谱、元素分析、质谱以及其对细菌β-葡萄糖醛酸酶水解的敏感性进行表征。

相似文献

1
Chemical synthesis of all-trans retinoyl beta-glucuronide.全反式视黄酰β-葡萄糖醛酸苷的化学合成。
J Lipid Res. 1985 Oct;26(10):1277-82.
2
Preparation, characterization, biological activity and metabolism of all-trans retinoyl fluoride.全反式视黄酰氟的制备、表征、生物活性及代谢
Biochim Biophys Acta. 1983 Jun 9;757(3):288-95. doi: 10.1016/0304-4165(83)90053-3.
3
Repeated intravenous doses of all-trans-retinoyl beta-D-glucuronide is not effective in the treatment of bacterial bronchopneumonia in lambs but is devoid of gross and acute toxicity.
Med Sci Monit. 2002 Sep;8(9):BR345-53.
4
Characterization of retinoyl beta-glucuronide as a minor metabolite of retinoic acid in bile.视黄酰β-葡萄糖醛酸苷作为胆汁中视黄酸的一种次要代谢产物的特性研究。
Proc Natl Acad Sci U S A. 1980 Jun;77(6):3230-3. doi: 10.1073/pnas.77.6.3230.
5
Chemical synthesis and growth-promoting activity of all-trans-retinyl beta-D-glucuronide.全反式视黄醇β-D-葡萄糖醛酸苷的化学合成及促生长活性
Biochem J. 1987 May 15;244(1):231-4. doi: 10.1042/bj2440231.
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Origin of some derivatives of retinoic acid found in rat bile.大鼠胆汁中发现的一些视黄酸衍生物的来源。
J Lipid Res. 1968 Sep;9(5):580-6.
7
Biosynthesis of retinoyl-beta-glucuronide, a biologically active metabolite of all-trans-retinoic acid.视黄酰-β-葡萄糖醛酸苷的生物合成,全反式维甲酸的一种生物活性代谢产物。
Arch Biochem Biophys. 1986 Jan;244(1):179-86. doi: 10.1016/0003-9861(86)90107-4.
8
Chemical synthesis of all-trans-[11-3H]retinoyl beta-glucuronide and its metabolism in rats in vivo.全反式-[11-³H]视黄酰β-葡萄糖醛酸苷的化学合成及其在大鼠体内的代谢
Biochem J. 1989 Oct 15;263(2):403-9. doi: 10.1042/bj2630403.
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13-cis retinoyl-beta-glucuronide in lacrimal gland fluid of rabbits treated with 13-cis retinoic acid.13-顺式视黄酸处理的兔泪腺液中的13-顺式视黄酰-β-葡萄糖醛酸苷
J Ocul Pharmacol. 1990 Winter;6(4):321-7. doi: 10.1089/jop.1990.6.321.
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Retinoyl beta-glucuronide: an endogenous compound of human blood.视黄酰β-葡萄糖醛酸苷:一种人体血液中的内源性化合物。
Am J Clin Nutr. 1986 Apr;43(4):481-5. doi: 10.1093/ajcn/43.4.481.

引用本文的文献

1
All-trans-retinoyl beta-glucuronide: new procedure for chemical synthesis and its metabolism in vitamin A-deficient rats.全反式视黄酰β-葡萄糖醛酸苷:化学合成新方法及其在维生素A缺乏大鼠体内的代谢
Biochem J. 1996 Feb 15;314 ( Pt 1)(Pt 1):249-52. doi: 10.1042/bj3140249.
2
Chemical synthesis and growth-promoting activity of all-trans-retinyl beta-D-glucuronide.全反式视黄醇β-D-葡萄糖醛酸苷的化学合成及促生长活性
Biochem J. 1987 May 15;244(1):231-4. doi: 10.1042/bj2440231.
3
Induction of differentiation of human promyelocytic leukemia cell line HL-60 by retinoyl glucuronide, a biologically active metabolite of vitamin A.
视黄醇葡萄糖醛酸酯(维生素A的一种生物活性代谢产物)诱导人早幼粒细胞白血病细胞系HL-60分化
Proc Natl Acad Sci U S A. 1987 Apr;84(8):2208-12. doi: 10.1073/pnas.84.8.2208.
4
Synthesis and metabolism of all-trans-[11-3H]retinyl beta-glucuronide in rats in vivo.大鼠体内全反式-[11-³H]视黄醇β-葡萄糖醛酸苷的合成与代谢
Biochem J. 1988 Jun 1;252(2):415-20. doi: 10.1042/bj2520415.
5
Chemical synthesis of all-trans-[11-3H]retinoyl beta-glucuronide and its metabolism in rats in vivo.全反式-[11-³H]视黄酰β-葡萄糖醛酸苷的化学合成及其在大鼠体内的代谢
Biochem J. 1989 Oct 15;263(2):403-9. doi: 10.1042/bj2630403.
6
Metabolism in vivo of all-trans-[11-3H]retinoic acid after an oral dose in rats. Characterization of retinoyl beta-glucuronide in the blood and other tissues.大鼠口服剂量全反式-[11-³H]视黄酸后的体内代谢。血液及其他组织中视黄酰β-葡萄糖醛酸苷的特性。
Biochem J. 1991 Jul 15;277 ( Pt 2)(Pt 2):527-31. doi: 10.1042/bj2770527.