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大鼠胆汁中发现的一些视黄酸衍生物的来源。

Origin of some derivatives of retinoic acid found in rat bile.

作者信息

Lippel K, Olson J A

出版信息

J Lipid Res. 1968 Sep;9(5):580-6.

PMID:5726316
Abstract

After the intraportal injection of retinoic acid-15-(14)C into rats, all-trans methyl retinoate, a cis isomer of methyl retinoate, retinoyl beta-glucurono-gamma-lactone, retinoic acid, and retinoyl beta-glucuronide were isolated from methanol extracts of rat bile by chromatography on anion-exchange resin and silicic acid columns and characterized on thin-layer plates of Silica Gel G. On the other hand, when bile was extracted with n-butanol or analyzed directly by thin-layer chromatography, only retinoyl beta-glucuronide and a very small amount of retinoic acid could be detected. Butanol extracts of the liver and the intestine, however, still contained a small radioactive nonpolar fraction. When retinoyl beta-glucuronide was incubated with an anion-exchange resin in the presence of methanol, several nonpolar products appeared. Apparently the methyl retinoate, retinoyl beta-glucurono-gamma-lactone, and most of the retinoic acid previously found in bile after retinoic acid administration are produced from retinoyl beta-glucuronide during the isolation procedure.

摘要

给大鼠门静脉注射视黄酸 -15-(14)C 后,通过阴离子交换树脂柱和硅酸柱色谱法从大鼠胆汁的甲醇提取物中分离出全反式甲基视黄酸、甲基视黄酸的顺式异构体、视黄酰β - 葡糖醛酸 -γ - 内酯、视黄酸和视黄酰β - 葡糖醛酸,并在硅胶G薄板上进行表征。另一方面,当用正丁醇提取胆汁或直接通过薄层色谱分析时,仅能检测到视黄酰β - 葡糖醛酸和极少量的视黄酸。然而,肝脏和肠道的丁醇提取物仍含有少量放射性非极性部分。当视黄酰β - 葡糖醛酸在甲醇存在下与阴离子交换树脂一起孵育时,出现了几种非极性产物。显然,视黄酸给药后先前在胆汁中发现的甲基视黄酸、视黄酰β - 葡糖醛酸 -γ - 内酯和大部分视黄酸是在分离过程中由视黄酰β - 葡糖醛酸产生的。

相似文献

1
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.
2
RETINOYL BETA-GLUCURONIC ACID: A MAJOR METABOLITE OF VITAMIN A IN RAT BILE.视黄酰β - 葡萄糖醛酸:大鼠胆汁中维生素A的主要代谢产物。
Science. 1965 Apr 2;148(3666):86-7. doi: 10.1126/science.148.3666.86.
3
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.
4
Biosynthesis of beta-glucuronides of retinol and of retinoic acid in vivo and in vitro.视黄醇和视黄酸的β-葡萄糖醛酸苷在体内和体外的生物合成。
J Lipid Res. 1968 Mar;9(2):168-75.
5
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.
6
The metabolism of retinoic acid to 5,6-epoxyretinoic acid, retinoyl-beta-glucuronide, and other polar metabolites.视黄酸代谢生成5,6-环氧视黄酸、视黄酰-β-葡萄糖醛酸苷及其他极性代谢产物。
Ann N Y Acad Sci. 1981 Feb 27;359:25-36. doi: 10.1111/j.1749-6632.1981.tb12734.x.
7
Metabolites of all-trans-retinoic acid in bile: identification of all-trans- and 13-cis-retinoyl glucuronides.胆汁中全反式维甲酸的代谢产物:全反式和13-顺式视黄酰葡萄糖醛酸苷的鉴定。
J Biol Chem. 1982 Apr 10;257(7):3537-43.
8
Metabolism of all-trans-retinoic acid and all-trans-retinyl acetate. Demonstration of common physiological metabolites in rat small intestinal mucosa and circulation.全反式视黄酸和全反式醋酸视黄酯的代谢。大鼠小肠黏膜和循环中常见生理代谢产物的证明。
J Biol Chem. 1985 Sep 5;260(19):10590-6.
9
Pathways of absorption of retinal and retinoic acid in the rat.大鼠中视黄醛和视黄酸的吸收途径
J Lipid Res. 1968 Jan;9(1):103-9.
10
Metabolism in vivo of all-trans-retinoic acid. Biosynthesis of 13-cis-retinoic acid and all-trans- and 13-cis-retinoyl glucuronides in the intestinal mucosa of the rat.全反式维甲酸在体内的代谢。大鼠肠黏膜中13-顺式维甲酸以及全反式和13-顺式维甲酸葡糖醛酸酯的生物合成。
J Biol Chem. 1982 Apr 10;257(7):3544-50.

引用本文的文献

1
Retinoic Acid Synthesis and Degradation.视黄酸的合成与降解
Subcell Biochem. 2016;81:127-161. doi: 10.1007/978-94-024-0945-1_5.
2
5,6-epoxyretinoic acid is a physiological metabolite of retinoic acid in the rat.5,6-环氧视黄酸是大鼠体内视黄酸的一种生理代谢产物。
Biochem J. 1980 Feb 15;186(2):475-81. doi: 10.1042/bj1860475.
3
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.
4
Studies on the in vivo metabolism of retinoic acid in the rat.大鼠体内视黄酸代谢的研究。
Lipids. 1970 Apr;5(4):371-8. doi: 10.1007/BF02532101.
5
Metabolic studies on retinoic acid in the rat.大鼠体内视黄酸的代谢研究。
Biochem J. 1971 Mar;122(1):1-4. doi: 10.1042/bj1220001.
6
Activation of retinoic acid by coenzyme A for the formation of ethyl retinoate.辅酶A激活视黄酸以形成视黄酸乙酯。
Proc Natl Acad Sci U S A. 1985 Oct;82(19):6419-22. doi: 10.1073/pnas.82.19.6419.
7
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.