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从用视黄酸处理的维生素A缺乏大鼠小肠中分离出的5,8-氧代视黄酸的鉴定。

Identification of 5,8-oxyretinoic acid isolated from small intestine of vitamin A-deficient rats dosed with retinoic acid.

作者信息

Napoli J L, McCormick A M, Schnoes H K, DeLuca H F

出版信息

Proc Natl Acad Sci U S A. 1978 Jun;75(6):2603-5. doi: 10.1073/pnas.75.6.2603.

DOI:10.1073/pnas.75.6.2603
PMID:275830
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC392610/
Abstract

A retinoid was isolated by a multistep procedure from the small intestines of vitamin A-deficient rats given a single dose of retinoic acid. The compound, designated 8II, was pure, as demonstrated by four high-pressure liquid chromatographic procedures. It was positively identified as 5,8-oxyretinoic acid by ultraviolet spectrophotometry, mass spectrometry, and spectral and chromatographic comparison to known compounds. It is probable that 5,8-oxyretinoic acid was produced from 5,6-epoxyretinoic acid under the acidic conditions used in the isolation. It is highly probable, therefore, that the natural product is 5,6-epoxyretinoic acid.

摘要

通过多步程序从给予单剂量视黄酸的维生素A缺乏大鼠的小肠中分离出一种类视黄醇。该化合物命名为8II,经四种高压液相色谱程序证明是纯的。通过紫外分光光度法、质谱法以及与已知化合物的光谱和色谱比较,确定其为5,8-氧代视黄酸。在分离所用的酸性条件下,5,8-氧代视黄酸可能由5,6-环氧视黄酸产生。因此,很可能天然产物是5,6-环氧视黄酸。

相似文献

1
Identification of 5,8-oxyretinoic acid isolated from small intestine of vitamin A-deficient rats dosed with retinoic acid.从用视黄酸处理的维生素A缺乏大鼠小肠中分离出的5,8-氧代视黄酸的鉴定。
Proc Natl Acad Sci U S A. 1978 Jun;75(6):2603-5. doi: 10.1073/pnas.75.6.2603.
2
Isolation and identification of 5, 6-epoxyretinoic acid: a biologically active metabolite of retinoic acid.5,6-环氧维甲酸的分离与鉴定:维甲酸的一种生物活性代谢产物
Biochemistry. 1978 Sep 19;17(19):4085-90. doi: 10.1021/bi00612a033.
3
Isolation of 5,8-oxyretinoic acid from rat intestinal mucosa.从大鼠肠黏膜中分离5,8-氧代视黄酸。
Arch Biochem Biophys. 1979 Feb;192(2):577-83. doi: 10.1016/0003-9861(79)90128-0.
4
Metabolism of 5,6-epoxyretinoic acid in vivo: isolation of a major intestinal metabolite.5,6-环氧视黄酸的体内代谢:一种主要肠道代谢物的分离
Biochemistry. 1982 Apr 13;21(8):1942-9. doi: 10.1021/bi00537a038.
5
Isolation and identification of 4-hydroxy- and 4-oxoretinoic acid. In vitro metabolites of all-trans-retinoic acid in hamster trachea and liver.4-羟基视黄酸和4-氧代视黄酸的分离与鉴定。全反式维甲酸在仓鼠气管和肝脏中的体外代谢产物。
Biochemistry. 1979 May 15;18(10):2092-7. doi: 10.1021/bi00577a039.
6
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.
7
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.
8
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.
9
Metabolism of retinoic acid in vivo in the vitamin A-deficient rat.维生素A缺乏大鼠体内视黄酸的代谢
Biochem J. 1982 Jul 15;206(1):33-41. doi: 10.1042/bj2060033.
10
Tissue dependence of retinoic acid metabolism in vivo.视黄酸在体内代谢的组织依赖性。
Biochim Biophys Acta. 1981 Oct 23;666(1):165-75. doi: 10.1016/0005-2760(81)90102-8.

引用本文的文献

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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
Cytochrome P450s in the regulation of cellular retinoic acid metabolism.细胞色素 P450 家族在细胞视黄酸代谢调控中的作用。
Annu Rev Nutr. 2011 Aug 21;31:65-87. doi: 10.1146/annurev-nutr-072610-145127.
3
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.
4
The identification of dehydroretinol (vitamin A2) in human skin.人皮肤中脱氢视黄醇(维生素A2)的鉴定。
Experientia. 1980 Mar 15;36(3):317-8. doi: 10.1007/BF01952299.

本文引用的文献

1
The preparation and biological activity of methyl 5,6-epoxy-retinoate.标题:5,6-环氧视黄酸甲酯的制备及生物活性
Biochem J. 1966 Dec;101(3):835-42. doi: 10.1042/bj1010835.
2
THE BIOLOGICAL FUNCTION OF VITAMIN A ACID.视黄酸的生物学功能
Proc Natl Acad Sci U S A. 1960 May;46(5):587-608. doi: 10.1073/pnas.46.5.587.
3
A BIOLOGICALLY ACTIVE METABOLITE OF VITAMIN A AND VITAMIN A ACID.一种维生素A和维生素A酸的生物活性代谢物。
Nature. 1964 Jul 25;203:411-2. doi: 10.1038/203410b0.
4
VITAMIN A AND REPRODUCTION IN RATS.维生素A与大鼠繁殖
Proc R Soc Lond B Biol Sci. 1964 Feb 18;159:510-35. doi: 10.1098/rspb.1964.0017.
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Metabolism and biological activity of vitamin A acid in the chick.雏鸡体内视黄酸的代谢与生物活性
J Nutr. 1963 Apr;79(4):503-10. doi: 10.1093/jn/79.4.503.
6
Studies on metabolism of vitamin A. 1. The biological activity of vitamin A acid in rats.维生素A代谢的研究。1. 视黄酸在大鼠体内的生物活性。
Biochem J. 1963 May;87(2):305-11. doi: 10.1042/bj0870305.
7
Identification of 13-cis retinoic acid in tissue extracts and its biological activity in rats.组织提取物中13-顺式维甲酸的鉴定及其在大鼠体内的生物活性。
Biochim Biophys Acta. 1967 Aug 29;141(3):639-41. doi: 10.1016/0304-4165(67)90194-8.
8
Preparation, properties and metabolism of 5,6-monoepoxyretinoic acid.5,6-单环氧维甲酸的制备、性质及代谢
Biochem J. 1967 May;103(2):539-43. doi: 10.1042/bj1030539.
9
Formation of retinoic acid from retinol in the rat.大鼠体内视黄醇向视黄酸的转化
Biochem J. 1967 Feb;102(2):606-11. doi: 10.1042/bj1020606.
10
Pathways of retinol and retinoic acid metabolism in the rat.大鼠体内视黄醇和视黄酸的代谢途径。
Biochem J. 1967 Feb;102(2):600-5. doi: 10.1042/bj1020600.