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17R(18S)环氧二十碳四烯酸,一种20:5n-3在猴精囊中的细胞色素P-450代谢产物,被代谢为新型前列腺素。

17R(18S)epoxyeicosatetraenoic acid, a cytochrome P-450 metabolite of 20:5n-3 in monkey seminal vesicles, is metabolized to novel prostaglandins.

作者信息

Oliw E H

机构信息

Department of Pharmaceutical Pharmacology, Uppsala University Biomedical Centre, Sweden.

出版信息

Biochem Biophys Res Commun. 1991 Aug 15;178(3):1444-50. doi: 10.1016/0006-291x(91)91055-h.

DOI:10.1016/0006-291x(91)91055-h
PMID:1908237
Abstract

Eicosapentaenoic acid (20:5n-3) is metabolized by cytochrome P-450w3 of monkey seminal vesicles to 17R(18S)epoxy-5,8,11,14-eicosatetraenoic acid (17R(18S)EpETE). PGH synthase is abundant in this tissue. Racemic 17(18)EpETE was therefore investigated as a substrate of PGH synthase. The main products were identified as two diastereoisomers of 17(18)epoxyprostaglandin E2, which were formed in a 4:5 ratio. The structures were confirmed by authentic material. The natural epoxide enantiomer can thus be metabolized to novel 17R(18S)epoxyprostaglandins.

摘要

二十碳五烯酸(20:5n-3)在猴精囊的细胞色素P-450w3作用下代谢为17R(18S) -环氧-5,8,11,14-二十碳四烯酸(17R(18S)EpETE)。PGH合酶在该组织中含量丰富。因此,外消旋17(18)EpETE被作为PGH合酶的底物进行研究。主要产物被鉴定为17(18) -环氧前列腺素E2的两种非对映异构体,其生成比例为4:5。结构经标准品确认。天然环氧化物对映体因此可代谢为新型17R(18S) -环氧前列腺素。

相似文献

1
17R(18S)epoxyeicosatetraenoic acid, a cytochrome P-450 metabolite of 20:5n-3 in monkey seminal vesicles, is metabolized to novel prostaglandins.17R(18S)环氧二十碳四烯酸,一种20:5n-3在猴精囊中的细胞色素P-450代谢产物,被代谢为新型前列腺素。
Biochem Biophys Res Commun. 1991 Aug 15;178(3):1444-50. doi: 10.1016/0006-291x(91)91055-h.
2
Biosynthesis of prostaglandins from 17(18)epoxy-eicosatetraenoic acid, a cytochrome P-450 metabolite of eicosapentaenoic acid.从17(18)-环氧-二十碳四烯酸(一种二十碳五烯酸的细胞色素P-450代谢产物)生物合成前列腺素。
Biochim Biophys Acta. 1992 Jun 26;1126(3):261-8. doi: 10.1016/0005-2760(92)90239-r.
3
Biosynthesis of 18(RD)-hydroxyeicosatetraenoic acid from arachidonic acid by microsomes of monkey seminal vesicles. Some properties of a novel fatty acid omega 3-hydroxylase and omega 3-epoxygenase.猴精囊微粒体从花生四烯酸生物合成18(R)-羟基二十碳四烯酸。一种新型脂肪酸ω-3羟化酶和ω-3环氧化酶的某些特性。
J Biol Chem. 1989 Oct 25;264(30):17845-53.
4
Biosynthesis of 5,6-dihydroxyprostaglandin E1 and F1 alpha from 5,6-dihydroxyeicosatrienoic acid by ram seminal vesicles.公羊精囊将5,6 - 二羟基二十碳三烯酸生物合成为5,6 - 二羟基前列腺素E1和F1α 。
Biochim Biophys Acta. 1984 Sep 12;795(2):384-91. doi: 10.1016/0005-2760(84)90089-4.
5
Metabolism of polyunsaturated (n-3) fatty acids by monkey seminal vesicles: isolation and biosynthesis of omega-3 epoxides.猴精囊对多不饱和(n-3)脂肪酸的代谢:ω-3环氧化物的分离与生物合成
Biochim Biophys Acta. 1991 Nov 27;1086(3):287-94. doi: 10.1016/0005-2760(91)90172-e.
6
Eicosapentaenoic acid is converted via ω-3 epoxygenation to the anti-inflammatory metabolite 12-hydroxy-17,18-epoxyeicosatetraenoic acid.二十碳五烯酸通过 ω-3 环氧化作用转化为抗炎代谢物 12-羟基-17,18-环氧二十碳四烯酸。
FASEB J. 2014 Feb;28(2):586-93. doi: 10.1096/fj.13-236224. Epub 2013 Oct 15.
7
On the metabolism of epoxyeicosatrienoic acids by ram seminal vesicles: isolation of 5(6)epoxy-prostaglandin F1 alpha.关于公羊精囊对环氧二十碳三烯酸的代谢:5(6) - 环氧 - 前列腺素F1α的分离
Biochem Biophys Res Commun. 1985 Feb 15;126(3):1090-6. doi: 10.1016/0006-291x(85)90297-9.
8
Identification of 6-ketoprostaglandin F1alpha formed from arachidonic acid in bovine seminal vesicles.牛精囊中由花生四烯酸形成的6-酮前列腺素F1α的鉴定。
Biochim Biophys Acta. 1976 Jan 18;486(1):136-44.
9
Isolation of 19,20-dehydroprostaglandins E1 and E2 in human seminal fluid and further studies on 18,19-dehydroprostaglandins E1 and E2.人精液中19,20-脱氢前列腺素E1和E2的分离以及对18,19-脱氢前列腺素E1和E2的进一步研究。
Arch Biochem Biophys. 1987 Oct;258(1):272-86. doi: 10.1016/0003-9861(87)90345-6.
10
A novel arachidonic acid 18(R)-hydroxylase and eicosapentaenoic acid omega 3-epoxygenase of seminal vesicles.精囊中的一种新型花生四烯酸18(R)-羟化酶和二十碳五烯酸ω-环氧酶。
Adv Prostaglandin Thromboxane Leukot Res. 1991;21A:197-200.

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Molecules. 2025 Mar 24;30(7):1445. doi: 10.3390/molecules30071445.
2
17(R),18(S)-epoxyeicosatetraenoic acid, a potent eicosapentaenoic acid (EPA) derived regulator of cardiomyocyte contraction: structure-activity relationships and stable analogues.17(R),18(S)-环氧二十碳四烯酸,一种强效的二十碳五烯酸 (EPA) 衍生的心肌细胞收缩调节剂:结构-活性关系和稳定类似物。
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