The Isolation of Prostaglandin.

Bergström, Sune; Sjövall, Jan; Pihl, Alexander; Almin, K. E.; Magnéli, Arne; Pestmalis, Herbert; Åsbrink, Stig

doi:10.3891/acta.chem.scand.11-1086

Cited by 155 publications

(40 citation statements)

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“…The bile duct was cannulated with a 10 cm polyethylene tube (0.9mm external diameter) as described by Bergstrom et al [9] …”

Section: Operation Techniquementioning

confidence: 99%

Metabolism of Corticosterone in the Isolated Perfused Rat Liver

Eriksson¹,

Gustafsson²

1971

European Journal of Biochemistry

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[4-14C]Corticosterone was perfused through isolated livers from male and female rats. Bile, perfusate and liver tissue were extracted and analysed separately. No specific differences were observed in the distribution of various isomers of corticosterone metabolites isolated from these three sources. However, the radioactive metabolites with the chromatographic property of steroid glucuronides were mainly present in the bile. Male rat livers metabolized corticosterone into the following 20-hydroxy compounds : 5or-pregnane-3a,ilp,20p(and 200~),21-tetrol and 5or-pregnane-3p,l lp,20p,21-tetrol. I n female rat livers, on the other hand, only small amounts of 5n-pregnane-3p,ll#?,2Op,Zl -tetrol were formed. The predominant corticosterone metabolites isolated after perfusion of female rat livers were identified as 3or(and 3~),11t9,15or,21-tetrahydroxy5or-pregnan-20-one and 34and 3~),11~,21-trihydroxy-5or-pregnan-20-one. Furthermore, female rat livers produced a larger amount of mono-and disulphurylated metabolites than male livers. All these findings agree well with what has previously been found concerning the excretion of steroids in faeces from germfree rats. The present results therefore show that an important reason for the large sexual differences observed in rats in the faecal and urinary steroid patterns is a different hepatic metabolism of steroids in male and female rats.Experiments in vivo have shown that [4-14C]-corticosterone is metabolized in different ways in female and male rats [l]. The predominant faecal and urinary metabolite in germfree female rats was the 21-monosulphate of 3n,l1~,15~~,21-tetrahydroxy5n-pregnan-20-one [2] ; it also accounts for more than 50°/0 of the total steroid amount in faeces and urine from these animals [3]. I n striking contrast no 15-hydroxylated corticosterone metabolites were found in male rats. Germfree male rats excreted disulphurylated 50c-pregnane-3a( and 3@), 11f3,20t9,21-tetrol in faeces but most of the faecal and urinary radioactivity was recovered in the free steroid fraction [4]. Chromatography on SephadexLH-20 showed that these unconjugated metabolites were very polar.In order to study the biosynthesis of the metabolites isolated after the experiments in vivo corticosterone has been perfused through livers isolated from male and female rats. The present paper describes the results obtained in this investigation.Enzymes. 20a-and 20~-hydroxysteroid : oxidoreductase (EC 1.1.1.-) ; steroid-sulphate sulphohydrolase (EC 3.1.6.-) ; steroid hydroxylases (EC 1.14.1. -).Systematic Namea and Non-Standard Abbreviations. Corticosterone, 11/?,21-dihydroxy-4-pregnene-3,20-dione; silyl, trimethylsilyl. Retention times t~ are calculated relative to 5a-cholestane. 3n,11~,21-Trihydroxy-5or-pregnan-20-one was prepared by reduction of 11~,21-dihydroxy-5a-pregnane-3,20-dione (purchased from Ikapharm, RamatGan, P. 0. B. 31, Israel) with 3or-hydroxysteroid oxidoreductase as described previously [6]. A mixture of the 20t9 and 2001 epimers of 5a-pregnane-3&, 11~,20,21-tetrol was prepared ...

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“…The bile duct was cannulated with a 10 cm polyethylene tube (0.9mm external diameter) as described by Bergstrom et al [9] …”

Section: Operation Techniquementioning

confidence: 99%

Metabolism of Corticosterone in the Isolated Perfused Rat Liver

Eriksson¹,

Gustafsson²

1971

European Journal of Biochemistry

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“…Subsequently, Goldblatt (1933) andvon Euler (1934) independently found that the substance stimulated different smooth muscle organs and lowered blood pressure. A further study by Bergstrom and Sjovall (1957) isolated PGE 1 in crystalline form from the vesicular glands of sheep. They also confirmed the 1012 strong blood pressure-reducing activity of PGE 1 (Bergstrom et al, 1959a,b).…”

Section: Introductionmentioning

confidence: 99%

The Prostanoid EP4 Receptor and Its Signaling Pathway

Yokoyama

Iwatsubo²,

Umemura³

et al. 2013

Pharmacol Rev

227

257

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“…Comparing the UV spectrum of medullin in sulfuric acid with similar spectra of prostaglandins E 29 and prostaglandins F 28 reveals a striking spectrophotometric similarity between medullin and prostaglandins E, both of which have maximal absorption at 2600A and 3200A with an inflexion point at 3600A this is in contrast to prostaglandins F which display a single maximal absorption at approximately 3000A. Furthermore, a comparison between the spectra obtained from heattreated alkaline solutions of medullin and prostaglandins E-l 34 show similar absorption maxima at approximately 2800A.…”

Section: Figure 18mentioning

confidence: 99%

Renomedullary Vasodepressor Substance, Medullin

Lee

Covino

Takman

et al. 1965

Circulation Research

163

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The chemical and physiological properties of renomedullary depressor substances were investigated utilizing the normotensive, vagotomized, pentolinium-treated rat for assay. By a combination of solvent extraction, column chromatography, and thin-layer chromatography, three biologically active acidic lipids were isolated from rabbit renal medulla. The first compound, called medullin, is an acidic lipid with potent vasodepressor and relatively weak nonvascular smooth muscle-stimulating properties. Ultraviolet analysis revealed spectra closely resembling that of prostaglandin E-1 (PGE-1). Infrared analysis showed the presence of carbonyl, methylene, and hydroxyl groups in addition to trans ethylene bonds. Although closely resembling PGE-1, medullin appears to be a more unsaturated carboxylic lipid with less polar (hydroxyl) groups. The hypotensive action of medullin is attributable to a direct effect on peripheral arteriolar beds without cardiac depression, because intra-arterial and intravenous injections of medullin reduced peripheral resistance markedly and increased cardiac output simultaneously. In addition, no effect on cardiac rate or contractility was observed in the isolated rabbit heart preparation. Comparative studies of medullin and PGE-1 indicated that the hypotensive activity of these compounds is similar with respect to potency and mechanism of action. The only biological difference between crystalline PGE-1 and medullin was a fiftyfold greater stimulation of nonvascular smooth muscle by PGE-1 in comparison to medullin. A second biologically active acidic lipid isolated from rabbit medulla was tentatively identified as PGE-1, and was found to possess both vasodepressor and nonvascular smooth muscle-stimulating properties. The third isolate from rabbit medulla possessed potent intestinal stimulating activity but weak to absent vasodepressor effects, properties similar to those of prostaglandin F compounds.

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The Isolation of Prostaglandin.

Cited by 155 publications

References 0 publications

Metabolism of Corticosterone in the Isolated Perfused Rat Liver

Metabolism of Corticosterone in the Isolated Perfused Rat Liver

The Prostanoid EP4 Receptor and Its Signaling Pathway

Renomedullary Vasodepressor Substance, Medullin

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