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Adrenal and Extra-Adrenal Production of 11-Deoxycorticosterone Monica Adrenal and extra-adrenal production of 11-deoxycorticosterone Monica Ann Schneider A thesis submitted for the degree of Doctor of Philosophy University of London i ProQuest Number: U553451 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a com plete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. uest ProQuest U553451 Published by ProQuest LLC(2017). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States C ode Microform Edition © ProQuest LLC. ProQuest LLC. 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 48106- 1346 Abstract The conversion of progesterone to 11-deoxycorticosterone (DOC), a steroid known to be hypertensive, by adrenal and extra-adrenal 21-hydroxylase enzyme activity was investigated. For assessment of DOC production, a method for determining the excretion rate of tetrahydro-11-deoxycorticosterone (THDOC), a urinary metabolite of DOC, was developed. Various chromatographic techniques were employed, with detection of the steroid by gas chromatography coupled to a mass spectrometer (GC-MS), using selected ion monitoring (SIM), after MO-TMS ether formation. Inspection of the mass spectrum of THDOC showed Ion m/z 476 to be the obvious candidate for SIM, with the molecular ion (M+, m/z 507) providing confirmatory evidence for the steroid. Ion 476 proved to be unsuitable for quantitative analysis, in pregnancy and some other clinical situations, due to the presence of co-eluting steroids. The molecular ion was therefore used for quantification. These data highlighted the need for users of SIM in general to take care in the selection of the monitored ions. During pregnancy, serial urine samples were analyzed in normal women, patients with raised progesterone (for example from ovarian theca lutein cysts) and hypertension (pre-eclamptic toxaemia - PET). Ranges for various urinary steroid metabolites were established. Urine samples from patients undergoing in vitro fertilization with oocyte donation were also investigated, both during and after progesterone and oestrogen administration, which allowed assessment of the exogenous steroids. Correlation of excretion rates of THDOC with pregnanediol, a main urinary metabolite of progesterone, offered some support for extra-adrenal 21- hydroxylase activity. Many urinary metabolites of progesterone, generally hydroxypregnanolones (including THDOC) were found, particularly in pregnancy. The relative importance of some of these metabolites, using the Ion 476 SIM response, was found to be different in PET and placental sulphatase deficiency (PSD). One of the 2 hydroxypregnanolones, in pregnancy urine extracts, was found to co-elute with THDOC on gas chromatography. Various methods of separation of this co-eluting steroid, prior to the GC analysis were explored. The use of Celite gradient elution chromatography eventually facilitated almost complete separation and allowed tentative identification of 3,16-dihydroxypregnan-20-one. A hypothesis, put forward in the literature, that extra-adrenal DOC production is promoted by oestrogens, was not supported by data from pregnant subjects with PSD (who have low oestrogen production), as they were found to have THDOC excretion rates similar to normal pregnant subjects. Doubt was also raised, from mass spectral evidence, as to the accuracy of progesterone to DOC conversion rates (measured by the rate of THDOC excretion) quoted in a number of published papers, that used radioactive isotope ratios to suggest the presence of extra-adrenal DOC production. THDOC excretion rates were quantified in a number of further clinical situations with elevated progesterone and/or DOC production. A patient with a recurring DOC secreting tumour, followed over 53 months, along with subjects with congenital adrenal hyperplasia (due to 116-, 17- and 21-hydroxylase deficiency), were studied. The separate function of the zona glomerulosa (ZG) and fasciculata (ZF) of the adrenal cortex is described in a patient with 116-hydroxylase deficiency. DOC production was stimulated in the ZF after stimulation of the renin-angiotensin system, following suppression of ACTH stimulation of the ZG. A further objective of the project was to explore the use of deuterium labelled steroids in metabolic studies, thus avoiding the use of radioactivity, with its inherent risks, particularly during pregnancy. Deuterium labelled progesterone was obtained and its purity and enrichment assessed by GC-MS; unfortunately there was too little for further studies. A pilot study with 2H-cortisol showed that this could be useful in studying cortisol metabolites in vivo. 3a List of abbreviations 11BOHSD llfl-hydroxysteroid dehydrogenase 170HPr 17-hydroxypregnanolone (3a, 17a-dihydroxy-5fi-pregnan-20-one) ACTH Adrenocorticotrophin hormone And. Androsterone (3 a-hydroxy-5a-androstan-17-one) Aet. Aetiocholanolone (3a-hydroxy-5fl-androstan-17-one) A,S and C Internal standards for quantification - 5a-androstane-3a,17a-diol, stigmasterol and cholesteryl butyrate BO Benzylhydroxylamine BSA Body surface area CAH Congenital adrenal hyperplasia CBG Corticosterone binding globulin CRF Corticotrophin releasing factor dex. Dexamethasone DHA[-S] Dehydroepiandrosterone [-sulphate] (3fl-hydroxy-15-androsten-17-one) DOC 11-deoxycorticosterone (21-hydroxy-4-pregnene-3,20-dione) E Cortisone (17a,21-dihydroxy-4-pregnene-3,11,20-trione) EMS Early morning sample EO Ethoxylamine Eyal Oestradiol valerate F Cortisol (1 lfl,17a,21-trihydroxy-4-pregnene-3,20-dione) FID Flame ionization detector foil. Follicular (phase of the menstrual cycle) GC-MS Gas chromatography-mass spectrometry HBV Hold back volume hCG Human chorionic gonadotrophin HMDS Hexamethyldisilazane HO Hydroxyl amine HPLC High performance liquid chromatography IA Immunoadsorption I.D. Internal diameter IRMS Isotope ratio mass spectrometry IS Internal standard IVF In vitro fertilization KCH Kings College Hospital LDL Low density lipoproteins M+ Molecular ion MIS Mullerian inhibitory substance MO-HC1 Methyloxime hydrochloride MO-TMS Methyloxime trimethylsilyl ether MSD Mass Selective Detector MU Methylene unit 3b NMR Nuclear magnetic resonance oc. Oral contraceptives 0E3 Oestriol (1,3,5(10)-oestratrien-3,16a, 1715-triol) -OH Hydroxylase P Progesterone (4-pregnene-3,20-dione) PCO Polycystic ovary PD Pregnanediol (5fi-pregnane-3a,20a-diol) PET Preeclamptic toxaemia PRA Plasma renin activity Prl, Pr2 and Pr3 Additional hydroxypregnanolones found in SIM runs, using ion 476, in pregnancy urine samples PSD Placental sulphatase deficiency PT Pregnanetriol (5fi-pregnane-3a, 17a,20a-triol) RER Rough endoplasmic reticulum RIA Radioimmunoassay SD Standard deviation SER Smooth endoplasmic reticulum SIM Selected ion monitoring S 11-deoxycortisol (17a,21-dihydroxy-4-pregnene-3,20-dione) SV Simple virilizing SW Salt wasting TIC Total ion chromatogram THDOC Tetrahydrodeoxycorticosterone (unless otherwise stated the 3a,2 l-dihydroxy-5B-pregnan-20-one isomer) THE Tetrahydrocortisone (3a, 17a,2 l-trihydroxy-56-pregnane-l 1,20-dione) THF Tetrahydrocortisol (3a, 1 IB, 17a,21-tetrahydroxy-5fi-pregnan-20-one) THS Tetrahydrodeoxy cortisol (3a, 17a,21-trihydroxy-5B-pregnan-20-one) TLC Thin layer chromatography TMSI Trimethylsilyl imadazole 3c Table of contents Chapter Index T itle ....................................................................................................................................1 Abstract ...........................................................................................................................2 Table of contents.............................................................................................................4 Acknowledgements........................................................................................................ 19 Chapter 1 - Introduction............................................................................................ 20 1.1 Initial aims of the project 1.2 Maturation and inhibition of the human adrenal cortex 1.2.1 Embryology 1.2.2 Cytology 1.2.3 Vasculature and innervation 1.2.4 Pathways of adrenal steroid biochemistry 1.2.5 Enzymes of adrenal steroid biosynthesis 1.2.6 Control of steroidogenesis 1.2.7 Cell differentiation and adrenal growth 1.2.8 Fetal steroidogenesis and the "feto-placental steroidogenic unit" 1.2.9 Parturition 1.2.10 Neonatal life 1.2.11 Adrenarche 1.2.12 Sexual differentiation and congenital adrenal hyperplasia 1.2.13 Polycystic ovary (PCO) syndrome 1.2.14 Ectopic adrenal tissue and tumours 1.2.15 Adrenopause Clinical significance of deoxycorticosterone 1.3.1 Introduction 1.3.2 The menstrual cycle 1.3.3 Pregnancy 1.3.4 Other clinical situations with altered patterns of plasma DOC concentrations 4 1.4 Extra-adrenal 21 -hydroxylase enzymes 1.5 The renin-angiotensin system 1.6 Profiling steroid hormones using glass capillary gas chromatography 1.6.1 Introduction 1.6.2 Extraction 1.6.3 Hydrolysis 1.6.4 Additional separation of steroids 1.6.5 Derivatization of steroids 1.6.6 Gas chromatographic conditions and detection 1.7 The use of stable isotopes in Endocrinology 1.7.1 Radioactive versus stable isotopes 1.7.2' Analytical techniques available 1.7.3 Availability :s , ■, i > > > > 1.7.4 Toxicity --N N % 1.7.5 Quantitative applications 1.7.5.1 Internal
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