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Steroids – Basic Science STEROIDS – BASIC SCIENCE Edited by Hassan Abduljabbar Steroids – Basic Science Edited by Hassan Abduljabbar Published by InTech Janeza Trdine 9, 51000 Rijeka, Croatia Copyright © 2011 InTech All chapters are Open Access distributed under the Creative Commons Attribution 3.0 license, which allows users to download, copy and build upon published articles even for commercial purposes, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. After this work has been published by InTech, authors have the right to republish it, in whole or part, in any publication of which they are the author, and to make other personal use of the work. Any republication, referencing or personal use of the work must explicitly identify the original source. As for readers, this license allows users to download, copy and build upon published chapters even for commercial purposes, as long as the author and publisher are properly credited, which ensures maximum dissemination and a wider impact of our publications. Notice Statements and opinions expressed in the chapters are these of the individual contributors and not necessarily those of the editors or publisher. No responsibility is accepted for the accuracy of information contained in the published chapters. The publisher assumes no responsibility for any damage or injury to persons or property arising out of the use of any materials, instructions, methods or ideas contained in the book. Publishing Process Manager Bojan Rafaj Technical Editor Teodora Smiljanic Cover Designer InTech Design Team Image Copyright loriklaszlo, 2011. DepositPhotos First published December, 2011 Printed in Croatia A free online edition of this book is available at www.intechopen.com Additional hard copies can be obtained from [email protected] Steroids – Basic Science, Edited by Hassan Abduljabbar p. cm. ISBN 978-953-307-866-3 free online editions of InTech Books and Journals can be found at www.intechopen.com Contents Preface IX Part 1 Physiology of Steroid Hormones 1 Chapter 1 Hormonal and Neural Mechanisms Regulating Hormone Steroids Secretion 3 Roberto Domínguez, Angélica Flores and Sara E. Cruz-Morales Chapter 2 The Tissue Specific Role of Estrogen and Progesterone in Human Endometrium and Mammary Gland 35 Karin Tamm, Marina Suhorutshenko, Miia Rõõm, Jaak Simm and Madis Metsis Chapter 3 Evolving Trends in Estrogen Receptor Biology 65 Raghava Varman Thampan Part 2 Pathophysiology of Steroid Hormones 83 Chapter 4 Cryptorchidism and Steroid Hormones 85 Marzena Kamieniczna, Anna Havrylyuk and Maciej Kurpisz Chapter 5 Dehydroepiandrosterone in Nonalcoholic Fatty Liver Disease 97 Yoshio Sumida, Kyoko Sakai, Tomoyuki Ohno, Kazuyuki Kanemasa, Yutaka Inada, Naohisa Yoshida, Kohichiroh Yasui, Yoshito Itoh, Yuji Naito, Toshikazu Yoshikawa Chapter 6 DHEA and Impaired Glucose Tolerance Clinical and Basic Study 109 Hajime Ueshiba Chapter 7 17-Hydroxysteroid Dehydrogenase Type 3 Deficiency: Diagnosis, Phenotypic Variability and Molecular Findings 119 Maria Felicia Faienza and Luciano Cavallo VI Contents Chapter 8 Steroid Hormones in Drosophila: How Ecdysone Coordinates Developmental Signalling with Cell Growth and Division 141 Leonie Quinn, Jane Lin, Nicola Cranna, Jue Er Amanda Lee, Naomi Mitchell and Ross Hannan Part 3 Pharmacology 169 Chapter 9 Approaches for Searching of Modified Steroid Estrogen Analogues with Improved Biological Properties 171 Alexander Shavva, Svetlana Morozkina and Olga Galkina Chapter 10 Drug Design Approaches to Manipulate the Agonist-Antagonist Equilibrium in Steroid Receptors 221 Scott J. Lusher, Paolo Conti, Wim Dokter, Pedro H. Hermkens and Jacob de Vlieg Preface This book explains the basic science of steroids and is targeted towards professionals engaged in health services. It should be noted that medical science evolves rapidly and some information like the understanding of steroids and their therapeutic use may change with new concepts quickly. Steroids are either naturally occurring or synthetic fat-soluble organic compounds. They are found in plants, animals, and fungi. They mediate a very diverse set of biological responses. The most widespread steroid in the body is cholesterol, an essential component of cell membranes, and the starting point for the synthesis of other steroids. Since the science of steroids has an enormous scope, we decided to put the clinical aspects of steroids in a different book titled “Steroids: Clinical Aspects”. The two books complete each other. We hope that the reader will gain valuable information from both books and enrich their knowledge about this fascinating topic. Hassan Abduljabbar Professor of Obstetrics and Gynecology, King Abdulaziz University, Kingdom of Saudi Arabia Part 1 Physiology of Steroid Hormones 1 Hormonal and Neural Mechanisms Regulating Hormone Steroids Secretion Roberto Domínguez1, Angélica Flores1 and Sara E. Cruz-Morales2 1Facultad de Estudios Superiores Zaragoza, 2Facultad de Estudios Superiores Iztacala Universidad Nacional Autónoma de México México 1. Introduction Hormonal and neural signals participate in regulating the synthesis and release of steroid hormones from the adrenals, ovaries and testicles. Hormonal signals arise from the hypothalamus, pituitary, thyroid, thymus, adipose tissue, as well as from the adrenals, ovaries and testicles. Neural signals originating in the hypothalamus and other regions of the central and peripheral nervous system modulate the responses to the hormonal signals sent to the adrenals, ovaries and testicles. In female, the involvement of the adrenal and ovarian innervations in regulating the synthesis and release of steroid hormones have shown that right and left organs have different abilities to carry out these functions (Gerendai et al., 2000; Domínguez et al., 2003). The asymmetric capacity to release steroid hormones is related to differences in the origin and type of innervations received by right and left organs (Tóth et al., 2007; Gerendai et al., 2009). In addition, the way neuroendocrine signals participate in regulating steroid hormones secretion is different for each hormone, and the release of ovarian hormones is regulated according to the day of the estrus cycle. Scientific reviews on the biochemical steps that take place during the capture and processing of cholesterol and synthesis of steroid hormones, as well as in the regulation of the enzymes activities have been published in the last decade (Auchus & Miller, 2000; Straus & Hsue, 2000; Stocco, 2008; Boon et al., 2010; Chung et al., 2011). In such regard, the present chapter presents only a summary of those aspects we think are relevant to analyze the neuroendocrine regulation of steroid hormones secretion. 2. Steroid hormones Steroid hormones are classified according to the number of carbon (C) atoms in the molecule deriving from the pregnane (C-21), androstane (C-19) or estrane (C-18) nucleus. C-21 hormones include progesterone, cortisol, corticosterone and aldosterone; C-19 testosterone, androstenedione (A4) and dihydrotestosterone; and C-18 estradiol, estrone and estriol. Based on its functional actions, steroid hormones are classified into five principal classes: estrogens (estradiol, estrone, estriol), progestins (progesterone), androgens (testosterone, A4, 4 Steroids – Basic Science dihydrotestosterone), glucocorticoid (cortisol, corticosterone), and mineralocorticoids (aldosterone, deoxicorticosterone). All steroid hormones derive from cholesterol in a process that includes: - de novo synthesis of cholesterol from acetate, the cholesterol release from cholesterol esters stored in lipid cytoplasmic droplets, and the capture and processing of blood cholesterol - the transport of cholesterol to the mitochondria; - the conversion of cholesterol to pregnenolone; - the transport of pregnenolone to the smooth endoplasmic reticulum; - modifications of the pregnenolone molecule and the synthesis of active hormones; - the transport of active hormones to the cell membrane and the release of hormones to the blood stream; - the biosynthesis of new hormones in the peripheral tissues through enzymes acting on steroid hormones as precursors; - the activation or inactivation of steroid hormones by organs or tissues; the catabolism and elimination of catabolites by urine, bilis or feces; - the esterification of the steroid hormone molecules and its elimination through the urine, bilis or feces. 3. Capture and processing of cholesterol Cells synthesizing steroid hormones (steroidogenic cells) use several pathways that ensure the constant supply of cholesterol for steroid hormone synthesis, including: 1. De novo synthesis from acetate in the endoplasmic reticulum; 2. The mobilization of cholesterol esters stored in lipid droplets through cholesterol-ester hydrolase; 3. The uptake of blood lipoproteins carrying cholesterol (low-density (LDL) and high- density lipoproteins (HDL). The incorporation of lipoproteins into the cells is mediated by a receptor-endocytic mechanism that delivers the lipoproteins to the lysosomes where apolipoproteins are degraded. High density lipoproteins (HDL) are incorporated by the scavenger receptor class B, type I (SR-BI)-mediated selective uptake. Depending on the cell, the synthesis of lipoprotein receptors is stimulated by the adreno-corticotropin-hormone (ACTH) and luteinizing hormone (LH). The source of cholesterol for steroidogenesis varies according to the animal studied (Azhar et al., 2003; Hu et al., 2011). SR-BI synthesis in
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