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14-September-2008 18:02:37 - Steroid This article is about the chemical family of steroids. For the performance enhancing substance, see Anabolic steroid. Steroid skeleton of lanosterol. The total number of carbons 30 reflects its triterpenoid origin. Steroid skeleton of lanosterol. The total number of carbons 30 reflects its triterpenoid origin. A steroid is a terpenoid lipid characterized by a carbon skeleton with four fused rings, generally arranged in a 6-6-6-5 fashion. Steroids vary by the functional groups attached to these rings and the oxidation state of the rings. Hundreds of distinct steroids are found in plants, animals, and fungi. All steroids are made in cells either from the sterol lanosterol animals and fungi or the sterol cycloartenol plants. Both sterols are derived from the cyclization of the triterpene squalene.1 Contents 1 Origin 2 Classification 2.1 Taxonomical/Functional 2.2 Structural 3 See also 4 References 5 Further reading 6 External links Origin Simplified version of the steroid synthesis pathway with the intermediates isopentenyl pyrophosphate IPP, dimethylallyl pyrophosphate DMAPP, geranyl pyrophosphate GPP and squalene shown. Some intermediates are omitted. Simplified version of the steroid synthesis pathway with the intermediates isopentenyl pyrophosphate IPP, dimethylallyl pyrophosphate DMAPP, geranyl pyrophosphate GPP and squalene shown. Some intermediates are omitted. Steroids include estrogen US spelling or oestrogen UK/AUS spelling, progesterone and testosterone. Estrogen and progesterone are made primarily in the ovary and in the placenta during pregnancy and testosterone in the testes. Testosterone is also converted into estrogen to regulate the supply of each, in the bodies of both females and males. Certain neurons and glia in the central nervous system CNS express the enzymes that are required for the local synthesis of pregnane neurosteroids, either de novo or from peripherally derived sources. The rate limiting step of steroid synthesis is the conversion of cholesterol to pregnenolone which occurs inside the mitochondrion.2 Classification Taxonomical/Functional Some of the common categories of steroids: Animal steroids Insect steroids Ecdysteroids such as ecdysterone Vertebrate steroids Steroid hormones Sex steroids are a subset of sex hormones that produce sex differences or support reproduction. They include androgens, estrogens, and progestagens. Corticosteroids include glucocorticoids and mineralocorticoids. Glucocorticoids regulate many aspects of metabolism and immune function, whereas mineralocorticoids help maintain blood volume and control renal excretion of electrolytes. Anabolic steroids are a class of steroids that interact with androgen receptors to increase muscle and bone synthesis. There are natural and synthetic anabolic steroids. In popular language the word steroids usually refers to anabolic steroids. Cholesterol which modulates the fluidity of cell membranes and is the principle constituent of the plaques implicated in atherosclerosis. Plant steroids Phytosterols Brassinosteroids Fungus steroids Ergosterols Structural It is also possible to classify steroids based upon their chemical composition. One example of how MeSH performs this classification is available at the MeSH catalog. Examples from this classification include: Class Examples Number of carbon atoms Cholstanes cholesterol 27 Cholanes cholic acid 22 Pregnanes progesterone 21 Androstanes testosterone 19 Estranes estradiol 18 See also Batrachotoxin List of steroid abbreviations Steroid biosynthesis References ^ Lanosterol biosynthesis ^ Rossier MF 2006. T channels and steroid biosynthesis: in search of a link with mitochondria. Cell Calcium. 40 2: 155-64. doi:10.1016/j.ceca.2006.04.020. PMID 16759697. Further reading G. P. Moss 1989. Nomenclature of Steroids Recommendations 1989. Pure Appl. Chem. 61 10: 1783-1822. doi:10.1351/pac198961101783. External links Michael W. King's Medical Biochemistry. Steroids and retinoids are both terpenes which are hydrophobic, pass through cell membranes and bind to intracellular receptors. However, retinoic acid is not a steroid because it does not have the defining ring structure. See: Steroids and Related Hydrophobic Molecules. Biochemistry by Jeremy M. Berg, John L. Tymoczko and Lubert Stryer 2002 W. H. Freeman and Co. steroid topics in this Steroids, Rage and Criminal Activity -- Video: Insidermedicine.com's Maria Radina on Anabolic Androgenic Steroids, as presented in a study in Archives of General Psychiatry. Nomenclature of Steroids Home Page at Queen Mary University of London. Steroid abbreviations at ISAS page now defunct, web archive version v d e Types of Steroids Precursors: Squalene | Lanosterol Common: Cholesterol | Pregnenolone | 17-Hydroxypregnenolone | DHEA | Androstenedione | Androstanediol Estrogens: Estradiol | Estriol | Estrone Androgens: Testosterone | Dihydrotestosterone | Androsterone Progestagens: Progesterone | 17-Hydroxyprogesterone | Progestins Glucocorticoids: Cortisol | Prednisone Mineralocorticoids: Aldosterone Phytosterols: Stigmasterol | Brassicasterol Ergosterols: Ergosterol | Ergocalciferol Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Steroid Categories: Steroids Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية БългарÑ?ки Català Česky Deutsch Español Esperanto Français í•œêµì–´ Hrvatski Italiano עברית Bahasa Melayu Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Occitan Polski Português Română РуÑ?Ñ?кий Simple English SlovenÄ?ina СрпÑ?ки / Srpski Srpskohrvatski / СрпÑ?кохрватÑ?ки Suomi Svenska ไทย Türkçe ä¸æ–‡ This page was last modified on 12 September 2008, at 02:16
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