BackgroundA steroid compoundx an organic compound with four anabolic steroid compounds arranged in a specific molecular configuration. Examples include the dietary lipid cholesterolthe sex hormones estradiol and testosterone : The steroid core structure is composed of seventeen carbon atoms, bonded in aanbolic " fused " rings: Steroids vary by the functional groups attached to this four-ring core and by the oxidation state of the rings. Sterols are forms of steroids with a anabolic steroid compounds group at position three and a skeleton derived from cholestane.
Steroid - Wikipedia
A steroid is an organic compound with four rings arranged in a specific molecular configuration. Examples include the dietary lipid cholesterol , the sex hormones estradiol and testosterone : The steroid core structure is composed of seventeen carbon atoms, bonded in four " fused " rings: Steroids vary by the functional groups attached to this four-ring core and by the oxidation state of the rings.
Sterols are forms of steroids with a hydroxy group at position three and a skeleton derived from cholestane. Hundreds of steroids are found in plants , animals and fungi. All steroids are manufactured in cells from the sterols lanosterol animals and fungi or cycloartenol plants. Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene. Gonane , also known as steran or cyclopentaperhydrophenanthrene, the simplest steroid and the nucleus of all steroids and sterols,   is composed of seventeen carbon atoms in carbon-carbon bonds forming four fused rings in a three-dimensional shape.
The three cyclohexane rings A, B, and C in the first illustration form the skeleton of a perhydro derivative of phenanthrene. The D ring has a cyclopentane structure. When the two methyl groups and eight carbon side chains at C, as shown for cholesterol are present, the steroid is said to have a cholestane framework. Isomerisation at the C side chain produces a parallel series of compounds, referred to as isosteroids. Testosterone , the principal male sex hormone and an anabolic steroid.
Cholic acid , a bile acid , showing the carboxylic acid and additional hydroxyl groups often present. Dexamethasone , a synthetic corticosteroid drug. Lanosterol , the biosynthetic precursor to animal steroids. The number of carbons 30 indicates its triterpenoid classification. Progesterone , a steroid hormone involved in the female menstrual cycle, pregnancy, and embryogenesis. Medrogestone , a synthetic drug with effects similar to progesterone.
In addition to the ring scissions cleavages , expansions and contractions cleavage and reclosing to a larger or smaller rings —all variations in the carbon-carbon bond framework—steroids can also vary:. For instance, sterols such as cholesterol and lanosterol have an hydroxyl group attached at position C-3, while testosterone and progesterone have a carbonyl oxo substituent at C-3; of these, lanosterol alone has two methyl groups at C-4 and cholesterol with a C-5 to C-6 double bond differs from testosterone and progesterone which have a C-4 to C-5 double bond.
The following are some common categories of steroids. In eukaryotes , steroids are found in fungi, animals, and plants. Fungal steroids include the ergosterols. Animal steroids include compounds of vertebrate and insect origin, the latter including ecdysteroids such as ecdysterone controlling molting in some species. Vertebrate examples include the steroid hormones and cholesterol; the latter is a structural component of cell membranes which helps determine the fluidity of cell membranes and is a principal constituent of plaque implicated in atherosclerosis.
Plant steroids include steroidal alkaloids found in Solanaceae ,  the phytosterols , and the brassinosteroids which include several plant hormones. In prokaryotes , biosynthetic pathways exist for the tetracyclic steroid framework e.
Steroids can be classified functionally. The major classes of steroid hormones, with prominent members and examples of related functions, are: As well as the following class of secosteroids open-ring steroids:.
Steroids can be classified based on their chemical composition. Examples of this classification include:. The gonane steroid nucleus is the parent carbon tetracyclic hydrocarbon molecule with no alkyl sidechains.
Secosteroids Latin seco , "to cut" are a subclass of steroidal compounds resulting, biosynthetically or conceptually, from scission cleavage of parent steroid rings generally one of the four.
Major secosteroid subclasses are defined by the steroid carbon atoms where this scission has taken place. For instance, the prototypical secosteroid cholecalciferol , vitamin D 3 shown , is in the 9,secosteroid subclass and derives from the cleavage of carbon atoms C-9 and C of the steroid B-ring; 5,6-secosteroids and 13,steroids are similar.
Norsteroids nor- , L. The former involves enzymic ring expansion-contraction reactions, and the latter is accomplished biomimetically or more frequently through ring closures of acyclic precursors with more or fewer ring atoms than the parent steroid framework. Combinations of these ring alterations are known in nature. For instance, ewes who graze on corn lily ingest cyclopamine shown and veratramine , two of a sub-family of steroids where the C- and D-rings are contracted and expanded respectively via a biosynthetic migration of the original C atom.
Ingestion of these C-nor-D-homosteroids results in birth defects in lambs: Steroids and their metabolites often function as signalling molecules the most notable examples are steroid hormones , and steroids and phospholipids are components of cell membranes. Steroids such as cholesterol decrease membrane fluidity. However, they are not typically sources of energy; in mammals, they are normally metabolized and excreted. Steroids play critical roles in a number of disorders, including malignancies like prostate cancer , where steroid production inside and outside the tumour promotes cancer cell aggressiveness.
The hundreds of steroids found in animals, fungi, and plants are made from lanosterol in animals and fungi; see examples above or cycloartenol in plants. Lanosterol and cycloartenol derive from cyclization of the triterpenoid squalene. Steroid biosynthesis is an anabolic pathway which produces steroids from simple precursors.
A unique biosynthetic pathway is followed in animals compared to many other organisms , making the pathway a common target for antibiotics and other anti-infection drugs. Steroid metabolism in humans is also the target of cholesterol-lowering drugs, such as statins. In humans and other animals the biosynthesis of steroids follows the mevalonate pathway, which uses acetyl-CoA as building blocks for dimethylallyl pyrophosphate DMAPP and isopentenyl pyrophosphate IPP.
Modifications of lanosterol into other steroids are classified as steroidogenesis transformations. DMAPP and IPP donate isoprene units, which are assembled and modified to form terpenes and isoprenoids  a large class of lipids, which include the carotenoids and form the largest class of plant natural products.
Lanosterol can then be converted into other steroids, such as cholesterol and ergosterol. Two classes of drugs target the mevalonate pathway: Steroidogenesis is the biological process by which steroids are generated from cholesterol and changed into other steroids. The major classes of steroid hormones, as noted above with their prominent members and functions , are the Progestogen , Corticosteroids corticoids , Androgens , and Estrogens.
In plants and bacteria, the non-mevalonate pathway uses pyruvate and glyceraldehyde 3-phosphate as substrates. During diseases pathways otherwise not significant in healthy humans can become utilized. These reactions introduce oxygen into the steroid ring, allowing the cholesterol to be broken up by other enzymes into bile acids. Steroid isolation , depending on context, is the isolation of chemical matter required for chemical structure elucidation, derivitzation or degradation chemistry, biological testing, and other research needs generally milligrams to grams, but often more  or the isolation of "analytical quantities" of the substance of interest where the focus is on identifying and quantifying the substance for example, in biological tissue or fluid.
The amount isolated depends on the analytical method, but is generally less than one microgram. In both cases, the isolated substance is purified to chemical homogeneity; combined separation and analytical methods, such as LC-MS , are chosen to be "orthogonal"—achieving their separations based on distinct modes of interaction between substance and isolating matrix—to detect a single species in the pure sample.
Structure determination refers to the methods to determine the chemical structure of an isolated pure steroid, using an evolving array of chemical and physical methods which have included NMR and small-molecule crystallography. Microbial catabolism of phytosterol side chains yields C steroids, C steroids, and ketosteroids i. The semisynthesis of steroids often begins from precursors such as cholesterol ,  phytosterols ,  or sapogenins. Some steroidal hormones are economically obtained only by total synthesis from petrochemicals e.
A number of Nobel Prizes have been awarded for steroid research, including:. From Wikipedia, the free encyclopedia. This is the latest accepted revision , reviewed on 2 April This article is about the family of polycyclic chemical compounds.
For the drugs, also used as performance-enhancing substances, see Anabolic steroid. For the scientific journal, see Steroids journal. The shape of the four rings of most steroids is illustrated carbon atoms in black, oxygens in red and hydrogens in grey. The apolar "slab" of hydrocarbon in the middle grey, black and the polar groups at opposing ends red are common features of natural steroids. This section needs attention from an expert in Pharmacology.
The specific problem is: WikiProject Pharmacology may be able to help recruit an expert. This section needs expansion with: You can help by adding to it. Adrenal gland Batrachotoxin List of steroid abbreviations List of steroids Membrane steroid receptor Pheromone Reverse cholesterol transport Steroidogenesis inhibitor Steroidogenic acute regulatory protein Steroidogenic enzyme. The nomenclature of steroids. Queen Mary University of London. Retrieved 10 May Steroid Chemistry at a Glance.
The New England Journal of Medicine. Retrieved 20 June Rogozkin 14 June Metabolism of Anabolic-Androgenic Steroids. The steroid structural base is a steran nucleus, a polycyclic C17 steran skeleton consisting of three condensed cyclohexane rings in nonlinear or phenanthrene junction A, B, and C , and a cyclopentane ring D. Genome Biology and Evolution. Applied and Environmental Microbiology. Steroids Health and Medical Issues Today.
Skeletal Modification in Revised Section F: Total synthesis of natural products: Natural toxins, coral communities, and symbiotic relationships". The Science of Biology 9th ed.