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Encyclopedia > 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. Crystal structure of human sex hormone-binding globulin, transporting 5α-dihydrotestosterone. ... Image File history File links Download high resolution version (1100x621, 17 KB) [[PD-self}} File links The following pages link to this file: Lanosterol User:Benjah-bmm27/Gallery ... Image File history File links Download high resolution version (1100x621, 17 KB) [[PD-self}} File links The following pages link to this file: Lanosterol User:Benjah-bmm27/Gallery ... Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived. ... Terpenes are a class of hydrocarbons, produced by many plants, particularly conifers. ... Chemical structure of the terpenoid isopentenyl pyrophosphate. ... Some common lipids. ... For other uses, see Carbon (disambiguation). ...


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] In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... The most fundamental reactions in chemistry are the redox processes. ... For other uses, see Plant (disambiguation). ... For other uses, see Animal (disambiguation). ... For the fictional character, see Fungus the Bogeyman. ... Sterols, or steroid alcohols are a subgroup of steroids with a hydroxyl group in the 3-position of the A-ring. ... Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived. ... Cycloartenol is a sterol precursor in photosynthetic organisms and plants. ... Terpenes are a class of hydrocarbons, produced by many plants, particularly conifers. ... Squalene is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanic sources as well, including amaranth seed, rice bran, wheat germ, and olives. ...

Contents

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] Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... Chemical structure of isopentenyl pyrophosphate. ... Structure of dimethyallyl pyrophosphate Dimethylallyl pyrophosphate (or -diphosphate) (DMAPP) is an intermediate product of both mevalonic acid (MVA) pathway and DOXP/MEP pathway. ... Chemical structure of geranyl pyrophosphate. ... Squalene is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanic sources as well, including amaranth seed, rice bran, wheat germ, and olives. ... Estriol. ... Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. ... Testosterone is a steroid hormone from the androgen group. ... // For ovary as part of plants see ovary (plants) An ovary is an egg-producing reproductive organ found in female organisms. ... The placenta (Latin for cake, referencing its appearance in humans) is an ephemeral organ present in placental vertebrates, such as eutherial mammals and sharks during gestation (pregnancy). ... Testosterone is a steroid hormone from the androgen group. ... Human male anatomy The testicles, known medically as testes (singular testis), are the male generative glands in animals. ... Neurons (also called nerve cells) are the primary cells of the nervous system. ... Neuroglia cells of the brain shown by Golgis method. ... A diagram showing the CNS: 1. ... Neuraminidase ribbon diagram An enzyme (in Greek en = in and zyme = blend) is a protein, or protein complex, that catalyzes a chemical reaction and also controls the 3D orientation of the catalyzed substrates. ... Pregnane is, indirectly, a parent of progesterone. ... Apart from exerting effects on the genome via intracellular steroid receptors, neuroactive steroids (or neurosteroids) rapidly alter neuronal excitability through interaction with neurotransmitter-gated ion channels. ... In general usage, de novo is a Latin expression meaning afresh, anew, beginning again. In USA Banking, a de novo bank is defined as a state member bank that has been in operation for five years or less. ... Cholesterol is a sterol (a combination steroid and alcohol). ... Pregnenolone is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens. ... Electron micrograph of a mitochondrion showing its mitochondrial matrix and membranes In cell biology, a mitochondrion (plural mitochondria) is a membrane-enclosed organelle that is found in most eukaryotic cells. ...


Classification

Taxonomical/Functional

Some of the common categories of steroids:

Orders Subclass Apterygota Archaeognatha (bristletails) Thysanura (silverfish) Subclass Pterygota Infraclass Paleoptera (Probably paraphyletic) Ephemeroptera (mayflies) Odonata (dragonflies and damselflies) Infraclass Neoptera Superorder Exopterygota Grylloblattodea (ice-crawlers) Mantophasmatodea (gladiators) Plecoptera (stoneflies) Embioptera (webspinners) Zoraptera (angel insects) Dermaptera (earwigs) Orthoptera (grasshoppers, etc) Phasmatodea (stick insects) Blattodea (cockroaches) Isoptera (termites) Mantodea (mantids) Psocoptera... Ecdysterone (Eck-die-stare-own) or 20-Beta-Hydroxyecdysterone is an herbal extract that promotes a highly anabolic environment within the body resulting in numerous performance enhancing benefits. ... This article does not cite any references or sources. ... Steroid hormones are steroids which act as hormones. ... Sex steroids, also known as gonadal steroids, are steroid hormones which interact with vertebrate androgen or estrogen receptors. ... Sex hormones are hormones that affect the reproductive system. ... This article is about the development of sexual dimorphisms in humans. ... For other uses, see Reproduction (disambiguation) Reproduction is the biological process by which new individual organisms are produced. ... Androgen is the generic term for any natural or synthetic compound, usually a steroid hormone, that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors. ... Estriol. ... Progestagens (also spelled progestogens or gestagens) are hormones which produce effects similar to progesterone, the only natural progestagen. ... In physiology, corticosteroids are a class of steroid hormones that are produced in the adrenal cortex. ... Glucocorticoids are a class of steroid hormones characterised by an ability to bind with the cortisol receptor and trigger similar effects. ... Mineralocorticoids is a class of steroids characterised by their similarity to aldosterone and their influence on salt and water metabolism. ... Glucocorticoids are a class of steroid hormones characterised by an ability to bind with the cortisol receptor and trigger similar effects. ... Structure of the coenzyme adenosine triphosphate, a central intermediate in energy metabolism. ... A scanning electron microscope image of a single neutrophil (yellow), engulfing anthrax bacteria (orange). ... Mineralocorticoids is a class of steroids characterised by their similarity to aldosterone and their influence on salt and water metabolism. ... The kidneys are the organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... An electrolyte is any substance containing free ions that behaves as an electrically conductive medium. ... Crystal structure of human sex hormone-binding globulin, transporting 5α-dihydrotestosterone. ... Cholesterol is a sterol (a combination steroid and alcohol). ... Drawing of a cell membrane A component of every biological cell, the cell membrane (or plasma membrane) is a thin and structured bilayer of phospholipid and protein molecules that encapsulate the cell. ... β-sitosterol Ergosterol. ... Brassinolide appears to be the most common Brassinosteroid. ... Ergosterol (ergosta-5,7,22-trien-3β-ol), a sterol, is the biological precursor to Vitamin D2. ...

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 Wikipedia MeSH catalog. Examples from this classification include: For other uses, see Mesh (disambiguation). ...

Class Examples Number of carbon atoms
Cholstanes cholesterol 27
Cholanes cholic acid 22
Pregnanes progesterone 21
Androstanes testosterone 19
Estranes estradiol 18

Cholesterol is a sterol (a combination steroid and alcohol). ... Cholic acid Cholic acid is a bile acid, a white crystalline substance insoluble in water. ... Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. ... Testosterone is a steroid hormone from the androgen group. ... Estradiol (17β-estradiol) (also oestradiol) is a sex hormone. ...

See also

Batrachotoxins are extremely potent cardiotoxic and neurotoxic steroidal alkaloids found in certain species of frogs (poison dart frog), Melyridae beetles and birds (Pitohui, Ifrita kowaldi). ... The steroid hormones are referred to by various abbreviations in the biological literature. ... Simplified version of latter part of steroid synthesis pathway, where the intermediates isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) form geranyl pyrophosphate (GPP), squalene and, finally, lanosterol, the first steroid in the pathways. ...

References

  1. ^ Lanosterol biosynthesis
  2. ^ 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. 

A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

Further reading

  • G. P. Moss (1989). "Nomenclature of Steroids (Recommendations 1989)". Pure & Appl. Chem. 61 (10): 1783-1822. 

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)
Many terpenes are derived from conifer resins, here a pine. ... In chemistry, hydrophobic or lipophilic species, or hydrophobes, tend to be electrically neutral and nonpolar, and thus prefer other neutral and nonpolar solvents or molecular environments. ... The cell membrane (also called the plasma membrane, plasmalemma or phospholipid bilayer) is a selectively permeable lipid bilayer found in all cells. ... In biology, signal transduction refers to any process by which a cell converts one kind of signal or stimulus into another, most often involving ordered sequences of biochemical reactions inside the cell, that are carried out by enzymes and linked through second messengers resulting in what is thought of as... Squalene is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanic sources as well, including amaranth seed, rice bran, wheat germ, and olives. ... Lanosterol is a tetracyclic triterpenoid which is the compound from which all steroids are derived. ... Cholesterol is a sterol (a combination steroid and alcohol). ... Pregnenolone is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens. ... 17-Hydroxypregnenolone (also 17-OH-pregnenolone and 17α-hydroxypregnenolone), is a C21 steroid that is obtained by hydroxylation of pregnenolone at the C17α position. ... Dehydroepiandrosterone (DHEA), is a natural steroid prohormone produced from cholesterol by the adrenal glands, the gonads, adipose tissue, brain and in the skin (by an autocrine mechanism)]. DHEA is the precursor of androstenedione, testosterone and estrogen. ... Androstenedione (also known as 4-androstenedione) is a 19-carbon steroid hormone produced in the adrenal glands and the gonads as an intermediate step in the biochemical pathway that produces the androgen testosterone and the estrogens estrone and estradiol. ... Estriol. ... Estradiol (17β-estradiol) (also oestradiol) is a sex hormone. ... Chemical structure of estriol Estriol (also oestriol) is one of the three main estrogens produced by the human body. ... Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. ... Androgen is the generic term for any natural or synthetic compound, usually a steroid hormone, that stimulates or controls the development and maintenance of masculine characteristics in vertebrates by binding to androgen receptors. ... Testosterone is a steroid hormone from the androgen group. ... For other uses, see DHT (disambiguation). ... Androsterone(ADT) is a steroid hormone with weak androgenic activity. ... Progestagens (also spelled progestogens or gestagens) are hormones similar in effect to progesterone, the only natural progestagen. ... Progesterone is a C-21 steroid hormone involved in the female menstrual cycle, pregnancy (supports gestation) and embryogenesis of humans and other species. ... 17-hydroxyprogesterone ( also 17-OH progesterone, or 17OHP))is a C-21 steroid that is derived from progesterone by 17-hydroxylase, a P450c17 enzyme, and is a prohormone for both glucocorticoids and androstenedione, a precursor for sex steroids. ... Progestagens (also spelled progestogens or gestagens) are hormones similar in effect to progesterone, the only natural progestagen. ... Glucocorticoids are a class of steroid hormones characterised by an ability to bind with the cortisol receptor and trigger similar effects. ... Cortisol is a corticosteroid hormone produced by the Zona fasciculata of the adrenal cortex (in the adrenal gland). ... Prednisone is a synthetic corticosteroid drug which is usually taken orally but can be delivered by intramuscular injection and can be used for a great number of different conditions. ... Mineralocorticoids is a class of steroids characterised by their similarity to aldosterone and their influence on salt and water metabolism. ... Aldosterone, is a steroid hormone (mineralocorticoid family) produced by the outer-section (zona glomerulosa) of the adrenal cortex in the adrenal gland, and acts on the kidney nephron to conserve sodium, secrete potassium,increase water retention, and increase blood pressure. ... β-sitosterol Ergosterol. ... β-sitosterol Phytosterols (also called plant sterols) are a group of steroid alcohol, phytochemicals naturally occuring in plants. ... Brassicasterol (24-methyl cholest-5,22-dien-3β-ol) A 28 carbon sterol synthesised by several unicellular algae (phytoplankton) and some terrestrial plants oilseed rape. ... Ergosterol (ergosta-5,7,22-trien-3β-ol), a sterol, is the biological precursor to Vitamin D2. ... Ergosterol (ergosta-5,7,22-trien-3β-ol), a sterol, is the biological precursor to Vitamin D2. ... Ergocalciferol (Deltalin®, Eli Lilly and Company) is a form of Vitamin D, also called vitamin D2. ... Wöhler observes the synthesis of urea. ... Peptides (from the Greek πεπτος, digestible), are the family of short molecules formed from the linking, in a defined order, of various α-amino acids. ... This article is about the class of chemicals. ... Look up nucleic acid in Wiktionary, the free dictionary. ... Lactose is a disaccharide found in milk. ... Nucleotide sugars are biochemicals that act as donors of sugar residues in nucleotide sugars metabolism. ... Some common lipids. ... Many terpenes are derived from conifer resins, here a pine. ... The orange ring surrounding Grand Prismatic Spring is due to carotenoid molecules, produced by huge mats of algae and bacteria. ... Polypyrrole A Polypyrrole (PPy) is a chemical compound formed from a number of connected pyrrole ring structures. ... A cofactor is any substance that needs to be present in addition to an enzyme to catalyze a certain reaction. ... Molecular structure of the flavone backbone (2-phenyl-1,4-benzopyrone) The term flavonoid refers to a class of plant secondary metabolites. ... Chemical structure of ephedrine, a phenethylamine alkaloid An alkaloid is a nitrogen-containing naturally occurring compound, produced by a large variety of organisms, including fungi, plants, animals, and bacteria. ... Polyketides are secondary metabolites from bacteria, fungi, plants, and animals. ... A glycoside is a molecule where a sugar group is bonded through its anomeric carbon to a nonsugar group by either an oxygen or a nitrogen atom. ...

  Results from FactBites:
 
Steroid Encyclopaedia - the ultimate guide to anabolic steroids (1253 words)
In general, steroid users find that their first cycle is the most dramatic in terms of the gains that they make.
Veterinarian steroids do not have to meet the exact same sanitary specifications that human pharmaceuticals do; however, they are generally made under sanitary conditions.
Many steroid users develop an attitude that if they are not taking any steroids they are simply not making any gains, and to justify even training they will use small amounts of steroids between their cycles.
Steroid - Wikipedia, the free encyclopedia (481 words)
A steroid is a lipid characterized by a carbon skeleton with four fused rings.
All steroids are derived from the acetyl CoA biosynthetic pathway.
Steroids and retinoids are both terpenes which are hydrophobic, pass through cell membranes and bind to intracellular receptors.
  More results at FactBites »

 
 

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