Introduction:
The core of steroids is comprised of 20 carbon atoms bonded altogether which take the form of four fused rings: three cyclohexane rings and one cyclopentane ring (the D ring). The steroids differ by the functional groups linked to this four ring core and via the oxidation state of rings. Sterols are special forms of steroids having a hydroxyl group at position-3 and a skeleton derived from the cholestane.
Definition of Steroid:
A steroid is a kind of organic compound which includes a particular arrangement of four cycloalkane rings which are linked to one other. Illustrations of steroids comprise the dietary fat cholesterol, the sex hormones estradiol and testosterone, and the anti-inflammatory drug dexamethasone.
Hundreds of different steroids are found in animals, plants and fungi. All the steroids are made in cells either from the sterols lanosterol (that is, animals and fungi) or from cycloartenol (that is, plants). Both lanosterol and cycloartenol are derived from the cyclisation of the triterpene squalene.
Fig: Definition of Steroid
The IUPAC suggested ring lettering (on left) and atom numbering (on right) of cholestane, a prototypical steroid skeleton. The four rings A-D form the gonane nucleus of the steroid.
The total number of carbons (30) points out its triterpenoid origin.
Fig: Stick model of the steroid lanosterol
Structure of Steroid:
Steroids are the class of organic compounds having a chemical structure which includes the core of gonane or a skeleton derived therefrom. Generally, methyl groups are present at the carbons C-10 and C-13. At carbon C-17 an alkyl side chain might as well be present.
Fig: Structure of Steroid
Gonane is the simplest likely steroid and is comprised of 17 carbon atoms; bonded altogether to form four fused rings. The three cyclohexane rings (that is, designated as rings A, B and C in the figure above right) make the skeleton of phenanthrene; ring D consists of a cyclopentane structure. Therefore, altogether they are termed as cyclopentaphenanthrene.
Generally, steroids encompass a methyl group at the carbons C-10 and C-13 and an alkyl side chain at carbon C-17. Moreover, they differ by the configuration of the side chain, the number of additional methyl groups and the functional groups linked to the rings.
Classification of steroids:
I) Taxonomical/Functional Classification:
Some of the common groups of steroids:
1) Animal steroids:
a) Insect steroids: Such comprise Ecdysteroids like ecdysterone
b) Vertebrate steroids (that is, steroid hormones)
Sex steroids are the subset of sex hormones which generate sex differences or support reproduction. They comprise estrogens, androgens and progestagens.
Corticosteroids comprise glucocorticoids and mineralocorticoids. Glucocorticoids control numerous features of metabolism and immune function, while mineralocorticoids assist in maintaining blood volume and control renal excretion of electrolytes. Most of the medical 'steroid' drugs are corticosteroids.
Anabolic steroids are the class of steroids which interact by androgen receptors to raise muscle and bone synthesis. There are natural and synthetic anabolic steroids. In well-liked language, the term 'steroids' generally refers to anabolic steroids.
Cholesterol that modulates the fluidity of cell membranes and is the main constituent of the plaques associated in atherosclerosis.
2) Plant steroids: Phytosterols and Brassinosteroids
3) Fungus steroids: Ergosterols
II) Structural Classification:
This is mainly based on the chemical composition of the steroids. Illustration from this categorization comprises:
Class Examples Number of carbon atoms
Cholestanes cholesterol 27
Cholanes cholic acid 24
Pregnanes progesterone 21
Androstanes testosterone 19
Estranes estradiol 18
Gonane (or steroid nucleus) is the parent (that is, 17-carbon tetracyclic) hydrocarbon molecule devoid of any alkyl side chains.
Metabolism of Steroid:
Steroids comprise estrogen, cortisol, progesterone and testosterone. Estrogen and progesterone are primarily made in the ovary and in the placenta throughout pregnancy and testosterone in the testes.
Testosterone is as well transformed to estrogen to control the supply of each, in the bodies of both males and females. Some of the neurons and glia in the central nervous system (CNS) express the enzymes which are needed for the local synthesis of pregnane neurosteroids, either de novo or by peripherally-derived sources. The rate-limiting step of steroid synthesis is the transformation of cholesterol to pregnenolone that takes place within the mitochondrion.
Steroid metabolism is the entire set of chemical reactions in organisms which produce, modify, and use steroids. Such metabolic pathways comprise:
Steroid synthesis:
Steroid biosynthesis is the anabolic metabolic pathway which makes steroids from simple precursors. This pathway is taken out in different manners in animals than in most of the other organisms, making the pathway a general target for antibiotics and other anti-infective drugs. Moreover, steroid metabolism in humans is the target of cholesterol-lowering drugs like Statins.
It begins in the mevalonate pathway in humans, having Acetyl-CoA as building blocks that form DMAPP and IPP. In the given steps, DMAPP and IPP form lanosterol, the primary steroid.
Fig: Steroid synthesis
The simplified version of latter portion of steroid synthesis pathway, where the intermediates isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) makes geranyl pyrophosphate (GPP), squalene and lastly, lanosterol, the primary steroid in the pathways.
=> Mevalonate pathway:
The mevalonate pathway or HMG-CoA reductase pathway begins by and ends by the dimethylallyl pyrophosphate (DMAPP) and isopentenyl pyrophosphate (IPP). Some key enzymes can be activated via DNA transcriptional regulation on activation of SREBP (that is, Sterol Regulatory Element-Binding Protein-1 and -2). This intracellular sensor detects the low cholesterol levels and stimulates endogenous production through the HMG-CoA reductase pathway, and also increasing lipoprotein uptake through up-regulating the LDL receptor. Regulation of this pathway is as well accomplished via controlling the rate of translation of the mRNA, degradation of the reductase and phosphorylation.
Fig: Mevalonate pathway
=> Pharmacology:
The number of drugs targets the mevalonate pathway:
=> Plants and bacteria:
In plants and bacteria, the non-mevalonate pathway employs pyruvate and glyceraldehyde 3-phosphate as substrates.
=> DMAPP to lanosterol:
Isopentenyl pyrophosphate and dimethylallyl pyrophosphate contribute isoprene units that are assembled and altered to form Terpenes and Isoprenoids that are a big class of lipids which comprise the carotenoids, and make the biggest class of plant natural products.
Here, the isoprene units are linked altogether to form squalene and then folded up and formed to a set of rings to make lanosterol. Lanosterol can then be transformed to other steroids like cholesterol and ergosterol.
Steroidogenesis:
Steroidogenesis is the biological procedure through which steroids are produced from cholesterol and converted into other steroids. The pathways of Steroidogenesis differ between various species; however the pathways of human Steroidogenesis are illustrated in the figure shown below.
Lanosterol can then be transformed to other steroids like cholesterol and ergosterol.
Fig: Pathways of human Steroidogenesis
Products of Steroidogenesis comprise:
Degradation and elimination of Steroids:
Steroids are mostly oxidized through cytochrome P450 oxidase enzymes, like CYP3A4. Such reactions introduce oxygen to the steroid ring and let the structure to be broken up by other enzymes, to make bile acids as final products. Such bile acids can then be removed via secretion from the liver in the bile. The expression of this oxidase gene can be up-regulated via the steroid sensor PXR whenever there is a high blood concentration of the steroids.
Tutorsglobe: A way to secure high grade in your curriculum (Online Tutoring)
Expand your confidence, grow study skills and improve your grades.
Since 2009, Tutorsglobe has proactively helped millions of students to get better grades in school, college or university and score well in competitive tests with live, one-on-one online tutoring.
Using an advanced developed tutoring system providing little or no wait time, the students are connected on-demand with an expert at www.tutorsglobe.com. Students work one-on-one, in real-time with a tutor, communicating and studying using a virtual whiteboard technology. Scientific and mathematical notation, symbols, geometric figures, graphing and freehand drawing can be rendered quickly and easily in the advanced whiteboard.
Free to know our price and packages for online chemistry tutoring. Chat with us or submit request at [email protected]
tutorsglobe.com arrangement of floral organs assignment help-homework help by online description of a flower tutors
Positive Feedback tutorial all along with the key concepts of Nyquist Criterion, Gain and Phase Margins, stability of feedback amplifier, Nyquist criterion for stability, Nyquist curve, Barkhausen criterion for oscillation
The transfer prices might be fixed on the basis of 'Negotiated Prices' that are fixed by negotiations among the selling and the buying division.
Theory of Searching and their types including the key concepts of Binary Search, Binary Search Tree, Variations on Binary Trees, Dictionary, Collision Handling and Hash Table variations
Cost reduction programme aims at improvement of human efforts at all levels of the organisation which help in reducing costs.
Introduction to Quantum Chemistry tutorial all along with the key concepts of History of Quantum Mechanics, Electronic structure, Wave model, Valence bond, Molecular orbital, Density functional theory, Chemical dynamics, Adiabatic chemical dynamics
tutorsglobe.com factors affecting viscosity assignment help-homework help by online viscosity tutors
tutorsglobe.com structure of cell membrane assignment help-homework help by online cell membrane tutors
tutorsglobe.com change of electron affinity along a period assignment help-homework help by online electron affinity tutors
build up the layout of a lap winding for a 3 phase ac machine comprising 4 pole and 24 slots. there are 2 coil sides per slot.
Millman Theorem and Nortons Theorem tutorial all along with the key concepts of Calculation of a Norton equivalent circuit, Ohm's Law and Reciprocity
tutorsglobe.com objectives of fiscal policy assignment help-homework help by online fiscal policy tutors
Cellular Response tutorial all along with the key concepts of Properties of Innate Immune Response, Properties of Adaptive Immune Response, Kinds of Adaptive Immune Response, Active and Passive Immunity, Genetics of response to antigenic stimulation, Clonal Selection Theory
tutorsglobe.com entropy assignment help-homework help by online chemical thermodynamics tutors
Halides and oxides of group 15 elements tutorial all along with the key concepts of Introduction to Halides group, Trihalides, Pentahalides, Introduction of Oxides group, Oxides of Nitrogen, Resonance Structures of Nitric Oxide, Oxides of Phosphorus, Arsenic, Antimony and Bismuth
1960049
Questions Asked
3689
Tutors
1466652
Questions Answered
Start Excelling in your courses, Ask an Expert and get answers for your homework and assignments!!