| Revision as of 15:52, 12 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: {{cascite}} StdInChI StdInChIKey.← Previous edit |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 388697934 |
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| ImageFile = Corticosterone-2D-skeletal.svg |
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| verifiedrevid = 401968208 |
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| ImageSize = |
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| ImageFile1 = Corticosterone_3d.jpg |
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| ImageFile1 = {{wikidata|property|raw|P117}} |
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| ImageFile2 = {{wikidata|property|raw|P8224}} |
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| IUPACName = (11β)-​11,​21-​dihydroxypregn-​4-​ene-​3,​20-​dione |
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| OtherNames = |
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| ImageSize1 = 220 |
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| ImageSize2 = 220 |
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| Section1 = {{Chembox Identifiers |
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| ImageAlt1 = Corticosterone molecule |
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| ChemSpiderID = 5550 |
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| IUPACName = 11β,21-Dihydroxypregn-4-ene-3,20-dione |
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| SystematicName = (1''S'',3a''S'',3b''S'',9a''R'',9b''S'',10''S'',11a''S'')-10-Hydroxy-1-(hydroxyacetyl)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7''H''-cyclopropaphenanthren-7-one |
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| OtherNames = |
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|Section1={{Chembox Identifiers |
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| IUPHAR_ligand = 2869 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 5550 |
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| InChI = 1/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1 |
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| InChI = 1/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1 |
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| InChIKey = OMFXVFTZEKFJBZ-HJTSIMOOBD |
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| InChIKey = OMFXVFTZEKFJBZ-HJTSIMOOBD |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1 |
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| StdInChI = 1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = OMFXVFTZEKFJBZ-HJTSIMOOSA-N |
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| StdInChIKey = OMFXVFTZEKFJBZ-HJTSIMOOSA-N |
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| CASNo = 50-22-6 |
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| CASNo = 50-22-6 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 5753 |
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| PubChem = 5753 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| SMILES = O=C4\C=C2/(1(O)C3((C(=O)CO)CC31CC2)C)(C)CC4 |
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| ChEMBL = 110739 |
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| MeSHName = Corticosterone |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = W980KJ009P |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 16827 |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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| DrugBank = DB04652 |
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| EC_number = 200-019-6 |
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| Beilstein = 2339601 |
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| KEGG = C02140 |
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| SMILES = O=C4\C=C2/(1(O)C3((C(=O)CO)CC31CC2)C)(C)CC4 |
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| MeSHName = Corticosterone |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=21|H=30|O=4 |
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| C=21 | H=30 | O=4 |
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| Appearance = |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| Solubility = |
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| AutoignitionPt = |
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| GHSPictograms = {{GHS07}} |
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| Autoignition = |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|317}} |
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| PPhrases = {{P-phrases|261|272|280|302+352|321|333+313|363|501}} |
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'''Corticosterone''' (CORT) is a 21-carbon ] of the ] type produced in the cortex of the ]s. |
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'''Corticosterone''', also known as '''17-deoxycortisol''' and '''11β,21-dihydroxyprogesterone''',<ref name="HillMakin1991">{{cite book|author1=R.A. Hill|author2=H.L.J. Makin|author3=D.N. Kirk|author4=G.M. Murphy|title=Dictionary of Steroids|url=https://books.google.com/books?id=qw5X0NK1A90C&pg=PA189|date=23 May 1991|publisher=CRC Press|isbn=978-0-412-27060-4|pages=189–}}</ref> is a 21-carbon ] of the ] type produced in the cortex of the ]s. In the very rare case of ] cortisol production is blocked.<ref>{{cite journal|url=http://emedicine.medscape.com/article/117140-overview#a5|title=C-17 Hydroxylase Deficiency: Practice Essentials, Pathophysiology, Epidemiology|date=1 February 2018|via=eMedicine}}</ref> |
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==Roles== |
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==Roles== |
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In many species, including ]s, ]s, ] and ], corticosterone is a main ],<ref name="urle.hormone | The Hormones : Corticoids">{{cite web |url=http://e.hormone.tulane.edu/learning/corticoids.html |title=e.hormone | The Hormones : Corticoids |format= |work= |accessdate=2009-04-09}}</ref> involved in regulation of fuel, ] reactions, and ] responses. |
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In many species, including ]s, ]s, ] and ], corticosterone is a main ],<ref name="urle.hormone | The Hormones : Corticoids">{{cite web |url=http://e.hormone.tulane.edu/learning/corticoids.html |title=e.hormone | The Hormones : Corticoids |access-date=2009-04-09}}</ref> involved in regulation of energy, ] reactions, and ] responses.{{cn|date=June 2024}} |
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However, in ], corticosterone is produced primarily in the ] of the ]. It has only weak ] and ] potencies in humans and is important mainly as an intermediate in the ] from ] to ]. Corticosterone is converted to aldosterone by ], found only in the mitochondria of glomerulosa cells. Glomerulosa cells are found in the ], which is the most superficial region of endocrine cells in the ]. |
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However, in ], ] is the primary glucocorticoid that is produced primarily in the ] of the ]. Corticosterone has only weak ] and ] potencies in humans and is important mainly as an intermediate in the ] from ] to ]. Corticosterone is converted to aldosterone by ], found only in the mitochondria of glomerulosa cells. Glomerulosa cells are found in the ], which is the most superficial region of endocrine cells in the ].{{cn|date=June 2024}} |
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Corticosterone is the precursor molecule to the mineralocorticoid aldosterone, one of the major homeostatic modulators of sodium and potassium levels in vivo.{{cn|date=June 2024}} |
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==Release or generation mechanisms== |
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==Release or generation mechanisms== |
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One example of a release pathway relates to ] stimulation on the skins of certain ]s such as the ], '']''; this trigger seems to cause the internal generation of corticosterone in that species.<ref>C. Michael Hogan (2008) ''Rough-skinned Newt (Taricha granulosa)'', Globaltwitcher, ed. Nicklas Stromberg </ref> |
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One example of a release pathway relates to ] stimulation on the skins of certain ]s such as the ], '']''; this trigger seems to cause the internal generation of corticosterone in that species.<ref>C. Michael Hogan (2008) ''Rough-skinned Newt (Taricha granulosa)'', Globaltwitcher, ed. Nicklas Stromberg {{Webarchive|url=https://web.archive.org/web/20090527153302/http://www.globaltwitcher.com/artspec_information.asp?thingid=43182 |date=2009-05-27 }}</ref> |
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==Corticosterone in birds== |
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==References== |
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A sizable amount of research has been done on the effects of corticosterone in ]. A brief survey of this research is below. |
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{{reflist}} |
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Corticosterone both inhibits ] and degrades ]. Birds with increased levels of corticosterone will have slower ] growth during their molting period and an extended period of poor flight. As a result, many birds have reduced levels of corticosterone when they ] so as to prevent the degradation of their new feathers.<ref>Romero, L.M., Strochlic, D., Wingfield, J.C. (2005). Corticosterone inhibits feather growth: Potential mechanism explaining seasonal down regulation of corticosterone during molt. Comparative Biochemistry and Physiology Part A: Molecular & Integrative Physiology, 142, 65-73.</ref> Interestingly, higher levels of corticosterone are also associated with a wider range of exploration, despite beforementioned inhibited feather growth.<ref>Liebl, A. L., & Martin, L. B. (2012). Exploratory behaviour and stressor hyper-responsiveness facilitate range expansion of an introduced songbird. Proc. R. Soc. B, 279(1746), 4375-4381.</ref> |
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Corticosterone has further developmental effects on birds. Increased levels of corticosterone in chicks leads to increased begging for food and ]. In the short term this leads to higher chance of obtaining food, but in the long term, increased corticosterone in early life compromises the birds cognitive functioning (], association of visual cue with food, etc.).<ref>Kitaysky, A.S., Kitaiskaia, E.V., Piatt, J.F., Wingfield, J.C. (2003). Benefits and costs of increased levels of corticosterone in seabird chicks. Hormones and Behavior, 43, 140-149.</ref> |
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Parental response to increased begging by chicks is an increased time ] for food. This leaves the nest of chicks without protection for increased durations of time.<ref>Kitaysky, A.S., Piatt, J.F., Wingfield, J.C. (2000). Corticosterone facilitates begging and affects resource allocation in the black-legged kittiwake. Behavioral Endocrinology, 12, 619-625.</ref> To counter this, during extended periods of food shortage, chicks of some species may suppress corticosterone activity and thus reduce the negative effects elevated corticosterone induces.<ref>Kitaysky, A.S., Kitaishaia, E.V., Wingfield, J.C., Piatt, J.F. (2001). Dietary restriction causes chronic elevation of corticosterone and enhances stress response in red-legged kittiwake chicks. Journal of Comparative Physiology B, 8, 701-709</ref> |
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==Effect on memory== |
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Corticosterone has multiple effects on ]. The main effects are seen through the impact of ] on emotional memories as well as ] (LTM).{{cn|date=June 2024}} |
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With emotional memories, corticosterone is largely associated with ] memory recognition. Studies have shown that when fear memories are reactivated or consolidated, levels of corticosterone increased. The increase in corticosterone is linked to anxiety relief. This finding depends on the time at which the administration of corticosterone took place as compared to when the fear conditioning took place; corticosterone can either facilitate or interrupt ] fear.<ref>A. Albrecht et al. 2013. Long-Lasting Increase of Corticosterone After Fear Memory Reactivation: Anxiolytic Effects and Network Activity Modulation in the Ventral Hippocampus. Neuropsychopharmacology. 38: 386-394.</ref> |
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Not only does corticosterone have effects on emotional memories but memory ] and ] as well.{{cn|date=June 2024}} |
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With respect to recognition and long term memories, corticosterone has variable effects. Studies show that the modification of certain chemical and brain processes that affect corticosterone levels can also impact stress effects on memory. In studies on rats, the fluctuations of corticosterone concentration are shown to prevent stress' impairment of recognition memory in lower amounts. These lower levels seem to be linked to the rescue of stress-induced attenuation of CA1 long-term ].<ref>H. Tamano et al. 2013. Preventative effect of theanine intake on stress-induced imparirments of hippocampal long-term potentiation and recognition memory. Brain Research Bulletin. 95: 1-6.</ref> When researchers looked at stress effects on LTM, they found many outcomes. In multiple studies, the formation of LTM (tested 24 h later) was found to be enhanced by corticosterone in some studies, while the persistence of LTM (tested at least 1 wk later) was only assisted by corticosterone in the late phase of memory consolidation and ].<ref>S. Moore et al. 2013. Conversion of short-term to long-term memory in the novel object recognition paradigm. Neurobiology of Learning and Memory. 105: 174-185.</ref><ref name="stress">C. Yang et al. 2013. Stress within a Restricted Time Window Selectively Affects the Persistence of Long-Term Memory. PLoS One. 8(3): e59075.</ref> Stress facilitates the consolidation but disrupts the reconsolidation of emotional memory. As mentioned previously, the persistence of LTM is selectively enhanced when stress and corticosterone are administered during the late phase after acquisition, but it is disrupted when stress and corticosterone are administered during the late phase after retrieval of memory.<ref name="stress" /> With regards to the persistence of LTM, there is a restricted time window between acquisition and retrieval where persistence is affected. These studies found that while persistence of LTM is selectively affected based on stage of memory, the formation of LTM is left intact after a certain length of time. Up to this point, studies have not agreed as to whether or not these processes are dependent on corticosterone or what even happens based on corticosterone in these processes and how memory is ultimately affected{{cn|date=June 2024}}. |
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In the end, corticosterone affects many processes in terms of memory as well as different types of memories themselves.{{cn|date=June 2024}} |
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==Additional images== |
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==Additional images== |
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<gallery> |
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<gallery> |
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File:Steroidogenesis.svg|]<ref name="HäggströmRichfield2014">{{cite journal|last1=Häggström|first1=Mikael|last2=Richfield|first2=David|title=Diagram of the pathways of human steroidogenesis|journal=WikiJournal of Medicine|volume=1|issue=1|year=2014|issn=2002-4436|doi=10.15347/wjm/2014.005 |doi-access=free }}</ref> |
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File:Steroidogenesis.svg|] |
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Image:Deoxycorticosterone.svg|] |
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File:11-Deoxycorticosterone.svg|] |
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Image:Aldosterone-2D-skeletal.svg|] |
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File:Aldosterone-2D-skeletal.svg|] |
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</gallery> |
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</gallery> |
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==See also== |
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==References== |
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{{Reflist}} |
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==External links== |
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{{biochem-stub}} |
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{{Cholesterol and steroid intermediates}} |
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{{Corticosteroids}} |
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{{Endogenous steroids}} |
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{{Glucocorticoids and antiglucocorticoids}} |
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{{Mineralocorticoids and antimineralocorticoids}} |
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