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{{chembox |
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{{chembox |
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| verifiedrevid = 407466303 |
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| verifiedrevid = 443583337 |
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|ImageFile=desmosterol.png |
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| ImageFile =desmosterol.png |
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|ImageSize=200px |
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| ImageAlt = Skeletal formula of desmosterol |
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|IUPACName=(3''S'',8''S'',9''S'',10''R'',13''R'',14''S'',17''R'')-10,13-dimethyl-17--2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1''H''-cyclopentaphenanthren-3-ol |
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| ImageFile1 = Desmosterol 3D ball.png |
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|OtherNames=Cholesta-5,24-dien-3β-ol |
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| ImageAlt1 = Ball-and-stick model of the desmosterol molecule |
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| IUPACName = Cholesta-5,24-dien-3β-ol |
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| SystematicName = (1''R'',3a''S'',3b''S'',7''S'',9a''R'',9b''S'',11a''R'')-9a,11a-Dimethyl-1--2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1''H''-cyclopentaphenanthren-7-ol |
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| OtherNames = |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| IUPHAR_ligand = 2748 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 388662 |
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| ChemSpiderID = 388662 |
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| InChI = 1/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1 |
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| InChI = 1/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1 |
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| StdInChIKey = AVSXSVCZWQODGV-DPAQBDIFSA-N |
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| StdInChIKey = AVSXSVCZWQODGV-DPAQBDIFSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=313-04-2 |
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| CASNo =313-04-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=439577 |
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| ChEBI = 17737 |
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| UNII = ANP93865R8 |
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| PubChem =439577 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17737 |
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| SMILES = O4C/C3=C/C1(CC2(1CC2(C)CC\C=C(/C)C)C)3(C)CC4 |
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| SMILES = O4C/C3=C/C1(CC2(1CC2(C)CC\C=C(/C)C)C)3(C)CC4 |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>27</sub>H<sub>44</sub>O |
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| Formula =C<sub>27</sub>H<sub>44</sub>O |
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| MolarMass=384.64 g/mol |
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| MolarMass =384.64 g/mol |
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| Appearance=White powder |
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| Appearance =White powder |
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| Density= |
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| MeltingPt=121.5º C |
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| MeltingPtC = 121.5 |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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| FlashPt = |
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| AutoignitionPt = |
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'''Desmosterol''' (Cholesta-5,24-dien-3β-ol) is a ] present in the membrane of ] and an intermediate product in cholesterol synthesis in mammal cells.<ref>{{cite journal |last1=Kamal |first1=Md. Arif |last2=Pal |first2=Antara |title=Effect of Desmosterol, Lathosterol and Coprostanol on the phase behaviour of phospholipid membranes |journal=Colloids and Surfaces A: Physicochemical and Engineering Aspects |date=September 2023 |volume=673 |pages=131489 |doi=10.1016/j.colsurfa.2023.131489 }}</ref> Structurally, desmosterol has a similar backbone to ], with the exception of an additional double bond in the structure of desmosterol. |
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'''Desmosterol''' is a molecule similar to ]. It is accumulated in ]. |
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The similarity can be seen biologically through the synthesis of cholesterol in the human body, as desmosterol is the immediate precursor to cholesterol in the ].<ref>{{cite journal |last1=Bloch |first1=Konrad |title=The Biological Synthesis of Cholesterol |journal=Science |date=October 1965 |volume=150 |issue=3692 |pages=19–28 |doi=10.1126/science.150.3692.19 |pmid=5319508 |bibcode=1965Sci...150...19B }}</ref> Desmosterol is accumulated in ] and undergoes reduction with the catalyst '']'' to form cholesterol.<ref>{{cite journal |last1=Keber |first1=Rok |last2=Rozman |first2=Damjana |last3=Horvat |first3=Simon |title=Sterols in spermatogenesis and sperm maturation |journal=Journal of Lipid Research |date=January 2013 |volume=54 |issue=1 |pages=20–33 |doi=10.1194/jlr.R032326 |doi-access=free |pmc=3520525 |pmid=23093550 }}</ref> |
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In 2014, desmosterol was named the ] 2012 by the International Society for Molecular and Cell Biology and Biotechnology Protocols and Researches (]).<ref>{{Cite web |title=Announcing ISMCBBPR's Molecule of the Year 2012 |url=http://www.scientistsolutions.com/t29256-announcing+ismcbbpr_s+molecule+of+the+year+2012.html |url-status=dead |archive-url=https://web.archive.org/web/20150924095328/http://www.scientistsolutions.com/t29256-announcing+ismcbbpr_s+molecule+of+the+year+2012.html |archive-date=2015-09-24 |access-date=2014-02-22}}</ref> |
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== Background == |
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Desmosterol is classified as a cholestadienol, a subgroup of a wider known group of ]s, which naturally occur in eukaryotes. The presence of desmosterol in oceans and lakes has the potential to diagnose ] conditions and to study trends in steroid chemistry during the early stages of ].<ref name=":0">{{Cite journal |last1=Smith |first1=D.J. |last2=Eglinton |first2=G. |last3=Morris |first3=R.J. |last4=Poutanen |first4=E.L. |date=1983 |title=Aspects of the steroid geochemistry of an interfacial sediment from the Peruvian upwelling |journal=Oceanologica Acta |volume=6 |issue=2 |pages=211–219 |url=https://archimer.ifremer.fr/doc/00114/22476/20157.pdf }}</ref> Desmosterol has been found in high yields in samples of ''Rhizosolenia setigera'' (Brightwell) in Western Svalbard,<ref name=":12">{{cite journal |last1=Belt |first1=Simon T. |last2=Brown |first2=Thomas A. |last3=Smik |first3=Lukas |last4=Tatarek |first4=Agnieszka |last5=Wiktor |first5=Józef |last6=Stowasser |first6=Gabriele |last7=Assmy |first7=Philipp |last8=Allen |first8=Claire S. |last9=Husum |first9=Katrine |title=Identification of C25 highly branched isoprenoid (HBI) alkenes in diatoms of the genus Rhizosolenia in polar and sub-polar marine phytoplankton |journal=Organic Geochemistry |date=August 2017 |volume=110 |pages=65–72 |doi=10.1016/j.orggeochem.2017.05.007 |bibcode=2017OrGeo.110...65B |hdl=10026.1/9642 |url=http://nora.nerc.ac.uk/id/eprint/517076/1/Identification%20of%20C25%20highly%20branched%20isoprenoid%20%28HBI%29%20alkenes%20AAM.pdf |hdl-access=free }}</ref> and from surface sediment off of the Peruvian Shelf sediment-water interface.<ref name=":0" /> |
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In 1955, desmosterol was first described and isolated from chick embryo sterol with a 2% yield and was postulated as being a biological precursor to cholesterol by Stokes et al.<ref>{{Cite journal |last1=Stokes |first1=W. M. |last2=Fish |first2=W. A. |last3=Hickey |first3=F. C. |date=May 1956 |title=Metabolism of cholesterol in the chick embryo. II. Isolation and chemical nature of two companion sterols |journal=The Journal of Biological Chemistry |volume=220 |issue=1 |pages=415–430 |doi=10.1016/S0021-9258(18)65366-9 |pmid=13319360 |doi-access=free }}</ref> The first known isolation of desmosterol in invertebrates was published in 1957 by Fagerlund and Idler.<ref name=":22">{{cite journal |last1=Fagerlund |first1=U. H. M. |last2=Idler |first2=D. R. |title=Marine Sterols. IV. 24-Dehydrocholesterol: Isolation from a Barnacle and Synthesis by the Wittig Reaction |journal=Journal of the American Chemical Society |date=December 1957 |volume=79 |issue=24 |pages=6473–6475 |doi=10.1021/ja01581a030 }}</ref> This new sterol was isolated in large amounts from ], a ] species found on the North American Pacific coast. Additionally, small amounts of desmosterol have been found in other crustaceans such as lobster and shrimp in the '']'' and '']'' species'''.''' This strengthens the conclusion that desmosterol must be created exogenously, as crustaceans have not been seen to ]e sterols.<ref>{{Cite book |last=Gagosian |first=Robert |title=Summary of Investigations Conducted in 1974 |publisher=Woods Hole Oceanographic Institution |year=1974 |location=Massachusetts |pages=C-16}}</ref> |
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== Biological occurrence == |
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Desmosterol has been largely found within a large population of marine invertebrates. Major sources include ]s,<ref name=":22"/> ],<ref name=":4" /> ]a,<ref>{{cite journal |last1=Kobayashi |first1=Masaru |last2=Nishizawa |first2=Motohito |last3=Todo |first3=Kagemi |last4=Mitsuhashi |first4=Hiroshi |title=Marine Sterols. I. Sterols of Annelida, Pseudopotamilla occelata MOORE |journal=Chemical and Pharmaceutical Bulletin |date=1973 |volume=21 |issue=2 |pages=323–328 |doi=10.1248/cpb.21.323 |doi-access=free }}</ref> and ].<ref>{{cite journal |last1=Idler |first1=D.R. |last2=Wiseman |first2=P. |title=Sterols of molluscs |journal=International Journal of Biochemistry |date=October 1971 |volume=2 |issue=11 |pages=516–528 |doi=10.1016/0020-711X(71)90021-8 }}</ref> This has led to the idea of an ] origin of desmosterol in phytoplankton. In 1967, desmosterol was also identified in large percentages in the red algae ], Polusiphonia nigrescens, ], and ] after previously having been undetected. |
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In the 1968 paper by Idler, Saito and Wiseman,<ref name=":4">{{cite journal |last1=Idler |first1=D |last2=Saito |first2=A |last3=Wiseman |first3=P |title=Sterols in red algae (Rhodophyceae)1 |journal=Steroids |date=April 1968 |volume=11 |issue=4 |pages=465–473 |doi=10.1016/S0039-128X(68)80062-5 |pmid=5643148 }}</ref> ] samples were analysed and the sterols present were determined by ]. Samples were collected near Grand Manan Island, New York in 1964 and 1965, and showed a significant difference in the presence of desmosterol. Samples 1 and 2 were from the same source, as were samples 3 and 4, and all samples were harvested at different times. Samples 2, 3, and 4 had the major sterol as desmosterol, compared to sample 1, with the major sterol being cholesterol.<ref name=":4"/> This indicates a 70% difference in desmosterol composition in the sterol samples (1 and 2) over a period of one year. There has been no conclusive evidence to show whether seasonal variation of sterols in barnacles occur. |
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== Biosynthesis == |
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There are two major pathways for cholesterol biosynthesis, being the Kandutsch-Russell and Bloch pathways.<ref>{{Cite journal |last1=Singh |first1=Pushpendra |last2=Saxena |first2=Roopali |last3=Srinivas |first3=Gunda |last4=Pande |first4=Gopal |last5=Chattopadhyay |first5=Amitabha |date=2013-03-15 |editor-last=Koval |editor-first=Michael |title=Cholesterol Biosynthesis and Homeostasis in Regulation of the Cell Cycle |journal=PLOS ONE |language=en |volume=8 |issue=3 |pages=e58833 |doi=10.1371/journal.pone.0058833 |pmid=23554937 |pmc=3598952 |bibcode=2013PLoSO...858833S |doi-access=free }}</ref> The Bloch pathway, named after ], occurs naturally alongside the ] pathway in humans within the cell. The discovery of this pathway led Bloch, joint with ], to receive a Nobel Prize in Physiology or Medicine in 1964. The award was awarded “for their discoveries concerning the mechanism and regulation of the cholesterol and fatty acid metabolism”.<ref>{{Cite web |title=The Nobel Prize in Physiology or Medicine 1964 |url=https://www.nobelprize.org/prizes/medicine/1964/bloch/facts/ |access-date=2023-05-21 |website=NobelPrize.org |language=en-US}}</ref> |
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== Preservation == |
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Desmosterol has been seen to be present in ]s as a ]. However, bacterial symbiont sterol 24-C-methyltransferases is capable of the alkylation of desmosterol to other sponge biomarkers, 24-isopropenylcholesterol, and 24-isopropylidenecholesterol.<ref>{{cite bioRxiv |last1=Brown |first1=Malory O. |last2=Olagunju |first2=Babatunde O. |last3=Giner |first3=José-Luis |last4=Welander |first4=Paula V. |title=Bacterial sterol methylation confounds eukaryotic biomarker interpretations |date=16 May 2022 |biorxiv=10.1101/2022.05.16.491679 }}</ref> There is insignificant data which shows that desmosterol has good ]. |
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== Use as a Biomarker == |
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As a biomarker, desmosterol is important for the ''Chaetoceros calcitrans''<ref>{{cite journal |title=Comp. biochem. physiol. |journal=Comparative Biochemistry and Physiology |date=June 1963 |volume=9 |issue=2 |pages=160 |doi=10.1016/0010-406x(63)90020-3 }}</ref> and ''R. setigera'' and ''N. closterium''<ref name=":5">{{cite journal |last1=Barrett |first1=Stephanie M. |last2=Volkman |first2=John K. |last3=Dunstan |first3=Graeme A. |last4=LeRoi |first4=Jeannie-Marie |title=Sterols of 14 species of marine diatoms (Bacillariophyta) |journal=Journal of Phycology |date=June 1995 |volume=31 |issue=3 |pages=360–369 |doi=10.1111/j.0022-3646.1995.00360.x |bibcode=1995JPcgy..31..360B |s2cid=84292971 }}</ref> ]s as well as ].<ref>{{cite journal |title=Handbook of Psychopharmacology. Edited by L. L. Iversen, S. D. Iversen and S. H. Snyder. Plenum Press: New York. 1978. - Volume 7Principles of Behavioral Pharmacology. (Pp. 453; illustrated; $34.50.) Plenum Press: New York. 1978. - Volume 8Drugs, Neurotransmitters, and Behavior. (Pp. 590; illustrated; $39.50.) Plenum Press: New York. 1978. - Volume 9Chemical Pathways in the Brain. (Pp. 410; illustrated; $29.50.) Plenum Press: New York. 1978. - Volume 10Neuroleptics and Schizophrenia. (Pp. 250; illustrated; $25.00.) Plenum Press: New York. 1978. - Volume 11Stimulants. (Pp. 476; illustrated; $32.50.) Plenum Press: New York. 1978. - Volume 12Drugs of Abuse. (Pp. 420; illustrated; $32.50.) Plenum Press: New York. 1978. - Volume 13Biology of Mood and Anti-anxiety Drugs. (Pp. 440; illustrated; $32.50.) Plenum Press: New York. 1978. - Volume 14Affective Disorders: Drug Actions in Animals and Man. (Pp. 379; illustrated; $29.50.) Plenum Press: New York. 1978. |journal=Psychological Medicine |date=February 1979 |volume=9 |issue=1 |pages=194–195 |doi=10.1017/s0033291700021735 }}</ref> However, desmosterol has the potential to be used as a ] marker for diatoms where it exists as the dominant sterol, such as in ''Rhizosolenia''.<ref name=":5" /> |
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=== Balsfjorden, Northern Norway === |
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Desmosterol has been used as a biomarker for the presence of ]s. The phytoplankton bloom of ''P. pouchetii'' and ''Thalassiosira decipiens'' resulted in low amounts of desmosterol at maximum chlorophyll levels, indicating the low abundance and efficient removal of copepods in these phytoplankton.<ref>{{Cite journal |last1=Hamm |first1=Christian |last2=Reigstad |first2=Marit |last3=Riser |first3=Christian Wexels |last4=Mühlebach |first4=Anneke |last5=Wassmann |first5=Paul |date=2001 |title=On the trophic fate of Phaeocystis pouchetii.: VII. Sterols and fatty acids reveal sedimentation of P. pouchetii-derived organic matter via krill fecal strings |journal=Marine Ecology Progress Series |volume=209 |pages=55–69 |doi=10.3354/meps209055 |jstor=24863836 |doi-access=free }}</ref> |
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=== Peruvian Shelf === |
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Diatoms and Silicoflagellates are classes of phytoplankton present in sedimentary material from the sediment water interface in the Peruvian Shelf region.<ref name=":0"/> Mineralogical analysis of this sedimentary material suggested large volumes of phytoplankton. Researchers at the University of Bristol examined the sterol composition of these sedimentary rocks which have gone through oxygen depletion, leading to anoxic conditions. These conditions have enhanced the preservation of lipids present during the time of formation, around 1 year prior, and have limited the degradation of these compounds. |
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== Measurement techniques == |
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Desmosterol has seen to be identified most commonly through chemical constants, ], ], ], and ] techniques.<ref name=":4"/> The use of thin-layer and gas-liquid chromatography to measure desmosterol is less common with the development of more advanced techniques. |
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=== GC-MS === |
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Samples from water sources are first extracted and partially purified before analysis. Sterols are commonly first derivatised after purification. Lipid extracts can be separated into their fragments by ionisation using Gas Chromatography followed by Mass Spectroscopy analysis. Desmosterol has a characteristic m/z peak at 384, as seen in the mass spectra.<ref name=":12"/> |
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=== Ozonolysis === |
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Desmosterol has been identified through ozonolysis of the sample, with the ozonolysis product of desmosterol having a melting point of 128 °C, and an Rf value of 0.31 with paper-chromatography with n-hexane and N,N-dimethyl formamide. The ozonolysis product also has ratios C: 45.68; H: 4.45; N: 23.21.<ref name=":4" /> |
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==See also== |
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* ] |
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* ] |
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==References== |
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{{steroid-stub}} |
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{{Reflist|2}} |
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{{Cholesterol and steroid intermediates}} |
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{{Cholesterol and steroid intermediates}} |
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