| Revision as of 18:16, 8 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Ch← Previous edit |
Latest revision as of 19:45, 17 January 2025 edit undoMarbletan (talk | contribs)Extended confirmed users5,638 edits Ectoine.svg |
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{{Use dmy dates|date=May 2021}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443718608 |
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| verifiedrevid = 443720196 |
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|Reference=<ref> at ]</ref> |
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| Name = |
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|ImageFile=Ectoine structural formulae v.1.png |
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| Reference =<ref> at ]</ref> |
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|ImageSize=120px |
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| ImageFile = Ectoine.svg |
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|IUPACName=(''S'')-2-methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid |
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| ImageSize = 120px |
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|OtherNames=THP(B) |
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| PIN = (4''S'')-2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid |
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|Section1= {{Chembox Identifiers |
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| OtherNames = {{plainlist|*Ectoine sodium salt monohydrate |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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* THP(B) |
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* RonaCare |
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* Pyrostatin B}} |
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| SystematicName = |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 112069 |
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| ChemSpiderID = 112069 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WQXNXVUDBPYKBA-YFKPBYRVSA-N |
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| StdInChIKey = WQXNXVUDBPYKBA-YFKPBYRVSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=96702-03-3 |
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| CASNo=96702-03-3 |
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| PubChem=126041 |
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| PubChem=126041 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 7GXZ3858RY |
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| UNII = 7GXZ3858RY |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES=CC1=NCCC(N1)C(=O)O |
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| SMILES=CC1=NCCC(N1)C(=O)O |
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|Section2= {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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| C=6 | H=10 | N=2 | O=2 |
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| Formula=C<sub>6</sub>H<sub>10</sub>N<sub>2</sub>O<sub>2</sub> |
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| Appearance=White powder |
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| MolarMass=142.16 |
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| Density=1.568 g/cm<sup>3</sup> |
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| Solubility=Soluble in water |
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|Section3= {{Chembox Hazards |
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| Section3 = {{Chembox Hazards |
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| NFPA-F = 1 |
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| NFPA-H = 1 |
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| NFPA-R = 0 |
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| NFPA_ref =<ref></ref> |
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'''Ectoine''' (1,4,5,6-Tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) is a natural compound found in several species of bacteria. It is a ] which serves as a protective substance by acting as an ] and thus helps organisms survive extreme ]. Ectoine is found in high concentrations in ] microorganisms and confers resistance towards salt and temperature stress. Ectoine was first identified in the microorganism '']'', but has since been found in a wide range of gram-negative and gram-positive bacteria. Some other species ectoine was found in: |
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'''Ectoine''' (3,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) is a natural compound found in several species of ]. It is a ] which serves as a protective substance by acting as an ] and thus helps organisms survive extreme ].<ref>{{Cite journal |last=Galinski |first=Erwin A. |last2=Trüper |first2=Hans G. |date=1985 |title=Die Kristallstruktur des Ectoin, einer neuen osmoregulatorisch wirksamen Aminosäure |url=https://www.degruyter.com/document/doi/10.1515/znc-1985-11-1206/html |journal=Zeitschrift für Naturforschung C |volume=40 |pages=780-784 |via=De Gruyter}}</ref> Furthermore it was shown to protect DNA against ionizing and ultraviolet radiation serving as a radical scavenger.<ref>{{Cite journal |last=Hahn |first=Marc Benjamin |last2=Meyer |first2=Susann |last3=Schröter |first3=Maria-Astrid |last4=Kunte |first4=Hans-Jörg |last5=Solomun |first5=Tihomir |last6=Sturm |first6=Heinz |date=2017-09-27 |title=DNA protection by ectoine from ionizing radiation: molecular mechanisms |url=https://pubs.rsc.org/en/content/articlelanding/2017/cp/c7cp02860a |journal=Physical Chemistry Chemical Physics |language=en |volume=19 |issue=37 |pages=25717–25722 |doi=10.1039/C7CP02860A |issn=1463-9084}}</ref> Ectoine is found in high concentrations in ] microorganisms and confers resistance towards salt and temperature stress. Ectoine was first identified in the microorganism ''] halochloris'',<ref name="r2" /><ref name="r1" /> but has since been found in a wide range of ] and ]. Other species of bacteria in which ectoine was found include: |
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* '']''<ref name="r1">{{cite journal |doi=10.1099/00221287-139-1-129 |url=http://www.microbiologyresearch.org/docserver/fulltext/micro/139/1/mic-139-1-129.pdf |title=Ectoine accumulation and osmotic regulation in ''Brevibacterium linens'' |journal=Journal of General Microbiology |volume=139 |pages=129–136 |year=1993 |last1=Bernard |first1=T. |last2=Jebbar |first2=M. |last3=Rassouli |first3=Y. |last4=Himdi-Kabbab |first4=S. |last5=Hamelin |first5=J. |last6=Blanco |first6=C. |doi-access=free}}</ref> |
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* '']'' |
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* '']''<ref name="r2">{{cite journal |doi=10.1016/0378-1097(90)90049-V |pmid=1601286 |title=The biosynthesis of ectoine |journal=FEMS Microbiology Letters |volume=71 |issue=2 |pages=157–61 |year=1990 |last1=Peters |first1=P |last2=Miwatani |first2=T |last3=Honda |first3=T|doi-access=free }}</ref><ref name="r4" /> |
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* '']'' |
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* '']''<ref name="r3">{{cite journal |pmid=9141677 |year=1997 |last1=Louis |first1=P |title=Characterization of genes for the biosynthesis of the compatible solute ectoine from ''Marinococcus halophilus'' and osmoregulated expression in ''Escherichia coli'' |journal=Microbiology |volume=143 ( Pt 4) |issue=4 |pages=1141–9 |last2=Galinski |first2=E. A. |doi=10.1099/00221287-143-4-1141 |doi-access=free}}</ref> |
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* '']'' |
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* '']''<ref name="r4">{{cite journal |pmid=21725014 |pmc=3165526 |year=2011 |last1=Stöveken |first1=N |title=A specialized aspartokinase enhances the biosynthesis of the osmoprotectants ectoine and hydroxyectoine in ''Pseudomonas stutzeri'' A1501 |journal=Journal of Bacteriology |volume=193 |issue=17 |pages=4456–68 |last2=Pittelkow |first2=M |last3=Sinner |first3=T |last4=Jensen |first4=R. A. |last5=Heider |first5=J |last6=Bremer |first6=E |doi=10.1128/JB.00345-11}}</ref> |
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* '']''<ref>{{cite web |last1=Augenstein |first1=Seth |title='Extremophile Bacteria' Will Eat Away Wreck of the Titanic |url=http://www.laboratoryequipment.com/news/2016/09/extremophile-bacteria-will-eat-away-wreck-titanic-2030 |website=laboratoryequipment.com |date=6 September 2016}}</ref><ref>{{cite journal |last1=Zaccai |first1=Giuseppe |last2=Bagyan |first2=Irina |last3=Combet |first3=Jérôme |last4=Cuello |first4=Gabriel J. |last5=Demé |first5=Bruno |last6=Fichou |first6=Yann |last7=Gallat |first7=François-Xavier |last8=Galvan Josa |first8=Victor M. |last9=von Gronau |first9=Susanne|last10=Haertlein|first10=Michael |last11=Martel |first11=Anne |last12=Moulin |first12=Martine |last13=Neumann |first13=Markus |last14=Weik |first14=Martin |last15=Oesterhelt |first15=Dieter |title=Neutrons describe ectoine effects on water H-bonding and hydration around a soluble protein and a cell membrane |journal=Scientific Reports |date=16 August 2016 |volume=6 |pages=31434 |doi=10.1038/srep31434 |pmid=27527336 |pmc=4985633 |bibcode=2016NatSR...631434Z}}</ref> |
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* '']''<ref>"HAMAP: Halorhodospira halophila (strain DSM 244 / SL1) (Ectothiorhodospira halophila (strain DSM 244 / SL1)) complete proteome {{dead link|date=August 2019 |bot=InternetArchiveBot |fix-attempted=yes }} http://hamap.expasy.org/proteomes/HALHL.html</ref> |
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* '']''<ref>{{cite journal |last1=Zhu |first1=Daochen |last2=Niu |first2=Lili |last3=Wang |first3=Chenxiang |last4=Nagata |first4=Shinichi |title=Isolation and characterisation of moderately halophilic bacteriumHalomonas ventosae DL7 synthesizing ectoine as compatible solute |journal=Annals of Microbiology |date=September 2007 |volume=57 |issue=3 |pages=401–406 |doi=10.1007/BF03175080 |s2cid=43421438 |url=http://www.lib.kobe-u.ac.jp/repository/90000871.pdf |access-date=5 December 2019 |archive-date=2 October 2020 |archive-url=https://web.archive.org/web/20201002004056/http://www.lib.kobe-u.ac.jp/repository/90000871.pdf |url-status=dead }}</ref> |
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==Biosynthesis== |
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== Biosynthesis == |
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Ectoine is synthesized in three successive enzymatic reactions starting from aspartic β-semialdehyde. The genes involved in the biosynthesis are called ''ectA'', ''ectB'' and ''ectC'' and they encode the enzymes L-2,4-diaminobutyric acid acetyltransferase, L-2,4-diaminobutyric acid transaminase, and L-ectoine synthase respectively. |
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Ectoine is synthesized in three successive ] starting from ]. The genes involved in the biosynthesis are called ''ectA'', ''ectB'' and ''ectC'', and they encode the enzymes ], ] and ], respectively.<ref name="r3" /><ref name="r4" /> |
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==Use== |
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== Use in cosmetics == |
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Ectoine is used as an active ingredient in skin care and ] products. It stabilizes ]s and other cellular structures and protects the skin from stresses like UV irradiation and dryness. |
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Ectoine is used as an active ingredient in ] and ] products.<ref name="Gerday Glansdorff 2009 p. 303">{{cite book |last1=Gerday |first1=C. |last2=Glansdorff |first2=N. |title=EXTREMOPHILES – Volume II |publisher=Eolss Publishers |series=Encyclopedia of life support systems |year=2009 |isbn=978-1-905839-94-0 |url=https://books.google.com/books?id=i5zEDAAAQBAJ&pg=PA303 |access-date=18 May 2021 |page=303 ff}}</ref> It stabilizes ]s and other cellular structures and protects the skin from stresses like ] and dryness.<ref name="r4" /> |
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==References== |
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== Medical use == |
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Due to its protein stabilizing properties, ectoine has been evaluated as a topical treatment for ]. Effectiveness of a nasal spray containing ectoine is comparable to ] and is reported to be well tolerated by the patients.<ref>{{Cite journal |last1=Werkhäuser |first1=Nina |last2=Bilstein |first2=Andreas |last3=Sonnemann |first3=Uwe |date=2014-06-01 |title=Treatment of Allergic Rhinitis with Ectoine Containing Nasal Spray and Eye Drops in Comparison with Azelastine Containing Nasal Spray and Eye Drops or with Cromoglycic Acid Containing Nasal Spray |journal=Journal of Allergy |volume=2014 |pages=1–13 |doi=10.1155/2014/176597 |pmid=24982680 |issn=1687-9783|pmc=4058592 |doi-access=free }}</ref> It is available ] in European Union. |
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== References == |
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{{reflist}} |
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{{biochem-stub}} |
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