Ectoine

Last updated

Contents

Ectoine [1]
Ectoine.svg
Names
Preferred IUPAC name
(4S)-2-Methyl-3,4,5,6-tetrahydropyrimidine-4-carboxylic acid
Other names
  • Ectoine sodium salt monohydrate
  • THP(B)
  • RonaCare
  • Pyrostatin B
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1 Yes check.svgY
    Key: WQXNXVUDBPYKBA-YFKPBYRVSA-N Yes check.svgY
  • InChI=1/C6H10N2O2/c1-4-7-3-2-5(8-4)6(9)10/h5H,2-3H2,1H3,(H,7,8)(H,9,10)/t5-/m0/s1
    Key: WQXNXVUDBPYKBA-YFKPBYRVBN
  • CC1=NCCC(N1)C(=O)O
  • O=C(O)[C@H]1N\C(=N/CC1)C
Properties
C6H10N2O2
Molar mass 142.158 g·mol−1
AppearanceWhite powder
Density 1.568 g/cm3
Soluble in water
Hazards
NFPA 704 (fire diamond)
[2]
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Ectoine (3,4,5,6-tetrahydro-2-methyl-4-pyrimidinecarboxylic acid) is a natural compound found in several species of bacteria. It is a compatible solute which serves as a protective substance by acting as an osmolyte and thus helps organisms survive extreme osmotic stress. [3] Furthermore it was shown to protect DNA against ionizing and ultraviolet radiation serving as a radical scavenger. [4] Ectoine is found in high concentrations in halophilic microorganisms and confers resistance towards salt and temperature stress. Ectoine was first identified in the microorganism Ectothiorhodospira halochloris, [5] [6] but has since been found in a wide range of Gram-negative and Gram-positive bacteria. Other species of bacteria in which ectoine was found include:

Biosynthesis

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. [8] [7]

Use in cosmetics

Ectoine is used as an active ingredient in skin care and sun protection products. [13] It stabilizes proteins and other cellular structures and protects the skin from stresses like UV irradiation and dryness. [7]

Medical use

Due to its protein stabilizing properties, ectoine has been evaluated as a topical treatment for hay fever. Effectiveness of a nasal spray containing ectoine is comparable to cromoglycate and is reported to be well tolerated by the patients. [14] It is available over-the-counter in European Union.

Related Research Articles

A halophile is an extremophile that thrives in high salt concentrations. In chemical terms, halophile refers to a Lewis acidic species that has some ability to extract halides from other chemical species.

Halotolerance is the adaptation of living organisms to conditions of high salinity. Halotolerant species tend to live in areas such as hypersaline lakes, coastal dunes, saline deserts, salt marshes, and inland salt seas and springs. Halophiles are organisms that live in highly saline environments, and require the salinity to survive, while halotolerant organisms can grow under saline conditions, but do not require elevated concentrations of salt for growth. Halophytes are salt-tolerant higher plants. Halotolerant microorganisms are of considerable biotechnological interest.

<span class="mw-page-title-main">Halomonadaceae</span> Family of bacteria

Halomonadaceae is a family of halophilic Pseudomonadota.

<i>Halomonas</i> Genus of bacteria

Halomonas is a genus of halophilic (salt-tolerating) bacteria. It grows over the range of 5 to 25% NaCl.

The enzyme ectoine synthase (EC ) catalyzes the chemical reaction

In enzymology, a diaminobutyrate acetyltransferase (EC 2.3.1.178) is an enzyme that catalyzes the chemical reaction

In enzymology, a diaminobutyrate-2-oxoglutarate transaminase is an enzyme that catalyzes the chemical reaction

Osmoprotectants or compatible solutes are small organic molecules with neutral charge and low toxicity at high concentrations that act as osmolytes and help organisms to survive in extreme osmotic stress. Osmoprotectants can be placed in three chemical classes: betaines and associated molecules, sugars and polyols, and amino acids. These molecules accumulate in cells and balance the osmotic difference between the cell's surroundings and the cytosol. In plants, their accumulation can increase survival during stresses such as drought. In extreme cases, such as in bdelloid rotifers, tardigrades, brine shrimp, and nematodes, these molecules can allow cells to survive being completely dried out and let them enter a state of suspended animation called cryptobiosis.

<span class="mw-page-title-main">Pyoverdine</span> Chemical compound

Pyoverdines are fluorescent siderophores produced by certain pseudomonads. Pyoverdines are important virulence factors, and are required for pathogenesis in many biological models of infection. Their contributions to bacterial pathogenesis include providing a crucial nutrient, regulation of other virulence factors, supporting the formation of biofilms, and are increasingly recognized for having toxicity themselves.

Tetragenococcus halophilus is a halophilic lactic acid bacterium active in the fermentation processes of soy sauce, miso, fish sauce and salted anchovies.

<i>Halomonas titanicae</i> Species of bacterium

Halomonas titanicae is a gram-negative, halophilic species of bacteria which was isolated in 2010 from rusticles recovered from the wreck of the RMS Titanic. It has been estimated by Henrietta Mann, one of the researchers that first isolated it, that the action of microbes like H. titanicae may bring about the total deterioration of the Titanic by 2030. While the bacteria have been identified as a potential danger to oil rigs and other man-made objects in the deep sea, they also have the potential to be used in bioremediation to accelerate the decomposition of shipwrecks littering the ocean floor.

Deleya halophila is a salt-loving, gram-negative bacteria. It is known to habitat marine environments, solar salterns, saline soils, and salted food. The genus was named after J. De Ley, a noted biologist. Its type strain is CCM 3662.

Halobacillus trueperi is a species of bacteria. It is halophilic, gram-positive, heterotrophic and its type strain is DSM 10404T.

Halomonas ventosae is a moderately halophilic, denitrifying, exopolysaccharide-producing bacterium. Its type strain is Al12T.

Halomonas anticariensis is a bacterium. It is strictly aerobic and because of its production of exopolysaccharides forms cream-coloured, mucoid colonies. FP35T is the type strain. Its genome has been sequenced.

Halorhodospira halophila is a species of Halorhodospira distinguished by its ability to grow optimally in an environment of 15–20% salinity. It was formerly called Ectothiorhodospira halophila. It is an anaerobic, rod-shaped Gram-negative bacterium. H. halophila has a flagellum.

The Thioalkalibacteraceae are a family of extremophiles, namely halophilic, alkaliphilic or alkalitolerant, mesophilic to thermophilic obligately chemolithoautotrophic organisms in the Chromatiales comprising the genus Thioalkalibacter and Guyparkeria. The family is closely related to the family Halothiobacillaceae of halotolerant, mesophilic obligate autotrophs.

Guyparkeria is a genus in the Gammaproteobacteria. Both species are obligate aerobic bacteria; they require oxygen to grow. They are also halophilic and have varying degrees of thermophilicity. They live in environments with high concentrations of salt or other solutes, such as in hydrothermal vent plumes or in hypersaline playas, and do require high sodium ion concentrations in order to grow, as is also the case in the other genus of the same family, Thioalkalibacter

Marinococcus halophilus is a Gram-positive and halophilic bacterium from the genus of Marinococcus which has been isolated from a salted mackerel. Marinococcus halophilus produces ectoine.

Halomonas elongata is considered the type species of the genus Halomonas. It is a chemoorganotrophic, halophilic bacterium first isolated from a solar salt facility located in Bonaire, Netherlands Antilles.

References

  1. ↑ Ectoine at Sigma-Aldrich
  2. ↑ Ectoine SDS
  3. ↑ Galinski, Erwin A.; Trüper, Hans G. (1985). "Die Kristallstruktur des Ectoin, einer neuen osmoregulatorisch wirksamen Aminosäure". Zeitschrift für Naturforschung C. 40: 780–784 – via De Gruyter.
  4. ↑ Hahn, Marc Benjamin; Meyer, Susann; Schröter, Maria-Astrid; Kunte, Hans-Jörg; Solomun, Tihomir; Sturm, Heinz (27 September 2017). "DNA protection by ectoine from ionizing radiation: molecular mechanisms". Physical Chemistry Chemical Physics. 19 (37): 25717–25722. doi:10.1039/C7CP02860A. ISSN   1463-9084.
  5. 1 2 Peters, P; Miwatani, T; Honda, T (1990). "The biosynthesis of ectoine". FEMS Microbiology Letters. 71 (2): 157–61. doi: 10.1016/0378-1097(90)90049-V . PMID   1601286.
  6. 1 2 Bernard, T.; Jebbar, M.; Rassouli, Y.; Himdi-Kabbab, S.; Hamelin, J.; Blanco, C. (1993). "Ectoine accumulation and osmotic regulation in Brevibacterium linens" (PDF). Journal of General Microbiology. 139: 129–136. doi: 10.1099/00221287-139-1-129 .
  7. 1 2 3 4 Stöveken, N; Pittelkow, M; Sinner, T; Jensen, R. A.; Heider, J; Bremer, E (2011). "A specialized aspartokinase enhances the biosynthesis of the osmoprotectants ectoine and hydroxyectoine in Pseudomonas stutzeri A1501". Journal of Bacteriology. 193 (17): 4456–68. doi:10.1128/JB.00345-11. PMC   3165526 . PMID   21725014.
  8. 1 2 Louis, P; Galinski, E. A. (1997). "Characterization of genes for the biosynthesis of the compatible solute ectoine from Marinococcus halophilus and osmoregulated expression in Escherichia coli". Microbiology. 143 ( Pt 4) (4): 1141–9. doi: 10.1099/00221287-143-4-1141 . PMID   9141677.
  9. ↑ Augenstein, Seth (6 September 2016). "'Extremophile Bacteria' Will Eat Away Wreck of the Titanic". laboratoryequipment.com.
  10. ↑ Zaccai, Giuseppe; Bagyan, Irina; Combet, Jérôme; Cuello, Gabriel J.; Demé, Bruno; Fichou, Yann; Gallat, François-Xavier; Galvan Josa, Victor M.; von Gronau, Susanne; Haertlein, Michael; Martel, Anne; Moulin, Martine; Neumann, Markus; Weik, Martin; Oesterhelt, Dieter (16 August 2016). "Neutrons describe ectoine effects on water H-bonding and hydration around a soluble protein and a cell membrane". Scientific Reports. 6: 31434. Bibcode:2016NatSR...631434Z. doi:10.1038/srep31434. PMC   4985633 . PMID   27527336.
  11. ↑ "HAMAP: Halorhodospira halophila (strain DSM 244 / SL1) (Ectothiorhodospira halophila (strain DSM 244 / SL1)) complete proteome ExPASy Proteomics Server. Swiss Institute of Bioinformatics [ permanent dead link ] http://hamap.expasy.org/proteomes/HALHL.html
  12. ↑ Zhu, Daochen; Niu, Lili; Wang, Chenxiang; Nagata, Shinichi (September 2007). "Isolation and characterisation of moderately halophilic bacteriumHalomonas ventosae DL7 synthesizing ectoine as compatible solute" (PDF). Annals of Microbiology. 57 (3): 401–406. doi:10.1007/BF03175080. S2CID   43421438. Archived from the original (PDF) on 2 October 2020. Retrieved 5 December 2019.
  13. ↑ Gerday, C.; Glansdorff, N. (2009). EXTREMOPHILES – Volume II. Encyclopedia of life support systems. Eolss Publishers. p. 303 ff. ISBN   978-1-905839-94-0 . Retrieved 18 May 2021.
  14. ↑ Werkhäuser, Nina; Bilstein, Andreas; Sonnemann, Uwe (1 June 2014). "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 of Allergy. 2014: 1–13. doi: 10.1155/2014/176597 . ISSN   1687-9783. PMC   4058592 . PMID   24982680.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.