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Chemical Compound Review

ectoine     (4S)-2-methyl-3,4,5,6- tetrahydropyrimidine...

Synonyms: L-Ectoine, SureCN93532, SureCN977252, AG-K-69722, Thp(B), ...
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Disease relevance of ectoine

  • Isolation and characterization of salt-sensitive mutants of the moderate halophile Halomonas elongata and cloning of the ectoine synthesis genes [1].
  • To investigate the function of ectoine as a compatible solute in plant cells, the three genes were individually placed under the control of the cauliflower mosaic virus 35S promoter and introduced together into cultured tobacco (Nicotiana tabacum L.) cv Bright Yellow 2 (BY2) cells [2].
  • Osmoprotection of Escherichia coli by ectoine: uptake and accumulation characteristics [3].
  • To understand the mechanisms of ectoine-induced osmoprotection in Sinorhizobium meliloti, a proteomic examination of S. meliloti cells grown in minimal medium supplemented with ectoine was undertaken [4].
  • Functional expression of the ectoine hydroxylase gene (thpD) from Streptomyces chrysomallus in Halomonas elongata [5].

High impact information on ectoine

  • Finally, a cosmid from the H. elongata genomic library was isolated which complemented the Ect- phenotype of both mutants, indicating that it carried at least the genes ectB and ectC of the biosynthetic pathway of ectoine [1].
  • Despite the presence of nuclear inclusions, apoptotic features were less frequently observed after ectoine application [6].
  • (13)C-nuclear magnetic resonance analysis of cells grown in minimal medium at the limiting temperature of 45 degrees C revealed the presence of hydroxyectoine, ectoine, glutamate, trehalose (not present in cells grown at 37 degrees C), and the ectoine precursor, Ngamma-acetyldiaminobutyric acid [7].
  • Hence, it is conceivable that SMCs such as ectoine and hydroxyectoine could be potential inhibitors against the aggregate formation of Alzheimer's Abeta, which has not been studied to date [8].
  • The halophilic bacterium Halomonas elongata accumulates K+, glutamate, and the compatible solute ectoine as osmoprotectants [9].

Chemical compound and disease context of ectoine


Biological context of ectoine

  • On the basis of sequence homologies, eutABCDE encode enzymes with putative and hypothetical functions in ectoine catabolism [4].
  • This transporter was encoded by four genes (ehuA, ehuB, ehuC, and ehuD) that formed an operon with another gene cluster that contains five genes, named eutABCDE for ectoine utilization [4].
  • By repeatedly performing this "bacterial milking" process (at least nine times) we were able to produce large amounts of ectoines with a biomass productivity of 155 mg of ectoine per cycle per gram cell dry weight [14].
  • The ectoine transporter is encoded by an open reading frame of 1,578 bp named ectM [15].
  • A 480-bp Marinococcus halophilus DNA-fragment upstream of the ectoine genes ectABC was linked to the reporter gene gfp(uv) in the stress probe plasmid pBRGFP(uv) [16].

Anatomical context of ectoine

  • Therefore, the physiological role of TeaABC may be primarily to recover ectoine leaking through the cytoplasmic membrane [17].
  • Ectoine from halophilic microorganisms induces the expression of hsp70 and hsp70B' in human keratinocytes modulating the proinflammatory response [18].
  • Following a high-cell-density fermentation which provided biomass up to 48 g cell dry weight per liter, we applied alternating osmotic shocks in combination with crossflow filtration techniques to harvest the compatible solutes ectoine and hydroxyectoine [14].

Associations of ectoine with other chemical compounds


Gene context of ectoine

  • In addition, ectoine had no effect on proinflammatory cytokines interleukin (IL)-1alpha, IL-6, IL-8, and tumor necrosis factor-alpha and on NF-kappaB and IkappaB-alpha pathway, whereas it downregulated the expression of cited proinflammatory cytokines, in lipopolysaccharides-treated keratinocytes [18].
  • Strain CHR63 is a salt-sensitive mutant of the moderately halophilic wild-type strain Halomonas elongata DSM 3043 that is affected in the ectoine synthase gene (ectC) [22].
  • We constructed a deletion mutant of H. elongata, KB1, defective in ectoine synthesis and tolerating elevated salt concentrations only in the presence of external compatible solutes [17].
  • The purified cyanophycin synthetase maintained the parental thermophilic character and was active even after prolonged incubation at 50 degrees C; in the presence of ectoine the enzyme retained 90% of its activity even after 2 h of incubation [23].
  • In contrast, in the absence of heat shock, ectoine was unable to induce hsp70B' but had the ability to induce another member of the Hsp family, the hsp70 [18].

Analytical, diagnostic and therapeutic context of ectoine

  • HPLC analysis of osmotically challenged B. pasteurii cells revealed that ectoine production within this bacterium is finely tuned and closely correlated with the osmolality of the growth medium [24].
  • High-performance liquid chromatography analyses showed that the levels of ectoine and hydroxyectoine were maximal during the stationary phase of growth [7].
  • We therefore investigated the effects that cyclic naturally occurring ectoine-type compatible solutes and their synthetic derivatives have on melting temperature of double-stranded DNA (dsDNA) and on PCR amplification of different templates [25].
  • In this study, we evaluated the ability of ectoine, a novel natural biomolecule produced by halophilic microorganisms, to activate the hsp70 and hsp70B'. By reverse transcriptase-polymerase chain reaction and Western blot analysis, we demonstrated increased hsp70B' gene expression in human keratinocytes treated with ectoine and heat stressed [18].


  1. Isolation and characterization of salt-sensitive mutants of the moderate halophile Halomonas elongata and cloning of the ectoine synthesis genes. Cánovas, D., Vargas, C., Iglesias-Guerra, F., Csonka, L.N., Rhodes, D., Ventosa, A., Nieto, J.J. J. Biol. Chem. (1997) [Pubmed]
  2. Ectoine, the compatible solute of Halomonas elongata, confers hyperosmotic tolerance in cultured tobacco cells. Nakayama, H., Yoshida, K., Ono, H., Murooka, Y., Shinmyo, A. Plant Physiol. (2000) [Pubmed]
  3. Osmoprotection of Escherichia coli by ectoine: uptake and accumulation characteristics. Jebbar, M., Talibart, R., Gloux, K., Bernard, T., Blanco, C. J. Bacteriol. (1992) [Pubmed]
  4. Ectoine-induced proteins in Sinorhizobium meliloti include an Ectoine ABC-type transporter involved in osmoprotection and ectoine catabolism. Jebbar, M., Sohn-Bösser, L., Bremer, E., Bernard, T., Blanco, C. J. Bacteriol. (2005) [Pubmed]
  5. Functional expression of the ectoine hydroxylase gene (thpD) from Streptomyces chrysomallus in Halomonas elongata. Prabhu, J., Schauwecker, F., Grammel, N., Keller, U., Bernhard, M. Appl. Environ. Microbiol. (2004) [Pubmed]
  6. Ectoine alters subcellular localization of inclusions and reduces apoptotic cell death induced by the truncated Machado-Joseph disease gene product with an expanded polyglutamine stretch. Furusho, K., Yoshizawa, T., Shoji, S. Neurobiol. Dis. (2005) [Pubmed]
  7. The ectD gene, which is involved in the synthesis of the compatible solute hydroxyectoine, is essential for thermoprotection of the halophilic bacterium Chromohalobacter salexigens. García-Estepa, R., Argandoña, M., Reina-Bueno, M., Capote, N., Iglesias-Guerra, F., Nieto, J.J., Vargas, C. J. Bacteriol. (2006) [Pubmed]
  8. Ectoine and hydroxyectoine inhibit aggregation and neurotoxicity of Alzheimer's beta-amyloid. Kanapathipillai, M., Lentzen, G., Sierks, M., Park, C.B. FEBS Lett. (2005) [Pubmed]
  9. Potassium transport in a halophilic member of the bacteria domain: identification and characterization of the K+ uptake systems TrkH and TrkI from Halomonas elongata DSM 2581T. Kraegeloh, A., Amendt, B., Kunte, H.J. J. Bacteriol. (2005) [Pubmed]
  10. Disaccharides as a new class of nonaccumulated osmoprotectants for Sinorhizobium meliloti. Gouffi, K., Pica, N., Pichereau, V., Blanco, C. Appl. Environ. Microbiol. (1999) [Pubmed]
  11. Isolation and characterization of ButA, a secondary glycine betaine transport system operating in Tetragenococcus halophila. Baliarda, A., Robert, H., Jebbar, M., Blanco, C., Le Marrec, C. Curr. Microbiol. (2003) [Pubmed]
  12. Interrelation between synthesis and uptake of ectoine for the growth of the halotolerant Brevibacterium species JCM 6894 at high osmolarity. Nagata, S., Wang, Y.B. Microbios (2001) [Pubmed]
  13. Calorimetrically obtained information about the efficiency of ectoine synthesis from glucose in Halomonas elongata. Maskow, T., Babel, W. Biochim. Biophys. Acta (2001) [Pubmed]
  14. Bacterial milking: A novel bioprocess for production of compatible solutes. Sauer, T., Galinski, E.A. Biotechnol. Bioeng. (1998) [Pubmed]
  15. Marinococcus halophilus DSM 20408T encodes two transporters for compatible solutes belonging to the betaine-carnitine-choline transporter family: identification and characterization of ectoine transporter EctM and glycine betaine transporter BetM. Vermeulen, V., Kunte, H.J. Extremophiles (2004) [Pubmed]
  16. Investigation into a stress-inducible promoter region from Marinococcus halophilus using green fluorescent protein. Bestvater, T., Galinski, E.A. Extremophiles (2002) [Pubmed]
  17. New type of osmoregulated solute transporter identified in halophilic members of the bacteria domain: TRAP transporter TeaABC mediates uptake of ectoine and hydroxyectoine in Halomonas elongata DSM 2581(T). Grammann, K., Volke, A., Kunte, H.J. J. Bacteriol. (2002) [Pubmed]
  18. Ectoine from halophilic microorganisms induces the expression of hsp70 and hsp70B' in human keratinocytes modulating the proinflammatory response. Buommino, E., Schiraldi, C., Baroni, A., Paoletti, I., Lamberti, M., De Rosa, M., Tufano, M.A. Cell Stress Chaperones (2005) [Pubmed]
  19. Corynebacterium glutamicum is equipped with four secondary carriers for compatible solutes: identification, sequencing, and characterization of the proline/ectoine uptake system, ProP, and the ectoine/proline/glycine betaine carrier, EctP. Peter, H., Weil, B., Burkovski, A., Krämer, R., Morbach, S. J. Bacteriol. (1998) [Pubmed]
  20. Methylarcula marina gen. nov., sp. nov. and Methylarcula terricola sp. nov.: novel aerobic, moderately halophilic, facultatively methylotrophic bacteria from coastal saline environments. Doronina, N.V., Trotsenko, Y.A., Tourova, T.P. Int. J. Syst. Evol. Microbiol. (2000) [Pubmed]
  21. Construction and characterization of an NaCl-sensitive mutant of Halomonas elongata impaired in ectoine biosynthesis. Göller, K., Ofer, A., Galinski, E.A. FEMS Microbiol. Lett. (1998) [Pubmed]
  22. Role of Ngamma-acetyldiaminobutyrate as an enzyme stabilizer and an intermediate in the biosynthesis of hydroxyectoine. Cánovas, D., Borges, N., Vargas, C., Ventosa, A., Nieto, J.J., Santos, H. Appl. Environ. Microbiol. (1999) [Pubmed]
  23. Molecular characterization of a thermostable cyanophycin synthetase from the thermophilic cyanobacterium Synechococcus sp. strain MA19 and in vitro synthesis of cyanophycin and related polyamides. Hai, T., Oppermann-Sanio, F.B., Steinbüchel, A. Appl. Environ. Microbiol. (2002) [Pubmed]
  24. Osmotically regulated synthesis of the compatible solute ectoine in Bacillus pasteurii and related Bacillus spp. Kuhlmann, A.U., Bremer, E. Appl. Environ. Microbiol. (2002) [Pubmed]
  25. Characterization of the synthetic compatible solute homoectoine as a potent PCR enhancer. Schnoor, M., Voss, P., Cullen, P., Böking, T., Galla, H.J., Galinski, E.A., Lorkowski, S. Biochem. Biophys. Res. Commun. (2004) [Pubmed]
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