From Wikipedia, the free encyclopedia
Selenoneine
Identifiers
ChEBI
ChemSpider
InChI=1S/C9H15N3O2Se/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H2-,10,11,13,14,15)/t7-/m0/s1
Key: MTIQLELFQVCRSW-ZETCQYMHSA-N
selenol tautomer: InChI=1S/C9H14N3O2Se/c1-12(2,3)7(8(13)14)4-6-5-10-9(15)11-6/h5,7H,4H2,1-3H3,(H-,10,11,13,14)/t7-/m0/s1
Key: FONQTPPQNMLDTP-ZETCQYMHSA-N
C[N+](C)(C)[C@@H](Cc1c[nH][c](=[Se])[nH]1)C([O-])=O
selenol tautomer: C[N+](C)(C)[C@@H](CC1=CN=C(N1)[Se])C(=O)[O-]
Properties
C 9 H 14 N 3 O 2 Se
Molar mass
275.201 g·mol−1
Related compounds
Related compounds
Selenocysteine ;
Ergothioneine ;
Histidine
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Selenoneine is a
selenium containing
ergothioneine derivative where the selenium (Se) atom replaces a sulfur atom. It can be systematically named as (2-selenyl-Nα ,Nα ,Nα -trimethyl-L-histidine or 3-(2-hydroseleno-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate).
It is found in the blood of
bluefin tuna ,
[1]
[2] and other sea dwelling animals like turtles, mackerel,
beluga ,
[3] and
giant petrels .
[4] It is an antioxidant,
[5] combining with
reactive oxygen species and boosting the action of
GPx1 .
[6]
Selenoneine is produced by microorganisms using enzymes that form a selenium-carbon bond.
[7] Humans that eat fish have selenoneine in their blood. About half of selenium is in the form of selenoneine.
[8]
[9] Selenoneine inhibits
angiotensin-converting enzyme .
[10] In vertebrates, selenoneine is transported into cells using
OCTN1 .
[4] Selenoneine reacts with
methyl mercury to form a mercury tetraselenoate complex, which degrades to
tiemannite , a
mercury selenide . This is a mechanism used to detoxify mercury in marine vertebrates.
[4] A related derivative, Se-methylselenoneine is found in lesser quantities in mackerel, sardine and tuna.
[11]
In air selenoneine is easily oxidised to a dimer containing a
diselenide bond (Se-Se).
[5]
References
^ Yamashita, Michiaki; Yamashita, Yumiko; Suzuki, Tamami; Kani, Yoko; Mizusawa, Nanami; Imamura, Shintaro; Takemoto, Kenji; Hara, Tatsuro; Hossain, Md. Anwar; Yabu, Takeshi; Touhata, Ken (October 2013).
"Selenoneine, a Novel Selenium-Containing Compound, Mediates Detoxification Mechanisms against Methylmercury Accumulation and Toxicity in Zebrafish Embryo" . Marine Biotechnology . 15 (5): 559–570.
Bibcode :
2013MarBt..15..559Y .
doi :
10.1007/s10126-013-9508-1 .
PMC
3742965 .
PMID
23709046 .
S2CID
7805355 .
^ Yamashita, Yumiko; Yamashita, Michiaki (June 2010).
"Identification of a Novel Selenium-containing Compound, Selenoneine, as the Predominant Chemical Form of Organic Selenium in the Blood of Bluefin Tuna" . Journal of Biological Chemistry . 285 (24): 18134–18138.
doi :
10.1074/jbc.C110.106377 .
PMC
2881734 .
PMID
20388714 .
^ Achouba, Adel; Dumas, Pierre; Ouellet, Nathalie; Little, Matthew; Lemire, Mélanie; Ayotte, Pierre (2019-08-01).
"Selenoneine is a major selenium species in beluga skin and red blood cells of Inuit from Nunavik" . Chemosphere . 229 : 549–558.
Bibcode :
2019Chmsp.229..549A .
doi :
10.1016/j.chemosphere.2019.04.191 .
hdl :
20.500.11794/38377 .
ISSN
0045-6535 .
PMID
31100626 .
^
a
b
c El Hanafi, Khouloud; Pedrero, Zoyne; Ouerdane, Laurent; Marchán Moreno, Claudia; Queipo-Abad, Silvia; Bueno, Maite; Pannier, Florence; Corns, Warren T.; Cherel, Yves; Bustamante, Paco; Amouroux, David (1 March 2022).
"First Time Identification of Selenoneine in Seabirds and Its Potential Role in Mercury Detoxification" (PDF) . Environmental Science & Technology . 56 (5): 3288–3298.
Bibcode :
2022EnST...56.3288E .
doi :
10.1021/acs.est.1c04966 .
PMID
35170956 .
S2CID
246865626 .
^
a
b Gammelgaard, Bente; Jackson, Matthew I.; Gabel-Jensen, Charlotte (February 2011).
"Surveying selenium speciation from soil to cell—forms and transformations" . Analytical and Bioanalytical Chemistry . 399 (5): 1743–1763.
doi :
10.1007/s00216-010-4212-8 .
PMID
20953781 .
S2CID
31792266 .
^ Kim, Se-Kwon (21 January 2015).
Springer Handbook of Marine Biotechnology . Springer. p. 1063.
ISBN
978-3-642-53971-8 .
^ Kayrouz, Chase M.; Huang, Jonathan; Hauser, Nicole; Seyedsayamdost, Mohammad R. (7 September 2022). "Biosynthesis of selenium-containing small molecules in diverse microorganisms". Nature . 610 (7930): 199–204.
Bibcode :
2022Natur.610..199K .
doi :
10.1038/s41586-022-05174-2 .
PMID
36071162 .
S2CID
252120205 .
^ Yamashita, Michiaki; Yamashita, Yumiko; Ando, Tetsuo; Wakamiya, Junji; Akiba, Suminori (December 2013).
"Identification and Determination of Selenoneine, 2-Selenyl-N α , N α , N α -Trimethyl-l-Histidine, as the Major Organic Selenium in Blood Cells in a Fish-Eating Population on Remote Japanese Islands" . Biological Trace Element Research . 156 (1–3): 36–44.
doi :
10.1007/s12011-013-9846-x .
PMC
3844148 .
PMID
24197605 .
^ Little, Matthew; Achouba, Adel; Dumas, Pierre; Ouellet, Nathalie; Ayotte, Pierre; Lemire, Mélanie (2019-06-01).
"Determinants of selenoneine concentration in red blood cells of Inuit from Nunavik (Northern Québec, Canada)" . Environment International . 127 : 243–252.
Bibcode :
2019EnInt.127..243L .
doi :
10.1016/j.envint.2018.11.077 .
hdl :
20.500.11794/38343 .
ISSN
0160-4120 .
PMID
30928848 .
^ Gröber, Uwe; Holick, Michael F. (2021).
"The coronavirus disease (COVID-19) – A supportive approach with selected micronutrients" . Int J Vitam Nutr Res . 92 (1): 13–34.
doi :
10.1024/0300-9831/a000693 .
PMID
33487035 .
S2CID
231702745 .
^ Kroepfl, Nina; Jensen, Kenneth B.; Francesconi, Kevin A.; Kuehnelt, Doris (October 2015). "Human excretory products of selenium are natural constituents of marine fish muscle". Analytical and Bioanalytical Chemistry . 407 (25): 7713–7719.
doi :
10.1007/s00216-015-8936-3 .
PMID
26253229 .
S2CID
42340594 .