Identification of a Novel Selenium-containing Compound, Selenoneine, as the Predominant Chemical Form of Organic Selenium in the Blood of Bluefin Tuna

A novel selenium-containing compound having a selenium atom in the imidazole ring, 2-selenyl-Nα,Nα,Nα-trimethyl-l-histidine, 3-(2-hydroseleno-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate, was identified from the blood and other tissues of the bluefin tuna, Thunnus orientalis. The selenium-contai...

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Bibliographic Details
Published in:The Journal of biological chemistry 2010-06, Vol.285 (24), p.18134-18138
Main Authors: Yamashita, Yumiko, Yamashita, Michiaki
Format: Article
Language:English
Subjects:
Amino Acid
Animals
Antioxidant
Antioxidants - chemistry
Betaine
Dimerization
Ergothioneine
Fish Products
Free Radical Scavengers - chemistry
Glutathione
Histidine - analogs & derivatives
Histidine - blood
Humans
Marine
Mass Spectrometry - methods
Metabolism
Models, Chemical
Organic Chemicals
Organoselenium Compounds - blood
Oxidative Stress
Oxygen - chemistry
Radicals
Reactive Oxygen Species (ROS)
Scomber
Selenium
Selenium - blood
Selenium Compounds - blood
Spectrophotometry, Ultraviolet - methods
Thunnus orientalis
Tilapia
Tuna - blood
Water - chemistry
Zebrafish
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Summary:A novel selenium-containing compound having a selenium atom in the imidazole ring, 2-selenyl-Nα,Nα,Nα-trimethyl-l-histidine, 3-(2-hydroseleno-1H-imidazol-5-yl)-2-(trimethylammonio)propanoate, was identified from the blood and other tissues of the bluefin tuna, Thunnus orientalis. The selenium-containing compound was purified from the tuna blood in several chromatographic steps. High resolution mass spectrometry and nuclear magnetic resonance spectroscopy showed that the exact mass of the [M+H]+ ion of the compound was 533.0562 and the molecular formula was C18H29N6O4Se2. Its gross structure was assigned as the oxidized dimeric form of an ergothioneine selenium analog in which the sulfur of ergothioneine is replaced by selenium. Therefore, we named this novel selenium-containing compound “selenoneine.” By speciation analysis of organic selenium compounds using liquid chromatography inductively coupled plasma mass spectrometry, selenoneine was found widely distributed in various tissues of the tuna, with the highest concentration in blood; mackerel blood contained similar levels. Selenoneine was measurable at 2–4 orders of magnitude lower concentration in a limited set of tissues from squid, tilapia, pig, and chicken. Quantitatively, selenoneine is the predominant form of organic selenium in tuna tissues.
ISSN:0021-9258
1083-351X
DOI:10.1074/jbc.C110.106377