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Metabolism of carotenoids in salmonids . Part 2 . Distribution and absolute configuration of idoxanthin in various organs and tissues of one atlantic salmon ( Salmo salar , L.) fed with astaxanthin
Author(s) -
Schiedt Katharina,
Mayer Hans,
Vecchi Max,
Glinz Ernst,
Storebakken Trond
Publication year - 1988
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19880710425
Subject(s) - astaxanthin , salmo , chemistry , carotenoid , high performance liquid chromatography , derivative (finance) , stereochemistry , absolute configuration , chromatography , fish <actinopterygii> , biochemistry , fishery , biology , financial economics , economics
The content of total carotenoids and the ratio astaxanthin/idoxanthin ( = 3,3′‐dihydroxy‐β,β‐carotene‐4,4′‐dione/3,3′,4′‐trihydroxy‐β,β‐caroten‐4‐one) in varoius organs and tissues of one Atlantic salmon ( Salmo salar , L.) reared indoors in a tank were analyzed after feeding ‘racemic’ ((3 R ,3′ R )/(3 R ,3′ S; meso )/(3 S ,3′ S ) 1:2:) astaxanthin (90 mg/kg feed) during one yera. Configurational analysis of astaxanthin was carried out via the (−)‐dicamphanate derivative and that of idoxanthin after reaction with (+)‐( S )‐l‐(l‐naphthyl)ethyl isocyanate. Separation of all eight optical isomers of idoxanthin‐tricarbamate derivatives by HPLC is described. In salmon, enzymatic reduction of astaxanthin was found to be sterospecific leading to th (4′ R )‐hydroxy group irrespective of the configuration at C(3′), thus resulting in four different stereoisomers of idoxanthin formed from (3 R ,3′ R ), (3 R ,3′ S ; meso )‐, and (3 S 3′ S )‐astaxanthin present in the diet.