Comparative biochemical studies of carotenoids in fishes—XXIX. Isolation of new luteins, lutein F and lutein G from marine fishes

Separation and identification of carotenoids and carotenol fatty acid esters in some squash products by liquid chromatography. 2. Isolation and characterization of carotenoids and related esters

“…This naturally occurring lutein (3R,3'R,6'R) is widely distributed not only in plants (Goodwin, 1980), but also in animals (Liaaen-Jensen, 1978). Among the eight possible stereoisomers of lutein (/3,ecarotene-3,3'-diol) with three centers of chirality, five of them have been synthesized by Mayer (1982) and two of them have recently been isolated from the integuments of marine fishes by Matsuno et al (1986).…”

Isolation of Stereoisomeric Epoxy Carotenoids and New Acetylenic Carotenoid from the Common Freshwater Goby Rhinogobius brunneus

“…The crude carotenoids were separated by column chromatography on Si gel. Each fraction was saponified with 10% The following carotenoids were identified from R. brunneus: β,β-carotene; β-echinenone; (2R)-and (2S)-β,β-caroten-2-ol; 15 (3′R,6′S)-and (3′S,6′S)-β, -caroten-3′-ol, 16 β-cryptoxanthin; canthaxanthin; tunaxanthins A, B, C, G, and H, 17 luteins A, D, and F, 18 (3R,3′R)-, (3R,3′S; meso)-, and (3S,3′S)-zeaxanthin; 19 diatoxanthin; alloxanthin; (3R,3′R)-, (3R,3′S; meso)-, and (3S,3′S)-astaxanthin; 20 4-ketoluteins A, D, and F; 21 and (3S,3′R)-4-ketozeaxanthin; 22 based on the vis, MS, and CD spectral data. Thirty-three known carotenoids and two new carotenoids were isolated from R. brunneus as shown in Table 2.…”

“…Naturally occurring epoxy carotenoids such as violaxanthin, antheraxanthin, and diadinoxanthin possess the 3 S ,5 R ,6 S configuration (3,5- trans -type), and other optical stereoisomers have not been reported . On the other hand, tunaxanthin, lutein, zeaxanthin, and astaxanthin , from fish have been found to be mixtures of optical stereoisomers. In the course of our stereochemical studies of carotenoids in fish, epoxy carotenoids having the 3 S ,5 S ,6 R configuration (3,5- cis type), namely diadinoxanthin B [(3 S ,5 S ,6 R ,3‘ R )-diadinoxanthin] ( 1 ) and antheraxanthin B [(3 S ,5 S ,6 R ,3‘ R )-antheraxanthin] ( 2 ), along with diadinoxanthin A [(3 S ,5 R ,6 S ,3‘ R )-diadinoxanthin] and antheraxanthin A [(3 S ,5 R ,6 S ,3‘ R )-antheraxanthin], were recently isolated from the common freshwater goby Rhinogobius brunneus Temminck et Schlegel) (Gobbiidae), as shown in Figure .…”

Synthesis of (3S,3′S)- and meso-Stereoisomers of Alloxanthin and Determination of Absolute Configuration of Alloxanthin Isolated from Aquatic Animals

“…Namely, astaxanthin in crustaceans and marine fishes exists as a mixture of three stereoisomers at C3 and C3′-positions [15,16]. Zeaxanthin [17], lutein [18], and tunaxanthin [19] in marine fishes also consist of these stereoisomers. Their absolute configurations were determined by CD spectra and chiral HPLC analyses.…”