Carotenoids of the Carotenoprotein Asteriarubin. Optical Purity of Asterinic Acid

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Abstract
The carotenoid composition of the carotenoprotein asteriarubin ex the starfish Asterias rubens, determined by HPLC, comprised canthaxanthin (6, 3% of total), all‐trans‐astaxanthin (1, 14%), all‐trans‐7,8‐didehydroastaxanthin (2, 24%), all‐trans‐7,8,7′,8′‐tetradehydroastaxanthin (3, 43%) and 4‐oxomytiloxanthin (7, 10%). The previously unknown 4‐oxomytiloxanthin was tentatively identified by the UV./VIS., 'H‐NMR. spectra and MS. data.The optical purity was determined by HPLC. of the di‐(−)‐camphanates, by comparison with those of synthetic standards: 7,8,7′, 8′‐tetradehydroastaxanthin (92% (3S, 3′S), 2% meso), 7,8‐didehydroastaxanthin (89% (3S,3′S), 2% meso?), and astaxanthin (78% (3S,3′S), 14% (3R,3′S), and 5% (3R,3′R)). It is concluded that the acetylenic derivatives of astaxanthin in contrast to astaxanthin from marine animal sources are essentially pure (3S, 3′S)‐isomers. This might reflect their probable metabolic formation by 4‐oxo modification of acetylenic (3R,3′R)‐carotenols ex Mytilus edulis in their diet.

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