Isolation of stereoisomeric epoxy carotenoids and new acetylenic carotenoid from the common freshwater goby Rhinogobius brunneus.
Stereoisomeric epoxy carotenoids with 3,5-cis configuration, diadinoxanthin B [(3S,5S,6R,3'R)-diadinoxanthin] (1) and antheraxanthin B [(3S,5S,6R,3'R)-antheraxanthin] (2), along with diadinoxanthin A [(3S,5R,6S,3'R)-diadinoxanthin] and antheraxanthin A [(3S,5R,6S,3'R)-antheraxanthin], were isolated from the common freshwater goby Rhinogobius brunneus. This is the first example in nature of 3,5-cis carotenoid epoxides. Furthermore, a new acetylenic triol carotenoid, gobiusxanthin (3), was obtained, and its structure was determined to be 7,8-didehydro-beta, epsilon-carotene-3,3', 6'-triol by chemical and spectral data.
Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan. tsushima@mb.kyoto-phu.ac.jp
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D000114:Acetylene / Q000737:chemistry; D000818:Animals; D002338:Carotenoids / Q000737:chemistry / Q000302:isolation & purification*; D004852:Epoxy Compounds / Q000737:chemistry; D005399:Fishes; D015394:Molecular Structure; D013057:Spectrum Analysis
D004852:Epoxy Compounds; D002338:Carotenoids; D000114:Acetylene