19,19'-Diacyloxy Signature: An Atypical Level of Structural Evolution in Carotenoid Pigments.

We report the isolation from the green dinoflagellate Lepidodinium chlorophorum and structural characterization of a new carotenoid termed lepidoxanthin (1), determined to be (3S,5R,6S,3'R,6'R)-5,6-epoxy-19-(2-decenoyloxy)-19'-acetoxy-4',5'-didehydro-5,6,5',6'-tetrahydro-β,ε-carotene-3,3'-diol. Its until now unidentified 19,19'-diacyloxy substitution constitutes a chemical signature that can aid in unraveling the evolutionary course of this unicellular algae based on the proposed biosynthethic pathway.