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Algal carotenoids. Part 64. Structure and chemistry of 4-keto-19'-hexanoyloxyfucoxanthin with a novel carotenoid end group

AuthorsSkarstad Egeland, Einar; Garrido, J. L. ; Zapata, Manuel ; Maestro, Miguel Ángel; Liaaen-Jensen, Synnøve
Issue Date2000
PublisherRoyal Society of Chemistry (UK)
CitationJournal of Chemical Society Perkin Transactions 1: 1223-1230 (2000)
AbstractThe structural elucidation of a new carotenoid 4-keto-19-hexanoyloxyfucoxanthin 5 from Emiliania huxleyi is documented by chromatographic (HPLC, TLC), spectroscopic (VIS, EIMS, FABMS, FABMSMS, 2D 1H NMR) and chemical evidence. The novel carotenoid end group exhibits particular spectroscopic and chemical properties. In particular the reactions with base and acid are investigated.Due to a very weak molecular ion upon electron impact and facile cleavage to paracentrone 20 related fragments, the new carotenoid was previously misidentified as 19-hexanoyloxyparacentrone 3-acetate 8, also found in other prymnesiophytes (haptophytes).This novel carotenoid readily undergoes cleavage to a C31-skeletal paracentrone 20 related product upon storage, preferably in methanol solution.The new end group represents a plausible precursor for C31-skeletal methyl ketone apocarotenoid metabolites in animals, and differs from the previously suggested precursor.
Description8 pages, 2 figures, 5 schemes.
Publisher version (URL)http://dx.doi.org/10.1039/a910345g
Appears in Collections:(IIM) Artículos
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