Configurational studies on red algae carotenoids |
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Authors: | Terje Bjørnland Gunner Borch Synnøve Liaaen-Jensen |
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Institution: | 1. Department of Marine Biology and Limnology, Section of Marine Botany, University of Oslo, P.O. Box 1069 Blindern, Oslo 3, Norway;2. Chemistry Department A, The Technical University of Denmark, DK-2800 Lyngby, Denmark;3. Organic Chemistry Laboratories, Norwegian Institute of Technology, University of Trondheim, N-7034 Trondheim, Norway |
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Abstract: | The configurations of (6′R)-β,ε-carotene, (3′R,6′R)-β,ε-caroten-3′-ol (α-cryptoxanthin), (3R,3′R,6′R)-β,ε-carotene-3,3′-diol (lutein), (3R)-β,β-caroten-3-ol (β-cryptoxanthin), (3R,3′R)-β,β-carotene-3,3′-diol (zeaxanthin) and all-trans (3S,5R,6S,3′R)-5,6-epoxy-5,6-dihydro-β,β-carotene-3,3′-diol (antheraxanthin) were established by CD and 1H NMR studies. The red algal carotenoids consequently possessed chiralities at each chiral center (C-3, C-5, C-6, C-3′, C-6′), corresponding to the chiralities established for the same carotenoids in higher plants. Two post mortem artifacts from Erythrotrichia carnea were assigned the chiral structures (3S,5R,8R,3′R)-5,8-epoxy-5,8-dihydro-β,β-carotene-3,3′-diol (8R)-mutatoxanthin] and (3S,5R,8S,3′R)-5,8-epoxy-5,8-dihydro-β,β-carotene-3,3′-diol (8S)-mutatoxanthin]. This is the first well documented report of a naturally occurring β,ε-caroten-3′-ol (1H NMR, CD, chemical derivatization). |
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Keywords: | Rhodophyceae common carotenoids chirality CD |
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