Chemistry of marine natural products by Paul J. Scheuer

By Paul J. Scheuer

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By Paul J. Scheuer

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43 D. Carotenoids One of the simplest of the oxygenated carotenoids isolated from marine sources was also one of the earliest. Lederer (1935), one of the pioneers of carotenoid chemistry, reported the isolation of echinenone (102) from the Ο 102 gonads of the sea urchin Paracentrotus lividus (syn. Strongylocentrotus lividus)* and recognized it to be a monoketone. Goodwin and Taha (1950) first suspected and later (1951) showed the pigment, which they had isolated from other marine invertebrates, to be identical with another carotenoid, myxoxanthin.

Carotenoids As one proceeds from sesquiterpenoids via di- and triterpenoids to the tetraterpenoids, and as one looks at the structural variations among these polyisoprenoids of increasing size, one is struck by the fact that these compounds as a group become structurally more uniform as they become larger. As a result of this progression toward lesser diversity we arrive at this class of tetraterpenoids, the carotenoids, and find a coherent and well-defined group 40 1. Isoprenoids of compounds, most of which consist of a central branched nonaene chain of 22 carbon atoms with various nine-carbon moieties at each end of the central chain.

59 p p m in pyridine. The signal farthest downfield was assigned to the C-21 methyl group that is attached to C-20, which in turn is bonded to the lactonic oxygen atom. The y-lactone ring would then include the oxidized C-18 methyl. 90 ppm. 78 p p m (in CDCI3) that were incompletely resolved were compatible with the gemdimethyl group at C-25 that would be linked to the ether oxygen in line with their chemical shifts. The other carbon (C-22) that is linked to the ether oxygen atom bears a single hydrogen atom and has already been assigned.

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