By Paul J. Scheuer
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Extra info for Chemistry of marine natural products
The close similarity in the visible spectra of the two compounds, which is initially surprising, may be rationalized by two compensating parameters— the hypsochromic tendency of the triple bonds in alloxanthin is counteracted by the bathochromic effect caused by the ready planarity of the conjugated system that is engendered by the acetylenic linkages (Weedon, 1970). , 1967). It has also been isolated from the mussel Mytilus edulis. The two minor xanthophylls from the same algal source (Chapman, 1966) that yielded alloxanthin (109) were shown to be monadoxanthin of structure 111 and crocoxanthin, 112 (Mallams et al, 1967).
Bromobenzoate of an allenic degradation product of fucoxanthin (120) (De Ville et al, 1969). ^ιιιιιιΗ Η imiiOH c Br 120 Lederer (1935, 1938) in his early work on the pigments of marine invertebrates had noted the presence of u n c o m m o n carotenoids in sea urchins. Recent reinvestigation (Galasko et al, 1969) of the carotenoids of the sea urchin Paracentrotus lividus has led to the isolation of a trace of fucoxanthin 50 i . Isoprenoids (119) in addition to fucoxanthinol (121) and the C 3 1 carotenoid paracentrone (122).
The carotenoids are among the most widely distributed naturally occurring organic pigments, generally yellow or red in color, depending on the length and stereochemistry of the conjugated polyene chain. 1% of dry weight of extracted material, and normally as mixtures; they are sensitive to light, heat, and air; and they must be isolated from fresh material. In a recent progress report on carotenoid chemistry Liaaen-Jensen (1971) plotted the number of known naturally occurring carotenoids versus the year beginning at 1900; the resulting curve is virtually smooth and exponential.
Chemistry of marine natural products by Paul J. Scheuer