Chemistry

Chemistry of marine natural products by Paul J. Scheuer

By Paul J. Scheuer

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The resulting aglycones were a mixture of mono- and dimethoxy fleo-holothurinogenins, which by the conventional strong acid treatment could be converted to the known holothurinogenins. Holothurin A, the mixture of natural glycosides, contains only one methoxy group as 3-methoxy-D-glucose. The methoxy group(s) of the weo-holothurinogenins must therefore have arisen as a result of methanolysis. By careful spectral analysis the structures of the neo compounds were shown to be 79a, 79b, 80, 81, and the dimethoxy compound 82.

Chemical degradation and extensive spectral analysis led to the assignment of structure 123 for peridinin, which is the natural acetate of a C 3 7 carotenoid. Peridinin (123) is found in the organisms along with normal C 4 0 carotenoids and no doubt represents a carotenoid degradation product, albeit a more complex one than paracentrone (122), in that the carotenoid end groups are intact and degradation has taken place in the central carbon chain. Along with fucoxanthin (119) peridinin (123) appears to be a carotenoid of fundamental photosynthetic significance (Haxo, 1960).

9 (1968c) Weinheimer et al. 5 (1968c) Weinheimer et al. 9 (1968c) Weinheimer et al. 6 Weinheimer et al. (1968b) Irie et al. 1 Kurosawa et al. 2 Weinheimer et al. (1968c) Weinheimer and Washecheck (1969) Yamamura and Hirata (1963), Irie et al. (1969b) Irie et al. (1969b) Irie et al. (1969b) Irie et al. (1965b) Irie et al. (1966, 1970) Irie et al. (1966, 1970) Irie et al. (1966, 1970) Irie et al. (1969a) Suzuki et al. (1970) Sims et al. (1971) Fenical et al. (1971); Sims et al. (1972) Text no. 6 — — Reference 18 / .

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