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Chemistry of marine natural products by Paul J. Scheuer

By Paul J. Scheuer

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It has been found 1916) to occur widely, as, oils of species It has sinceand been found to yeast. occur Karrer widely,and as, in several many seed oils of ofshark. , in many(1930) seed oils of flowering plants and in synthesized brewer's yeast. Karrer and co-workers established its structure and it (Karrer co-workers Helfenstein, (1930) 1931). established its structure and synthesized it (Karrer and Helfenstein, 1931). 2. 2. THE T H E ASTEROSAPONINS ASTEROSAPONINS The The echinoderm echinoderm class class of of the the asteroids asteroids (sea (sea stars, stars, starfish) starfish) is is quite quite different different in in appearance appearance from from the the holothurians.

Peridinin (123) is the principal carotenoid pigment of dinoflagellates, marine and freshwater, and was first isolated in 1890 (Schutt, 1890) from the marine genera Ceratium and Peridinium. It has also been isolated from the zooxanthellae of corals, clams, and sea anemones. D. Carotenoids 51 For the successful structural work peridinin (123) was isolated from the zooxanthellae of the sea anemone Bunodactis (syn. Anthopleura) xanthogrammica, from a bloom of the dinoflagellate Gonyaulax polyedra, and from cultures of Cachonina hiei and Amphidinium operculatum.

1. T H E C 20 COMPOUNDS The sea hare constituent, designated aplysin-20, is a bicyclic diterpenoid, which was isolated from Aplysia kurodai along with the three sesquiterpenoids aplysin (27), debromoaplysin (26), and aplysinol (28). The structure of aply5 sin-20, mp 146°-147°, [ α β ° - 7 8 . 1 ° , was determined by X-ray diffraction techniques (Matsuda et al, 1967) to be 49. Aplysin-20 possesses a normal (unrearranged) isoprenoid skeleton; but as the authors point out, the compound has the unusual features of an axial hydroxyl at C-8 and an equatorial bromine at C - 3 .

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