Invertebrates macrolides from

Macrolides from algae and invertebrates, except for insects, are precisely described in Chapter 2. Therefore, compounds having unique skeletons produced only by algae or invertebrates are merely mentioned here. The lists of macrolides produced by algae and invertebrates are shown in Tables X and XI, respectively. 

Matsunaga, S. (2006) Trisoxazole macrolides from Hexabranchus nudibranchs and other marine invertebrates. Prog. Mol SubcM. Biol., 43, 241-260. 

Steroid chemistry, the glamor area of natural product research in the years following World War II, was replaced by macrolides, alkaloids, and prostanoids. Sterol chemistry again became exciting when an unanticipated rich diversity of marine invertebrate sterols were isolated, notably from sponges. After pioneering research in Italy, the field was reborn in Carl Djerassi s laboratory at Stanford. As a result, we now have a better and more detailed knowledge of sterol biosynthesis than of any other class of marine natural products. The authors of Chapter 1 are Stanford alumni. 

ABSTRACT Marine invertebrates such as ascidians, sponges and others are a prolific source of bioactive secondary metabolites. We have isolated a variety of marine natural products from the Okinawan marine invertebrates by using the sea urchin egg assay. Our recent work, the isolation, structure determination and activities of chlorinated macrolides, sesterterpenic acids, a bromotyrosine derivative, acetogenin derived endoperoxides, diterpene alkaloids, sesquiterpene quinones and spiro-sesquiterpenes, is presented in this article. The syntheses of these metabolites are also described. 

Strobel and co-workers isolated haterumalide NA/oocydin A (2) from bacteria Sermtia marcescens [10]. Haterumalide NA was also obtained from a soil bacterium [11]. The isolation of similar compounds from two unrelated invertebrates such as the ascidian Lissoclinum sp. and the sponge of Ircinia sp., and the microorganisms, supports the potential microbial origin of haterumalides [12-15]. Although more than 200 marine macrolides have been recorded since the first isolation of the aplysiatoxins, halogenated marine macrolides are rarely found [16, 17]. 

Bryostatins. The bryostatins are a group of cytotoxic marine macrolides, isolated from invertebrate filter feeders, that exhibit promising anticancer activity (Scheme 9-36). Two completed total syntheses of the bryostatins have demonstrated the versatility and power of aldol reactions in the concise assembly of complex polyketides. 

The isolation of this 20-membered class of macrolidic cytotoxins from the fouling invertebrate Bugula neritina over 30 years ago has led to massive collections of the nominal producing organism and to very elegant syntheses of various components. 

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