By P.J. Scheuer, J. Darias
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Extra info for Marine Natural Products Volume 1: Chemical and Biological Perspectives
The absolute configurations of C-6 and C-7 for 5 6 laureatin and isolaureatin, however, proved to have opposite chiralities from those of laurencin. -pentadecanediol (10). Chemical and biogenetic arguments were used to denote the relative stereochemistry and absolute configuration of C-9, C-10, C-l2, and C-l3 Scheme 2 49 2. Algal Nonisoprenoids (Irie et al, 1970). Since C-7 was found to be S for both laureatin and isolaureatin, it followed that C-9 in 5 was R and C-10 in 6 was S. Monodebromohexahydrolaureatin (11), obtained as shown in Scheme 3, underwent a facile E2 elimination and ring opening to an oxocinol (characterized as the acetate 12), strongly suggesting that the bromine was trans to the ether oxygen and therefore R.
A very common dinoflagellate in warm water, Noctiluca scintillans, is also said to be toxic. However, Morton and Twentyman (1971) investigated the organism and shellfish collected in H o n g Kong waters and did not find noticeable toxicity. The only reported freshwater dinoflagellate bloom from Peridinium polonicum caused an extensive fish kill. Okaichi and Hashimoto (1962) isolated a substance, glenodinine, toxic to both freshwater and marine fish. Death seems to be preceded by excitement, followed by reduction of response to stimuli.
Schantz, E. , Schnoes, H. , and Strong, F. M. (1974). Biochem. Biophys. Res. Commun. 59, 1219-1225. Ghazarossian, V. , Schantz, E. , Schnoes, H. , and Strong, F. M. (1976). Biochem. Biophys. Res. Commun. 68, 776-780. Grindley, J. , and Heydorn, A. E. F. (1970). S. Afr. J. Sci. 66, 210-213. Hafemann, D. , and Houston, A. H. (1971). Fed. Proc, Fed. Am. Soc. Exp. Biol. 30, 255. Halstead, B. W. (1965). In "Venomous Marine Animals of the World," Vol. I, pp. 157-226. S. Govt. C. , Dang, L. , and Noguchi, T.