Domoic isodomoic

XIII. Future prospects the domoic/isodomoic acid family 94... 

Domoic acid 4 (Figure 3) was isolated in 1958 from another Japanese marine alga, Chondria armata.4 Determination of the stereochemistry at C-5 proved problematic until it was confirmed as R by Ohfune in a total synthesis achieved in 1982.5 Structurally related derivatives, isodomoic acids A-F and domoilactones A and B have subsequently been isolated from Chondria armata. 

Nomoto, K., Takemoto, T, and Maeda, M. 1992. Conformational feature of neuroactive domoic acid X-ray structural comparison with isodomoic acid A and alpha-kainic acid. Biochem Biophys Res Commun 187, 325-331. 

Wright, J.L.C., Falk, M., Mcltmes, A.G., and Walter, J.A. 1990. Identification of isodomoic acid D and two new geometrical isomers of domoic acid in toxic mussels. CanJ Chem 68,22-25. 

Chemical investigations dealing with the identification of toxic compound(s) responsible for the toxicity of a mussel, Mytilus edulis, from eastern Prince Edward Island, Canada, has resulted in the identification of domdc acid [116] (95). Domoic acid was originally isolated over 30 years ago from the red alga Chondria armata (96). A further investigation of the toxic mussels has resulted (97) in the isolation of domoic acid D [117] and two geometric isomers, isodomoic acid E3 [118] and isodomoic acid E4 [119]. 

In addition to the parent compound, a number of isomers of domoic acid have been identified (Figure 20.2). Isodomoic acid A, B, and C are present in small amounts in the red alga C. armata... 

Chemistry of some pyrrolidine derivatives (domoic acid, isodomoic acids) and their analogs 05T5713. 

Domoic add is one of the rare nitrogenous secondary metabolites encormtered in the diatoms. Isodomoic acids A-F, all isomers of domoic add, have been isolated from the red alga Chondria armata (Chapter 13). For an overall study on ASP and domoic adds, see Daranas, Norte, and Fernandez, 2001 Clayden, Read, and Hebditch, 2005 Kotaki et al (2005), Ramsdell (2007) and Pulido (2008). 

Clayden, J., Read, B., and Hebditch, KR. (2005) Chemistry of domoic acid, isodomoic acids, and their analogues. Tetrahedron, 61, 5713— 5724. 

Later, but always with Chondria armata, a series of isomers of domoic acid were isolated, isodomoic adds A-H, as well as domoilactones A and B all these amino acids have insecticidal and anthelmintic properties (Tanaka et al, 1985 Maeda et al, 1986, 1987 Zaman et al, 1997). Isodomoic acids D-F were isolated in Canada from mussels made toxic by diatoms (Wright et al, 1990). 

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