Chondria armata, domoic acid

Alkaloids derived from glutamic acid, other than y-aminobutyric acid (GABA), include kainic acid isolated from Digenea simplex, domoic acid isolated from Chondria armata, acromelic acids isolated from Clitocybe acromelalga, ibotenic acid isolated from Amanita strobiliformis Amanita pantherina), and tricholomic acid isolated from Tricholoma musucaria, and are described in this chapter. 

Although isolated in 1959 (125) from the now rare red alga Chondria armata Okamura (Rhodomelaceae), domoic acid (77) was given a tentative structure... 

Daigo K (1959) Constituents of Chondria armata. IV. Determination of domoic acid. Yakuga Zasshi 79 360-364... 

Domoic acid (Fig. 28,80) (263) is a neuro-phycotoxin responsible for the mortality of wildlife and for amnesic shellfish poisoning (ASP) of humans during algal bloom. Domoic acid was first isolated from the red alga Chondria armata ( domoi in Japanese), and it is produced also by diatoms, such as Pseudo-nitzschia spp. For the latter, evidence has been presented that it is involved in iron acquisition (307). 

Jaspamide (17), previously mentioned in Section 17.3, is a modified peptide isolated from a Jaspis sponge. Jaspamide shows insecticidal activity against Heliothis virescens with an LCS0 of 4 ppm, as compared to 1 ppm for azadirachtin. Jaspamide (17), showed more than 72% mortality at 100 ppm to both southern com rootworm and tobacco budworm. Iso-domoic acids A (40), B, and C are novel amino acids from the red alga Chondria armata. They... 

The red alga Digenea simplex has been used for the treatment of roundworm disease for centuries. Its active principle is kainic acid. The related domoic acid is a constituent of another red alga, Chondria armata, used for the same purpose. These compounds, known as kainoids, are potent neurotoxins and excitatory amino acids. Kainoids are important tools in neurophysiological research. Domoic acids are also produced by diatoms and were responsible for the shellfish poisonings known as amnesic shellfish poisonings that occurred in Canada in 1987. 

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. 

The Japanese have used extracts from Chondria armata as an insecticide, the active component being (-)-domoic acid 4.27 Insecticidal activity is found to depend on the nature of the kainoid C-4 substituent. 

Zaman, L., Arakawa, O., Shimosu, A., Onoue, Y., Nishio, S., Shida, Y, and Noguchi, T. 1997. Two new isomers of domoic acid from a red alga, Chondria armata. Toxicon 35, 205-212. 

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]. 

Domoic acid is a naturally occurring excitatory amino acid that was identified as the toxin responsible for an outbreak of amnesic shellfish poisoning that occurred in Canada in 1987 following consumption of contaminated blue mussels (Mytilus edulis) [1] as well as numerous other outbreaks worldwide. The parent compound is a tricarboxylic amino acid produced by certain marine organisms, the best characterized of which are the red alga Chondria armata and the planktonic diatom Nitzschia pungens, although other species are also known to produce domoic acid (for review, see Reference 2). 

Zaman, L. et ah. Two new isomers of domoic acid from a red alga Chondria armata, Toxicon., 35, 205, 1997. 

The isomeric acromelic acids A and B display a powerful neuroexcita-tory action and are structurally related to the anthelmintic kainic acid (406,407) and domoic acid (408), the known principles from the marine red algae Digenea simplex and Chondria armata, respectively. Both of the latter amino acids, the structures of which were determined by chemical and X-ray studies, attracted considerable interest as well because of their... 

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). 

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). 

Chondria armata. The domoic acid content was investigated in seaweed from 3 areas in Kagoshima Pref The Tokunoshima sample (dried) collected in June 1993 showed a very high score of 4,300 ppm. Dried C. armata from this area was formerly collected and... 

Figure 1. HPLC analysis for domoic acid of red algae (1) Chondria armata (994 ppm), (2) Coelothrix irregularis (6 ppm), (3) Digenea simplex (<1 ppm), (4) standard of domoic acid.

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