Amathia wilsoni

Amathaspiramide E (128) from the New Zealand bryozoan Amathia wilsoni exhibits strong activity in the antiviral assay against Polio virus [102],... 

Tyrosine-derived metabolites in this section do not include spiro-cyclohexadienyl-isoxazolines and related compounds (Sect. 3.22.3.3) or bastadins (Sect. 3.22.3.4), but they do include tyrosine-derived alkaloids that were covered in the Alkaloids section in the first survey (1). The prolific bryozoan Amathia convoluta, collected in Tasmania, has yielded amathamide G (1953) (1814), the latest of several amath-amide alkaloids from the genus Amathia (1). A Florida collection of this animal furnished the new convolutamines A-E (1954—1958) (1815), F (1959), and G (1960) (1425), and a Tasmanian sample of this bryozoan afforded convolutamine H (1961) (1319). A study of Amathia convoluta from the North Carolina coast has yielded volutamides A-E (1962-1966) (1816). Volutamides B and C reduce feeding by the pinfish (Lagodon rhomboids) and the urchin (Arbacia punctulata), respectively, and volutamides B and D are toxic toward larvae of the hydroid Eudendrium carneum. The New Zealand Amathia wilsoni contains the six novel amathaspiramides A-F (1967-1972) (1817). 

Morris BD, Prinsep MR (1999) Amathaspiramides A-F, Novel Brominated Alkaloids from the Marine Bryozoan Amathia wilsoni. J Nat Prod 62 688... 

Walls, J.T., Blackman, A.J., and Ritz, D.A., Distribution of amathamide alkaloids within single colonies of the bryozoan Amathia wilsoni, J. Chem. Ecol., 17, 1871, 1991. 

Energy-dispersive X-ray microanalysis has shown that the brominated alkaloids present in the Australian bryozoan Amathia wilsoni may be associated with a surface bacterium,182 consistent with a role in chemical defense. Tambjamines A-D 149, 150, 160, and 161, from the bryozoan Sessibugula translucens and nudibranch predators... 

The amathamides (Scheme 10), alkaloids from the Tasmanian marine bryozoan Amathia wilsoni, have been investigated as a function of geographical location of the collected material (152). Populations from the same location did not exhibit qualitative variations in alkaloid content. However, collections from different, geographically proximate locations gave widely varying alkaloid patterns (Table 1.). 

Scheme 10. Structures of the amathamide alkaloids, amathamide A [1], B [2], C [3], D [4], E [5], and F [6] from the marine bryozoan Amathia wilsoni.

Carroll, A. R, Duffy, S., Sykes, M., Avery, V. M. Wilsoniamines A and B novel alkaloids from the temperate Australian bryozoan, Amathia wilsoni. Org. Biomol. Chem. 2011,9, 604-609. 

Blackman, A. J., Matthews, D. J. Amatharrride alkaloids from the marine bryozoan Amathia wilsoni Kirkpatrick. Heterocycles 1985, 23,2829-2833. 

Blackman, A. J., Green, R. D. Further amathamide alkaloids firrm the bryozoan Amathia wilsoni. Aust. J. Chem. 1987, 40, 1655-1662. 

Blackman, A. J., Fu, S.-L. A y0-phenylethylamine-derived possible biosynthetic precursor to the amathamides, alkaloids from the bryozoan Amathia wilsoni. J. Nat. Prod. 1989, 52, 436-438. 

Osuna, M. R, Aguirre, G., Somanathan, R, Molins, E. Asymmetric synthesis of amathamides A and B novel alkaloids isolated from Amathia wilsoni. Tetrahedron Asymmetry 2992, 13,2261-2266. 

Morris, B. D., Prinsep, M. R. Amathaspiramides A-F, novel brominated alkaloids from the marine bryozoan Amathia wilsoni. J. Nat. Prod. 1999, 62, 688-693. 

In early 2012, Arash came across the amathaspiramides (la-f), a family of marine alkaloids that were isolated in 1999 by Prinsep and coworkers from a New Zealand collection of the bryozoan Amathia wilsoni (Figure 1). The structures were determined by detailed NMR analysis, including NOESY... 

Some species of the genus Amathia contain several amides that are probably formed from phenylalanine and N-methylproline or proline. Amathamides A-F were isolated from the species Amathia wilsoni harvested in Tasmania (Blackman and Matthews, 1985 Blackman... 

Amathaspiramides A-F form an original group of alkaloids isolated from a New Zealand form of Amathia wilsoni. The cytotoxic activities of these amides are moderate, but amathaspiramide E has a strong activity against the poliomyelitis virus (Morris and Prinsep, 1999). 

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