Amathia convoluta

Narkowicz, . K., Blackman, A. J., Lacey, E., Gill, J. H., and Heiland, K. (2002). Convolutin-dole A and convolutamine H, new nematocidal brominated alkaloids from the marine bryozoan Amathia convoluta. J. Nat. Prod. 65, 938-941. 

Volutamides A-E (143-147), halogenated alkaloids of amino acid origin, have been isolated from the Atlantic bryozoan Amathia convoluta. Several of the volutamides deter feeding by potential predators and are toxic toward larvae of the co-occurring hydroid Eudendrium carneum, suggesting that these metabolites form the basis of an effective chemical defense. [114]. 

Several new brominated tryptamines and tryptophans have been described. The Tasmanian bryozoan Amathia convoluta contains convolutindole A (1342) (1319), and the North Sea bryozoan Flustra foliacea (Fig. 3.19) has afforded deformylflustrabromine B (1343) (1320), 1344, 1345, and deformylflustrabromine... 

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). 

Narkowicz CK, Blackman AJ, Lacey E, Gill JH, Heiland K (2002) Convolutindole A and Convolutamine H, New Nematocidal Brominated Alkaloids from the Marine Bryozoan Amathia convoluta. J Nat Prod 65 938... 

Kamano Y, Zhang H, Ichihara Y, Kizu H, Komiyama K, Pettit GR (1995) Convolutamy-dine A, a Novel Bioactive Hydroxyoxindole Alkaloid from Marine Bryozoan Amathia convoluta. Tetrahedron Lett 36 2783... 

Kamano Y, Kotake A, Hashima H, Hayakawa I, Hiraide H, Zhang H-P, Kizu H, Komiyama K, Hayashi M, Pettit GR (1999) Three New Alkaloids, Convolutamines F and G, and Convolutamydine E, from the Floridian Marine Bryozoan Amathia convoluta. Collect Czech Chem Commun 64 1147... 

Zhang H, Kamano Y, Kizu H, Itokawa H, Pettit GR, Herald CL (1994) Convolutamines A-E, Novel P-Phenylethylamine Alkaloids from Marine Bryozoan Amathia convoluta. Chem Lett 2271... 

Montanari AM, Fenical W, Lindquist N, Lee AY, Clardy J (1996) Volutamides A-E, Halogenated Alkaloids with Antifeedant Properties from the Atlantic Bryozoan Amathia convoluta. Tetrahedron 52 5371... 

Kamano, Y., Zhang, H., Ichihara, Y., and Kizu, H., Convolutamydine A, a novel bioactive hydroxy-oxindole alkaloid from marine bryozoan Amathia convoluta, Tetrahedron Lett., 36, 2783, 1995. 

The marine bryozoan Amathia convoluta produces convolutamine H (72) [61], and the Japanese gastropod Turbo marmorata has yielded the highly toxic (LD99 1-4 mg/ kg, mice) iodinated turbotoxins A (73) and B (74) [62[. The Palauan ascidian Botrylloides tyreum contains botryllamide G (75) [63], and several new psammaplins, for example psammaplin E (76), have been isolated from the sponge Pseudoceratina purpurea [64]. 

Another bryozoan, Amathia convoluta, has been found which also gives bryostatins 4-6, 3-5, and 8, 7. Examination of voucher specimens showed that some B. neritina occurred on the A. convoluta as a parasitic or epiphytic growth so that the true source of the compounds remains ambiguous although the authors concluded that bryostatin 8 was a genuine constituent of A. convoluta [11]. Investigation of a Tasmanian collection of A. convoluta [12] failed to show any antineoplastic activity which is characteristic of the bryostatins the bryozoan did however contain a new alkaloid (see Section 2.3.1). 

Zhang, H.-P., Kamano, Y., Kizu, H., Itokawa, H., Pettit, G. R., Herald, C. L. Convolutamines A-E, novel y -phenylethylamine alkaloids from marine bryozoan Amathia convoluta. Chem. Lett. 1994, 2271-2274. 

Alkaloid from the marine bryozoan Amathia convoluta. Exhibits cytotoxicity against murine P388 lymphocytic leukaemia. Oil. Racemic. 

Alkaloid from the marine bryozoan Amathia convoluta. Oil. 

CioH BrjNOa M 350.994 -Tetradecanoyl [158182-21-9]. Convolutamide A C24H35Br2N04 M 561.353 Isol. from the marine bryozoan Amathia convoluta. Exhibits cytotoxicity against LI210 murine leukaemia and KB human epidermoid carcinoma cells. Amorph. solid. [a]p —6.0 (c, 0.4 in CHCI3). Opt. rotn. and biol. activity refer to a 1 1.7 insep. mixt. with Convolutamide B. 

Zhang HP, Shigemori H, Ishibashi M, Kosaka T, Pettit GR, Kamano Y, Kobayashi J (1994) Convolutamides A-F, Novel y-Lactam Alkaloids frran the Marine Bryozoan Amathia convoluta. Tetrahedron 50 10201... 

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