Brominated indole alkaloids

Chbani, M. Pals, M. Delauneux, J.M. Debitus, C. (1993) Brominated indole alkaloids from the marine tunicate Pseudodistoma arborescens. J. Nat. Prod., 56,99-104. 

Meridianins, brominated indole alkaloids from the tunicate Aplidium meridianum, show cytotoxicity against LMM3 (murine mamarian adenocarcinoma cell line) with IC5o values of 11.4 jM for meridianin B (25), 9.3 iM for meridianin C (26), 33.9 iM for meridianin D (27), and 11.1 aM for meridianin E (28) [41]. 

Fig. 3.19 Flustrafoliacea, a North Sea bryozoan and a producer of many bromotryptamines and brominated indole alkaloids, such as 1343-1346 (Photo A. D. Wright)...

From North Sea Bryozoan Flustra foliacea) several, brominated indole alkaloids have been isolated. These include deformylflustramine and flustramine. Deformylfrustrabromine A and deformylfrustrabromine B... 

Benzo-derivatives 46,48 Benzopyranopyrroles 55 Benzothiazoles 67 Benzothiophenes 62 Benzoxazines 253 Benzoxazoles 249 Biginelli cyclocondensation 34 Bis(indole)alkaloids 271 Bromination 20... 

Malbrancheamide (60) represents a novel type of CaM inhibitors although other natural indole alkaloids such as the unusual indole-carbazole alkaloids from a culture broth of a Nocardiopsis sp, namely K-252a-K252d, the brominated P-carbolines eudistomidins A and C, obtained... 

Bifiilco, G. Bruno, I. Riccio, R. Lavayre, J. Bourdy, G. (1995A) Further brominated bis- and tris-indole alkaloids from the deep-water New Caledonian marine sponge Orina sp. J. Nat. Prod. 58, 1254-60. 

Morris, S.A. Andasen, R.J. (1990) Brominated bis(indole) alkaloids from the marine sponge Hexadella sp. Tetrahedron, 46, 715-20. 

Bifulco G, Bruno I, Riccio R, Lavayre J, Bourdy G (1995) Further Brominated Bis- and Tris-Indole Alkaloids from the Deep-Water New Caledonian Marine Sponge Orina sp. J Nat Prod 58 1254... 

As the azocinoindole 40 constitutes the tricyclic substructure of the indole alkaloid apparicine , we attempted to improve the cyclization yield. Satisfactorily, the regioselectivity was completely switched to the 8-endo mode when the alkene acceptor was substituted at the internal position by a bromine atom. Thus, cyclization of selenoester 43 led to the desired target 40 as the only reaction product in 75% yield. Clearly, the bromine atom not only sterically prevented the competitive 1-exo attack, but also benefited the cyclization by activation of the double bond. It should be noted that similar halogen-controlled 8-endo cyclizations are known in the literature, but involving amidyl-type radicals <06OL2647>. 

Bryozoan alkaloids. A group of indole alkaloids from marine bryozoans. There are 4000 bryozan species widely distributed in the oceans (down to a depth of 8000 m) and waters worldwide. B. a. are brominated... 

Notoamides A-R could currently be the only indole alkaloids isolated from the culture of a fxmgus assodated with a mollusk. Produced from an Aspergillus collected on the common mussel, Mytilus edulis, from Japan (Noto Peninsula), notoamides A-O are cytotoxic for the HeLa " cell line (Kato et cd., 2007 Tsukamoto et al., 2008, 2009a, b, 2010). Postulated as a biosynthetic precursor of notoamides, notoamide E was isolated in 2009 and the first biosynthetic gene cluster was characterized in 2010 (Ding et al., 2010). Notoamide P is currently the only brominated notoamide. 

Lastly, trachycladindoles A-G are a series of cytotoxic brominated indole-dihydroimidazole alkaloids isolated from Trachycladus laevispiculifer from the Great Australian Bight (Capon, Peng, and Dooms, 2008). 

Bifulco, G., Bruno, 1., Minale, L., Ricdo, R., Calignano, A., and Debitus, C. (1994b) ( )-Gelliusmes A and B, two diastereomeric brominated tris-indole alkaloids from a deep water New Caledonian marine sponge Gellius or Orina sp.).J. Nat. Prod., 57,1294-1299. 

Butler, M.S., Capon, R.J., and Lu, C.C. (1992) Psammopemmins (A-C), novel brominated 4-hydroxy-indole alkaloids from an Antarctic sponge, Psammopemma sp. Aust. J. Chem., 45,1871-1877. 

Most alkaloids of dictyoceratid sponges are indole alkaloids or related bis-indolic derivatives, derivatives of tryptophan, with or without a bromine atom, and of P-carboline. This finding is not specific to Dictyoceratida, or even to sponges. Some atypical structures, such as derivatives of imidazole, guanidine or pyridine, have also been characterized in some species. 

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