Pseudoceratina purpurea

Pseudoceratina purpurea inhibition of both histone deacetylase and DNA methyltransferase. The Journal of Organic Chemistry, 68, 3866-3873. 

Other biologically active bromotyrosine-derived metabolites of marine origin include aeroplysinin, Fig. (48) as cytotoxic and tyrosine kinase inhibitor [382,383], fistularin isolated from Aplysina circheri which exhibited antiviral activity [384], and ceratinamides A and B, antifouling metabolites from Pseudoceratina purpurea [385],... 

Psammaplysin E (84), ceratinamine (85), and molokaiamine (86) from the sponge Pseudoceratina purpurea exhibit potent cytotoxicity against P-388 murine leukemia cells with IC50 values of 2.1, 3.4, and 2.1 pg/ml, respectively [74]. Recently, the related waianaeamines have been isolated from an undescribed verongid sponge from Molokai Island [75]. 

The bromotyramine derivatives ceratinamide A (136) and psammaplysin A (137) from the sponge Pseudoceratina purpurea inhibit the settlement and metamorphosis of cyprid larvae of the barnacle Balanus amphitrite (ED50 0.10 and 0.27 (Jg/ml). Interestingly, psammaplysin A induces larval metamorphosis of the ascidian Halocynthia roretzi (ED 0o 1.2 (Jg/ml) [74]. 

The antifouling sponge metabolite pseudoceratidine (1245) was characterized from the Japanese Pseudoceratina purpurea (1253). This spermidine derivative has excellent larval settlement and metamorphosis inhibitory activity against the barnacle Balanus amphitrite (ED50 = 8.0 pig cm-3), and is the first example of an antifouling spermidine derivative. The four tauroacidins A (1246/1247) and B (1248/1249), with tyrosine kinase inhibitory activity, were isolated from the... 

Fig. 3.29 Pseudoceratina purpurea, a Papua New Guinea sponge that contains several psarnma-plins such as 1996-2001 (Photo P. Crews)...

F (1997) is a potent histone deacetylase inhibitor, and psammaplin G (1998) is a potent DNA methyltransferase inhibitor. A Southern Japanese version of Pseudoceratina purpurea has yielded pseudoceratins A (2002) and B (2003) (1834). 

Tsukamoto S, Kato H, Hirota H, Fusetani N (1996) Pseudoceratidine A New Antifouling Spermidine Derivative from the Marine Sponge Pseudoceratina purpurea. Tetrahedron Lett 37 1439... 

Fusetani N, Masuda Y, Nakao Y, Matsunaga S, van Soest RWM (2001) Three New Bromotyrosine Derivatives Lethal to Crab from the Marine Sponge, Pseudoceratina purpurea. Tetrahedron 57 7507... 

Jang J-H, van Soest RWM, Fusetani N, Matsunaga S (2007) Pseudoceratins A and B, Antifungal Bicyclic Bromotyrosine-Derived Metabolites from the Marine Sponge Pseudoceratina purpurea. J Org Chem 72 1211... 

Kijjoa A, Bessa J, WattanadilokR, SawangwongP, Nascimento MSJ, Pedro M, Silva AMS, Eaton G, van Soest R, Herz W (2005) Dibromotyrosine Derivatives, a Maleimide, Aplysamine-2 and Other Constituents of the Marine Sponge Pseudoceratina purpurea. Z Naturforsch 60b 904... 

Takada N, Watanabe R, Suenaga K, Yamada K, Ueda K, Kita M, Uemura D (2001) Zamamistatin, a Significant Antibacterial Bromotyrosine Derivative, from the Okinawan Sponge Pseudoceratina purpurea. Tetrahedron Lett 42 5265... 

Tsukamoto, S., Kato, H., Hirota, H., and Fusetani, N., Ceratinamides A and B new antifouling dibromotyrosine derivatives from the marine sponge Pseudoceratina purpurea, Tetrahedron, 52, 8181, 1996. 

Thorectopsamma xana Poecillastra sp. / Jaspis sp. association Aplysinella rhax Pseudoceratina purpurea... 

A spermidine derivative with two 4,5-dibromopyrrole-2-carbamyl units, pseudo-ceratidine (120), has been isolated from the sponge Pseudoceratina purpurea as an antifouling compound [145]. 

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]. 

Numerous sponge metabolites that incorporate multiple tyrosine units are known [1], and some recent discoveries of compounds containing two tyrosines include tokaradine A (77) from Pseudoceratina purpurea [65], the novel bromotyrosine... 

The structure of zamamistatin (90) previously isolated from the Okinavran Pseudoceratina purpurea [79] has been revised to that shovm [80[. Another novel bromotyrosine sponge metabolite is kuchinoenamine (91) from Hexadella sp. [59[. 

Crews has also formulated a biosynthetic pathway for the disulfide bromotyrosine psammaplins from the sponge Pseudoceratina purpurea [64,126]. The structurally unique ma edamines (80, 81) may be derived from a dehydro derivative of aplysa-mine-2 or purpuramine H via cyclization and dehydroxylation [69]. The numerous bromotyrosine alkaloids that contain an aminopropanol unit, such as nakirodin A (71), may be derived from a homoserine unit through decarboxylation [60]. The... 

Ceratinamides A (68) and B (69), antifouling bromotyrosine derivatives, were isolated from marine sponge Pseudoceratina purpurea through a bioassay -guided isolation (Figure 4) [38]. Ceratinamide A (68) is structurally similar to psammaplysin A (27) and has one formyl group at the A-terminus. 

Jang, J.-H., Van Soest, R.W.M., Fusetani, N., and Matsimaga, S. (2007) Pseudoceratins A and B, antifimgal bicyclic bromotyrosine-derived metabolites from the marine sponge Pseudoceratina purpurea. J. Org. Chem., 71.1211-1217. 

Takada, N., Watanabe, R., Suenaga, K, Yamada, K., Ueda, K., Kita, M., and Uemura, D. (2001) Zamamistatm, a significant antibacterial bromotyrosine derivative, from the Okinawan sponge Pseudoceratina purpurea. Tetrahedron Lett., 42, 5265—5267. 

Schoenfeld, R.C. and Ganem, B. (1998) SynAesis of ceratinamine and molokaiamine antifouhng agents from Ae marine sponge Pseudoceratina purpurea. Tetrahedron Lett., 39,4147-4150. 

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