Pseudoceratina

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

Lafi, F. F., Garson, M. J., and Fuerst, J. A. (2005). Culturable bacterial symbionts isolated from two distinct sponge species (Pseudoceratina clavata and Rhabdastrella globostellata) from the great barrier reef display similar phylogenetic diversity. Microb. Ecol. 50, 213-220. 

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]. 

A Papua New Guinea sponge, Pseudoceratina sp., contains the unusual alkaloids ceratamines A (1142) and B (1143), and a biogenesis involving histidine and tyrosine is proposed (1173). The fermentation broth from Aspergillus fischeri var. thermomutatus has yielded CJ-12662 (1144) and UK-88051 (1145) (1174). The former metabolite was confirmed by X-ray spectroscopy and partial synthesis. A marine-derived Streptomyces sp. produces the novel pyrrolizidine 5-chlorobohem-amine C (1146), which was shown not to be an isolation artifact (1175). The Chinese medicinal plant Huperzia serrata has furnished 2-chlorohyperzine E (1147) (1176). 

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). 

The Okinawan sponge Psammaplysilla purea that contains purealidins M-0 (2004-2006) also yields purealidins J (2078), K (2079), L (2080), P (2081), Q (2082), and R (2083) (1835). Purealidin J (2078) is the antipode of pseudocer-atinine A (2089). The Indian sponge Psammaplysilla purpurea, which is the source of purpurealidins F-H (2018-2020) and other bromotyrosines (vide supra), also contains purpurealidins A (2084), B (2085), C (2086), and D (2087) (1842). A Caribbean Pseudoceratina sponge has afforded the simple carboxylic acid 2088 (1868). The New Caledonian sponge Pseudoceratina verrucosa, which is the source of pseudoceratinine B (1990), also contains pseudo-ceratinines A (2089) and C (2090), the absolute configurations of which are shown (1829). 

Manzo E, van Soest R, Matainaho L, Roberge M, Andersen RJ (2003) Ceratamines A and B, Antimitotic Heterocyclic Alkaloids Isolated from the Marine Sponge Pseudoceratina sp. Collected in Papua New Guinea. Org Lett 5 4591... 

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... 

Ciminiello P, Fattorusso E, Magno S, Pansini M (1995) Chemistry of Verongida Sponges, IV. Comparison of the Secondary Metabolite Composition of Several Specimens of Pseudoceratina crassa. J Nat Prod 58 689... 

Benharref A, Pais M, Debitus C (1996) Bromotyrosine Alkaloids from the Sponge Pseudoceratina verrucosa. J Nat Prod 59 177... 

Thirionet I, Daloze D, Braekman JC, Willemsen P (1998) 5-Bromoverongamine, A Novel Antifouling Tyrosine Alkaloid from the Sponge Pseudoceratina sp. Nat Prod Lett 12 209... 

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... 

Pseudoceratina crassa Larva Lecithotrophic Coral, fish 68, 72... 

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[. 

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