Psammaplysilla purpurea

Yagi, H., Matsunaga, S., and Fusetani, N. (1993). Purpuramines A-I, new bromotyrosine-derived metabolites from the marine sponge Psammaplysilla purpurea. Tetrahedron 49, 3749-3754. 

Four minor metabolites, psammaplins B-D (503-505) and presammaplin A (506) were isolated from Psammaplysilla purpurea, in addition to psammaplin A (500). Psammaplin B (503) is a thiocyanate bromotyrosine derivative, while psammaplin C (502) is a sulfanamide. Psammaplin D (505) displayed antimicrobial activity and mild tyrosine kinase inhibition [429]. The psammaplins Ai (507) and A2 (508) and aplysinellins A (509) and B (510) were isolated from Aplysinella rhax from both Pohnpei and Palau. These compounds inhibit famesyl protein transferase and leucine aminopeptidase [430]. Another sample of A. rhax from the Great Barrier Reef, Australia contained psammaplin A 11 -sulfate (511) and bisaprasin ll -sulfate (512), both of which inhibited [3H]-l,3-dipropyl-8-cyclopentylxanthine binding to rat brain adenosine Ai receptors [431]. 

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). 

Venkateswarlu Y, Chavakula R (1995) Brominated Benzeneacetonitriles, the Dibromotyro-sine Metabolites from the Sponge Psammaplysilla purpurea. J Nat Prod 58 1087... 

Venkateswarlu Y, Venkatesham U, Ramo Rao M (1999) Novel Bromine-Containing Constituents of the Sponge Psammaplysilla purpurea. J Nat Prod 62 893... 

Ravinder K, Vijender Reddy A, Raju TV, Venkateswarlu Y (2005) A New Dibromotyro-sine-Derived Metabolite from the Sponge Psammaplysilla purpurea. Arikov 51... 

Tilvi S, Rodrigues C, Naik CG, Parameswaran PS, Wahidhulla S (2004) New Bromotyro-sine Alkaloids from the Marine Sponge Psammaplysilla purpurea. Tetrahedron 60 10207... 

Bromotyrosine-derived metabolites are often encountered in marine sponges of the families Aplysinidae and Pseudocer-atidae, in particular Pseudoceratina (= Psammaplysilla) purpurea. They show a variety of biological activities, which include antimicrobial, enzyme inhibitory, and antifouling activities. Psammaplysin A (47) is antimicrobial, cytotoxic, and antifouling, whereas psammaplin A (48) is an inhibitor of histone deacetylase (2). The marine sponge lanthella basta synthesizes at least 25 bastadins that are linear or cyclic peptides composed of four bromotyrosine residues [bastadin 5 (49)] and show antimicrobial, cytotoxic, and enzyme inhibitory activities as well as interaction with Ca + channels (21). 

Sponges of the order Verongida contain numerous metabolites having a spiroisoxazoline system, which can be derived from bromotyrosine. A. from Aplysina fis-tularis, C24H26Br4N40s, Mr 818.11, mp. 134-137 °C, [o]d +252° psammaplysin A from Psammaplysilla purpurea with a 1,6-dioxa-2-aza[4,6]undecane system ... 

Copp, B. R., Ireland, C. M., Barrow, L. R. Psammaplysin C a new cytotoxic dibromotyrosine-derived metabolite from the marine sponge Druinella (= Psammaplysilla)purpurea. J. Nat. Prod. 1992, 55, 822-823. 

Isol. from the marine sponge Psammaplysilla purpurea. Oil. Jimenez, C. et al. Tetrahedron, 1991, 47, 2097 isol, pmr, cmr, ms)... 

Rotem, M., S. Carmely, Y. Kashman, and Y. Loya Two New Antibiotics from the Red Sea Sponge Psammaplysilla purpurea. Total C-NMR Line Assignment of Psammaplysins A and B and Aerothionin. Tetrahedron 39, 667 (1983). 

The other series is the bastadins, named after the Australian species lanthella basta, from which most bastadins were isolated (Kazlauskas et al., 1981). They are formally peptides that are derived, as in other verongid sponges, from bromotyrosine. With the exception of bas-tadin 14, which was isolated from Psammaplysilla purpurea, and bastadins 22 and 23 from Dendrilla cactos, almost all bastadins were extracted from species of the genus lanthella, most often from lanthella basta. The latest member of the series is bastadin 26, isolated from the Australian species lanthella flabelliformis (Calcul et al., 2010b Carroll et al, 2010). 

Jimenez, C. and Crews, P. (1991) Novel marine sponge-derived aminoacids 13. Additional psammaplin derivatives from Psammaplysilla purpurea. Tetrahedron, 47, 2097-2102. 

Carney, J.R., Scheuer, P.J., and Kelly-Borges, M. (1993c) A new bastadin from the sponge Psammaplysilla purpurea. J. Nat. Prod., 56, 153-157. 

Additional aromatic bromotyrosine derivatives, 35-41, were isolated from Psammaplysilla purpurea, Verongia aerophoba, V. archeri, and Pseudoceratina crassa, respectively 28-33). 

Different iV-methylation derivatives of moloka iamine, aplysamine 1 (54) 44), purealidin F (55), and G (56) 45), were obtained from an Australian sponge Aplysina sp. and the Okinawan sponge Pscanmaplysilla purea, respectively. 3,5-Dibromo-4-(3-dimethylaminopropoxy)phenethyl carbamic acid methyl ester (57) and its salt 58 were obtained as the first bromotyrosine derivatives containing a carbamate group from an Indian sample of Psammaplysilla purpurea 46), along with 59 47,48). 

Xynas and Capon reported aplysamine 2 (172) from an Australian marine sponge Aplysina sp. in 1989 (44). Aplysamines 3 (173), 4 (174), and 5 (175) were isolated from the Hawaiian sponge Psammaplysilla purpurea by Scheuer s group (118). All of these alkaloids exhibited cytotoxic activity, while aplysamine 3 and 4 showed mild antibacterial activity against Staphylococcus aureus. Alkaloids 176 and 177 were isolated from the sponge P. purpurea collected in Okinawa by an Indian group (119,120). 

Purpuramines K (190) and L (191), isolated from the Indian sponge Psammaplysilla purpurea, exhibited antimicrobial activity against both Gram positive and Gram... 

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