Psammaplysilla

Quinoa E, Crews P. (1987) Phenolic constituent of Psammaplysilla Tetrahedron Lett 28 3229-3232. 

Ishibashi, M., Tsuda, M., Ohizumi, Y., Sasaki, T., and Kobayashi, J. (1991). Purealidin A, a new cytotoxic bromotyrosine-derived alkaloid from the Okinawan marine sponge Psammaplysilla purea. Experientia 47, 299-300. 

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. 

There have been three reports of the same dimeric disulfide. It was first isolated from an unidentified sponge from Guam and the structure elucidated by analysis of spectral data. The (E,E) stereochemistry of the disulfide (500) was defined by comparing the I3C NMR spectroscopic data with those of the (E,Z)-isomer (501) that was obtained as an unstable minor product [425]. Compound 500 was isolated from a species of Psammaplysilla and was called psammaplin A [426]. It was also isolated from Thorectopsamma xana, collected from the same location in Guam, together with a minor dimeric metabolite bisaprasin (502). Both compounds inhibited growth of Staphylococcus aureus and Bacillus subtilis [427]. Psammaplin A (bisprasin) (500) was later isolated from a Dysidea species of sponge and shown to act on Ca2+-induced Ca2+ release channels of skeletal muscle [428]. 

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). 

Purealin, another brominated tyrosine metabolite of the sponge Psammaplysilla purea, blocks the sliding movement of sea urchin Anthocidaris crassispina sperm flagella (2537). Numerous sponge metabolites are feeding deterrents to predatory... 

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

Kobayashi J, Honma K, Tsuda M, Kosaka T (1995) Lipopurealins D and E and Purealidin H, New Bromotyrosine Alkaloids from the Okinawan Marine Sponge Psammaplysilla purea. J Nat Prod 58 467... 

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... 

The key structure of antimicrobial marine natural product, araplysillin-I (28), which was isolated from Psammaplysilla arabica, was synthesized by spiro-annulation of o-phenolic oxime-amide (147) with PIDA [104] (Scheme 18). 

PurealinJ (brominated polycyclic aryl imidazole) Psammaplysilla purea (sea sponge) CaM (cAMP PDE, MLCK) [modulates smooth muscle myosin]... 

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). 

Purealidin D (114) was isolated from the Okinawan sponge Psammaplysilla purea as an inhibitor of Na+, K+-ATPase. Its structure was determined using FABMS, HRFABMS, IR, UV, and one- and two-dimensional H and NMR [321]. 

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