Reniera sarai

Alkylpyridines supposedly lie also along another biosynthetic route, affording pofymeric pyridinium compounds in marine haliclonid sponges the Indo-Pacific Callyspongia fibrosa (Davies-Coleman 1993), the Caribbean Amphimedon compressa (Albrizio 1995), and the Mediterranean Reniera sarai (Sep5i6 1997). 

Sqjcic, K. Guella, G. Mancini, I. Pi ra, F. Dalla Sara, M. Maiestrina, G. Tubbs, K. Macek, P. Turk, T. (1997) Characterization of anticholinesterase-active 3-all lpyridinium polymers frmn the marine sponge Reniera sarai in aqueous solution. J. Nat. Prod., 60, 991-6. 

The Mediterranean sponge Reniera sarai is a rich source of new macro-cyclic alkaloids, named sarains, which may be biogenetically related to petrosin (246) or araguspongins (236-243). The structures of sarains 1-3 (247-249) (2/0) and isosarain 1 (250) (211) were clarified on the basis of extensive spectroscopic analyses. The position of the double bond in 249 remains to be determined. The more polar fraction of this sponge contained three UV-absorbing alkaloids, named sarains A-C. The structure of the diacetylated derivative of sarain A (251) was established by X-ray analyis (2/2). 

Reniera sarai Pulitzeri-Finali Naples, Italy Bay of Naples 79 [61]... 

Mancini, Sicurelli, Guella, Turk, MaCek and Sepcic (2004) Fig. (35). Synthesis of oligomeric analogues of poly-APS (77) from Reniera sarai... 

Sarains, a new class of alkaloids from the sponge Reniera sarai. Cimino, G. De Stefano, S. Scognamiglio, G. and Trivellone, E. Bull. Soc. Chim. Belg. 1986, 95, 783. 

Further studies of alkaloids from Reniera sarai structures of saraine-3 and isosaraine-3 absolute stereochemistry of saraine-1 and sariane 2. Guo, Y. Madaio, A. Trivellone, E. Scognamiglio, G. and Cimino, G. Tetrahedron, 1996, 52, 14961. 

Unprecedented alkaloid from the mediterranean sponge Reniera sarai X-ray structure of an acetate derivative of Sarain-A. Cimino, G. Mattia, C. A. Mazzarella, L. Puliti, R. Scognamiglio, G. Spinella, A. and Trivellone, E. Tetrahedron 1989, 45, 3863. 

Unusual quinolizidine and piperidine alkaloids have been isolated from the Mediterranean sponge Reniera sarai (Haplosclerida, Dermospongiae) these compounds are probably related biosynthetically to "pet-rosin from Petmsia ficiformis. S. A, C32H50N2O3, Mr 510.38, amorphous powder, [aj -h66.0° (acetate in CHCI3). 

Sarain A (12) (Fig. 5) was isolated by Cimino et al. from the sponge Reniera sarai in 1989 [57] and has a unique 2,8-diazatricyclo[5.4.0.0 Mmidecane skeleton in which the tertiary amine of a pyrrolidine ring (ring B) interacts with an adjacent aldehyde. 

Structures equivalent to those described above, and generally called polymeric alkylpyridinium salts (PAPS), have been isolated from Reniera sarai harvested in the Adriatic Sea at depths of 15—40 m. These polymers have anticholinesterase, cytotoxic and hemolytic activities, but the oligomers of molar mass less than 3000 Da show no activity (Sepcic et al., 1997,1998 Malovrh et al., 1999 Brmc et al., 2000, 2002). 

Bunc, M., Sepdc, K., Turk, T, and Suput, D. (2000) In vivo effects of head-to-tad 3-alkylpyridinium polymers isolated from the marine sponge Reniera sarai. Pjlugers Arch. Eur. J. Physiol, 440 (Suppk), R173-R174... 

Cimino, G., Spinella, A., and Trivellone, E, (1989b) Isosarain-1 a new alkaloid from the Mediterranean sponge Reniera sarai. Tetrahedron Lett., 30, 133-136. 

Guo, Y.W., Madaio, A., Trivellone, E., Scognamiglio, G., and Cimino, G. (1996a) Structural and stereochemical studies of saraines macrocyclic alkaloids of the sponge Reniera sarai. Tetrahedron, 52, 8341-8348. 

Malovrh, P., Sepcic, K., Turk, T., and Macek, P. (1999) Characterization of hemolytic activity of 3-alkylpyridinium polymers from the marine sponge Reniera sarai. Comp. Biochem. Physiol, 124C, 221-226. 

Sepcic, K., Marcel, V., Klaebe, A., Turk, T, Suput, D., and Fournier, D. (1998) Inhibition of acetylcholinesterase by an alkylpyridinium polymer from the marine sponge, Reniera sarai. Biochim. Biophys. Acta, 1387, 217-225,... 

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