Marine guanidine alkaloids

Marine sponges are recognized as the major source bioaetive guanidine alkaloids. Considering the number of the isolated compounds, only selected and illustrative examples have been included in this chapter to provide an overview of marine guanidine alkaloids. 

Marine sponges are a source of an array of polycyclic diamine alkaloids of common biogenetic origin. This class of secondary metabolites has been the subject of four previous reviews [4-7]. Therefore, the present review will include literature reports previously not discussed, dealing with the isolation, structure determination, biological activities, and total synthesis of polycycUc diamine alkaloids isolated from marine sponges. This review will not include guanidine alkaloids [8,9] or the manzamine alkaloids [10,11], since these compounds have been recently reviewed elsewhere. Only polycycUc... 

Owing to their intrinsic basicity, marine invertebrate guanidine alkaloids have a rather polar behavior and their isolation from complex mixtures may be difficult. Isolation procedures frequently include chromatography on lipophilic Sephadex LH20, on reversed phase silica gel (such as Cig bonded, aminopropyl bonded, or cyanopropyl bonded), or even on ion-exchange resins. HPLC purification using acidic (TFA) or buffered eluents have frequently been employed. 

Two new polycyclic guanidine alkaloids, cambrescidins 826 and dehydroaranobine A, were isolated from the marine sponge Monanchora spp. [61]. The pentacyclic guanidine alkaloids inhibit HIV-1 envelope-... 

Berlinck R. G. S., Braekman, J. C., Daloze, D., Bruno, I., Riccio, R., Ferri, S., Spampinato, S., and Speroni, E. (1993) Polycyclic guanidine alkaloids from the marine sponge Crambe crambe and Ca channel blocker activity of crambescidin 816. J Nat. Prod. 56, 1007-1015. 

The excellent reviews of Berlinck [1-5] have surveyed a great number of guanidine-type natural products. In addition, some guanidine-derived marine alkaloids have been reviewed by Kobayashi and Ishibashi [6,7]. Also, a recent book gave accounts of marine alkaloids including the phakellins, palau amines and oroidin-like dimers derived from bromopyrroles and polyketide-derived polycyclic guanidine alkaloids [8]. 

Kashman, Y, Hirsh, S., McConnell, O.J. et al. (1989) Ptilomycalin A a novel polycyclic guanidine alkaloid of marine origin. Journal of the American Chemical Society, 111, 8925-8926. 

Bensemhoun, J., Bombarda, I., Aknin, M. et al. (2007) Ptilomycalin D, a polycyclic guanidine alkaloid from the marine sponge Monanchora dianchora. Journal of Natural Products, 70, 2033-2035. 

Chang, L., Whittaker, N. F., and Bewley, C. A. (2003). Crambesddin 826 and dehydrocram-bine A new polycyclic guanidine alkaloids from the marine sponge Monanchora sp. that inhibit HIV-1 fusion. / Nat Prod 66,1490-1494. 

The dipolar H-H couplings have been applied by Chang et to establish the relative stereochemistry of two new polyclic guanidine alkaloids, crambes-cidin 826 and dehydrocrambine A isolated from the marine sponge Monanchora sp. 

Braekman, J.C., Daloze, D., Tavares, R., Hajdu, E., and Van Soest, R.W. M. (2000) Novel polycyclic guanidine alkaloids from two marine sponges of the genus Monanchora. J. Nat. Prod., 63,193-196. 

Guzii, A.G., Makarieva, T.N., Denisenko, V.A., Dmitrenok, P.S., Kuzmich, A.S., Dyshlovoy, S.A., Krasokhin, V.B., and Stonik, V.A. (2010) Monanchocidin A new apoptosis-inducing polycyclic guanidine alkaloid from the marine sponge Morumchora pulchra. Org. Lett., 12, 4292-4295. 

Laville, R., Thomas, O.P., Berrue, F., Marquez, D., Vacelet, (., and Amade, P. (2009c) Bioactive guanidine alkaloids from two Caribbean marine sponges./. Nat. Prod., 72, 1589-1594. 

Sorek, H., Rudi, A., Gueta, S., Reyes, F., Martin, M.J., Aknin, M., Gaydou, E., Vacelet, J., and Kashman, Y. (2006a) Netamines A-G seven new tricyclic guanidine alkaloids fiom the marine sponge Biemna laboutei. Tetrahedron, 62, 8838-8843. 

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