Guanidine alkaloid

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... 

Gramme 37, 113, 146, 175, 179 Graveoline 114 Guanidine alkaloids 57 Guanine derived alkaloids 49 Guaranine 43, 51 Guvacoline 86... 

Chemical bias toward certain molecular arrangements may also determine the commonness of certain metabolites (Pietra 1995), such as the aplysinopsins (indole alkaloids of many sponges, cnidarians, and mollusks. Chart 8.2. A), bis-indole and guanidine alkaloids (Chart 8.2.A), isoprenoids (Pietra 1995, Chart 8.2.1), and polypropionates of mollusks, sponges, and fungi (Chart 8.2.FA/PO). 

Macrolides from lithistid sponges and long-chain guanidine alkaloids (phloeodictyins) from nepheliospongid sponges are the most unusual metabolites from New Caledonian deep waters (Table 9.III). 

Coffey, D.S. McDonald, A.I. Overman, L.E. Rabinowitz, M.H. Renhowe, P.A. (2000) A practical artry to the crarabescidin family of guanidine alkaloids. Enantioselective total syntheses of ptilomycalin A, crambescidin 657 and its methyl ester, and crambescidin 800. J. Am. Chan. Soc., 122,4893-903. 

Kourany-Lefoll, E. Laprevote, O. Sevenet, T. Montagnac, A. Pais, M. Debitus, C. (1994) Phloeodictines A1-A7 and C1-C2, Antibiotic and Cytotoxic Guanidine Alkaloids from the New Caledonian Sponge, Phloeodictyon sp. Tetrahedron, 50,3415-26. 

Palagiano, E. De Marino, S. Minale, L. Riccio, R. Zollo, F. lorizzi, M. Carre, J.B. Debitus, C. Lucarain, L. Provost, J. (1995) Ptilomycalin A, crambescidin 800 and related new highly cytotoxic guanidine alkaloids from the starfishes Fromia monilis and Celerina heffemani. Tetrahedron, 51, 3675-82. 

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. 

Additional but simpler members of this class of guanidine alkaloids are the icthyotoxiccrambescins (formerly crambines) A (109), B (110), and Cl (111) isolated... 

The chemistry (isolation, structures, and synthesis) and biological activities of this large class of guanidine alkaloids have been the subject of several reviews [239-243]. 

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