Sponges manzamine alkaloids

Manzamine alkaloids ((3-carboline derivatives from sponges), syntheses and synthetic approaches 98T6201. 

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... 

Manzamine alkaloids can be isolated from marine sponges. They often contain /3-carboline. This group has a diverse range of bioactivities. It also has its own way of establishing its structures. An intramolecular Diels-Adler reaction for manzamines has been proposed. The a is bisdihydropyridine (derived probably from amonia), and the (3 is intramolecular cycloaddition in a pentacyclic... 

Fused tetracyclic and pentacyclic alkaloids constitute a relatively new class of natural products isolated mostly from ascidians and sponges. Cytotoxic, antimicrobial and antiviral activities have been reported for many of these compounds. The manzamine alkaloids, Fig. (33) are characterized by a complex pentacyclic diamine linked to C-l of P-carboline moiety. Manzamine have been isolated mainly from six different genera of marine sponges Haliclona, Pellina, Xestospongia, Ircinia, Pachypellin and Amphimedon. 

For the structurally more complex molecule 18, only the Schrock conditions worked. Compound 18 has been synthesized as a synthetic precursor of the marine alkaloid nakado-marin A (19 [14]) from the marine sponge Amphimedon sp. Nakadomarin A (19) belongs to the manzamine alkaloids, which are also targets of biomimetic syntheses [15], For both strategies, there is still some distance to go. 

In a continued search for new manzamine alkaloids, 1,2,3,4-tetrahydromanza-mine B (35) and ma eganedin A (36) has been isolated from the same species of the Okinawan marine sponge Amphimedon sp. [45,51]. Ma eganedin A has a unique methylene carbon bridge between N-2 and N-27. Their stmctures, including the absolute configuration, were elucidated from spectroscopic data. 

The manzamine alkaloids are characterized by a complex pentacyclic diamine linked to C-l of a B-carboline moiety. The first B-carboline compound (norharman and harman) was reported from a bioluminiscent marine dino-flagellate Noctiluca miliaris [31], followed by the discovery of the eudistomins from Eudistoma olivaceum [32, 33, 34], Their occurrence has been reported not only from sponges and tunicates, but also from the Bryozoan Costaticella hastata [35], and Cribricellina cribraria [36] and lately from the Cnidaria (Villagorgia rubra) exemplified by the Villagorgins [37]. 

ABSTRACT Marine sponges have frequently afforded a wide variety of alkaloids. Polycyclic amines (3-alkylpiperidine alkaloids) are secondary metabolites that are profusely found in Indo-Pacific sponges. These compounds contain complicated skeletons with several macrocyclic rings. One of the first members of these exclusively sponge-derived alkaloids is manzamine A, which was described independently by Riga in 1986 and by Nakamura in 1987. This compound possesses an unusual pentacyclic diamine fused ring joined to Cl of a )S-carboline moiety. 

Pentacyclic manzamine alkaloids from marine sponges... 

Ircinals A and B from the Okinawan Marine Sponge Ircinia sp. Plausible Biogenetic Precursors of Manzamine Alkaloids. Kondo, K. Shigemori, H. Kikuchi, Y. Ishibashi, M. Sasaki, T. and Kobayashi, J. J. Org. Chem. 1992, 57, 2480. 

New manzamine alkaloids from a sponge of the genus Xestospongia. Ichiba, T. Sakai, R. Kohmoto, S. and Saucy, G. Tetrahedron Lett. 1988, 29, 3083. 

Keramaphidin B, a Novel Pentacyclic Alkaloid from a Marine sponge Amphimedon sp. A Plausible Biogenetic Precursor of Manzamine Alkaloids. Kobayashi, J. Tsuda, M. Kawasaki, N. Matsumoto, K. and Adachi, T. Tetrahedron Lett. 1994, 35, 4383. 

Takahashi Y, Kubota T, Fremont J, Kobayashi J (2009) Zamamidines A and B, new manzamine alkaloids frran the sponge Amphimedon species. Org Lett 11 21-24... 

Rao KV, Kasanah N, Wahyuono S, Tekwani BL, Schinazi RF, Hamann MT (2004) Three manzamine alkaloids from a common Indonesian sponge and their activity against infectious and tropical parasitic diseases. J Nat Prod 67 1314-1318... 

Yousaf M, Hammond NL, Peng J, Wahyuono S, McIntosh KA, Charman WN, Mayer AMS, Hamann MT (2004) New manzamine alkaloids from an Indo-Pacific sponge. Pharmacokinetics, oral availability, and the significant activity of several manzamines against HTV-l, AIDS opportunistic infections, and infiammatory diseases. J Med Chem 47 3512-3517... 

Zhou B, Slebodnick C, Johnson RK, Mattem MR, Kingston DGI (2000) New cytotoxic manzamine alkaloids from aPalaun sponge. Tetrahedron 56 5781-5784... 

Rao KV, Santarsiero BD, Mesecar AD, Schinazi RF, Tekwani BL, Hamann MT. New manzamine alkaloids with activity against infectious and tropical parasitic diseases from an Indonesian sponge. J Nat Prod 2003 66(6) 823—8. 

Together with eudistomins, also manzamine alkaloids have received special attention due to their biological activities [2]. Manzamine alkaloids, mostly isolated from sponges, are characterized by a unique polycyclic ring system, which may biogenetically derive from ammonia, Cio and C3 units, and tryptamine [307]. In the majority of the manzamine alkaloids, the multicyclic units are condensed with tryptamine to form P-carboline. The first representative of this class of alkaloids, manzamine A (71), was isolated as hydrochloride salt from an Okinawan sponge ETfl/zc/oun sp. [308]. 

Kaiser, A., Billot, X., Gateau-Olesker, A., Marazano, C., and Das, B,C, (1998) Selective entry to the dimeric or oligomeric pyridinium sponge macrocydes via aminopentadienal derivatives. Possible biogenetic relevance with manzamine alkaloids. /. Am. Chem. Soc., 120, 8026-8034. 

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