Monanchocidins B-E: polycyclic guanidine alkaloids with potent antileukemic activities from the sponge Monanchora pulchra.

New unusual polycyclic guanidine alkaloids monanchocidins B-E (2-5) along with monanchocidin A (1), which we recently described, were isolated from the Far-Eastern marine sponge Monanchora pulchra. Their structures were established using spectroscopic data and chemical transformations. Compounds 1-5 show potent cytotoxic activities against HL-60 human leukemia cells with IC50 values of 540, 200, 110, 830, and 650 nM, respectively.

[1]  A. Kuzmich,et al.  Monanchocidin: a new apoptosis-inducing polycyclic guanidine alkaloid from the marine sponge Monanchora pulchra. , 2010, Organic letters.

[2]  V. Stonik,et al.  STRONG ETHANOL SOLVATE OF DISCORHABDIN A ISOLATED FROM THE FAR-EAST SPONGE Latruculia oparinae , 2010, Chemistry of Natural Compounds.

[3]  O. Thomas,et al.  Bioactive guanidine alkaloids from two Caribbean marine sponges. , 2009, Journal of natural products.

[4]  A. Bode,et al.  Proapoptotic and Anticarcinogenic Activities of Leviusculoside G from the Starfish Henricia leviuscula and Probable Molecular Mechanism , 2008 .

[5]  E. Gaydou,et al.  Ptilomycalin D, a polycyclic guanidine alkaloid from the marine sponge Monanchora dianchora. , 2007, Journal of natural products.

[6]  R. Schinazi,et al.  Batzelladine alkaloids from the caribbean sponge Monanchora unguifera and the significant activities against HIV-1 and AIDS opportunistic infectious pathogens , 2007 .

[7]  F. Reyes,et al.  Netamines A–G: seven new tricyclic guanidine alkaloids from the marine sponge Biemna laboutei , 2006 .

[8]  M. H. Kossuga,et al.  Natural guanidine derivatives. , 2010, Natural product reports.

[9]  P. Scheuer,et al.  Alkaloids from the sponge Monanchora unguifera. , 2005, Journal of natural products.

[10]  M. Hamann,et al.  Crystallographic and NMR studies of antiinfective tricyclic guanidine alkaloids from the sponge Monanchora unguifera. , 2004, Bioorganic & medicinal chemistry.

[11]  C. Bewley,et al.  Crambescidin 826 and dehydrocrambine A: new polycyclic guanidine alkaloids from the marine sponge Monanchora sp. that inhibit HIV-1 fusion. , 2003, Journal of natural products.

[12]  V. Berdini,et al.  A modified palladium catalysed reductive amination procedure , 2002 .

[13]  J. Braekman,et al.  Novel polycyclic guanidine alkaloids from two marine sponges of the genus Monanchora. , 2000, Journal of natural products.

[14]  P. Murphy,et al.  The guanidine metabolites of Ptilocaulis spiculifer and related compounds; isolation and synthesis , 2000 .

[15]  D. Faulkner,et al.  Batzelladines F−I, Novel Alkaloids from the Sponge Batzella sp.: Inducers of p56lck-CD4 Dissociation , 1997 .

[16]  R. Riccio,et al.  Ptilomycalin A, crambescidin 800 and related new highly cytotoxic guanidine alkaloids from the starfishes Fromia monilis and Celerina heffernani , 1995 .

[17]  M. F. Bean,et al.  Novel Alkaloids from the Sponge Batzella sp.: Inhibitors of HIV gp120-Human CD4 Binding , 1995 .

[18]  J. Braekman,et al.  Isolation of crambescidin 800 from Monanchora arbuscula (Porifera) , 1994 .

[19]  K. Rinehart,et al.  On the structures of crambescins B and C1. , 1993, Journal of natural products.

[20]  R. Sakai,et al.  Polycyclic guanidine-containing compounds from the Mediterranean sponge Crambe crambe: the structure of 13,14,15-isocrambescidin 800 and the absolute stereochemistry of the pentacyclic guanidine moieties of the crambescidins , 1993 .

[21]  J. Braekman,et al.  Polycyclic guanidine alkaloids from the marine sponge Crambe crambe and Ca++ channel blocker activity of crambescidin 816. , 1993, Journal of natural products.

[22]  T. Kusumi,et al.  Structure and chemical properties of ptilomycalin A , 1992 .

[23]  J. Braekman,et al.  Crambines C1 and C2: Two Further Ichthyotoxic Guanidine Alkaloids from the Sponge Crambe crambe. , 1992, Journal of natural products.

[24]  J. G. Cory,et al.  5-(3-carboxymethoxyphenyl)-2-(4,5-dimethylthiazolyl)-3-(4-sulfophenyl)tetrazolium, inner salt (MTS) and related analogs of 3-(4,5-dimethylthiazolyl)-2,5-diphenyltetrazolium bromide (MTT) reducing to purple water-soluble formazans As cell-viability indicators , 1991 .

[25]  N. Burres,et al.  Isobatzellines A, B, C, and D. Cytotoxic and antifungal pyrroloquinoline alkaloids from the marine sponge Batzella sp , 1990 .

[26]  T. Kusumi,et al.  Ptilomycalin A: a novel polycyclic guanidine alkaloid of marine origin , 1989 .