Stylissa

Hymenialdisine (171) from the Indonesian sponge Stylissa carteri is cytotoxic to human monocytic leukemia cells (MONO-MAC 6) with an IC50 value of 0.2 pg/ml, whereas debromohymenialdisine is an order of magnitude less active (IC5o 2.4 pg/ml) [132]. 

An Australian sponge Axinella sp. has afforded the novel axinellamines A-D (1310-1313), which exhibit activity against Helicobacter pylori (1301). The similar massadine (1314) from the Japanese sponge Stylissa aff. massa inhibits geranylger-anyltransferase type I and the fungus Candida albicans (1302). Like many of these 2-aminoimidazole alkaloids, 1310-1314 were isolated as acid salts trifluoroacetic acid salts in these cases. 

Grube A, Lichte E, Kock M (2006) Isolation and Synthesis of 4-Bromopyrrole-2-carboxy-arginine and 4-Bromopyrrole-2-carboxy-fV(e)-lysine from the Marine Sponge Stylissa caribica. J Nat Prod 69 125... 

Eder C, Proksch P, Wray V, Steube K, Bringmann G, van Soest RWM, Sudarsono, Ferdinandus E, Pattisina LA, Wiryowidagdo S, Moka W (1999) New Alkaloids from the Indopacific Sponge Stylissa carteri. J Nat Prod 62 184... 

Linington RG, Williams DE, Tahir A, van Soest R, Andersen RJ (2003) Latonduines A and B, New Alkaloids Isolated from the Marine Sponge Stylissa carteri Structure Elucidation, Synthesis, and Biogenetic Implications. Org Lett 5 2735... 

Assmann M, van Soest RWM, Kock M (2001) New Antifeedant Bromopyrrole Alkaloid from the Caribbean Sponge Stylissa caribica. J Nat Prod 64 1345... 

Nishimura S, Matsunaga S, Shibazaki M, Suzuki K, Furihata K, van Soest RWM, Fusetani N (2003) Massadine, a Novel Geranylgeranyltransferase Type I Inhibitor from the Marine Sponge Stylissa aff. massa. Org Lett 5 2255... 

Hymenialdesine (alkaloid) Stylissa massa (Philippine sponge) MAPKK-1 (= MEK-1) (3 nM)... 

A 2-debrominated hymenin (25) has been isolated from the sponge Stylissa (= Axindla) carteri [49]. A series of alkaloids of the hymenin family differ from this parent compound only in the number and/or the position of the double bonds. Stevensine (= odiline) (26) was isolated by Faulkner et al. from an unidentified marine... 

These molecules, initially called yellow compounds, have been isolated from Phakdlia jlabdlata [53], Axindla verrucosa [54], Acanthella aurantiaca [54], Hymeniacidon aldis [55], Stylissa carteri [49], and Pseudaxynissa canthardla [51[. The observation that, in solvents such as DMSO, ( )-hymenialdisins slow ly converted into their corresponding (Z)-isomers, as show n below , provided a reasonable explanation for the finding of both geometrical isomers in the hymenialdisin series (Scheme 10.1). 

It should be noted that cyclooroidin (38) could be envisaged as the precursor of the nonimidazole bromopyrrole alkaloids longamides (see below). Two cyclooroidin analogs have been isolated agesamide (39) from Agelas sp. [68] and oxocyclostylidol (40) from Stylissa caribica [69]. This latter compound represents the first pyrrole-imidazole alkaloid that includes an oxidized pyrrole moiety. 

The first examples of tetrameric pyrrole imidazole alkaloids, stylissadine A (100) and B, were isolated from the Caribbean sponge Stylissa carihica in 2006 [128]. They possess a symmetric dimeric stmcture derived from condensation of two massadine units, and differ in the configuration at the center C-2. Stylissadines represent the largest pyrrole-imidazole alkaloids isolated so far, and, with their 16 stereogenic centers, they are the most complex stmctures known within the oroidin alkaloid family. 

Latonduines A (137) and B (138), have been isolated from the Indonesian sponge Stylissa carteri [163]. Their skeleton caimot be derived from the C Ns building block of the oroidins it has been proposed that ornithine is the biogenetic precursor to the aminopyrimidine fragment of the latonduines. Agelasine G (139), a new... 

Grube and Kock [47] reported the characterization of oxocyclostylidol (12), an intramolecular cyclized oroidin derivative from the marine sponge, Stylissa caribica. 

Kobayashi, H., Kitamura, K., Nagai, K. et al. (2007) Carteramine A, an inhibitor of neutrophil chemotaxis, from the marine sponge Stylissa carteri. Tetrahedron Letters, 48, 2127-2129. 

Tasdemir D, Mallon R, Greenstein M, Feldberg LR, Kim SC, Collins K, et al. Aldi-sine alkaloids from PhUlippine sponge Stylissa massa are potent inhibitors of nitrogen-activated protein kinase-1 (MEK-1). J Med Chem 2002 45(2) 529-32. 

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