Stylissa carteri

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]. 

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... 

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). 

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... 

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. 

Stevensine (= odiline) (23) has been isolated by Faulkner et al. from an unidentified marine sponge [26] and subsequently found in Pseudaxynissa cantharella [27], Axinella verrucosa [16], and in Stylissa carteri [28] along with 2-Debromostevensine (24). 

Linington, R. G., Williams, D. E., Tahir, A., Van Soest, R. W., Andersen, R. J., (2003). Latonduines A and B, new alkaloids isolated from the marine sponge Stylissa carteri Structure elucidation, synthesis, and biogenetic implications. Org. Lett. 5,2735-2738. 

In the vicinity of Hanish Islands, hence their names. This species is now called Stylissa carteri. 

Among the more complex structures, carteramine A and stylissadines A and B are respectively dimers (C22N10) and tetramers (C44N20) of C11N5 pyrrole-imidazole alkaloids. Isolated from the species Stylissa carteri harvested in Japan, carteramine A is an inhibitor of neutrophil chemotaxis (IC50 5 pM), and may lead to a new generation of anti-... 

Lastly, styhssazoles A-C are new complex pyrrole-2-aminoimidazole alkaloids (P-2-AI) that were isolated from Stylissa carteri collected in the Solomon Islands (Patel et al, 2010). These findings confirm the proposed universal biosynthetic pathway for all currently known dimeric P-2-AI compotmds (Al-Mourabit and Potier, 2001 Kock et al, 2007). 

Patel, K., Laville, R., Martin, M.-T., Tilvi, S., Moriou, C., Gallard, J.-F., Ermolenko, L., Debitus, C., and Al-Mourabit, A. (2010) Unprecedented stylissazoles A-C from Stylissa carteri Another dimension for marine pyrrole-2-aminoimidazole metabolite diversity. Angew. Chem. Int. Ed., 49, 4775-4779. 

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