J. Luis Carballo

New cytotoxic metabolites from the sponge Mycale micracanthoxea

Abstract The sponge Mycale microanthoxea contains fourteen new compounds: a series of twelve 5-acyl-2-hydroxymethylpyrroles, named mycalazols 1-12 ( 1-12 ), together with two 5-alkylpyrrole-2-carbaldehydes, mycalazal 1 ( 13 ) and mycalazal 2 ( 14 ). The structures were elucidated by interpretation of spectral data. In general ,the new compounds showed significant in vitro cytotoxicity.

Sesquiterpenes from the Sponge Axinyssa isabela

Further research on the constituents of the sponge Axinyssa isabela collected in the Gulf of California has led to the isolation of nine new sesquiterpenes, the eudesmanes axinisothiocyanates M and N (1, 2), the bisabolane axinythiocyanate A (3), and the aristolane derivatives axinysones A-E (4-8) and axinynitrile A (9), together with four known sesquiterpenoids (10-13). The structures of the new metabolites have been established by spectroscopic techniques.The absolute configuration of axinysones A (4) and B (5) has been assigned after esterification with (R)- and (S)-MPA acids. In addition, the unusual nitrile-containing sesquiterpene 9 has been synthesized from (+)-aristolone (14). The cytotoxic activity of the compounds isolated has been tested against three human tumor cell lines.

Isothiocyanate Sesquiterpenes from a Sponge of the Genus Axinyssa

The chemical study of a sponge of the genus Axinyssa collected in the Gulf of California has led to the isolation of the new bicyclic sesquiterpenes axinisothiocyanates A-L ( 1- 12) together with the known compounds (1 R,6 S,7 S,10 S)-10-isothiocyanato-4-amorphene ( 13), (4 R*,5 R*,7 S*,10 R*)-4-isocyanoeudesm-11-ene, (-)-epipolasin A, and (+)-aristolone. The structures of the new metabolites have been established by spectroscopic techniques, including the analysis of pyridine-induced 1H NMR chemical shifts. The cytotoxic activity has been tested against three human tumor cell lines.

Muricenones A and B: New Degraded Pregnanes From a Gorgonian of the Genus Muricea

The gorgonian Muricea sp. contains two new degraded pregnanes, muricenones A (1) and B (2), whose structures have been defined by spectroscopic analysis. The uncommon carbon framework of muricenones may be biosynthetically derived by oxidative cleavage and loss of one carbon atom of the A-ring of the steroidal nucleus. The new compounds, 1 and 2, isolated from Muricea sp., selectively inhibit the growth of the A-549 human lung carcinoma cell line. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

Cembrane Diterpenes from the Gorgonian Leptogorgia laxa

The new cembrane diterpenes leptodienone A (2) and leptodienone B (3) and the known compounds lopholide, lophodiol B, lophodione, and lophotoxin (1) have been isolated from the gorgonian Leptogorgia laxa collected in the Gulf of California. The structures of the new metabolites have been established by spectroscopic techniques. The in vitro cytotoxicity of the new compounds has been tested against three human tumor cell lines.

Sesquiterpene hydroquinones from the sponge Reniera mucosa

Abstract The sponge Reniera mucosa contains eight new compounds, six of them of the panicein class (1-6) and two novel cyclohexenones renierin A (7) and renierin B(8), together with seven related known compounds (9-15). Cyclohexenones 7 and 8 might be the biosynthetic intermediates from farnesyl precursors to paniceins. The structures were elucidated by interpretation of spectral data and chemical interconversions. Four of the new compounds (2, 3, 4 and 6) showed significant in vitro cytotoxicity.