Two new steroidal alkaloids 3o~-amino-23,29-imino-B(9a)-homo-19-nor-5ot-stigmasta-1(10),7,9(11),2... more Two new steroidal alkaloids 3o~-amino-23,29-imino-B(9a)-homo-19-nor-5ot-stigmasta-1(10),7,9(11),23(N)-tetraene (1) and 3o~-amino-23,29-imino-B(9a)-homo-19-nor-5ot-stigmastal(10),7,23(N)-triene (2) have been isolated from a Pacific marine sponge Corticium sp. The structures of compounds 1 and 2 were defined by spectral methods and mainly 1D and 2D NMR experiments.
Several studies on the chemical constituents of Celastraceae plants have revealed the presence of... more Several studies on the chemical constituents of Celastraceae plants have revealed the presence of various b-dihydroagarofuran sesquiterpene polyol esters [1], [2], [3], [4]. In previous literature, seed extracts from Celastrus paniculatus have been reported to have significant beneficial effects on intestinal complaints, such as intestinal spasms, supporting their use as a traditional remedy for intestinal disturbances [5]. For this reason in a previous study we have evaluated the possible relaxant effect of C. paniculatus in vitro on isolated ileum [6]
Four new jaspamide derivatives with antimicrofilament activity were isolated from the marine spon... more Four new jaspamide derivatives with antimicrofilament activity were isolated from the marine sponge Jaspis splendans. Their structures were elucidated by NMR and MS analysis. A structure-activity relationship analysis on all natural jaspamides is also reported here.
Continued investigation of cytotoxic extracts of the marine sponge Jaspis splendans has resulted ... more Continued investigation of cytotoxic extracts of the marine sponge Jaspis splendans has resulted in the discovery of jaspamides H-L (2-5). Their structures were determined by interpretation of their NMR and ESIMS data. All compounds exhibited potent cytotoxic activities and were shown to cause microfilament disruption. Biological activity and structural elucidation are reported here.
Four new jaspamide derivatives with antimicrofilament activity were isolated from the marine spon... more Four new jaspamide derivatives with antimicrofilament activity were isolated from the marine sponge Jaspis splendans. Their structures were elucidated by NMR and MS analysis. A structure-activity relationship analysis on all natural jaspamides is also reported here.
... Jaspamide D (4) was obtained as a white amorphous solid and its molecular formula was establi... more ... Jaspamide D (4) was obtained as a white amorphous solid and its molecular formula was established by HRESIMS as C 37 H 47 BrN 4 O 6 . Compared with the molecularformula of 1, there was the gain of one CH 2 group. ...
This paper covers recent work -much of it from the author's laboratory -dealing with novel steroi... more This paper covers recent work -much of it from the author's laboratory -dealing with novel steroidal oligoglycosides from starfishes. The steroidal glycosides until now encountered in this class of marine animals can be grouped into three structure types. Compounds of the first type, recognized for long time, include the sulphated saponins (asterosaponins) , characterized by steroidal aglycones possessing a 3,6ct-diol pattern and a 9,11-double bond; the oligosaccharide moiety (four up to six sugar units) is attached at C-6 and the sulphate residue is at C-3. Compounds of the second type, recently discovered in two species of the genus Echinaster, have a number of unusual features: a L7,3,613-dihydroxy steroidal moiety, there is no sulphate group and, most remarkably, the carbohydrate chain (three sugar units) is cyclized between C-3 and C-6 of the aglycone. Compounds of the third type include glycosides having highly hydroxylated steroidal aglycones; the carbohydrate moiety (one or two sugar units) is attached at C-24 of the side chain and there is no sulphate residue. During the course of our investigation on the steroidal glycosides from starfishes we have also encountered several polyhydroxylated sterols and their structures are presented.
Two diglucoside stilbene trimers and a benzoisofuranone derivative were isolated from Foeniculum ... more Two diglucoside stilbene trimers and a benzoisofuranone derivative were isolated from Foeniculum vulgare fruit together with nine known compounds. Their structures were elucidated by spectral methods including 1D, 2D NMR and MS and chemical methods. Antioxidant activity was tested using three methods: DPPH Å , total antioxidant capacity and assay of lipid peroxidation.
Dragon's blood (Sangre de drago), a viscous red sap derived from Croton lechleri Muell-Arg (Eupho... more Dragon's blood (Sangre de drago), a viscous red sap derived from Croton lechleri Muell-Arg (Euphorbiaceae), is extensively used by indigenous cultures of the Amazonian basin for its wound healing properties. The aim of this study was to identify the minor secondary metabolites and test the antioxidant activity of this sustance. A bioguided fractionation of the n-hexane, chloroform, n-butanol, and aqueous extracts led to the isolation of 15 compounds: three megastigmanes, four flavan-3-ols, three phenylpropanoids, three lignans, a clerodane, and the alkaloid taspine. In addition to these known molecules, six compounds were isolated and identified for the first time in the latex: blumenol B, blumenol C, 4,5-dihydroblumenol A, erythro-guaiacyl-glyceryl-β-O-4'dihydroconiferyl ether, 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-propane-1,3-diol and floribundic acid glucoside. Combinations of spectroscopic methods ( 1 H-, 13 C-NMR and 2D-NMR experiments), ESI-MS, and literature comparisons were used for compound OPEN ACCESS Molecules 2008, 13 1220
Two new steroidal alkaloids 3o~-amino-23,29-imino-B(9a)-homo-19-nor-5ot-stigmasta-1(10),7,9(11),2... more Two new steroidal alkaloids 3o~-amino-23,29-imino-B(9a)-homo-19-nor-5ot-stigmasta-1(10),7,9(11),23(N)-tetraene (1) and 3o~-amino-23,29-imino-B(9a)-homo-19-nor-5ot-stigmastal(10),7,23(N)-triene (2) have been isolated from a Pacific marine sponge Corticium sp. The structures of compounds 1 and 2 were defined by spectral methods and mainly 1D and 2D NMR experiments.
Several studies on the chemical constituents of Celastraceae plants have revealed the presence of... more Several studies on the chemical constituents of Celastraceae plants have revealed the presence of various b-dihydroagarofuran sesquiterpene polyol esters [1], [2], [3], [4]. In previous literature, seed extracts from Celastrus paniculatus have been reported to have significant beneficial effects on intestinal complaints, such as intestinal spasms, supporting their use as a traditional remedy for intestinal disturbances [5]. For this reason in a previous study we have evaluated the possible relaxant effect of C. paniculatus in vitro on isolated ileum [6]
Four new jaspamide derivatives with antimicrofilament activity were isolated from the marine spon... more Four new jaspamide derivatives with antimicrofilament activity were isolated from the marine sponge Jaspis splendans. Their structures were elucidated by NMR and MS analysis. A structure-activity relationship analysis on all natural jaspamides is also reported here.
Continued investigation of cytotoxic extracts of the marine sponge Jaspis splendans has resulted ... more Continued investigation of cytotoxic extracts of the marine sponge Jaspis splendans has resulted in the discovery of jaspamides H-L (2-5). Their structures were determined by interpretation of their NMR and ESIMS data. All compounds exhibited potent cytotoxic activities and were shown to cause microfilament disruption. Biological activity and structural elucidation are reported here.
Four new jaspamide derivatives with antimicrofilament activity were isolated from the marine spon... more Four new jaspamide derivatives with antimicrofilament activity were isolated from the marine sponge Jaspis splendans. Their structures were elucidated by NMR and MS analysis. A structure-activity relationship analysis on all natural jaspamides is also reported here.
... Jaspamide D (4) was obtained as a white amorphous solid and its molecular formula was establi... more ... Jaspamide D (4) was obtained as a white amorphous solid and its molecular formula was established by HRESIMS as C 37 H 47 BrN 4 O 6 . Compared with the molecularformula of 1, there was the gain of one CH 2 group. ...
This paper covers recent work -much of it from the author's laboratory -dealing with novel steroi... more This paper covers recent work -much of it from the author's laboratory -dealing with novel steroidal oligoglycosides from starfishes. The steroidal glycosides until now encountered in this class of marine animals can be grouped into three structure types. Compounds of the first type, recognized for long time, include the sulphated saponins (asterosaponins) , characterized by steroidal aglycones possessing a 3,6ct-diol pattern and a 9,11-double bond; the oligosaccharide moiety (four up to six sugar units) is attached at C-6 and the sulphate residue is at C-3. Compounds of the second type, recently discovered in two species of the genus Echinaster, have a number of unusual features: a L7,3,613-dihydroxy steroidal moiety, there is no sulphate group and, most remarkably, the carbohydrate chain (three sugar units) is cyclized between C-3 and C-6 of the aglycone. Compounds of the third type include glycosides having highly hydroxylated steroidal aglycones; the carbohydrate moiety (one or two sugar units) is attached at C-24 of the side chain and there is no sulphate residue. During the course of our investigation on the steroidal glycosides from starfishes we have also encountered several polyhydroxylated sterols and their structures are presented.
Two diglucoside stilbene trimers and a benzoisofuranone derivative were isolated from Foeniculum ... more Two diglucoside stilbene trimers and a benzoisofuranone derivative were isolated from Foeniculum vulgare fruit together with nine known compounds. Their structures were elucidated by spectral methods including 1D, 2D NMR and MS and chemical methods. Antioxidant activity was tested using three methods: DPPH Å , total antioxidant capacity and assay of lipid peroxidation.
Dragon's blood (Sangre de drago), a viscous red sap derived from Croton lechleri Muell-Arg (Eupho... more Dragon's blood (Sangre de drago), a viscous red sap derived from Croton lechleri Muell-Arg (Euphorbiaceae), is extensively used by indigenous cultures of the Amazonian basin for its wound healing properties. The aim of this study was to identify the minor secondary metabolites and test the antioxidant activity of this sustance. A bioguided fractionation of the n-hexane, chloroform, n-butanol, and aqueous extracts led to the isolation of 15 compounds: three megastigmanes, four flavan-3-ols, three phenylpropanoids, three lignans, a clerodane, and the alkaloid taspine. In addition to these known molecules, six compounds were isolated and identified for the first time in the latex: blumenol B, blumenol C, 4,5-dihydroblumenol A, erythro-guaiacyl-glyceryl-β-O-4'dihydroconiferyl ether, 2-[4-(3-hydroxypropyl)-2-methoxyphenoxy]-propane-1,3-diol and floribundic acid glucoside. Combinations of spectroscopic methods ( 1 H-, 13 C-NMR and 2D-NMR experiments), ESI-MS, and literature comparisons were used for compound OPEN ACCESS Molecules 2008, 13 1220
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