RESUMEN
Bioassay-directed fractionation of an extract of the root and bark of Podocarpus madagascariensis resulted in the isolation of a new totarol diterpenoid (1) in addition to the three known cytotoxic diterpenoids 19-hydroxytotarol (2), totaradiol (3), and 4beta-carboxy-19-nor-totarol (4). The structure of the new compound 1 was established as methyl-13-hydroxy-14-isopropyl-9(11),12,14(8)-podocarpatriene-19-oate on the basis of 1D and 2D NMR spectroscopic interpretation and methylation of 4. All the compounds exhibited cytotoxic activity against the A2780 ovarian cancer cell line.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Cycadopsida/química , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Antineoplásicos Fitogénicos/química , Línea Celular Tumoral , Diterpenos/química , Ecosistema , Femenino , Humanos , Madagascar , Resonancia Magnética Nuclear Biomolecular , Neoplasias Ováricas/tratamiento farmacológico , Corteza de la Planta/química , Raíces de Plantas/química , Espectrometría de Masa Bombardeada por Átomos Veloces , Espectrofotometría Infrarroja , Espectrofotometría UltravioletaRESUMEN
Bioassay-directed fractionation of ethanol extracts of the roots and leaves of the plant Cassipourea madagascariensis resulted in the isolation of the two new terpenoids cassipourol (1) and cassipouryl acetate (2) in addition to the three known compounds, 3beta,30-dihydroxylup-20(29)-ene (3), 30-hydroxylup-20(29)-en-3-one (4), and combretol (5). The structures of the two new compounds were established on the basis of 1D and 2D NMR spectroscopic data and chemical conversion. All the isolated compounds were tested against the A2780 human ovarian cancer cell line; the two diterpenes (1 and 2) showed moderate cytotoxic activity, while the three known compounds (3-5) were weakly active.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Plantas Medicinales/química , Rhizophoraceae/química , Antineoplásicos Fitogénicos/química , Diterpenos/química , Ensayos de Selección de Medicamentos Antitumorales , Femenino , Humanos , Madagascar , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Hojas de la Planta , Células Tumorales CultivadasRESUMEN
Bioassay-guided fractionation of an EtOAc extract of the leaves of Melampodium camphoratum using an assay for inhibitors of the degradation of hemin resulted in the isolation of six new eudesmane sesquiterpenes (1-6) and the known 6-epi-beta-verbesinol coumarate (7). The structures of compounds 1-6 were established as 6alpha-(4'-O-methyl-7'E-coumaryloxy)eudesm-4(14)-ene (1), 6alpha-({4'-O-stearyl}-7'E-coumaryloxy)eudesm-4(14)-ene (2), 6alpha-({4'-O-palmityl}-7'E-coumaryloxy)eudesm-4(14)-ene (3), 6alpha-({4'-O-[9' 'Z-hexadecenoyl]}-7'E-coumaryloxy)eudesm-4(14)-ene (4), 6alpha-(7'Z-coumaryloxy)eudesm-4(14)-ene (5), and 6alpha-({4'-acetoxy}-7'Z-coumaryloxy)eudesm-4(14)-ene (6). Compounds 1-4 showed weak activity in the hemin degradation assay, while compounds 5-7 were inactive.
Asunto(s)
Antimaláricos/aislamiento & purificación , Asteraceae/química , Hemina/metabolismo , Plantas Medicinales/química , Sesquiterpenos de Eudesmano/aislamiento & purificación , Animales , Antimaláricos/química , Antimaláricos/farmacología , Concentración 50 Inhibidora , Estructura Molecular , Hojas de la Planta/química , Plasmodium falciparum/efectos de los fármacos , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacología , Estereoisomerismo , SurinameRESUMEN
Bioassay-directed fractionation of a methyl ethyl ketone extract of Solidago canadensis L. (Asteraceae), using an assay to detect the lyase activity of DNA polymerase beta, resulted in the isolation of the four new lupane triterpenoids 1-4 and the seven known compounds lupeol, lupeyl acetate, ursolic acid, cycloartenol, cycloartenyl palmitate, alpha-amyrin acetate, and stigmasterol. The structures of the new compounds were established as 3beta-(3R-acetoxyhexadecanoyloxy)-lup-20(29)-ene (1), 3beta-(3-ketohexadecanoyloxy)-lup-20(29)-ene (2), 3beta-(3R-acetoxyhexadecanoyloxy)-29-nor-lupan-20-one (3), and 3beta-(3-hetohexadecanoyloxy)-29-nor-lupan-20-one (4), respectively, on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical modification studies. All 11 compounds were inhibitory to the lyase activity of DNA polymerase beta.
Asunto(s)
ADN Polimerasa beta/antagonistas & inhibidores , Inhibidores Enzimáticos/síntesis química , Solidago/química , Triterpenos/síntesis química , Inhibidores Enzimáticos/farmacología , Concentración 50 Inhibidora , Liasas/antagonistas & inhibidores , Resonancia Magnética Nuclear Biomolecular , Extractos Vegetales , Relación Estructura-Actividad , Triterpenos/farmacologíaRESUMEN
Continuation of the chemical examination of the cytotoxic constituents of the wood of Vepris punctata resulted in the isolation of the two new terpenoids 1 and 2 and eight known compounds, glechomanolide (3), isogermafurenolide, (E,E)-germacra-1(10),4,7(11)-triene, alpha-amyrin, lupeol, lupeyl acetate, taraxerol, and 3-epi-taraxerol, in addition to the alkaloids reported reported previously. The structures of the two new compounds were established on the basis of 1D and 2D NMR spectroscopic data interpretation and chemical modifications. All the isolated compounds were tested against the A2780 human ovarian cancer cell line; the four sequiterpenoids showed moderate cytotoxic activity, while the six triterpenoids were inactive.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Plantas Medicinales/química , Rutaceae/química , Terpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Femenino , Humanos , Hidrólisis , Madagascar , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Estereoisomerismo , Relación Estructura-Actividad , Terpenos/química , Terpenos/farmacología , Células Tumorales Cultivadas , MaderaRESUMEN
Bioassay-directed fractionation of a butanone extract of Monochaetum vulcanicum resulted in the isolation of a new triterpene (1) and four known compounds, ursolic acid (2), 2alpha-hydroxyursolic acid (3), 3-(p-coumaroyl)ursolic acid (4), and beta-sitosteryl-beta-d-galactoside (5). The structure of the new compound 1 was established as 3beta-acetoxy-2alpha-hydroxyurs-12-en-28-oic acid on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical derivatization. Compounds 1-3 and 5 exhibited polymerase beta lyase activity.
Asunto(s)
ADN Polimerasa beta/antagonistas & inhibidores , Inhibidores Enzimáticos/aislamiento & purificación , Liasas/antagonistas & inhibidores , Melastomataceae/química , Plantas Medicinales/química , Triterpenos/aislamiento & purificación , Acetilación , Costa Rica , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/farmacología , Concentración 50 Inhibidora , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Estereoisomerismo , Triterpenos/química , Triterpenos/farmacología , Ácido UrsólicoRESUMEN
Bioassay-guided fractionation of an ethanolic extract of the infructescences of Polyscias amplifolia resulted in the isolation of two new oleanolic acid saponins, polyfoliolides A (1) and B (2), in addition to the two known saponins 3-O-beta-D-galactopyranosyloleanolic acid (3) and 3-O-beta-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyloleanolic acid (4). The structures of the two new compounds were established as 3-O-beta- D-galactopyranosyl-(1-->4)-beta-D-xylopyranosyloleanolic acid (1) and 3-O-beta-D-galactopyranosyl-(1-->4)-alpha-L-arabinopyranosyloleanolic acid (2) on the basis of extensive 1D and 2D NMR spectroscopic data interpretation and chemical conversions. All the isolated compounds showed weak cytotoxicity against A2780 human ovarian cancer cell line, with IC50 values in the range 6.7 to 10.8 microg/mL.
Asunto(s)
Antineoplásicos/farmacología , Araliaceae , Fitoterapia , Extractos Vegetales/farmacología , Saponinas/farmacología , Antineoplásicos/administración & dosificación , Antineoplásicos/química , Antineoplásicos/uso terapéutico , Femenino , Humanos , Concentración 50 Inhibidora , Madagascar , Medicina Tradicional , Neoplasias Ováricas/tratamiento farmacológico , Extractos Vegetales/administración & dosificación , Extractos Vegetales/química , Extractos Vegetales/uso terapéutico , Saponinas/administración & dosificación , Saponinas/química , Saponinas/uso terapéutico , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Bioassay-directed fractionation of a CH(2)Cl(2)-MeOH extract of the leaves of Oncostemon bojerianum resulted in the isolation of eight new 5-alkylresorcinols, named oncostemonols A-H (1-8), and two known derivatives, (8'Z)-1,3-dihydroxy-5-[16'-(3' ',5' '-dihydroxyphenyl)-8'-hexadecen-1'-yl]benzene (9) and (8'Z)-1,3-dihydroxy-5-[14'-(3' ',5' '-dihydroxyphenyl)-8'-tetradecen-1'-yl]benzene (10). The structures of the new compounds 1-8 were elucidated on the basis of extensive 1D and 2D NMR spectroscopic interpretation and chemical derivatization. All the compounds exhibited cytotoxic activity against the A2780 ovarian cancer cell line.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Plantas Medicinales/química , Primulaceae/química , Resorcinoles/aislamiento & purificación , Acetilación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Femenino , Humanos , Concentración 50 Inhibidora , Madagascar , Metilación , Conformación Molecular , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Neoplasias Ováricas , Hojas de la Planta/química , Resorcinoles/química , Resorcinoles/farmacología , Estereoisomerismo , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Bioassay-guided fractionation of a CH(2)Cl(2)/MeOH extract of the small twigs of Brachylaena ramiflora var. ramiflora resulted in the isolation of the two new triterpene esters 1 and 2 and five known triterpenoids, alpha-amyrin palmitate (3), beta-amyrin palmitate (4), beta-amyrin acetate (5), lupeyl acetate (6), and lupeol (7). The structures of the two new compounds were established as kairatenyl palmitate (1) and hopenyl palmitate (2) on the basis of 1D and 2D NMR spectroscopic data interpretation and chemical conversions. All the isolated compounds showed weak cytotoxicity against the A2780 human ovarian cancer cell line.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Asteraceae/química , Ésteres/aislamiento & purificación , Palmitatos/aislamiento & purificación , Plantas Medicinales/química , Triterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Ésteres/química , Ésteres/farmacología , Femenino , Humanos , Concentración 50 Inhibidora , Madagascar , Conformación Molecular , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Ácido Oleanólico/análogos & derivados , Neoplasias Ováricas , Palmitatos/química , Palmitatos/farmacología , Triterpenos Pentacíclicos , Brotes de la Planta/química , Espectroscopía Infrarroja por Transformada de Fourier , Estereoisomerismo , Triterpenos/química , Triterpenos/farmacología , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Bioassay-guided fractionation of a CH2Cl2-MeOH extract of the bark of Ochrocarpos punctatus resulted in the isolation of seven new coumarins, ochrocarpins A-G (1-7), three new benzophenone derivatives, ochrocarpinones A-C (8-10), and five known coumarins, mammea A/AC cyclo F (11), mammea A/AD cyclo D (12), mammea A/AB cyclo F (13), mammea A/AA cyclo F (14), mammea A/AB cyclo D (15), and 15,16-dihydro-16-hydroperoxyplukenetione (16). The structures of compounds 1-10 were established on the basis of extensive 1D and 2D NMR spectroscopic data interpretation. All compounds exhibited cytotoxicity against the A2780 ovarian cancer cell line.