RESUMEN
Artemisinic acid (2) was modified through allylic oxidation at C-3 or conjugate addition at C-13 to afford 12 methyl artemisinate derivatives (4-15). Photooxidation of the derivatives yielded eight new artemisinin analogues, including 13-cyanoartemisinin (16), 13-methoxycarbonyl artemisinin (17), 13-methoxyartemisinin (18), 13-ethylsulfonylartemisinin (19), 13-nitromethylartemisinin (20), 13-(1-nitroethyl)artemisinin (21), (3R)-3-hydroxyartemisinin (22), and (3R)-3-acetoxyartemisinin (23). Among the analogues, only compound 20 had antimalarial activity comparable to artemisinin (1).
Asunto(s)
Antimaláricos , Artemisininas , Medicamentos Herbarios Chinos , Sesquiterpenos , Animales , Antimaláricos/síntesis química , Antimaláricos/química , Antimaláricos/farmacología , Cloroquina/farmacología , Cromatografía en Capa Delgada , Farmacorresistencia Microbiana , Medicamentos Herbarios Chinos/síntesis química , Medicamentos Herbarios Chinos/química , Medicamentos Herbarios Chinos/farmacología , Cromatografía de Gases y Espectrometría de Masas , Humanos , Técnicas In Vitro , Células KB , Espectroscopía de Resonancia Magnética , Estructura Molecular , Plasmodium falciparum/efectos de los fármacos , Sesquiterpenos/síntesis química , Sesquiterpenos/química , Sesquiterpenos/farmacología , Espectrofotometría Infrarroja , Espectroscopía Infrarroja por Transformada de Fourier , Estereoisomerismo , Relación Estructura-ActividadRESUMEN
Alkaloids are an important group of diversely distributed, chemically, biologically and commercially significant natural products. This article suggests why now, with the presently available technology, and the remaining biome available and reasonably accessible, is an opportune moment to consciously focus on the discovery of further alkaloids with pharmacophoric utility.
Asunto(s)
Alcaloides/uso terapéutico , Quimioterapia/tendencias , Plantas Medicinales , HumanosRESUMEN
Nine tropane alkaloid aromatic esters (1-9) were isolated from the roots of Erythroxylum pervillei by following their potential to reverse multidrug-resistance with vinblastine-resistant oral epidermoid carcinoma (KB-V1) cells. All isolates, including seven new structures (3-9), were evaluated against a panel of human cancer cell lines, and it was found that alkaloids 3 and 5-9 showed the greatest activity with KB-V1 cells assessed in the presence of vinblastine, suggesting that these new compounds are potent modulators of P-glycoprotein. Confirmatory results were obtained with human ovarian adenocarcinoma (SKVLB) cells evaluated in the presence of adriamycin and synergistic studies performed with several cell lines from the NCI tumor panel. The structures of the new compounds were determined using spectroscopic techniques. Single-crystal X-ray analysis was performed on the monoester, tropane-3 alpha,6 beta,7 beta-triol 3-phenylacetate (1).
Asunto(s)
Alcaloides/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Erythroxylaceae/química , Plantas Medicinales/química , Tropanos/aislamiento & purificación , Subfamilia B de Transportador de Casetes de Unión a ATP/metabolismo , Alcaloides/química , Alcaloides/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Cristalografía por Rayos X , Doxorrubicina/farmacología , Resistencia a Múltiples Medicamentos , Ensayos de Selección de Medicamentos Antitumorales , Ésteres/química , Ésteres/aislamiento & purificación , Ésteres/farmacología , Femenino , Humanos , Madagascar , Medicina Tradicional , Conformación Molecular , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Neoplasias Ováricas , Raíces de Plantas/química , Espectrofotometría Infrarroja , Estereoisomerismo , Tropanos/química , Tropanos/farmacología , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Eight new triterpene glycosides named cimiracemosides A-H, respectively, and eight known triterpene glycosides were isolated from the rhizome extracts of black cohosh (Cimicifuga racemosa). The new compounds were determined by spectral data to be 21-hydroxycimigenol-3-O-alpha-L-arabinopyranoside (1), 21-hydroxycimigenol-3-O-beta-D-xylopyranoside (2), cimigenol-3-O-alpha-L-arabinopyranoside (3), 12beta-acetoxycimigenol-3-O-alpha-L-arabinopyranoside (4), 24-acetylisodahurinol-3-O-beta-D-xylopyranoside (5), 20(S),22(R), 23(S),24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3be ta,23, 24-trihydroxy-9,19-cycloanost-7-ene-3-O-beta-D-xylopyranoside (6), 20(S),22(R),23(S),24(R)-16beta:23;22:25-diepoxy-12beta -acetoxy-3beta, 23,24-trihydroxy-9,19-cycloanost-7-en-3-O-alpha-L-arabinopyrano side (7), and 20(S),22(R),23(S), 24(R)-16beta:23;22:25-diepoxy-12beta-acetoxy-3beta,23, 24-trihydroxy-9,19-cycloanostane-3-O-beta-D-xylopyranoside (8).
Asunto(s)
Glicósidos/aislamiento & purificación , Plantas Medicinales/química , Triterpenos/aislamiento & purificación , Glicósidos/química , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Estructura Molecular , Triterpenos/químicaRESUMEN
An extract of the aerial parts from Alomia myriadenia Schultz-Bip. ex Baker (Asteraceae) showed significant cytotoxicity against a panel of human cancer cell lines in a screening of extracts from Brazilian Atlantic Forest plant species. Employing a bioassay-linked HPLC-electrospray/MS method, followed by semi-preparative HPLC, the active component was isolated and characterized as a mixture of epimers of the labdane diterpene 12S,16-dihydroxy-ent-labda-7,13-dien-15,16-olide.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Asteraceae/química , Diterpenos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Cromatografía Líquida de Alta Presión , Diterpenos/química , Diterpenos/farmacología , Humanos , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Extractos Vegetales/química , Hojas de la Planta/química , Células Tumorales CultivadasRESUMEN
Bioactivity-directed fractionation of the CHCl(3) extract of the roots of Ekmanianthe longiflora resulted in the isolation of three new natural products, (2R,3R,4R)-3,4-dihydro-3, 4-dihydroxy-2-(3-methyl-2-butenyl)-1(2H)-naphthalenone (1), (2S,3R, 4R)-3,4-dihydro-3, 4-dihydroxy-2-(3-methyl-2-butenyl)-1(2H)-naphthalenone (2), and (2R, 3aR,9R,9aR)-9-hydroxy-2-(1-hydroxy-1-methylethyl)-2,3,3a,4,9 , 9a-hexahydro-naphtho[2,3-b]furan-4-one (3), together with the known compounds 2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-quinone (4), 2-acetylnaphtho[2,3-b]furan-4,9-quinone (5), dehydro-iso-alpha-lapachone (6), alpha-lapachone (7), catalponol, and epi-catalponol. The structures of 1-3 were determined using a combination of NMR spectroscopic techniques, and the absolute configurations of compounds 1 and 2 were obtained using Mosher ester methodology. Compounds 4-6 showed significant cytotoxicity in a panel of human cancer cells. alpha-Lapachone (7) exhibited only marginal activity, and catalponol and epi-catalponol were inactive in this regard. When tested at 72 mg/kg/injection in an in vivo mouse P-388 leukemia system, compound 4 was inactive (110% T/C).
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Furanos/aislamiento & purificación , Naftoles/aislamiento & purificación , Plantas Medicinales/química , Animales , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Furanos/farmacología , Humanos , Leucemia P388/tratamiento farmacológico , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Ratones , Naftoles/farmacología , Espectrofotometría Ultravioleta , Células Tumorales CultivadasRESUMEN
A new coumarin, 5-(4-hydroxyphenethenyl)-4,7-dimethoxycoumarin (1) was isolated from the combined ethyl acetate extracts of the root bark, root wood and stem bark of Monotes engleri, and found to be cytotoxic against two cell lines in a human tumor panel. Its structure was determined on the basis of spectroscopic methods.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Cumarinas/aislamiento & purificación , Plantas/química , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Cumarinas/química , Cumarinas/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Estructura Molecular , Análisis Espectral , Células Tumorales CultivadasRESUMEN
High-performance liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) was applied to the analysis of the flavonoids and their glycoside malonates of the flowers and leaves of red clover (Trifolium pratense). Through LC-MS comparative studies on the plant extracts and their malonate-free extracts, approximately 20 flavonoid glycoside malonates were detected in the flower extract. Eight were identified as genistin 6' '-O-malonate (39), formononetin 7-O-beta-D-glucoside 6' '-O-malonate (40), biochanin A 7-O-beta-D-glucoside 6' '-O-malonate (41), trifoside 6' '-O-malonate (42), irilone 4'-O-beta-D-glucoside 6' '-O-malonate (43), pratensein 7-O-beta-D-glucoside 6' '-O-malonate (44), isoquercitrin 6' '-O-malonate (45), and 3-methylquercetin 7-O-beta-D-glucoside 6' '-O-malonate (46). About 15 other flavonoids and clovamides were proved to be present in this extract. The study also found that the flowers contained flavones as the major flavonoids, whereas the leaves had isoflavones as the major flavonoids. This is the first detection of the six malonates (39 and 42-46) in the extracts of red clover, and among them, 42, 43, and 46 are new compounds.
Asunto(s)
Fabaceae/química , Flavonoides/química , Glicósidos/química , Malonatos/química , Plantas Medicinales , Cromatografía Líquida de Alta Presión , Espectrometría de Masas , Modelos QuímicosRESUMEN
Bioassay-directed fractionation of the flowers and leaves of Ratibida columnifera using a hormone-dependent human prostate (LNCaP) cancer cell line led to the isolation of 10 cytotoxic substances, composed of five novel xanthanolide derivatives (2-4, 7, and 8), a novel nerolidol derivative (9), and three known sesquiterpene lactones, 9alpha-hydroxy-seco-ratiferolide-5alpha-O-angelate+ ++ (1), 9alpha-hydroxy-seco-ratiferolide-5alpha-O-(2-methylbut yrate) (5), 9-oxo-seco-ratiferolide-5alpha-O-(2-methylbutyrate) (6), as well as a known flavonoid, hispidulin (10). On the basis of its cytotoxicity profile, compound 5 was selected for further biological evaluation, and was found to induce G1 arrest and slow S traverse time in parental wild type p53 A2780S cells, but only G2/M arrest in p53 mutant A2780R cells, with strong apoptosis shown for both cell lines. The activity of 5 was not mediated by the multidrug resistance (MDR) pump, and it was not active against several anticancer molecular targets (i.e., tubulin polymerization/depolymerization, topoisomerases, and DNA intercalation). While these results indicate that compound 5 acts as a cytotoxic agent via a novel mechanism, this substance was inactive in in vivo evaluations using the murine lung carcinoma (M109) and human colon carcinoma (HCT116) models.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Asteraceae/química , Plantas Medicinales/química , Sesquiterpenos/farmacología , Animales , Antineoplásicos Fitogénicos/aislamiento & purificación , Apoptosis/efectos de los fármacos , Ciclo Celular/efectos de los fármacos , ADN de Neoplasias/efectos de los fármacos , Ensayos de Selección de Medicamentos Antitumorales , Inhibidores Enzimáticos/farmacología , Femenino , Humanos , Sustancias Intercalantes/farmacología , Masculino , Ratones , Neoplasias Ováricas/tratamiento farmacológico , Neoplasias Ováricas/patología , Neoplasias de la Próstata/tratamiento farmacológico , Neoplasias de la Próstata/patología , Sesquiterpenos/aislamiento & purificación , Inhibidores de Topoisomerasa I , Tubulina (Proteína)/biosíntesis , Células Tumorales CultivadasRESUMEN
From the roots of Thalictrum faberi, six new phenolic aporphine-benzylisoquinoline alkaloids, 3-hydroxy-6'-desmethyl-9-O-methylthalifaboramine (1), 3-hydroxythalifaboramine (2), 6'-desmethylthalifaboramine (3); 3,5'-dihydroxythalifaboramine (4), 5'-hydroxythalifaboramine (5) and 3-hydroxy-6'-desmethylthalifaboramine (6) were isolated. Their structures were established through the use of one- and two-dimensional NMR techniques. All of the tested alkaloids showed potent cytotoxic and antimalarial activities.
Asunto(s)
Alcaloides/química , Antimaláricos/química , Antineoplásicos Fitogénicos/química , Plantas Medicinales , Inhibidores de la Transcriptasa Inversa/química , Alcaloides/aislamiento & purificación , Alcaloides/toxicidad , Animales , Fármacos Anti-VIH/química , Fármacos Anti-VIH/aislamiento & purificación , Fármacos Anti-VIH/toxicidad , Antimaláricos/aislamiento & purificación , Antimaláricos/toxicidad , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/toxicidad , Aporfinas/química , Aporfinas/aislamiento & purificación , Aporfinas/toxicidad , Supervivencia Celular/efectos de los fármacos , China , Humanos , Isoquinolinas/química , Isoquinolinas/aislamiento & purificación , Isoquinolinas/toxicidad , Células KB , Medicina Tradicional China , Estructura Molecular , Fenoles/química , Fenoles/aislamiento & purificación , Fenoles/toxicidad , Plasmodium falciparum/efectos de los fármacos , Inhibidores de la Transcriptasa Inversa/aislamiento & purificación , Inhibidores de la Transcriptasa Inversa/toxicidad , Células Tumorales CultivadasRESUMEN
Activity-guided fractionation of a stem extract of Mezzettia leptopoda using human oral epidermoid carcinoma (KB) cells led to the isolation of seven highly acylated oligorhamnosides. Four of these constituents are novel, namely, n-octyl 2-O-acetyl-alpha-L-rhamnopyranosyl-(1-->3)-2, 4-di-O-acetyl-alpha-L-rhamnopyranosyl-(1-->3)-4-O-hexanoyl-alpha-L-rh amnopyranoside (mezzettiaside 8) (1); n-octyl 2, 3-di-O-acetyl-alpha-L-rhamnopyranosyl-(1-->3)-4-O-hexanoyl-alpha-L-rh amnopyranoside (mezzettiaside 9) (2); n-octyl 2, 4-di-O-acetyl-alpha-L-rhamnopyranosyl-(1-->3)-4-O-hexanoyl-alpha-L-rh amnopyranoside (mezzettiaside 10) (3); and n-octyl 2,3, 4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1-->3)-4-O-hexanoyl-alpha-L-r hamnopyranoside (mezzettiaside 11) (4). Three known compounds were identified as mezzettiasides 2 (5), 3 (6), and 4 (7), respectively, previously isolated from this same plant. The structures of novel compounds 1-4 were determined by spectroscopic methods. All the isolates were evaluated against a panel of human cancer cell lines in this study, and compounds 1-2 and 4-7 were found to be weakly cytotoxic toward KB and/or human colon and lung cancer cell lines.
Asunto(s)
Oligosacáridos/farmacología , Plantas Medicinales/química , Animales , Antineoplásicos Fitogénicos , Secuencia de Carbohidratos , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Datos de Secuencia Molecular , Oligosacáridos/aislamiento & purificación , Hojas de la Planta/química , Ratas , Tailandia , Células Tumorales CultivadasRESUMEN
Activity-directed fractionation of a stem extract of Azadirachta excelsa using KB (human oral epidermoid carcinoma) cells led to the isolation of four meliacin-type limonoids. Two of these constituents were novel, namely, 2,3-dihydronimbolide and 3-deoxymethylnimbidate, and these were purified along with the known compounds, nimbolide and 28-deoxonimbolide. The structures of the new compounds were determined by spectroscopic methods. Nimbolide and 28-deoxonimbolide were broadly cytotoxic when evaluated against a panel of human cancer cell lines, while the two novel compounds were inactive in this regard. The defection of nimbolide and 28-deoxonimbolide as cytotoxic constituents was facilitated by an electrospray LC/MS dereplication procedure.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Colenos/aislamiento & purificación , Diterpenos/aislamiento & purificación , Lactonas/aislamiento & purificación , Limoninas , Plantas Medicinales/química , Secoesteroides/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Colenos/química , Colenos/farmacología , Diterpenos/química , Diterpenos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Lactonas/química , Lactonas/farmacología , Secoesteroides/química , Secoesteroides/farmacología , Análisis Espectral , Células Tumorales CultivadasRESUMEN
Two new cytotoxic compounds, 2-[10(Z)-heptadecenyl]-1,4-hydroquinone (1) and (4R,6R)-dihydroxy-4-[10(Z)-heptadecenyl]-2-cyclohexenone (2) have been isolated from a MeOH extract of seeds of Tapirira guianensis. The structures were established through spectral analysis of the isolates and their derivatives.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Ciclohexanonas/aislamiento & purificación , Hidroquinonas/aislamiento & purificación , Plantas Medicinales/química , Acetilación , Antineoplásicos Fitogénicos/farmacología , Ciclohexanonas/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Hidroquinonas/farmacología , Espectroscopía de Resonancia Magnética , Espectrofotometría Ultravioleta , Células Tumorales CultivadasRESUMEN
Extracts from the aerial parts of Sanicula europaea L. were investigated for their anti-HIV activity, and the 50% ethanolic extract was shown to exhibit the highest activity. A new triterpene saponin glycoside, 21 beta-(angeloyloxy)-3-O-[beta-D-arabinopyranosyl(1-->4)-beta- D-glucopyranosyl (1-->3)-beta-D-glucuronopyranosyl propyl ester]-3 beta,15,16,22 alpha,28 beta-pentahydroxy-delta(12)-oleanene, saniculoside N (1), in addition to the known phenolic acids, rosmarinic acid (2), and caffeic acid (3) were isolated as major components. Rosmarinic acid was established as the principal active substance.
Asunto(s)
Fármacos Anti-VIH/aislamiento & purificación , VIH-1/efectos de los fármacos , Ácido Oleanólico/análogos & derivados , Plantas Medicinales/química , Saponinas/aislamiento & purificación , Triterpenos/aislamiento & purificación , Fármacos Anti-VIH/farmacología , VIH-1/enzimología , Hidrólisis , Espectroscopía de Resonancia Magnética , Espectrometría de Masas , Conformación Molecular , Extractos Vegetales/química , Extractos Vegetales/farmacología , Inhibidores de la Transcriptasa Inversa/farmacología , Saponinas/farmacología , Triterpenos/farmacologíaRESUMEN
Two new hopene derivatives, 3 beta,6 beta-dihydroxy-21 alpha H-24-norhopa-4(23),22(29)-diene (1) and 3 beta,5 beta-dihydroxy-6 beta-[(4-hydroxybenzoyl)oxy]-21 alpha H-24-norhopa-4(23),22(29)-diene (2), together with cleomiscosin B (3) and 5,6-dimethoxy-7-hydroxycoumarin (umckalin), were isolated from the timber of Diatenopteryx sorbifolia. This is the first isolation of the norhopene skeleton from nature. The structures of the isolates were established by spectroscopic analysis.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Plantas Medicinales/química , Triterpenos/aislamiento & purificación , Acetilación , Antineoplásicos Fitogénicos/química , Secuencia de Carbohidratos , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Espectroscopía de Resonancia Magnética , Datos de Secuencia Molecular , Hojas de la Planta/química , Triterpenos/química , Células Tumorales Cultivadas , MaderaRESUMEN
A further investigation of Aster lingulatus has led to the isolation of two additional novel triterpene saponins, asterlingulatoside C [3-O-beta-D-glucopyranosyl-3 beta, 16 alpha-dihydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-alpha- L- arabinopyranoside] (1) and asterlingulatoside D [3-O-beta-D-glucopyranosyl-3 beta,16 alpha-dihydroxyolean-12-en-28-oic acid 28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1-->4)-alpha-L- rhamnopyranosyl-(1-->2)-alpha-L-arabinopyranoside] (2). Elucidation of the structures of 1 and 2 was mainly based on FABMS and 1D and 2D homonuclear and heteronuclear NMR techniques. Compounds 1 and 2 showed good inhibitory activity against DNA synthesis in human leukemia HL-60 cells with IC50 values of 8.8 and 6.1 microM, respectively.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Ácido Oleanólico/análogos & derivados , Plantas Medicinales/química , Saponinas/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Células HL-60 , Humanos , Espectroscopía de Resonancia Magnética , Saponinas/química , Saponinas/aislamiento & purificación , Espectrometría de Masa Bombardeada por Átomos Veloces , Relación Estructura-ActividadRESUMEN
From the leaves of Monotes engleri, five prenylated flavanones were isolated as constituents that displayed cytotoxic activity against several human cancer cell lines. There of these substances are novel, namely, 6-(1,1-dimethylallyl)naringenin, 6-(1,1-dimethylallyl)eriodictyol and 3'-O-methyl-6-(1,1-dimethylallyl)-eriodictyol, with the other two active substances being the known flavanones, 6,8-diprenyleriodictyol and hiravanone. Additionally, two novel, but non-cytotoxic, biogenetically related flavanones were isolated, 6-[(2RS)-hydroxy-3-methyl-3-butenyl]-8-prenyleriodictyol and 5,4'-dihydroxy-4",4"-dimethyl-5"-methyl-5"H-dihydrofurano[2",3": 6,7]flavanone. The structures of the new compounds were determined by spectral analysis 1D- and 2D-NMR experiments.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/toxicidad , Flavonoides/aislamiento & purificación , Flavonoides/toxicidad , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/toxicidad , Plantas Medicinales/química , Ensayos de Selección de Medicamentos Antitumorales , Glioma/tratamiento farmacológico , Humanos , Espectroscopía de Resonancia Magnética , Hojas de la Planta/química , Células Tumorales Cultivadas/efectos de los fármacosRESUMEN
Two oligofurostanosides were isolated from the seeds of Asparagus officinalis L and their structures characterized as 3-O-[alpha-L-rhamnopyranosyl-(1-->2)-(alpha-L-rhamnopyranosyl- (1-->4))-beta-D-glucopyranosyl]-26-O-[beta-D-glucopyranosyl]-(25R) -22 alpha-methoxyfurost-5-ene-3 beta,26-diol(methyl protodioscin) and its corresponding 22 alpha-hydroxy analogue (protodioscin). The structural identification was performed using detailed analysis of 1H- and 13C-NMR spectra including two-dimensional NMR spectroscopy (COSY, HMQC, NOESY and HMBC), and chemical conversions. These two compounds have been shown to inhibit the growth of human leukemia HL-60 cells in culture and macromolecular synthesis in a dose-dependent manner. The inhibitory effect on DNA synthesis was found to be irreversible.
Asunto(s)
Células HL-60/efectos de los fármacos , Saponinas/química , Esteroides/química , Verduras/química , Conformación de Carbohidratos , Secuencia de Carbohidratos , División Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Humanos , Datos de Secuencia Molecular , Extractos Vegetales , Saponinas/aislamiento & purificación , Saponinas/toxicidad , Semillas/química , Esteroides/aislamiento & purificación , Esteroides/toxicidadRESUMEN
Analysis of the alkaloidal fraction of the stem bark extract of Pachygone dasycarpa (Menispermaceae) resulted in the isolation of 10 known bisbenzylisoquinolines, (+)-tetrandrine, (+)-penduline, (+)-fangchinoline, (+)-atherospermoline, (+)-N-methyl-7-O-demethylpeinamine, (+)-daphnoline, (4-)-isotrilobine (1), (+)-cocsuline (2), (+)-tricordatine (3), (+)-2'-norcocsuline, and the new alkaloid (+)-12-O-methyltricordatine (4). The last bisbenzylisoquinoline alkaloid isolated, (+)-angchibangkine (5), is the first member of this alkaloid class found to possess three diphenyl ether bridges in the 7-6',8-7', and 11-12' positions. Structure elucidation of these alkaloids and of (+)-O-methylangchibangkine (6) was achieved by analysis of spectral data. Compounds 4-6 show antiplasmodial activity against Plasmodium falciparum.
Asunto(s)
Antimaláricos/aislamiento & purificación , Antineoplásicos Fitogénicos/aislamiento & purificación , Isoquinolinas/aislamiento & purificación , Epidermis de la Planta/química , Plantas Medicinales/química , Animales , Antimaláricos/farmacología , Antineoplásicos Fitogénicos/farmacología , Humanos , Isoquinolinas/farmacología , Células KB , Espectroscopía de Resonancia Magnética , Plasmodium falciparum/efectos de los fármacosRESUMEN
A new triterpene saponin, shimadoside A, has been isolated from Kalimeris shimadae and its structure deduced as 3-O-beta-D-glucopyranosiduronic acid-3 beta, 16 alpha-dihydroxyolean-12-en-28-oic acid-28-O-beta-D-xylopyranosyl-(1-->3)-beta-D-xylopyranosyl-(1--> 4)-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranoside by means of spectral data, especially NMR, including COSY, HMQC, HOHAHA and ROESY techniques, and chemical degradation.