RESUMEN
In our ongoing research program on the proapoptotic function of saponins, two previously undescribed saponins, named zygiaosides E (1: ) and F (2: ), were isolated from the leaves of Albizia zygia. Their structures were established based on extensive analysis of 1D and 2D NMR data, HR-ESI-MS analysis, and by chemical degradation. The proapoptotic effect of zygiaoside E (1: ) was evaluated on human malignant melanoma (A375), human epidermoid cancer (A431), and normal Homo sapiens skin tissue (TE 353.SK.) cell lines by cytometric analysis. Zygiaoside E (1: ) induced apoptosis of the two human cancer cell lines (A375 and A431) in a dose-dependent manner at 1 µM but did not induce apoptosis in noncancerous skin cells (TE 353.Sk), even when treated with concentrations up to 15 µM. The underlying mechanism of the apoptosis induction activity of zygiaoside E (1: ) on the mitochondrial membrane potential status in A375 cells was further assessed by monitoring the uptake rate of DiOC6, a mitochondrial specific and voltage-dependent fluorescent dye. The number of malignant melanoma cells emitting high fluorescence levels was decreased when cells were treated with 3 or 5 µM of zygiaoside E (1: ) during either 12 or 24 h, thereby revealing a drop of mitochondrial membrane potential in A375 cells upon treatment, which indicated mitochondrial perturbation.
Asunto(s)
Albizzia , Melanoma , Saponinas , Triterpenos , Humanos , Albizzia/química , Triterpenos/farmacología , Línea Celular Tumoral , Saponinas/farmacología , Saponinas/química , Apoptosis , Melanoma/tratamiento farmacológico , Melanoma/metabolismo , Melanoma/patología , Potencial de la Membrana MitocondrialRESUMEN
The study of the MeOH extract of the leaves of Campylospermum excavatum led to the isolation of a nitrile glucoside, named campyloside C (1) and an original derivative of ochnaflavone, 7-O-methylochnaflavone (2), along with three known biflavonoids, amentoflavone, sequoiaflavone, and sotetsuflavone (3 - 5). The linkage site of the sub-units of 2 was confirmed by chemical correlation, after semi-synthesis of a trimethoxylated derivative of ochnaflavone (2a). The structures of these compounds as well as their relative and absolute configurations were assigned by 1D- and 2D-NMR experiments, HR-ESI-MS and Electronic Circular Dichroism (ECD) calculations. A low-pass J filter HMBC experiment was performed in order to define the configuration of the double bond of 1. All of the biflavonoids were evaluated against protozoan parasites. Amentoflavone moderately inhibited the promastigote form of Leishmania infantum.
Asunto(s)
Biflavonoides/química , Glucósidos/química , Nitrilos/química , Ochnaceae/química , Animales , Antiprotozoarios/química , Antiprotozoarios/aislamiento & purificación , Antiprotozoarios/farmacología , Biflavonoides/aislamiento & purificación , Biflavonoides/farmacología , Línea Celular , Dicroismo Circular , Flavonoides/síntesis química , Flavonoides/química , Glucósidos/aislamiento & purificación , Leishmania/efectos de los fármacos , Leishmania/fisiología , Macrófagos/citología , Macrófagos/efectos de los fármacos , Macrófagos/parasitología , Espectroscopía de Resonancia Magnética , Ratones , Conformación Molecular , Ochnaceae/metabolismo , Hojas de la Planta/química , Hojas de la Planta/metabolismo , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
As part of our search for new bioactive saponins from Cameroonian medicinal plants, two new oleanane-type saponins, named gummiferaosides D and E (1 and 2), along with one known saponin, julibroside J8 (3), were isolated from the roots of Albizia gummifera. Their structures were established on the basis of extensive 1D- and 2D-NMR (1 H- and 13 C-NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY, and HMBC) and HR-ESI-MS studies, and by chemical evidence. The apoptotic effect of saponins 1 - 3 was evaluated on the A431 human epidermoid cancer cell. Flow cytometric analyses showed that saponins 1 - 3 induced apoptosis of human epidermoid cancer cell (A431) in a dose-dependent manner.
Asunto(s)
Albizzia/química , Apoptosis/efectos de los fármacos , Raíces de Plantas/química , Saponinas/farmacología , Relación Dosis-Respuesta a Droga , Humanos , Conformación Molecular , Saponinas/química , Saponinas/aislamiento & purificación , Relación Estructura-Actividad , Células Tumorales CultivadasRESUMEN
Neuroinflammation is a common hallmark of Alzheimer's disease (AD), with NLRP3 inflammasome proven to be activated in microglia of AD patients' brains. In this study, a newly isolated biflavonoid (7,7'-di-O-methylchamaejasmin/M8) and a crude extract of the plant Khaya grandifoliola (KG) were investigated for their inhibitory effect on inflammasome activation. In preliminary experiments, M8 and KG showed no cytotoxicity on human macrophage-like differentiated THP-1 cells and exhibited anti-inflammatory inhibition of nitric oxide produced following lipopolysaccharide stimulation. Furthermore, M8 and KG blocked IL-1ß and IL-18 production by reducing NLRP3 inflammasome components including NFκB, NLRP3, Caspase-1, pro-IL-1ß, and pro-IL-18 at the mRNA and protein levels. Regarding the formation of ASC (apoptosis-associated speck-like protein containing a CARD) specks during inflammasome activation, the size and fluorescent intensity of the existing specks were unchanged across all treatment conditions. However, M8 and KG treatments were shown to prevent further speck formation. In addition, experiments on amyloid ß phagocytosis showed that M8 and KG pretreatments can restore the phagocytic activity of THP-1 cells, which was impaired following inflammasome activation. Altogether, our findings describe for the first time a promising role of biflavonoids and KG extract in preventing inflammasome activation and protecting against neuroinflammation, a key factor in AD development.
RESUMEN
In our continuing search of saponins from the plants of Fabaceae family, phytochemical investigation of the roots of Acacia polyacantha, led to the isolation and structural characterization of six undescribed triterpenoid saponins, named polyacosides A-F (1-6). Their structures were established, using extensive analysis by NMR techniques, mainly 1D NMR (1H, 13C, and DEPT) and 2D NMR (COSY, NOESY, HSQC, TOCSY and HMBC) experiments, HRESIMS and by comparison with the literature data, as 3-O-[ß-d-xylopyranosyl-(1 â 4)- [ß-d-galactopyranosyl-(1 â 2)-ß-d-xylopyranosyl-(1 â 2)]-α-l-arabinopyranosyl]-21-O-[Cis-2-methoxycinnamoyl] machaerinic acid (1), 3-O-[ß-d-xylopyranosyl-(1 â 4)- [ß-d-galactopyranosyl-(1 â 2)-ß-d-xylopyranosyl-(1 â 2)]-α-l-arabinopyranosyl]-21-O- [Cis-3,4-dimethoxycinnamoyl] machaerinic acid. (2), 3-O- [ß-d-galactopyranosyl-(1 â 2)-ß-d-xylopyranosyl-(1 â 2)-α-l-arabinopyranosyl]-21-O- [Trans-4-methoxycinnamoyl] machaerinic acid (3), 3-O- [ß-d-glucopyranosyl-(1 â 2)-ß-d-glucopyranosyl] -21-O- [Cis-3,4-dimethoxycinnamoyl] machaerinic acid (4), 3-O- [ß-d-glucopyranosyl-(1 â 2)-ß-d-glucopyranosyl] -21-O- [Cis-2-methoxycinnamoyl] machaerinic acid (5) and 3-O- [ß-d-glucopyranosyl-(1 â 2)-ß-d-glucopyranosyl] -21-O- [Trans-4-methoxycinnamoyl] machaerinic acid (6). Our findings highlight the presence of methoxycinnamoyl group linked to C-21 of the machaerinic acid aglycone moiety as first report of 21-methoxycinnamoyl-machaerinic acid derivative from the plants of Acacia genus (Fabaceae). This represents therefore a valuable contribution to the chemotaxonomy of the Acacia genus of Fabaceae family, which is known to be a rich source of triterpenoid saponins.
Asunto(s)
Acacia , Saponinas , Triterpenos , Acacia/química , Estructura Molecular , Raíces de Plantas/química , Saponinas/química , Triterpenos/químicaRESUMEN
As part of our continuing study of apoptosis-inducing saponins from Cameroonian Albizia genus, one new triterpenoid saponin, named adianthifolioside J (1), together with the known gummiferaoside E (2), were isolated from Albizia adianthifolia stems. The structure of the new saponin (1), was established on the basis of extensive analysis of 1 D and 2 D NMR (1H-, 13C-NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-[ß-D-xylopyranosyl-(1â2)-ß-D-fucopyranosyl-(1â6)-ß-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(ß-D-quinovopyranosyl)octa-2,7-dienoyl]-(ß-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid-28-O-ß-D-glucopyranosyl-(1â3)-[5-O-acetyl-α-L-arabinofuranosyl-(1â4)]-α-L-rhamnopyranosyl-(1â2)-ß-D-glucopyranosyl ester (1). The pro-apoptotic activity of the new isolated saponin 1 was evaluated, using Annexin V-FITC binding assay, on the A431 human epidermoid cancer cell. The result showed that adianthifolioside J (1) displayed weak pro-apoptotic activity.
Asunto(s)
Acacia , Albizzia , Saponinas , Triterpenos , Apoptosis , Humanos , Estructura MolecularRESUMEN
In our continuing search of saponins from the plant of Sapindaceae family, phytochemical investigation of the stem barks of Pancovia turbinata Radlk., led to the isolation and structural characterization of two new triterpenoid saponins, named turbinatosides A-B (1-2), one new farnesyl glycoside, named turbinoside A (3), one new coumarin glucoside, named panturboside A (4), together with a known saponin (5). The structures of the new compounds were established, using extensive analysis of NMR techniques, mainly 1D NMR (1H, 13C, and DEPT) and 2D NMR (COSY, NOESY, HSQC, HSQC-TOCSY and HMBC) experiments, HRESIMS and by comparison with the literature data, as 3-O-ß-d-xylopyranosyl-(1 â 3)-α-l-arabinopyranosyl-(1 â 4)-ß-d-glucopyranosyl-(1 â 3)-α-l-rhamnopyranosyl-(1 â 2)-α-l-arabinopyranosylhederagenin 28-O-ß-d-glucopyranosyl ester (1), 3-O-α-l-arabinopyranosyl-(1 â 4)-ß-d-glucopyranosyl-(1 â 3)-α-l-rhamnopyranosyl-(1 â 2)-α-l-arabinopyranosylhederagenin 28-O-ß-d-xylopyranosyl-(1 â 4)-ß-d-glucopyranosyl ester (2), 1-O-{ß-d-glucopyranosyl-(1 â 3)-α-l-rhamnopyranosyl-(1 â 2)-[α-l-rhamnopyranosyl-(1 â 6)]-ß-d-glucopyranosyl}-(2E,6E)-farnes-1,12-diol (3), and 5-O-ß-d-glucopyranosyl-5,6,7-trihydroxy-8-methoxycoumarin (4), respectively. Our findings highlight the presence of -3Rha-2Ara-3hederagenin oligosaccharidic sequence usually described in saponins from Sapindoideae subfamily of Sapindaceae family, as well as farnesol glycosides, and represent therefore a valuable contribution to the chemotaxonomy of the Sapindoideae subfamily.
Asunto(s)
Saponinas , Glicósidos , Ácido Oleanólico/análogos & derivados , SapindaceaeRESUMEN
In a continuation of our study on constituents of P. guineense now focusing on the search for saponins, phytochemical investigation of the n-BuOH fraction of P. guineense stem bark led to the isolation of three previously undescribed triterpenoid saponins, named guineenosides AâC (1â3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-{α-l-rhamnopyranosyl-(1 â 3)-ß-d-xylopyranosyl-(1 â 2)-α-l-arabinopyranosyl-(1 â 4)-α-l-rhamnopyranosyl-(1 â 3)-[α-l-arabinofuranosyl-(1 â 4)]-α-l-rhamnopyranosyl-(1 â 3)-ß-d-fucopyranosyl} polygalacic acid 28-O-α-l-rhamnopyranosyl-(1 â 4)-α-l-rhamnopyranosyl-(1 â 3)-ß-d-xylopyranosyl ester (1), 3-O-{α-l-rhamnopyranosyl-(1 â 3)-ß-d-xylopyranosyl-(1 â 2)-α-l-arabinopyranosyl-(1 â 4)-α-l-rhamnopyranosyl-(1 â 3)-[α-l-arabinofuranosyl-(1 â 4)]-α-l-rhamnopyranosyl-(1 â 3)-ß-d-fucopyranosyl} polygalacic acid 28-O-ß-d-glucopyranosyl-(1 â 3)-α-l-rhamnopyranosyl-(1 â 4)-α-l-rhamnopyranosyl-(1 â 3)-ß-d-xylopyranosyl ester (2), and 3-O-{α-l-rhamnopyranosyl-(1 â 2)-ß-d-xylopyranosyl-(1 â 3)-ß-d-fucopyranosyl} polygalacic acid 28-O-[α-l-rhamnopyranosyl-(1 â 4)-α-l-rhamnopyranosyl-(1 â 3)-ß-d-xylopyranosyl ester (3). This is the first report of triterpenoid saponins from P. guineense.
Asunto(s)
Glicósidos , Ácido Oleanólico/análogos & derivados , Saponinas , Piper , Triterpenos/químicaRESUMEN
BACKGROUND: Chemical and pharmacological investigations were performed on the stems of Cordia batesii (Boraginaeae); chemical studies included quantum calculations applied on a newly described compound. RESULTS: A new derivative of allantoin (1) named batesiin (2) was characterized. Thirteen other known compounds involving allantoin (1) were either isolated or identified. GC-MS enabled the identification of six compounds from a fraction containing essential oil. MeOH extract and some isolated compounds were tested in vitro against Pf7G8 CQS and Pf Dd2 CQR strains of Plasmodium falciparum; extract disclosed a moderate antiplasmodial activity (IC50 = 50 µg mL-1). Meantime, the CH2Cl2 extract and essential oil fraction were tested on a resistant mycobacterial strain of Mycobacterium tuberculosis; a potent antimycobacterial activity with a MIC = 9.52 µg mL-1 was deduced from essential oil. Density functional theory (DFT) calculations were carried on batesiin (2). Calculated chemical shifts at B3LYP/6-31G(d,p) and MPW1PW91/6-31G+(d,p) showed much better correlations with the experimental data. Time dependent DFT at B3LYP/6-31G+(d,p) displayed a major absorption band 3.01 nm higher than the experimental value. CONCLUSION: Cordia batesii can be considered as promising in search of compounds with antimalarial and antitubercular properties. DFT studies are very helpful when trying to learn more about the spectroscopic insights of a derivative of allantoin (1).
RESUMEN
Chemical investigation of the methanol extract of the roots of Lecaniodiscus cupanioides led to the isolation and characterisation of three new sesquiterpene glycosides, named cupanioidesosides A (1), B (2) and C (3), together with one new triterpenoid saponin named lecanioside A (4), Their structures were established by extensive analysis of spectroscopic methods including 1D and 2D NMR techniques (COSY, NOESY, TOCSY, HSQC, and HMBC) and HRESIMS. The four new compounds were evaluated for their antiproliferative activity against the Caco-2 cell line (human epithelial cell line). None of the isolated compounds showed positive activity in our assay. Our findings represent a valuable contribution to the chemotaxonomy Lecaniodiscus genus of the subfamily of Sapindoideae of Sapindaceae family, known to be a rich source of farnesol glycosides.
Asunto(s)
Farnesol/química , Glicósidos/química , Extractos Vegetales/química , Raíces de Plantas/química , Sapindaceae/química , Triterpenos/química , Células CACO-2 , Farnesol/aislamiento & purificación , Glicósidos/aislamiento & purificación , Humanos , Conformación Molecular , Extractos Vegetales/aislamiento & purificación , Triterpenos/aislamiento & purificaciónRESUMEN
The chemical investigation of the flowers and twigs of Calliandra calothyrsus (Fabaceae) led to the isolation of three new oleanane-type triterpenoid saponins, named calothyrsusosides AC (13). Their structures were established by direct interpretation of their spectral data, mainly HRESIMS, 1D NMR and 2D NMR (1H, 1H NMR DOSY, 13C NMR, COSY, HSQC, HMBC, HSQC-TOCSY and NOESY) and by comparison with literature data. Compounds 1 and 2 were tested for their antiproliferative activity against two digestive carcinoma human cell lines: Hep3B (hepatocellular carcinoma) and Caco-2 (epithelial colorectal adenocarcinoma). Both compounds exhibited an antiproliferative activity against the Hep3B cell line, with IC50 values of 6.0 and 6.5 µM, respectively, while no effect was detected against the epithelial colorectal adenocarcinoma Caco-2 (CC50 > 25 µM).
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Fabaceae/química , Saponinas/farmacología , Triterpenos/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Células CACO-2 , Camerún , Línea Celular Tumoral , Ensayos de Selección de Medicamentos Antitumorales , Flores/química , Humanos , Estructura Molecular , Ácido Oleanólico/análogos & derivados , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Componentes Aéreos de las Plantas/química , Saponinas/aislamiento & purificación , Triterpenos/aislamiento & purificaciónRESUMEN
As a continuation of our interest in the study of triterpenoid saponins from Albizia zygia, phytochemical investigation of its stem barks led to the isolation of two new oleanane-type saponins, named zygiaosides C-D (1-2). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H-, 13C NMR, DEPT, COSY, TOCSY, ROESY, HSQC and HMBC) experiments, HRESIMS studies, and by chemical evidence as, 3-O-[ ß-d-glucopyranosyl-(1â2)-[α-l-arabinopyranosyl-(1â6)]-ß-d-glucopyranosyl]-21-O-[(2E,6S)-2,6-dimethyl-6-O-(ß-d-quinovopyranosyl) octa-2,7-dienoyl]acacic acid 28-O-α-l-arabinofuranosyl-(1â4)-[ß-d-glucopyranosyl-(1â3)]-α-l-rhamnopyranosyl-(1â2)-ß-d-glucopyranosyl ester (1) and 3- O-[ß-d-glucopyranosyl-(1â2) -[ ß-d-fucopyranosyl-(1â6)]-ß-d-glucopyranosyl]-21-O-[(2E,6S)-2,6-dimethyl-6-O-(ß-D-quinovopyranosyl) octa-2,7-dienoyl]acacic acid 28-O-α-l-arabinofuranosyl-(1â4)-[ß-d-glucopyranosyl-(1â3)]-α-l-rhamnopyranosyl-(1â2)-ß-d-glucopyranosyl ester (2).
Asunto(s)
Albizzia/química , Saponinas/química , Espectroscopía de Resonancia Magnética , Estructura Molecular , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/química , Corteza de la Planta/química , Saponinas/aislamiento & purificación , Espectrometría de Masa por Ionización de ElectrosprayRESUMEN
Two nitrile glucosides (1S,3S,4S,5R)-4-benzoyloxy-2-cyanomethylene-3,5-dihydroxycyclohexyl-1-O-beta-glucopyranoside (campyloside A) and (1S,3S,4S,5R)-5-benzoyloxy-2-cyanomethylene-3-hydroxy-4-(2-pyrrolcarboxyloxy)cyclohexyl-1-O-beta-glucopyranoside (campyloside B) were isolated from the stem roots of Campylospermum glaucum, whereas serotobenine was isolated from Ouratea turnarea. The structure elucidations were based on spectroscopic evidence. The biological assays of compounds and crude extract of plant species showed good antimicrobial activity of crude extracts against Gram-positive cocci.
Asunto(s)
Glucósidos/química , Glucósidos/farmacología , Indoles/química , Indoles/farmacología , Nitrilos/química , Ochnaceae/química , Glucósidos/clasificación , Cocos Grampositivos/efectos de los fármacos , Indoles/clasificación , Espectroscopía de Resonancia Magnética , Estructura MolecularRESUMEN
As part of our study of the proapoptotic function of saponins from Cameroonian's Albizia genus, phytochemical investigation of the roots of Albizia adianthifolia led to the isolation of three new triterpenoid saponins, named adianthifoliosides GI (13). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H-, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-[ß-d-glucopyranosyl-(1â¯ââ¯2)-ß-D-fucopyranosyl-(1â¯ââ¯6)-ß-d-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(ß-D-quinovopyranosyl)octa-2,7-dienoyl]-(ß-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid-28-O-ß-d-xylopyranosyl-(1â¯ââ¯3)-[5-O-acetyl-α-L-arabinofuranosyl-(1â¯ââ¯4)]-α-L-rhamnopyranosyl-(1â¯ââ¯2)-ß-d-glucopyranosyl ester (1), 3-O-[ß-d-glucopyranosyl-(1â¯ââ¯2)-ß-D-fucopyranosyl-(1â¯ââ¯6)-ß-d-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(ß-D-quinovopyranosyl)octa-2,7-dienoyl]-(ß-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid 28-O-ß-d-xylopyranosyl-(1â¯ââ¯3)-[α-L-arabinofuranosyl-1â¯ââ¯4)]-α-L-rhamnopyranosyl-(1â¯ââ¯2)-ß-d-glucopyranosyl ester (2), and 3-O-[ß-d-glucopyranosyl-(1â¯ââ¯2)-ß-D-fucopyranosyl-(1â¯ââ¯6)-ß-d-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(ß-D-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(ß-D-quinovopyranosyl)octa-2,7-dienoyl]-ß-D-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28-O-ß-d-xylopyranosyl-(1â¯ââ¯3)-[α-L-arabinofuranosyl-1â¯ââ¯4)]-α-L-rhamnopyranosyl-(1â¯ââ¯2)-ß-d-glucopyranosyl ester (3). The apoptotic effect of saponins 1-3 was evaluated on the A431 human epidermoid cancer cell. Flow cytometric analyses showed that saponins 1-3 induced apoptosis of human epidermoid cancer cell (A431) in a dose-dependent manner.
Asunto(s)
Albizzia/química , Apoptosis/efectos de los fármacos , Saponinas/química , Camerún , Línea Celular Tumoral , Humanos , Estructura Molecular , Raíces de Plantas/químicaRESUMEN
Two bisindoline alkaloids, contortarine A, 16-epi-pleiomutinine and a reaction product of pleiomutinine, namely N4-chloromethyl-pleiomutinine, were isolated from the roots of Tabernaemontana contorta Stapf. together with five known compounds: pleiomutinine, 1-carbomethoxy-ß-carboline, strictosidine lactam, pleiocarpamine, and pleiocarpine. The structures and relative configuration of these alkaloids were determined by extensive 1D and 2D NMR, and MS measurements. The absolute configuration of these compounds was determined by comparison of experimental and calculated ECD spectra. Among the isolated compounds, contortarine A, 1-carbomethoxy-ß-carboline and strictosidine lactam presented cancer chemopreventive properties through either quinone reductase (QR) induction with CD values of 16.0 ± 2.5, 30.2 ± 6.1 and 23.1 ± 4.6 µM, respectively, while pleiomutinine and 16-epi-pleiomutinine displayed the inhibition of TNF-α induced NF-κB activity with IC50 at 11.7 ± 2.6 and 3.4 ± 1.1 µM, respectively.
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Alcaloides/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Indoles/farmacología , Neoplasias/prevención & control , Tabernaemontana/química , Alcaloides/química , Alcaloides/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Células HEK293 , Humanos , Indoles/química , Indoles/aislamiento & purificación , Estructura Molecular , FN-kappa B/antagonistas & inhibidores , FN-kappa B/metabolismo , Neoplasias/patología , Raíces de Plantas/químicaRESUMEN
A total of 14 compounds were isolated from the ethanol bark extract of O. kirkii S. Moore (Fabaceae) by alternating isocratic and step gradient elution high-speed counter-current chromatography (HSCCC) methods, using several solvent systems with reference to the polarity of compounds being purified. The extract was successively fractionated with generic solvent systems including n-hexane-ethanol-water (4:2:2) and ethyl acetate-water (1:1). Resulting fractions were further purified using the following preparative gradient elution consisting of ethyl acetate-n-butanol-water (X:Y:10), (X:Y=9:1 (I); 8:2 (II); 7:3 (III); 6:4 (IV); 5:5 (V); 4:6 (VI) 3:7 (VII) and n-hexane- ethyl acetate-methanol-water (1:X:1:1), X=1, 2, 2.5, 3 solvent systems. Two flavone glycosides, apigenin-6-C-ß-d-glucopyranosyl-4'-O-[ß-d-glucopyranosyl-(1â5)]-ß-d-apiofuranoside (1) and apigenin-6-C-ß-d-glucopyranosyl-4'-O-ß-d-apiofuranoside (2), and one biflavanone diglycoside 7,7â³-di-O-ß-d-glucosylliquiritigeninyl-(I-3,II-3)-naringenin (4) were isolated as new compounds along with other 11 known ones. The structures of the isolated compounds were identified by HPLC-UV, ESI-MS, 1D and 2D NMR and comparison with literature data. Thus, over common traditional chromatographic methods, the present study shows that HSCCC is a useful and fast method for natural product research with no losses and lower solvent use.
Asunto(s)
Distribución en Contracorriente/métodos , Fabaceae/química , Fenoles/aislamiento & purificación , Corteza de la Planta/química , Productos Biológicos/química , Cromatografía Líquida de Alta Presión , Flavonas/aislamiento & purificación , Glicósidos/aislamiento & purificación , Solventes , Factores de TiempoRESUMEN
Investigation of the aerial parts of Ouratea sulcata led to the isolation of a biflavonoid named sulcatone A, together with the known compounds, 3-hydroxy-2,3-dihydroapigenyl-[I-4',O,II-3']-dihydrokaempferol, amentoflavone, lophirone A, agathisflavone, stigmasterol and stigmasteryl-3-O-beta-D-glucopyranoside. The structure of the compound was assigned as apigenyl-[I-4',O,II-3']-dihydrokaempferol, by means of spectroscopic analysis. Sulcatone A and 3-hydroxy-2,3-dihydroapigenyl-[I-4',O,II-3']-dihydrokaempferol exhibited significant in vitro antimicrobial activities against a range of microorganisms.
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Antibacterianos/química , Antibacterianos/aislamiento & purificación , Biflavonoides/aislamiento & purificación , Biflavonoides/farmacología , Ochnaceae/química , Componentes Aéreos de las Plantas/química , Antibacterianos/farmacología , Biflavonoides/química , Quempferoles/química , Quempferoles/farmacología , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Estructura MolecularRESUMEN
Seven flavonoids, hemerocallone (1), 6,7-dimethoxy-3',4'-dimethoxyisoflavone (2), amentoflavone (4), agathisflavone (6), cupressuflavone (8), robustaflavone (9) and epicatechin (10), together with three other compounds, lithospermoside (3), ß-D-fructofuranosyl-α-D-glucopyranoside (5) and 3ß-O-D-glucopyranosyl-ß-stigmasterol (7), were isolated from the ethyl acetate extract of the stem bark of Ochna schweinfurthiana F. Hoffm. All the compounds were characterised by spectroscopic and mass spectrometric methods, and by comparison with literature data. Cytotoxicity of the extracts and compounds against cervical adenocarcinoma (HeLa) cells was evaluated by MTT assay. Compounds 4 and 6 exhibited good cytotoxic activity, with IC50 values of 20.7 and 10.0 µM, respectively.
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Flavonoides/química , Ochnaceae/química , Corteza de la Planta/química , Extractos Vegetales/química , Biflavonoides/química , Células HeLa , Humanos , Concentración 50 Inhibidora , Estructura MolecularRESUMEN
In a chemical investigation on the stem bark of Ouratea flava, two biflavonoids: 1-[3-(2,4-dihydroxy-benzoyl)-4,5,6-trihydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl] -3-(4-hydroxy-phenyl) -propenone (flavumone A) and 3-(2,4-dihydroxy-benzoyl)-4-hydroxy-2,7-bis-(4-hydroxy-phenyl) -7,8- dihydro-furo[2,3-f]chromen-9-on (flavumone B) were isolated along with five known flavonoids. Their structures were established by various analyses including 2D-NMR spectroscopy.