RESUMEN
Six new diterpenes Euphonoids A-F including one ingenol (1), three lathyrane (2-5), one ent-abietane (6) and fifteen known derivatives (7-21) were isolated from the aerial parts of Euphorbia antiquorum L. Their structures were elucidated by physical data analysis. Compounds 1, 12, and 16 improve the melanogenesis in B16 cells in vitro.
Asunto(s)
Diterpenos/farmacología , Euphorbia/química , Melaninas/análisis , Vitíligo/metabolismo , Animales , Línea Celular Tumoral , China , Diterpenos/aislamiento & purificación , Melanoma Experimental/tratamiento farmacológico , Ratones , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Componentes Aéreos de las Plantas/químicaRESUMEN
Two new lignans (1-2), along with five known compounds (3-7) with different structures were isolated from leaves and twigs of Cleistanthus concinnus Croizat. The new lignans were elucidated as (7'R,8'S)-3,3',5'-trimethoxy-4,4'-dihydroxy-7-en-7',9- epoxy-8,8'-lignan (1) and (7'R,8'S)-3,3'-dimethoxy-4,4'-dihydroxy-7-en-7',9-epoxy-8, 8'-lignan (2) by comprehensive spectroscopic analysis including 1D and 2D NMR as well as HREIMS and comparing their NMR data with known compounds in the literature. Among these isolated compounds, compound 1, 2, 3, and 6 were tested for anti- inflammatory effects by inhibiting NO production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. Compound 1, 2, and 6 exhibit NO inhibitory activity.[Formula: see text].
Asunto(s)
Euphorbiaceae/química , Lignanos/química , Lignanos/farmacología , Animales , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/farmacología , China , Evaluación Preclínica de Medicamentos , Lipopolisacáridos/farmacología , Espectroscopía de Resonancia Magnética , Ratones , Estructura Molecular , Óxido Nítrico/metabolismo , Hojas de la Planta/química , Células RAW 264.7RESUMEN
Two new sesquiterpenoids were isolated from Stellera chamaejasme L., known as the traditional Chinese herb 'Rui Xiang Lang Du'. The compounds were elucidated as stelleraguaianone B (1) and C (2) by comprehensive spectroscopic analysis, including 1D and 2D NMR as well as HRESIMS, and by comparing their NMR data with known compounds. In addition, the structure of 1 was further confirmed by single-crystal X-ray diffraction analysis. Both the compounds were evaluated for their cytotoxicity on common tumour cell lines in vitro, which revealed that compound 1 exhibits cytotoxic activity on A549 cells, while 2 has no activity.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Sesquiterpenos/farmacología , Thymelaeaceae/química , Células A549 , Antineoplásicos Fitogénicos/aislamiento & purificación , Línea Celular Tumoral , China , Humanos , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Plantas Medicinales/química , Sesquiterpenos/aislamiento & purificaciónRESUMEN
Two new 6-norpolycyclic polyprenylated acylphloroglucinols (PPAPs), hypermonins A (1) and B (2), featuring an undescribed decahydroindeno[1,7-bc]furan ring system, were isolated from the leaves and twigs of Hypericum monogynum. These compounds are a pair of epimers with opposite configurations at the C-5 position. Their structures, including their absolute configurations, were determined by extensive spectroscopic analysis and electronic circular dichroism (ECD) calculations. A plausible biosynthetic pathway of 1 and 2 was also proposed. Compound 1 exhibited a significant protective effect against corticosterone-induced injury in PC12 cells.
Asunto(s)
Hemiterpenos/farmacología , Compuestos Heterocíclicos con 3 Anillos/farmacología , Hypericum/química , Fármacos Neuroprotectores/farmacología , Floroglucinol/análogos & derivados , Floroglucinol/farmacología , Animales , Línea Celular Tumoral , Hemiterpenos/química , Hemiterpenos/aislamiento & purificación , Compuestos Heterocíclicos con 3 Anillos/química , Compuestos Heterocíclicos con 3 Anillos/aislamiento & purificación , Modelos Químicos , Fármacos Neuroprotectores/química , Fármacos Neuroprotectores/aislamiento & purificación , Floroglucinol/química , Floroglucinol/aislamiento & purificación , Hojas de la Planta/química , Ratas , EstereoisomerismoRESUMEN
Four new indole alkaloids, melodinusines A-D (1, 2, 6, and 7), along with 26 known indole alkaloids, were isolated from Melodinus tenuicaudatus and Melodinus khasianus (Melodinus genus). Among them, 1 and 2 are aspidospermine-aspidospermine-type bisindole alkaloids while 7 is a novel melodinus-type alkaloid. Their structures were established on the basis of comprehensive spectroscopic data analysis and the structure of 7 was further confirmed by single-crystal X-ray diffraction analysis. Their cytotoxic activities against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7, and SW480 were also evaluated.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Apocynaceae/química , Alcaloides Indólicos/aislamiento & purificación , Quinolinas/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Frutas/química , Humanos , Alcaloides Indólicos/farmacología , Estructura Molecular , Componentes Aéreos de las Plantas/química , Quinolinas/farmacologíaRESUMEN
Rare ent-abietane-rosane diterpenoid heterodimers, Bisebracteolasins A and B (1 and 2, respectively), were isolated from the roots of Euphorbia ebracteolata Hayata. Their structures and absolute configurations were elucidated from spectroscopic data and X-ray diffraction analysis. Compounds 1 and 2 exhibited moderate cytotoxic effects against five cancer cell lines. Compound 1 showed more effective antiproliferative activities against human tumour cells, HL-60 and SMMC-7721, with IC50 values of 2.61 and 4.08 µM, respectively, than 2. Both compounds 1 and 2 inhibit the colorectal cancer stem cell line P6C with IC50 values of 16.48 and 34.76 µM, respectively. Moreover, preliminary biological tests showed compound 1 exhibited inhibitory activity towards tumoursphere formation and migration of the P6C cell line. Overall, we identified two novel diterpenoid heterodimers, and Bisebracteolasin A exhibits therapeutic potential in impeding tumour growth and metastatic ability of cancer stem cells.
Asunto(s)
Antineoplásicos Fitogénicos/farmacología , Diterpenos/farmacología , Antineoplásicos Fitogénicos/química , Línea Celular Tumoral , Movimiento Celular/efectos de los fármacos , Proliferación Celular/efectos de los fármacos , Diterpenos/química , Evaluación Preclínica de Medicamentos , Euphorbia/química , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/química , Extractos Vegetales/farmacología , Raíces de Plantas/química , Relación Estructura-ActividadRESUMEN
(+)-Perforison A and (-)-perforison A, a new pair of chromone enantiomers, along with four known compounds, were isolated from the leaves and stems of Harrisonia perforata. Their structures and absolute configurations were determined on the basis of extensive analysis of spectroscopic data and electronic circular dichroism (ECD) calculations. The cytotoxic activities in vitro of these compounds were evaluated, but none showed significant activity.
Asunto(s)
Cromonas/química , Simaroubaceae/química , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Dicroismo Circular , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Resultados Negativos , Hojas de la Planta/química , Tallos de la Planta/química , EstereoisomerismoRESUMEN
Four new Myrioneuron alkaloids, mysumamides A-D (1-4), along with three known ones were isolated from the twigs and leaves of Myrioneuron effusum. All of these alkaloids possessed the tetracyclic skeleton and contained the decahydroquinoline (cis-DHQ) moiety. Their structures and relative configurations were elucidated on the basis of spectroscopic methods, especially 2D NMR techniques. The absolute configuration of 1 was determined by single-crystal X-ray diffraction. The cytotoxic activities of these compounds were also evaluated in vitro.
Asunto(s)
Alcaloides/química , Quinolinas/química , Rubiaceae/química , Alcaloides/aislamiento & purificación , Cristalografía por Rayos X , Estructura Molecular , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Hojas de la Planta/química , Quinolinas/aislamiento & purificaciónRESUMEN
Fourteen new limonoids, munronins A-N (1-14), and eight known limonoids (15-22) were isolated from the whole plants of Munronia henryi. The structures of the new compounds were elucidated by 2D NMR spectroscopy and mass spectrometry, and the structure of 8 was confirmed by single-crystal X-ray diffraction analysis. Compound 1 represents the first limonoid found with a novel 7-oxabicyclo[2.2.1]heptane moiety produced by incorporating C-11 and C-14 via an oxygen atom. All compounds were evaluated for their anti-tobacco mosaic virus (TMV) activity and in vitro cytotoxicity against the human cancer HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cell lines. Among them, compounds 2, 8, 9, 10, 11, 12, 18, and 20 showed significant anti-TMV activity, with IC50 values in the range 19.6-44.4 µg/mL. Compounds 1 and 18 exhibited cytotoxic effects for all five cancer cell lines, with IC50 values between 0.4 and 4.8 µM.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Antivirales/aislamiento & purificación , Antivirales/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Limoninas/aislamiento & purificación , Limoninas/farmacología , Meliaceae/química , Virus del Mosaico del Tabaco/efectos de los fármacos , Antineoplásicos Fitogénicos/química , Antivirales/química , Cristalografía por Rayos X , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Células HL-60 , Humanos , Concentración 50 Inhibidora , Limoninas/química , Conformación Molecular , Estructura Molecular , Resonancia Magnética Nuclear BiomolecularRESUMEN
Spiramine C-D, the atisine-type diterpenoid alkaloids isolated from the Chinese herbal medicine Spiraea japonica complex, are shown to have anti-inflammatory effects in vitro. In this study, we report that spiramine derivatives of spiramine C-D bearing α,ß-unsaturated ketone induce apoptosis of Bax(-/-)/Bak(-/-) MEFs cell, which is positively corresponding their cytotoxicity of tumor cell lines including multidrug resistance MCF-7/ADR. The results indicated that oxazolidine ring is necessary, and derivatives bearing double 'Michael reaction acceptor' group would significantly increased activities both of inducing apoptosis of Bax(-/-)/Bak(-/-) cells and cytotoxicity of tumor cells. The result indicated that spiramine derivative with α,ß-unsaturated ketone group is a new anti-cancer agent with a capability of inducing apoptosis of cancer cells in Bax/Bak-independent manner.
Asunto(s)
Apoptosis/efectos de los fármacos , Compuestos Heterocíclicos de 4 o más Anillos/química , Compuestos Heterocíclicos de 4 o más Anillos/farmacología , Proteína Destructora del Antagonista Homólogo bcl-2/efectos de los fármacos , Proteína X Asociada a bcl-2/efectos de los fármacos , Antineoplásicos/química , Antineoplásicos/farmacología , Línea Celular Tumoral , Eliminación de Gen , Humanos , Concentración 50 Inhibidora , Estructura Molecular , Spiraea/química , Proteína Destructora del Antagonista Homólogo bcl-2/genética , Proteína X Asociada a bcl-2/genéticaRESUMEN
Eight new aphanamixoid-type aphanamixoids (C-J, 1-8) and six new prieurianin-type limonoids, aphanamixoids K-P (9-14), along with 10 known terpenoids were isolated from Aphanamixis polystachya, and their structures were established by spectroscopic data analysis. Among the new limonoids, 13 compounds exhibited antifeedant activity against the generalist Helicoverpa armigera, a plant-feeding insect, at various concentration levels. In particular, compounds 1, 4, and 5 showed potent activities with EC50 values of 0.017, 0.008, and 0.012 µmol/cm(2), respectively. On the basis of a preliminary structure-activity relationship analysis, some potential active sites in the aphanamixoid-type limonoid molecules are proposed.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Conducta Alimentaria/efectos de los fármacos , Limoninas/aislamiento & purificación , Limoninas/farmacología , Meliaceae/química , Algoritmos , Animales , Antineoplásicos Fitogénicos/química , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/química , Células HL-60 , Humanos , Larva/efectos de los fármacos , Lepidópteros/efectos de los fármacos , Limoninas/química , Estructura Molecular , Mariposas Nocturnas/efectos de los fármacos , Resonancia Magnética Nuclear Biomolecular , Spodoptera/fisiología , Relación Estructura-ActividadRESUMEN
Two new sphingolipids, pipercerebrosides A (1) and B (2), were isolated from the leaves of Piper betle L. Their structures, including absolute configurations, were determined by spectroscopic analysis and chemical degradation. These two compounds did not show significant cytotoxic activity against the cancer cell lines K562 and HL-60 in a MTT assay.
Asunto(s)
Medicamentos Herbarios Chinos/química , Piper betle/química , Hojas de la Planta/química , Esfingolípidos/química , Ensayos de Selección de Medicamentos Antitumorales , Medicamentos Herbarios Chinos/aislamiento & purificación , Medicamentos Herbarios Chinos/farmacología , Células HL-60 , Humanos , Células K562 , Metilación , Estructura Molecular , Oxidación-Reducción , Esfingolípidos/aislamiento & purificación , Esfingolípidos/farmacologíaRESUMEN
AIM: To study the Amaryllidaceae alkaloids of the bulbs of Lycoris radiata. METHODS: The chemical constituents were isolated and purified by various chromatographic techniques, and the chemical structures were elucidated on the basis of spectroscopic methods. In addition, the antiviral activities of alkaloids 1-10 were evaluated using flu virus A. RESULTS: One new homolycorine-type alkaloid 2α-methoxy-6-O-ethyloduline (1), together with nine known alkaloids 2α-methoxy-6-O-methyloduline (2), trispherine (3), 8-O-demethylhomolycorine (4), homolycorine (5), 9-O-demethylhomolycorine (6), oduline (7), lycorenine (8), 6α-O-methyllycorenine (9) and O-ethyllycorenine (10) were obtained. CONCLUSION: Alkaloid 1 is a new compound, and 1-3 were major alkaloids in this plant. Alkaloids 1-3 showed weak antiviral activities against flu virus A with IC50 values of 2.06, 0.69, and 2.71 µg·mL-1 and CC50 values of 14.37, 4.79, and 80.12 µg·mL-1, respectively.