RESUMEN
Two new clerodane diterpenoids (1 and 2), a new pyran-2-one derivative (3), along with five known compounds (4â8), were isolated from Croton crassifolius. Notably, crassifolin X (1) is a novel clerodane diterpenoid, characterized with a peculiar δ-lactone core being formed between C-1 and C-4. Their structures, including absolute configurations, were established on the basis of spectroscopic methods (UV, IR, HRESIMS and NMR), and circular dichroism experiments. In addition, all compounds were evaluated for their anti-neuroinflammatory activities based on the expression of TNF-α and IL-6 levels on LPS-induced BV2 cells, and compounds 1â3 and 5 showed potential anti-neuroinflammatory activity.
Asunto(s)
Croton , Diterpenos de Tipo Clerodano , Diterpenos , Croton/química , Diterpenos/química , Diterpenos de Tipo Clerodano/química , Diterpenos de Tipo Clerodano/farmacología , Estructura Molecular , Raíces de Plantas/química , Piranos/análisisRESUMEN
Eight new stilbene dimer xylosides (1-8) and one new flavanol (9), along with seven known ones (10-16) were isolated from the roots of Lysidice rhodostegia. Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HR-ESI-MS, 1D and 2D NMR), ECD calculations and acid hydrolysis. Compounds 1-16 were evaluated for their antioxidant activities using DPPH radical-scavenging assay. Especially, compounds 9 and 10 exhibited stronger antioxidant effects than the positive control (vitamin E), with IC50 values of 9.57 ± 1.30 and 13.60 ± 1.47 µM, respectively.
Asunto(s)
Antioxidantes/farmacología , Fabaceae/química , Glicósidos/farmacología , Polifenoles/farmacología , Estilbenos/farmacología , Antioxidantes/aislamiento & purificación , China , Glicósidos/aislamiento & purificación , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Raíces de Plantas/química , Polifenoles/aislamiento & purificación , Estilbenos/aislamiento & purificaciónRESUMEN
Five matrine-type alkaloids (1â5) including two new compounds (1 and 3) and a new natural product (2) were isolated from the roots of Sophora tonkinesis. Their structures were identified by extensive spectroscopic analysis (UV, IR, HRESIMS and NMR). The absolute configurations of 2 and 3 were determined by X-ray diffraction. Compounds 1â5 were evaluated their activity against inflammatory cytokines TNF-α and IL-6 levels on LPS-induced RAW 264.7 macrophages, and compound 1 showed the most significant activity, potent than that of matrine, the representative ingredient from Sophora plants.
Asunto(s)
Alcaloides/farmacología , Antiinflamatorios/química , Quinolizinas/farmacología , Sophora/química , Alcaloides/química , Animales , China , Espectroscopía de Resonancia Magnética , Ratones , Estructura Molecular , Raíces de Plantas/química , Células RAW 264.7 , MatrinasRESUMEN
Two new isoquinoline alkaloids, 6 R,6aS-N-nantenine Nß-oxide (1), 6S,6aS-N-nantenine Nα-oxide (2), along with nine known alkaloids, nantenine (3), oxonantenine (4), protopine (5), nornantenine (6), N-methyl-laurotetanine (7), isocorydine (8), O-methyflavinantine (9), N-methyl-2,3,6-trimethoxymorphinan-dien-7-one Nß-oxide (10) and (+)-10-O-methylhernovine Nß-oxide (11) were isolated from the seeds of Nandina domestica. Their structures were elucidated by extensive analyses of spectroscopic data (IR, UV, HRESIMS, 1 D and 2 D NMR), ECD calculation and comparison with the related literatures. In addition, the cytotoxicity against A549 cells of these alkaloids was determined by the MTT assay.
Asunto(s)
Alcaloides , Berberidaceae , Isoquinolinas/farmacología , Células A549 , Alcaloides/aislamiento & purificación , Alcaloides/farmacología , Berberidaceae/química , Humanos , Isoquinolinas/aislamiento & purificación , Estructura Molecular , Fitoquímicos/aislamiento & purificación , Fitoquímicos/farmacología , Extractos Vegetales , Semillas/químicaRESUMEN
Pegaharines A-G (1-6), six novel ß-carboline alkaloids representing three types of skeleton, were isolated from the seeds of Peganum harmala. Compound 1 is a peculiar ß-carboline alkaloid characterized by the unprecedented carbon skeleton of an azepine-indole system. Compounds 3-6 represent the first examples of heterodimers constructed from rare tetracyclic ß-carboline and classic tricyclic ß-carboline alkaloids. Compounds 1 and 2 were characterized by X-ray crystallography. Compound 4 exhibited strong antiviral activity against HSV-2, with an IC50 value of 2.12 ± 0.14 µM.
Asunto(s)
Alcaloides/química , Antivirales/farmacología , Carbolinas/química , Herpesvirus Humano 2/efectos de los fármacos , Peganum/química , Extractos Vegetales/química , Antivirales/química , Herpesvirus Humano 2/química , Estructura Molecular , Semillas/químicaRESUMEN
Seven sesquiterpene lactones, 8-O-methacryloylelephanpane, 2,4-bis-O-methyl-8-O-methacryloylelephanpane, 4-O-ethyl-8-O-methacryloylelephanpane, 8-O-methacryloylisoelephanpane, 2-O-demethyltomenphantopin C, molephantin A, molephantin B, along with ten known ones, were isolated from Elephantopus mollis (Asteraceae). Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HRESIMS, 1D and 2D NMR). The isolates were evaluated for their anti-inflammatory activities on LPS-stimulated RAW 264.7 cells, and all tested compounds exhibited potent anti-inflammatory effects with IC50 values of 0.57 ± 0.17 to 14.34 ± 1.61 µM, except that compound tomenphantopin C exhibited moderate anti-inflammatory activity with IC50 values of 59.97 ± 1.53 µM.
Asunto(s)
Antiinflamatorios/química , Asteraceae/química , Sesquiterpenos/química , Animales , Antiinflamatorios/aislamiento & purificación , Ratones , Estructura Molecular , Extractos Vegetales/química , Células RAW 264.7 , Sesquiterpenos/aislamiento & purificaciónRESUMEN
Five new diterpenoid alkaloids, ajacisines A-E (1-5), were isolated from Delphinium ajacis, along with seven known alkaloids (6-12). On the basis of their spectral data (IR, UV, HR-ESI-MS, 1D and 2D NMR) and chemical properties, the structures of compounds 1-12 were identified. All isolated compounds were evaluated for their in vitro antiviral activities against respiratory syncytial virus, and compounds 3-5 and 8 exhibited moderate to weak effects with IC50 values of 75.2 ± 1.1, 35.1 ± 0.6, 10.1 ± 0.3, and 50.2 ± 0.5 µM, respectively.
Asunto(s)
Alcaloides/farmacología , Antivirales/farmacología , Delphinium/química , Diterpenos/farmacología , Estructura Molecular , Virus Sincitial Respiratorio Humano/efectos de los fármacos , Alcaloides/química , Alcaloides/aislamiento & purificación , Antivirales/química , Antivirales/aislamiento & purificación , Línea Celular Tumoral , Diterpenos/química , Diterpenos/aislamiento & purificación , Humanos , Espectroscopía de Resonancia Magnética , Raíces de Plantas/química , Tallos de la Planta/químicaRESUMEN
Seven new phloroglucinol derivatives (1-7) were isolated from the fruit tree Syzygium jambos together with four known triterpenoids (8-11) and two known flavones (12 and 13). According to the spectroscopic analyses (infrared, electrospray ionization mass spectrometry (ESIMS), high-resolution ESIMS, 1D and 2D nuclear magnetic resonance), the structures of compounds 1-7 were elucidated as jambone A (1), jambone B (2), jambone C (3), jambone D (4), jambone E (5), jambone F (6), and jambone G (7). All the isolates were determined for their cytotoxic activities on melanoma cells by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, and compounds 10 and 11 showed potent activities. Moreover, compounds 1, 2, 4-7, 12, and 13 exhibited weak antioxidant activities under ferric-reducing antioxidant power and 2,2-diphenyl-1-picryhydrazyl radical-scavenging assays.
Asunto(s)
Floroglucinol/química , Extractos Vegetales/química , Syzygium/química , Frutas/química , Estructura Molecular , Floroglucinol/toxicidad , Extractos Vegetales/toxicidadRESUMEN
Six new prenylated acetophenone derivatives were isolated from the leaves of Acronychia oligophlebia. The chemical structures of them were elucidated by extensive analysis of spectroscopic data (IR, UV, HRESIMS, 1D and 2D NMR). The cytotoxic activity of the isolates was evaluated against MCF-7 cells. Among these compounds, 2 and 6 exhibited mild cytotoxic activity with IC50 values of 33.5 and 25.6 µM, respectively.