RESUMO
Twelve undescribed compounds including five sesquiterpenes (1-5), one monoterpene (6), and four lignans (7a/7b and 8a/8b), along with two other types (9 and 10) were isolated from the rhizomes of Atractylodes macrocephala. Among them, two pairs of enantiomers (7a/7b and 8a/8b) were successfully separated by chiral-phase HPLC, while racemate 9 could not be resolved. Their structures and absolute configurations were unambiguously elucidated by spectroscopic data analysis and electronic circular dichroism (ECD) calculations. Notably, compounds 1 and 2 are rare sesquiterpene hybrids featuring an eudesmanolactam linked to a resorcinol or methyl 2-methylpentanoat through a CN bond. Compound 3 represents the first example of eudesmanolide sesquiterpene with an oxygen-bridge between C-8 and C-14. Compounds 7a and 7b are a pair of rare enantiomeric benzodioxane norneolignans. Additionally, compound 2 exhibited weak cytotoxicity against SGC-7901 cells. Compound 4 significantly promoted the proliferation of LPS-induced IEC-6 cells with the rate of 117.2%.
Assuntos
Atractylodes , Lignanas , Sesquiterpenos , Estrutura Molecular , Atractylodes/química , Rizoma/química , Lignanas/farmacologia , Lignanas/química , Sesquiterpenos/químicaRESUMO
Five new 5,6-ß-epoxywithanolides (1-5) were isolated from the whole plants of Physalis minima L. Their structural elucidations were achieved by the extensive spectroscopic analysis (IR, UV, HR-ESI-MS, 1D-NMR, and 2D-NMR). The isolates were evaluated for their anti-inflammatory activities on lipopolysaccharide-induced nitric oxide production in RAW 264.7 cells and cytotoxic activities against three cancer cell lines, viz. A549 lung adenocarcinoma cells, SMMC-7721 hepatic carcinoma cells and MCF-7 breast cancer cells by using the MTT-based assay. All of them possessed moderate inhibition to the production of nitric oxide with IC50 values from 42.18 to 73.26 µM, and the IC50 values of the cytotoxic activities were in the range of 31.25 to 80.14 µM.
Assuntos
Anti-Inflamatórios/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Physalis/química , Vitanolídeos/farmacologia , Células A549 , Animais , Anti-Inflamatórios/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , China , Humanos , Células MCF-7 , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7 , Vitanolídeos/isolamento & purificaçãoRESUMO
The pericarp of Zanthoxylum bungeanum Maxim., commonly known as Sichuan pepper, is a widely used spice to remove fishy odor and add palatable taste. A phytochemical investigation of the 95% ethanol extract of Sichuan pepper resulted in the isolation of 21 isobutylhydroxyamides, including 8 new ones named ZP-amides G-N, among which the chiral resolution of racemic ZP-amide A and ZP-amide B was successfully accomplished. The protective activity on corticosterone-treated PC12 cells of the isolated isobutylhydroxyamides was also evaluated. The new compounds 3-5 and the known compounds 1, 1a, 2, 2a, 11, and 15 improved the survival rate of PC12 cells. The bioactivity studies disclosed the potential of Sichuan pepper to be developed as new neuroprotective functional food.
Assuntos
Amidas/farmacologia , Butanos/farmacologia , Corticosterona/toxicidade , Fármacos Neuroprotetores/farmacologia , Extratos Vegetais/farmacologia , Zanthoxylum/química , Amidas/química , Animais , Butanos/química , Sobrevivência Celular/efeitos dos fármacos , Neurônios/citologia , Neurônios/efeitos dos fármacos , Fármacos Neuroprotetores/química , Células PC12 , Extratos Vegetais/química , RatosRESUMO
The present study was designed to investigate the chemical constituents of the whole herb of Dichrocephala benthamii. A new megastigmane glucoside (compound 1), together with its four known analogues (compounds 2-5), was obtained. Their structures were elucidated on the basis of spectroscopic analyses (UV, IR, MS, and 1D and 2D NMR). The absolute configuration of compound 1 was assigned on the basis of CD method and chemical evidence. In addition, their cytotoxicity against human hepatoma cells (HepG-2) was evaluated by the MTT method. Compound 5 showed weak activity against HepG-2, while the other compounds did not show remarkable inhibitory effects.
Assuntos
Asteraceae/química , Cicloexanonas/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Glucosídeos/isolamento & purificação , Norisoprenoides/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , China , Cicloexanonas/química , Cicloexanonas/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Glucosídeos/química , Glucosídeos/farmacologia , Células Hep G2 , Humanos , Estrutura Molecular , Norisoprenoides/química , Norisoprenoides/farmacologia , Plantas MedicinaisRESUMO
Two new unsaturated fatty acids, (Z)-octadec-13-en-11-ynoic acid (1) and (Z)-octadec-16-en-12,14-diynoic acid (2), along with six known compounds were isolated from the whole plant of Pothos chinensis. The structures of these compounds were elucidated by detailed spectroscopic analysis, including 1D and 2D NMR data. Compound 2 showed moderate antibacterial activity against Staphylococcus aureus.
Assuntos
Antibacterianos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Ácidos Graxos Insaturados/isolamento & purificação , Antibacterianos/química , Antibacterianos/farmacologia , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Ácidos Graxos Insaturados/química , Ácidos Graxos Insaturados/farmacologia , Células Hep G2 , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Staphylococcus aureus/efeitos dos fármacos , EstereoisomerismoRESUMO
Eight highly oxygenated germacranolides (1-8) including four new ones (2-5) were isolated from the whole plant of Carpesium divaricatum. The planar structures and relative configurations of the new compounds were determined by NMR experiment and HRESIMS data. The absolute configuration of 1 was established by circular dichroism (CD) method and X-ray diffraction, and the stereochemistry of the new compounds 2-5 were determined by similar CD spectra with 1. Compound 2 is the first hydroperoxyl germacrane from the genus Carpesium. The (13)C NMR data of 1, NMR data of 6-7, and their absolute configurations were reported for the first time. Two new compounds (2 and 4) and two known compounds (6 and 8) exhibited potent cytotoxicity against human cervical cancer (HeLa) cells, superior to that of the positive control doxorubicin.