RESUMO
Eight new complex flavanones with a novel linkage, cryptoyunnanones A-H (1-8), together with four known α-pyrones, were isolated from the leaves and twigs of Cryptocarya yunnanensis. The structures of 1-8 including their absolute configurations were characterized by spectroscopic data analysis and single-crystal X-ray crystallography. Plausible biosynthetic pathways for the formation of compounds 1-8 were proposed. Compounds 1-4 exhibited cytotoxicity against HCT-116, MDA-MB-231, and PC-3 cancer cells with IC50 values from 6.4 to 9.1 µM.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Cryptocarya/química , Flavanonas/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , China , Ensaios de Seleção de Medicamentos Antitumorais , Flavanonas/isolamento & purificação , Humanos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Pironas/isolamento & purificaçãoRESUMO
Eleven new iridoids, brachybones A-K (1-11), were isolated from the twigs of Viburnum brachybotryum. Their structures including absolute configurations were determined by spectroscopic data analysis and from the electronic circular dichroism (ECD) spectra. All of the compounds 1-11 possess one or two acetoxysenecioate substituents. Furthermore, compounds 5-7 and 11 feature a Cl atom in the molecule, while compounds 9-11 exhibit a cagelike rigid skeleton through an unusual oxo bridge from C-3 to C-8 or C-10. The isolates were evaluated for cytotoxic activity against the HCT-116, A549, and Hela cell lines, and the results showed compounds 10 and 11 to be active against HCT-116 cells.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Iridoides/farmacologia , Viburnum/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , China , Humanos , Iridoides/isolamento & purificação , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologiaRESUMO
Two biphenyl-type neolignans with a rare dibenzofuran skeleton, including a new one piyunneolignan A (1) and a known one piperneolignan D (2), together with a new sesquiterpenoid piyunin A (3), were isolated from the leaves and twigs of Piper yunnanense. Their structures were established on the basis of comprehensive spectroscopic data analysis and electronic circular dichroism (ECD) calculation. Piyunneolignan A (1) featured a rare C-2-C-2'/C-3-O-C-3' linkage. Compounds 1-3 were evaluated for their antimicrobial and cytotoxic activities against a panel of bacteria, fungi, and human cancer cell lines, respectively.
Assuntos
Lignanas/isolamento & purificação , Piper/química , Sesquiterpenos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Lignanas/química , Estrutura Molecular , Sesquiterpenos/químicaRESUMO
Two new prenylated acetophenone derivatives racemates, meliviticines A (1) and B (2) with unprecedented rearranged skeletons, were isolated from Melicope viticina. Subsequent chiral resolution led to the separation of two pairs of enantiomers, (±)-meliviticines A (1a/1b) and (±)-meliviticines B (2a/2b). Their structures including absolute configurations were elucidated by extensive spectroscopic data, electronic circular dichroism analysis, and X-ray crystallography. A plausible biosynthetic pathway of 1 and 2, involving ring cleavage and rearrangement of the prenylated acetophenone backbone was proposed. All the isolates showed moderate antimicrobial activities with MIC values of 25-50⯵g/mL against several bacterial and fungal strains.
Assuntos
Acetofenonas/química , Anti-Infecciosos/farmacologia , Bactérias/efeitos dos fármacos , Benzofuranos/farmacologia , Fungos/efeitos dos fármacos , Extratos Vegetais/farmacologia , Folhas de Planta/química , Rutaceae/química , Anti-Infecciosos/química , Benzofuranos/química , Estrutura Molecular , Prenilação , EstereoisomerismoRESUMO
Five new α-pyrone derivatives, cryptoyunnanes A - E (1 - 5), together with four known analogues, were isolated from the leaves and twigs of Cryptocarya yunnanensis. Their structures including absolute configurations were elucidated by extensive spectroscopic data and electronic circular dichroism (ECD) analyses. Compounds 4 and 6 showed significant cytotoxicity against A549, HCT-116, MDA-MB-231, PC-3 and HeLa with IC50 values from 2.25 to 8.97 µM. Compounds 1, 2 and 7 also displayed good cytotoxicity against HCT-116, MDA-MB-231 and PC-3 with IC50 values from 1.26 to 8.32 µM. This is the first time to report the isolation and bioactivity evaluation of chemical constituents from C. yunnanensis.
Assuntos
Antineoplásicos , Cryptocarya , Antineoplásicos/química , Cryptocarya/química , Estrutura Molecular , Folhas de Planta/química , Pironas/químicaRESUMO
Fourteen new geranyl phenyl ethers (1-14) along with three known compounds (15-17) were isolated from Illicium micranthum, and their structures were elucidated by comprehensive spectroscopic methods. Illimicranins A-H (1-8) were characterized as geranyl vanillin ethers, while 9 and 10 were dimethyl acetal derivatives. Illimicranins I and J (11 and 12) were rare geranyl isoeugenol ethers. Illimicranins K and L (13 and 14) represented the first example of geranyl guaiacylacetone ether and geranyl zingerone ether, respectively. Compounds 1, 2 and 15 exhibited anti-HBV (hepatitis B virus) activity against HBsAg (hepatitis B surface antigen) and HBeAg (hepatitis B e antigen) secretion, and HBV DNA replication.
Assuntos
Illicium , Antivirais/química , Antivirais/farmacologia , Antígenos de Superfície da Hepatite B , Antígenos E da Hepatite B , Illicium/química , Éteres FenílicosRESUMO
In the aim to evaluate the functional food property of Cinnamomum bejolghota, seven new lignans and neolignans, bejolghotins A-G (1-4 and 9-11), along with 14 known ones (5-8 and 12-21), were isolated and their structures including absolute configurations were elucidated by extensive spectroscopic data and electronic circular dichroism (ECD) analyses. All of the isolates were tested for antioxidant and human cancer cell proliferation inhibitory activities. Twenty compounds showed comparable antioxidant activity to the positive controls, and three significantly inhibited the growth of three cancer cell lines HCT-116, A549, and MDA-MB-231 with IC50 values of 0.78-2.93 µM, which confirmed its health benefits.
Assuntos
Antioxidantes/farmacologia , Cinnamomum/química , Alimento Funcional/análise , Inibidores do Crescimento/farmacologia , Lignanas/farmacologia , Neoplasias/fisiopatologia , Extratos Vegetais/farmacologia , Antioxidantes/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Inibidores do Crescimento/química , Humanos , Lignanas/química , Estrutura Molecular , Extratos Vegetais/químicaRESUMO
Two new spiroketal derivatives with an unprecedented amino group, 2'-aminodechloromaldoxin (1) and 2'-aminodechlorogeodoxin (2), along with one known analogue dechloromaldoxin (3), were isolated from the plant endophytic fungus Pestalotiopsis flavidula. Their structures were elucidated on the basis of extensive spectroscopic analysis. The purification was cytotoxicity-guided which indicated the extract, fractions and compounds were evaluated in vitro for anti-proliferative activity against a panel of human cancer cell lines. The results showed compounds 1 and 2 with moderate cytotoxicity while 3 was inactive, which suggested -NH2 group might play a very important role for their cytotoxicity. This is the first study for P. flavidula and the first time to report the spiroketal derivatives as alkaloids from the Pestalotiopsis genus.
Assuntos
Alcaloides/farmacologia , Furanos/farmacologia , Compostos de Espiro/farmacologia , Xylariales/química , Alcaloides/química , Alcaloides/isolamento & purificação , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Furanos/química , Furanos/isolamento & purificação , Humanos , Estrutura Molecular , Compostos de Espiro/química , Compostos de Espiro/isolamento & purificaçãoRESUMO
Three new arylalkenyl α,ß-unsaturated δ-lactones, cryptobrachytones A-C (1-3), together with one known analogue kurzilactone (4), were isolated from the leaves and twigs of Cryptocarya brachythyrsa. Their structures were elucidated based on extensive spectroscopic data and electronic circular dichroism (ECD) analysis. All the isolates were evaluated in vitro for anti-proliferative activity against a panel of five human cancer cell lines and one human normal cell, respectively, and the results showed 1, 2 and 4 possessing significant selective cytotoxicity toward the human cancer cell lines with IC50 values from 5.41 to 15.43⯵M. This is the first study for C. brachythyrsa.