RESUMO
Cytisine-pterocarpan-derived compounds were biomimetically synthesized with (-)-cytisine and (-)-maackiain via a N,N-4-dimethyl-4-aminopyridine (DMAP)-mediated synthetic strategy in a mild manner. In the present study, tonkinensine B (4) was elaborated in good and high yields with the optimized reaction conditions. The in vitro cytotoxicity of compound 4 was evaluated against breast cancer cell lines and showed that 4 had a better cytotoxicity against MDA-MB-231 cells (IC50 = 19.2 µM). Depending on the research on cytotoxicities of 4 against RAW 264.7 and BV2 cells, it was suggested that 4 produced low cytotoxic effects on the central nervous system. Further study indicated that 4 demonstrated cytotoxic activity against MDA-MB-231 cells and the cytotoxic activity was induced by apoptosis. The results implied that the apoptosis might be induced by mitochondrion-mediated apoptosis via regulating the ratio of Bax/Bcl-2 and promoting the release of cytochrome c from the mitochondrion to the cytoplasm in MDA-MB-231 cells.
Assuntos
Neoplasias da Mama/metabolismo , Citocromos c/metabolismo , Compostos Heterocíclicos com 2 Anéis/síntese química , Compostos Heterocíclicos com 2 Anéis/farmacologia , Mitocôndrias/metabolismo , Alcaloides/química , Animais , Azocinas/química , Mimetismo Biológico , Neoplasias da Mama/tratamento farmacológico , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Feminino , Compostos Heterocíclicos com 2 Anéis/química , Humanos , Células MCF-7 , Camundongos , Estrutura Molecular , Proteínas Proto-Oncogênicas c-bcl-2/metabolismo , Pterocarpanos/química , Quinolizinas/química , Células RAW 264.7 , Proteína X Associada a bcl-2/metabolismoRESUMO
A new coumarin, edgeworic acid (1), was isolated from the flower buds of Edgeworthia chrysantha, together with the five known coumarins umbelliferone (2), 5,7-dimethoxycoumarin (3), daphnoretin (4), edgeworoside C (5), and edgeworoside A (6). Their structures were established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift-correlated NMR pulse sequences (1H-1H COSY, HSQC and HMBC), in combination with acetylation reactions.
Assuntos
Cumarínicos/química , Flores/química , Thymelaeaceae/química , Acetilação , Cumarínicos/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Monossacarídeos/química , Monossacarídeos/isolamento & purificação , Raízes de Plantas/química , Umbeliferonas/química , Umbeliferonas/isolamento & purificaçãoRESUMO
The phytochemical investigation of extracts from the root barks of Lycium chinense yielded a new furolactone-type lignan, lyciumin (1). Its structure and absolute configurations were established on the basis of spectral data, particularly by the use of 1D NMR, 2D shift-correlated NMR pulse sequences ((1)H-(1)H COSY, HSQC, HMBC and ROESY) and CD spectra.
Assuntos
Lignanas/isolamento & purificação , Lycium/química , Medicamentos de Ervas Chinesas/química , Lignanas/química , Casca de Planta/química , Raízes de Plantas/químicaRESUMO
A new norlignan glycoside, named iso-agatharesinoside (2), and its aglycone, iso-agatharesinol (1), were isolated from the tuberous roots of Asparagus cochinchinensis. Their structures were established on the basis of spectral data, particularly by the use of 1D NMR and several 2D shift-correlated NMR pulse sequences (1H-1H COSY, HSQC, HMBC and ROESY).
Assuntos
Asparagus/química , Lignanas/química , Hidrólise , Lignanas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Raízes de Plantas/química , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
The phytochemical investigation of extracts from the radix of Angelica sinensis yielded a new phthalide dimer, 3,3'Z-6.7',7.6'-diligustilide, along with a known dimer, levistolide A. Their structures were established on the basis of spectral data, particularly using 1D-NMR and several 2D shift-correlated NMR pulse sequences (¹H-¹H COSY, HSQC, HMBC and NOESY).
Assuntos
Angelica sinensis/química , Benzofuranos/química , Dimerização , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Plantas Medicinais/químicaRESUMO
In the title compound, [CuCl2(C9H12N2O)], the Cu(II) atom is coordinated by two Cl- anions and two N atoms of one O-ethyl 3-methylpyridine-2-carboximidic acid molecule in a slightly distorted square-planar geometry, with Cu-N distances of 2.0483 (17) and 1.9404 (18) A, and Cu-Cl distances of 2.2805 (10) and 2.2275 (14) A. In addition, each Cu(II) atom is connected by one Cl- anion and the Cu(II) atom from a neighbouring molecule, with Cu...Cl and Cu...Cu distances of 2.9098 (13) and 3.4022 (12) A, respectively, and, therefore, a centrosymmetric dimer is formed. Adjacent molecular dimers are connected by pi-pi stacking interactions between pyridine rings to form a zigzag molecular chain. The molecular chains are also enforced by N-H...Cl and C-H...Cl interactions.