RESUMO
Nine new alkaloids of the koumine (1-4), humantenine (5-7), and yohimbane (8, 9) types as well as 12 known analogues were isolated from the leaves and vine stems of Gelsemium elegans. Compound 1 is the first N-4-demethyl alkaloid of the koumine type, compound 7 is the first nor-humantenine alkaloid, and compounds 8 and 9 are the first N-1-oxide and the first seco-E-ring alkaloids, respectively, of the yohimbane type. Compounds 1 and 7 exhibited moderate cytotoxicity against five human tumor cell lines with IC50 values in the range 4.6-9.3 µM.
Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Óxidos N-Cíclicos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Gelsemium/química , Alcaloides de Triptamina e Secologanina/isolamento & purificação , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Óxidos N-Cíclicos/química , Óxidos N-Cíclicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Alcaloides Indólicos/química , Alcaloides Indólicos/isolamento & purificação , Alcaloides Indólicos/farmacologia , Concentração Inibidora 50 , Lipopolissacarídeos , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Óxido Nítrico/biossíntese , Ressonância Magnética Nuclear Biomolecular , Folhas de Planta/química , Caules de Planta/química , Alcaloides de Triptamina e Secologanina/química , Alcaloides de Triptamina e Secologanina/farmacologiaRESUMO
Four new biphenyl and biphenyl ether quinolizidine N-oxide alkaloids, 5- EPI-dihydrolyfoline N-oxide (1), decamine N-oxide (2), lagerstroemine N-oxide (3), and lagerine N-oxide (4), were isolated from the aerial parts of Lagerstroemia indica, and their structures were established by extensive spectroscopic studies. In addition, the inhibitory effects of isolated compounds on rat lens aldose reductase (RLAR) were examined.
Assuntos
Alcaloides/química , Compostos de Bifenilo/química , Óxidos N-Cíclicos/química , Lagerstroemia/química , Quinolizidinas/química , Aldeído Redutase/efeitos dos fármacos , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Animais , Compostos de Bifenilo/isolamento & purificação , Compostos de Bifenilo/farmacologia , Fracionamento Químico , Óxidos N-Cíclicos/isolamento & purificação , Óxidos N-Cíclicos/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Inibidores Enzimáticos/farmacologia , Éteres/química , Espectroscopia de Ressonância Magnética , Componentes Aéreos da Planta/química , Quinolizidinas/isolamento & purificação , Quinolizidinas/farmacologia , Ratos , Ratos Sprague-DawleyRESUMO
Two new morphinane alkaloids, 1-hydroxy-10-oxo-sinomenine (1) and 4,5-epoxy-14-hydroxy sinomenine N-oxide (2), have been isolated from the stems of Sinomenium acutum. Their structures were established by various spectral analyses, especially 2D NMR experiments. The structure of 2 was confirmed by single crystal X-ray diffraction. The absolute configurations of 1 and 2 were deduced by comparison of CD spectra with the known alkaloid sinomenine (3). Compound 1 was tested for DPPH inhibition and gave IC(50) of 27.9 µM. Compound 2 was tested for neuroprotective effect and showed significant activity against ß-amyloid(25-35)-induced oxidative injury (*P < 0.05) at 10 µM in PC-12 cells.
Assuntos
Alcaloides/isolamento & purificação , Óxidos N-Cíclicos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Morfinanos/isolamento & purificação , Fármacos Neuroprotetores/isolamento & purificação , Alcaloides/química , Alcaloides/farmacologia , Animais , Compostos de Bifenilo/farmacocinética , Óxidos N-Cíclicos/química , Óxidos N-Cíclicos/farmacologia , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Estrutura Molecular , Morfinanos/química , Morfinanos/farmacologia , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/farmacologia , Ressonância Magnética Nuclear Biomolecular , Células PC12 , Picratos/farmacocinética , Caules de Planta/química , Ratos , Sinomenium/química , Difração de Raios XRESUMO
Tetramic acid derivatives are an important class of nitrogen heterocycles with a pyrrolidine-2,4-dione core as a key structural motif. From the sponge-derived fungus Beauveria bassiana, a new equisetin-like tetramic acid derivative, beauversetin (1), was isolated. The sea weed-derived fungus Microdiplodia sp. produced the tetramic acid derivative 2 (Sch210972) which was shown to inhibit human leucocyte elastase (HLE) with an IC50 of 1.04 microg mL(-1).
Assuntos
Óxidos N-Cíclicos/análise , Óxidos N-Cíclicos/isolamento & purificação , Hypocreales/química , Poríferos/microbiologia , Pirrolidinonas/análise , Pirrolidinonas/isolamento & purificação , Animais , Óxidos N-Cíclicos/toxicidade , Elastase de Leucócito/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Pirrolidinonas/química , Pirrolidinonas/toxicidadeRESUMO
To screen the anti-tumor effects of the four alkaloids: brucine, strychnine, brucine N-oxide and isostrychnine from the seed of Strychnos nux-vomica, MTT assay was used to examine the growth inhibitory effects of these alkaloids on human hepatoma cell line (HepG2). Brucine, strychnine and isostrychnine revealed significant inhibitory effects against HepG2 cell proliferation, whereas brucine N-oxide didn't have such an effect. In addition, brucine caused HepG2 cell shrinkage, membrane blebbing, apoptotic body formation, all of which are typical characteristics of apoptotic programmed cell death. The results of flow cytometric analysis demonstrated that brucine caused dose-dependent apoptosis of HepG2 cells through cell cycle arrest at G0/G1 phase, thus preventing cells entering S or G2/M phase. Immunoblot results revealed that brucine significantly decreased the protein expression level of cyclooxygenase-2, whereas increased the expression caspase-3 as well as the caspase-3-like protease activity in HepG2 cells, suggesting the involvement of cyclooxygenase-2 and caspase-3 in the pro-apoptotic effects exerted by brucine. Therefore, this paper indicate that the major alkaloids present in the seed of Strychnos nux-vomica are effective against HepG2 cells proliferation, among which brucine proceed HepG2 cells death via apoptosis, probably through the participation of caspase-3 and cyclooxygenase-2.
Assuntos
Alcaloides/farmacologia , Antineoplásicos/farmacologia , Carcinoma Hepatocelular/tratamento farmacológico , Neoplasias Hepáticas/tratamento farmacológico , Strychnos nux-vomica/química , Alcaloides/isolamento & purificação , Alcaloides/uso terapêutico , Antineoplásicos/isolamento & purificação , Antineoplásicos/uso terapêutico , Apoptose/efeitos dos fármacos , Carcinoma Hepatocelular/enzimologia , Carcinoma Hepatocelular/patologia , Caspase 3/biossíntese , Ciclo Celular/efeitos dos fármacos , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Forma Celular/efeitos dos fármacos , Óxidos N-Cíclicos/isolamento & purificação , Óxidos N-Cíclicos/farmacologia , Ciclo-Oxigenase 2/metabolismo , Relação Dose-Resposta a Droga , Humanos , Neoplasias Hepáticas/enzimologia , Neoplasias Hepáticas/patologia , Sementes , Estricnina/análogos & derivados , Estricnina/isolamento & purificação , Estricnina/farmacologiaRESUMO
AIM: To investigate the chemical constituents of the bulbs of Fritillaria wabuensia. METHODS: Chromatography techniques were used to isolate the chemical constituents. EI-MS, 1HNMR, 13 CNMR and DEPT were used to determine the structures of the isolated constituents. RESULTS: Three alkaloids were isolated from the bulbs of Fritillaria wabuensia, and were identified as imperialine (I), imperialine-beta-N-oxside (II), isoverticine-beta-N-oxide (III). CONCLUSION: Isoverticine-beta-N-oxide was isolated from the bulbs of Fritillaria wabuensia for the first time. Isoverticine-beta-N-oxide is a new alkaloid.
Assuntos
Óxidos N-Cíclicos/isolamento & purificação , Fritillaria/química , Plantas Medicinais/química , Triterpenos/isolamento & purificação , Cevanas/química , Cevanas/isolamento & purificação , Óxidos N-Cíclicos/química , Estrutura Molecular , Triterpenos/químicaRESUMO
AIM: To study the pharmacokinetic process about the concentration in rat plasma of the alkaloids from processed seeds of Strychnos nux-vomica with RP-HPLC method. METHODS: Hypersil BDS C18 column was used and the mobile phase consisted of acetonitrile-water at the flow rate of 0.8 mL.min-1. The UV detection wave length was 254 nm. RESULTS: The concentration-time data of strychnine, brucine, strychnine N-oxide and brucine N-oxide were all in accordance with an open two-compartment model after i.v. alkaloids. Their parameters were as follows: T1/2 alpha were (8 +/- 5), (4 +/- 3), (6.2 +/- 1.7) and (3.0 +/- 0.8) min, T1/2 beta were (262 +/- 125), (416 +/- 131), (285 +/- 50) and (342 +/- 141) min, CL were (17 +/- 4), (21 +/- 12), (1.9 +/- 1.8) and (2.8 +/- 1.1) mL.min-1, Vc were (1.4 +/- 0.5), (1.7 +/- 1.1), (0.24 +/- 0.16) and (0.23 +/- 0.06) L.kg-1, Vd were (6.0 +/- 1.2), (12 +/- 7), (0.8 +/- 0.6) and (1.5 +/- 0.6) L.kg-1, AUC were (57,578 +/- 25,578), (35,240 +/- 15,616), (93,088 +/- 22,375) and (177,712 +/- 120,110) h.microgram.L-1, respectively. CONCLUSION: The method is a good reference for pharmacokinetics in human bodies.
Assuntos
Alcaloides/farmacocinética , Medicamentos de Ervas Chinesas/farmacocinética , Sementes/química , Estricnina/análogos & derivados , Strychnos nux-vomica/química , Alcaloides/isolamento & purificação , Animais , Óxidos N-Cíclicos/isolamento & purificação , Óxidos N-Cíclicos/farmacocinética , Medicamentos de Ervas Chinesas/isolamento & purificação , Feminino , Temperatura Alta , Masculino , Plantas Medicinais/química , Ratos , Ratos Sprague-Dawley , Estricnina/isolamento & purificação , Estricnina/farmacocinética , Tecnologia Farmacêutica/métodosRESUMO
To further understand the purpose of the traditional processing method of the seeds of Strychnos nux-vomica L. (Loganiaceae) as well as analgesic and anti-inflammatory activities of brucine and brucine N-oxide extracted from this medicinal plant, various pain and inflammatory models were employed in the present study to investigate their pharmacological profiles. Both brucine and brucine N-oxide revealed significant protective effects against thermic and chemical stimuli in hot-plate test and writhing test. However, on different phases they exerted analgesic activities in formalin test. Brucine N-oxide showed stronger inhibitory effect than brucine in carrageenan-induced rat paw edema, both of them significantly inhibited the release of prostaglandin E2 in inflammatory tissue, reduced acetic acid-induced vascular permeability and the content of 6-keto-PGF1a in Freund's complete adjuvant (FCA) induced arthritis rat's blood plasma. In addition, brucine and brucine N-oxide were shown to reduce the content of 5-hydroxytryptamine (5-HT) in FCA-induced arthritis rat's blood plasma, while increase the content of 5-hydroxytryindole-3-acetic acid (5-HIAA) accordingly. These results suggest that central and peripheral mechanism are involved in the pain modulation and anti-inflammation effects of brucine and brucine N-oxide, biochemical mechanisms of brucine and brucine N-oxide are different even though they are similar in chemical structure.
Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Óxidos N-Cíclicos/farmacologia , Estricnina/análogos & derivados , Estricnina/farmacologia , Strychnos nux-vomica/química , Animais , Anti-Inflamatórios não Esteroides/isolamento & purificação , Artrite Experimental/sangue , Artrite Experimental/induzido quimicamente , Artrite Experimental/tratamento farmacológico , Permeabilidade Capilar/efeitos dos fármacos , Óxidos N-Cíclicos/isolamento & purificação , Modelos Animais de Doenças , Edema/induzido quimicamente , Edema/tratamento farmacológico , Feminino , Masculino , Camundongos , Camundongos Endogâmicos ICR , Dor/induzido quimicamente , Dor/tratamento farmacológico , Extratos Vegetais/farmacologia , Ratos , Ratos Sprague-Dawley , Sementes/química , Serotonina/sangue , Estricnina/isolamento & purificaçãoRESUMO
A new lupin alkaloid, (+)-sparteine N-16-oxide was isolated from Lygos raetam var. sarcocarpa, together with five known alkaloids: (+)-aphylline, (+)-17 oxosparteine, (-)-5,6-dehydrolupanine, (-)-N-formyl cytisine and (+)-ammodenderine. The structure of the new alkaloid including absolute configuration was determined by spectroscopic methods and chemical transformation.
Assuntos
Alcaloides/química , Óxidos N-Cíclicos/química , Extratos Vegetais , Esparteína/análogos & derivados , Alcaloides/isolamento & purificação , Óxidos N-Cíclicos/isolamento & purificação , Clima Desértico , Egito , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Esparteína/química , Esparteína/isolamento & purificaçãoRESUMO
Thirteen alkaloids were isolated from the seeds of Strychnos nux-vomica. They were identified as strychnine, beta-colubrine, pseudostrychnine, strychnine N-oxide, brucime, brucine N-oxide, novacine, icajine, vomicine, isostrychnine, isobrucine, isobrucine N-oxide and isostrychnine N-oxide by chemical and spectroscopic analysis.
Assuntos
Alcaloides/isolamento & purificação , Medicamentos de Ervas Chinesas/química , Óxidos N-Cíclicos/isolamento & purificação , Sementes/química , Estricnina/análogos & derivados , Estricnina/isolamento & purificaçãoRESUMO
Oxidation of insularine (I) with m-chloroperbenzoic acid yielded four insularine-N-oxides. Two of them are identical in every respect with our insularine-2 beta-N-oxide (II) and insularine-2' beta-N-oxide (III), two rare examples of naturally occurring head-to-tail bisbenzylisoquinoline N-oxides newly isolated from Cyclea sutchuenensis, which confirmed the structures of the two novel natural N-oxides. The other two are new compounds and their structures have been established as insularine-2' alpha-N-oxide (IV) and insularine-2 beta,2' beta-N, N-dioxide (V), on the basis of spectral data (UV, IR, 1HNMR, NOEDS AND MS) analysis.