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1.
Molecules ; 24(19)2019 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-31591371

RESUMO

Isoquinoline alkaloids are the main group of secondary metabolites present in Chelidonium majus extracts, and they are still the object of interest of many researchers. Therefore, the development of methods for the investigation and separation of the alkaloids is still an important task. In this work, the application potential of a silica-based monolithic column for the separation of alkaloids was assessed. The influence of the organic modifier, temperature, salt concentration, and pH of the eluent on basic chromatographic parameters such as retention, resolution between neighboring peaks, chromatographic plate numbers, and peak asymmetry were investigated. Based on the obtained results, a gradient elution program was developed and used to separate and quantitatively determine the main alkaloids in a Chelidonium majus root extract.


Assuntos
Alcaloides/isolamento & purificação , Chelidonium/química , Cromatografia Líquida de Alta Pressão/métodos , Isoquinolinas/isolamento & purificação , Alcaloides/análise , Isoquinolinas/análise , Extratos Vegetais/química , Dióxido de Silício
2.
Chin J Nat Med ; 17(9): 698-706, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31526505

RESUMO

Seven new isoquinoline alkaloids, 9-(2'-formyl-5', 6'-dimethoxyphenoxy)-1, 2, 3, 10-tetramethoxy dehydroaporphine (1), 9-(2'-formyl-5', 6'-dimethoxyphenoxy)-1, 2, 3, 10-tetramethoxy oxoaporphine (2), 3-methoxy-2'-formyl oxohernandalin (3), (-)-9-(2'-methoxycarbonyl-5', 6'-dimethoxyphenoxy)-1, 2, 3, 10-tetramethoxy aporphine (4), (-)-2'-methoxycarbonyl thaliadin (5), (-)-9-(2'-methoxyethyl-5', 6'-dimethoxyphenoxy)-1, 2, 3, 10-tetramethoxy aporphine (6), (-)-3-methoxy hydroxyhernandalinol (7), together with six known isoquinoline alkaloids (8-13) were isolated from the roots of Thalictrum foetidum. Their structures were elucidated by extensive spectroscopic measurements. Compounds 1 and 2 showed significant selective cytotoxicity against glioma stem cells (GSC-3# and GSC-18#) with IC50 values ranging from 2.36 to 5.37 µg·mL-1.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Aporfinas/farmacologia , Medicamentos de Ervas Chinesas/química , Células-Tronco Neoplásicas/efeitos dos fármacos , Thalictrum/química , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antineoplásicos Fitogênicos/química , Aporfinas/química , Aporfinas/isolamento & purificação , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Medicamentos de Ervas Chinesas/farmacologia , Glioma/patologia , Células HEK293 , Humanos , Concentração Inibidora 50 , Isoquinolinas/química , Isoquinolinas/isolamento & purificação , Isoquinolinas/farmacologia , Estrutura Molecular , Raízes de Plantas/química
3.
J Agric Food Chem ; 67(33): 9286-9294, 2019 Aug 21.
Artigo em Inglês | MEDLINE | ID: mdl-31339733

RESUMO

Natural aryl hydrocarbon (AHR) ligands have been identified in food and herbal medicines, and they may exhibit beneficial activity in humans. In this study, white button (WB) feeding significantly decreased AHR target gene expression in the small intestine of both conventional and germ-free mice. High-performance liquid chromatography (HPLC) fractionation and ultra-high-performance liquid chromatography tandem mass spectrometry (UHPLC-MS/MS) combined with an AHR-responsive cell-based luciferase gene reporter assay were used to isolate and characterize benzothiazole (BT) derivatives and 6-methylisoquinoline (6-MIQ) as AHR modulators from WB mushrooms. The study showed dose-dependent changes of AHR transformation determined by the cell-based luciferase gene reporter assay and transcription of CYP1A1 in human Caco-2 cells by BT derivatives and 6-MIQ. These findings suggested that WB mushroom contains new classes of natural AHR modulators and demonstrated HPLC fractionation and UHPLC-MS/MS combined with a cell-based luciferase gene reporter assay as a useful approach for isolation and characterization of the previously unidentifed AHR modulators from natural products.


Assuntos
Agaricus/química , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Receptores de Hidrocarboneto Arílico/genética , Animais , Benzotiazóis/química , Benzotiazóis/isolamento & purificação , Benzotiazóis/farmacologia , Linhagem Celular , Cromatografia Líquida de Alta Pressão , Citocromo P-450 CYP1A1/genética , Citocromo P-450 CYP1A1/metabolismo , Genes Reporter , Humanos , Isoquinolinas/química , Isoquinolinas/isolamento & purificação , Isoquinolinas/farmacologia , Ligantes , Camundongos , Extratos Vegetais/farmacologia , Receptores de Hidrocarboneto Arílico/metabolismo , Espectrometria de Massas em Tandem , Ativação Transcricional/efeitos dos fármacos , Verduras/química
4.
Biomed Chromatogr ; 33(9): e4565, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31032988

RESUMO

In previous structure-activity relationship studies to identify new and selective 5-HT7 receptor (5-HT7 R) ligands, we identified the chiral compound, 5-chloro-2-{2-[3,4-dihydroisoquinoline-2(1H)-yl]ethyl}-2-methyl-2,3-dihydro-1H-inden-1-one (SYA 40247), with high-affinity binding to the 5-HT7 R. Thus, it was of interest to separate the enantiomers in order to evaluate their affinity at the 5-HT7 R. To achieve this separation, a normal-phase analytical method using HPLC-PDA and a 4.6 × 250 mm Chiralpak AD-H column was developed. Optimized isocratic conditions of 1.00 mL/min 95:5:0.1 v/v/v hexane-ethanol-diethylamine and a 254 nm analysis wavelength yielded a 6.07 min baseline separation. The method was scaled up to a 10 × 250 mm Chiralpak AD-H column, allowing 3 mg of racemate to be separated with a single injection, and 6 mg for an overlapping double injection in the same run. The separated enantiomers were reinjected into the analytical HPLC system, peak identities confirmed by retention time and PDA UV spectra, and the enantiomeric purities determined to be 100% for peak 1 and 100% for peak 2. A Jasco P-1020 polarimeter was used to determine the specific rotation [α] of the enantiomers of peaks 1 and 2, which were -86.2 and +93.3 (deg mL)/(g dm) respectively. No racemization was observed, and the enantiomeric purity remained at 100% for each peak.


Assuntos
Amilose/análogos & derivados , Cromatografia Líquida de Alta Pressão/métodos , Indenos/química , Indenos/isolamento & purificação , Isoquinolinas/química , Isoquinolinas/isolamento & purificação , Fenilcarbamatos/química , Amilose/química , Isoquinolinas/análise , Ligantes , Receptores de Serotonina/química , Receptores de Serotonina/metabolismo , Estereoisomerismo
5.
Molecules ; 24(1)2019 Jan 07.
Artigo em Inglês | MEDLINE | ID: mdl-30621059

RESUMO

A new polyketide containing the benzoisoquinoline-9-one moiety, peyronetide A (1), and three other new derivatives peyronetides B⁻D (2⁻4), as well as one known compound (5) were purified from the cultured broth of the endophytic fungus Peyronellaea sp. FT431, which was isolated from the Hawaiian indigenous plant, Verbena sp. The structures of the new compounds were determined through the analysis of HRMS and NMR spectroscopic data. Compounds 1, 2, and 5 showed cytotoxic activities against TK-10 (human kidney adenocarcinoma cells), cisplatin sensitive A2780S (human ovarian carcinoma cells), and cisplatin resistant A2780CisR cell lines, with IC50 values between 6.7 to 29.2 µM.


Assuntos
Ascomicetos/química , Proliferação de Células/efeitos dos fármacos , Isoquinolinas/farmacologia , Neoplasias/tratamento farmacológico , Linhagem Celular Tumoral , Cisplatino/efeitos adversos , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Endófitos/química , Hawaii , Humanos , Concentração Inibidora 50 , Isoquinolinas/química , Isoquinolinas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular
6.
Nat Prod Res ; 33(5): 622-627, 2019 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-29126362

RESUMO

The phytochemical and biological investigation of Cissampelos pareira leads to the isolation of one new isoquinoline alkaloid (7) along with six known isoquinoline alkaloids, namely, magnoflorine (1), magnocurarine (2), cissamine (3), curine (4), hayatinine (5) and cycleanine (6). Magnoflorine (1) and magnocurarine (2) were isolated for the first time from C. pareira. A new, rapid, simple and sensitive UPLC method was developed for simultaneous quantification of five pure compounds (1-5). Seasonal variation study revealed higher content of these compounds during the rainy season. The chloroform (CPCF) and n-butanol (CPBF) fractions showed cytotoxic efficacy against KB cells. Among pure compounds, hayatinine (5) was found to be most active against KB and A549, while, cycleanine (6) against KB cells.


Assuntos
Alcaloides/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Cissampelos/química , Isoquinolinas/farmacologia , Células A549 , Alcaloides/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Aporfinas , Humanos , Índia , Isoquinolinas/isolamento & purificação , Células KB , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/química , Raízes de Plantas/química , Estações do Ano
7.
Electrophoresis ; 40(4): 582-586, 2019 02.
Artigo em Inglês | MEDLINE | ID: mdl-30488648

RESUMO

Far infrared radiation was employed in the rapid removal of the solvents in the extracts of Plumula Nelumbinis and standard mixture solutions to prevent the interference of the solvent peaks toward their capillary electrophoretic measurements. The sample solutions in small vials were exposed to far infrared ray at 60°C for 3 min to remove solvent. The dried samples in the vials were each dissolved into running buffer with the aid of ultrasonication for capillary electrophoresis analysis. The far infrared-assisted solvent removal approach was sucessfully applied in the rapid determination of neferine, liensinine, isoliensinine, rutin and hyperoside in Plumula Nelumbinis. The five analytes could be well separated within 12 min in a 40 cm long fused silica capillary at a separation voltage of 12 kV in a 50 mM borate buffer (pH 9.2). The results indicated that the interferences of the solvent peaks in the capillary electropherograms of the herbal drugs were eliminated completely.


Assuntos
Eletroforese Capilar/métodos , Metanol/química , Nelumbonaceae/química , Extratos Vegetais , Solventes/química , Desenho de Equipamento , Flavonóis/análise , Flavonóis/química , Flavonóis/isolamento & purificação , Raios Infravermelhos , Isoquinolinas/análise , Isoquinolinas/química , Isoquinolinas/isolamento & purificação , Limite de Detecção , Modelos Lineares , Extratos Vegetais/análise , Extratos Vegetais/química , Reprodutibilidade dos Testes
8.
Fitoterapia ; 131: 245-259, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-30419265

RESUMO

From the roots of the West African liana Ancistrocladus abbreviatus (Ancistrocladaceae), ten new naphthylisoquinoline alkaloids (7a, 7b, 8a, 8b, and 9-14), displaying three different coupling types (5,1', 5,8', and 7,8'), were isolated, among them a series of five 5,1'-linked representatives and four metabolites belonging to the rare group of 7,8'-coupled alkaloids. Two of the alkaloids, the ancistrobrevines I (13) and J (14), are only the fourth and fifth examples of 7,8'-linked naphthyldihydroisoquinolines ever found in nature. The stereostructures of the new plant metabolites were determined by spectroscopic, chemical (oxidative degradation), and chiroptical (electronic circular dichroism) methods. For the assignment of the axial configuration of 13 and 14 relative to the stereocenter at C-3, which is too far away for significant NOE long-range interactions, these 7,8'-coupled naphthyldihydroisoquinolines were stereoselectively converted into the respective cis-configured tetrahydroisoquinoline analogs. The newly generated 'auxiliary' stereocenter at C-1 permitted decisive NOE interactions between the isoquinoline and the naphthalene parts, and thus a reliable attribution of the axial configuration of 13 and 14. In addition, five known compounds (3, 5, 16, 17, and 20), previously discovered in related African and Asian Ancistrocladus species, have now for the first time been identified in A. abbreviatus. All of these alkaloids are S-configured at C-3 and bear an oxygen function at C-6, and are, thus, typical Ancistrocladaceae-type compounds. Some of the alkaloids of A. abbreviatus exhibited promising activities against the malaria parasite Plasmodium falciparum and PANC-1 human pancreatic cancer cells.


Assuntos
Alcaloides/farmacologia , Antimaláricos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Isoquinolinas/farmacologia , Raízes de Plantas/química , Plasmodium falciparum/efeitos dos fármacos , Traqueófitas/química , Alcaloides/isolamento & purificação , Antimaláricos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Costa do Marfim , Humanos , Isoquinolinas/isolamento & purificação , Estrutura Molecular , Neoplasias Pancreáticas , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia
9.
Phytochemistry ; 155: 93-99, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-30081273

RESUMO

The phytochemical study on Corydalis tomentella Franch, a traditional Chinese medicinal plant in Tibet, China, led to the isolation of six previously undescribed isoquinolines, including two rarely reported N-benzyl ones, and twenty-one known ones firstly obtained from this plant. Their planar structures were elucidated by 1D, 2D NMR experiments and high resolution mass spectrometry, and the absolute configurations were determined by NOE experiments, electronic circular dichroism, and specific rotation. Seven isoquinolines exhibited stronger hepatoprotective activities than that of positive control in D-galactosamine induced L02 cells damage model, which could be served as the leading compounds for further investigations. The primary structure-activity relationship was also summarized accordingly.


Assuntos
Corydalis/química , Isoquinolinas/farmacologia , Fígado/efeitos dos fármacos , Substâncias Protetoras/farmacologia , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , China , Galactosamina/antagonistas & inibidores , Humanos , Isoquinolinas/química , Isoquinolinas/isolamento & purificação , Fígado/patologia , Medicina Tradicional Chinesa , Estrutura Molecular , Plantas Medicinais/química , Substâncias Protetoras/química , Substâncias Protetoras/isolamento & purificação , Tibet
10.
Fitoterapia ; 130: 6-16, 2018 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-30059720

RESUMO

Four new naphthylisoquinoline alkaloids, the 5,8'-coupled ancistroyafungines A-C (1-3) and the 5,1'-linked ancistroyafungine D (4), have been isolated from the stem bark of an as yet unidentified Ancistrocladus (Ancistrocladaceae) liana recently discovered near the village Yafunga, in the North-Central region of the Democratic Republic of the Congo. Likewise obtained were eleven analogs previously identified in related African and Asian Ancistrocladus species, exhibiting five different coupling types, viz., 5,8', 5,1', 7,1', N,6', and N,8'. All of the alkaloids are S-configured at C-3 and possess an oxygen function at C-6 in the isoquinoline portion, and, thus, belong to the subclass of "Ancistrocladaceae-type" alkaloids. This finding is geo- and chemotaxonomically remarkable, since - apart from one other Ancistrocladus species from the Central Congo Basin - only Southeast Asian and East African Ancistrocladaceae are known to exclusively produce naphthylisoquinolines with these structural features. Moreover, the alkaloid pattern of this Congolese liana clearly demarcates this plant from all other Ancistrocladus taxa that have so far been botanically described, which suggests that it might represent a new species or subspecies. The new ancistroyafungines display strong preferential cytotoxic activities towards human PANC-1 pancreatic cancer cells in nutrient-deprived medium, without showing toxicity in normal, nutrient-rich conditions.


Assuntos
Alcaloides/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Caryophyllales/química , Isoquinolinas/farmacologia , Naftalenos/farmacologia , Compostos Fitoquímicos/farmacologia , Alcaloides/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , República Democrática do Congo , Humanos , Isoquinolinas/isolamento & purificação , Estrutura Molecular , Naftalenos/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Casca de Planta/química
11.
Fitoterapia ; 128: 247-252, 2018 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-29852264

RESUMO

Five new phenyl-C1 substituent aporphine alkaloids, 6aR-2'-methoxycarbonyl-thaliadin (1), 6aR-2'-carboxyl-thaliadin (2), 6aR-3-methoxy-hernandalinol (3), 6aS-1,3,10-trimethoxy-natalamine (4), and 3-methoxy-2'-methoxycarbonyl-oxohernandalincin (5), together with sixteen known isoquinoline alkaloids (6-21) were isolated from the whole herb of Thalictrum cirrhosum (Levl.). Their structures were elucidated by extensive spectroscopic measurements, and six isoquinoline alkaloids showed significant inhibitory activity on concanavalin A-stimulated splenocytes proliferation with IC50 values 36-44 µM by the immunosuppressive bioassay.


Assuntos
Alcaloides/isolamento & purificação , Aporfinas/isolamento & purificação , Isoquinolinas/isolamento & purificação , Thalictrum/química , Animais , Células Cultivadas , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Estrutura Molecular , Baço/citologia , Linfócitos T/efeitos dos fármacos
12.
Fitoterapia ; 128: 31-35, 2018 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-29715542

RESUMO

Encouraged by the anti-myocardial ischemic effect of Corydalis hendersonii ethanol extract, a chemical reinvestigation of the whole plant of C. hendersonii was performed, which led to the isolation of four new spirobenzylisoquinoline N-oxide alkaloids, hendersines C-F (1-4), along with seven known isoquinoline alkaloids (5-11). The structures of the new isolates including absolute configurations were elucidated by the analysis of spectroscopic data and comparison of the experimental and calculated electronic circular dichroism (ECD) data. Compound 1 inhibited the NO production in lipopolysaccharide (LPS)-induced RAW 264.7 cells with an IC50 value of 70.3 µM, and increased the cell viabilities with 40.0 ±â€¯3.9% against the oxygen glucose deprivation injury in H9c2 cells at 40 µM.


Assuntos
Alcaloides/isolamento & purificação , Corydalis/química , Isoquinolinas/isolamento & purificação , Alcaloides/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Hipóxia Celular , Isoquinolinas/farmacologia , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Células RAW 264.7 , Ratos
13.
J Appl Toxicol ; 38(10): 1274-1281, 2018 10.
Artigo em Inglês | MEDLINE | ID: mdl-29603306

RESUMO

Epidemic dropsy is a potentially life-threatening condition resulting from the ingestion of argemone oil derived from the seeds of Argemone mexicana Linn. Exposure to argemone oil is usually inadvertent, arising from mustard cooking oil adulteration. Sanguinarine, an alkaloid present in argemone oil, has been postulated as a causative agent with the severity of epidemic dropsy correlating with plasma sanguinarine levels. Cases of epidemic dropsy have also been reported following the topical application of argemone containing massage oil. Black salve, a topical skin cancer therapy also contains sanguinarine, but at significantly higher concentrations than that reported for contaminated massage oil. Although not reported to date, a theoretical risk therefore exists of black salve inducing epidemic dropsy. This literature review explores the presentation and pathophysiology of epidemic dropsy and assesses the risk of it being induced by black salve.


Assuntos
Argemone/química , Benzofenantridinas/toxicidade , Edema/induzido quimicamente , Isoquinolinas/toxicidade , Óleos Vegetais/toxicidade , Preparações de Plantas/toxicidade , Animais , Benzofenantridinas/sangue , Benzofenantridinas/isolamento & purificação , Edema/sangue , Humanos , Isoquinolinas/sangue , Isoquinolinas/isolamento & purificação , Óleos Vegetais/química , Sementes/química
14.
Bioorg Chem ; 77: 651-659, 2018 04.
Artigo em Inglês | MEDLINE | ID: mdl-29502026

RESUMO

Phytochemical investigation of the dichloromethane extract of the dried aerial parts of Corydalis rupestris (Papaveraceae) resulted in the identification of four new isoquinoline alkaloids rupestrines A-D and one known isoquinoline alkaloid, namely, stylopine. The structures of these compounds were characterized by extensive spectroscopic methods including 1D- (1H and 13C) and 2D NMR experiments (COSY, HSQC, HMBC, and NOESY) as well as HRESIMS analyses. In addition, the absolute configurations of rupestrines A-D were determined using modified Mosher's method. Cytotoxic effects of alkaloids and their interaction with albumin were also investigated in this study.


Assuntos
Alcaloides/química , Corydalis/química , Isoquinolinas/química , Componentes Aéreos da Planta/química , Alcaloides/isolamento & purificação , Relação Dose-Resposta a Droga , Humanos , Isoquinolinas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Relação Estrutura-Atividade , Células Tumorais Cultivadas
15.
J Asian Nat Prod Res ; 20(3): 195-200, 2018 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-28503941

RESUMO

Two pyrrolo[2,1-a]isoquinolines (1 and 2) and three pyrrole alkaloids (3-5), including three new ones, named sinopyrines A-C (1-3), were isolated from the 95% EtOH extract of the stems and rhizomes of Sinomenium acutum (Thumb.) Rehd. et Wils. The structures of the new compounds were elucidated on the basis of spectroscopic data. This is the first report of pyrrole-bearing natural compounds from the family Menispermaceae.


Assuntos
Alcaloides/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Isoquinolinas/isolamento & purificação , Pirróis/isolamento & purificação , Sinomenium/química , Alcaloides/química , Medicamentos de Ervas Chinesas/química , Isoquinolinas/química , Estrutura Molecular , Caules de Planta/química , Pirróis/química , Rizoma/química
16.
J Microbiol Biotechnol ; 28(2): 262-266, 2018 Feb 28.
Artigo em Inglês | MEDLINE | ID: mdl-29141127

RESUMO

Phytochemicals have been considered as alternatives for synthetic fungicides because of their biodegradability and low toxicity. In this study, we found that the methanolic extract of Corydalis ternata suppressed the development of plant diseases caused by Puccinia triticina and Colletotrichum coccodes. As the antifungal substance, three isoquinoline alkaloids (dehydrocorydaline, stylopine, and corydaline) were isolated from C. ternata. These active compounds also exhibited in vivo antifungal activity against P. triticina and C. coccodes. Taken together, our results suggest that C. ternata and its active compounds can be used to control plant diseases.


Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Corydalis/química , Isoquinolinas/isolamento & purificação , Isoquinolinas/farmacologia , Exsudatos de Plantas/farmacologia , Alcaloides/química , Antifúngicos/química , Basidiomycota/efeitos dos fármacos , Basidiomycota/patogenicidade , Alcaloides de Berberina/isolamento & purificação , Alcaloides de Berberina/farmacologia , Colletotrichum/efeitos dos fármacos , Colletotrichum/patogenicidade , Fungicidas Industriais , Isoquinolinas/química , Metanol , Doenças das Plantas/microbiologia , Triticum/microbiologia , Verduras/microbiologia
17.
Fitoterapia ; 124: 58-65, 2018 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29108933

RESUMO

A new skeleton benzylisoquinoline (BI) named neoliensinine (1) was isolated from embryos of lotus seed (Nelumbo nucifera Gaertn.), a traditional Chinese herb. The tribenzylisoquinoline (TBI) structure of 1 was confirmed by interpreting spectroscopic data of UV, IR, MS, 1D and 2D NMR. The stereo-configurations of the new compound, together with two known bisbenzylisoquinolines (BBI), neferine and isoliensinine were established by analyzing 1H NMR and 13C NMR spectra. The relaxation of 1, neferine, isoliensinine and liensinine in isolated mesenteric vascular smooth muscle (VSM) was evaluated. All the four BIs could efficiently inhibit MVSM contraction induced by 124mM KCl, with IC50 values of 2.407µM (1), 1.169µM (neferine), 3.504µM (isoliensinine) and 3.583µM (liensinine), respectively, suggesting that they were all potential relaxants for abnormal smooth muscle contractions. Interestingly, VSM treated by the three BBIs could re-contract when being stimulated by KCl after the drugs were removed, while VSM dealt with the TBI couldn't. It indicated that 1 has much high affinity with the molecular targets on relaxation of VSM contraction, which may relate to the unique skeleton with three BI groups.


Assuntos
Alcaloides/isolamento & purificação , Músculo Liso/efeitos dos fármacos , Nelumbo/química , Fármacos Neuromusculares/isolamento & purificação , Animais , Benzilisoquinolinas/isolamento & purificação , Feminino , Técnicas In Vitro , Isoquinolinas/isolamento & purificação , Masculino , Camundongos Endogâmicos C57BL , Estrutura Molecular , Fenóis/isolamento & purificação , Sementes/química
18.
J Nat Prod ; 80(10): 2807-2817, 2017 10 27.
Artigo em Inglês | MEDLINE | ID: mdl-29043798

RESUMO

Two new naphthylisoquinoline dimers, jozilebomines A (1a) and B (1b), were isolated from the roots of the Congolese plant Ancistrocladus ileboensis, along with the known dimer jozimine A2 (2). These compounds are Dioncophyllaceae-type metabolites, i.e., lacking oxygen functions at C-6 and with an R-configuration at C-3 in their tetrahydroisoquinoline moieties. The dimers 1a and 1b consist of two 7,1'-coupled naphthylisoquinoline monomers linked through an unprecedented 3',6″-coupling in the binaphthalene core and not, as in 2, via the C-3-positions of the two naphthalene units. Thus, different from the C2-symmetric jozimine A2 (2), the new jozilebomines are constitutionally unsymmetric. The central biaryl axis of each of the three dimers is rotationally hindered, so that 1a, 1b, and 2 possess three consecutive chiral axes. The two jozilebomines have identical constitutions and the same absolute configurations at all four stereogenic centers, but differ from each other in their axial chirality. Their structural elucidation was achieved by HRESIMS, 1D and 2D NMR, oxidative degradation, and experimental and calculated ECD data. They exhibited distinct and specific antiplasmodial activities. All dimers showed potent cytotoxicity against HeLa human cervical cancer cells and preferential cytotoxicity against PANC-1 human pancreatic cancer cells under nutrition-deprived conditions. Furthermore, these dimers significantly inhibited the colony formation of PANC-1 cells, even when exposed to noncytotoxic concentration for a short time. Jozilebomines A (1a) and B (1b) and jozimine A2 (2) represent novel potential candidates for future drug development against pancreatic cancer.


Assuntos
Antimaláricos/isolamento & purificação , Antimaláricos/farmacologia , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Isoquinolinas/isolamento & purificação , Isoquinolinas/farmacologia , Naftalenos/isolamento & purificação , Naftalenos/farmacologia , Neoplasias Pancreáticas/tratamento farmacológico , Algoritmos , Alcaloides/química , Animais , Antimaláricos/química , Antineoplásicos Fitogênicos/química , Congo , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Isoquinolinas/química , Leishmania donovani/efeitos dos fármacos , Magnoliopsida/química , Estrutura Molecular , Naftalenos/química , Ressonância Magnética Nuclear Biomolecular , Plasmodium falciparum/efeitos dos fármacos , Ratos , Trypanosoma brucei rhodesiense/efeitos dos fármacos , Trypanosoma cruzi/efeitos dos fármacos , Células Tumorais Cultivadas
19.
Chem Biodivers ; 14(10)2017 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-28695650

RESUMO

A novel tropoloisoquinoline alkaloid, neotatarine (1), was isolated from the 95% ethanol extract of the rhizome parts of Acorus calamus L. The chemical structure was unambiguously elucidated by spectroscopic and single-crystal X-ray diffraction analysis. Neotatarine (1) exhibited significantly inhibitory activity against Aß25 - 35 induced PC12 cell death with 2, 4 and 8 µm comparing with the assay control (P < 0.01).


Assuntos
Acorus/química , Peptídeos beta-Amiloides/antagonistas & inibidores , Isoquinolinas/farmacologia , Fragmentos de Peptídeos/antagonistas & inibidores , Tropolona/análogos & derivados , Animais , Morte Celular/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Relação Dose-Resposta a Droga , Isoquinolinas/química , Isoquinolinas/isolamento & purificação , Estrutura Molecular , Células PC12 , Ratos , Relação Estrutura-Atividade , Tropolona/química , Tropolona/isolamento & purificação , Tropolona/farmacologia
20.
Fitoterapia ; 121: 76-85, 2017 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-28688886

RESUMO

A striking feature of the metabolite pattern of the Southeast Asian liana Ancistrocladus tectorius (Ancistrocladaceae) is the predominance of 5,1'-coupled naphthylisoquinoline alkaloids. About 20 alkaloids of this coupling type have so far been discovered in this plant species. Here, we report on the isolation of four new 5,1'-linked naphthylisoquinolines from the twigs and stems of A. tectorius. Two of them, the ancistrobenomines B (5) and C (6), belong to the very rare group of alkaloids with a fully dehydrogenated isoquinoline portion. Likewise unusual for naphthylisoquinoline alkaloids is the presence of a hydroxymethylene group at C-3. Within the large class of meanwhile ca. 180 such natural products, this structural peculiarity had so far been known only from two other representatives isolated from the Malaysian species A. benomensis, and from one single naphthalene-devoid 3-hydroxymethyleneisoquinoline from A. tectorius. Seven further 5,1'-linked alkaloids, previously isolated from related Asian and African Ancistrocladus species, have now been identified for the first time in A. tectorius. Their structural elucidation was achieved by spectroscopic analysis including HRESIMS, 1D and 2D NMR, and by chemical (oxidative degradation) and chiroptical (electronic circular dichroism) methods. Ancistrobenomine B (5) exhibited moderate effects against Plasmodium falciparum and Trypanosoma brucei rhodesiense in vitro, and it was found to display strong cytotoxic activities against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells and their multidrug-resistant subline, CEM/ADR5000.


Assuntos
Alcaloides/química , Antimaláricos/química , Antineoplásicos Fitogênicos/química , Isoquinolinas/química , Magnoliopsida/química , Naftalenos/química , Alcaloides/isolamento & purificação , Antimaláricos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Isoquinolinas/isolamento & purificação , Estrutura Molecular , Naftalenos/isolamento & purificação , Caules de Planta/química , Plasmodium falciparum/efeitos dos fármacos , Trypanosoma brucei rhodesiense/efeitos dos fármacos
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