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1.
Molecules ; 26(3)2021 Jan 23.
Artigo em Inglês | MEDLINE | ID: mdl-33498621

RESUMO

In the course of our studies on antiprotozoal natural products and following our recent discovery that certain aminosteroids and aminocycloartanoid compounds from Holarrhena africana A. DC. (Apocynaceae) and Buxus sempervirens L. (Buxaceae), respectively, are strong and selective antitrypanosomal agents, we have extended these studies to another plant, related to the latter-namely, Pachysandra terminalis Sieb. and Zucc. (Buxaceae). This species is known to contain aminosteroids similar to those of Holarrhena and structurally related to the aminocycloartanoids of Buxus. The dicholoromethane extract obtained from aerial parts of P. terminalis and, in particular, its alkaloid fraction obtained by acid-base partitioning showed prominent activity against Trypanosoma brucei rhodesiense (Tbr). Activity-guided fractionation along with extended UHPLC-(+)ESI QTOF MS analyses coupled with partial least squares (PLS) regression modelling relating the analytical profiles of various fractions with their bioactivity against Tbr highlighted eighteen constituents likely responsible for the antitrypanosomal activity. Detailed analysis of their (+)ESI mass spectral fragmentation allowed identification of four known constituents of P. terminalis as well as structural characterization of ten further amino-/amidosteroids not previously reported from this plant.


Assuntos
Alcaloides/química , Buxaceae/química , Pachysandra/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Trypanosoma brucei rhodesiense/química , Antiprotozoários/química , Apocynaceae/química , Buxus/química , Holarrhena/química , Tripanossomicidas/química , Tripanossomicidas/farmacologia
2.
Fitoterapia ; 144: 104604, 2020 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-32380036

RESUMO

Sarcorusones A-D (1-4), four new androstane (C19-steroid) derivatives were characterized from Sarcococca ruscifolia along with five known compounds. Their structures were elucidated on the basis of extensive MS and NMR spectroscopic analysis. All the new structures share common 14-hydroxyl and 17-ketone functional groups, and compounds 2-4 feature a seneciamide group connecting to C-3 position. The inhibitory activities of all the isolates against melanoma cell B16F10 and lung cancer cell H1299 were evaluated, and compounds 2, 3, 5, and 6 exhibited moderate cytotoxic activities against B16F10 and H1299 cell lines with IC50 values 2.7-8.0 µM.


Assuntos
Androstanos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Buxaceae/química , Androstanos/isolamento & purificação , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , China , Humanos , Melanoma Experimental , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia
3.
Chem Biol Drug Des ; 95(2): 233-239, 2020 02.
Artigo em Inglês | MEDLINE | ID: mdl-31584741

RESUMO

Plant-derived natural products are of great interest due to their diversity in modern drug discovery. Sarcococca saligna has been used for the treatment of different diseases. The present study was aimed at isolating phytochemical constituents including Alkaloid-C (a), Dictyophlebine (b), Sarcovagine-D (c) and Saracodine (d) Holaphylline (e) from Sarcococca saligna to investigate the anticancer effect of these compounds. These compounds were evaluated for inhibition of aromatase enzyme of breast cancer in assistance by molecular docking simulations to understand molecular interaction between the enzyme and ligands. The IC50 values of compound 1 and 5 were found 138.27 ± 0.01 µl and 12.91 ± 0.01 µl, respectively, and both were found active due to their bulky structures in comparison to the active site of aromatase enzyme. The standard drug exemestane showed potent activity in comparison with the test compounds, having IC50 values of 0.052 ± 0.01 µl. Both compounds showed favorable electrostatic interactions with the active site of aromatase enzyme but the shape and steric bulk of the compounds was the limiting factor in their inhibitory effects. New lead compounds could be generated after extensive modifications guided by computational and experimental tools as a possible anticancer agents by targeting aromatase enzyme.


Assuntos
Alcaloides/farmacologia , Inibidores da Aromatase/farmacologia , Neoplasias da Mama/tratamento farmacológico , Pós-Menopausa , Esteroides/farmacologia , Alcaloides/química , Inibidores da Aromatase/química , Inibidores da Aromatase/uso terapêutico , Sítios de Ligação , Buxaceae/química , Humanos , Ligação de Hidrogênio , Interações Hidrofóbicas e Hidrofílicas , Esteroides/química
4.
Nat Prod Res ; 33(2): 169-173, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29451012

RESUMO

A new steroidal alkaloid, 4-dehydroxyepisarcovagine A (1), along with seven known alkaloids, sarcovagine D (2), sarcovagenine C (3), epoxysarcovagenine D (4), Pachysamine L (5), Pachysamine E (6), sarcovagine A (7) and sarcovagine B (8), was isolated from the roots and stems of Sarcococca pruniformis Lindl. The structure of compound 1 was elucidated by means of spectroscopic analysis.


Assuntos
Alcaloides/química , Buxaceae/química , Esteroides/química , Alcaloides/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Raízes de Plantas/química , Caules de Planta/química , Esteroides/isolamento & purificação
5.
Molecules ; 24(1)2018 Dec 20.
Artigo em Inglês | MEDLINE | ID: mdl-30577522

RESUMO

Two new steroidal alkaloids, named hookerianine A (1) and hookerianine B (2) were isolated from the stems and roots of Sarcococca hookeriana Baill., along with two known compounds, sarcorucinine G (3) and epipachysamine D (4). On the basis of spectroscopic methods and by comparison with literature data, their structures were determined. As well as X-ray crystallography was performed to confirm compound 4. To identify novel antitumor inhibitors, all compounds were performed a CCK-8 assay against five human cancer cell lines SW480, SMMC-7721, PC3, MCF-7 and K562 in vitro. Compound 2 exhibited moderate cytotoxic activities to all cell lines with IC50 values in the range of 5.97⁻19.44 µM. Compound 3 was the most effective one against SW480 and K562 cell lines with IC50 values of 5.77 and 6.29 µM, respectively.


Assuntos
Buxaceae/química , Sobrevivência Celular/efeitos dos fármacos , Esteroides/química , Esteroides/farmacologia , Alcaloides/química , Alcaloides/farmacologia , Linhagem Celular Tumoral , Cristalografia por Raios X , Humanos , Células K562 , Células MCF-7 , Células PC-3
6.
Molecules ; 23(5)2018 May 15.
Artigo em Inglês | MEDLINE | ID: mdl-29762510

RESUMO

Three new steroidal alkaloids with an unusual 3α tigloylamide group, named sarchookloides A⁻C (1⁻3), were isolated along with four known compounds (4⁻7) from the roots of Sarcococca hookeriana. Their structures and relative configuration were elucidated on the basis of spectroscopic methods including MS, UV, IR, 1D, and 2D NMR data. The isolated compounds were evaluated for their cytotoxicity against five human cancer cell lines: Hela, A549, MCF-7, SW480, and CEM in vitro. All three amide substituted steroidal alkaloids exhibited significant cytotoxic activities with IC50 values of 1.05⁻31.83 µM.


Assuntos
Alcaloides/química , Alcaloides/farmacologia , Buxaceae/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Esteroides/química , Esteroides/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular
7.
Nat Prod Commun ; 10(9): 1533-6, 2015 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-26594751

RESUMO

Bio-assay guided isolation from the plant Sarcococca wallichii Staph. yielded two new steroidal alkaloids: wallichimine A (1) and wallichimine B (2), and five known ones: sarcodinine (3), N-methylpachysamine A (4), alkaloid C (5), dictyophlebine (6), and sarcorine (7). The structures of the compounds were determined using mass spectrometry and NMR spectroscopy techniques. The immunomodulatory potential of compounds was evaluated on different parameters including production of intracellular reactive oxygen species (ROS), nitric oxide (NO) and on proinflammatory cytokine TNF-α. All compounds were found to be potent inhibitors of intracellular ROS produced from isolated neutrophils, except compound 5, which showed a moderate level of inhibition. Compounds 2 and 4 potently inhibited the production of NO (67.9% and 62.5% respectively). Compound 2 showed potent suppression on production of proinflammatory cytokine TNF-α (76.7%). Among all the tested compounds the new compound 2 was found to be the most potent immunosuppressive agent. This study shows that steroidal alkaloids could be lead compounds for anti-inflammatory drug discovery.


Assuntos
Alcaloides/farmacologia , Anti-Inflamatórios/farmacologia , Buxaceae/química , Esteroides/farmacologia , Alcaloides/química , Anti-Inflamatórios/química , Nepal , Esteroides/química
8.
Int Immunopharmacol ; 28(1): 235-43, 2015 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-26093268

RESUMO

Sarcococca saligna methanolic extract, fractions and isolated pure compounds saracocine (1), saracodine (2), pachyximine-A (3) and terminaline (4) were found to possess potent immunosuppressive activities. The fractions and compounds were tested in-vitro for their effects on human T-cell proliferation, and cytokine (IL-2) production. All the fractions, sub-fractions and purified compounds showed significant suppressive effect on IL-2 production in a dose-dependent manner. They also exhibited a suppressive effect on the phytohemagglutinin-stimulated T-cell proliferation. None of the extracts and purified compounds showed any cytotoxicity effects on the 3T3 mice fibroblast cell line. The crude extract, DCM fraction (pH9), DCM fractions (pH7) and one of the steroidal alkaloids (terminaline) were checked in-vivo for their hepato-protective potential against CCl4-induced liver injury. In in-vivo experiments, the basic and neutral DCM fractions and terminaline (4) significantly reduced inflammation in the liver. DCM fraction (pH9), DCM fractions (pH7) and compound 4 reduced the serum enzyme levels (ALT, AST, and ALP) down to control levels despite CCl4 treatment. They also reduced the CCl4-induced damaged area to almost zero as assessed by histopathology. The pale necrotic areas and mixed inflammatory infiltrate which are seen after CCl4 treatment were absent in the cases of basic, neutral fractions and terminaline treatment. These hepato-protective effects were better than the positive control silymarin. Our results suggest the therapeutic effect of S. saligna extract, fractions and bioactive steroidal alkaloids against CCl4-induced liver injury in vivo and their immunosuppressive function in vitro.


Assuntos
Buxaceae/química , Doença Hepática Induzida por Substâncias e Drogas/prevenção & controle , Imunossupressores/farmacologia , Extratos Vegetais/farmacologia , Substâncias Protetoras/farmacologia , Células 3T3 , Animais , Biomarcadores/metabolismo , Intoxicação por Tetracloreto de Carbono/patologia , Intoxicação por Tetracloreto de Carbono/prevenção & controle , Proliferação de Células/efeitos dos fármacos , Humanos , Imunossupressores/química , Interleucina-2/biossíntese , Linfócitos/efeitos dos fármacos , Masculino , Camundongos , Extratos Vegetais/química , Substâncias Protetoras/química , Ratos , Ratos Wistar , Linfócitos T/efeitos dos fármacos
9.
Fitoterapia ; 89: 143-8, 2013 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-23651560

RESUMO

Fourteen pregnane-type steroidal alkaloids were isolated from the ethanolic extracts of whole Sarcococca hookeriana var. digyna plants. Their structures were elucidated on the basis of spectral data. Three of them were identified as new steroidal alkaloids: (S)-20-(N,N-dimethylamino)-16α,17α-epoxy-3ß-methoxy-pregn-5-ene (1), (20S)-20-(N,N-dimethylamino)-3ß-tigloylamino-5α-pregn-11ß-ol (2), and (20S)-2α,4ß-bis(acetoxy)-20-(N,N-dimethylamino)-3ß-tigloylamino-5α-pregnane (3). Some of the isolated compounds showed estrogen biosynthesis-promoting effects in human ovarian granulosa-like KGN cells. The EC50 values for the most effective compounds, vagnine B (6) and funtumafrine C (12), were 71 µM and 67 µM, respectively.


Assuntos
Alcaloides/isolamento & purificação , Buxaceae/química , Estrogênios/biossíntese , Fitoestrógenos/isolamento & purificação , Extratos Vegetais/química , Pregnanos/isolamento & purificação , Alcaloides/química , Alcaloides/farmacologia , Humanos , Estrutura Molecular , Fitoestrógenos/química , Fitoestrógenos/farmacologia , Extratos Vegetais/farmacologia , Pregnanos/química , Pregnanos/farmacologia
10.
Vet Parasitol ; 188(3-4): 362-7, 2012 Sep 10.
Artigo em Inglês | MEDLINE | ID: mdl-22516644

RESUMO

We report a new bioassay "syringe test" (modified larval immersion test) for in vitro evaluation of acaricidal activity of crude plant extracts. Prepared syringes, containing eggs of tick, were incubated until 14 d after hatching of eggs, when the bioassay was performed on the larvae. Lethal concentrations for 50% of larvae (LC(50)), LC(90) and LC(99) values were calculated for each tested product. 95% confidence intervals for LC(50) were very narrow, indicating a high degree of repeatability for the new bioassay on larvae of R. microplus. Bioassays were applied to six crude aqueous-methanol extracts from five plants (Acacia nilotica, Buxus papillosa, Fumaria parviflora, Juniperus excelsa, and Operculina turpethum), of which three showed discernible effects. Twenty-four hours post exposure, LC(99) values were 11.9% (w/v) for F. parviflora, 20.8% (w/v) and 29.2% (w/v) for B. papillosa and A. nilotica, respectively. After six days of exposure these values were; 9.1% (w/v), 9.2% (w/v) and 15.5 (w/v) for F. parviflora, A. nilotica and B. papillosa, respectively.


Assuntos
Acaricidas/farmacologia , Bioensaio/métodos , Magnoliopsida/química , Extratos Vegetais/farmacologia , Rhipicephalus/efeitos dos fármacos , Infestações por Carrapato/parasitologia , Acaricidas/isolamento & purificação , Animais , Buxaceae/química , Convolvulaceae/química , Fabaceae/química , Feminino , Fumaria/química , Imersão , Juniperus/química , Larva , Dose Letal Mediana , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Reprodutibilidade dos Testes , Sensibilidade e Especificidade
11.
Steroids ; 77(1-2): 138-48, 2012 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-22093483

RESUMO

Rapid characterization of 23 pregnane-type steroidal alkaloids was studied using a positive ion electrospray ionization quadropole time-of-flight mass spectrometry (ESI-QqTOF-MS/MS) hybrid instrument. ESI-QqTOF-MS (positive ion mode) showed the presence of the protonated molecules [M+H](+) which through low-energy collision-induced dissociation tandem mass spectrometric (CID-MS/MS) analysis showed the characteristic loss of dimethylamine moiety [M+H-45](+) followed by the sequential lossess of attached substituents. Steroidal alkaloids having tigloyl or senecioyl group at C-3 produced diagnostic fragment ions at m/z 100 and 83. Our study also demonstrates the influence of unsaturation, and number and nature of substitutents on product ion abundance and fragment ions. Moreover, the generalization of the fragmentation pattern was linked with the structural features in steroidal skeleton. This strategy was successfully applied in LC-ESI-QqTOF-MS/MS analysis of Sarcococca coriacea extract to investigate and characterize pregnane-type steroidal alkaloids in complex mixture.


Assuntos
Alcaloides/análise , Buxaceae/química , Extratos Vegetais/análise , Raízes de Plantas/química , Esteroides/análise , Alcaloides/isolamento & purificação , Cromatografia Líquida , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Plantas Medicinais/química , Espectrometria de Massas por Ionização por Electrospray , Esteroides/isolamento & purificação , Espectrometria de Massas em Tandem
12.
Planta Med ; 77(15): 1725-9, 2011 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-21590651

RESUMO

Two new C21-steroidal esters, sarsaligates A(1) and B(2), and two new steroidal alkaloids, sarsaligenines A(3) and B(4), together with four known compounds (sarcovagine, sarcorucinine, dimethylamino-3 ß-pregnane-20-one, and ß-sitosterol 5- 8, respectively), were isolated from the leaves and stems of Sarcococca saligna. The structures of compounds 1-4 were elucidated by NMR and MS spectroscopic analysis. Of the compounds tested, 5 and 6 were the most cytotoxic against the cell lines K562, SK-BR-3, and PANC-1, with IC50 values in the range of 2.25-5.00 µM, while 3 and 4 selectively inhibited HL-60 cells with IC50 values of 2.87 and 3.61 µM, respectively. Compounds 3-6 therefore deserve further evaluation of their cytotoxic potentials.


Assuntos
Buxaceae/química , Citotoxinas/química , Medicamentos de Ervas Chinesas/química , Fitosteróis/química , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular , Citotoxinas/isolamento & purificação , Citotoxinas/farmacologia , Ésteres , Feminino , Gastroenteropatias/prevenção & controle , Humanos , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Fitosteróis/isolamento & purificação , Fitosteróis/farmacologia , Folhas de Planta/química , Caules de Planta/química , Plantas Medicinais/química
13.
J Asian Nat Prod Res ; 12(3): 233-8, 2010 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-20390771

RESUMO

Two new steroidal alkaloids, 20alpha-dimethylamino-2alpha-hydroxyl-3beta-tigloylamino-5alpha-pregnane (1) and Delta(16)-20alpha-dimethylamino-3beta,4alpha-diol-5alpha-pregnane (2), along with five known alkaloids, sarcovagine D (3), pachysamine G (4), pachysamine H (5), pachysamine A (6), and terminaline (20S)-20-(N,N-dimethylamino)-5alpha-pregn-3beta,4alpha-diol (7), were isolated from the roots of Sarcococca ruscifolia. Their structures were elucidated on the basis of NMR and MS data, and the relative stereochemistry of 1 was finally determined by X-ray crystallographic analysis.


Assuntos
Alcaloides/isolamento & purificação , Buxaceae/química , Medicamentos de Ervas Chinesas/isolamento & purificação , Pregnanos/isolamento & purificação , Alcaloides/química , Cristalografia por Raios X , Medicamentos de Ervas Chinesas/química , Conformação Molecular , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Raízes de Plantas/química , Pregnanos/química , Estereoisomerismo
14.
Planta Med ; 76(10): 1022-5, 2010 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-20186658

RESUMO

Four new 5 alpha-pregnane-type steroidal alkaloids, hookerianamides L(1), M(2), N(3), and O(4), and a known N-formylchonemorphine (5) have been isolated by acid-base extraction of the dichloromethane extract of Sarcococca hookeriana. The structures of all compounds were determined with spectroscopic techniques and by comparison with literature data. All compounds displayed antileishmanial and antibacterial properties. Compounds 1, 4, and 5 were found to be more potent than standard pentamidine (IC (50) = 9.59 microg/mL) with respect to leishmanicidal activity. The minimum inhibitory concentration of most of the compounds against Bacillus subtilis, Streptococcus minor, and Streptococcus ferus was lower than that of the standard ampicillin.


Assuntos
Alcaloides/isolamento & purificação , Antibacterianos/isolamento & purificação , Buxaceae/química , Pregnanos/farmacologia , Esteroides/isolamento & purificação , Tripanossomicidas/isolamento & purificação , Alcaloides/química , Alcaloides/farmacologia , Ampicilina/farmacologia , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Pentamidina/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Pregnanos/isolamento & purificação , Esteroides/química , Esteroides/farmacologia , Tripanossomicidas/farmacologia
15.
Appl Biochem Biotechnol ; 162(1): 127-33, 2010 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-19685213

RESUMO

Microbial resistance is a major drawback in chemotherapy of microbial or fungal infection disease. In this study, the antifungal activity of ethanol extract of a selected plant (Sarcococca saligna) has been investigated against clinical isolates of Aspergillus niger, Aspergillus treus, Aspergillus flavus, and Aspergillus fumigatus. Also, the enhancement of the antifungal activity of fluconazole by this extract was further evaluated against mentioned test strains. Conventional disk diffusion method was used to assay the antifungal activity of S. saligna ethanol extract in the absence and presence of fluconazole. The highest antifungal activity was observed against A. treus. The ethanol extract of S. saligna enhanced the antifungal activity of fluconazole against A. niger and A. treus and A. flavus. At the highest tested contents (4 mg/disk), 1.15-, 0.64-, and 2.47-fold increases in inhibition zone surface area were observed for A. niger, A. treus, and A. flavus, respectively. However, no enhancing effect was observed for this plant extract against Aspergillus fumigates at tested contents (0.5, 1, 2, 3, and 4 mg/disk). In a separate experiment, the general cytotoxicity of the ethanol extract of S. saligna was examined with brine shrimp assay. This plant extract showed low cytotoxicity against Artemia salina (LC(50) = 186 microg/ml).


Assuntos
Antifúngicos/farmacologia , Aspergillus/efeitos dos fármacos , Buxaceae/química , Farmacorresistência Fúngica/efeitos dos fármacos , Etanol/química , Fluconazol/farmacologia , Extratos Vegetais/farmacologia , Animais , Antifúngicos/toxicidade , Artemia/efeitos dos fármacos , Testes de Sensibilidade a Antimicrobianos por Disco-Difusão , Interações Medicamentosas , Extratos Vegetais/toxicidade
16.
J Nat Prod ; 71(8): 1481-4, 2008 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-18681480

RESUMO

The bioassay-guided phytochemical investigation of Sarcococca hookeriana with respect to cholinesterase inhibitory properties has yielded two new 5alpha-pregnane-type steroidal alkaloids, hookerianamides J (1) and K (2), along with eight known compounds (3-10). The structures of 1 and 2 were elucidated by spectroscopic methods. These compounds displayed good to moderate activities in vitro against the enzymes acetylcholinesterase (IC 50 8.1-48.5 microM) and butyrylcholinesterase (IC 50 0.4-4.0 microM). Compounds 1-10 were also tested in vitro for their leishmanicidal activity against Leishmania major and for their antibacterial activities against Bacillus subtilis, Micrococcus luteus, Streptococcus faecalis, and Pseudomonas pallida.


Assuntos
Alcaloides/isolamento & purificação , Buxaceae/química , Pregnanos/química , Alcaloides/química , Alcaloides/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Antibacterianos/farmacologia , Antiprotozoários/química , Antiprotozoários/isolamento & purificação , Antiprotozoários/farmacologia , Inibidores da Colinesterase/química , Inibidores da Colinesterase/isolamento & purificação , Inibidores da Colinesterase/farmacologia , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray
17.
Nat Prod Rep ; 25(3): 612-30, 2008 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-18497899

RESUMO

The plants of the family Buxaceae are widely used in traditional medicine and constitute rich sources of terpenoidal alkaloids. Compounds of this family have been the subject of numerous chemical and pharmacological studies over past decades because of their interesting biological activities such as cholinesterase inhibition, as well as antibacterial and antileishmanial activities. The chemical and biological properties of these alkaloids, including data relevant to straightforward structure determination and information on biosynthesis, are highlighted in this review, with 144 references being cited.


Assuntos
Alcaloides , Buxaceae/química , Plantas Medicinais/química , Terpenos/farmacologia , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Estrutura Molecular , Terpenos/química , Terpenos/isolamento & purificação
18.
Chem Pharm Bull (Tokyo) ; 55(9): 1397-401, 2007 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-17827771

RESUMO

Bioguided phytochemical investigation of Sarcococca hookeriana with respect to the cholinesterase enzyme inhibitory assay yielded two new pregnane-type steriodal alkaloids hookerianamide H (1) and hookerianamide I (2), along with three known alkaloids N(a)-methylepipachysamine D (3), sarcovagine C (4) and dictyophlebine (5). Their structures were determined with the aid of extensive spectroscopic analysis. All compounds showed good inhibitory activities against the enzymes acetylcholinesterase (IC(50) 2.9-34.1 microM) and butyrylcholinesterase (IC(50) 0.3-3.6 microM). These compounds also showed moderate antiplasmodial activity (IC(50) 2.4-10.3 microM) against the Plasmodium falciparum chloroquine resistant W2 strain.


Assuntos
Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Antimaláricos , Buxaceae/química , Inibidores da Colinesterase , Pregnanos/farmacologia , Esteroides/isolamento & purificação , Esteroides/farmacologia , Animais , Butirilcolinesterase/metabolismo , Resistência a Medicamentos , Espectroscopia de Ressonância Magnética , Plasmodium falciparum/efeitos dos fármacos , Pregnanos/isolamento & purificação , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta
19.
Nat Prod Res ; 21(4): 292-7, 2007 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-17479416

RESUMO

The search for antileishmanial constituents from the medicinal plant Sarcococca hookeriana (Buxaceae) of Nepalese origin has resulted in the isolation of 17 (1-17) active steroidal alkaloids. Compounds 1, 2, and 10 were subjected to derivatization and five chemically derived derivatives (1a, 2a, 10a, 10b, 10c) were also obtained. All these natural compounds and derivatives were found to have potent to mild antileishmanial properties. The IC(50) values were found to be in the range of 0.20-61.44 microg mL(-1) (IC(50) value of standard drug amphotericin B = 0.12 microg mL(-1)). The structure activity relationship indicated that the varieties of functionalities present in ring A of the steroidal alkaloids were found to play a characteristic role to increase the antileishmanial activity.


Assuntos
Alcaloides/química , Alcaloides/farmacologia , Antiprotozoários/química , Antiprotozoários/farmacologia , Buxaceae/química , Leishmania major/efeitos dos fármacos , Esteroides/química , Esteroides/farmacologia , Alcaloides/isolamento & purificação , Animais , Antiprotozoários/isolamento & purificação , Concentração Inibidora 50 , Leishmania major/crescimento & desenvolvimento , Ressonância Magnética Nuclear Biomolecular , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Espectrometria de Massas de Bombardeamento Rápido de Átomos , Esteroides/isolamento & purificação , Relação Estrutura-Atividade
20.
Arch Pharm Res ; 29(11): 990-7, 2006 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-17146968

RESUMO

Sarcococca saligna is a shrub that is traditionally used for its medicinal properties in Pakistan. In this study we report the cardio-suppressant, vasodilator and tracheal relaxant activities of the aqueous-methanolic extract (Ss.Cr) of the plant. Ss.Cr, that tested positive for the presence of saponins, flavonoids, tannins, phenols, and alkaloids, exhibited a dose-dependent (0.3-5 mg/mL) negative inotropic and chronotropic effect on the isolated guinea-pig atrium which was resistant to atropine (1 microM) and aminophylline (10 microM) pretreatment. In rabbit thoracic aorta, Ss.Cr dose-dependently (0.1-3 mg/mL) relaxed the high K+ (80 mM) and phenylephrine (PE, 1 microM)-induced contractions, indicating a possible Ca++ channel blocking (CCB) effect. When tested against PE (1 microM) control peaks in normal Ca++ and Ca++-free Kreb's solution, Ss.Cr exhibited dose-dependent (0.1-3 mg/mL) inhibition, being more potent in relaxing the PE responses in Ca++-free Kreb's solution, thus indicating specific blockade of Ca++ release from the intracellular stores. Ss.Cr also relaxed the agonist-induced contractions in: a) rat aorta irrespective of the presence of endothelium or nitric oxide synthase inhibitor L-NAME and b) rabbit and guinea-pig tracheal strips. The data shows that Ss.Cr possesses possible Ca++ channel blocking activity which might be responsible for its observed cardio-suppressant, vasodilator and tracheal relaxant effects though more tests are required to confirm this Ca++ channel blocking effect.


Assuntos
Antiarrítmicos/farmacologia , Broncodilatadores/farmacologia , Buxaceae/química , Músculo Liso/efeitos dos fármacos , Traqueia/efeitos dos fármacos , Vasodilatadores/farmacologia , Aminofilina/farmacologia , Animais , Atropina/antagonistas & inibidores , Atropina/farmacologia , Bloqueadores dos Canais de Cálcio/farmacologia , Relação Dose-Resposta a Droga , Endotélio Vascular , Inibidores Enzimáticos/farmacologia , Feminino , Cobaias , Átrios do Coração/efeitos dos fármacos , Frequência Cardíaca/efeitos dos fármacos , Técnicas In Vitro , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Antagonistas Muscarínicos/farmacologia , Contração Miocárdica/efeitos dos fármacos , NG-Nitroarginina Metil Éster/farmacologia , Paquistão , Fenilefrina/farmacologia , Extratos Vegetais/farmacologia , Cloreto de Potássio/farmacologia , Coelhos , Ratos , Ratos Sprague-Dawley , Vasoconstritores/farmacologia
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