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1.
Plant Foods Hum Nutr ; 79(1): 73-82, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38006459

RESUMO

Fruits of Syzygium jambos (L.) are recognized as a "food", exhibiting significant antidiabetic activities. However, the α-glucosidase inhibition of the components from Syzygium jambos (L.) have not yet been investigated. In this study, a total of 14 compounds were isolated from Syzygium jambos (L.) Alston, eight of which showed significant inhibitory effects on α-glucosidase, with IC50 values in the range of 0.011-0.665 mM. Notably, compounds 1-3 (IC50: 0.013, 0.011 and 0.030 mM, respectively) exhibited much stronger activity than acarbose (IC50: 2.329 ± 0.109 mM). The enzyme kinetics study indicated that compound 1 was an uncompetitive inhibitor, and compounds 2-8 were mixed-type inhibitors. Moreover, the interactions between compounds and α-glucosidase were investigated by molecular docking, which further revealed that the number of olefin double bonds and 2-COOH of heptadeca-phenols had a notable effect on the α-glucosidase inhibitory activity. This study demonstrated that Syzygium jambos (L.) fruit might serve as a functional food for the prevention of diabetes mellitus.


Assuntos
Syzygium , Syzygium/química , Simulação de Acoplamento Molecular , alfa-Glucosidases/metabolismo , Inibidores Enzimáticos , Análise Espectral , Inibidores de Glicosídeo Hidrolases/farmacologia , Cinética
2.
Front Mol Biosci ; 10: 1331059, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-38250734

RESUMO

The phytoconstituents of the aqueous extract from Syzygium jambos L. (Alston) leaves were defined using HPLC-PDA-MS/MS and the antioxidant, anti-aging, antibacterial, and anti-biofilm activities of the extract were in silico and in vitro investigated. The antioxidant activities were performed using in vitro DPPH and FRAP assays as well as H2-DCFDA assay in HaCaT cells in which oxidative stress was induced by UVA radiation. Anti-aging activity was tested in vitro, using aging-related enzymes. The antibacterial, anti-biofilm and inhibitory effects on bacterial mobilities (swarming and swimming) were assessed against Pseudomonas aeruginosa. Results showed that S. jambos aqueous extract contained 28 phytochemicals belonging to different metabolite classes, mainly phenolic acids, gallic acid derivatives, flavonoids, and ellagitannins. Mineral content analysis showed that S. jambos leaves contained moderate amounts of nitrogen, potassium, manganese, magnesium, and zinc, relatively low amounts of phosphorus and copper, and high concentration of calcium and iron. The extract displayed strong antioxidant activities in vitro and inhibited UVA-induced oxidative stress in HaCaT cells. Docking the major compounds identified in the extract into the four main protein targets involved in skin aging revealed an appreciable inhibitory potential of these compounds against tyrosinase, elastase, hyaluronidase, and collagenase enzymes. Moreover, molecular dynamic simulations were adopted to confirm the binding affinity of some selected compounds towards the target enzymes. The extract exhibited pronounced in vitro anti-aging effects, compared to kojic acid and quercetin (the reference compounds). It also inhibited the growth of P. aeruginosa, counteracted its ability to form biofilm, and impeded its swarming and swimming mobilities. Altogether, these findings strongly propose S. jambos leaves as a promising source of bioactive metabolites for the development of natural cosmeceutical and dermatological agents.

3.
Food Chem ; 396: 133668, 2022 Dec 01.
Artigo em Inglês | MEDLINE | ID: mdl-35849981

RESUMO

The chemical characteristics and hypolipidemic effects of alkylphenols in the fruit of Syzygium jambos were investigated in this study. Three cardanols (1-3; 1 as a new compound) and three alkylresorcinols (4-6) were isolated and identified from S. jambos fruit. Cardanols 1 and 2 (10-40 µM) suppressed lipids accumulation and reduced triglyceride content in oleic acid-overloaded HepG2 cells via the activation of AMPK/PPARα signaling pathways. Furthermore, the biological distribution of cardanols after an oral intake in mice was investigated. Compound 2 was detected in mice plasma, feces, and adipose tissues after a single oral intake (80 mg/kg body weight). In addition, an alkylphenols-enriched S. jambos fruit extract containing two bioactive compounds (95.9 and 198.6 µg/mg of compounds 1 and 2, respectively) was prepared. Findings from the current study highlight the potential usage of cardanols as well as S. jambos fruit for the management of dyslipidemia.


Assuntos
Syzygium , Animais , Frutas/química , Lipídeos/análise , Camundongos , Extratos Vegetais/química , Syzygium/química
4.
Molecules ; 27(9)2022 Apr 20.
Artigo em Inglês | MEDLINE | ID: mdl-35565998

RESUMO

Macaranga tanarius (MT) and Syzygium jambos (SJ) are pharmacologically reported to have anti-oxidant, anti-inflammatory, and anti-diabetic effects, and can be neuroprotective agents. Our previous work revealed that MT and SJ exhibited 76.32% and 93.81% inhibition against acetylcholinesterase (AChE) at 50 µg/mL final concentration in their ethyl acetate and hexane fractions, respectively. This study was aimed to investigate the bioactive constituents of MT and SJ and their molecular mechanism toward AChE inhibition. Bioassay-guided isolation afforded prenylflavonoids 1-3 from MT and anacardic acid derivatives 4 and 5 from SJ that were confirmed by NMR and MS data. Compound 5 exerted the strongest anti-AChE potential (IC50: 0.54 µM), followed by 1, 4, 3, and 2 (IC50: 1.0, 2.4, 6.8, and 33 µM, respectively). In silico molecular docking revealed 5 formed stronger molecular interactions including three H-bonds than its derivative 4 based on the saturation of their alkyl chains. The addition of a five carbon-prenyl chain in 1 increased the number of binding interactions, justifying its greater activity than derivatives 2 and 3. This research reflects the first report of AChE inhibitors from these species, thereby adding pharmacological values to MT and SJ as potential remedies in neuroprotection.


Assuntos
Euphorbiaceae , Syzygium , Acetilcolinesterase/metabolismo , Anti-Inflamatórios , Inibidores da Colinesterase/química , Inibidores da Colinesterase/farmacologia , Euphorbiaceae/metabolismo , Simulação de Acoplamento Molecular , Syzygium/química
5.
BMC Complement Med Ther ; 22(1): 101, 2022 Apr 07.
Artigo em Inglês | MEDLINE | ID: mdl-35392889

RESUMO

BACKGROUND: Disordered endothelial cell activation plays an important role in the pathophysiology of atherosclerosis, cancer, sepsis, viral infections, and inflammatory responses. There is interest in developing novel therapeutics to regulate endothelial cell function in atherothrombotic, metabolic, vascular, and hematological diseases. Extracts from leaves of the Syzygium jambos (L.) Alston (S. jambos) trees have been proposed to treat cardiovascular diseases and diabetes through unclear mechanisms. We investigated the effects of the S. jambos extract on biomarkers of endothelial dysfunction and immune responses in the human endothelial cell line, EA.hy926. METHODS: Leaves of S. jambos were collected, concocted and lyophilized. To study the effects of S. jambos on endothelial cell activation, we used the human endothelial cell line. IL-6 levels were measured using qPCR and ELISA. PDI activity was measured using Insulin Turbidity and Di-E-GSSG assays. CM-H2DCFDA was used to study ROS levels. Migration assay was used to study S. jambos effect on ex vivo human polymorphonuclear and human mononuclear cells. RESULTS: Our results show that incubation of EA.hy926 cells with ET-1 led to a 6.5 ± 1.6 fold increase in IL-6 expression by qPCR, an event that was blocked by S. jambos. Also, we observed that ET-1 increased extracellular protein disulfide isomerase (PDI) activity that was likewise dose-dependently blocked by S. jambos (IC50 = 14 µg/mL). Consistent with these observations, ET-1 stimulated ex vivo human polymorphonuclear and mononuclear cell migration that also was dose-dependently blocked by S. jambos. In addition, ET-1 stimulation led to significant increases in ROS production that were sensitive to S. jambos. CONCLUSION: Our results suggest that the S. jambos extract represents a novel cardiovascular protective pharmacological approach to regulate endothelial cell activation, IL-6 expression, and immune-cell responses.


Assuntos
Syzygium , Biomarcadores , Células Endoteliais , Humanos , Interleucina-6 , Extratos Vegetais/farmacologia , Espécies Reativas de Oxigênio
6.
Front Pharmacol ; 13: 786712, 2022.
Artigo em Inglês | MEDLINE | ID: mdl-35177986

RESUMO

Medicinal plants have been used since ancient times for human healthcare as drugs, spices, and food additives. The progress in technology and medicine observed, the last decades, has improved the quality of life and healthcare but with worrisome drawbacks. Side effects caused by synthetic drugs for instance originate sometimes irreversible health disorders. Natural substances, in contrast, are biologically and environmentally friendly. Syzygium jambos L. (Alston) also known as rose apple conveys a long history as essential traditional medicine with a broad spectrum of application in various cultures. The plant discloses a diverse group of secondary metabolites and extracts that displayed major susceptibilities towards various health concerns especially stress-related and inflammatory diseases. Despite a rich literature about the plant, the chemistry and biology of S. jambos have not been comprehensively reviewed yet. Accordingly, we present herein a literature survey of rose apple which aims to draw the chemical identity of the plant and establish a consistent discussion on the respective biological application of plant extracts and their corresponding traditional uses. The present work could provide a scientific basis for future studies and necessary information for further investigations of new drug discovery.

7.
Biomed Pharmacother ; 142: 112085, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34463263

RESUMO

The protective effect of Syzygium jambos (SJ) bark extract against streptozotocin-induced diabetes was tested in rats. Animals were treated with 100 or 200 mg/kg of the extract or glibenclamide, 0.5 mg/kg per os, once daily: started 2 days before streptozotocin (STZ) injection and lasted for 14 days after STZ injection. The effect of the extract was also evaluated on normal rats in comparison with glibenclamide. Diabetic animals showed an elevated blood glucose level, positive glycosuria, elevated fructosamine, pancreatic malondialdehyde, pancreatic TNF-a, and pancreatic caspase-3 levels and decreased serum insulin, pancreatic IL-10, pancreatic BCL-2, reduced glutathione (GSH), liver insulin substrate-2, liver phosphorylated protein kinase B (p-AKT) and liver glucose transporter 4 (GLUT4) levels. Histopathological examination of diabetic rats revealed islets destruction and vacuolation and collagen fibers deposition. All these changes were mitigated dose dependently by the extract. The high dose of the extract exerted comparable effects with glibenclamide in most studied parameters. These results indicated the protective role of SJ against the STZ diabetogenic action. In the pancreatic and hepatic tissue of diabetic rats, SJ effectively recovered pancreatic cells by reducing hyperglycemia through activating endogenous antioxidants, dynamic insulin production, and suppressing inflammation and apoptosis. The observed results might be attributed to the existence of 10 secondary metabolites as annotated by LC-MS. Taken together, S. jambos is a potential candidate for further studies to confirm its activities as a therapeutic agent for diabetic patients.


Assuntos
Diabetes Mellitus Experimental/tratamento farmacológico , Hipoglicemiantes/farmacologia , Extratos Vegetais/farmacologia , Syzygium/química , Animais , Apoptose/efeitos dos fármacos , Diabetes Mellitus Experimental/fisiopatologia , Relação Dose-Resposta a Droga , Transportador de Glucose Tipo 4/metabolismo , Glibureto/farmacologia , Hipoglicemiantes/administração & dosagem , Inflamação/tratamento farmacológico , Inflamação/patologia , Proteínas Substratos do Receptor de Insulina/metabolismo , Fígado/efeitos dos fármacos , Fígado/metabolismo , Masculino , Estresse Oxidativo/efeitos dos fármacos , Pâncreas/efeitos dos fármacos , Pâncreas/patologia , Extratos Vegetais/administração & dosagem , Proteínas Proto-Oncogênicas c-akt/metabolismo , Ratos , Ratos Wistar , Transdução de Sinais/efeitos dos fármacos , Estreptozocina
8.
China Pharmacy ; (12): 3246-3251, 2019.
Artigo em Chinês | WPRIM (Pacífico Ocidental) | ID: wpr-817425

RESUMO

OBJECTIVE: To compare inhibitory effects of ethanol extract of different medicinal parts (root, stem, leaf, seed, flower and flesh) from Syzygium jambos on the activities of α-glycosidase and α-amylase. METHODS: Using half-inhibitory concentration value (IC50) as evaluation index, acarbose as positive control, inhibitory effects of ethanol extract of different medicinal parts from S. jambos on the activities of α-glycosidase (from yeast and small instestine in mice) and α-amylase were evaluated with in vitro inhibition model. The enzymatic dynamics and Lineweaver-Burk methods were used to analyze the inhibitory type of the best medicinal part on the activities of α-glycosidase and α-amylase. RESULTS: In the yeast α-glucosidase inhibitory activity test, the order of inhibitory activity was S. jambos seed>S. jambos stem>S. jambos leaf>S. jambos root>S. jambos flower>S. jambos flesh>acarbose. In the mice intestine α-glucosidase inhibitory activity test, the order of inhibitory activity was S. jambos seed>S. jambos stem>S. jambos root>S. jambos leaf>S. jambos flower>S. jambos flesh>acarbose. In the α-amylase inhibitory activity test, the order of inhibitory activity was acarbose>S. jambos seed>S. jambos stem>S. jambos root>S. jambos leaf>S. jambos flesh>S. jambos flower. Ethanol extract of S. jambos seed had the stronger inhibition activity against α-glucosidase from yeast,α-glucosidase from small intestine in mice and α-amylase than other medicinal parts [IC50 were(6.64±0.24), (32.77±2.46) and (41.18±1.63) μg/mL]. Ethanol extract of S. jambos seed had the stronger inhibition activity against α-glucosidase than acarbose [IC50 to α-glucosidase from yeast and α-glucosidase from small intestine in mice were (2 833.33±5.48), (1 304.21±6.45) μg/mL] (P<0.05). The inhibitory effect of ethanol extract from S. jambos on the activity of α-amylase was less than that of acarbose [IC50 was (27.27±1.24) μg/mL] (P<0.05). Enzymatic dynamics showed that the inhibitory type of ethanol extract from S. jambos seed on α-glucosidase and α-amylase were both reversible competitive inhibition. CONCLUSIONS: Among different parts of S. jambos such as root, stem, leaf, seed, flower and flesh, S. jambos seed shows the strongest inhibitory effects on the activities of α-glucosidase and α-amylase, which has the value of being developed for the treatment of diabetes or health food.

9.
J Food Sci Technol ; 55(11): 4432-4439, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-30333639

RESUMO

Excessive production and restricted elimination of free radicals like superoxide, hydroxyl radical (·OH), anion radical (O2 ·-), and non-radical hydrogen peroxide (H2O2) are related to the development of cancer, arteriosclerosis, arthritis and neurodegenerative diseases. According to a report of World Health Organisation, about 80% of the population living in the developing countries predominantly depends on the traditional medicine for their primary healthcare. Plants possess innate ability to synthesize a wide variety of enzymatic and non-enzymatic antioxidants capable of attenuating ROS-induced oxidative damage. The ethanolic leaf extracts of Syzygium jambos L. and Terminalia citrina Roxb. exhibited a significant in vitro antioxidant activity when compared with natural antioxidant, ascorbic acid. The extracts also provided strong cellular protection against the damaging effects of H2O2 induced oxidative stress in the mutant strains (tsa1Δ and sod1Δ) of Saccharomyces cerevisiae. The GC-MS analysis of the leaf extracts revealed the presence of phytoconstituents majorly constituting of terpenes, vitamin and fatty acids contributing to the antioxidant property. The plant extracts may serve as a potential source of exogenous antioxidants to combat the undesirable effects of oxidative stress.

10.
Int J Biol Macromol ; 118(Pt B): 1414-1421, 2018 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-30170360

RESUMO

Jambo is a tropical fruit cultivated in Southeast Asia and tropical regions of America and Africa. After extraction, its polysaccharides were structurally characterized. Water soluble polysaccharides (WSP) were composed of GalA:Ara:Gal:Glc:Rha in 51:22:16:5:6 molar ratio, indicating the presence of pectic polysaccharides. Methylation analysis and NMR spectroscopy indicated the presence of homogalacturonan (HG), type II arabinogalactan and type I rhamnogalacturonan (RG-I). The HG/RG-I ratio was 88%, indicating greater amounts of smooth than hairy pectic regions. Hemicellulosic polysaccharides were extracted from the residue and fractionated by freeze-thaw procedure in two fractions (ASP-S and ASP-I). ASP-S was composed of Glc:Gal:Xyl:Ara:Man:Fuc:UA in a 45:16:20:3:8:5:2 molar ratio. Methylation analysis and 13C NMR spectroscopy indicated xyloglucan, xylan and mannan. Their relative proportion estimated on sugar linkage was 89%, 6% and 3%, respectively. ASP-I was composed mainly of xylose (99.5%) and its 13C NMR indicated a linear (1 → 4)-ß-D-xylan. The biological activity of WSP was tested in Ehrlich tumor-bearing mice. After 21 days of oral treatment, the doses of 150 and 250 mg/kg WSP reduced expressively the tumor growth, similarly to the positive control methotrexate, and improved the body weight of tumor-bearing mice. Further studies are necessary to investigate the mechanisms of the WSP antitumor effect.


Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Pectinas/química , Pectinas/farmacologia , Syzygium/química , Animais , Antineoplásicos/isolamento & purificação , Feminino , Glicosídeos/química , Camundongos , Pectinas/isolamento & purificação , Polissacarídeos/química , Polissacarídeos/isolamento & purificação , Polissacarídeos/farmacologia
11.
Biomed Pharmacother ; 91: 567-580, 2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-28486189

RESUMO

In the present study, we are reporting antimalarial potential of silver (AgNPs) and gold (AuNPs) nanoparticles synthesized by leaf and bark extract of Syzygium jambos (L.) Alston (Myrtaceae). AuNPs and AgNPs obtained by both the extracts were characterized using UV-vis spectroscopy, zeta potential, transmission electron microscopy (TEM), X-ray diffraction (XRD), and Fourier Transform Infrared spectroscopy (FTIR). NMR and FTIR spectra indicate that the saccharides and phenolics present in the S. jambos extracts were the major contributors responsible for the synthesis and stabilization of NPs. NPs were also synthesized by chemical methods and were compared for their antiplasmodial potential against chloroquine sensitive (3D7) and resistant (Dd2) strain of Plasmodium falciparum by using 24h schizont maturation assay. AgNPs synthesized by both the extracts showed higher antiplasmodial activity than the rest. Further, NPs synthesized by S. jambos extracts have shown insignificant cytotoxicity against human cervical cancer cell line (HeLa) and rat skeletal muscle cell line (L6), which proved their biocompatibility.


Assuntos
Antimaláricos/farmacologia , Ouro/farmacologia , Química Verde/métodos , Nanopartículas Metálicas/química , Prata/farmacologia , Animais , Células HeLa , Humanos , Concentração de Íons de Hidrogênio , Nanopartículas Metálicas/ultraestrutura , Tamanho da Partícula , Plasmodium falciparum/efeitos dos fármacos , Ratos , Sorbitol/farmacologia , Espectroscopia de Infravermelho com Transformada de Fourier , Eletricidade Estática , Syzygium/química , Temperatura , Fatores de Tempo , Difração de Raios X
12.
APMIS ; 125(5): 482-490, 2017 May.
Artigo em Inglês | MEDLINE | ID: mdl-28294414

RESUMO

Virulence factors regulated by quorum sensing (QS) play a critical role in the pathogenesis of an opportunistic human pathogen, Pseudomonas aeruginosa in causing infections to the host. Hence, in the present work, the anti-virulence potential of the medicinal plant extracts and their derived phytochemicals from Myrtaceae family was evaluated against P. aeruginosa. In the preliminary screening of the tested medicinal plant extracts, Syzygium jambos and Syzygium antisepticum demonstrated a maximum inhibition in QS-dependent violacein pigment production by Chromobacterium violaceum DMST 21761. These extracts demonstrated an inhibitory activity over a virulence factor, pyoverdin, production by P. aeruginosa ATCC 27853. Gas chromatography-mass spectrometric (GC-MS) analysis revealed the presence of 23 and 12 phytochemicals from the extracts of S. jambos and S. antisepticum respectively. Three top-ranking phytochemicals, including phytol, ethyl linoleate and methyl linolenate, selected on the basis of docking score in molecular docking studies lowered virulence factors such as pyoverdin production, protease and haemolytic activities of P. aeruginosa to a significant level. In addition, the phytochemicals reduced rhamnolipid production by the organism. The work demonstrated an importance of plant-derived compounds as anti-virulence drugs to conquer P. aeruginosa virulence towards the host.


Assuntos
Antibacterianos/farmacologia , Redes e Vias Metabólicas/efeitos dos fármacos , Compostos Fitoquímicos/farmacologia , Extratos Vegetais/farmacologia , Pseudomonas aeruginosa/efeitos dos fármacos , Syzygium/química , Fatores de Virulência/metabolismo , Antibacterianos/isolamento & purificação , Chromobacterium/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas , Glicolipídeos/metabolismo , Humanos , Simulação de Acoplamento Molecular , Compostos Fitoquímicos/isolamento & purificação , Extratos Vegetais/isolamento & purificação , Plantas Medicinais/química
13.
BMC Res Notes ; 9: 191, 2016 Mar 28.
Artigo em Inglês | MEDLINE | ID: mdl-27021114

RESUMO

BACKGROUND: Syzygium jambos has been used as a traditional medicine for the treatment of inflammatory diseases in Bangladesh. The study investigates the high performance liquid chromatography (HPLC) profiling of phenolic compounds, and evaluates the antioxidant and anti-inflammatory activities of ethanol extract of S. jambos available in Bangladesh. METHODS: The extract was subjected to HPLC for the identification and quantification of the major bioactive polyphenols present in S. jambos. Antioxidant activity was determined using 2, 2'-azino bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical scavenging, reducing power assay, total antioxidant capacity, total phenolic and flavonoid content. Furthermore, the anti-inflammatory effect of the extract in rats for two different test models: carrageenan and histamine-induced paw edema was inspected. RESULTS: High levels of catechin hydrate and rutin hydrate (99.00 and 79.20 mg/100 g extract, respectively) and moderate amounts of ellagic acid and quercetin (59.40 and 69.30 mg/100 g extract, respectively) were quantified in HPLC. Catechin hydrate from this plant extract was determined for the first time through HPLC. For ABTS scavenging assay, the median inhibition concentration (IC50) value of S. jambos was 57.80 µg/ml, which was significant to that of ascorbic acid (12.01 µg/ml). The maximum absorbance for reducing power assay was found to be 0.4934. The total antioxidant capacity, phenolic and flavonoid contents were calculated to be 628.50 mg/g of ascorbic acid, 230.82 mg/g of gallic acid and 11.84 mg/g of quercetin equivalent, respectively. At a dose of 400 mg/kg, a significant acute anti-inflammatory activity (P < 0.01) was observed in rats for both the test models with a reduction in the paw volume of 58.04 and 53.95 %, in comparison to those of indomethacin (62.94 and 65.79 %), respectively. CONCLUSIONS: The results suggest that the phenolic and flavonoid compounds are responsible for acute anti-inflammatory and antioxidant activities of S. jambos.


Assuntos
Anti-Inflamatórios/farmacologia , Antioxidantes/análise , Cromatografia Líquida de Alta Pressão/métodos , Etanol/química , Extratos Vegetais/farmacologia , Syzygium/química , Animais , Anti-Inflamatórios/uso terapêutico , Ácido Ascórbico/farmacologia , Bangladesh , Benzotiazóis/farmacologia , Edema/tratamento farmacológico , Flavonoides/análise , Sequestradores de Radicais Livres/farmacologia , Histamina , Indometacina/farmacologia , Indometacina/uso terapêutico , Masculino , Oxirredução , Extratos Vegetais/uso terapêutico , Polifenóis/análise , Ratos Wistar , Ácidos Sulfônicos/farmacologia
14.
J Agric Food Chem ; 63(47): 10257-62, 2015 Dec 02.
Artigo em Inglês | MEDLINE | ID: mdl-26554667

RESUMO

Seven new phloroglucinol derivatives (1-7) were isolated from the fruit tree Syzygium jambos together with four known triterpenoids (8-11) and two known flavones (12 and 13). According to the spectroscopic analyses (infrared, electrospray ionization mass spectrometry (ESIMS), high-resolution ESIMS, 1D and 2D nuclear magnetic resonance), the structures of compounds 1-7 were elucidated as jambone A (1), jambone B (2), jambone C (3), jambone D (4), jambone E (5), jambone F (6), and jambone G (7). All the isolates were determined for their cytotoxic activities on melanoma cells by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, and compounds 10 and 11 showed potent activities. Moreover, compounds 1, 2, 4-7, 12, and 13 exhibited weak antioxidant activities under ferric-reducing antioxidant power and 2,2-diphenyl-1-picryhydrazyl radical-scavenging assays.


Assuntos
Floroglucinol/química , Extratos Vegetais/química , Syzygium/química , Frutas/química , Estrutura Molecular , Floroglucinol/toxicidade , Extratos Vegetais/toxicidade
15.
Redox Rep ; 19(5): 206-13, 2014 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-24725132

RESUMO

OBJECTIVE: This study aimed to investigate the effect of the leaf extracts of Syzygium jambos and Solanum guaraniticum on the δ-aminolevulinate dehydratase (δ-ALA-D) activity, their antioxidant activity and potential protective action on oxidatively stressed erythrocytes, in order to demonstrate the safety or toxicity of the plant. METHODS: In erythrocyte samples, the effect of both extracts on δ-ALA-D activity, H2O2-induced oxidative stress, and 2,2'azobis (2-amidinopropane) (AAPH)-induced hemolysis was evaluated, as well as some antioxidant mechanisms. RESULTS: Both extracts inhibited δ-ALA-D activity (S. guaraniticum > S. jambos), and an involvement of the zinc ion of the δ-ALA-D structure on the inhibition of enzyme activity was verified. S. jambos leaf extract showed marked efficiency in countering H2O2-induced lipid peroxidation and in maintaining cellular integrity against AAPH-induced hemolysis. Furthermore, S. jambos exhibited greater H2O2 scavenging activity and stronger reduction power than S. guaraniticum. DISCUSSION: Both extracts bear potent antioxidant property as an important beneficial effect. However, the inhibition of δ-ALA-D activity suggests a possible harmful effect of these vegetal preparations and indicates the need for further investigation regarding their toxicological properties. All together, these data represent a significant contribution to the knowledge of these plants, both to the scientific community and to the folk medicine.


Assuntos
Eritrócitos/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/farmacologia , Folhas de Planta/química , Sintase do Porfobilinogênio/metabolismo , Solanum/química , Syzygium/química , Amidinas/farmacologia , Antioxidantes/metabolismo , Eritrócitos/enzimologia , Hemólise/efeitos dos fármacos , Humanos , Peróxido de Hidrogênio/farmacologia , Peroxidação de Lipídeos/efeitos dos fármacos , Oxidantes/farmacologia , Oxirredução
16.
Acta Crystallogr Sect E Struct Rep Online ; 70(Pt 12): o1242-3, 2014 Dec 01.
Artigo em Inglês | MEDLINE | ID: mdl-25553022

RESUMO

The title compound [systematic name: 3ß-hy-droxy-lup-20(29)-en-28-oic acid methanol monosolvate], C30H48O3·CH3OH, is a solvent pseudopolymorph of a naturally occurring plant-derived lupane-type penta-cyclic triterpenoid, which was isolated from the traditional Chinese medicinal plant Syzygium jambos (L.) Alston. The dihedral angle between the planes of the carb-oxy-lic acid group and the olefinic group is 12.17 (18)°. The A/B, B/C, C/D and D/E ring junctions are all trans-fused. In the crystal, O-H⋯O hydrogen bonds involving the hy-droxy and carb-oxy-lic acid groups and the methanol solvent mol-ecule give rise to a two-dimensional network structure lying parallel to (001).

17.
Artigo em Chinês | WPRIM (Pacífico Ocidental) | ID: wpr-854451

RESUMO

Objective: To study the chemical constituents from the stems of Syzygium jambos var. jambos. Methods: The phyotchemicals were isolated by using various chromatographic techniques such as silica gel, Sephadex LH-20, alumina column chromatography, and preparative HPLC process. The structures were elucidated on the basis of spectral data analysis. Their cytotoxicity against human liver cancer cells Huh-7 was conducted using MTT assay. Results: Twelve compounds were isolated from the EtOAc and MeOH extracts in the stems of S. jambos and identified as alphitolic acid (1), urolithin A (2), dibutyl phthalate (3), betulinic acid (4), ursolic acid (5), 1-(4-methoxyphenyl)-1, 2-propanediol (6), 2, 6-dimethoxy-1, 4-benzoquinone (7), diisobutyl phthalate (8), β-sitosterol (9), 3-acetyl-ursolic acid (10), asiatic acid (11), and arjunolic acid (12), respectively. All tested compounds 1, 7, 10, and 11 + 12 mixture did not show the cytotoxic activities towards human tumor cells Huh-7 in the test range up to 50 μmol/L. Conclusion: Except compound 4, the other 11 compounds are obtained from this plant for the first time. All tested compounds exhibit no significant cytotoxic activity against Huh-7 cells.

18.
Ayu ; 34(3): 305-8, 2013 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-24501529

RESUMO

Hepatoprotective activity of methanolic extract of Syzygium jambos (Alston) (Linn.) leaves against Paracetamol-induced hepatic damage in Wistar albino rats was observed at two different doses, 100 and 200 mg/kg body weight. The healthy control, disease control, and standard drug Silymarin-treated groups were also maintained for the comparison. The liver marker enzymes SGOT, SGPT, ALKP, Serum Bilirubin and other metabolic parameters like total cholesterol, HDL-cholesterol were evaluated in all the experimental groups. The changes in liver function parameters were significant in comparison to disease control group and the observed efficacy was comparable to standard drug. The efficacy of the extract was found to be dose dependent. The histopathology study of liver also supports the presence of hepatoprotective activity in S. jambos by showing improved cytoarchitecture of liver cells in the treated groups. The results obtained in this study indicate necessity for further research on isolation and characterization of functional molecules from the extract.

19.
Pharmacognosy Res ; 2(1): 4-9, 2010 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-21808530

RESUMO

Methanol extracts from S. jambos leaves were tested for antimicrobial activity and toxicity. S. jambos leaf extract inhibited the growth of 4 of the 14 bacteria tested (29%). Both gram-positive and gram-negative bacterial growths were inhibited by S. jambos leaf extract, although gram-positive bacteria appeared more susceptible. Two of the 10 gram-negative bacteria (20%) and 2 of the 4 gram-positive bacteria (50%) tested had their growths inhibited by the extract. The leaf extract also proved to be toxic in the Artemia franciscana bioassay, with a 48-h LC(50) of 387.9 ± 38.8 µg/mL, making it slightly more toxic than Mevinphos (505.3± 37.7 µg/mL) and approximately 5-fold less toxic than potassium dichromate (80.4 ± 4.3 µg/mL). Whilst potassium dichromate's LC(50) remained constant across the 72-hour test period (24-h LC(50), 86.3 ± 5.1; 72-h LC(50), 77.9 ± 4.9), the extract and Mevinphos LC(50) values decreased by 72 hours (87.0 ± 11.3 µg/mL and 103.9 ± 12.8 µg/mL, respectively), indicating their similar levels of toxicity in the assay.

20.
Rev. bras. farmacogn ; 19(1a): 89-94, Jan.-Mar. 2009. tab
Artigo em Português | LILACS | ID: lil-522427

RESUMO

Syzygium jambos (L.) Alston, Myrtaceae, é empregado na medicina popular como digestivo e antiinflamatório. A triagem fitoquímica da droga pulverizada (folhas) indicou a presença de flavonóides, taninos e óleo volátil. O extrato hidroetanólico a 70 por cento das folhas de S. jambos foi preparado por percolação e liofilizado. O conteúdo de taninos das folhas e do extrato foi calculado, respectivamente, em 21,9 por cento e 43,3 por cento. O teor de flavonóides foi de 0,6 por cento (folhas) e 1,2 por cento (extrato). A administração oral prévia do extrato (400 mg/kg) a ratos Wistar reduziu significativamente as lesões gástricas induzidas por etanol acidificado. No modelo de úlcera subcrônica, com indução de lesão gástrica utilizando ácido acético a 30 por cento, o tratamento com o extrato (400 mg/kg) não apresentou resultado significativo. A atividade antioxidante do extrato foi avaliada através dos modelos de lipoperoxidação e de medida de capacidade seqüestrante de radicais DPPH. Os valores obtidos de Q1/2 (MDA) e CE50 (DPPH) foram, respectivamente, 0,17 μg/mL e 5,68 μg/mL.


Syzygium jambos (L.) Alston, Myrtaceae, is commonly employed in folk medicine as digestive and anti-inflammatory. Phytochemical screening of the powdered dried leaves indicates the presence of flavonoids, tannins and essential oil. Hydroethanol extracts (70 percent) were prepared by percolation and freeze-drying. The tannin content of dried leaves and extract was, respectively, 21.9 percent and 43.3 percent. The flavonoid content was 0.6 percent (dried leaves) and 1.2 percent (extract). Previous oral administration of S. jambos leaves extract (400 mg/kg) to rats reduced significantly gastric injury induced by HCl/ethanol. At the subcronic ulcer model by induction with 30 percent acetic acid the results were not significant. In vitro antioxidant activity of S. jambos extract was evaluated by malondialdehyde (MDA) and DPPH free radical method. The Q1/2 for MDA assay was 0.17 μg/mL and the EC50 for DPPH assay was 5.68 μg/mL.

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