RESUMEN
Thirteen new sesquiterpenoid glycoside esters, including 11 aromadendrane-type compounds, pitqinlingosides A-K (1-11), one cadinane-type compound, pitqinlingoside L (12), and one eudesmane-type compound, pitqinlingoside M (13), together with seven known analogues (14-20) were isolated from the twigs, fruits, and leaves of Pittosporum qinlingense. Structures were elucidated by analysis of spectroscopic data, gas chromatography mass spectrometry (GC-MS), and chemical methods. The absolute configuration was confirmed by single-crystal X-ray crystallography analysis or electronic circular dichroism spectra. Unusual glycoside esters are characterized by the presence of polyacylated ß-d-fucopyranosyl, ß-d-glucopyranosyl, and ß-d-xylopyranosyl units. Pitqinlingosides A (1), B (2), D (4), and F (6), pittosporanoside A1 acetate (14), and pittosporanoside A1 (16) showed significant nitric oxide production inhibition in lipopolysaccharide (LPS)-induced BV-2 microglial cells with IC50 values ranging from 0.95 to 24.12 µM. Structure-activity relationships of the isolated compounds are discussed.
Asunto(s)
Antiinflamatorios/farmacología , Microglía/efectos de los fármacos , Rosales/química , Sesquiterpenos/química , Sesquiterpenos/farmacología , Animales , Antiinflamatorios/química , Cristalografía por Rayos X , Ésteres/química , Glucósidos/química , Lipopolisacáridos/farmacología , Ratones , Microglía/metabolismo , Estructura Molecular , Óxido Nítrico/biosíntesis , Análisis Espectral/métodos , Relación Estructura-ActividadRESUMEN
Four oleanane-type glycosides were isolated from a horticultural cultivar "Green Elf" of the endemic Pittosporum tenuifolium (Pittosporaceae) from New Zealand: three acylated barringtogenol C glycosides from the leaves, with two previously undescribed 3-O-ß-d-glucopyranosyl-(1â2)-[α-l-arabinopyranosyl-(1â3)]-ß-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, 3-O-ß-d-galactopyranosyl-(1â2)-[α-l-arabinopyranosyl-(1â3)]-ß-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, and the known 3-O-ß-d-glucopyranosyl-(1â2)-[α-l-arabinopyranosyl-(1â3)]-ß-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C (Eryngioside L). From the roots, the known 3-O-ß-d-glucopyranosyl-(1â2)-ß-d-galactopyranosyl-(1â2)-ß-d-glucuronopyranosyloleanolic acid (Sandrosaponin X) was identified. Their structures were elucidated by spectroscopic methods including 1D- and 2D-NMR experiments and mass spectrometry (ESI-MS). According to their structural similarities with gymnemic acids, the inhibitory activities on the sweet taste TAS1R2/TAS1R3 receptor of an aqueous ethanolic extract of the leaves and roots, a crude saponin mixture, 3-O-ß-d-glucopyranosyl-(1â2)-[α-l-arabinopyranosyl-(1â3)]-ß-d-glucuronopyranosyl-21-O-angeloyl-28-O-acetylbarringtogenol C, and Eryngioside L were evaluated.
Asunto(s)
Rosales/química , Saponinas/aislamiento & purificación , Triterpenos/aislamiento & purificación , Subunidades alfa de la Proteína de Unión al GTP Gq-G11/antagonistas & inhibidores , Células HEK293 , Humanos , Espectroscopía de Resonancia Magnética , Estructura Molecular , Nueva Zelanda , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Hojas de la Planta/química , Raíces de Plantas/química , Plantas Medicinales/química , Receptores Acoplados a Proteínas G/antagonistas & inhibidores , Saponinas/química , Saponinas/farmacología , Espectrometría de Masa por Ionización de Electrospray , Triterpenos/química , Triterpenos/farmacologíaRESUMEN
This study investigated the in vitro inhibitory potential of different solvent extracts of leaves of Barbeya oleoides on key enzymes related to type 2 diabetes mellitus (α-glucosidase and α-amylase) in combination with an aggregation assay (using 0.01% Triton X-100 detergent) to assess the specificity of action. The methanol extract was the most active in inhibiting α-glucosidase and α-amylase, with IC50 values of 6.67 ± 0.30 and 25.62 ± 4.12 µg/mL, respectively. However, these activities were significantly attenuated in the presence of 0.01% Triton X-100. The chemical analysis of the methanol extract was conducted utilizing a dereplication approach combing LC-ESI-MS/MS and database searching. The chemical analysis detected 27 major peaks in the negative ion mode, and 24 phenolic compounds, predominantly tannins and flavonol glycosides derivatives, were tentatively identified. Our data indicate that the enzyme inhibitory activity was probably due to aggregation-based inhibition, perhaps linked to polyphenols.
Asunto(s)
Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/farmacología , Inhibidores de Glicósido Hidrolasas/química , Inhibidores de Glicósido Hidrolasas/farmacología , Rosales/química , Metabolismo de los Hidratos de Carbono/efectos de los fármacos , Diabetes Mellitus Tipo 2/tratamiento farmacológico , Evaluación Preclínica de Medicamentos , Inhibidores Enzimáticos/aislamiento & purificación , Flavonoides/química , Flavonoides/aislamiento & purificación , Flavonoides/farmacología , Inhibidores de Glicósido Hidrolasas/aislamiento & purificación , Humanos , Hipoglucemiantes/química , Hipoglucemiantes/aislamiento & purificación , Hipoglucemiantes/farmacología , Técnicas In Vitro , Fitoquímicos/química , Fitoquímicos/farmacología , Fitoterapia , Extractos Vegetales/química , Extractos Vegetales/farmacología , Hojas de la Planta/química , Plantas Medicinales/química , Polifenoles/química , Polifenoles/aislamiento & purificación , Polifenoles/farmacología , Espectrometría de Masa por Ionización de Electrospray , Espectrometría de Masas en Tándem , alfa-Amilasas/antagonistas & inhibidoresRESUMEN
Three non-conventional extraction techniques (enzyme-assisted with cellulase, citric acid ultrasound-assisted and enzyme-ultrasound-assisted treatment) and conventional citric acid extraction were applied to obtain pectin from raspberry, blueberry, strawberry and redcurrant, and were compared in terms of extraction yields and physicochemical properties of the extracted pectins. Except for pectin from raspberry, conventional citric acid extraction led to the highest extraction yield (~8%) and, for the same berries, the lowest pectin recovery was found for the extraction with cellulase (~4%). Regarding the structural characteristics of pectins, enzymatically extracted pectins from redcurrant and strawberry exhibited the highest levels of galacturonic acid (≥73%) whereas, in general, this monosaccharide was found from 51 to 69% in the rest of samples. Although, ultrasound-assisted extraction did not improve pectin yield, it minimized the levels of "non-pectic" components leading to the obtainment of purer pectin. The different monomeric composition and the wide range of molecular weight of the obtained pectins pointed out their usefulness in different potential food applications (e.g., thickening, gelling ingredients) and biological activities. This has been evidenced by the differences found in their physicochemical and techno-functional characteristics. Finally, it can be considered that the berries here studied are efficient sources of pectin.
Asunto(s)
Fraccionamiento Químico , Frutas/química , Pectinas/aislamiento & purificación , Rosales/química , Celulasa/química , Ácido Cítrico/química , Fragaria/química , Peso Molecular , Ribes/química , Rubus/química , UltrasonidoRESUMEN
Pittosporum angustifolium, known as gumbi gumbi, is a native Australian plant, which has traditionally been used as an Aboriginal medicine. This study investigates the effect of different solvents and extractive fermentation on the content and natural products composition of Pittosporum angustifolium extracts, and compares their antioxidant activity, in vitro α-amylase inhibition, and anti-inflammatory properties. Anti-inflammatory activity of the extracts was determined by measuring the inhibition of nitric oxide (NO) production. Extracts were characterised with FTIR-ATR spectroscopy, and screened for antioxidant activities and α-amylase inhibitory activity via High-performance thin-layer chromatography (HPTLC)-Effect-directed analysis (EDA) with direct bioautography. HPTLC combined with chemical derivatization and bioassays was used for EDA screening. The results show that lactic acid fermentation of gumbi gumbi leaves boosts the antioxidant activity in extracts by increasing the total phenolic content, but does not affect (increase or decrease) α-amylase inhibitory activity or nitrogen scavenging/anti-inflammatory activity. Analysis of the ATR-FTIR spectra from the band at RFâ¯=â¯0.85 that inhibits α-amylase, suggests that fatty acid esters are responsible for the enzyme inhibition; both saturated fatty acid esters in unfermented extracts and unsaturated fatty acid esters in fermented extracts. The ATR-FTIR spectra of the polyphenolics in fermented extracts (RFâ¯=â¯0.15-0.20) suggests the presence of soluble lignin fragments (i.e. lignins depolymerized into monomers and oligomers during the fermentation process).
Asunto(s)
Antioxidantes/análisis , Extractos Vegetales/análisis , Rosales/química , Antioxidantes/química , Antioxidantes/farmacología , Bioensayo , Cromatografía Líquida de Alta Presión , Cromatografía en Capa Delgada , Fermentación , Extractos Vegetales/química , Extractos Vegetales/farmacología , alfa-Amilasas/antagonistas & inhibidoresRESUMEN
The chemical and pharmacological profiles of essential oils (EOs) hydrodistilled in yields of 0.03-0.77 % (w/w) from three exotic (Cinnamomum camphora, Petroselinum crispum, and Syzygium samarangense) and two endemic (Pittosporum senacia subsp. senacia and Syzygium coriaceum) medicinal plants were studied. GC-MS/GC-FID analysis of the EOs identified the most dominant components to be myristicin (40.3 %), myrcene (62.2 %), 1,8-cineole (54.0 %), ß-pinene (21.3 %) and (E)-ß-ocimene (24.4 %) in P. crispum, P. senacia and C. camphora, S. samarangense and S. coriaceum EOs, respectively. All EOs were found to possess anti-amylase (0.70-1.50â mM ACAE/g EO) and anti-tyrosinase (109.35-158.23â mg KAE/g) properties, whereas no glucosidase inhibition was displayed. Only Syzygium EOs acted as dual inhibitors of both acetyl- and butyryl-cholinesterases, while P. senacia and C. camphora EOs inhibited acetylcholinesterase selectively and P. crispum EO was inactive (AChE: 4.64-4.96â mg GALAE/g; BChE: 5.96 and 7.10â mg GALAE/g). Molecular docking revealed 1,8-cineole to present the best binding affinities with butyrylcholinesterase, amylase and tyrosinase, while both myristicin and ß-pinene with acetylcholinesterase and finally ß-pinene with glucosidase. In vitro antioxidant potency was also demonstrated in different assays (DPPH: 13.52-53.91â mg TE/g, ABTS: 5.49-75.62â mg TE/g; CUPRAC: 45.38-243.21â mg TE/g, FRAP: 42.49-110.64â mg TE/g; and phosphomolybdenum assay: 82.61-160.93â mM TE/g). Principal component analysis revealed the EOs to differ greatly in their bioactivities due to their chemodiversity. This study has unveiled some interesting preliminary pharmacological profiles of the EOs that could be explored for their potential applications as phytotherapeutics.
Asunto(s)
Antioxidantes/farmacología , Inhibidores Enzimáticos/farmacología , Aceites Volátiles/farmacología , Análisis de Componente Principal , Acetilcolinesterasa/metabolismo , Amilasas/antagonistas & inhibidores , Amilasas/metabolismo , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Benzotiazoles/antagonistas & inhibidores , Compuestos de Bifenilo/antagonistas & inhibidores , Butirilcolinesterasa/metabolismo , Cinnamomum camphora/química , Relación Dosis-Respuesta a Droga , Evaluación Preclínica de Medicamentos , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Cromatografía de Gases y Espectrometría de Masas , Mauricio , Simulación del Acoplamiento Molecular , Estructura Molecular , Monofenol Monooxigenasa/antagonistas & inhibidores , Monofenol Monooxigenasa/metabolismo , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Petroselinum/química , Picratos/antagonistas & inhibidores , Rosales/química , Relación Estructura-Actividad , Ácidos Sulfónicos/antagonistas & inhibidores , Syzygium/químicaRESUMEN
The present study analyzes the complex of bioactive compounds from rose hips pulp powder (RHP) obtained after separating the seeds from Rosa canina L. in order to obtain the oil. The extract prepared from RHP was characterized in terms of the total content of polyphenols, flavonoids, cinnamic acids, flavonols, carotenoids, but also the content of individual polyphenols and carotenoids, antioxidant activity, and CIELab color parameters. The effects of some salts, potentially present in foods, and pH variations were examined to predict possible interactions that could occur when adding rosehip pulp as a food component. The results turned out to be a high content of polyphenols, carotenoids and antioxidant activity. The main phenolic components are procyanidin B1, chlorogenic acid, epicatechin, procyanidin B2, gallic acid, salicylic acid, and catechin. The carotenoid complex includes all-trans-ß-carotene, all-trans-lycopene, zeaxanthin, α-cryptoxanthin, ß-cryptoxanthin, rubixanthin, cis-ß-carotene, cis-γ-carotene and cis-lycopene. The addition of CaCl2 and NaCl to the RHP extract reduced the antioxidant activity and the strong acidic environment (pH to 2.5) decreased the antioxidant activity by 29%. The addition of rose hip powder to gingerbread has improved its general characteristics, and increased its antioxidant activity and microbiological stability, the effects of 4% RHP being the most important.
Asunto(s)
Antioxidantes/farmacología , Bacterias/efectos de los fármacos , Pan/análisis , Carotenoides/farmacología , Flavonoides/farmacología , Extractos Vegetales/farmacología , Polifenoles/farmacología , Rosales/química , Zingiber officinale/química , Antioxidantes/aislamiento & purificación , Carotenoides/aislamiento & purificación , Flavonoides/aislamiento & purificación , Extractos Vegetales/aislamiento & purificación , Polifenoles/aislamiento & purificaciónRESUMEN
Pittosporum senacia (PS) Putt. (Pittosporaceae), indigenous to the Mascarene Islands, is a common ingredient in traditional medicines. However, there is currently a dearth of studies to validate some of these traditional claims. Given the broad traditional uses of PS against several diseases, we aimed to provide a comprehensive insight into the biological and chemical profile of P. senacia. The antioxidant, enzyme inhibitory activity, anticancer, and phytochemical composition of the methanolic extract of P. senacia leaf extracts were studied. The possible interaction and binding mode of the most abundant phytochemicals were studied via in silico docking experiments on tyrosinase and α-glucosidase. The mechanism behind the cytotoxic property of P. senacia extract for MDA-MB-231 was also examined using different methods including 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) cell viability test checking apoptosis-associated genes, and wound healing assays. Twenty-six compounds were identified, of which caffeoylquinic acid derivatives, ferulic acid derivative, cinnamoylquinic acid derivative and two other polyphenols (oleuropeine and isoramnetin glucoside) being abundant, have been tested using in silico studies, against α-glucosidase and tyrosinase. The extract (IC50 = 118.8 µg/ml) exhibited time and dose dependent anti-proliferative effect on human breast cancer cell line, MDA-MB-231. According to the expression profile of apoptosis inhibitors and apoptosis promoters genes, expression of Bax and Bak genes were significantly increased compared to Bcl-2 and Birc5 genes. Based on wound healing analysis, cell migration was inhibited after the application of the plant extract. The present findings suggested that PS might be a good candidate as sources of bioactive compounds for designing functional applications.
Asunto(s)
Antibacterianos/farmacología , Antineoplásicos Fitogénicos/farmacología , Apoptosis/efectos de los fármacos , ADN/efectos de los fármacos , Inhibidores Enzimáticos/farmacología , Simulación del Acoplamiento Molecular , Extractos Vegetales/farmacología , Rosales/química , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Proliferación Celular/efectos de los fármacos , Supervivencia Celular/efectos de los fármacos , Cromatografía Líquida de Alta Presión , Ensayos de Selección de Medicamentos Antitumorales , Inhibidores Enzimáticos/química , Inhibidores Enzimáticos/aislamiento & purificación , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Humanos , Pruebas de Sensibilidad Microbiana , Monofenol Monooxigenasa/antagonistas & inhibidores , Monofenol Monooxigenasa/metabolismo , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Plásmidos/efectos de los fármacos , Espectrometría de Masa por Ionización de Electrospray , Células Tumorales Cultivadas , alfa-Glucosidasas/metabolismoRESUMEN
OBJECTIVE: Pittosporum angustifolium Lodd. is used to treat a variety of pathogenic diseases and inflammation by Australian aborigines. Practitioners of complementary medicine frequently use herbal medicines concurrently with conventional antibiotics. There is a need to evaluate their effects in combination. METHODS: The bacterial growth inhibitory activity of P. angustifolium leaf extracts was assessed against a panel of pathogenic triggers of some autoimmune diseases by standard disc diffusion and liquid dilution minimum inhibitory concentration (MIC) methods. Combinational effects between the extracts and conventional antimicrobials were classified using the sum of the fractional inhibitory concentration. Synergistic interactions were further assessed across a range of ratios by isobologram analysis. The toxicity of the individual samples and combinations was evaluated by Artemia lethality and 3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) human dermal fibroblast cell viability assays. RESULTS: P. angustifolium leaf extracts strongly inhibited the growth of several bacterial triggers of autoimmune diseases. The methanolic, aqueous and ethyl acetate extracts were particularly good inhibitors of Proteus mirabilis and Klebsiella pneumonia growth (MICâ¯=â¯26 and 57⯵g/mL respectively). Some combinations of the extracts and conventional antibiotics significantly potentiated the combined inhibitory activity compared to the individual components. Of the 250 combinations studied, approximately 0.02% showed synergistic interactions, 49.6% were additive, 46.8% showed indifferent interactions and antagonism occurred in only 0.02% of the combinations. Interestingly, all of the synergistic and antagonistic combinations contained tetracycline as their antibiotic component. CONCLUSION: P. angustifolium leaf extracts inhibit the growth of pathogenic triggers of some autoimmune diseases. Some extracts also potentiated the activity of conventional antibiotics, without significantly affecting the toxicity of the combination.
Asunto(s)
Antibacterianos/farmacología , Bacterias/efectos de los fármacos , Interacciones de Hierba-Droga , Extractos Vegetales/farmacología , Rosales/química , Quimioterapia Combinada , Humanos , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/toxicidad , Hojas de la Planta/química , Rosales/toxicidadRESUMEN
Reduced graphene oxide (rGO) is relied upon to be the most promising candidate for high-proficiency. Hydrazine is the most conventional efficient reducing agent that has been frequently used for reduction of graphene oxide, however, it is not environmentally safe due to its toxic nature, causing unsatisfactory defects on the basal plan of GO. Therefore, employing green and efficient reducing agents from natural sources like plant extracts has become the research interest for obtaining high quality reduced graphene oxide sheets in recent years. Here a one-step, easy, cost-effective and green synthesis method based on Nettle leaves' extract has been introduced as an effective reduction method of graphene oxide compared with the toxic and harmful Hydrazine hydrate substance. In this study, GO and rGO were obtained from various methods and characterized by Raman spectroscopy, field emission scanning electron microscope, high-resolution transmission electron microscope (HR-TEM), X-ray diffraction analysis (XRD) and X-ray photon spectroscopy (XPS) analysis. Results of different analytical techniques revealed that the Nettle leaves' extract could successfully reduce GO sheets to high performance reduced graphene oxide with 79% efficiency in comparison with conventional Hydrazine hydrate. On the other side the rGO obtained by Nettle solution could scavenge the free radicals with 70% inhibition capacity at least concentration. Existence of Histamine and Serotonin and many other polyphenols as a part of Nettle leaves composition by following anti-oxidants mechanisms (H donation or electron transfer) promote the anti-oxidant functionality of Nettle leaves. So the highlighted achievement of this paper is to obtain a highly anti-oxidant green reduced graphene oxide with a wide applications i.e medical and polymer composite with UV-shielding activity.
Asunto(s)
Antioxidantes/química , Aminas Biogénicas/química , Depuradores de Radicales Libres/química , Grafito/química , Sustancias Peligrosas/química , Hidrazinas/química , Rosales/química , Sustancias Reductoras/químicaRESUMEN
In order to assist developing a natural, safe food-preservative, aqueous ethanolic extracts of leaves and berries of eight Finnish berry plants were fractionated with Sephadex LH-20 column chromatography. For each fraction, phenolic compounds were analyzed with NMR, UPLC-DAD-ESI-MS and HPLC-DAD. The antioxidant activities of the fractions were investigated using oxygen radical absorbance capacity (ORAC) assay, and the antibacterial activities were evaluated against foodborne pathogens Staphylococcus aureus and Escherichia coli. Antioxidant activities of the fractions correlated highly with both the total concentration and structural feature of phenolic compounds, including both flavonoids and non-flavonoid phenolics. ORAC value correlated strongly with the concentration of (+)-catechin, (-)-epicatecin, quercetin glycosides, and anthocyanins. Increase in size and number of sugar moieties may reduce the antioxidative activities of quercetin glycosides. Type of sugar moieties may have a significant role in influencing peroxyl-radicals scavenging ability of quercetin glycosides with monosaccharides as a single sugar moieties. Most of the fractions inhibited the target microbes. S. aureus strains expressed a higher sensitivity to phenolic compounds than E. coli strains.
Asunto(s)
Fraccionamiento Químico/métodos , Dextranos , Frutas/química , Fenoles/aislamiento & purificación , Extractos Vegetales/química , Hojas de la Planta/química , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Antioxidantes/aislamiento & purificación , Antioxidantes/farmacología , Cromatografía/métodos , Cromatografía Líquida de Alta Presión , Escherichia coli/efectos de los fármacos , Finlandia , Indicadores y Reactivos , Espectroscopía de Resonancia Magnética , Fenoles/farmacología , Rosaceae/química , Rosales/química , Espectrometría de Masa por Ionización de Electrospray , Staphylococcus aureus/efectos de los fármacos , Vaccinium vitis-Idaea/químicaRESUMEN
Endothelial cells have an important role in maintaining vascular homeostasis. Age-related disorders (including obesity, diabetes, and hypertension) or aging per se induce endothelial dysfunction that predisposes to the development of atherosclerosis. Polyphenols have been reported to suppress age-related endothelial cell disorders, but their role in vascular function is yet to be determined. We investigated the influence of boysenberry polyphenol on vascular health under metabolic stress in a murine model of dietary obesity. We found that administration of boysenberry polyphenol suppressed production of reactive oxygen species (ROS) and increased production of nitric oxide (NO) in the aorta. It has been reported that p53 induces cellular senescence and has a crucial role in age-related disorders, including heart failure and diabetes. Administration of boysenberry polyphenol significantly reduced the endothelial p53 level in the aorta and ameliorated endothelial cell dysfunction in iliac arteries under metabolic stress. Boysenberry polyphenol also reduced ROS and p53 levels in cultured human umbilical vein endothelial cells (HUVECs), while increasing NO production. Uncoupled endothelial nitric oxide synthase (eNOS monomer) is known to promote ROS production. We found that boysenberry polyphenol reduced eNOS monomer levels both in vivo and in vitro, along with an increase of eNOS dimerization. To investigate the components of boysenberry polyphenol mediating these favorable biological effects, we extracted the anthocyanin fractions. We found that anthocyanins contributed to suppression of ROS and p53, in association with increased NO production and eNOS dimerization. In an ex vivo study, anthocyanins promoted relaxation of iliac arteries from mice with dietary obesity. These findings indicate that boysenberry polyphenol and anthocyanins, a major component of this polyphenol, inhibit endothelial dysfunction and contribute to maintenance of vascular homeostasis.
Asunto(s)
Vasos Sanguíneos/efectos de los fármacos , Vasos Sanguíneos/fisiopatología , Endotelio Vascular/efectos de los fármacos , Endotelio Vascular/metabolismo , Polifenoles/farmacología , Rosales/química , Animales , Antocianinas/farmacología , Células Endoteliales/efectos de los fármacos , Células Endoteliales/metabolismo , Endotelio Vascular/fisiopatología , Células Endoteliales de la Vena Umbilical Humana , Humanos , Ratones , Óxido Nítrico/metabolismo , Óxido Nítrico Sintasa de Tipo III/metabolismo , Polifenoles/química , Especies Reactivas de Oxígeno/metabolismo , Estrés Fisiológico/efectos de los fármacosRESUMEN
BACKGROUND: Influenza infection remains a major health threat for animals and humans which crucially requires effective antiviral remedies. The usage of herbal medications as readily available alternatives for their compatibility with the body and fewer side effects compared to synthetic chemical treatments has become popular globally. The aim of this study was to investigate and screen in vitro anti-influenza activity of extracts of five South African medicinal plants, namely Tabernaemontana ventricosa, Cussonia spicata, Rapanea melanophloeos, Pittosporum viridiflorum and Clerodendrum glabrum, species which are used traditionally for the treatment of several diseases such as inflammatory and respiratory diseases. METHODS: Methanol, ethanol (100% and 30%), acetone, hot and cold water extracts of the powdered plants leaves were obtained by standard methods. The cytotoxicity was determined by the MTT colorimetric assay on MDCK cells. The concentrations below CC50 values were tested for antiviral activity against influenza A virus (IAV) in different combination treatments. The effect of extracts on viral surface glycoproteins and viral titer were tested by HI and HA virological assays, respectively. RESULTS: Based on the applied methods, the most effective results against IAV were obtained from Rapanea melanophloeos methanol leaf extract (EC50 = 113.3 µg/ml) and Pittosporum viridiflorum methanol, 100% and 30% ethanol and acetone leaf extracts (EC50 values = 3.6, 3.4, 19.2, 82.3 µg/ml, respectively) in all types of combined treatments especially in pre- and post-penetration combined treatments with highly significant effects against viral titer (P ≤ 0.01). CONCLUSION: The outcomes offer for the first time a scientific basis for the use of extracts of Rapanea melanophloeos and Pittosporum viridiflorum against IAV. It is worth focusing on the isolation and identification of effective active compounds and elucidating the mechanism of action from these species. However, Tabernaemontana ventricosa, Cussonia spicata and Clerodendrum glabrum leaf extracts were ineffective in vitro in this study.
Asunto(s)
Antivirales/farmacología , Virus de la Influenza A/efectos de los fármacos , Extractos Vegetales/farmacología , Plantas Medicinales/química , Animales , Antivirales/química , Antivirales/toxicidad , Supervivencia Celular/efectos de los fármacos , Perros , Pruebas de Inhibición de Hemaglutinación , Células de Riñón Canino Madin Darby , Extractos Vegetales/química , Extractos Vegetales/toxicidad , Primulaceae/química , Rosales/química , SudáfricaRESUMEN
BACKGROUND: Previous study showed that aqueous (AEPM) and methanol (MEPM) extracts from the leaves of Pittosporum mannii have analgesic effects in acute pain models. The present study evaluates the acute and chronic anti-hypernociceptive and anti-inflammatory effects of AEPM and MEPM in a model of persistent inflammatory pain. METHODS: The third day after induction of inflammatory pain by subplantar injection of 100 µL of CFA in Wistar rats, AEPM and MEPM were administered orally (75, 150 and 300 mg/kg/day) and their anti-hyperalgesic and anti-inflammatory effects were follow in acute (1-24 h) and chronic (for 14 days) treatments. At the end of the chronic treatment, oxidative stress and liver parameters were assessed. Effects of plant extracts were also evaluated on nociception induced by Phorbol 12-Myristate 13-Acetate (PMA) and 8-bromo 3',5'-cAMP (8-Br-cAMP) in mice. RESULTS: AEPM and MEPM significantly reversed the mechanical hyperalgesia caused by CFA in acute and chronic treatment. Moreover, AEPM and MEPM also significantly reduced the nociception caused by PMA (60%) and 8-Br-cAMP (87%). Nevertheless, AEPM and MEPM failed to inhibit the paw edema caused by CFA. Plant extracts significantly reduced the nitric oxide content in the spinal cord and the plasmatic concentration of alanine aminotransferase. MEPM also significantly increased the glutathione content in the spinal cord. CONCLUSION: AEPM and MEPM given orally are effective in inhibiting mechanical hyperalgesia in persistent inflammatory pain caused by CFA. Their mechanisms of action seem to involve an interaction with PKC, PKA and nitric oxide pathways. These extracts might be devoid of hepatotoxic effects.
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Hiperalgesia/tratamiento farmacológico , Dolor/tratamiento farmacológico , Extractos Vegetales/farmacología , Hojas de la Planta/química , Rosales/química , Analgésicos/farmacología , Animales , Antiinflamatorios/farmacología , Edema/inducido químicamente , Edema/tratamiento farmacológico , Femenino , Adyuvante de Freund/farmacología , Glutatión/metabolismo , Hiperalgesia/metabolismo , Inflamación/inducido químicamente , Inflamación/complicaciones , Inflamación/metabolismo , Masculino , Metanol/química , Ratones , Dolor/etiología , Dimensión del Dolor/métodos , Fitoterapia/métodos , Ratas , Ratas Wistar , Médula Espinal/metabolismoRESUMEN
BACKGROUND: Plant essential oils and phenolic compounds are widely used for their medicinal properties. Thus, the aim of this study is to evaluate the nutritional values, the chemical composition, antioxidant activity and anti-hemolytic effects of Pittosporum tobira seeds. METHODS: The aroma compounds were isolated using two methods (Headspace-solid phase microextraction (HS-SPME) and hydrodistillation (HD)) and analyzed by gas chromatography coupled with mass spectrometry (GC-MS). Bioactive phenolic compounds were identified by mean of high-performance liquid chromatography (HPLC-DAD). Reducing power, hydrogen peroxide (H2O2) scavenging and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assays were used to investigate antioxidant activity. Anti-hemolytic activity was evaluated using H2O2-induced hemolysis of red blood cells (RBC). RESULTS: Oxygenated sesquiterpenes, sesquiterpene hydrocarbons and oxygenated monoterpenes were the most volatile fractions identified by HD and HS-SPME coupled to GC-MS but their quality and amount were quite different according to the extraction methodology. The main phenolic compounds identified by HPLC were caffeic acid, followed by cinnamic acid and gallic acid. P. tobira seeds essential oils showed significant antioxidant activity in DPPH (IC50 value = 1.5 mg/mL), H2O2 scavenging assay (IC50 value = 159.43 µg/mL) and reducing power test (IC50 value = 0.982 mg/mL) compared to methanolic extract. Moreover, the results revealed that the essential oil was able to protect RBC from hemolysis induced by H2O2. However, the methanolic extract had no effect on H2O2-induced hemolysis of RBC as compared to the essential oil and the standard vitamin C. CONCLUSIONS: P. tobira may be used as a new natural source of antioxidant with therapeutic application in diseases caused by reactive oxygen species. Phytochemical Characterization and Biological Evaluation of Pittosporum tobira seeds.
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Antioxidantes/aislamiento & purificación , Fenoles/aislamiento & purificación , Fitoquímicos/aislamiento & purificación , Rosales/química , Semillas/química , Antioxidantes/farmacología , Compuestos de Bifenilo/antagonistas & inhibidores , Compuestos de Bifenilo/química , Ácidos Cafeicos/aislamiento & purificación , Ácidos Cafeicos/farmacología , Cromatografía Líquida de Alta Presión , Cinamatos/aislamiento & purificación , Cinamatos/farmacología , Eritrocitos/efectos de los fármacos , Ácido Gálico/aislamiento & purificación , Ácido Gálico/farmacología , Cromatografía de Gases y Espectrometría de Masas , Hemólisis/efectos de los fármacos , Peróxido de Hidrógeno/antagonistas & inhibidores , Peróxido de Hidrógeno/química , Monoterpenos/aislamiento & purificación , Monoterpenos/farmacología , Odorantes/análisis , Aceites Volátiles/aislamiento & purificación , Aceites Volátiles/farmacología , Fenoles/farmacología , Fitoquímicos/farmacología , Picratos/antagonistas & inhibidores , Picratos/química , Extractos Vegetales/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Microextracción en Fase SólidaRESUMEN
The phytochemical study of two cultivars of Pittosporum tenuifolium Banks & Sol. ex Gaertn, "variegatum" and "gold star", led to the isolation of eight oleanane-type glycosides: seven previously undescribed and a known one. Their aglycons are oxygenated oleanane derivatives as barringtogenol C, camelliagenin A, hederagenin, and 22α-hydroxyoleanolic acid. Their structures were established by 2D NMR spectroscopic techniques and mass spectrometry as 3-O-ß-D-galactopyranosyl-(1 â 2)-[α-L-arabinopyranosyl-(1 â 3)]-ß-D-glucuronopyranosyl-21-O-angeloyl-22-O-acetylbarringtogenol C, 3-O-ß-D-galactopyranosyl-(1 â 2)-[α-L-arabinopyranosyl-(1 â 3)]-ß-D-glucuronopyranosyl-21,22-di-O-angeloylbarringtogenol C, 3-O-ß-D-galactopyranosyl-(1 â 2)-[α-L-arabinopyranosyl-(1 â 3)]-ß-D-glucuronopyranosyl-22-O-angeloylcamelliagenin A, 3-O-ß-D-glucopyranosyl-(1 â 2)-[ß-D-glucopyranosyl-(1 â 6)]-ß-D-glucopyranosyl-22-O-[(6-O-acetyl)-ß-D-glucopyranosyl]camelliagenin A, 3-O-ß-D-galactopyranosyl-(1 â 2)-[α-L-arabinofuranosyl-(1 â 4)]-ß-D-glucuronopyranosylhederagenin 28-O-ß-D-glucopyranosyl ester, 3-O-α-L-arabinofuranosyl-(1 â 4)-ß-D-glucuronopyranosylhederagenin 28-O-ß-D-glucopyranosyl ester, 3-O-ß-D-galactopyranosyl-(1 â 2)-[α-L-arabinofuranosyl-(1 â 4)]-ß-D-glucuronopyranosyl-22α-hydroxyoleanolic acid 28-O-ß-D-glucopyranosyl ester, and the known ilexoside XLIX. These results represent a significative contribution to the chemotaxonomy of the genus Pittosporum, highlighting hederagenin-type saponins as chemotaxonomic markers of P. tenuifolium cultivars.
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Glicósidos/química , Ácido Oleanólico/análogos & derivados , Rosales/química , Glicósidos/aislamiento & purificación , Estructura Molecular , Ácido Oleanólico/química , Ácido Oleanólico/aislamiento & purificación , Extractos Vegetales/química , Saponinas/química , Saponinas/aislamiento & purificaciónRESUMEN
ETHNOPHARMACOLOGICAL RELEVANCE: Pittosporum viridiflorum Sims, a Pittosporaceae species, is used extensively in African traditional medicine (ATM) by various tribes. This review is an appraisal of the information concerning the description, distribution, conservation status, traditional uses, phytochemistry, pharmacology and toxicology of this species with the aim of reconciling it with its traditional use. MATERIALS AND METHODS: A wide-ranging literature search was conducted using database platforms such as Scopus, Google Scholar, Web of Science, ScienceDirect, PubMed and books including local reports and thesis submissions. RESULTS: Ten categories to which P. viridiflorum finds use in traditional medicine (TM) were found, and they include well-being, wounds, treatment of veterinary ailments, gastrointestinal and sexually transmitted diseases, kidney, circulatory and inflammatory disorders, as well as diseases such as cancer, tuberculosis, and malaria. Pharmacological tests conducted include those investigating antimicrobial, antidiarrhoeal, antimalarial, anticancer, anti-inflammatory, antioxidant and acaricidal properties. Promising activity was shown in a number of assays. Toxicological effects have also been reported from this species. However, it is recommended to conduct a detailed toxicological study, including genotoxicity, as this has not yet been evaluated. Compound(s) with antimalarial, anticancer and acaricidal properties have been isolated from P. viridiflorum. CONCLUSIONS: The collective pharmacological and phytochemical properties of P. viridiflorum gives credence to the use of this plant species against various diseases in ATM, thus steering significant interest towards in vivo studies and further research.
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Medicinas Tradicionales Africanas , Plantas Medicinales , Rosales/química , África , Conservación de los Recursos Naturales , Humanos , FitoterapiaRESUMEN
A simple, accurate and reproducible reversed-phase liquid chromatographic method was developed for qualitative and quantitative determination of four bioactive flavonoids (ampelopsin, taxifolin, myricetin and quercetin) from the fruit-stalk extract of Hovenia dulcis Thunb. Chromatographic separation was performed on a C18 column (4.6 × 150 mm, 3.5 µm) with mobile phase consisting of 0.1% acetic acid and 100% acetonitrile at a flow rate of 1.0 mL/min. The analysis was performed using a diode array detector at 365 nm. The method was validated in terms of selectivity, linearity, accuracy, precision and recovery. Good linearity was observed over the investigated concentration range (10-500 µg/mL), with correlation coefficient values greater than 0.99. The intra- and inter-day precisions over the concentration range were <3.91% (relative standard deviation), and the accuracy was between 91.57 and 106.66%. The mean recovery for all the analytes was 100.87%. This method was successfully applied in the quality assessment of bioactive flavonoids in the fruit-stalk extract of H. dulcis.
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Cromatografía Líquida de Alta Presión/métodos , Flavonoides/análisis , Extractos Vegetales/análisis , Rosales/química , Frutas/químicaRESUMEN
Two new triterpenoid estersaponins (1, 2) were isolated from the leaves of Pittosporum tobira 'Variegata' (Thunb.) W. T. Aiton, along with one known saponin (3) and one known flavonoid glycoside (4). Their structures were established by different spectroscopic methods including 1D and 2D NMR, UV, as well as ESI-MS analysis. The investigated 80% aqueous methanol extract showed significant dose dependent inhibition of acetic acid induced abdominal writhing in mice. The n-butanol fraction exerted moderate antimicrobial activity against Staphylococcus aureus and Escherichia coli. In addition, it showed in vitro antioxidant activity with IC50 value (7.3 µg/ml) lower than that of the positive control ascorbic acid (11.2 µg/ml), using DPPH free radical scavenging activity method. Evaluation of its in vitro cytotoxicity showed strong activity against breast carcinoma (MCF-7), hepatocellular carcinoma (HepG2), and colon carcinoma (HCT) cell lines.
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Flavonoides/farmacología , Extractos Vegetales/farmacología , Rosales/química , Saponinas/farmacología , Triterpenos/farmacología , Analgésicos/aislamiento & purificación , Analgésicos/farmacología , Animales , Antibacterianos/aislamiento & purificación , Antibacterianos/farmacología , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Línea Celular Tumoral , Escherichia coli/efectos de los fármacos , Flavonoides/aislamiento & purificación , Depuradores de Radicales Libres/aislamiento & purificación , Depuradores de Radicales Libres/farmacología , Humanos , Masculino , Ratones , Estructura Molecular , Hojas de la Planta/química , Saponinas/aislamiento & purificación , Staphylococcus aureus/efectos de los fármacos , Triterpenos/aislamiento & purificaciónRESUMEN
ETHNOPHARMACOLOGICAL RELEVANCE: Pittosporum mannii Hook. f. (Pittosporaceae) is a plant widely used in traditional medicine in Cameroon for the treatment of many gastrointestinal disorders including diarrhea. To date, no pharmacological study on the antidiarrheal and the antispasmodic properties of this plant has been reported. The aim of the present study was to evaluate in vitro the relaxant activity of the aqueous extract of stem barks of P. mannii (PMAE) on rat duodenum. MATERIALS AND METHODS: Different concentrations of PMAE were tested separately (10-80 µg/mL) or cumulatively (5-80 µg/mL) on spontaneous and spasmogen (carbachol, histamine and KCl)-induced contractions of isolated rat duodenum strips. RESULTS: At concentrations ranging from 10 to 80 µg/mL, PMAE significantly decreased the tonus and the amplitude of spontaneous contractions. However, at high concentration (80 µg/mL), the extract elicited a transient relaxation was followed by a slight increase of tonus, while the amplitude remained lower compared to the normal spontaneous activity. The relaxant effect of the extract was not significantly affected in the presence of atropine (0.713 µg/mL) and promethazine (0.5 µg/mL). In addition, PMAE (20, 40, and 80 µg/mL) partially but significantly inhibited in a concentration related manner the contractions induced by carbachol (10(-9)-10(-4)M) and histamine (10(-9)-10(-4)M) on rat duodenum. PMAE (10-80 µg/mL) also significantly induced a concentration-dependent relaxation on KCl (20mM, 50mM, 10(-3)-6.10(-3)M)-induced contraction of rat duodenum. CONCLUSIONS: These results show that the aqueous extract of P. mannii stem barks possesses antispasmodic and spasmolytic effects at lower concentrations; therefore, supporting the use of the stem barks of this plant in the folk medicine for the treatment of diarrhea. However, caution should be paid while using higher concentrations that instead might produce spasmogenic effect and might worsen the diarrheal condition. The relaxant effect of PMAE appears to be non-specific of muscarinic or histaminic receptors, but may involve at least in part a mechanism of inhibition of the Ca(2+) influx into the smooth muscle cells through voltage-operated Ca(2+) channels.