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1.
Molecules ; 26(3)2021 Jan 28.
Artigo em Inglês | MEDLINE | ID: mdl-33525719

RESUMO

Pyrrolizidine alkaloids (PAs) are genotoxic carcinogenic phytotoxins mostly prevalent in the Boraginaceae, Asteraceae and Fabaceae families. Heliotropium species (Boraginaceae) are PA-producing weeds, widely distributed in the Mediterranean region, that have been implicated with lethal intoxications in livestock and humans. In Israel, H. europaeum, H. rotundifolium and H. suaveolens are the most prevalent species. The toxicity of PA-producing plants depends on the PA concentration and composition. PAs occur in plants as mixtures of dozens of various PA congeners. Hence, the risk arising from simultaneous exposure to different congeners has to be evaluated. The comparative risk evaluation of the three Heliotropium species was based on recently proposed interim relative potency (iREP) factors, which take into account certain structural features as well as in vitro and in vivo toxicity data obtained for several PAs of different classes. The aim of the present study was to determine the PA profile of the major organ parts of H. europaeum, H. rotundifolium and H. suaveolens in order to assess the plants' relative toxic potential by utilizing the iREP concept. In total, 31 different PAs were found, among which 20 PAs were described for the first time for H. rotundifolium and H. suaveolens. The most prominent PAs were heliotrine-N-oxide, europine-N-oxide and lasiocarpine-N-oxide. Europine-N-oxide displayed significant differences among the three species. The PA levels ranged between 0.5 and 5% of the dry weight. The flowers of the three species were rich in PAs, while the PA content in the root and flowers of H. europaeum was higher than that of the other species. H. europaeum was found to pose a higher risk to mammals than H. rotundifolium, whereas no differences were found between H. europaeum and H. suaveolens as well as H. suaveolens and H. rotundifolium.


Assuntos
Heliotropium/efeitos adversos , Flores/efeitos adversos , Flores/química , Heliotropium/química , Israel , Alcaloides de Pirrolizidina/efeitos adversos , Alcaloides de Pirrolizidina/química , Medição de Risco
2.
Biomolecules ; 11(1)2021 01 04.
Artigo em Inglês | MEDLINE | ID: mdl-33406643

RESUMO

Heliotropium is one of the most important plant genera to have conventional folklore importance, and hence is a potential source of bioactive compounds. Thus, the present study was designed to explore the therapeutic potential of Heliotropium crispum Desf., a relatively under-explored medicinal plant species. Methanolic extracts prepared from a whole plant of H. crispum were studied for phytochemical composition and possible in vitro and in silico biological properties. Antioxidant potential was assessed via six different assays, and enzyme inhibition potential against key clinical enzymes involved in neurodegenerative diseases (acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)), diabetes (α-amylase and α-glucosidase), and skin problems (tyrosinase) was assayed. Phytochemical composition was established via determination of the total bioactive contents and reverse phase ultra-high performance liquid chromatography mass spectrometry (RP-UHPLC-MS) analysis. Chemical profiling revealed the tentative presence of 50 secondary metabolites. The plant extract exhibited significant inhibition against AChE and BChE enzymes, with values of 3.80 and 3.44 mg GALAE/g extract, respectively. Further, the extract displayed considerable free radical scavenging activity against DPPH and ABTS radicals, with potential values of 43.19 and 41.80 mg TE/g extract, respectively. In addition, the selected compounds were then docked against the tested enzymes, which have shown high inhibition affinity. To conclude, H. crispum was found to harbor bioactive compounds and showed potent biological activities which could be further explored for potential uses in nutraceutical and pharmaceutical industries, particularly as a neuroprotective agent.


Assuntos
Cromatografia de Fase Reversa , Heliotropium/química , Espectrometria de Massas , Simulação de Acoplamento Molecular , Fármacos Neuroprotetores/química , Fármacos Neuroprotetores/uso terapêutico , Compostos Fitoquímicos/química , Compostos Fitoquímicos/uso terapêutico , Antioxidantes/farmacologia , Cromatografia Líquida de Alta Pressão , Inibidores Enzimáticos/farmacologia , Metabolismo Secundário/efeitos dos fármacos , Termodinâmica
3.
J Food Biochem ; 44(11): e13444, 2020 11.
Artigo em Inglês | MEDLINE | ID: mdl-32815182

RESUMO

Heliotropium indicum Linn is a leafy vegetable that has been used in Bangladeshi ethnomedicinal practices. The attenuation effect of H. indicum supplementation was evaluated in high carbohydrate high-fat (HCHF) diet-induced obesity and associated disorders in 8-weeks-old female Wister rats. H. indicum significantly (p < .05) prevented weight gain and improved glucose intolerance in obese rats. It also significantly (p < .05) ameliorated lipid parameters in HCHF diet fed rats preventing hypercholesterolemia and hypertriglyceridemia, resulting in improved the artherogenic index (AI). Serum alanine aminotransferase (ALT), aspartate aminotransferase (AST), and alkaline phosphatase (ALP) activities were brought to normal by H. indicum. It significantly elevated superoxide dismutase (SOD) and catalase (CAT) activities as well as increased reduced glutathione (GSH) concentration in liver. The intense liver fat deposition was seen in HCHF fed rats which were relatively low in H. indicum fed rats. Therefore, H. indicum has the ability to prevent obesity and associated metabolic disorders. PRACTICAL APPLICATIONS: Obesity and associated metabolic disorders are the most common threats to public health. Modern lifestyle and food habits are the main causes behind this malice, and the introduction of functional foods in daily diet is proved to be highly beneficial. Results of this study demonstrated that H. indicum can effectively attenuate obesity and its associated metabolic complications. Therefore, the current study has the merits to promote scientific knowledge of the dietary application of H. indicum as a functional food among the community.


Assuntos
Dieta Hiperlipídica , Heliotropium , Obesidade , Animais , Carboidratos , Dieta Hiperlipídica/efeitos adversos , Suplementos Nutricionais , Feminino , Obesidade/tratamento farmacológico , Obesidade/prevenção & controle , Estresse Oxidativo , Ratos , Ratos Wistar
4.
F1000Res ; 9: 493, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32676186

RESUMO

Background: Medicinal plants are a source of phytochemicals and they are used for the treatment of several oxidative stress-related or other diseases for their effectiveness, low toxicity and easy availability. Five traditionally used and less characterized herbaceous weeds of West Bengal, India, namely, Heliotropium indicum, Tridax procumbens, Cleome rutidosperma, Commelina benghalensis and Euphorbia hirta, were investigated for the current research study. Methods: Aqueous and 70% ethanolic extracts of the leaves were analyzed for estimation of essential phytochemicals and to evaluate their in vitro antioxidant status, medicinal properties and cytotoxic effects. To the best of our knowledge, several assays and comparative evaluations using these herbs are reported for the first time. For quantitative study, UV-vis spectrophotometry and high-performance liquid chromatography with diode array detector HPLC-DAD techniques were used. Antibacterial properties were investigated using the Kirby-Bauer disc diffusion method. For in vitro anti-lithiatic study, a titration method was used. The cell viability assay was done using peripheral blood mononuclear cells. Results: The aqueous extract exhibits higher content of polyphenols, flavonoids, tannins and inhibition percentage values for free radical scavenging assays, whereas the 70% ethanolic extract exhibits higher content of alkaloids and cardiac glycosides. HPLC-DAD analysis of 70% ethanolic extracts led us to identify 10 predominant phenolic constituents. Euphorbia hirta extracts showed minimum cytotoxicity (cell death ~2.5% and 4 % in water and 70% ethanolic extract, respectively ), whereas Cleome rutidosperma and Tridax procumbens' 70% ethanolic extracts showed higher cell death (~13% and 28%, respectively), compared with the control (cell death ~10-12%). Conclusions: The study concluded that of all the medicinal weeds selected for the current study, Euphorbia hirta possesses the highest amount of bioactive compounds and hence exhibits the highest in vitro antioxidant activity and promising in vitro medicinal properties.


Assuntos
Antioxidantes/farmacologia , Extratos Vegetais/farmacologia , Plantas Daninhas/química , Asteraceae/química , Células Cultivadas , Cleome/química , Commelina/química , Euphorbia/química , Heliotropium/química , Humanos , Índia , Leucócitos Mononucleares/efeitos dos fármacos , Compostos Fitoquímicos/farmacologia
5.
Molecules ; 25(14)2020 Jul 08.
Artigo em Inglês | MEDLINE | ID: mdl-32650373

RESUMO

Heliotropium taltalense is an endemic species of the northern coast of Chile and is used as folk medicine. The polyphenolic composition of the methanolic and aqueous extract of the endemic Chilean species was investigated using Ultrahigh-Performance Liquid Chromatography, Heated Electrospray Ionization and Mass Spectrometry (UHPLC-Orbitrap-HESI-MS). Fifty-three compounds were detected, mainly derivatives of benzoic acid, flavonoids, and some phenolic acids. Furthermore, five major compounds were isolated by column chromatography from the extract, including four flavonoids and one geranyl benzoic acid derivative, which showed vascular relaxation and were in part responsible for the activity of the extracts. Since aqueous extract of H. taltalense (83% ± 9%, 100 µg/mL) produced vascular relaxation through an endothelium-dependent mechanism in rat aorta, and the compounds rhamnocitrin (89% ± 7%; 10-4 M) and sakuranetin (80% ± 6%; 10-4 M) also caused vascular relaxation similar to the extracts of H. taltalense, these pure compounds are, to some extent, responsible for the vascular relaxation.


Assuntos
Aorta/metabolismo , Extratos Vegetais/química , Polifenóis , Vasodilatação/efeitos dos fármacos , Animais , Heliotropium/química , Masculino , Polifenóis/química , Polifenóis/farmacologia , Ratos , Ratos Sprague-Dawley
6.
Mediators Inflamm ; 2020: 5056897, 2020.
Artigo em Inglês | MEDLINE | ID: mdl-32076387

RESUMO

In this study, anti-inflammatory, anticancer, brine shrimp lethality, and FTIR studies were evaluated. The oxidative burst assay using the chemiluminescence technique, MTT assay, brine shrimp lethality assay, and FTIR analysis were the methods used for the evaluation of anti-inflammatory, anticancer, brine shrimp lethality, and FTIR studies, respectively. The whole-plant butanol fraction of Heliotropium europaeum (WBFHE) showed anti-inflammatory activity on ROS having IC5014.7 ± 2.5 while the extract and other fractions of the whole plant of Heliotropium europaeum exhibited no anti-inflammatory activity. None of the extract and fractions of the whole plant of Heliotropium europaeum exhibited anticancer (MCF-7, 3T3, and HeLa cell lines) activities. The whole-plant aqueous fraction of Heliotropium europaeum (WAFHE) and whole-plant butanol fraction of Heliotropium europaeum (WBFHE) showed lethality at high concentration while at low concentration, no toxicity was shown. The whole-plant methanolic extract of Heliotropium europaeum (WMEHE) and whole-plant n-hexane fraction of Heliotropium europaeum (WHFHE) exhibited no toxicity. FTIR interpretation showed the functional groups for the aromatic compounds, phenols, carboxylic acids, esters, alkanes, alkenes, alcohols, alkyl halides, sulfate esters, phosphines, silanes, nitriles, thiols, amines, phosphoric acids, and nitro compounds.


Assuntos
Anti-Inflamatórios/química , Antineoplásicos/química , Artemia/efeitos dos fármacos , Heliotropium/química , Extratos Vegetais/química , Células 3T3 , Animais , Anti-Inflamatórios/farmacologia , Antineoplásicos/farmacologia , Células HeLa , Humanos , Células MCF-7 , Camundongos , Extratos Vegetais/farmacologia , Espectroscopia de Infravermelho com Transformada de Fourier
7.
J Agric Food Chem ; 67(28): 7995-8006, 2019 Jul 17.
Artigo em Inglês | MEDLINE | ID: mdl-31145604

RESUMO

Blue heliotrope (Heliotropium amplexicaule) is an invasive environmental weed that is widely naturalized in eastern Australia and has been implicated as a source of pyrrolizidine alkaloid (PA) poisoning in livestock. Less well-documented is the potential of such carcinogenic alkaloids to contaminate honey from bees foraging on this plant species. In this study, the PA profile of H. amplexicaule plant material, determined by HRAM LC-MS/MS, revealed the presence of nine PAs and PA-N-oxides, including several PAs and PA-N-oxides of the indicine class, which have not previously been reported. The predominant alkaloid, indicine, represents 84% of the reduced PA content, with minor alkaloids identified as intermedine and the newly reported helioamplexine, constituting 7 and 9%, respectively. NMR analysis confirmed the identity of helioamplexine as a previously unreported indicine homologue. This is the first report of the isolation of intermedine, helioamplexine, and 3'-O-angelylindicine from H. amplexicaule. Also described is the identification of N-chloromethyl analogues of the major alkaloids as isolation-derived artifacts from reactions with dichloromethane. Analysis of regional-market honey samples revealed a number of honey samples with PA profiles analogous to that seen in H. amplexicaule, with measured PA contents of up to 2.0 µg of PAs per gram of honey. These results confirm the need for honey producers to be aware of H. amplexicaule as a potential PA source, most particularly in products where honey is sourced from a single location.


Assuntos
Heliotropium/química , Mel/análise , Alcaloides de Pirrolizidina/análise , Animais , Austrália , Abelhas/fisiologia , Cromatografia Líquida , Flores/química , Contaminação de Alimentos/análise , Espectrometria de Massas em Tandem
8.
Curr Org Synth ; 16(4): 498-522, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31984928

RESUMO

BACKGROUND: The inherent glycosidase inhibitory activity and potentially therapeutic value of the polyhydroxylated pyrrolizidine alkaloids containing a hydroxymethyl substituent at the C-3 position have been well documented. Belonging to this class, the naturally occurring hyacinthacine C-type alkaloids are of general interest among iminosugar researchers. Their selective micromolar α -glycosidase inhibitory ranges (10 - 100 µM) suggest that these azasugars are potential leads for treating type II diabetes. However, the structures of hyacinthacine C1, C3 and C4 are insecure with hyacinthacine C5 being recently corrected. OBJECTIVE: This review presents the hyacinthacine C-type alkaloids: their first discovery to the most recent advancements on the structures, biological activities and total synthesis. CONCLUSION: The hyacinthacine C-type alkaloids are of exponentially increasing interest and will undoubtedly continue to be reported as synthetic targets. They represent a challenging but rewarding synthetic feat for the community of those interested in accessing biologically active iminosugars. Since 2009, ten total syntheses have been employed towards accessing similarly related products but only three have assessed the glycosidase inhibitory activity of the final products. This suggests the need for an accessible and universal glycosidase inhibitory assay so to accurately determine the structure-activity relationship of how the hyacinthacine C-type alkaloids inhibit specific glycosidases. Confirming the correct structures of the hyacinthacine C-type alkaloids as well as accessing various analogues continues to strengthen the foundation towards a marketable treatment for type II diabetes and other glycosidase related illnesses.


Assuntos
Inibidores de Glicosídeo Hidrolases/síntese química , Inibidores de Glicosídeo Hidrolases/isolamento & purificação , Glicosídeo Hidrolases/antagonistas & inibidores , Alcaloides de Pirrolizidina/síntese química , Alcaloides de Pirrolizidina/isolamento & purificação , Castanospermum/química , Inibidores de Glicosídeo Hidrolases/história , Inibidores de Glicosídeo Hidrolases/farmacologia , Heliotropium/química , História do Século XX , História do Século XXI , Estrutura Molecular , Alcaloides de Pirrolizidina/história , Alcaloides de Pirrolizidina/farmacologia
9.
Nat Prod Res ; 33(12): 1813-1818, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-29430949

RESUMO

Heliotropium bacciferum (Boraginaceae) is a perennial herb, growing in the Bechar region of Algeria, where it is traditionally used for skin diseases and tonsillitis. Herein, we report the isolation and characterization of sixteen secondary metabolites from the aerial part extracts. They include a sterol (1), megastigman type nor-isoprenoids (2, 3, 4, 6, 8, 10), C-11 terpene lactones (5 and 9), and a monoterpene (7) from the chloroform extract (HB-C); monoterpene glucoside (14), and phenolic compounds (11-13, 15, 16) from the methanol one (HB-M). Their structures were elucidated by spectroscopic methods including 1D and 2D NMR experiments, and ESIMS analysis. HB-M showed a significant and concentration dependent scavenging activity in vitro against the radicals DPPH and ABTS, related to the phenol derivatives (11-13, and 15-16), and HB-C inhibited the growth of colon cancer cell lines, mainly for the presence of the antiproliferative C-11 terpene lactones (5 and 9).


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Heliotropium/química , Argélia , Antineoplásicos Fitogênicos/química , Antioxidantes/química , Linhagem Celular Tumoral , Neoplasias do Colo/tratamento farmacológico , Neoplasias do Colo/patologia , Avaliação Pré-Clínica de Medicamentos , Ensaios de Seleção de Medicamentos Antitumorais , Sequestradores de Radicais Livres/química , Sequestradores de Radicais Livres/farmacologia , Células HCT116 , Heliotropium/metabolismo , Humanos , Estrutura Molecular , Fenóis/análise , Fenóis/química , Extratos Vegetais/química , Plantas Medicinais/química , Plantas Medicinais/metabolismo , Metabolismo Secundário , Espectrometria de Massas por Ionização por Electrospray
10.
Bol. latinoam. Caribe plantas med. aromát ; 17(6): 575-582, nov. 2018. ilus
Artigo em Inglês | LILACS | ID: biblio-1007341

RESUMO

The skin is the largest organ of the human body and its main function is to protect it from the external environment. It is exposed to injuries that require a rapid healing process to recover its functionality. Microorganisms inhabit the skin, which makes up the normal microbial flora, but in situations of injury they can cause infections that slow down the regeneration process. Therefore, there is a great interest in the development of alternative methods to accelerate the regeneration process and prevent infections. In this work, the efficacy of flavonoid 3-O-methylgalangine and the terpenic derivative Filifolinone and its mixtures, isolated from plants of the genus Heliotropium, on the stimulation of cell proliferation was evaluated. The results showed that the mixtures stimulated proliferation and migration in MA104 cells mainly due to the presence of Filifolinone, that together with the known antibacterial activity of 3-O-methylgalangine, opens new alternatives for the use of natural compounds in healing processes.


La piel es el órgano más grande del cuerpo humano y su función principal es protegerla del entorno externo. Está expuesta a lesiones que requieren un proceso de curación rápido para recuperar su funcionalidad. Los microorganismos que habitan en la piel, constituyen la flora microbiana normal, pero en situaciones de lesión pueden causar infecciones que retardan el proceso de regeneración. Por lo tanto, existe un gran interés en el desarrollo de métodos alternativos para acelerar el proceso de regeneración y prevenir infecciones. En este trabajo, se evaluó la eficacia del flavonoide 3-O-metilgalangina y el derivado terpénico Filifolinona y sus mezclas, aisladas de plantas del género Heliotropium, en la estimulación de la proliferación celular. Los resultados mostraron que las mezclas estimularon la proliferación y la migración en las células MA104 debido principalmente a la presencia de Filifolinona, que junto con la actividad antibacteriana conocida de la 3-O-metilgalangina, abre nuevas alternativas para el uso de compuestos naturales en los procesos de curación.


Assuntos
Terpenos/farmacologia , Flavonoides/farmacologia , Heliotropium , Proliferação de Células/efeitos dos fármacos , Terpenos/química , Cicatrização , Flavonoides/química , Movimento Celular/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Células Cultivadas , Células Epiteliais/efeitos dos fármacos
11.
Acta Biol Hung ; 69(3): 259-269, 2018 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-30257579

RESUMO

Heliotropium indicum L. belongs to the family Boraginaceae. The plant has been used as a folk medicine because it contains substances of various biological activities. It is also identified as a common weed which grows wildly in crop fields in tropical and subtropical regions of the world. However, there is little information on the allelopathic effect in this plant. Therefore, this study was undertaken to investigate the growth inhibitory effect and to identify the growth inhibitory substances in H. indicum. An aqueous methanol extract of H. indicum inhibited shoot and root growth of barnyard grass, foxtail fescue, timothy, cress, lettuce and rapeseed at concentrations higher than 10 mg dry weight equivalent extract/mL. The concentrations required for 50% growth inhibition (I50) of those test plants ranged from 3-282 mg dry weight equivalent extract/mL. The extract was then separated using a sequence of chromatographic fractionations and a growth inhibitory substance was isolated and identified by spectral analysis as methyl caffeate. Methyl caffeate inhibited the growth of lettuce and foxtail fescue at concentrations higher than 1.0 mM. The results suggest that methyl caffeate may contribute to the growth inhibitory effect of H. indicum and may play an important role in the allelopathic effect of H. indicum.


Assuntos
Ácidos Cafeicos/química , Ácidos Cafeicos/farmacologia , Heliotropium/química , Reguladores de Crescimento de Plantas/química , Reguladores de Crescimento de Plantas/farmacologia , Brassicaceae/efeitos dos fármacos , Heliotropium/metabolismo , Alface/efeitos dos fármacos , Estrutura Molecular , Reguladores de Crescimento de Plantas/metabolismo , Poaceae/efeitos dos fármacos
12.
Fish Shellfish Immunol ; 74: 76-83, 2018 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-29292197

RESUMO

In this study, we seek to identify flavonoids able to regulate the gene expression of a group of cytokines important for the control of infections in Atlantic salmon (Salmo salar). Particularly, we studied the potential immunomodulatory effects of two flavonoids, Alpinone and Pinocembrine, which were isolated and purified from resinous exudates of Heliotropium huascoense and Heliotropium sinuatum, respectively. The transcript levels of TNF-α and IL-1 (inflammatory cytokines), IFN-γ and IL-12 (T helper 1 type cytokines), IL4/13A (Th2-type cytokine), IL-17 (Th17 type cytokine) TGF-ß1 (regulatory cytokine) and IFN-α (antiviral cytokine) were quantified by qRT-PCR in kidneys of flavonoid-treated and control fish. We demonstrated that the administration of a single intramuscular dose of purified Alpinone increased the transcriptional expression of five cytokines, named TNF-α, IL-1, IFN-α, IFN-γ and TGF-ß1 in treated fish compared to untreated fish. Conversely, administration of purified Pinocembrine reduced the transcriptional expression of TNF-α, IL-1 and IL-12 in the kidney of treated fish. No other changes were observed. Interestingly, Alpinone also induced in vitro antiviral effects against Infectious Salmon Anaemia virus. Results showed that Alpinone but not Pinocembrine induces the expression of cytokines, which in vertebrates are essential to control viral infections while Pinocembrine reduces pro-inflammatory cytokines. Altogether results suggest that Alpinone is a good candidate to be further tested as immunostimulant and antiviral drug.


Assuntos
Antivirais/farmacologia , Citocinas/genética , Flavanonas/farmacologia , Flavonoides/farmacologia , Regulação da Expressão Gênica/imunologia , Imunomodulação , Salmo salar/imunologia , Animais , Antivirais/administração & dosagem , Citocinas/metabolismo , Proteínas de Peixes/genética , Proteínas de Peixes/metabolismo , Flavanonas/administração & dosagem , Flavonoides/administração & dosagem , Heliotropium/química , Distribuição Aleatória , Salmo salar/genética
14.
Bol. latinoam. Caribe plantas med. aromát ; 16(6): 578-585, nov. 2017. ilus, graf
Artigo em Inglês | LILACS | ID: biblio-914944

RESUMO

The flavonoid 3,5-dihydroxy-7-methoxyflavanone ((-)-alpinone) isolated from sticky resinous exudate of Heliotropium huascoense was evaluated as immunostimulatory in mammalian cells . Preliminary observations had showed that (-)-alpinone had increased the expression levels of pro-inflammatory cytokine transcripts in salmonid. Due to high morbidity and mortality that infectious diseases cause in humans, we evaluate the effect of (-)-alpinone as an immunostimulant in mammalian cells. Reactive oxygen species (ROS) are produced by macrophages activators for the destruction of pathogens; we evaluated (-)-alpinone effect in ROS generation and the proliferation of macrophages. The results showed that proliferation in Raw 264.7 cells treated with 10 and 25 µg/mL of (-)-alpinone had a significant increase in macrophage proliferation. In relation to ROS formation, cells treated with 1 and 5 µg/mL of (-)-alpinone, induce ROS formation in macrophages.


El flavonoide 3,5-dihidroxi-7-metoxiflavanona ((-)-alpinona) aislado del exudado resinoso de Heliotropium huascoense se evaluó como inmunoestimulador en células de mamíferos. Resultados preliminares habían demostrado que (-)-alpinona aumentaba los niveles de expresión de transcritos de citoquinas proinflamatorias en salmónidos. Debido a la alta morbilidad y mortalidad que causan las enfermedades infecciosas en los humanos, evaluamos el efecto de (-)-alpinona como inmunoestimulante en células de mamíferos. Dado que las especies de oxígeno reactivo (ROS) son producidas por macrófagos activados para la destrucción de patógenos, se evaluó el efecto de (- )-alpinona en la generación de ROS y la proliferación de macrófagos. Los resultados mostraron que la proliferación en células Raw264.7 tratadas con 10 y 25 µg / mL del flavonoíde tuvo un aumento significativo en la proliferación de macrófagos. En relación con la formación de ROS, las células tratadas con 1 y 5 µg/mL de (-)-alpinona, inducen la formación de ROS en los macrófagos.


Assuntos
Resinas Vegetais/farmacologia , Flavonoides/farmacologia , Heliotropium/química , Fatores Imunológicos/farmacologia , Mamíferos , Sais de Tetrazólio , Células Cultivadas , Espécies Reativas de Oxigênio , Proliferação de Células/efeitos dos fármacos , Macrófagos/metabolismo
15.
Bioorg Med Chem Lett ; 27(20): 4630-4634, 2017 10 15.
Artigo em Inglês | MEDLINE | ID: mdl-28927792

RESUMO

Two new compounds heliotropiumides A (1) and B (2), phenolamides each with an uncommon carbamoyl putrescine moiety, were isolated from the seeds of a naturalized Hawaiian higher plant, Heliotropium foertherianum Diane & Hilger in the borage family, which is widely used for the treatment of ciguatera fish poisoning. The structures of compounds 1 and 2 were characterized based on MS spectroscopic and NMR analysis, and DP4+ calculations. The absolute configuration (AC) of compound 1 was determined by comparison of its optical rotation with those reported in literature. Compound 2 showed inhibition against NF-κB with an IC50 value of 36µM.


Assuntos
Amidas/farmacologia , Benzofuranos/química , Heliotropium/química , Fenóis/química , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Amidas/química , Amidas/toxicidade , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antineoplásicos Alquilantes/química , Antineoplásicos Alquilantes/isolamento & purificação , Antineoplásicos Alquilantes/farmacologia , Benzofuranos/farmacologia , Benzofuranos/toxicidade , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Fungos/efeitos dos fármacos , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Heliotropium/metabolismo , Humanos , Espectroscopia de Ressonância Magnética , Conformação Molecular , NF-kappa B/antagonistas & inibidores , NF-kappa B/metabolismo , Fenóis/farmacologia , Fenóis/toxicidade , Extratos Vegetais/uso terapêutico , Putrescina/química , Intoxicação por Frutos do Mar/prevenção & controle
16.
Chem Res Toxicol ; 30(3): 851-858, 2017 03 20.
Artigo em Inglês | MEDLINE | ID: mdl-28125883

RESUMO

Pyrrolizidine alkaloids are among the most common poisonous plants affecting livestock, wildlife, and humans. Exposure of humans and livestock to toxic pyrrolizidine alkaloids through the intake of contaminated food and feed may result in poisoning, leading to devastating epidemics. During February 2014, 73 mixed breed female beef cows from the Galilee region of Israel were accidently fed pyrrolizidine alkaloid contaminated hay for 42 days, resulting in the sudden death of 24 cows over a period of 63 days. The remaining cows were slaughtered 2.5 months after the last ingestion of the contaminated hay. In this study, we report the histopathological analysis of the livers from five of the slaughtered cows and quantitation of pyrrolizidine alkaloid-derived DNA adducts from their livers and three livers of control cows fed with feed free of weeds producing pyrrolizidine alkaloids. Histopathological examination revealed that the five cows suffered from varying degrees of bile duct proliferation, fibrosis, and megalocytosis. Selected reaction monitoring HPLC-ES-MS/MS analysis indicated that (±)-6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine (DHP)-derived DNA adducts were formed in all five livers. The livers from the three control cows did not have any liver damage nor any indication of DHP-DNA adduct formed. These results confirm that the toxicity observed in these cattle was caused by pyrrolizidine alkaloid poisoning and that pyrrolizidine alkaloid-derived DNA adducts could still be detected and quantified in the livers of the chronically poisoned cows 2.5 months after their last exposure to the contaminated feed, suggesting that DHP-derived DNA adducts can serve as biomarkers for pyrrolizidine alkaloid exposure and poisoning.


Assuntos
Adutos de DNA/química , Heliotropium/fisiologia , Fígado/química , Plantas Tóxicas/toxicidade , Alcaloides de Pirrolizidina/química , Animais , Bovinos , Cromatografia Líquida , Fígado/patologia , Espectrometria de Massas em Tandem
17.
Curr Eye Res ; 42(3): 394-401, 2017 03.
Artigo em Inglês | MEDLINE | ID: mdl-27419531

RESUMO

OBJECTIVE: To evaluate the anti-cataract potential of an aqueous whole plant extract of Heliotropium indicum (HIE) on galactose-induced cataract in Sprague-Dawley rats. MATERIALS AND METHODS: Cataract scores were recorded in 3-week-old Sprague-Dawley rats in which cataract was being induced by an oral administration of 1500 mgkg-1 galactose twice daily for 4 weeks, and concurrently being treated with 30, 100, or 300 mgkg-1 HIE daily over the induction period. Fasting blood glucose was monitored at weekly intervals. Changes in body weight as well as total lens protein, lens glutathione, and superoxide dismutase (SOD) were determined initially, and at the end of the experimental period. Crystalline lens weight-to-body-weight ratio was also determined for the various treatment groups at the end of the experimental period. Preliminary phytochemical screening, total antioxidant capacity, and reducing power assays were conducted on HIE. RESULTS: The 30 and 100 mgkg-1 HIE-treated rats recorded significantly lower (p ≤ 0.05-0.001) cataract scores (indicating very significant delays in cataractogenesis by the 3rd and 4th weeks of treatment) and blood glucose levels. Rats with delayed cataractogenesis also exhibited significant (p ≤ 0.05-0.001) weight gain, and reduction in lens weight. Total lens proteins glutathione and SOD levels in the crystalline lens were also significantly preserved (p ≤ 0.01-0.001). HIE showed substantial antioxidant capacity and reducing power. CONCLUSION: The aqueous whole plant extract of Heliotropium indicum delays cataractogenesis at an optimum dose of 30 mgkg-1 in Sprague-Dawley rats.


Assuntos
Catarata/prevenção & controle , Heliotropium , Fitoterapia/métodos , Extratos Vegetais/uso terapêutico , Animais , Catarata/induzido quimicamente , Catarata/diagnóstico , Modelos Animais de Doenças , Proteínas do Olho/metabolismo , Feminino , Galactose/toxicidade , Cristalino/efeitos dos fármacos , Cristalino/metabolismo , Cristalino/patologia , Masculino , Ratos , Ratos Sprague-Dawley
18.
Bol. latinoam. Caribe plantas med. aromát ; 15(6): 422-428, nov. 2016. ilus, graf
Artigo em Inglês | LILACS | ID: biblio-907557

RESUMO

In this communication the antibacterial activity of filifolinol (1), naringenin (2) 3-O-methylgalangin (3) and pinocembrin (4) isolated from the resinous exudates of Heliotropium filifolium and H. sinuatum, were evaluated by flow cytometry against Staphylococcus aureus and Salmonella tiphymurium. The results showed that filifolinol (1) and naringenin (2) were inactive in the range of concentrations used (10 to 1000 ug/mL). On the other hand, pinocembrin (4) produced a decrease in cell surface at 500 ug/mL and the total disappearance of both bacterial populations at 1000 ug/mL. Also, 3-O-methylgalangin (3) showed the total disappearance at 1000 ug/mL of both bacterial populations and a decrease at 200 μg/mL for S. typhimurium and at 500 μg/mL for S. aureus.


En esta comunicación, la actividad antibacteriana de filifolinol (1), naringenina (2), 3-O-methylgalangina (3) y pinocembrina (4) aislados de los exudados resinosos de Heliotropium filifolium y H. sinuatum, fueron evaluados por citometría de flujo frente a Staphylococcus aureus y Salmonella tiphymurium. Los resultados mostraron que filifolinol (1) y naringenina (2) fueron inactivos en el intervalo de concentraciones usadas (10 a 1000 μg / mL). Por otro lado, pinocembrina (4) produce una disminución de la superficie de las células a 500 ug/mL y la desaparición total de ambas poblaciones bacterianas a 1.000 ug/mL. También, 3-O-metilgalangina (3) mostró la desaparición total a 1.000 ug / mL tanto de ambas poblaciones de bacterias y una disminución a 200 ug/mL para S. typhimurium y en 500 μg/mL para S. aureus.


Assuntos
Antibacterianos/farmacologia , Heliotropium/química , Óleos Voláteis/farmacologia , Salmonella typhimurium , Staphylococcus aureus , Citometria de Fluxo , Monoterpenos/farmacologia , Exsudatos de Plantas/farmacologia , Sesquiterpenos/farmacologia
19.
Biomed Res Int ; 2016: 3818945, 2016.
Artigo em Inglês | MEDLINE | ID: mdl-27597961

RESUMO

The present study deals with the antimicrobial, antioxidant, and functional group analysis of Heliotropium bacciferum extracts. Disc diffusion susceptibility method was followed for antimicrobial assessment. Noteworthy antimicrobial activities were recorded by various plant extracts against antibiotic resistant microorganisms. Plant flower extracts antioxidant activity was investigated against 2, 2-diphenyl-1-picryl hydrazyl radical by ultraviolet spectrophotometer (517 nm). Plant extracts displayed noteworthy radical scavenging activities at all concentrations (25-225 µg/mL). Notable activities were recorded by crude, chloroform and ethyl acetate extracts up to 88.27% at 225 µg/mL concentration. Compounds functional groups were examined by Fourier transform infrared spectroscopic studies. Alkanes, alkenes, alkyl halides, amines, carboxylic acids, amides, esters, alcohols, phenols, nitrocompounds, and aromatic compounds were identified by FTIR analysis. Thin layer chromatography bioautography was carried out for all plant extracts. Different bands were separated by various solvent systems. The results of the current study justify the use of Heliotropium bacciferum in traditional remedial herbal medicines.


Assuntos
Antibacterianos/administração & dosagem , Fenômenos Fisiológicos Bacterianos/efeitos dos fármacos , Compostos de Bifenilo/química , Heliotropium/química , Picratos/química , Extratos Vegetais/administração & dosagem , Extratos Vegetais/química , Antibacterianos/química , Bioensaio/métodos , Compostos de Bifenilo/isolamento & purificação , Sobrevivência Celular/efeitos dos fármacos , Sobrevivência Celular/fisiologia , Sequestradores de Radicais Livres/química , Radicais Livres/química , Radicais Livres/isolamento & purificação , Heliotropium/classificação , Picratos/isolamento & purificação , Plantas Medicinais/química , Plantas Medicinais/classificação , Especificidade da Espécie , Espectroscopia de Infravermelho com Transformada de Fourier/métodos
20.
Methods Mol Biol ; 1391: 103-12, 2016.
Artigo em Inglês | MEDLINE | ID: mdl-27108312

RESUMO

Heliotropium kotschyi (Ramram) is an important endangered medicinal plant distributed in the Kingdom of Bahrain. Plant tissue culture technique is applied for ex situ conservation study. Nodal stem segments are cultured in modified MS media supplemented with various combination and concentration of plant growth regulators (PGRs). Plants are regenerated via shoot organogenesis from the nodal meristems. Plants are regenerated in three different steps: initial shoot development, shoot multiplication, and rooting. After 4 weeks of culture, 100 % explants respond to shoot initiation on the medium containing 8.88 µM BAP and 5.71 µM IAA. The highest frequency of shoot regeneration is observed in the same media after second subculture of shoots. The highest rooting frequency is observed in the presence of 2.85 µM IAA. After root development, the plantlets are transferred to pots filled with soil and 60 % of plants survived after 45 days. This plant regeneration protocol is of great value for rapid desert plant propagation program.


Assuntos
Heliotropium/fisiologia , Plantas Medicinais/fisiologia , Compostos de Benzil/metabolismo , Meios de Cultura/metabolismo , Espécies em Perigo de Extinção , Ácidos Indolacéticos/metabolismo , Reguladores de Crescimento de Plantas/metabolismo , Raízes de Plantas/fisiologia , Brotos de Planta/fisiologia , Purinas/metabolismo , Regeneração , Técnicas de Cultura de Tecidos/métodos
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