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1.
J Agric Food Chem ; 67(37): 10448-10457, 2019 Sep 18.
Artigo em Inglês | MEDLINE | ID: mdl-31453693

RESUMO

Carabrone is isolated from Carpesium macrocephalum Franch. et Sav, which has good fungicidal activity, especially for Gaeumannomyces graminis (Get). According to previous studies, we speculated that carabrone targets the mitochondrial enzyme complex III of Get. To elucidate the mode of action, we used carabrone to induce oxidative stress and apoptosis in Get. Incubation with carabrone reduced the burst of reactive oxygen species (ROS) and mitochondrial membrane potential, as well as phosphatidylserine release. Carabrone caused ROS accumulation in mycelia by inhibiting the activity of antioxidase enzymes, among which inhibition of glutathione reductase (GR) activity was most obvious. The catalytic center of GR consists of l-cysteine residues that react with the α-methylene-γ-butyrolactone active site of carabrone. Additionally, a positive TUNEL reaction led to diffusion of the DNA electrophoresis band and upregulation of Ggmet1 and Ggmet2. We propose that carabrone inhibits antioxidant enzymes and promotes ROS overproduction, which causes membrane hyperpermeability, release of apoptotic factors, activation of the mitochondria-mediated apoptosis pathway, and fungal cell apoptosis.


Assuntos
Apoptose/efeitos dos fármacos , Ascomicetos/efeitos dos fármacos , Fungicidas Industriais/farmacologia , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/farmacologia , Ascomicetos/citologia , Ascomicetos/metabolismo , Asteraceae/química , Proteínas Fúngicas/metabolismo , Glutationa Redutase/metabolismo , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Mitocôndrias/efeitos dos fármacos , Mitocôndrias/metabolismo , Espécies Reativas de Oxigênio/metabolismo
2.
Zhongguo Zhong Yao Za Zhi ; 44(13): 2727-2735, 2019 Jul.
Artigo em Chinês | MEDLINE | ID: mdl-31359683

RESUMO

Xixiancao( Siegesbeckiae Herba) has the effect of treating ischemic stroke( IS),however,the mechanism has not been fully elucidated. In this study,combined with Lipinski's five principles and Veber oral bioavailability rules,68 chemical components of Xixiancao were obtained by database and literature search. Based on the reverse targeting,248 potential targets were obtained and mapped it to the ischemic stroke target set,47 potential targets for the treatment of ischemic stroke were obtained. Molecular docking technique was used to verify that the Xixiancao component has good binding activity to potential targets. GO enrichment analysis and pathway analysis were performed on potential targets using Clue GO. GO enrichment analysis showed that Xixiancao was mainly involved in life processes such as neuronal apoptosis,cholesterol storage and blood pressure regulation. Pathway analysis showed that Xixiancao may promote vascular repairing and regeneration by regulating the expression of ADAMTS1,FLT1 and KDR in VEGFA-VEGFR2 signaling pathway,activate cell survival signals and inhibit neuronal apoptosis by regulating the expression of CAMK2 AA,MDM2,MAPK1,MAPK3,CDK5 and MAPK10 in brain-derived neurotrophic factor signaling pathway and PI3 K-Akt signaling pathway. Lipid homeostasis and inflammation may also be regulated by Xixiancao through regulating the expression of ESR1,NR1 H3,PPARA,PPARG in the nuclear receptor signaling pathway. In addition,Xixiancao could also prevent platelet aggregation by regulating the expression of ITGA2 B,F2,F10,and ALB,and play an antithrombotic role. The results of this study indicate that Xixiancao plays an important role in the treatment of ischemic stroke mainly through anti-thrombosis,promoting angiogenesis,protecting neurons,anti-inflammatory and regulating blood pressure and lipids.


Assuntos
Asteraceae/química , Isquemia Encefálica/tratamento farmacológico , Medicamentos de Ervas Chinesas/uso terapêutico , Acidente Vascular Cerebral/tratamento farmacológico , Humanos , Simulação de Acoplamento Molecular , Transdução de Sinais
3.
Planta Med ; 85(11-12): 1008-1015, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31266068

RESUMO

One new natural monoterpene, 5-O-ß-d-glucopyranosyl-2-hydroxy-p-cymene (1: ), and 11 known compounds were isolated through a biologically oriented approach from the aerial parts of Phagnalon sordidum L. The most active extract and fractions were selected using 3 complementary antioxidant activity assays. Results and the different methods were compared by relative antioxidant capacity index. In addition, the most active extract of P. sordidum was subjected to liquid chromatography coupled with electrospray ionization hybrid linear ion trap quadrupole Orbitrap mass spectrometry to quantify secondary metabolites. Antioxidant activities of ethyl acetate extract, and purified 3,4-dihydroxyacetophenone (3: ) and nebrodenside A (7: ) were demonstrated by in vitro cell free model assays, and their protective effect against H2O2-induced oxidative stress in a HepG2 (human hepatocellular carcinoma) cell line was established.


Assuntos
Antioxidantes/farmacologia , Asteraceae/química , Componentes Aéreos da Planta/química , Extratos Vegetais/farmacologia , Antioxidantes/isolamento & purificação , Células Hep G2/efeitos dos fármacos , Humanos , Espectroscopia de Ressonância Magnética , Estresse Oxidativo/efeitos dos fármacos , Extratos Vegetais/isolamento & purificação
4.
Rev Inst Med Trop Sao Paulo ; 61: e33, 2019 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-31269109

RESUMO

Leishmaniasis is a disease that affects millions of people and it is an important public health problem. The drugs currently used for the treatment of leishmaniasis present undesirable side effects and low efficacy. In this study, we evaluated the in vitro activity of Melampodium divaricatum (MD-EO) and Casearia sylvestris (CS-EO) essential oils (EO) against promastigote and amastigote forms of Leishmania amazonensis. Sesquiterpenes E-caryophyllene (56.0%), germacrene D (12.7%) and bicyclogermacrene (9.2%) were identified as the main components of MD-EO, whereas E-caryophyllene (22.2%), germacrene D (19.6%) and bicyclogermacrene (12.2%) were the main constituents of CS-EO. CS-EO and E-caryophyllene were active against promastigote forms of L. amazonensis (IC50 24.2, 29.8 and 49.9 µg/mL, respectively). However, MD-EO, CS-EO and E-caryophyllene were more active against amastigote forms, with IC50 values of 10.7, 14.0, and 10.7 µg/mL, respectively. E-caryophyllene presented lower cytotoxicity against macrophages J774-A1 (CC50 of 62.1 µg/mL) than the EO. The EOs and E-caryophyllene should be further studied for the development of new antileishmanial drugs.


Assuntos
Antiprotozoários/farmacologia , Asteraceae/química , Casearia/química , Leishmania mexicana/efeitos dos fármacos , Óleos Voláteis/farmacologia , Antiprotozoários/isolamento & purificação , Humanos , Concentração Inibidora 50 , Leishmania mexicana/isolamento & purificação , Testes de Sensibilidade Parasitária
5.
Plant Foods Hum Nutr ; 74(3): 350-357, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31209702

RESUMO

Thirteen fruits, eight legumes and three tubers consumed in the Andean regions of Ecuador were studied to determine their bioactive compounds, organic acids, sugars content, total antioxidant capacity, as well as to determine which among them showed the greatest contribution in terms of antioxidant activity and which compounds contributed to it. Among fruits, taxo fruits (Passiflora mollissima (Kunth) L.H. Bailey) presented the highest values of total phenolic, carotene content, and total antioxidant capacity. The ají ratón (Capsicum chinense Jacq) showed the highest content of vitamin C. Taxo showed the highest content of ß carotene, whilst lycopene was identified only in guayaba fruits (Psidium guajava L.) and ají ratón was the principal source of lutein. In legumes, chocho perla (Lupinus mutabilis Sweet) showed the highest values for both total phenolic and flavonoid content, whilst frejol negro (Phaseolus vulgaris L.) and frejol canario (Vigna unguiculata (L.) Walp) showed the highest values for FRAP and DPPH assay, respectively. Between tubers, the jícama (Smallanthus sonchifolius (Poepp.) H. Rob.) had the majors values in terms of total phenolic, flavonoid content, and total antioxidant capacity. In terms of total antioxidant capacity, taxo fruits have the highest contribution in terms of total antioxidant capacity, whilst the dendogram shown the occurrence of five distinct groups in which taxo was located in the first largest group. Our data contributing towards gaining better knowledge about the Andean Ecuadorian diet and the composition of Andean food in order to estimate dietary intakes of health-promoting components.


Assuntos
Antioxidantes/análise , Asteraceae/química , Capsicum/química , Fabaceae/química , Promoção da Saúde , Passiflora/química , Ácido Ascórbico/análise , Carotenoides/análise , Equador , Flavonoides/análise , Frutas/química , Fenóis/análise , Compostos Fitoquímicos/análise , Tubérculos/química , beta Caroteno/análise
6.
Food Chem ; 296: 86-93, 2019 Oct 30.
Artigo em Inglês | MEDLINE | ID: mdl-31202310

RESUMO

Microgreens are an emerging class of vegetables, which have become increasingly important in the agri-food market in recent years, and contain a number of macro- and micro-nutrients. This paper presents a rapid method for the elemental analysis of microgreens based on total reflection X-ray fluorescence (TXRF) spectroscopy, without preliminary sample digestion. The following elements were detected and quantified simultaneously for six microgreen genotypes, belonging to Asteraceae and Brassicaceae: P, S, K, Ca, Cl, Mn, Fe, Ni, Cu, Zn, Br, Rb, Sr. The limit of detection (LOD) varied depending on the element and ranged between 0.1 mg kg-1 for Sr and 42 mg kg-1 for P. The method was validated using certified standards, and results compared with those obtained using a conventional ICP-AES method requiring sample digestion. The paper also presents the advantages and disadvantages of the two techniques.


Assuntos
Espectrometria por Raios X/métodos , Oligoelementos/análise , Verduras/química , Asteraceae/química , Asteraceae/metabolismo , Brassicaceae/química , Brassicaceae/metabolismo , Limite de Detecção
7.
Plant Physiol Biochem ; 141: 183-192, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31174035

RESUMO

The present study is focused on the characterization of yacon [Smallanthus sonchifolius (Poepp. et Endl.) H. Robinson] accessions from different geographic origins (Bolivia, Ecuador, and Peru) by iPBS markers and metabolomic fingerprinting. The results showed that the number of amplified polymorphic fragment levels ranged from 20 up to 27 with a level of polymorphism ranging from 80 to 100%. Five of the iPBS primers used in this study provided no specific banding pattern able to discriminate between the different yacon accessions. However, two iPBS primer pairs were able to separate Peru accessions from those of Ecuador and Bolivia. The UPLC-HRMS/MS-based metabolomic fingerprinting showed highly similar metabolomic fingerprints characterized by the accumulation of high quantities of sesquiterpene lactones and diterpenes, but no apparent geographic clustering. The present study demonstrates that yacon accessions from different geographical origins maintained ex situ (in the Czech Republic) present a rather low chemical and genetic diversity.


Assuntos
Antioxidantes/química , Asteraceae/química , Diterpenos/química , Lactonas/química , Extratos Vegetais/química , Sesquiterpenos/química , Asteraceae/genética , Bolívia , Análise por Conglomerados , República Tcheca , Equador , Variação Genética , Geografia , Glicosilação , Espectrometria de Massas , Metabolômica , Análise Multivariada , Mapeamento de Peptídeos , Peru , Raízes de Plantas/química , Retroelementos
8.
Phytochemistry ; 165: 112047, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31203102

RESUMO

Four undescribed lignans and two undescribed sesquiterpenic acids, together with three known compounds (hypochoeroside C, hypochoeroside D, and 5-O-caffeoylshikimic acid) were isolated from the roots of Hypochaeris radicata subsp. neapolitana (Asteraceae, Cichorieae). The lignans were identified as 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranoside, 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranosyl-2'-O-methacrylate, (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-7,8,7',8'-tetrahydronaphtho [8,8'-c]furan-1(3H)-one, and (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-8'-(hydroxymethyl)-7,8,7',8'-tetrahydronaphthalen-8-carboxylic acid. The two sesquiterpenic acids were identified as the ring open precursors of hypochoerosides C and D. Structures were elucidated using NMR and HRMS. Absolute configurations of (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-7,8,7',8'-tetrahydronaphtho [8,8'-c]furan-1(3H)-one and (7S,8R,8'R)-7-(3,4-dihydroxyphenyl)-3',4'-dihydroxy-8'-(hydroxymethyl)-7,8,7',8'-tetrahydronaphthalen-8-carboxylic acid were determined using electronic circular dichroism (ECD) spectroscopy. 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranoside was evaluated for its anti-proliferative activity against myeloma cell lines MM1S, U266, and NCI-H929 and showed cytotoxicity at 100 mM against MM1S strain. No neurotoxicity was observed for major compounds 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranoside, hypochoeroside C, and hypochoeroside D in a fluorescence assay measuring neurite outgrowth in dorsal root ganglion (DRG) neurons. Additionally, compounds 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranoside, hypochoeroside C, hypochoeroside D, and hypochoerosidic acid D were quantified in unstressed and drought-stressed plants using HPLC-DAD. Drought-stressed plants were found to contain lower concentrations of the lignan 4-(3,4-dihydroxybenzyl)-2-(3,4-dihydroxyphenyl)tetrahydrofuran-3-carboxy-O-ß-D-glucopyranoside and sesquiterpene lactone hypochoeroside C.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Asteraceae/química , Lactonas/farmacologia , Lignanas/farmacologia , Mieloma Múltiplo/tratamento farmacológico , Sesquiterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Lactonas/química , Lactonas/isolamento & purificação , Lignanas/química , Lignanas/isolamento & purificação , Estrutura Molecular , Mieloma Múltiplo/patologia , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Relação Estrutura-Atividade
9.
Chem Biodivers ; 16(8): e1900278, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31207097

RESUMO

Using synthetic chemicals in industry and agriculture has led to several environmental problems. Thus, plant products derived from volatile oils (VOs) could be a potential green source for bioherbicides. Little is known about the VOs of Lactuca serriola. Hence, the present study aimed to characterize the VOs chemical composition from the aerial parts of L. serriola, assessment of antioxidant activity, and evaluate allelopathic potential against the noxious weed Bidens pilosa. The VOs were extracted by hydrodistillation and analyzed by GC/MS. The VOs from the Egyptian ecospecies of L. serriola were found to comprise 34 compounds mainly oxygenated sesquiterpenes and diterpenes. The major compounds were isoshyobunone (64.22 %), isocembrol (17.35 %), and alloaromadendrene oxide-1 (7.32 %). So, L. serriola can be considered as a good source for isoshyobunone, considering that it has a much higher concentration than any other plants. Also, this plant has a high content of the oxygenated diterpene compound, isocembrol, which is rarely found in the VOs of most plants. The VOs expressed strong antioxidant activity. Also, for the first time, our results showed a strong allelopathic activity of VOs from L. serriola on germination and seedling growth of the noxious weed, B. pilosa. We suppose that the activity of the VOs from L. serriola could be attributed to these previously mentioned major compounds, as they represent about 89 % of the total identified oil constituents. Nevertheless, to evaluate these compounds as new allelochemicals, further study is needed to test the allelopathic activity of authenticated standard of these compounds either singular or in combination on several weeds as well as evaluate the safety, and improve the efficacy and stability at the field scale.


Assuntos
Antioxidantes/química , Asteraceae/química , Diterpenos/química , Óleos Voláteis/química , Sesquiterpenos/química , Asteraceae/metabolismo , Bidens/crescimento & desenvolvimento , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Germinação/efeitos dos fármacos , Óleos Voláteis/farmacologia , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Extratos Vegetais/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia
10.
Fitoterapia ; 136: 104170, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31085308

RESUMO

A total of thirteen sesquiterpenoids with diverse skeletons including four new sesquiterpenoids, glandulosines A - D (1-4), a new natural product, glandulosine E (5), and eight known sesquiterpene lactones (6-13) were isolated from the roots of Cichorium glandulosum Boiss. et Huet (Asteraceae). Their structures were determined by extensive spectroscopic experiments including NMR, electronic circular dichroism (ECD), calculated ECD, Rh2(OCOCF3)4-induced ECD, and single-crystal X-ray diffraction analysis, as well as chemical methods. This is the first report of the crystal structure of 11ß,13-dihydrolactucin (11). Thirteen isolated sesquiterpenoids (1-13) were evaluated for their anti-inflammatory activities in vitro, and three guaiane sesquiterpene lactones, glandulosine E (5), scorzoside (9), and lactucin (10) showed moderate inhibitory activity against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages.


Assuntos
Anti-Inflamatórios/farmacologia , Asteraceae/química , Raízes de Plantas/química , Sesquiterpenos/farmacologia , Animais , Anti-Inflamatórios/isolamento & purificação , China , Macrófagos/efeitos dos fármacos , Camundongos , Estrutura Molecular , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7 , Sesquiterpenos/isolamento & purificação
11.
Phytother Res ; 33(6): 1627-1638, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-31069872

RESUMO

Milk thistle (Silybum marianum) is a medicinal plant from the Asteraceae family. Silymarin is the major constituent of milk thistle extract and is a mixture of some flavonolignans such as silybin, which is the most active component of silymarin. It is most commonly known for its hepatoprotective effect. Also, studies have shown other therapeutic effects such as anticancer, anti-Alzheimer, anti-Parkinson, and anti-diabetic, so its safety is very important. It has no major toxicity in animals. Silymarin was mutagen in Salmonella typhimurium strains in the presence of metabolic enzymes. Silybin, silydianin, and silychristin were not cytotoxic and genotoxic at concentration of 100 µM. Silymarin is safe in humans at therapeutic doses and is well tolerated even at a high dose of 700 mg three times a day for 24 weeks. Some gastrointestinal discomforts occurred like nausea and diarrhea. One clinical trial showed silymarin is safe in pregnancy, and there were no anomalies. Consequently, caution should be exercised during pregnancy, and more studies are needed especially in humans. Silymarin has low-drug interactions, and it does not have major effects on cytochromes P-450. Some studies demonstrated that the use of silymarin must be with caution when co-administered with narrow therapeutic window drugs.


Assuntos
Cardo Mariano/química , Extratos Vegetais/uso terapêutico , Silimarina/uso terapêutico , Animais , Antioxidantes/efeitos adversos , Antioxidantes/isolamento & purificação , Antioxidantes/uso terapêutico , Antioxidantes/toxicidade , Asteraceae/química , Asteraceae/classificação , Sistema Enzimático do Citocromo P-450/metabolismo , Citoproteção/efeitos dos fármacos , Dano ao DNA/efeitos dos fármacos , Interações de Medicamentos , Feminino , Humanos , Hipoglicemiantes/efeitos adversos , Hipoglicemiantes/uso terapêutico , Fígado/efeitos dos fármacos , Cardo Mariano/efeitos adversos , Degeneração Neural/prevenção & controle , Extratos Vegetais/efeitos adversos , Gravidez , Silimarina/efeitos adversos
12.
Molecules ; 24(9)2019 May 01.
Artigo em Inglês | MEDLINE | ID: mdl-31052362

RESUMO

Four new sesquiterpenoids (1-4) and six known sesquiterpenoids (5-10), were isolated from the EtOAc phase of the ethanolic extract of Ainsliaea yunnanensis. Their structures were established by spectroscopic methods, including 1-D, 2-D NMR and HPLC-MS. All compounds were tested for their anti-inflammatory effect by the inhibition of the activity of NLRP3 inflammasome by blocking the self-slicing of pro-caspase-1, which is induced by nigericin, then the secretion of mature IL-1ß, mediated by caspase-1, was suppressed. Unfortunately none of the compounds showed an anti-inflammatory effect.


Assuntos
Anti-Inflamatórios/química , Asteraceae/química , Proteína 3 que Contém Domínio de Pirina da Família NLR/metabolismo , Sesquiterpenos/química , Anti-Inflamatórios/farmacologia , Caspase 1/metabolismo , Linhagem Celular , Cromatografia Líquida de Alta Pressão , Regulação da Expressão Gênica/efeitos dos fármacos , Humanos , Interleucina-1beta/metabolismo , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Nigericina/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Sesquiterpenos/farmacologia
13.
J Food Sci ; 84(6): 1631-1637, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-31059127

RESUMO

The effects of Gynura bicolor aqueous extract (GAE) upon glycemic control, coagulation disorder, lipid accumulation, and glycative, oxidative, and inflammatory stresses in diabetic mice were investigated. Mice were treated with streptozotocin to induce type 1 diabetes. Diabetic mice were divided into four groups, consumed GAE at 0%, 0.25%, 0.5%, or 1%. Normal group consumed standard mouse basal diet. After 8-week treatments, mice were sacrificed after overnight fasting. Results showed that GAE supplement at 0.5% and 1% decreased plasma glucose level and increased plasma insulin level. Diabetes lowered plasma level of protein C and anti-thrombin III; and raised plasminogen activator inhibitor-1 activity and fibrinogen level in plasma. GAE supplement at 0.5% and 1% reversed these alterations. Histological data, assayed by Oil Red O stain, indicated that GAE supplement decreased lipid accumulation in liver. GAE supplement at 0.5% and 1% reduced aldose reductase activity in heart and kidney; and lowered the levels of carboxymethyllysine and pentosidine in plasma and two organs. Diabetes decreased glutathione content, and increased reactive oxygen species, interleukin (IL)-1ß, IL-6, and tumor necrosis factor-α production in heart and kidney. GAE supplement at three test doses reversed these changes. Diabetes upregulated the mRNA expression of p38 and nuclear factor kappa (NF-κ)B in heart and kidney. GAE supplement suppressed the mRNA expression of both p38 and NF-κB. These novel findings suggest that Gynura bicolor is a potent functional food for diabetic prevention or alleviation.


Assuntos
Antidiuréticos/administração & dosagem , Asteraceae/química , Diabetes Mellitus Experimental/tratamento farmacológico , Extratos Vegetais/administração & dosagem , Animais , Arginina/análogos & derivados , Arginina/metabolismo , Glicemia/metabolismo , Diabetes Mellitus Experimental/metabolismo , Glutationa/metabolismo , Humanos , Rim/efeitos dos fármacos , Rim/metabolismo , Fígado/efeitos dos fármacos , Fígado/metabolismo , Lisina/análogos & derivados , Lisina/metabolismo , Masculino , Camundongos , Camundongos Endogâmicos BALB C , NF-kappa B/metabolismo , Espécies Reativas de Oxigênio/metabolismo
14.
Chem Biodivers ; 16(7): e1900093, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-31095892

RESUMO

Twelve chlorogenic acid derivatives and two flavones were isolated from Moquiniastrum floribundum (Asteraceae, other name: Gochnatia floribunda). Compounds were evaluated in relation to their cytotoxicity and antiradical properties. Cytotoxicity was not observed for compounds, however, chlorogenic acid derivatives showed antiradical activity and were more active than the Trolox standard. Quinic acid esterified with caffeoyl group at C-4 position showed higher antiradical activity compared to acylation at C-3 or C-5 positions. Additional caffeoyl groups esterified in quinic acid increase the antiradical activity observed for 4-caffeoylquinic acid. Excepted to 3,4-dicaffeoylquinic acid methyl ester, methyl ester derivatives show higher capacity of trapping radicals than their respective acids. Consequently, the presence of caffeoyl group at C-4 position of quinic acid is suggested as fundamental to obtain the highest antiradical activity.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Antioxidantes/farmacologia , Asteraceae/química , Compostos de Bifenilo/antagonistas & inibidores , Picratos/antagonistas & inibidores , Ácido Quínico/análogos & derivados , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antioxidantes/química , Antioxidantes/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Células HCT116 , Humanos , Estrutura Molecular , Ácido Quínico/química , Ácido Quínico/isolamento & purificação , Ácido Quínico/farmacologia , Relação Estrutura-Atividade
15.
Bol. latinoam. Caribe plantas med. aromát ; 18(3): 223-238, mayo 2019. ilus
Artigo em Inglês | LILACS | ID: biblio-1007927

RESUMO

Plants of the genera Werneria (Asteraceae) and Xenophyllum (genus extracted from Werneria) are used in traditional medicine of Latin America for the treatment of mountain sickness, hypertension and gastrointestinal disorders. Only a small number of species of these genera have been studied, leading to the isolation of compounds belonging to the classes of benzofurans, chromenes, acetophenones, coumarates, diterpenes and pyrrolizidine alkaloids. Some of the plant extracts and/or compounds have shown antimicrobial, anti-HIV, hypotensive and photoprotective activities.


Las plantas de los géneros Werneria (Asteraceae) y Xenophyllum (género extraido de Werneria) son usadas en la medicina tradicional de América Latina para el tratamiento del mal de montaña, hipertensión y desórdenes gastrointestinales. Solo un pequeño número de especies de estos géneros ha sido investigado, lográndose aislar compuestos que pertenecen a las clases de benzofuranos, cromenos, acetofenonas, cumaratos, diterpenos y alcaloides pirrolizidínicos. Algunos de los extractos y/o compuestos de dichas plantas han mostrado actividades antimicrobianas, anti-HIV, hipotensoras y fotoprotectoras.


Assuntos
Plantas Medicinais/química , Extratos Vegetais/uso terapêutico , Asteraceae/química , Acetofenonas/química , Terpenos/análise , Benzopiranos/química , Flavonoides/química , Ácido Clorogênico/química , Ácidos Cumáricos/química , Alcaloides/química , Doença da Altitude/tratamento farmacológico , Hipertensão/tratamento farmacológico , Medicina Tradicional
16.
Bol. latinoam. Caribe plantas med. aromát ; 18(3): 277-288, mayo 2019. ilus
Artigo em Inglês | LILACS | ID: biblio-1007989

RESUMO

Neurolaena lobata (L.) R.Br. ex Cass. (Asteraceae)Is a popular folk remedy for in Central America. The plant is of commercial value in Guatemala but so far there is not any monograph to guide regional laboratories on ensuring identity and chemical tests for this species. As identity test we here run macro and micro morphoanatomical studies of the characters of the vegetative organs. We also developed standard chemical tests for quality by both TLC and HPLC for infusions and tinctures of varying alcoholic strength. Their radical scavenging activities in DPPH and NO were also measured. Macro and micro morphoanatomical characters of the vegetative organs present a set of characteristics to facilitate the identification of dry powdered samples of this species. We developed optimal conditions for the TLC and HPLC phytochemical fingerprints of the 4 most common pharmacopoeial liquid herbal preparations from this herbal drug, namely infusion, 70%, 45% and 20% hydroalcoholic tinctures. Our work provides the Latin-American industry with a set of analyses to establish the identity and chemistry of N. lobata samples for quality control purposes.


Neurolaena lobata (L.) R.Br. ex cass. (Asteraceae) es un remedio popular popular en América Central. La planta tiene un valor comercial en Guatemala, pero hasta el momento no existe una monografía que guíe a los laboratorios regionales para garantizar la identidad y las pruebas químicas para esta especie. Como prueba de identidad proponemos estudios macro y micro morfoanatómicos de los caracteres de los órganos vegetativos. También desarrollamos pruebas químicas de calidad mediante CCF y CLAR para infusiones y tinturas de grado alcohólico variable. También se midieron sus actividades de captación de radicales en DPPH y NO. Los caracteres macro y micro morfoanatómicos de los órganos vegetativos presentan un conjunto de características para facilitar la identificación de muestras de polvo seco de esta especie. Desarrollamos condiciones óptimas para las huellas dactilares fitoquímicas de CCF y CLAR de las 4 preparaciones herbales líquidas farmacopéicas más comunes de esta droga herbal, a saber, infusión, 70%, 45% y 20% tinturas hidroalcohólicas. Nuestro trabajo proporciona a la industria latinoamericana un conjunto de análisis base para establecer la identidad y la química de las muestras de N. lobata con fines de control de calidad.


Assuntos
Asteraceae/anatomia & histologia , Asteraceae/química , Compostos Fitoquímicos/análise , Controle de Qualidade , Espectrofotometria Ultravioleta , Depuradores de Radicais Livres , Cromatografia Líquida de Alta Pressão , Cromatografia em Camada Delgada , Asteraceae/ultraestrutura , Guatemala , Microscopia
17.
Molecules ; 24(8)2019 Apr 24.
Artigo em Inglês | MEDLINE | ID: mdl-31022860

RESUMO

Carpesium divaricatum Sieb. & Zucc. has a long history of use as both a medicinal and a food plant. However, except for terpenoids, its chemical constituents have remained poorly investigated. The composition of hydroalcoholic extract from aerial parts of C. divaricatum was analyzed by HPLC-DAD-MSn, revealing the presence of numerous caffeic acid derivatives that were formerly unknown constituents of the plant. In all, 17 compounds, including commonly found chlorogenic acids and rarely occurring butyryl and methylbutyryl tricaffeoylhexaric acids, were tentatively identified. Fractionation of lipophilic extract from cultivated shoots led to the isolation of 12-oxo-phytodienoic acid (12-OPDA), which is a newly identified constituent of the plant. The compound, at concentrations of 0.5, 1.0, and 2.5 µM, significantly reduced IL-8, IL-1ß, TNFα, and CCL2 excretion by lipopolysaccharide (LPS)-stimulated human neutrophils. Reactive oxygen species (ROS) production induced by f-MLP was also significantly diminished in the neutrophils pretreated by 12-OPDA. The newly identified constituents of the plant seem to be partly responsible for its pharmacological activity and elevate the value of C. divaricatum as a potential functional food.


Assuntos
Asteraceae/química , Ácidos Cafeicos/química , Ácido Clorogênico/química , Ácidos Graxos Insaturados/química , Ácidos Cafeicos/isolamento & purificação , Ácidos Cafeicos/farmacologia , Quimiocina CCL2/genética , Ácido Clorogênico/isolamento & purificação , Cromatografia Líquida de Alta Pressão , Ácidos Graxos Insaturados/isolamento & purificação , Ácidos Graxos Insaturados/farmacologia , Regulação da Expressão Gênica/efeitos dos fármacos , Humanos , Interleucina-8/genética , Lipopolissacarídeos/farmacologia , Neutrófilos/efeitos dos fármacos , Componentes Aéreos da Planta/química , Brotos de Planta/química , Espécies Reativas de Oxigênio/química , Fator de Necrose Tumoral alfa/genética
18.
Molecules ; 24(8)2019 Apr 24.
Artigo em Inglês | MEDLINE | ID: mdl-31022871

RESUMO

Essential oils (EOs) have gained increasing attention due to their pharmacological effectiveness, and they also constitute some of the most popular natural products. In this study, we present the chemical characterization of the EO from Phania matricarioides and the in vitro activity/selectivity against a wide panel of bacteria, fungi and parasitic protozoa. Forty-five compounds were identified in the studied EO, of which lavandulyl acetate (40.1%) and thymyl isobutyrate (13.9%) were the major components. The EO did not inhibit bacterial or fungal growth at the maximum concentration tested (64 µg/mL), although it displayed activity on all evaluated protozoa (IC50 values ranging from 2.2 to 56.6 µg/mL). In parallel, the EO demonstrated a noteworthy cytotoxic activity against peritoneal macrophages (CC50 values of 28.0 µg/mL). The most sensitive microorganism was Trypanosoma cruzi, which had a superior activity (IC50 = 2.2 µg/mL) and selectivity (SI = 13) in respect to other parasitic protozoa and the reference drug (p < 0.05). Further in vivo studies are needed to evaluate the potential use of this EO and the main compounds as antitrypanosomal agents. To our knowledge, this is the first report of chemical characterization and antimicrobial assessment of the EO from P. matricarioides.


Assuntos
Asteraceae/química , Proliferação de Células/efeitos dos fármacos , Macrófagos Peritoneais/efeitos dos fármacos , Óleos Voláteis/química , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antiparasitários/química , Antiparasitários/isolamento & purificação , Antiparasitários/farmacologia , Fungos/efeitos dos fármacos , Fungos/patogenicidade , Humanos , Testes de Sensibilidade Microbiana , Óleos Voláteis/isolamento & purificação , Óleos Voláteis/farmacologia , Staphylococcus aureus/efeitos dos fármacos , Staphylococcus aureus/patogenicidade , Trypanosoma cruzi/efeitos dos fármacos , Trypanosoma cruzi/patogenicidade
19.
Int J Mol Sci ; 20(7)2019 Apr 03.
Artigo em Inglês | MEDLINE | ID: mdl-30987173

RESUMO

Fritillariae Thunbergii Bulbus (FTB) has been widely used as an antitussive herb for thousands of years in China. However, FTB's traditional uses, chemical compounds and pharmacological activities have not been systematically reviewed. This study aimed to review its traditional uses, phytochemistry, pharmacodynamics, pharmacokinetics and toxicity. We searched the Encyclopedia of Traditional Chinese Medicine to explore the historical records which indicate that it acts to clear heat, resolve phlegm, relieve cough, remove toxicity and disperse abscesses and nodules. We searched 11 databases to identify potential phytochemical or pharmacological studies. Characteristics of its chemical constituents, pharmacological effects, pharmacokinetic and toxicity were descriptively summarized. A total of 9706 studies were identified and 83 of them were included. As a result, 134 chemical constituents were identified, including 26 alkaloids, 29 compounds found in essential oils, 13 diterpenoids, two carbohydrates, two sterols, 18 amino acids, six nucleosides, four nucleobases, four fatty acids, three lignans, and 27 elements. Thirteen pharmacological effects of FTB were identified, including anti-cancer, tracheobronchial relaxation, antitussive, expectorant, anti-muscarinic, anti-inflammation, anti-thyroid, regulation of blood rheology, antiulcer, anti-diarrhea, pain suppression, antioxidation and neuroprotection. These pharmacological activities may be mainly attributed to the alkaloids in FTB. Further phytochemical, pharmacological and network pharmacological studies are recommended.


Assuntos
Asteraceae/química , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/farmacocinética , Extratos Vegetais/farmacologia , Extratos Vegetais/farmacocinética , Testes de Toxicidade , Animais , Humanos , Compostos Fitoquímicos/química , Compostos Fitoquímicos/toxicidade , Extratos Vegetais/química , Extratos Vegetais/toxicidade
20.
Molecules ; 24(8)2019 Apr 22.
Artigo em Inglês | MEDLINE | ID: mdl-31013652

RESUMO

A considerable amount of bioactive compounds have been used for the biopharmaceutical engineering to help human health and nutrition. Hairy root culture (HRC) or transgenic root is a favourable alternative technique for phytochemical production. Ligularia fischeri is a significant source of pharmaceutically important active compounds with an enormous range of health care applications. HRC of L. fischeri was developed using Agrobacterium rhizogenes for the production of polyphenolic compounds with antioxidant, antimicrobial, antidiabetic, anticancer and anti-inflammatory pharmaceutical activities. Hairy roots (HRs) were selected by morphological assessment, genetic and molecular analyses. The maximum accumulation of fresh mass (94.15 g/L) and dry mass (9.45 g/L) was recorded in MS liquid medium supplemented with 30 g/L sucrose at 28 days. Furthermore, HRs successfully produced numerous polyphenolic compounds, including six hydroxycinnamic acids, seven flavonols, seven hydroxybenzoic acids, vanillin, resveratrol, pyrogallol, homogentisic, and veratric acids, which were identified by UHPLC analysis. HRs produced higher total phenolic (185.65 mg/g), and flavonoid (5.25 mg/g) contents than non-transformed roots (125.55 mg/g and 3.75 mg/g). As a result of these metabolic changes, pharmaceutical activities were found higher in HRs than non-transformed roots (NTRs). The present study indicates that HRC has the potential to increase the content of beneficial polyphenolic compounds with higher potential pharmaceutical activities. To the best of our knowledge, the present study is the first report on enhancing the production of polyphenolic compounds with pharmaceutical activities from the HRCs of L. fischeri.


Assuntos
Asteraceae , Flavonoides , Fenóis/farmacologia , Raízes de Plantas , Asteraceae/química , Asteraceae/genética , Asteraceae/metabolismo , Avaliação Pré-Clínica de Medicamentos , Flavonoides/biossíntese , Flavonoides/química , Flavonoides/farmacologia , Humanos , Células MCF-7 , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Plantas Geneticamente Modificadas/química , Plantas Geneticamente Modificadas/genética , Plantas Geneticamente Modificadas/metabolismo
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