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1.
Nutrients ; 11(7)2019 Jul 01.
Artigo em Inglês | MEDLINE | ID: mdl-31266155

RESUMO

Consumption of dietary bioactives is an avenue to enhancing the effective healthiness of diets by attenuating the glycaemic response. The intestinal brush border enzyme sucrase-isomaltase (SI) is the sole enzyme hydrolysing consumed sucrose, and we previously showed the acute effects of olive leaf extract (OLE) on sucrase activity when given together with sugars both in vitro and in vivo. Here we tested whether OLE could affect sucrase expression when pre-incubated chronically, a "priming" effect not dependent on competitive interaction with SI, in both a cell model and a human intervention. Using differentiated Caco-2/TC7 cells, long-term pre-treatment with oleuropein-rich olive leaf extract (OLE) lowered SI mRNA, surface protein and activity, and attenuated subsequent sucrose hydrolysis. Based on these results, a randomised, double-blinded, placebo-controlled, crossover pilot study was conducted. OLE (50 mg oleuropein) was consumed in capsule form 3 times a day for 1 week by 11 healthy young women followed by an oral sucrose tolerance test in the absence of OLE. However this treatment, compared to placebo, did not induce a change in post-prandial blood glucose maximum concentration (Glcmax), time to reach Glcmax and incremental area under the curve. These results indicate that changes in SI mRNA, protein and activity in an intestinal cell model by OLE are not sufficient under these conditions to induce a functional effect in vivo in healthy volunteers.


Assuntos
Glicemia/metabolismo , Sacarose na Dieta/metabolismo , Mucosa Intestinal/efeitos dos fármacos , Iridoides/administração & dosagem , Olea , Extratos Vegetais/administração & dosagem , Folhas de Planta , Complexo Sacarase-Isomaltase/metabolismo , Adolescente , Adulto , Idoso , Biomarcadores/sangue , Células CACO-2 , Estudos Cross-Over , Método Duplo-Cego , Feminino , Regulação da Expressão Gênica , Humanos , Mucosa Intestinal/enzimologia , Iridoides/isolamento & purificação , Pessoa de Meia-Idade , Olea/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Período Pós-Prandial , Complexo Sacarase-Isomaltase/genética , Fatores de Tempo , Resultado do Tratamento , Adulto Jovem
2.
Food Chem ; 293: 161-168, 2019 Sep 30.
Artigo em Inglês | MEDLINE | ID: mdl-31151597

RESUMO

Olive leaves have become a promising source of phenolic compounds and flavonoids with high added value. Phenolic compounds and flavonoids are important sources of antioxidants and bioactives, and one of the processes used to effectively produce them is extraction via solvents, using aqueous ethanol solutions. To obtain the highest extraction yield per kg of biomass, olive leaves were extracted using a conventional technique (dynamic maceration) and an emerging technology, such as pressurized liquid extraction. Studies of the factors that influence these processes were performed: temperature, leaf moisture content, solvent/solid, and aqueous ethanol concentration were optimized using the central composite and Box-Behnken experiment designs. Pressurized liquid extraction resulted in more efficient oleuropein and luteolin-7-O-glucoside extraction than dynamic maceration. The operational conditions for maximizing the recovery of phenolic compounds and flavonoids and antioxidant capacity were determined to be 190 °C, leaf moisture content of 5%, and aqueous ethanol concentration of 80%.


Assuntos
Flavonas/química , Glucosídeos/química , Iridoides/química , Olea/química , Antioxidantes/química , Cromatografia Líquida de Alta Pressão , Flavonas/isolamento & purificação , Flavonoides , Glucosídeos/isolamento & purificação , Iridoides/isolamento & purificação , Olea/metabolismo , Fenóis/química , Extratos Vegetais/química , Folhas de Planta/química , Folhas de Planta/metabolismo , Solventes/química , Temperatura Ambiente
3.
J Asian Nat Prod Res ; 21(8): 727-734, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31179735

RESUMO

Five new iridoids (1-5), jiohenrins A-E, together with sixteen known compounds (6-21), were isolated from the whole plants of Rehmannia henryi. The structures of these compounds were elucidated on the basis of their spectroscopic data.


Assuntos
Iridoides/isolamento & purificação , Rehmannia/química , Linhagem Celular Tumoral , Humanos , Iridoides/química , Iridoides/farmacologia , Imagem por Ressonância Magnética
4.
Fitoterapia ; 135: 99-106, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-31051193

RESUMO

Iridoid-monoterpenoid indole alkaloid hybrids (IMIAHs) represent a rare class of natural products reported from only several plants of Rubiaceae and Dipsacaceae families, while their structural assignments remain a very challenging work due to complexity and flexibility. In the current study, a new IMIAH (1) was isolated from the roots of Dipsacus asper and its structure with absolute configuration was unambiguously established by a combination of spectroscopic analyses, chemical degradation and ECD calculation. A new oleanane-type triterpenoid saponin (2) and 15 known co-metabolites were also obtained and structurally characterized. Our biological evaluations showed that compound 2 exhibited moderate inhibition against acetylcholine esterase (AChE) with an IC50 value of 15.8 ±â€¯0.56 µM, and compound 15 displayed potent cytotoxicity selectively against human A549 and H157 lung cancer cells with IC50 values of 6.94 ±â€¯0.24 and 9.06 ±â€¯0.12 µM, respectively.


Assuntos
Glucosídeos/farmacologia , Iridoides/farmacologia , Ácido Oleanólico/análogos & derivados , Alcaloides de Triptamina e Secologanina/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Dipsacaceae/química , Glucosídeos/química , Glucosídeos/isolamento & purificação , Humanos , Iridoides/química , Iridoides/isolamento & purificação , Estrutura Molecular , Ácido Oleanólico/química , Ácido Oleanólico/isolamento & purificação , Ácido Oleanólico/farmacologia , Raízes de Plantas/química , Alcaloides de Triptamina e Secologanina/química , Alcaloides de Triptamina e Secologanina/isolamento & purificação
5.
Molecules ; 24(8)2019 Apr 23.
Artigo em Inglês | MEDLINE | ID: mdl-31018502

RESUMO

Several Ajuga species are used in Romanian folk medicine for their antioxidant, antimicrobial and anti-inflammatory properties, to treat pain, fever or arthritis. Still, the active compounds responsible for these effects and their mechanism of action are scarcely known. This research was designed to investigate the phytochemical profile (e.g. iridoids, polyphenolic compounds, phytosterols), as well as the biological potential (antioxidant, antibacterial, antifungal, anti-inflammatory properties) of two selected Ajuga species collected from different regions of Romanian spontaneous flora. The main compounds identified in A. reptans aerial parts extracts were 8-O-acetylharpagide, isoquercitrin and ß-sitosterol, whilst in A. genevensis were 8-O-acetylharpagide, luteolin and campesterol. The extracts were screened for their antioxidant potential using different methods (DPPH, TEAC, EPR) and the results showed a good activity, in accordance with the polyphenol content (18-26 mg GAE/g dw). The antifungal activity on the tested strains was good. The determination of few parameters linked with the inflammatory mechanism allowed the assessment of in vivo anti-inflammatory potential. Ajuga reptans and A. genevensis ethanol extracts had anti-inflammatory activity through lowering the oxidative stress, phagocytosis, PMN and total leukocytes. The best anti-oxidative and anti-inflammatory activity was observed for the Ajuga reptans 100 mg dw/mL extract when compared with diclofenac, thus the dose could be correlated with the pharmacological effect. These findings provide substantial evidence that both selected Ajuga species have the potential to be valued as sources of phytochemicals in effective anti-inflammatory herbal preparations.


Assuntos
Ajuga/química , Iridoides/farmacologia , Fitosteróis/farmacologia , Fitoterapia/métodos , Polifenóis/farmacologia , Animais , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Fungos/efeitos dos fármacos , Fungos/crescimento & desenvolvimento , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Negativas/crescimento & desenvolvimento , Bactérias Gram-Positivas/efeitos dos fármacos , Bactérias Gram-Positivas/crescimento & desenvolvimento , Humanos , Inflamação/tratamento farmacológico , Iridoides/química , Iridoides/isolamento & purificação , Testes de Sensibilidade Microbiana , Neutrófilos/efeitos dos fármacos , Estresse Oxidativo/efeitos dos fármacos , Fagocitose/efeitos dos fármacos , Fitosteróis/química , Fitosteróis/isolamento & purificação , Picratos/antagonistas & inibidores , Componentes Aéreos da Planta/química , Extratos Vegetais/química , Plantas Medicinais , Polifenóis/química , Polifenóis/isolamento & purificação , Ratos , Ratos Wistar , Romênia
6.
Planta Med ; 85(11-12): 1034-1039, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-30965376

RESUMO

In this paper, the isolation of one new iridoid glucoside, 6ß-acetoxyipolamiide (1: ), and thirteen (2:  - 14: ) known congeners from two Lamiaceae species, Stachys ocymastrum and Premna resinosa, leaf extracts is reported. The structural determination of the isolated compounds was performed by mono- and bidimensional NMR spectroscopic analysis as well as MS experiments. The isolates were assayed for their antiangiogenic activity by two in vivo models, zebrafish embryos and chick chorioallantoic membrane assays. The compounds with a significant antiangiogenic activity in both assays were ß-hydroxyipolamiide (2: ), ipolamiide (3: ), and buddlejoside A5 (8: ). 6-O-α-l-(3″-O-p-Methoxycinnamoyl-4″-O-acetyl)rhamnopyranosyl catalpol (13: ) and 6-O-α-l-(2″-trans-caffeoyl)rhamnopyranosyl catalpol (6: ) showed the best antiangiogenic response on blood vessel growth in zebrafish embryos, whereas saccatoside (10: ) and 6-O-α-l-(2″-O - : p-methoxycinnamoyl-3″-O-acetyl)rhamnopyranosyl catalpol (14: ) resulted in a strong reduction of capillary formation in the chorioallantoic membrane assay.


Assuntos
Inibidores da Angiogênese/farmacologia , Iridoides/isolamento & purificação , Lamiaceae/química , Stachys/química , Animais , Bioensaio , Embrião de Galinha , Relação Dose-Resposta a Droga , Iridoides/farmacologia , Espectroscopia de Ressonância Magnética , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Folhas de Planta/química , Peixe-Zebra
7.
Food Chem ; 291: 167-179, 2019 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-31006456

RESUMO

The berries from the native Chilean Gaultheria phillyreifolia and G. poeppigii are appreciated for their sweet taste and aroma. Fruits from both species were investigated for their secondary metabolite composition and antioxidant activity. The extracts were submitted to membrane chromatography to separate anthocyanins from copigments. Four anthocyanins were isolated by counter-current chromatography (CCC) and identified as cyanidin galactoside, cyanidin arabinoside, delphinidin galactoside and delphinidin arabinoside. From the copigments, CCC allowed the separation of quercetin(Q)-3-arabinoside, Q-3-rutinoside Q-3-rhamnoside and 3-caffeoylquinic acid. Additionally, the iridoids monotropein-10-trans-coumarate, monotropein-10-trans-cinnamate and 6α-hydroxy-dihydromonotropein-10-trans-cinnamate were isolated. The latter two iridoids are reported here for the first time. Some 34 other compounds were tentatively identified by HPLC-DAD-ESI-MSn. The antioxidant activity showed differences between anthocyanins and copigments from both species. Main compounds were quantified and submitted to a Partial-Least Square Discriminant Analysis (PLS-DA). This is the first report on the isolation of phytochemicals from the selected Chilean Gaultheria species.


Assuntos
Antioxidantes/química , Gaultheria/química , Iridoides/química , Polifenóis/química , Chile , Cromatografia Líquida de Alta Pressão , Distribuição Contracorrente , Análise Discriminante , Frutas/química , Frutas/metabolismo , Gaultheria/metabolismo , Iridoides/isolamento & purificação , Análise dos Mínimos Quadrados , Extratos Vegetais/química , Polifenóis/isolamento & purificação , Espectrometria de Massas por Ionização por Electrospray
8.
Fitoterapia ; 134: 378-381, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30880242

RESUMO

A new iridoid glycoside, named camptoside (1), together with three known compounds as dehydrodiconiferyl alcohol-9'-O-ß-d-glucopyranoside (2), aesculetin (3) and vajicoside (4), have been isolated from Camptosorus sibiricus Rupr. (Aspleniaceae). Their structures were established on the basis of spectroscopic analysis, especially 1D- and 2D-NMR data, and by comparison of their spectroscopic and physical data with those reported in the literature. Compounds 1-3 exhibited inhibitions of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values of 11.2, 8.3 and 9.4 µM, respectively.


Assuntos
Anti-Inflamatórios/farmacologia , Glicosídeos/farmacologia , Iridoides/farmacologia , Macrófagos/efeitos dos fármacos , Traqueófitas/química , Animais , Anti-Inflamatórios/isolamento & purificação , Síndrome de Chilaiditi , Glicosídeos/isolamento & purificação , Iridoides/isolamento & purificação , Camundongos , Estrutura Molecular , Óxido Nítrico/metabolismo , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Células RAW 264.7
9.
J Photochem Photobiol B ; 193: 162-171, 2019 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-30884286

RESUMO

Olive leaves contain higher amount of polyphenols than olive oil and represent a waste product from olive harvest and pruning of olive trees. The most abundant compound in olive leaves is oleuropein. Benefits of the topical application of olive leaves extract were previously reported, but little information is available on its photoprotective potential and the result of the association of this extract with organic UV filters in topical sunscreen formulations. The olive leaves extract photoprotective potential is less explored for both oral and topical photoprotection in comparison with other plants extracts and polyphenols, such as Polypodium leucotomos extract and resveratrol. There are increasing efforts towards developing more efficient sunscreens and a photoprotection assessement along with a better understanding of the photochemistry of naturally occurring sunscreens could aid the design of new and improved commercial sunscreen formulations. This study was designed to investigate the photoprotective potential of olive leaves extract standardized for oleuropein performing a set of in vitro and in silico tools as an innovative approach, highlighting yeast assays, in vitro Sun Protection Factor (SPF) and molecular modelling studies of UV absorption. This study supports the use of olive leaves extract for photoprotection, as an effective photoprotective, anti-mutagenic and antioxidant active, also showing a synergistic effect in association with UV filters with an improvement on in vitro SPF of sunscreen formulations.


Assuntos
Iridoides/química , Olea/química , Extratos Vegetais/química , Protetores Solares/química , Antioxidantes/química , Iridoides/isolamento & purificação , Modelos Moleculares , Olea/metabolismo , Folhas de Planta/química , Folhas de Planta/metabolismo , Teoria Quântica , Fator de Proteção Solar , Protetores Solares/isolamento & purificação , Raios Ultravioleta
10.
Am J Chin Med ; 47(2): 259-300, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-30857406

RESUMO

Eucommia ulmoides Oliver, a single species of Eucommia genus belonging to the Eucommiaceae family, is an endemic in China and has been used in traditional Chinese medicine for nearly two thousand years. Records from different historical periods highlight E. ulmoides and its officinal botanical parts, usefulness in adaptation to disease and its central role in Chinese medicine theory. There are also historical collection documents for minorities in China. Tearing the leaves, bark and fruit produces strands of latex; a description of E. ulmoides's morphological features is recorded in this paper. This review summarizes 204 natural compounds isolated from this plant, which are divided into seven categories: lignans, iridoids, flavonoids, phenols, steroids, terpenes and others. These components possess wide-ranging pharmacological efficacies, such as antihypertensive, antihyperglycemic, antihyperlipidemia, anti-oxidative, anti-osteoporosis, antitumor, immunomodulatory and neuroprotective activities. This review aims to provide a reference for extensive researches of E. ulmoides crude drugs, especially for quality control, biosynthesis and structure modification of active ingredients and pharmacological mechanism.


Assuntos
Eucommiaceae/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Iridoides/isolamento & purificação , Iridoides/farmacologia , Lignanas/isolamento & purificação , Lignanas/farmacologia , Fenóis/isolamento & purificação , Fenóis/farmacologia , Fitosteróis/isolamento & purificação , Fitosteróis/farmacologia , Terpenos/isolamento & purificação , Terpenos/farmacologia , Anti-Hipertensivos , Antineoplásicos Fitogênicos , Antioxidantes , Conservadores da Densidade Óssea , Eucommiaceae/anatomia & histologia , Flavonoides/química , Humanos , Hipoglicemiantes , Hipolipemiantes , Fatores Imunológicos , Iridoides/química , Lignanas/química , Fármacos Neuroprotetores , Fenóis/química , Fitosteróis/química , Fitoterapia , Controle de Qualidade , Terpenos/química
11.
Curr Pharm Biotechnol ; 20(4): 302-308, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-30747062

RESUMO

BACKGROUND: The genus Psychotria and Palicourea are reported as a source of alkaloids and iridoids, which exhibit biological activities. This study aimed to evaluate antiproliferative and anticholinesterase activities and quantification of the alkaloids of seven species among the genus found in Mato Grosso do Sul region in Brazil. METHODS: Concentrations of alkaloids were measured spectrophotometrically. The extracts were submitted to antiproliferative activity against ten cell lines. The anticholinesterase activity of the extracts was developed using brain structures of male Wistar rats: cerebral cortex, hippocampus, hypothalamus and striatum by the Ellman method. RESULTS: Alkaloids from Psychotria and Palicourea species were quantified which showed values of 47.6 to 21.9 µg/g. Regarding the antiproliferative potential, Palicourea crocea demonstrated selectivity against the 786-0 cell line (GI50: 22.87 µg/mL). Psychotria leiocarpa inhibited cell growth against OVCAR-3 (GI50: 3.28 µg/mL), K-562 (GI50: 5.26 µg/mL), HaCaT (GI50: 27.20 µg/mL), PC-3 (GI50: 34.92 µg/mL), MCF-7 (GI50: 35.80 µg/mL) and P. capillacea showed activity against OVCAR-3 (GI50: 2.33 µg/ml) and U251 (GI50: 16.66 µg/ml). The effect of acetylcholinesterase inhibition was more effective in the hippocampus, demonstrating inhibition for Paliourea crocea, Psychotria deflexa, P. brachybotrya and P. leiocarpa of 70%, 57%, 50% and 40%, respectively, followed by P. poeppigiana and P. capillacea, inhibiting 21%, compared to the control. CONCLUSION: Herein, the present work showed for the first time, anticholinesterasic and antiproliferative activities of extracts of Palicourea and Psychotria seem to be mainly associated with the levels of alkaloids in the leaves of these species.


Assuntos
Alcaloides/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Inibidores da Colinesterase/farmacologia , Iridoides/farmacologia , Extratos Vegetais/farmacologia , Rubiaceae/química , Alcaloides/isolamento & purificação , Animais , Antineoplásicos Fitogênicos/isolamento & purificação , Brasil , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Inibidores da Colinesterase/isolamento & purificação , Hipocampo/efeitos dos fármacos , Hipocampo/enzimologia , Humanos , Iridoides/isolamento & purificação , Masculino , Extratos Vegetais/isolamento & purificação , Folhas de Planta/química , Ratos , Ratos Wistar , Rubiaceae/crescimento & desenvolvimento , Especificidade da Espécie
12.
Molecules ; 24(3)2019 Feb 11.
Artigo em Inglês | MEDLINE | ID: mdl-30754635

RESUMO

Three previously undescribed iridoids, cornusfurals A⁻C, were isolated from the ethanolic extracts of fruits of Cornus officinalis. Their structures were elucidated by spectroscopic methods, including one-dimensional and two-dimensional nuclear magnetic resonance, ultraviolet spectroscopy, infrared spectroscopy, and mass spectrometry. The neuroprotective activity was evaluated by measuring corticosterone-induced damage in PC12 cells. The results showed that cornusfural B decreased corticosterone-induced PC12 cell damage compared with that in model cells.


Assuntos
Cornus/química , Corticosterona/efeitos adversos , Iridoides/isolamento & purificação , Iridoides/farmacologia , Neurônios/citologia , Animais , Etanol/química , Etanol/isolamento & purificação , Frutas/química , Iridoides/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Neurônios/efeitos dos fármacos , Neuroproteção , Células PC12 , Extratos Vegetais/química , Ratos , Espectrofotometria Infravermelho
13.
Chem Biodivers ; 16(5): e1800474, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30801931

RESUMO

Twelve 3,8-epoxy iridoids, including four new compounds, jatamanins R-U (1-4), and eight known compounds (5-12), were obtained from the roots and rhizomes of Valeriana jatamansi. The structures were elucidated from analysis of spectroscopic data. The absolute configurations of 1-4 were determined by comparison of experimental and literature ECD spectra. Moreover, the compounds were evaluated for cytotoxic effects against glioma stem cells, inhibition of NO production, activity against influenza A virus and reversal of multidrug resistance of HepG2/ADR cells. Compounds 9 and 12 showed significant cytotoxic potency against GSC-18# (IC50 =1.351 and 4.439 µg ml-1 , respectively) and GSC-3# (IC50 =10.88 and 6.348 µg ml-1 , respectively) glioma stem cells, while compound 12 was also slightly less potent against GSC-12# (IC50 =13.45 µg ml-1 ) glioma stem cell growth. In addition, compounds 9 and 12 displayed obvious inhibition of NO production (IC50 =4.6 and 15.8 µm, respectively).


Assuntos
Iridoides/química , Valeriana/química , Animais , Proliferação de Células/efeitos dos fármacos , Dicroísmo Circular , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Células Hep G2 , Humanos , Iridoides/isolamento & purificação , Iridoides/farmacologia , Lipopolissacarídeos/toxicidade , Macrófagos/citologia , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Espectroscopia de Ressonância Magnética , Camundongos , Conformação Molecular , Óxido Nítrico/metabolismo , Raízes de Plantas/química , Raízes de Plantas/metabolismo , Células RAW 264.7 , Relação Estrutura-Atividade , Valeriana/metabolismo
14.
J Biol Chem ; 294(11): 4215-4232, 2019 03 15.
Artigo em Inglês | MEDLINE | ID: mdl-30655291

RESUMO

Aggregation of α-synuclein (αSN) is implicated in neuronal degeneration in Parkinson's disease and has prompted searches for natural compounds inhibiting αSN aggregation and reducing its tendency to form toxic oligomers. Oil from the olive tree (Olea europaea L.) represents the main source of fat in the Mediterranean diet and contains variable levels of phenolic compounds, many structurally related to the compound oleuropein. Here, using αSN aggregation, fibrillation, size-exclusion chromatography-multiangle light scattering (SEC-MALS)-based assays, and toxicity assays, we systematically screened the fruit extracts of 15 different olive varieties to identify compounds that can inhibit αSN aggregation and oligomer toxicity and also have antioxidant activity. Polyphenol composition differed markedly among varieties. The variety with the most effective antioxidant and aggregation activities, Koroneiki, combined strong inhibition of αSN fibril nucleation and elongation with strong disaggregation activity on preformed fibrils and prevented the formation of toxic αSN oligomers. Fractionation of the Koroneiki extract identified oleuropein aglycone, hydroxyl oleuropein aglycone, and oleuropein as key compounds responsible for the differences in inhibition across the extracts. These phenolic compounds inhibited αSN amyloidogenesis by directing αSN monomers into small αSN oligomers with lower toxicity, thereby suppressing the subsequent fibril growth phase. Our results highlight the molecular consequences of differences in the level of effective phenolic compounds in different olive varieties, insights that have implications for long-term human health.


Assuntos
Frutas/química , Iridoides/farmacologia , Olea/química , alfa-Sinucleína/antagonistas & inibidores , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cromatografia em Gel , Relação Dose-Resposta a Droga , Humanos , Iridoides/química , Iridoides/isolamento & purificação , Luz , Agregados Proteicos/efeitos dos fármacos , Relação Estrutura-Atividade , alfa-Sinucleína/química , alfa-Sinucleína/metabolismo
15.
Nat Prod Res ; 33(9): 1334-1339, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-29768024

RESUMO

A new coumarin-secoiridoid diglucoside, named Isofraxisecoside, was isolated from the stem bark of Fraxinus xanthoxyloides (G. Don) Wall. ex A. DC. along with nine known compounds. The structure of new compound has been determined on the basis of 1H, 13C, 2D NMR and HRMS methods.


Assuntos
Fraxinus/química , Iridoides/química , Cumarínicos/química , Iridoides/isolamento & purificação , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Casca de Planta/química
16.
Chem Biodivers ; 16(2): e1800524, 2019 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30468024

RESUMO

Three new iridoids, rel-(4aR,7S,7aS)-7-hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carbaldehyde (1), 1-methoxy-7-methyl-1,3,5,6-tetrahydrocyclopenta[c]pyran-4-carbaldehyde (2), and rel-(1R,4S,4aS,7R,7aR)-7-methylhexahydro-1,4-(epoxymethano)cyclopenta[c]pyran-3(1H)-one (3), together with seven known analogues, were isolated from the 95 % EtOH extract of the whole plants of Pedicularis uliginosa Bunge. Their structures were elucidated via extensive NMR spectroscopy and mass spectral data. In terms of inhibitory effects on human tumor cells, compounds 1, 2, 6, 7, and 8 exhibited better inhibitory activities against ACHN cells than the positive control (vinblastine).


Assuntos
Iridoides/isolamento & purificação , Pedicularis/química , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Humanos , Iridoides/química , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Relação Estrutura-Atividade
17.
J Pharm Biomed Anal ; 164: 475-480, 2019 Feb 05.
Artigo em Inglês | MEDLINE | ID: mdl-30472581

RESUMO

A new high performance liquid chromatography (HPLC) method has been established for quantitative and qualitative analysis of three tetracyclic iridoids: ML-2-3 (1), molucidin (2), and ML-F52 (3), which are responsible for anti-trypanosomal and anti-leishmanial activities of Morinda lucida Bentham leaves. Separation of 1-3 from dried 80% aqueous (aq.) ethanol extract was achieved on a reversed-phase cholester column packed with cholesteryl-bonded silica using an acetonitrile-0.1% aq. formic acid mobile phase system. Ultraviolet-visible (UV-VIS) spectroscopy was employed for detection of compounds, and their contents were determined by measuring absorbance at 254 nm. Depending on the above system, several factors potentially affecting the concentration of tetracyclic iridoids were evaluated resulting in several variation on plant organs, seasonality, variation between individual trees, and branch positions within the trees. Moreover, we developed a simple, quick, and effective method for tetracyclic iridoid isolation from M. lucida leaves that consisted of extraction by sonication into 80% aq. ethanol, basic hydrolysis, acid neutralization, liquid-liquid extraction into an organic solvent, and reverse phase open column chromatography. Employing this method, we have succeeded to obtain 1 as a colorless crystal yielding of 0.23%, which was 28 times higher than that of previous isolation method. Setting up methodology in this paper may be important for future in vitro and in vivo studies of tetracyclic iridoids and moreover for their applications in new drug design and development.


Assuntos
Fracionamento Químico/métodos , Iridoides/farmacologia , Morinda/química , Extratos Vegetais/farmacologia , Tripanossomicidas/farmacologia , Fracionamento Químico/instrumentação , Cromatografia Líquida de Alta Pressão/instrumentação , Cromatografia Líquida de Alta Pressão/métodos , Desenho de Drogas , Iridoides/análise , Iridoides/química , Iridoides/isolamento & purificação , Extratos Vegetais/análise , Extratos Vegetais/química , Folhas de Planta/química , Pesquisa Qualitativa , Solventes/química , Tripanossomicidas/análise , Tripanossomicidas/química , Tripanossomicidas/isolamento & purificação , Trypanosoma/efeitos dos fármacos
18.
Chemosphere ; 215: 507-514, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-30340159

RESUMO

In this work, a mesoporous Fe3+ type ion exchanger (DOW-3) was used to adsorb the geniposide (GS) involved in gardenia yellow pigment waste water. To test its viability, the mass transfer zone (MTZ) in dynamic adsorption column that plays an important role in the future scale-up of the GS adsorption process was studied systematically. Simulation of the MTZ behavior under various operation conditions in a packed adsorption column enabled the predictions of breakthrough curves of GS for the mesoporous adsorbent. Several modes of mass transport and processes taking place simultaneously, such as permeation, convection, dispersion and adsorption equilibrium were incorporated in the proposed model. Modeling process firstly affected the behavior of MTZ when it formed and moved throughout the column, and then had a much greater impact on the shape of breakthrough curve in the simulation. The dynamics of MTZ were studied under different adsorption conditions such as various column heights, flow rates and inlet concentrations. Moreover, the post-processing technique and 3D visualization of MTZ simulation results were capable of demonstrating the expanding and progressing of the MTZ related to the adsorption isotherm. The basic findings of MTZ dynamics will be very useful for process scale up. Additionally, the effective molecule docking results obtained from this study, help us fully understand the contribution of various molecular forces in the adsorption mechanism.


Assuntos
Cromatografia por Troca Iônica/instrumentação , Simulação por Computador , Troca Iônica , Iridoides/isolamento & purificação , Purificação da Água/métodos , Adsorção , Compostos Férricos , Modelos Teóricos , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Águas Residuárias/química
19.
J Oleo Sci ; 68(1): 33-43, 2019 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-30542008

RESUMO

Mediterranean olive trees have been cultivated in Pakistan for decades to promote olive cultivation and use of olive oil. The qualitative characteristics of seven mono and one multi-varietal extra virgin olive oils (EVOOs) extracted from Italian cultivars grown in different areas of Balochistan a southwestern province of Pakistan were evaluated. Present study aims to assess the impact of bioclimatological change on biochemical profile of exotic cultivars. The dominating fatty acids found in analyzed EVOOs were oleic (65-72%), linoleic (10.61-18.33%) and palmitic acids (12-16%). The tocopherols α, (ß+γ) and δ contents showed a great diversity which ranged from (60-408) mg/kg while, total phenol concentration ranged from (200-370) mg/kg. The analyses of phenolic compounds revealed the presence of phenolic acids, phenolic alcohols, secoiridoids, flavonoids, oleuropein and verbascosides. One-way ANOVA revealed significant differences (p < 0.05) regarding studied parameters. Principal component analysis (PCA) was applied to identify the main components and to classify samples into groups in terms of fatty acids and phenolic profiles. The first group (Frantoio, Moraiolo, Pendolino, Multi-varietal mixture) characterized by high amount of oleic acid and MUFAs/PUFAs ratio. The second group (Maurino and Leccino) correlates with SFAs and third (Ottobrattica, Coratina) with PUFAs. Based on the PCA of phenolic profile the studied cultivars were divided into two main groups. Morialo, Pendolino and Maurino correlated with (phenolic acids, hydroxytyrosol, flavonoids and secoiridoids). Frantoio, Ottobrattica, Coratina, multi-varietal and Leccino were correlated with oleuropein, tyrosol and ligstroside aglycon. The obtained data was compared with those obtained from same cultivars in their original and/or different growing area. Marked differences were observed in the composition of oleic, linoleic, palmitic acids, secoiridoids and total phenolic contents. These differences could be due to change in geographical location and climatical condition of Balochistan. The cultivar Moraiolo has shown best adaptation and preserved its biochemical composition among all studied cultivars.


Assuntos
Ácidos Graxos/análise , Olea/química , Azeite de Oliva/análise , Fenóis/análise , Tocoferóis/análise , Adaptação Biológica , Mudança Climática , Ácidos Graxos/isolamento & purificação , Flavonoides/análise , Flavonoides/isolamento & purificação , Espécies Introduzidas , Irã (Geográfico) , Iridoides/análise , Iridoides/isolamento & purificação , Itália , Azeite de Oliva/isolamento & purificação , Paquistão , Fenóis/isolamento & purificação , Análise de Componente Principal , Tocoferóis/isolamento & purificação
20.
Nat Prod Res ; 33(1): 53-58, 2019 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-29502450

RESUMO

A new dimeric secoiridoids derivative, named japonicaside E, together with six known compounds were isolated from the flower buds of Lonicera japonica. The structures of these compounds were elucidated by the analyses of mass spectrometry and NMR spectroscopy. All compounds were evaluated for anti-inflammatory activity in vitro.


Assuntos
Iridoides/isolamento & purificação , Lonicera/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Flores/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular
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