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Ocimum is considered the largest genus in the Lamiacea family. The genus includes basil, a group of aromatic plants with a wide range of culinary uses that nowadays draws attention for its medicinal and pharmaceutical potential. This systematic review intends to explore the chemical composition of nonessential oils and their variation across different Ocimum species. Moreover, we aimed to identify the state of knowledge regarding the molecular space in this genus as well as the different methods of extraction/identification and geographical location. Seventy-nine eligible articles were selected for the final analysis, from which we extracted more than 300 molecules. We found that the countries with the highest number of studies into Ocimum species are India, Nigeria, Brazil, and Egypt. However, from all known species of Ocimum, only 12 were found to have an extensive chemical characterization, particularly Ocimum basilicum and Ocimum tenuiflorum. Our study focused especially on alcoholic, hydroalcoholic, and water extracts, in which the main techniques for compound identifications are GC-MS, LC-MS, and LC-UV. Across the compiled molecules, we found a wide variety of compounds, especially flavonoids, phenolic acids, and terpenoids, suggesting that this genus could be a very useful source of possible bioactive compounds. The information collected in this review also emphasizes the huge gap between the vast number of Ocimum species discovered and the number of studies in each of them that determined the chemical characterization.
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The species Bathysa gymnocarpa K.Schum is a tree belonging to the Rubiaceae family, endemic in Brazil. So far, there are reports neither of phytochemical work nor of biological evaluation of it. The analysis by High Performance Liquid Chromatography coupled to a Diode Array Detector and a tandem Mass Spectrometer with an Electrospray Ionization source (HPLC-DAD-ESI-MS/MS) of its crude extract allowed to characterize in a complex mixture, without isolation, fourteen compounds, being two as cinnamic acid derivatives, and the others as mono-, di- and triglycosilated derivatives of the flavonols quercetin and kaempferol. These compounds are reported for the first time in Bathysa spp.
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Liquid chromatography high-resolution mass spectrometry fingerprinting together with pattern recognition techniques was used to determine the metabolites involved in the susceptibility of apple cultivars to rosy apple aphid (RAA). Preprocessing of ultra-high-performance liquid chromatography coupled to electrospray ionization and quadrupole time-of-flight mass spectrometry raw data of resistant and susceptible apple cultivars was carried out with XCMS and CAMERA packages. Univariate statistical tools and multivariate data analysis highlighted significant different profiles of the apple metabolomes according to their tolerance to RAA. Optimized and cross-validated Partial least squares discriminant analysis and orthogonal projections to latent structures discriminant analysis models confirmed trans-4-caffeoylquinic acid and 4-p-coumaroylquinic acid as biomarkers for the identification of resistant and susceptible apple cultivars to RAA and disclosed that only hydroxycinnamic acids are involved in the disease susceptibility of cultivars. In this sense, the final steps of the biosynthesis of caffeoylquinic acid (CQA) and p-coumaroylquinic acid (p-CoQA) become decisive because the isomerization of 5-CQA to 4-CQA is favored in resistant cultivars, whereas the isomerization of 5-p-CoQA to 4-p-CoQA is favored in susceptible cultivars.
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Afídeos , Malus , Syzygium , Animais , Biomarcadores , Cromatografia Líquida de Alta Pressão/métodos , Ácidos Cumáricos , Espectrometria de Massas , MetabolômicaRESUMO
INTRODUCTION: The methanol (MeOH) leaf extracts of the species Faramea bahiensis, F. hyacinthina and F. truncata (Rubiaceae) have previously shown in vitro non-cytotoxic and anti-dengue virus serotype 2 (DENV2) activities in human hepatocarcinoma cell lineage (HepG2). Chemical studies have led to the isolation of major flavonoids, but quite complex fractions of phenolic compounds still remain. OBJECTIVE: To complete the study of phenolic compounds in the leaves and to access the presence of these compounds in the stems of these Faramea spp. by online high-performance liquid chromatography-diode array detector-electrospray ionisation tandem mass spectrometry (HPLC-DAD-ESI-MS/MS), as well as to evaluate the in vitro cytotoxic and anti-DENV2 activities of their MeOH stem extracts. METHODOLOGY: The identification was performed by comparing retention times, UV and mass spectra with those of available standards and by using the mechanisms and fragmentation patterns established in previous studies. The effects of the extracts in DENV2 infected HepG2 cell viability was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. The virus titer was quantified by plaque assay. RESULTS: The study led to the characterisation of 31 phenolic compounds including flavonoid O- and C-glycosides, phenolic acids and one coumarin. The stem extracts from F. hyacinthina and F. bahiensis presented a similar bioactivity to those of their leaves but a loss of cytoprotective activity of F. bahiensis and a higher cytotoxicity of F. truncata were observed. CONCLUSIONS: This research allowed a detailed phenolic composition of three bioactive Faramea species to be achieved, thus contributing to the study of this genus and providing valuable information for further phytotherapeutic applications.
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Antivirais/farmacologia , Cromatografia Líquida de Alta Pressão/métodos , Vírus da Dengue/efeitos dos fármacos , Folhas de Planta/química , Caules de Planta/química , Polifenóis/análise , Polifenóis/farmacologia , Rubiaceae/química , Espectrometria de Massas por Ionização por Electrospray/métodos , Espectrometria de Massas em Tandem/métodos , Animais , Brasil , Linhagem Celular , Sobrevivência Celular/efeitos dos fármacos , Cricetinae , Flavonoides/análise , Flavonoides/farmacologia , Células Hep G2 , Humanos , Sais de Tetrazólio/química , Tiazóis/químicaRESUMO
Lettuce (Lactuca sativa) is one of the most popular leafy vegetables in the world and constitutes a major dietary source of phenolic compounds with health-promoting properties. In particular, the demand for green and red oak-leaf lettuces has considerably increased in the last years but few data on their polyphenol composition are available. Moreover, the usage of analytical edge technology can provide new structural information and allow the identification of unknown polyphenols. In the present study, the phenolic profiles of green and red oak-leaf lettuce cultivars were exhaustively characterized by ultrahigh-performance liquid chromatography (UHPLC) coupled online to diode array detection (DAD), electrospray ionization (ESI), and quadrupole time-of-flight mass spectrometry (QToF/MS), using the MSE instrument acquisition mode for recording simultaneously exact masses of precursor and fragment ions. One hundred fifteen phenolic compounds were identified in the acidified hydromethanolic extract of freeze-dried lettuce leaves. Forty-eight of these compounds were tentatively identified for the first time in lettuce, and only 20 of them have been previously reported in oak-leaf lettuce cultivars in literature. Both oak-leaf lettuce cultivars presented similar phenolic composition, except for apigenin-glucuronide and dihydroxybenzoic acid, only detected in the green cultivar; and for luteolin-hydroxymalonylhexoside, an apigenin conjugate with molecular formula C40 H54 O19 (monoisotopic MW = 838.3259 u), cyanidin-3-O-glucoside, cyanidin-3-O-(3â³-O-malonyl)glucoside, cyanidin-3-O-(6â³-O-malonyl)glucoside, and cyanidin-3-O-(6â³-O-acetyl)glucoside, only found in the red cultivar. The UHPLC-DAD-ESI-QToF/MSE approach demonstrated to be a useful tool for the characterization of phenolic compounds in complex plant matrices.
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Lactuca/química , Fenóis/análise , Folhas de Planta/química , Apigenina/química , Cromatografia Líquida de Alta Pressão/métodos , Glucosídeos/química , Luteolina/química , Estrutura Molecular , Fenóis/química , Extratos Vegetais/química , Espectrometria de Massas por Ionização por ElectrosprayRESUMO
Diverse plants of ethnobotanic interest in Amazonia are commonly used in traditional medicine. We determined the antioxidant potential against lipid peroxidation, the antimicrobial activity, and the polyphenol composition of several Amazonian plants (Brownea rosademonte, Piper glandulosissimum, Piper krukoffii, Piper putumayoense, Solanum grandiflorum, and Vismia baccifera). Extracts from the plant leaf, bark, and stem were prepared as aqueous infusions, as used in folk medicine, and added to rat liver microsomes exposed to iron. The polyphenolic composition was detected by reverse-phase HPLC coupled to diode-array detector and MS/MS analysis. The antimicrobial activity was tested by the spot-on-a-lawn method against several indicator microorganisms. All the extracts inhibited lipid oxidation, except the P. glandulosissimum stem. The plant extracts exhibiting high antioxidant potential (V. baccifera and B. rosademonte) contained high levels of flavanols (particularly, catechin and epicatechin). By contrast, S. grandiflorum leaf, which exhibited very low antioxidant activity, was rich in hydroxycinnamic acids. None of the extracts showed antimicrobial activity. This study demonstrates for the first time the presence of bioactive polyphenolic compounds in several Amazonian plants, and highlights the importance of flavanols as major phenolic contributors to antioxidant activity.