RESUMEN
The study investigated the effects of cultivating Tridax procumbens in hydroponic conditions with different concentrations of copper ions, aiming to understand the physiological changes and the impact on the biosynthesis of secondary metabolites. The treatments consisted of a completely randomized design, with five increasing concentrations of copper (T0 = 0.235, T1 = 12.5, T2 = 25, T3 = 50, T4 = 100 µmol L-1 of Cu), under controlled conditions for 36 days. Analysis of bioactive compounds in leaves was performed by HPLC-DAD and ESI-MS. Several phenolic compounds, alkaloids, phytosterols and triterpenoids were identified, demonstrating the plant's metabolic plasticity. The highest dose of copper (100 µmol L-1) significantly promoted voacangine, the most predominant compound in the analyses. Notably, 66.7% of the metabolites that showed an increase in concentration, were phenolic compounds. Furthermore, treatments with 12.5 and 25 µmol L-1 of copper were identified as promoting the biosynthesis of phytosterols and triterpenoids. These biochemical adaptations can play a fundamental role in the survival and development of plants in environments contaminated by metals, and from this it is possible to determine cultivation techniques that maximize the biosynthesis of the compound of interest.
Asunto(s)
Cobre , Hojas de la Planta/metabolismo , Asteraceae/metabolismo , Fitosteroles/metabolismoRESUMEN
The comparative metabolic profiling and their biological properties of eight extracts obtained from diverse parts (leaves, flowers, roots) of the medicinal plant Flourensia fiebrigii S.F. Blake, a chemotype growing in highland areas (2750â m a.s.l.) of northwest Argentina, were investigated. The extracts were analysed by GC-MS and UHPLC-MS/MS. GC-MS analysis revealed the presence of encecalin (relative content: 24.86 %) in ethereal flower extract (EF) and this benzopyran (5.93 %) together sitosterol (11.35 %) in the bioactive ethereal leaf exudate (ELE). By UHPLC-MS/MS the main compounds identified in both samples were: limocitrin, (22.31 %), (2Z)-4,6-dihydroxy-2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]-1-benzofuran-3-one (21.31 %), isobavachin (14.47 %), naringenin (13.50 %), and sternbin, (12.49 %). Phytocomplexes derived from aerial parts exhibited significant activity against biofilm production of Pseudomonas aeruginosa and Staphylococcus aureus, reaching inhibitions of 74.7-99.9 % with ELE (50â µg/mL). Notably, the extracts did not affect nutraceutical and environmental bacteria, suggesting a selective activity. ELE also showed the highest reactive species scavenging ability. This study provides valuable insights into the potential applications of this chemotype.
Asunto(s)
Asteraceae , Espectrometría de Masas en Tándem , Cromatografía de Gases y Espectrometría de Masas , Extractos Vegetales/farmacología , Extractos Vegetales/metabolismo , Cromatografía Líquida de Alta Presión , Hojas de la Planta/metabolismo , Asteraceae/metabolismoRESUMEN
Metalliferous soils can selectively shape plant species' physiology towards tolerance of high metal concentrations that are usually toxic to organisms. Some adapted plant species tolerate and accumulate metal in their tissues. These metals can serve as an elemental defence but can also decrease growth. Our investigation explored the capacity of natural metal accumulation in a tropical tree species, Eremanthus erythropappus (Asteraceae) and the effects of such bioaccumulation on plant responses to herbivory. Seedlings of E. erythropappus were grown in a glasshouse on soils that represented a metal concentration gradient (Al, Cu, Fe, Mn and Zn), and then the exposed plants were fed to the herbivores in a natural habitat. The effect of herbivory on plant growth was significantly mediated by foliar metal ion concentrations. The results suggest that herbivory effects on these plants change from negative to positive depending on soil metal concentration. Hence, these results provide quantitative evidence for a previously unsuspected interaction between herbivory and metal bioaccumulation on plant growth.
Asunto(s)
Asteraceae/metabolismo , Herbivoria , Metales/metabolismo , Contaminantes del Suelo/metabolismo , Asteraceae/crecimiento & desarrollo , Modelos QuímicosRESUMEN
(1) Background: The COVID-19 pandemic lacks treatments; for this reason, the search for potential compounds against therapeutic targets is still necessary. Bioinformatics tools have allowed the rapid in silico screening of possible new metabolite candidates from natural resources or repurposing known ones. Thus, in this work, we aimed to select phytochemical candidates from Peruvian plants with antiviral potential against three therapeutical targets of SARS-CoV-2. (2) Methods: We applied in silico technics, such as virtual screening, molecular docking, molecular dynamics simulation, and MM/GBSA estimation. (3) Results: Rutin, a compound present in Peruvian native plants, showed affinity against three targets of SARS-CoV-2. The molecular dynamics simulation demonstrated the high stability of receptor-ligand systems during the time of the simulation. Our results showed that the Mpro-Rutin system exhibited higher binding free energy than PLpro-Rutin and N-Rutin systems through MM/GBSA analysis. (4) Conclusions: Our study provides insight on natural metabolites from Peruvian plants with therapeutical potential. We found Rutin as a potential candidate with multiple pharmacological properties against SARS-CoV-2.
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Antivirales/química , Antivirales/farmacología , Fitoquímicos/química , Fitoquímicos/farmacología , Plantas/química , Plantas/metabolismo , Asteraceae/química , Asteraceae/metabolismo , Proteasas 3C de Coronavirus/antagonistas & inhibidores , Proteasas 3C de Coronavirus/química , Proteínas de la Nucleocápside de Coronavirus/antagonistas & inhibidores , Proteínas de la Nucleocápside de Coronavirus/química , Proteasas Similares a la Papaína de Coronavirus/antagonistas & inhibidores , Proteasas Similares a la Papaína de Coronavirus/química , Bases de Datos Factuales , Humanos , Lepidium/química , Lepidium/metabolismo , Ligandos , Simulación del Acoplamiento Molecular , Simulación de Dinámica Molecular , Perú , Fosfoproteínas/antagonistas & inhibidores , Fosfoproteínas/química , Rutina/química , Rutina/farmacología , SARS-CoV-2RESUMEN
A need exists for further research elucidating the benefits of environmentally safe photoprotective agents against ultraviolet (UV) exposure, and plant extracts represent a human-friendly alternative formulation. This study was designed to evaluate the potential use of Bellis perennis extract (BPE), from the Asteraceae family, known as the common daisy or the English daisy, in cosmeceuticals as a photoprotective factor, using an in vitro model of UVA-induced keratinocyte damage. Human skin keratinocytes (HaCaT cell line) were incubated with BPE at 0.01, 0.1, or 1% in Dulbecco's Modified Eagle Medium (DMEM), and after 15 min they were submitted to UVA radiation at 5, 10, and 15 J/cm2 doses, respectively. For comparative purposes, Polypodium leucotomos extract (PLE), known as the fern, was used as a positive control in assessing the photoprotective effect. After 24 h of UVA exposure, cell viability (MTT and LDH assays), levels of cleaved caspase-3, cyclooxygenase-2, IL-6, reactive oxygen species (ROS) and antioxidant enzyme (catalase, SOD, and glutathione peroxidase) activity were determined. UVA radiation at 5, 10, and 15 J/cm2 doses reduced cell viability to 63%, 43%, and 23%, respectively; we selected 10 J/cm2 for our purposes. After 24 h of UVA exposure, treatment with 1% BPE and 1% PLE significantly recovered cell viability (p < 0.05). Furthermore, treatment was associated with lower cleaved caspase-3 and ROS levels, higher catalase activity, and lower IL-6 levels in the treated UVA keratinocytes compared with the untreated UVA group (p < 0.01). Our results demonstrate photoprotective and immunomodulatory effects of BPE in skin keratinocytes and support its use as a bioactive agent in cosmetic formulations to prevent skin damage caused by exposure to the UV light.
Asunto(s)
Asteraceae/química , Inmunomodulación/efectos de los fármacos , Extractos Vegetales/farmacología , Protectores contra Radiación/farmacología , Rayos Ultravioleta , Asteraceae/metabolismo , Caspasa 3/metabolismo , Catalasa/metabolismo , Línea Celular , Supervivencia Celular/efectos de los fármacos , Supervivencia Celular/efectos de la radiación , Humanos , Inmunomodulación/efectos de la radiación , Queratinocitos/citología , Queratinocitos/metabolismo , Extractos Vegetales/química , Protectores contra Radiación/química , Especies Reactivas de Oxígeno/metabolismoRESUMEN
The lupeol detection in callus of Vernonanthura patens (Kunth) H. Rob. leaves is discussed. Leaf segments previously treated with sodium hypochlorite, ethanol, and distilled water were placed in MS basal medium (Murashige and Skoog) for 7 days. Next, callus induction were done in two complemented MS medium for 6 weeks. Then, callus propagation were performed in MS medium supplemented with 1.0 mg/L of benzylaminopurine (BAP) and 0.5 mg/L of 2,4-dichlorophenoxyacetic acid (2,4-D) for 50 days. Fresh callus were extracted every 10 days in an ultrasonic bath using ethyl acetate (1.0 g/10 mL). The identification was carried out by Gas Chromatography-Mass Spectrometry (GC-MS) using selected ion monitoring (SIM) acquisition mode with characteristic ions of lupeol. The results obtained indicate the occurrence of lupeol in callus extract after twenty days of proliferation. These findings could be use in subsequent scale-up studies for biomass production containing this active compound in order to replace conventional methods.
Asunto(s)
Asteraceae/citología , Asteraceae/metabolismo , Triterpenos Pentacíclicos/análisis , Triterpenos Pentacíclicos/metabolismo , Hojas de la Planta/citología , Ácido 2,4-Diclorofenoxiacético/farmacología , Compuestos de Bencilo/farmacología , Medios de Cultivo/química , Medios de Cultivo/farmacología , Cromatografía de Gases y Espectrometría de Masas , Hojas de la Planta/metabolismo , Purinas/farmacología , Técnicas de Cultivo de Tejidos/métodosRESUMEN
Smallanthus sonchifolius, also known as yacón, is an Andean crop species commercialized for its nutraceutical and medicinal properties. The tuberous roots of yacón accumulate a diverse array of probiotic and bioactive metabolites including fructooligosaccharides and caffeic acid esters. However, the metabolic diversity of yacón remains unexplored, including the site of biosynthesis and accumulation of key metabolite classes. We report herein a multidisciplinary approach involving metabolomics, gene expression and scanning electron microscopy, to provide a comprehensive analysis of the diversity, distribution and spatial regulation of the specialized metabolism in yacón. Our results demonstrate that different metabolic fingerprints and gene expression patterns characterize specific tissues, organs and cultivars of yacón. Manual inspection of mass spectrometry data and molecular networking allowed the tentative identification of 71 metabolites, including undescribed structural analogues of known bioactive compounds. Imaging by scanning electron microscopy revealed the presence of a new type of glandular trichome in yacón bracts, with a distinctive metabolite profile. Furthermore, the high concentration of sesquiterpene lactones in capitate glandular trichomes and the restricted presence of certain flavonoids and caffeic acid esters in underground organs and internal tissues suggests that these metabolites could be involved in protective and ecological functions. This study demonstrates that individual organs and tissues make specific contributions to the highly diverse and specialized metabolome of yacón, which is proving to be a reservoir of previously undescribed molecules of potential significance in human health.
Asunto(s)
Asteraceae/metabolismo , Suplementos Dietéticos/análisis , Regulación de la Expresión Génica de las Plantas , Metaboloma , Fitoquímicos/metabolismo , Extractos Vegetales/metabolismo , Proteínas de Plantas/metabolismo , Asteraceae/genética , Asteraceae/crecimiento & desarrollo , Hojas de la Planta/genética , Hojas de la Planta/crecimiento & desarrollo , Hojas de la Planta/metabolismo , Proteínas de Plantas/genética , Raíces de Plantas/genética , Raíces de Plantas/crecimiento & desarrollo , Raíces de Plantas/metabolismoRESUMEN
Acting as chemical defense or signaling compounds, secondary metabolites (SMs) play an essential role in the evolutionary success of many angiosperm plant families. However, the adaptive advantages that SMs confer, and the influence of environmental and developmental factors on SMs expression, remains poorly understood. A study of taxa endemic to the variable Andean climate, using a metabolomics approach, may provide further insight. By analyzing gene expression patterns and metabolic fingerprints, we report herein the developmental and environmental regulation of the secondary metabolism of Smallanthus sonchifolius (yacón), a medicinal Andean plant. Our results demonstrate a clear developmental stage dependent regulation of the secondary metabolism of yacón leaves wherein the metabolic diversity increases with plant age. However, environmental factors seem to regulate biosynthetic pathways, creating differences in the expression of chemical classes, pointing to an association between transcription levels of relevant genes and the relative amounts of more than 40 different metabolites. This study suggests that the secondary metabolism of yacón is regulated by a complex interplay between environmental factors and developmental stage and provides insight into the regulatory factors and adaptive roles of SMs in Andean taxa.
Asunto(s)
Asteraceae/genética , Asteraceae/metabolismo , Ambiente , Perfilación de la Expresión Génica/métodos , Metabolómica/métodos , Metabolismo Secundario/genética , Asteraceae/crecimiento & desarrollo , Clima , Análisis por Conglomerados , Regulación del Desarrollo de la Expresión Génica , Regulación de la Expresión Génica de las Plantas , Humedad , Luz , Hojas de la Planta/genética , Hojas de la Planta/crecimiento & desarrollo , Hojas de la Planta/metabolismo , Lluvia , TemperaturaRESUMEN
INTRODUCTION: Interesting data about the family Asteraceae as a new source of Leishmania major dihydroorotate dehydrogenase (LmDHODH) inhibitors are presented. This key macromolecular target for parasites causing neglected diseases catalyzes the fourth reaction of the de novo pyrimidine biosynthetic pathway, which takes part in major cell functions, including DNA and RNA biosynthesis. OBJECTIVES: We aimed to (1) determine LmDHODH inhibitor candidates, revealing the type of chemistry underlying such bioactivity, and (2) predict the inhibitory potential of extracts from new untested plant species, classifying them as active or inactive based on their LC-MS based metabolic fingerprints. METHODS: Extracts from 150 species were screened for the inhibition of LmDHODH, and untargeted UHPLC-(ESI)-HRMS metabolomic studies were carried out in combination with in silico approaches. RESULTS: The IC50 values determined for a subset of 59 species ranged from 148 µg mL-1 to 9.4 mg mL-1. Dereplication of the metabolic fingerprints allowed the identification of 48 metabolites. A reliable OPLS-DA model (R2 > 0.9, Q2 > 0.7, RMSECV < 0.3) indicated the inhibitor candidates; nine of these metabolites were identified using data from isolated chemical standards, one of which-4,5-di-O-E-caffeoylquinic acid (IC50 73 µM)-was capable of inhibiting LmDHODH. The predictive OPLS model was also effective, with 60% correct predictions for the test set. CONCLUSION: Our approach was validated for (1) the discovery of LmDHODH inhibitors or interesting starting points for the optimization of new leishmanicides from Asteraceae species and (2) the prediction of extracts from untested species, classifying them as active or inactive.
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Asteraceae/metabolismo , Leishmania major/efectos de los fármacos , Oxidorreductasas actuantes sobre Donantes de Grupo CH-CH/antagonistas & inhibidores , Cromatografía Liquida/métodos , Dihidroorotato Deshidrogenasa , Concentración 50 Inhibidora , Metabolómica/métodos , Oxidorreductasas actuantes sobre Donantes de Grupo CH-CH/metabolismo , Espectrometría de Masas en Tándem/métodosRESUMEN
The phytochemical investigation of Grazielia gaudichaudeana aerial parts yielded 15 compounds, including diterpenes, triterpenes, sterols and flavonoids. With exception to ent-kaurenoic acid diterpenes, the compounds isolated are being described for the first time in this species. Some unusual 1 H-NMR chemical shifts of 18-nor-ent-labdane (7-9) led us carry out a conformational analysis by theoretical calculations in order to support the experimental data. Moreover, due to the limitation of studies focused on pharmacological potential of Grazielia gaudichaudeana, the present study was carried out to investigate the antioxidant, antiproliferative, antiviral, antileishmanial and antimicrobial activities from the extract, fractions and isolated compounds obtained from this species. Ethyl acetate fraction showed significant activity in the antiproliferative assay, with GI50 range of 3.9 to 27.2â µg mL-1 . Dichloromethane fraction, rich in diterpenoids, inhibited all human tumor cell lines tested, and the nor-labdane 7 showed potent cytotoxic activity against glioma and ovary cancer cell lines.
Asunto(s)
Asteraceae/química , Diterpenos/química , Antiinfecciosos/química , Antiinfecciosos/aislamiento & purificación , Antiinfecciosos/farmacología , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/aislamiento & purificación , Antineoplásicos Fitogénicos/farmacología , Antioxidantes/química , Antiprotozoarios/química , Antiprotozoarios/aislamiento & purificación , Antiprotozoarios/farmacología , Asteraceae/metabolismo , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Cristalografía por Rayos X , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Hongos/efectos de los fármacos , Bacterias Gramnegativas/efectos de los fármacos , Bacterias Grampositivas/efectos de los fármacos , Humanos , Leishmania/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Conformación Molecular , Extractos Vegetales/químicaRESUMEN
In the present study, a series of new esters of secochiliolide acid (SA), a diterpene isolated from Nardophyllum bryoides, were synthesized in good yield. All compounds were evaluated for their in vitro antiparasitic properties (on Plasmodium falciparum and Trypanosoma brucei brucei) and cytotoxicity (on WI38, normal mammalian cells). They displayed moderate antitrypanosomal activity with IC50 values between 2.55 and 18.14 µm, with selectivity indices >10, and low antiplasmodial effects with IC50 > 29 µm. The only exception was the n-hexyl ester of SA, which showed a strong and selective antiplasmodial activity (IC50 = 1.99 µm and selectivity index = 117.0). The in vivo antimalarial efficacy of this compound was then assessed according to the 4-day suppressive test of Peters in mice. An intraperitoneal treatment at 50 mg kg-1 day-1 induced a slight parasitaemia reduction by 56% which was statistically significant on day 4 post-infection and an increase in the survival time.
Asunto(s)
Antimaláricos/química , Antiprotozoarios/química , Diterpenos/química , Ésteres/química , Propionatos/química , Antimaláricos/aislamiento & purificación , Antimaláricos/farmacología , Antiprotozoarios/aislamiento & purificación , Antiprotozoarios/farmacología , Asteraceae/química , Asteraceae/metabolismo , Línea Celular , Supervivencia Celular/efectos de los fármacos , Diterpenos/aislamiento & purificación , Diterpenos/farmacología , Humanos , Extractos Vegetales/química , Plasmodium falciparum/efectos de los fármacos , Propionatos/aislamiento & purificación , Propionatos/farmacología , Trypanosoma brucei brucei/efectos de los fármacosRESUMEN
BACKGROUND: Nacobbus aberrans (Tylenchida: Pratylenchidae) is one of the main plant-parasitic nematodes species that affects crops in Mexico, generating substantial economic losses. Traditionally, the control of the nematodes is carried out using chemical products; however, research efforts are presently focused on the search for new methods for the control of this pest. Natural products derived from plants are an alternative for the control of populations of plant-parasitic nematodes. The genus Heterotheca (Asteraceae) is characterized by containing sesquiterpenes with cadinane skeleton, and some species of this genus exert nematicidal activity. RESULTS: We determined the effects of selected Heterotheca inuloides plant metabolites and some semisynthetic derivatives on the hatching of eggs isolated from the gelatinous matrix and infective second-stage juveniles (J2) of the false root-knot nematode N. aberrans using an in vitro experimental model. Among the evaluated compounds, nematodes were more susceptible to hydroxylated and quinone compounds, whereas the remaining compounds showed moderate or no activity. The presence of the hydroxyl group is essential for nematicidal potential, with changes at the hydroxyl group modifying the nematicidal activity. CONCLUSION: Flowers of Heterotheca inuloides contain bioactive compounds that showed nematicidal activity against N. aberrans. Here we report the nematicidal activities of cadinenes isolated from the flowers of H. inuloides and their semisynthetic derivatives against the false root-knot nematode N. aberrans. © 2018 Society of Chemical Industry.
Asunto(s)
Antinematodos/toxicidad , Asteraceae/metabolismo , Asteraceae/parasitología , Productos Biológicos/toxicidad , Sesquiterpenos/toxicidad , Tylenchida/efectos de los fármacos , Animales , Antinematodos/metabolismo , Productos Biológicos/metabolismo , Flores/metabolismo , Oviposición/efectos de los fármacos , Tylenchida/crecimiento & desarrollo , Tylenchida/fisiologíaRESUMEN
The present study analyzed the effects of different concentrations of Acmella oleracea crude ethanolic extract (EEAO) on the development of germ cells from semi-engorged Amblyomma cajennense females in order to evaluate the potential of this natural chemical as a strategy to control these important ectoparasites. A hundred semi-engorged females were divided into five groups (duplicates) (10 animals/group): Control 1 (distilled water); Control 2 (solvent ethanol 50% and DMSO 1%); and Treatment I to III (3.1, 6.2, and 12.5 mg/mL of EEAO, respectively). For the exposure of the ticks to the extract was used the Adult Immersion Test. After the exposition, the ovaries were removed and submitted to histological analysis using Harris hematoxylin and aqueous eosin. The histochemical tests were performed using PAS and Bromophenol blue staining techniques, for the detection of total polysaccharides and total protein, respectively. The extract caused significant alterations in the oocytes, including changes in the shape of the cells, disorganization, and cytoplasmic vacuolation, decrease in the number of yolk granules and germ vesicle fragmentation. These alterations were more intense in the oocytes in initial developmental stages (I and II). The results obtained in this study confirm the cytotoxic potential of the ethanolic extract of A. oleracea on the germ cells of A. cajennense females, opening up the possibility to use this extract as an alternative to control these ectoparasites.
Asunto(s)
Asteraceae/metabolismo , Gametogénesis/efectos de los fármacos , Ixodidae/efectos de los fármacos , Extractos Vegetales/farmacología , Animales , Femenino , Oocitos/crecimiento & desarrollo , Ovario/citologíaRESUMEN
The ability of leaves to absorb fog water can positively contribute to the water and carbon balance of plants in montane ecosystems, especially in periods of soil water deficit. However, the ecophysiological traits and mechanisms responsible for variations in the speed and total water absorption capacity of leaves are still poorly known. This study investigated leaf anatomical attributes of seven species occurring in seasonal tropical high-altitude ecosystems (rocky outcrop and forest), which could explain differences in leaf water uptake (LWU) capacities. We tested the hypothesis that different sets of anatomical leaf attributes will be more marked in plant individuals living under these contrasting environmental conditions. Anatomical variations will affect the initial rate of water absorption and the total storage capacity, resulting in different strategies for using the water supplied by fog events. Water absorption by leaves was inferred indirectly, based on leaf anatomical structure and visual observation of the main access routes (using an apoplastic marker), the diffusion of water through the cuticle, and non-glandular or glandular trichomes in all species. The results suggest that three LWU strategies coexist in the species studied. The different anatomical patterns influenced the speed and maximum LWU capacity. The three LWU strategies can provide different adaptive advantages to adjust to temporal and spatial variations of water availability in these tropical high-altitude environments.
Asunto(s)
Hojas de la Planta/anatomía & histología , Agua/metabolismo , Altitud , Asteraceae/anatomía & histología , Asteraceae/metabolismo , Ecosistema , Fabaceae/anatomía & histología , Fabaceae/metabolismo , Fluorescencia , Malpighiaceae/anatomía & histología , Malpighiaceae/metabolismo , Melastomataceae/anatomía & histología , Melastomataceae/metabolismo , Myrtaceae/anatomía & histología , Myrtaceae/metabolismo , Ochnaceae/anatomía & histología , Ochnaceae/metabolismo , Hojas de la Planta/metabolismoRESUMEN
The distribution and ultrastructure of capitate glandular trichomes (GTs) in Flourensia species (Asteraceae) have been recently elucidated, but their metabolic activity and potential biological function remain unexplored. Selective nonvolatile metabolites from isolated GTs were strikingly similar to those found on leaf surfaces. The phytotoxic allelochemical sesquiterpene (-)-hamanasic acid A ((-)-HAA) was the major constituent (ca. 40%) in GTs. Although GTs are quaternary ammonium compounds (QACs)-accumulating species, glycine betaine was not found in GTs; it was only present in the leaf mesophyll. Two (-)-HAA accompanying surface secreted products: compounds 4-hydroxyacetophenone (piceol; 1) and 2-hydroxy-5-methoxyacetophenone (2), which were isolated and fully characterized (GC/MS, NMR), were present in the volatiles found in GTs. The essential oils of fresh leaves revealed ca. 33% monoterpenes, 26% hydrocarbon- and 30% oxygenated sesquiterpenes, most of them related to cadinene and bisabolene derivatives. Present results suggest a main role of GTs in determining the volatile and nonvolatile composition of F. campestris leaves. Based on the known activities of the compounds identified, it can be suggested that GTs in F. campestris would play key ecological functions in plant-pathogen and plant-plant interactions. In addition, the strikingly high contribution of compounds derived from cadinene and bisabolene pathways, highlights the potential of this species as a source of high-valued bioproducts.
Asunto(s)
Asteraceae/química , Aceites Volátiles/química , Tricomas/química , Asteraceae/metabolismo , Estructura Molecular , Aceites Volátiles/aislamiento & purificación , Aceites Volátiles/metabolismo , Hojas de la Planta/química , Hojas de la Planta/metabolismo , Tricomas/metabolismoRESUMEN
Members of the subtribe Lychnophorinae occur mostly within the Cerrado domain of the Brazilian Central Plateau. The relationships between its 11 genera, as well as between Lychnophorinae and other subtribes belonging to the tribe Vernonieae, have recently been investigated upon a phylogeny based on molecular and morphological data. We report the use of a comprehensive untargeted metabolomics approach, combining HPLC-MS and GC-MS data, followed by multivariate analyses aiming to assess the congruence between metabolomics data and the phylogenetic hypothesis, as well as its potential as a chemotaxonomic tool. We analyzed 78 species by UHPLC-MS and GC-MS in both positive and negative ionization modes. The metabolic profiles obtained for these species were treated in MetAlign and in MSClust and the matrices generated were used in SIMCA for hierarchical cluster analyses, principal component analyses and orthogonal partial least square discriminant analysis. The results showed that metabolomic analyses are mostly congruent with the phylogenetic hypothesis especially at lower taxonomic levels (Lychnophora or Eremanthus). Our results confirm that data generated using metabolomics provide evidence for chemotaxonomical studies, especially for phylogenetic inference of the Lychnophorinae subtribe and insight into the evolution of the secondary metabolites of this group.
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Asteraceae/metabolismo , Metabolómica , Filogenia , Asteraceae/clasificación , Cromatografía Líquida de Alta Presión , Análisis por Conglomerados , Cromatografía de Gases y Espectrometría de Masas , Espectrometría de Masas , Análisis Multivariante , Análisis de Componente PrincipalAsunto(s)
Asteraceae/química , Glicósidos/química , Fenoles/química , Espectrometría de Masa por Ionización de Electrospray/métodos , Espectrometría de Masas en Tándem/métodos , Asteraceae/metabolismo , Glicosilación , Espectroscopía de Resonancia Magnética , Estructura Molecular , Extractos Vegetales/química , Hojas de la PlantaRESUMEN
The páramo ecosystem has the highest rate of diversification across plant lineages on earth, of which the genus Espeletia (Asteraceae) is a prime example. The current distribution and molecular phylogeny of Espeletia suggest the influence of Andean geography and past climatic fluctuations on the diversification of this genus. However, molecular markers have failed to reveal subtle biogeographical trends in Espeletia diversification, and metabolomic evidence for allopatric segregation in plants has never been reported. Here, we present for the first time a metabolomics approach based on liquid chromatography-mass spectrometry for revealing subtle biogeographical trends in Espeletia diversification. We demonstrate that Espeletia lineages can be distinguished by means of different metabolic fingerprints correlated to the country of origin on a global scale and to the páramo massif on a regional scale. Distinctive patterns in the accumulation of secondary metabolites according to the main diversification centers of Espeletia are also identified and a comprehensive phytochemical characterization is reported. These findings demonstrate that a variation in the metabolic fingerprints of Espeletia lineages followed the biogeography of this genus, suggesting that our untargeted metabolomics approach can be potentially used as a model to understand the biogeographic history of additional plant groups in the páramo ecosystem.
Asunto(s)
Asteraceae/metabolismo , Metaboloma , Metabolómica , Fitoquímicos/metabolismo , Adaptación Biológica , Asteraceae/química , Cromatografía Líquida de Alta Presión , Cromatografía Liquida , Ambiente , Geografía , Metabolómica/métodos , Fitoquímicos/química , Luz Solar , Espectrometría de Masas en TándemRESUMEN
While many redox enzymes are nowadays available for synthetic applications, the toolbox of ene-reductases is still limited. Consequently, the screening for these enzymes from diverse sources in the search of new biocatalyst suitable for green chemistry approaches is needed. Among 13 plant tissue cultures, Medicago sativa and Tessaria absinthioides calli, as well as Capsicum annuum hairy roots, were selected due to their ability to hydrogenate the CC double bond of the model substrate 2-cyclohexene-1-one. The three axenic plant cultures showed more preference toward highly activated molecules such as nitrostyrene and maleimide rather than the classical substrates of the well-known Old Yellow Enzymes, resembling the skills of the NAD(P)H-dependent flavin-independent enzymes. When the three biocatalytic systems were applied in the reduction of chalcones, T. absinthioides showed high chemoselectivity toward the CC double bond whereas the other two demonstrated abilities to biohydrogenate the CC double bounds and the carbonyl groups in a sequential fashion.
Asunto(s)
Asteraceae/metabolismo , Capsicum/metabolismo , Chalconas/metabolismo , Medicago sativa/metabolismo , Oxidorreductasas/metabolismo , Proteínas de Plantas/metabolismo , Biocatálisis , Técnicas de Cultivo , Hidrogenación , Raíces de Plantas/metabolismoRESUMEN
This project analyses the uptake and biodegradation of the antimicrobial sulfadimidine (SDI) from the culture medium and up to the anaerobic digestion. Tripolium pannonicum was grown under hydroponic conditions with different concentrations of SDI (0, 5 and 10mg·L(-1)) and the fresh biomass, containing different amounts of SDI taken up, was used as substrate for biogas production. SDI was analyzed by liquid chromatography coupled to positive ion electrospray mass spectrometry (ESI LC-MS). Based on the findings, T. pannonicum is able to uptake SDI. The more SDI is in the culture medium, the higher the SDI content in the plant tissue. According to this study, it is possible to produce high yields of biogas using biomass of T. pannonicum containing SDI and at the same time biodegradation of SDI is carried out. The highest specific biogas yield is obtained using shoots as substrate of the plants cultivated at 5mg·L(-1) SDI.