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1.
Bol. latinoam. Caribe plantas med. aromát ; 18(5): 480-491, sept. 2019. ilus, tab
Artigo em Inglês | LILACS | ID: biblio-1008273

RESUMO

In the present study, we investigated the antiproliferative activity of essential oil from leaves of Melissa officinalis L. grown in Southern Bosnia and Herzegovina. In vitro evaluation of antiproliferative activity of the M. officinalis essential oil was carried out on three human tumor cell lines: MCF-7, NCI-H460 and MOLT-4 by MTT assay. M. officinalis essential oil was characterized by high percentage of monoterpenes (77,5%), followed by the sesquiterpene fraction (14,5%) and aliphatic compounds (2,2%). The main constituents of the essential oil of M. officinalis are citral (47,2%), caryophyllene oxide (10,2%), citronellal (5,4%), geraniol (6,6%), geranyl acetate (4,1%) and ß- caryophyllene (3,8%). The essential oil showed significant antiproliferative activity against three cancer cell lines, MOLT-4, MCF-7, and NCI-H460 cells, with GI50 values of <5, 6±2 and 31±17 µg/mL, respectively. The results revealed that M. officinalis L. essential oil has a potential as anticancer therapeutic agent.


En el presente estudio, investigamos la actividad antiproliferativa del aceite esencial de las hojas de Melissa officinalis L. cultivadas en el sur de Bosnia y Herzegovina. La evaluación in vitro de la actividad antiproliferativa del aceite esencial de M. officinalis se llevó a cabo en tres líneas celulares de tumores humanos: MCF-7, NCI-H460 y MOLT-4 utilizando el ensayo de MTT. El aceite esencial de M. officinalis se caracterizó por un alto porcentaje de monoterpenos (77,5%), seguido de la fracción sesquiterpénica (14,5%) y compuestos alifáticos (2,2%). Los principales constituyentes del aceite esencial de M. officinalis fueron citral (47,2%), óxido de cariofileno (10,2%), citronelal (5,4%), geraniol (6,6%), acetato de geranilo (4, 1%), y ß-cariofileno (3,8%). El aceite esencial mostró una actividad antiproliferativa significativa contra las líneas celulares de cáncer MOLT-4, MCF-7 y NCI-H460, con valores GI50 de <5, 6±2 y 31±17 µg/mL, respectivamente. Los resultados revelaron que el aceite esencial de M. officinalis L. tiene potencial como agente terapéutico contra el cáncer.


Assuntos
Óleos Voláteis/farmacologia , Melissa , Antineoplásicos/farmacologia , Sesquiterpenos/análise , Técnicas In Vitro , Óleos Voláteis/química , Células Tumorais Cultivadas , Folhas de Planta , Monoterpenos/análise , Linhagem Celular Tumoral/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Cromatografia Gasosa-Espectrometria de Massas , Antineoplásicos/química
2.
J Agric Food Chem ; 67(31): 8500-8509, 2019 Aug 07.
Artigo em Inglês | MEDLINE | ID: mdl-31298534

RESUMO

To map qualitative and quantitative metabolome alterations when Penicillium roqueforti is grown in an environment where l-tyrosine levels are perturbed, the recently established differential off-line LC-NMR (DOLC-NMR) approach was successfully applied in connection with an absolute metabolite quantitation using a quantitative 1H NMR protocol following the ERETIC 2 (Electronic REference To access In vivo Concentrations) methodology. Among the 23 influenced metabolites, amino acid degradation products like 2-(4-hydroxyphenyl)acetic acid and 2-(3,4-dihydroxyphenyl)acetic acid underwent a tremendous upregulation in the amino acid perturbed approach. Moreover, the output of secondary metabolites like andrastin A, eremofortin B, and the tetrapeptide d-Phe-l-Val-d-Val-l-Tyr was affected in the case of the presence or absence of the added aromatic amino acid. Furthermore, the isolated secondary metabolites of P. roqueforti have been quantified for the first time in five divergent Penicillium isolates by means of a validated LC-ECHO-MS/MS method. This technique is used to compensate the effect of co-extracted matrix compounds during the analysis and to utilize quasi-internal standards to quantify all metabolites of interest accurately. This screening outlined the great variety between the different fungi of the same species. The metabolite spectra of wild-type fungi included more toxic intermediates compared to a selected fungi used as a starter culture for blue-mold cheese production. In addition, these secondary metabolites were quantified in commercially available white- and blue-mold cheese samples. The main differences between the analyte profiles of white and blue cheeses were linked to the impact of the used starter culture. Specific metabolites detected from P. roqueforti like andrastin A and B or roquefortine C could not be detected in white cheese. Among the blue cheese samples, different metabolite pattern could be observed regarding various P. roqueforti starter cultures.


Assuntos
Queijo/microbiologia , Metaboloma , Penicillium/metabolismo , Metabolismo Secundário , Tirosina/metabolismo , Aminoácidos Aromáticos/análise , Aminoácidos Aromáticos/metabolismo , Androstadienos/análise , Androstadienos/metabolismo , Queijo/análise , Penicillium/química , Penicillium/crescimento & desenvolvimento , Peptídeos/análise , Peptídeos/metabolismo , Sesquiterpenos/análise , Sesquiterpenos/metabolismo , Espectrometria de Massas em Tandem
3.
Food Chem ; 299: 125101, 2019 Nov 30.
Artigo em Inglês | MEDLINE | ID: mdl-31323442

RESUMO

Terpenes and their derivatives, terpenoids, are important biomarkers of grape quality as they contribute to flavor and aroma of grape and wine. The evolution of terpene and terpenoids throughout grapevine phenological development cycles is not well understood. The current study investigated the volatile profiles of free terpene and terpenoid of five widely grown Vitis vinifera L. cultivars (Shiraz, Cabernet Sauvignon, Riesling, Chardonnay and Pinot Gris), at different phenological stages from fruit-set to harvest. 17 Monoterpenoids, 3 norisoprenoid and 13 sesquiterpenoids were identified and quantified. Discriminant analysis revealed that for each grape cultivar, free terpene profiles at different E-L stages were distinctive. When integrating total sugar, total terpenes and the cumulated heat index, it could be found that flavor ripening was more consistent with sugar ripening in the warmer vintage 2016. Comparing the two red wine varieties, the overall development patterns of total monoterpenes, norisoprenoids and sesquiterpenes were similar.


Assuntos
Terpenos/metabolismo , Vitis/crescimento & desenvolvimento , Vitis/metabolismo , Austrália , Frutas/crescimento & desenvolvimento , Frutas/metabolismo , Norisoprenoides/análise , Norisoprenoides/metabolismo , Sesquiterpenos/análise , Sesquiterpenos/metabolismo , Especificidade da Espécie , Terpenos/análise , Compostos Orgânicos Voláteis/análise , Vinho/análise
4.
Bol. latinoam. Caribe plantas med. aromát ; 18(4): 435-443, jul. 2019. ilus, tab
Artigo em Inglês | LILACS | ID: biblio-1008258

RESUMO

Volatiles compounds are involved in defensive induction against insects, playing an important role in insect-plant interaction being induced by response to mechanical damage. However, they could decrease according to the domestication degree in cultivated plants. Currently, it has been established that secondary metabolites are reduced due to the domestication process in murtilla. Hence, the follow question emerges: Are volatile organic compounds induced by mechanical damage reduced in cultivated murtilla plants in relation to wild plants? Two cultivated ecotypes and their respective wild counterparts were sampled. Volatiles compounds were obtained using Porapak-Q columns and analyzed by gas chromatography. Results showed that compounds as 2-hexanone, α-pinene, 2-thujene, 3-thujene and 1,8- cineole were more abundant in wild plants exposed to a mechanical damage than cultivated plants. Hence, these compounds have been associated to induced defense, these results suggest that domestication reduced the induction of defensive volatiles in cultivated murtilla in response to mechanical damage.


Los compuestos volátiles están implicados en la defensa inducida contra insectos, desempeñando un papel importante en esta interacción. Sin embargo, estos compuestos podrían disminuir según el grado de domesticación. Actualmente, se ha reportado que algunos metabolitos secundarios son reducidos en plantas de murtilla domesticadas. Por lo tanto, surge la siguiente pregunta de investigación: ¿Los compuestos orgánicos volátiles inducidos por el daño mecánico son reducidos en plantas cultivadas de murtilla en comparación con plantas silvestres? Para dos ecotipos cultivados y sus respectivas contrapartes silvestres, los compuestos volátiles fueron capturados usando columnas de Porapak-Q y las muestras analizadas por cromatografía gaseosa. Los resultados mostraron que compuestos tales como 2- hexanona, α-pineno, 2-tujeno, 3-tujeno y 1,8-cineol fueron más abundantes en plantas silvestres expuestas a daño mecánico que en cultivadas. Debido a que estos compuestos se han asociado a defensa inducida, estos resultados sugieren que la domesticación reduce la inducción de volátiles en plantas cultivadas sometidas a daño mecánico.


Assuntos
Animais , Óleos Voláteis/metabolismo , Myrtaceae/metabolismo , Myrtaceae/microbiologia , Domesticação , Insetos/fisiologia , Sesquiterpenos/análise , Sesquiterpenos/metabolismo , Óleos Voláteis/química , Myrtaceae/química , Monoterpenos/análise , Monoterpenos/metabolismo , Meio Selvagem , Larva/fisiologia , Cromatografia Gasosa-Espectrometria de Massas
5.
Phytochemistry ; 164: 144-153, 2019 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-31151061

RESUMO

Triquinane is a type of sesquiterpenoid with a unique structure that contains a fused tricyclopentane ring and exhibits a wide range of bioactivities. Like other sesquiterpenoids, the first committed step in triquinane-type sesquiterpenoid biosynthesis is the cyclization of farnesyl pyrophosphate (FPP), a common precursor of all sesquiterpenoids, catalyzed by sesquiterpene synthase. Artemisia abrotanum L. (Asteraceae), a common plant used in the culinary and cosmetics industries, has been reported to accumulate high levels of triquinane silphiperfol-5-en-3-one A. This compound is potentially biosynthesized from the cyclization of FPP into 7-epi-silphiperfol-5-ene followed by a multi-step oxidation to silphiperfol-5-en-3-one A. In this study, we aimed to identify the sesquiterpene synthase responsible for the synthesis of 7-epi-silphiperfol-5-ene. We performed RNA sequencing of A. abrotanum leaves and gene candidates were mined by homology searches using the triquinane α-isocomene synthase of chamomile (MrTPS2) as query. After gene cloning, we obtained five variants of putative sesquiterpene synthase showing greater than 85% amino acid identity to MrTPS2 and greater than 95% amino acid identity to each other. Heterologous expression of these variants in a FPP-high-producing yeast strain revealed the first four variants to be (+)-α-bisabolol synthases (AabrBOS1-4). However, the fifth candidate cyclized FPP into 7-epi-silphiperfol-5-ene and can therefore be defined as a 7-epi-silphiperfol-5-ene synthase (AabrSPS). These findings revealed the first committed enzyme involved in silphiperfol-5-en-3-one A and (+)-α-bisabolol biosyntheses in A. abrotanum. Furthermore, the results of this study will be useful for enhancing the production of these compounds for further applications.


Assuntos
Alquil e Aril Transferases/análise , Artemisia/química , Artemisia/enzimologia , Sesquiterpenos/análise , Alquil e Aril Transferases/metabolismo , Artemisia/metabolismo , Relação Dose-Resposta a Droga , Conformação Molecular , Sesquiterpenos/metabolismo , Relação Estrutura-Atividade
6.
Environ Pollut ; 252(Pt A): 493-500, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31163382

RESUMO

Thirteen secondary organic aerosol (SOA) tracers of isoprene, monoterpenes and sesquiterpenes were measured for PM2.5 aerosols collected at the summit of Mt. Wuyi (1139 m, a.s.l.), to investigate their seasonality and formation mechanism. Concentrations of the isoprene and monoterpene SOA tracers were much higher in summer than those in other seasons. In contrast, ß-caryophyllinic acid was found to be the lowest in summer. Concentrations of those BSOA tracers showed a positive correlation with temperature (R2 = 0.52-0.70), and a negative correlation with relative humidity (R2 = 0.43-0.78). Moreover, thermodynamic model (i.e., ISORROPIA-II) calculation results showed that acidity conditions are favorable for BSOA formation. Robust linear correlations between the BSOA tracers and anthropogenic pollutants such as SO2 (R2 = 0.53-0.7) and NO2 (R2 = 0.37-0.54) were observed for all the samples, suggesting that SO2 and NOx can enhance BSOA production in the remote mountain area of southeast China, which is related to an acid-catalyzed heterogeneous chemistry. Moreover, we also found a significant correlation between the concentrations of the BSOA tracers and levoglucosan especially for ß-caryophyllinic acid, indicating that biomass burning plumes from the distant lowland regions could influence the production of BSOA in the mountain free troposphere. Our results clearly demonstrated that anthropogenic emissions in China could enhance BSOA formation in the distant mountain regions.


Assuntos
Aerossóis/análise , Poluentes Atmosféricos/análise , Butadienos/análise , Monitoramento Ambiental , Hemiterpenos/análise , Monoterpenos/análise , Sesquiterpenos/análise , Biomassa , China , Material Particulado/análise , Estações do Ano
7.
J Chromatogr A ; 1601: 178-188, 2019 Sep 13.
Artigo em Inglês | MEDLINE | ID: mdl-31056269

RESUMO

Three immobilized polysaccharide chiral stationary phases, Chiralpak IA, Chiralpak IB and Chiralpak IC, were used for the study of enantioseparation of 36 derivatives of natural indole phytoalexins, in most cases bioactive, including racemic spirobrassinin, 1-methoxyspirobrassinin and 1-methoxyspirobrassinol methyl ether. Almost all analytes were baseline resolved at least on two different polysaccharide columns in normal phase mode. The effects of mobile phase composition, the analyte structure and the column temperature on the retention and enantioseparation were investigated. Evaluation of the corresponding thermodynamic parameters using van´t Hoff plots (ln k versus 1/T) in the temperature range -15 to 50 °C indicated that separations were enthalpy controlled in most cases, but some entropy controlled separations were also observed. Moreover, unusual phenomenon, an increase retention with increasing temperature accompanied with increased resolution was observed on the Chiralpak IC column. The elution order of enantiomers was determined in some cases and reversed elution order was also observed.


Assuntos
Cromatografia Líquida , Sesquiterpenos/química , Temperatura Ambiente , Polissacarídeos/química , Sesquiterpenos/análise , Estereoisomerismo , Termodinâmica
8.
Molecules ; 24(8)2019 Apr 18.
Artigo em Inglês | MEDLINE | ID: mdl-31003442

RESUMO

Objective: To develop an accurate and rapid ultra-performance liquid chromatography (UPLC) coupled with a photodiode array (PDA) method for the simultaneous determination of artemisinin (Art), arteannuin B (Art B), arteannuin C (Art C), dihydroartemisinic acid (DHAA) and artemisinic acid (AA) in Artemisia annua L. Methodology: Chromatography separation was performed on an ACQUITY UPLC BEH C18 Column with isocratic elution; the mobile phase was 0.1% formic acid aqueous solution (A) and acetonitrile (B) (A:B = 40:60, v/v). Data were recorded at an ultraviolet (UV) wavelength of 191 nm for Art, Art C, DHAA and AA, and 206 nm for Art B. Results: The calibration curves of the five sesquiterpene components were all linear with correlation coefficients more than 0.9990. The linear ranges were 31.44-1572 µg/mL, 25.48-1274 µg/mL, 40.56-2028 µg/mL, 31.44-1572 µg/mL and 26.88-1396 µg/mL for Art, Art B, Art C, DHAA and AA, respectively. The precision ranged from 0.08% to 2.88%, the stability was from 0.96% to 1.66%, and the repeatability was all within 2.42% and had a mean extraction recovery of 96.5% to 100.6%. Conclusion: The established UPLC-PDA method would be valuable for improving the quantitative analysis of sesquiterpene components in Artemisia annua L.


Assuntos
Artemisia annua/química , Bioensaio/métodos , Cromatografia Líquida de Alta Pressão/métodos , Óptica e Fotônica/instrumentação , Sesquiterpenos/análise , Sesquiterpenos/isolamento & purificação , Ultrassom/métodos , Extratos Vegetais/análise , Análise de Regressão , Reprodutibilidade dos Testes
9.
Spectrochim Acta A Mol Biomol Spectrosc ; 217: 271-277, 2019 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-30947136

RESUMO

Molecularly imprinted polymers provide an excellent platform for the modification of selective electrodes for sensing applications. Herein, we present a novel modified carbon paste electrode (CPE) with a selective molecularly imprinted polymer (MIP) for recognition of sesquiterpene ß-caryophyllene, constituted of important plants oil-resins and extracts. The non-covalent MIP was synthesized using AA, EGDMA, and AIBN as a functional monomer, cross-linker and initiator agent, respectively. Structural and chemical characterization of the synthesized MIP was conducted through scanning electron microscopy (SEM), Fourier-transform infrared (FT-IR) spectroscopy, Raman spectroscopy and X-ray photoelectron spectroscopy (XPS). It was possible to verify the functional features of the synthesized MIP related to the extraction process of the template molecule. The CPE modified with MIP for sesquiterpene ß-caryophyllene recognition was characterized by electrochemical techniques as cyclic voltammetry (CV) and square wave voltammetry (SWV). The highest selective recognition electrode enables to detect concentrations in the range between 1.5 × 10-7 and 7.5 × 10-7 M, showing great potential for applications in monitoring content of sesquiterpene ß-caryophyllene in technological processes and for predicting the quality of extracts, oils, and resins of plants.


Assuntos
Anti-Inflamatórios não Esteroides/análise , Técnicas Biossensoriais/métodos , Técnicas Eletroquímicas/métodos , Impressão Molecular/métodos , Polímeros/química , Sesquiterpenos/análise , Anti-Inflamatórios não Esteroides/química , Eletrodos , Limite de Detecção , Sesquiterpenos/química
10.
Molecules ; 24(8)2019 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-31027274

RESUMO

The chemical composition and biological activity of essential oils isolated from the leaves of Siparuna aspera, Siparuna macrotepala, Piper leticianum, Piper augustum and the rhizome of Hedychium coronarium were evaluated. These species are used medicinally in different ways by the Amazonian communities that live near the Kutukú mountain range. Chemical studies revealed that the main components for the two Siparuna species were germacrene D, bicyclogermacrene, α-pinene, δ-cadinene, δ-elemene, α-copaene and ß-caryophyllene; for the two Piper species ß-caryophyllene, germacrene D, α-(E,E)-farnesene, ß-elemene, bicyclogermacrene, δ-cadinene and for H. coronarium 1,8-cineole, ß-pinene, α-pinene and α-terpineol. The antioxidant activity of all essential oils was evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), photochemiluminescence (PCL) quantitative assays, and DPPH and ABTS bioautographic profiles, with different results for each of them. Antimicrobial activity studies were carried out on three yeasts, six Gram positive and four Gram negative bacteria, by means of the disc diffusion method. The essential oil of H. coronarium showed the most relevant results on L. grayi, K. oxytoca and S. mutans, P. augustum and P. leticianum on S. mutans. An antibacterial bioautographic test for H. coronarium was also carried out and highlighted the potential activity of terpinen-4-ol and 1,8-cineole.


Assuntos
Óleos Voláteis/análise , Zingiberaceae/química , Antibacterianos/análise , Antibacterianos/farmacologia , Compostos Bicíclicos com Pontes/análise , Compostos Bicíclicos com Pontes/farmacologia , Cicloexenos/análise , Cicloexenos/farmacologia , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Monoterpenos/análise , Monoterpenos/farmacologia , Óleos Voláteis/farmacologia , Floresta Úmida , Sesquiterpenos/análise , Sesquiterpenos/farmacologia
11.
J Environ Sci (China) ; 81: 102-118, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30975314

RESUMO

Biological volatile organic compounds (BVOCs) have a large influence on atmospheric environmental quality, climate change and the carbon cycle. This study assesses the composition and diurnal variation in emission rates of BVOCs from Pinus tabuliformis, using an enclosure technique. Environmental parameters (temperature and light intensity) and physiological parameters (net photosynthetic rate, Pn; stomatal conductance, gs; intercellular CO2 concentration, Ci; and transpiration rate, Tr) that may affect emission behavior were continuously monitored. The 10 most abundant compound groups emitted by P. tabuliformis were classified by gas chromatography-mass spectrometry. The dominant monoterpenoid compounds emitted were α-pinene, ß-myrcene, α-farnesene and limonene. The diurnal emission rate of BVOCs changed with temperature and light intensity, with dynamic analysis of BVOCs emissions revealing that their emission rates were more affected by temperature than light. The variation in monoterpene emission rates was consistent with estimates of Pn, gs and Tr. Basal emission rates (at 30 °C,) of the main BVOCs ranged from 0.006 to 0.273 µg  -1/(hr g), while the basal ER standardization coefficients ranged from 0.049 to 0.144 °C-1. Overall, these results provide a detailed reference for the effective selection and configuration of tree species to effectively prevent and control atmospheric pollution.


Assuntos
Poluentes Atmosféricos/análise , Monitoramento Ambiental , Pinus/fisiologia , Compostos Orgânicos Voláteis/análise , Monoterpenos/análise , Pinus/química , Sesquiterpenos/análise
12.
Planta ; 250(1): 79-94, 2019 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-30919065

RESUMO

MAIN CONCLUSION: Mouse FIT2 protein redirects the cytoplasmic terpene biosynthetic machinery to lipid-droplet-forming domains in the ER and this relocalization supports the efficient compartmentalization and accumulation of sesquiterpenes in plant cells. Mouse (Mus musculus) fat storage-inducing transmembrane protein 2 (MmFIT2), an endoplasmic reticulum (ER)-resident protein with an important role in lipid droplet (LD) biogenesis in mammals, can function in plant cells to promote neutral lipid compartmentalization. Surprisingly, in affinity capture experiments, the Nicotiana benthamiana 5-epi-aristolochene synthase (NbEAS), a soluble cytoplasm-localized sesquiterpene synthase, was one of the most abundant proteins that co-precipitated with GFP-tagged MmFIT2 in transient expression assays in N. benthamiana leaves. Consistent with results of pull-down experiments, the subcellular location of mCherry-tagged NbEAS was changed from the cytoplasm to the LD-forming domains in the ER, only when co-expressed with MmFIT2. Ectopic co-expression of NbEAS and MmFIT2 together with mouse diacylglycerol:acyl-CoA acyltransferase 2 (MmDGAT2) in N. benthamiana leaves substantially increased the numbers of cytoplasmic LDs and supported the accumulation of the sesquiterpenes, 5-epi-aristolochene and capsidiol, up to tenfold over levels elicited by Agrobacterium infection alone. Taken together, our results suggest that MmFIT2 recruits sesquiterpene synthetic machinery to ER subdomains involved in LD formation and that this process can enhance the efficiency of sesquiterpene biosynthesis and compartmentalization in plant cells. Further, MmFIT2 and MmDGAT2 represent cross-kingdom lipogenic protein factors that may be used to engineer terpene accumulation more broadly in the cytoplasm of plant vegetative tissues.


Assuntos
Gotículas Lipídicas/metabolismo , Proteínas de Membrana/metabolismo , Sesquiterpenos/metabolismo , Tabaco/metabolismo , Triglicerídeos/metabolismo , Animais , Vias Biossintéticas , Citoplasma/metabolismo , Retículo Endoplasmático/metabolismo , Gotículas Lipídicas/química , Proteínas de Membrana/genética , Camundongos , Especificidade de Órgãos , Células Vegetais/metabolismo , Folhas de Planta/citologia , Folhas de Planta/genética , Folhas de Planta/metabolismo , Proteômica , Sesquiterpenos/análise , Terpenos/metabolismo , Tabaco/citologia , Tabaco/genética , Triglicerídeos/análise
13.
Phytochemistry ; 162: 29-38, 2019 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-30851508

RESUMO

Essential oils (EOs) obtained from aerial parts and roots of Elionurus tristis were investigated by GC, GC-MS, pc-GC and NMR. Both aerial parts and roots EOs contained common molecules such as α-pinene, camphene, trans-α-bergamotene and calarene. Moreover, we identified several unusual sesquiterpenes and four undescribed compounds, 7-epi-khusian-2-ol, 4,8-di-epi-acorone, 2-epi-ziza-5-en-2-ol and antsorenone. The last one exhibits an undescribed natural sesquiterpene skeleton. All undescribed compounds were isolated and fully characterized by MS, 1D and 2D-NMR. Furthermore, the formation pathway of the Antsorane skeleton is discussed.


Assuntos
Óleos Voláteis/química , Poaceae/química , Sesquiterpenos/análise , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Estereoisomerismo
14.
An Acad Bras Cienc ; 91(1): e20180498, 2019 Mar 21.
Artigo em Inglês | MEDLINE | ID: mdl-30916159

RESUMO

Lippia rotundifolia is an aromatic species, native and endemic to rocky fields, which are isolated by small mountains. It is little known about their chemical composition. Because of that we aimed to study the chemical diversity of volatiles released from rosemary leaves (Lippia rotundifolia Cham.) coming from 11 populations of the Minas Gerais, Brazil. The material for chemical analysis was obtained from the accessions in the active germplasm bank of the Instituto de Ciências agrárias of the Universidade Federal de Minas Gerais. A total of 67 compounds were detected by HS-CG-MS. Most volatiles were detected in the São Gonçalo do Rio das Pedras accession, with 40 compounds, whereas in the Santana do Riacho accession only 5 compounds were detected. Volatiles myrcene, linalool and caryophyllene were detected in the majority of the accessions. We concluded that Lippia rotundifolia presents high chemical variability. The volatiles mircene, linalool and caryophyllene are the most frequent, detected in most of the accessions. Due to some accession to present predominance of monoterpenes, others sesquiterpenes, studies of molecular analysis are necessary for associate the chemotypes, since environmental variation influence the gene expression of the secondary metabolites.


Assuntos
Lippia/química , Compostos Orgânicos Voláteis/análise , Brasil , Cromatografia Gasosa-Espectrometria de Massas , Lippia/genética , Monoterpenos/análise , Sesquiterpenos/análise
15.
Molecules ; 24(5)2019 Feb 28.
Artigo em Inglês | MEDLINE | ID: mdl-30823439

RESUMO

An analytical method using UHPLC-MS was developed and applied to 16 crude CH2Cl2 extracts from Australian Celastraceae plants; the endemic plant materials were accessed from Griffith University's NatureBank resource and included bark, fruit, leaf, root, twig and mixed samples, all of which were collected from Queensland, Australia. The generated UHPLC-MS data were analysed and dereplicated using the scientific databases Dictionary of Natural Products and SciFinder Scholar in order to potentially identify new dihydro-ß-agarofurans from local Celastraceae plants. These investigations led to the large-scale extraction and isolation work on a prioritised fruit sample that belonged to the rainforest plant Denhamia celastroides. Chemical investigations resulted in the purification of four new natural products, denhaminols O⁻R (1⁻4), along with the related and known compound, denhaminol G (5). The structures of all the new compounds were determined via detailed analysis of NMR and MS data.


Assuntos
Celastraceae/química , Extratos Vegetais/química , Sesquiterpenos/análise , Sesquiterpenos/química , Austrália , Cromatografia Líquida de Alta Pressão , Espectrometria de Massas , Floresta Úmida
16.
Environ Sci Pollut Res Int ; 26(14): 14036-14049, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30852752

RESUMO

The study reports efficacy of Melissa officinalis L. essential oil (MOEO) as a safe plant-based insecticide against Tribolium castaneum Herbst (TC) by induction of oxidative stress. MOEO nanoencapsulation in chitosan matrix was performed to enhance its bioefficacy. GC-MS analysis of MOEO depicted geranial (31.54%), neral (31.08%), and ß-caryophyllene (12.42%) as the major components. MOEO showed excellent insecticidal potential in contact (100% mortality at 0.157 µL/cm2) and fumigant bioassays (LC50 = 0.071 µL/mL air) and 100% repellency at concentration ≤ 0.028 µL/cm2. Increased reactive oxygen species (ROS), superoxide dismutase (SOD), catalase (CAT), and decreased ratio of reduced glutathione (GSH) to oxidized glutathione (GSSG) at the LC50 dose suggested significant oxidative stress on TC in MOEO treatment sets. The encapsulated MOEO exhibited enhanced activity as fumigant (LC50 = 0.048 µL/mL air) and showed significant antifeedant activity in situ (EC50 = 0.043 µL/mL). High LD50 value (13,956.87 µL/kg body weight of mice) confirmed favorable toxicological profile for non-target mammals. The findings depict potential of nanoencapsulated MOEO as an eco-friendly green pesticide against infestation of stored food by TC.


Assuntos
Farinha , Repelentes de Insetos/farmacologia , Melissa/química , Óleos Voláteis/farmacologia , Tribolium/efeitos dos fármacos , Animais , Armazenamento de Alimentos , Cromatografia Gasosa-Espectrometria de Massas , Repelentes de Insetos/análise , Repelentes de Insetos/toxicidade , Dose Letal Mediana , Masculino , Camundongos , Monoterpenos/análise , Óleos Voláteis/análise , Óleos Voláteis/toxicidade , Estresse Oxidativo/efeitos dos fármacos , Espécies Reativas de Oxigênio/metabolismo , Sesquiterpenos/análise , Tribolium/fisiologia , Triticum
17.
Food Chem ; 275: 15-23, 2019 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-30724181

RESUMO

This study investigated the volatile phytochemical diversity of 30 samples obtained from experimental hybrid and commercial H. lupulus L. plants. Essential oils distilled from these samples were analysed by high resolution gas chromatography coupled with accurate mass time-of-flight mass spectrometry (GC-accTOFMS). A total of 58 secondary metabolites, mainly comprising 18 esters, 6 monoterpene hydrocarbons, 2 oxygenated monoterpenes, 20 sesquiterpene hydrocarbons, 7 oxygenated sesquiterpenes, and 4 ketones, were positively or tentatively identified. A total of 24 metabolites were detected in all samples, but commercial cultivars (selected for brewing performance) had fewer compounds identified compared to experimental genotypes. Chemometrics analyses enabled distinct differentiation of experimental hybrids from commercial cultivars, discussed in terms of the different classes of compounds present in different genotypes. Differences among the mono- and sesquiterpenoids, appear to be related to either: i) the genetic origin of the plants; or ii) the processes of bioaccumulation of the identified secondary metabolites.


Assuntos
Humulus/química , Óleos Voláteis/análise , Austrália , Cerveja , Cromatografia Gasosa-Espectrometria de Massas/métodos , Genótipo , Humulus/genética , Humulus/metabolismo , Monoterpenos/análise , Óleos Voláteis/química , Compostos Fitoquímicos/análise , Metabolismo Secundário , Sesquiterpenos/análise
18.
Phytomedicine ; 54: 195-205, 2019 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-30668369

RESUMO

BACKGROUND: Zingiber zerumbet rhizome has been used as spices and in traditional medicine to heal various immune-inflammatory related ailments. Although the plant was reported to have potent anti-inflammatory and immunosuppressive properties by several studies, the molecular mechanisms underlying the effects have not been well justified. PURPOSE: The study was carried out to investigate the molecular mechanisms underlying the anti-inflammatory properties of the standardized 80% ethanol extract of Z. zerumbet through its effect on mitogen-activated protein kinase (MyD88)-dependent nuclear factor-kappa B (NF-кB), mitogen activated protein kinase (MAPK) and phosphatidylinositol 3-kinase/Akt (PI3K-Akt) signaling pathways in lipopolysaccharide (LPS)-induced U937 human macrophages. METHODS: Standardization of the 80% ethanol extract of Z. zerumbet was performed by using a validated reversed-phase HPLC method, while LC-MS/MS was used to profile the secondary metabolites. The release of pro-inflammatory markers, tumor necrosis factor (TNF)-α, interleukin (IL)-1ß and prostaglandin E2 (PGE2) was evaluated by enzyme-linked immunosorbent assay (ELISA), while the Western blot technique was executed to elucidate the expression of mediators linked to MyD88-dependent respective signaling pathways. Real-time quantitative reverse transcription polymerase chain reaction (qRT-PCR) assay was carried out to quantify the relative gene expression of cyclooxygenase (COX)-2 and pro-inflammatory mediators at the transcriptional level. RESULTS: The quantitative and qualitative analyses of Z. zerumbet extract showed the presence of several compounds including the major chemical marker zerumbone. Z. zerumbet extract suppressed the release of pro-inflammatory mediators, COX-2 protein expression and downregulated the mRNA expression of pro-inflammatory markers. Z. zerumbet-treatment also blocked NF-κB activation by preventing the phosphorylation of IKKα/ß and NF-κB (p65) as well as the phosphorylation and degradation of IκBα. Z. zerumbet extract concentration-dependently inhibited the phosphorylation of respective MAPKs (JNK, ERK, and p38) as well as Akt. Correspondingly, Z. zerumbet extract suppressed the upstream signaling adaptor molecules, TLR4 and MyD88 prerequisite for the NF-κB, MAPKs, and PI3K-Akt activation. CONCLUSION: The findings suggest that Z. zerumbet has impressive role in suppressing inflammation and related immune disorders by inhibition of various pro-inflammatory markers through the imperative MyD88-dependent NF-κB, MAPKs, and PI3K-Akt activation.


Assuntos
Anti-Inflamatórios não Esteroides/farmacologia , Inflamação/tratamento farmacológico , Inflamação/metabolismo , Extratos Vegetais/farmacologia , Zingiberaceae/química , Anti-Inflamatórios não Esteroides/química , Biomarcadores/metabolismo , Cromatografia Líquida , Humanos , Lipopolissacarídeos/farmacologia , Proteínas Quinases Ativadas por Mitógeno/metabolismo , NF-kappa B/metabolismo , Fosfatidilinositol 3-Quinases/metabolismo , Extratos Vegetais/química , Extratos Vegetais/normas , Proteínas Proto-Oncogênicas c-akt/metabolismo , Sesquiterpenos/análise , Transdução de Sinais/efeitos dos fármacos , Espectrometria de Massas em Tandem , Células U937
19.
Plant Physiol ; 179(2): 382-390, 2019 02.
Artigo em Inglês | MEDLINE | ID: mdl-30538166

RESUMO

Red algae (Rhodophyta) and land plants belong to the monophyletic clade Archaeplastida, and taxa of both groups are rich producers of terpene secondary metabolites. The terpene carbon skeletons of land plants are made by two types of terpene synthases: typical plant terpene synthases and microbial-type terpene synthases (MTPSLs); however, terpene biosynthesis in red algae is poorly understood. By systematic sequence analysis of seven genomes and 34 transcriptomes of red algae, MTPSL homologs were identified within one genome and two transcriptomes, whereas no homolog of typical plant terpene synthase genes was found. Phylogenetic analysis showed that red algae MTPSLs group with bacterial terpene synthases. Analysis of the genome assembly and characterization of neighboring genes demonstrated red algal MTPSLs to be bona fide red algal genes and not microbial contaminants. MTPSL genes from Porphyridium purpureum and Erythrolobus australicus were characterized via heterologous expression in Escherichia coli and demonstrated to have sesquiterpene synthase activities. We detected a number of volatile sesquiterpenes in the headspace of P. purpureum and E. australicus cultures, most identical to the in vitro products of the respective MTPSLs. Expression of the MTPSL gene in P. purpureum was found to be induced by methyl jasmonate, suggesting a role for this gene in host defense. In summary, this study indicates that the formation of terpene carbon skeletons in red algae is carried out by MTPSLs that are phylogenetically unrelated to typical plant terpene synthases and most likely originated in Rhodophyta via horizontal gene transfer from bacteria.


Assuntos
Proteínas de Algas/metabolismo , Alquil e Aril Transferases/metabolismo , Proteínas de Bactérias/metabolismo , Rodófitas/genética , Terpenos/metabolismo , Acetatos/farmacologia , Proteínas de Algas/genética , Alquil e Aril Transferases/genética , Proteínas de Bactérias/genética , Ciclopentanos/farmacologia , Evolução Molecular , Regulação Enzimológica da Expressão Gênica/efeitos dos fármacos , Oxilipinas/farmacologia , Filogenia , Porphyridium/efeitos dos fármacos , Porphyridium/genética , Porphyridium/metabolismo , Rodófitas/citologia , Rodófitas/metabolismo , Sesquiterpenos/análise , Sesquiterpenos/metabolismo , Técnicas de Cultura de Tecidos , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/metabolismo
20.
Molecules ; 23(12)2018 Dec 11.
Artigo em Inglês | MEDLINE | ID: mdl-30544938

RESUMO

Isoprenoids (IsoP) are an important class of molecules involved in many different cellular processes including cholesterol synthesis. We have developed a sensitive and specific LC-MS/MS method for the quantitation of three key IsoPs in bio-matrices, geranyl pyrophosphate (GPP), farnesyl pyrophosphate (FPP), and geranylgeranyl pyrophosphate (GGPP). LC-MS/MS analysis was performed using a Nexera UPLC System connected to a LCMS-8060 (Shimadzu Scientific Instruments, Columbia, MD) with a dual ion source. The electrospray ionization source was operated in the negative MRM mode. The chromatographic separation and detection of analytes was achieved on a reversed phase ACCQ-TAG Ultra C18 (1.7 µm, 100 mm × 2.1 mm I.D.) column. The mobile phase consisted of (1) a 10 mM ammonium carbonate with 0.1% ammonium hydroxide in water, and (2) a 0.1% ammonium hydroxide in acetonitrile/methanol (75/25). The flow rate was set to 0.25 mL/min in a gradient condition. The limit of quantification was 0.04 ng/mL for all analytes with a correlation coefficient (r2) of 0.998 or better and a total run time of 12 min. The inter- and intra-day accuracy (85⁻115%) precision (<15%), and recovery (40⁻90%) values met the acceptance criteria. The validated method was successfully applied to quantitate basal concentrations of GPP, FPP and GGPP in human plasma and in cultured cancer cell lines. Our LC-MS/MS method may be used for IsoP quantification in different bio-fluids and to further investigate the role of these compounds in various physiological processes.


Assuntos
Cromatografia Líquida/métodos , Fosfatos de Poli-Isoprenil/análise , Sesquiterpenos/análise , Espectrometria de Massas em Tandem/métodos , Calibragem , Linhagem Celular Tumoral , Humanos , Neoplasias Pancreáticas/química , Neoplasias Pancreáticas/patologia , Fosfatos de Poli-Isoprenil/sangue , Reprodutibilidade dos Testes , Sensibilidade e Especificidade , Sesquiterpenos/sangue
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