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2.
J Chem Ecol ; 46(1): 30-39, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31808075

RESUMO

Cerambycid beetles of the subfamily Lamiinae use male-produced aggregation-sex pheromones that are attractive to both sexes. Terpenoid pheromones have been identified from species in the tribes Acanthoderini and Acanthocinini native to North and South America, comprised of (E)-6,10-dimethyl-5,9-undecadien-2-one (geranylacetone), the structurally related 6-methylhept-5-en-2-one (sulcatone), and/or specific enantiomers or nonracemic ratios of enantiomers of the related compounds (E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol), its acetate ester, (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate), and 6-methylhept-5-en-2-ol (sulcatol). Here, we present new information about the chemical ecology of six acanthoderine and acanthocinine species native to the eastern USA. The pheromone of Astyleiopus variegatus (Haldeman) previously was identified as a blend of (S)-fuscumol and (S)-fuscumol acetate, and we report here that geranylacetone is a synergistic component. Males of Aegomorphus modestus (Gyllenhal), Lepturges angulatus (LeConte), and Lepturges confluens (Haldeman) were found to produce similar blends composed of the enantiomers of fuscumol acetate and geranylacetone, whereas males of Astylidius parvus (LeConte) and Sternidius alpha (Say) produced both enantiomers of fuscumol together with (R)-fuscumol acetate and geranylacetone. Field experiments with synthesized chemicals revealed that species with similar pheromone composition nevertheless differed in their responses to individual components, and to various blends of components, and in how attraction was influenced by chemicals that were pheromone components of other species. Sulcatone and/or sulcatol antagonized attraction of some species to pheromones of the geranylacetone class, suggesting that there is an adaptive advantage in an ability to detect these heterospecific compounds, such as in avoiding cross attraction to other cerambycid species, as yet unknown, that use pheromones composed of both chemical classes.


Assuntos
Besouros/química , Feromônios/química , Animais , Besouros/metabolismo , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Masculino , Feromônios/isolamento & purificação , Feromônios/farmacologia , Comportamento Sexual Animal/efeitos dos fármacos , Especificidade da Espécie , Estereoisomerismo , Terpenos/química , Terpenos/isolamento & purificação , Terpenos/farmacologia , Compostos Orgânicos Voláteis/química , Compostos Orgânicos Voláteis/isolamento & purificação , Compostos Orgânicos Voláteis/farmacologia
3.
J Enzyme Inhib Med Chem ; 35(1): 152-164, 2020 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31742469

RESUMO

Overexpression of protein tyrosine phosphatase 1B (PTP1B) induces insulin resistance in various basic and clinical research. In our previous work, a synthetic oleanolic acid (OA) derivative C10a with PTP1B inhibitory activity has been reported. However, C10a has some pharmacological defects and cytotoxicity. Herein, a structure-based drug design approach was used based on the structure of C10a to elaborate the smaller tricyclic core. A series of tricyclic derivatives were synthesised and the compounds 15, 28 and 34 exhibited the most PTP1B enzymatic inhibitory potency. In the insulin-resistant human hepatoma HepG2 cells, compound 25 with the moderate PTP1B inhibition and preferable pharmaceutical properties can significantly increase insulin-stimulated glucose uptake and showed the insulin resistance ameliorating effect. Moreover, 25 showed the improved in vivo antihyperglycaemic potential in the nicotinamide-streptozotocin-induced T2D. Our study demonstrated that these tricyclic derivatives with improved molecular architectures and antihyperglycaemic activity could be developed in the treatment of T2D.


Assuntos
Diabetes Mellitus Tipo 2/tratamento farmacológico , Desenho de Drogas , Inibidores Enzimáticos/farmacologia , Hipoglicemiantes/farmacologia , Proteína Tirosina Fosfatase não Receptora Tipo 1/antagonistas & inibidores , Terpenos/farmacologia , Animais , Glicemia/efeitos dos fármacos , Diabetes Mellitus Tipo 2/metabolismo , Modelos Animais de Doenças , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/química , Células Hep G2 , Humanos , Hipoglicemiantes/síntese química , Hipoglicemiantes/química , Resistência à Insulina , Masculino , Camundongos , Camundongos Endogâmicos , Estrutura Molecular , Proteína Tirosina Fosfatase não Receptora Tipo 1/metabolismo , Relação Estrutura-Atividade , Terpenos/síntese química , Terpenos/química
4.
J Agric Food Chem ; 68(1): 315-322, 2020 Jan 08.
Artigo em Inglês | MEDLINE | ID: mdl-31851503

RESUMO

This study assesses whether the distinct altitudinal cline in leaf morphology (decreased leaf width and length with increased altitude) in Tasmanian mountain pepper (Tasmannia lanceolata) is associated with changes in the leaf chemistry of wild populations from different ecological landscapes and altitudes. The presence of distinct pungent drimane sesquiterpenoid chemotypes was identified: subalpine woodland and wet sclerophyll forest chemotypes. Isolation studies and analysis of extracts revealed that wet sclerophyll forest T. lanceolata populations featured polygodial as the principal terpenoid, with profiles similar to the commercial cultivars sampled. In contrast, the subalpine woodland populations contained the drimane sesquiterpenoids 1ß-acetoxy-9-deoxyisomuzigadial and 3ß-acetoxydrimenin and the conspicuous absence of the pungent principle polygodial.


Assuntos
Compostos Fitoquímicos/química , Extratos Vegetais/química , Winteraceae/química , Altitude , Folhas de Planta/química , Sesquiterpenos/química , Tasmânia , Terpenos/química
5.
Eur J Med Chem ; 185: 111806, 2020 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-31677446

RESUMO

In this work, 35 new derivatives of betulonic, dihydrobetulonic and ursonic acid were prepared including 30 aminothiazoles and all of them were tested for their in vitro cytotoxic activity in eight cancer cell lines and two non-cancer fibroblasts. Compounds with the IC50 below 5 µM in CCRF-CEM cells and low toxicity in non-cancer fibroblasts (4m, 5c, 5m, 6c, 6m, 7b, and 7c) were further subjected to tests of pharmacological parameters yielding the final set for advanced biological evaluation (4m, 5m, 6m, and 7b). It was proved by several methods, that all of them trigger apoptosis via the intrinsic pathway and derivatives 5m and 7b are the most effective (IC50 2.4 µM and 3.6 µM). They are the best candidates to become potentially new anticancer drugs and will be subjected to in vivo tests in mice. In addition, compounds 6b and 6c deserve more attention because their activity is not limited only to chemosensitive CCRF-CEM cell line. Specifically, compound 6b is highly active against K562 leukemic cell line (0.7 µM) and its IC50 activity in colon cancer HCT116 cell line is 1.0 µM. Compound 6c is active in both normal K562 and resistant K562-TAX cell lines (IC50 3.4 µM and 5.4 µM) and both colon cancer cell lines (HCT116 and HCT116p53-/-, IC50 3.5 µM and 3.4 µM).


Assuntos
Antineoplásicos/farmacologia , Ácido Oleanólico/análogos & derivados , Terpenos/farmacologia , Tiazóis/farmacologia , Antineoplásicos/síntese química , Antineoplásicos/química , Apoptose/efeitos dos fármacos , Proliferação de Células/efeitos dos fármacos , Células Cultivadas , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Fibroblastos/efeitos dos fármacos , Humanos , Potencial da Membrana Mitocondrial/efeitos dos fármacos , Microssomos/química , Microssomos/metabolismo , Estrutura Molecular , Ácido Oleanólico/química , Ácido Oleanólico/farmacologia , Relação Estrutura-Atividade , Terpenos/síntese química , Terpenos/química , Tiazóis/síntese química , Tiazóis/química
6.
J Sci Food Agric ; 100(2): 836-845, 2020 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-31646641

RESUMO

BACKGROUND: A classical postulate of viticulture declares that small grape berries produce the best red wines. The popularity of this postulate among winemakers leads them to consider berry size at harvest as a tool to measure the grape's potential to obtain great red wines. To address this issue, two vineyards from the same cultivar and subjected to the same physiological conditions during growing were selected for their difference in average grape berry size at harvest. Grapes from both origins were characterized and used for red winemaking by the same way. Release of volatile compounds and phenolic compounds during the alcoholic fermentation was monitored, and the finished wines were chemically characterized. RESULTS: Larger grapes have a lower theoretical surface-to-volume ratio but have thicker skins and a greater proportion of skins (m/m). Wines made from grapes with a greater proportion of skins contain higher amounts of phenolic compounds, terpenes, volatile acids, acetate esters and polysaccharides. CONCLUSION: According to the results, it seems that grape skin extraction is more related to skin proportion than to berry size. Thus not always smaller grapes produce darker red wines. © 2019 Society of Chemical Industry.


Assuntos
Frutas/química , Vitis/crescimento & desenvolvimento , Vinho/análise , Ésteres , Manipulação de Alimentos , Frutas/crescimento & desenvolvimento , Fenóis/química , Terpenos/química , Vitis/química , Compostos Orgânicos Voláteis/química
7.
Phys Chem Chem Phys ; 21(46): 25658-25668, 2019 Nov 27.
Artigo em Inglês | MEDLINE | ID: mdl-31725143

RESUMO

PrhA from Penicillium brasilianum and AusE from Aspergillus nidulans are nonheme Fe(ii)/α-ketoglutarate-dependent oxygenases, which are involved in the fungal meroterpenoid biosynthetic pathways. Both enzymes use preaustinoid A1 as a common substrate to form divergent products through dynamic skeletal rearrangement. Importantly, structure-guided mutagenesis results in the successful interconversion of AusE and PrhA functions, for example, the PrhA(V150L/A232S) double mutant carried out the same catalysis as AusE. Here, on the basis of the crystal structure of the PrhA (V150L/A232S) double mutant in complex with Fe(ii), αKG and the substrate preaustinoid A1, computational models were constructed, and combined quantum mechanics/molecular mechanics (QM/MM) calculations were performed to illuminate the reaction mechanism at the atomistic level. According to our calculation results, the whole reaction occurs on the quintet state surface. All three steps, including desaturation, ring rearrangement and hydroxylation, require three hydrogen abstractions by FeIV[double bond, length as m-dash]O to trigger the reaction. Owing to the relative position of FeIV[double bond, length as m-dash]O to the hydrogen atoms in the substrate to be extracted, the three H-abstractions correspond to different energy barriers, which are 17.9, 23.6 and 21.8 kcal mol-1, respectively. For the ring rearrangement, as soon as the H5 is extracted, the skeletal rearrangement is very easy. However, in the hydroxylation of intermediate preaustinoid A3, the final O-rebound corresponds to a high barrier, which is mainly caused by the long distance between the Fe-OH and -CH2 radical. It is the relative orientation of the substrate to the highly reactive FeIV[double bond, length as m-dash]O that controls the catalytic chemistry of these enzymes. The reaction barriers are sensitive to the geometry of FeIV[double bond, length as m-dash]OHx (Hx is the hydrogen atom to be extracted). These results may provide useful information for understanding the mechanisms of AusE and PrhA as well as other nonheme Fe(ii)/α-ketoglutarate-dependent oxygenases.


Assuntos
Aspergillus nidulans/química , Vias Biossintéticas , Mutação , Oxigenases/metabolismo , Penicillium/química , Teoria Quântica , Terpenos/metabolismo , Aspergillus nidulans/metabolismo , Biocatálise , Conformação Molecular , Oxigenases/química , Penicillium/metabolismo , Terpenos/química
8.
J Chem Ecol ; 45(11-12): 993-1003, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31755019

RESUMO

Terpenes, volatile plant secondary compounds produced by woody plants, have historically been thought to act as feeding deterrents for mammalian herbivores. However, three species of woodrats, Neotoma stephensi, N. lepida, and N. albigula, regularly consume juniper, which is high in terpenes, and N. stephensi and N. lepida are considered juniper specialists. By investigating the terpene profiles in Juniperus monosperma and J. osteosperma, which are browsed or avoided by woodrats in the field, and recording the caching and consumption of juniper foliage by woodrats in the lab, we have evidence that terpenes may serve as feeding and/or foraging cues. The obligate specialist N. stephensi chose to forage on trees higher in p-cymene and preferred to consume juniper rather than caching it in a laboratory setting. These observations provide evidence that terpenes serve as a feeding cue and that the obligate specialist's physiological mechanism for metabolizing the terpenes present in juniper may negate the need for caching. The facultative specialist N. lepida chose to forage on trees lower in four terpenes and cached more juniper than the obligate specialist N. stephensi, providing evidence that terpenes serve as a feeding deterrent for N. lepida and that this woodrat species relies on behavioral mechanisms to minimize terpene intake. The generalist N. albigula foraged on trees with higher terpenes levels but consumed the least amount of juniper in the lab and preferred to cache juniper rather than consume it, evidence that terpenes act as foraging but not feeding cues in the generalist. Our findings suggest that volatile plant secondary compounds can act as feeding and/or foraging cues and not just feeding deterrents in mammalian herbivores.


Assuntos
Juniperus/química , Terpenos/química , Terpenos/metabolismo , Animais , Peso Corporal , Ingestão de Alimentos/fisiologia , Feminino , Masculino , Avaliação Nutricional , Óleos Voláteis/química , Óleos Voláteis/metabolismo , Extratos Vegetais/química , Extratos Vegetais/metabolismo , Folhas de Planta/química , Coelhos , Roedores/metabolismo , Sigmodontinae/metabolismo , Especificidade da Espécie
9.
J Chem Ecol ; 45(11-12): 934-945, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31755021

RESUMO

The African citrus triozid, Trioza erytreae Del Guercio (Hemiptera: Triozidae) is one of the primary vectors of the bacterium Candidatus Liberibacter spp. which causes citrus greening, a disease of global economic importance in citrus production. Despite its economic importance, little is known about its chemical ecology. Here, we used behavioral assays and chemical analysis to study the chemical basis of interaction between T. erytreae and one of its preferred host plants, Citrus jambhiri. In dual choice Y-tube olfactometer assays, lemon leaf odors attracted females but not males compared to plain air or solvent controls. However, in a petri dish arena assay, both sexes were arrested by lemon leaf odors. Coupled gas chromatography-mass spectrometry (GC/MS) analysis revealed quantitative differences in the odors of flushing and mature leaves, dominated by terpenes. Twenty-six terpenes were identified and quantified. In Petri dish arena assays, synthetic blends of the most abundant terpenes mimicking lemon flushing leaf odors elicited varying behavioral responses from both sexes of T. erytreae. A nine-component blend and a blend of the three most abundant terpenes; limonene, sabinene and ß-ocimene arrested both sexes of T. erytreae. In contrast, a six-component blend lacking in these three components elicited an avoidance response in both sexes. Furthermore, both sexes of T. erytreae preferred the three-component synthetic blend to lemon crude volatile extract. These results suggest that lemon terpenes might be used in the management of T. erytreae.


Assuntos
Citrus/química , Hemípteros/fisiologia , Extratos Vegetais/química , Terpenos/química , Compostos Orgânicos Voláteis/química , Animais , Comportamento Animal , Citrus/parasitologia , Feminino , Cromatografia Gasosa-Espectrometria de Massas/métodos , Especificidade de Hospedeiro , Interações Hospedeiro-Parasita , Insetos Vetores , Masculino , Odorantes , Doenças das Plantas/microbiologia , Extratos Vegetais/metabolismo , Folhas de Planta/química , Folhas de Planta/metabolismo , Terpenos/metabolismo , Compostos Orgânicos Voláteis/metabolismo
10.
Chem Commun (Camb) ; 55(88): 13255-13258, 2019 Oct 31.
Artigo em Inglês | MEDLINE | ID: mdl-31621716

RESUMO

The products of three terpene synthases from two social amoebae, Dictyostelium discoideum and Dictyostelium purpureum, were identified, showing sesquiterpene synthase activity for one and diterpene synthase activity for the other two enzymes. Site-directed mutagenesis experiments revealed the importance of a newly identfied highly conserved residue for catalytic activity. For one of the enzyme products, ß-araneosene, a bromonium ion induced transannular cyclisation was investigated, yielding the first brominated derivatives of this diterpene.


Assuntos
Alquil e Aril Transferases/metabolismo , Dictyostelium/enzimologia , Terpenos/metabolismo , Alquil e Aril Transferases/biossíntese , Biocatálise , Estrutura Molecular , Terpenos/química
11.
Chem Biodivers ; 16(12): e1900289, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31552700

RESUMO

Achillea species and in particular Achillea tenuifolia Lam. is generally used as a food flavor and traditional remedies, especially in the initial developmental stage for medical conditions in the Mediterranean part of Iran. In this report, we extracted the essential oil from the aerial parts of A. tenuifolia (collected from Khoy), at various developmental stages (i. e., vegetative, flowering and fruiting), characterized them and studied their antibacterial activities. Of 46, 51 and 38 components found in the vegetative, flowering, and fruiting stages, respectively, 35 were present in all three stages, including oxygenated terpenes such as carvacrol (30.85-34.11), germacrene C (16.21-17.87), spathulenol (7.26-8.96), ß-sesquiphellandrene (4.11-4.25), τ-muurolol (2.27-3.25) and α-cadinol (2.01-3.29). We witnessed that the composition of the essential oils varies with phenological stages and geographic regions. The essential oil demonstrated substantial antibacterial properties against both Gram-positive and Gram-negative bacteria, indicated by disk method, Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC) assays. Except Pseudomonas aeruginosa, the essential oils of various phenological stages showed higher antibacterial activity against tested bacteria, with Bacillus anthracis as the most sensitive strain. Moreover, although antibacterial characteristics of the essential oil from the vegetative and flowering stages were similar (p=0.91), they were significantly different from those of fruiting stage (p<0.005 in both MIC and MBC tests). This emphasizes the importance of the developmental stage of the plant in the biological properties of its essential oil and justifies the widespread application of this plant in the vegetative stage.


Assuntos
Achillea/química , Antibacterianos/química , Óleos Voláteis/química , Achillea/metabolismo , Antibacterianos/farmacologia , Cromatografia Gasosa-Espectrometria de Massas , Bactérias Gram-Negativas/efeitos dos fármacos , Bactérias Gram-Positivas/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Componentes Aéreos da Planta/química , Componentes Aéreos da Planta/metabolismo , Desenvolvimento Vegetal , Terpenos/química
12.
Eur J Med Chem ; 182: 111652, 2019 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-31494470

RESUMO

Farnesoid X receptor (FXR) is a key regulator in charge of bile acid synthesis, transport, and metabolism. Activation of FXR represses bile acid synthesis and increases its excretion and transport, consequently protecting the liver functions. Thus, FXR is considered as a critical therapeutic target of cholestasis and nonalcoholic steatohepatitis. Herein, we isolated and identified fourteen new protostane-type triterpenoids (1-14) and four known analogues (15-18) from Alisma orientale, and finally constructed a small library of protostane-type triterpenoids (1-70) to investigate their structure-activity relationship with FXR, further leading to obtain compound 15 with potent agonistic activity against FXR (EC50 = 90 nM). Extensive in vitro investigation confirmed high efficacy of compound 15 against FXR in living cell, and revealed its underlying mechanism for FXR activation (amino acid residues Arg331 and Ser332) by molecular docking and site-directed mutagenesis technology.


Assuntos
Produtos Biológicos/farmacologia , Receptores Citoplasmáticos e Nucleares/agonistas , Terpenos/farmacologia , Alisma/química , Produtos Biológicos/química , Produtos Biológicos/isolamento & purificação , Células Cultivadas , Relação Dose-Resposta a Droga , Células Hep G2 , Humanos , Simulação de Acoplamento Molecular , Estrutura Molecular , Mutagênese Sítio-Dirigida , Receptores Citoplasmáticos e Nucleares/genética , Relação Estrutura-Atividade , Terpenos/química , Terpenos/isolamento & purificação
13.
Mar Drugs ; 17(9)2019 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-31480497

RESUMO

: An Antarctic coral belonging to the order Pennatulacea, collected during the 2013 austral autumn by trawl from 662 to 944 m depth, has yielded three new briarane diterpenes, bathyptilone A-C (1-3) along with a trinorditerpene, enbepeanone A (4), which bears a new carbon skeleton. Structure elucidation was facilitated by one- and two-dimensional NMR spectroscopy, mass spectrometry and confirmed by X-ray crystallography. The three compounds were screened in four cancer cell lines. Bathyptilone A displayed selective nanomolar cytotoxicity against the neurogenic mammalian cell line Ntera-2.


Assuntos
Antozoários/química , Terpenos/química , Animais , Regiões Antárticas , Cristalografia por Raios X/métodos , Diterpenos/química , Células HeLa , Humanos , Espectroscopia de Ressonância Magnética/métodos , Espectrometria de Massas/métodos
14.
J Chem Ecol ; 45(10): 888-900, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31493165

RESUMO

Interactions between water stress and induced defenses and their role in tree mortality due to bark beetles are poorly understood. We performed a factorial experiment on 48 mature ponderosa pines (Pinus ponderosa) in northern Arizona over three years that manipulated a) tree water stress by cutting roots and removing snow; b) bark beetle attacks by using pheromone lures; and c) phloem exposure to biota vectored by bark beetles by inoculating with dead beetles. Tree responses included resin flow from stem wounds, phloem composition of mono- and sesqui-terpenes, xylem water potential, leaf gas exchange, and survival. Phloem contained 21 mono- and sesqui-terpenes, which were dominated by (+)-α-pinene, (-)-limonene, and δ-3-carene. Bark beetle attacks (mostly Dendroctonus brevicomis) and biota carried by beetles induced a general increase in concentration of phloem mono- and sesqui-terpenes, whereas water stress did not. Bark beetle attacks induced an increase in resin flow for unstressed trees but not water-stressed trees. Mortality was highest for beetle-attacked water-stressed trees. Death of beetle-attacked trees was preceded by low resin flow, symptoms of water stress (low xylem water potential, leaf gas exchange), and an ephemeral increase in concentrations of mono- and sesqui-terpenes compared to surviving trees. These results show a) that ponderosa pine can undergo induction of both resin flow and phloem terpenes in response to bark beetle attack, and that the former is more constrained by water stress; b) experimental evidence that water stress predisposes ponderosa pines to mortality from bark beetles.


Assuntos
Besouros/fisiologia , Secas , Interações Hospedeiro-Parasita/efeitos dos fármacos , Pinus ponderosa/química , Terpenos/farmacologia , Animais , Cromatografia Gasosa , Pinus ponderosa/metabolismo , Casca de Planta/química , Casca de Planta/metabolismo , Resinas Vegetais/química , Resinas Vegetais/metabolismo , Estações do Ano , Terpenos/análise , Terpenos/química
15.
Bol. latinoam. Caribe plantas med. aromát ; 18(5): 444-458, sept. 2019. ilus, tab
Artigo em Inglês | LILACS | ID: biblio-1008263

RESUMO

This review work focuses on how the secondary chemistry could help in the survival of plants in high mountain habitats under extreme environmental conditions. The elevated levels of stress in high areas of the tropic and subtropic change dramatically not only by following the annual cycles of winter and summer but they also change in a single day. Some species, however, are able to successfully grow at heights more than 3000 m in the tropical mountains due, in part, to highly specialized physiological processes that affect their physical and chemical responses. In this study, it describes some strategies of how the secondary metabolites could help the plants to stand the high levels of stress in the high mountain ecosystems.


Este trabajo de revisión se centra en cómo la química secundaria podría ayudar en la supervivencia de plantas en hábitats de alta montaña en condiciones ambientales extremas. Los altos niveles de estrés en las zonas altas del trópico y subtrópico cambian dramáticamente no solo al seguir los ciclos anuales de invierno y verano, sino que también cambian en un solo día. Sin embargo, algunas especies pueden crecer con éxito a alturas superiores a 3000 m en las montañas tropicales debido, en parte, a procesos fisiológicos altamente especializados que afectan sus respuestas físicas y químicas. En esta revisión, se describen algunas estrategias de cómo los metabolitos secundarios podrían ayudan a las plantas a soportar los altos niveles de estrés en los ecosistemas de alta montaña.


Assuntos
Plantas/química , Estresse Fisiológico , Óleos Voláteis/química , Altitude , Floroglucinol/análise , Floroglucinol/química , Terpenos/análise , Terpenos/química , Flavonoides/análise , Flavonoides/química
16.
Chem Biodivers ; 16(9): e1900366, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31386266

RESUMO

The natural polyisoprenylated benzophenone derivatives garcinol and isogarcinol are secondary plant metabolites isolated from various Garcinia species including Garcinia indica. This review takes stock of the recent chemical and biological research into these interesting natural compounds over the last five years. New biological sources and chemical syntheses are discussed followed by new insights into the activity of garcinol and isogarcinol against cancer, pathogenic bacteria, parasite infections and various inflammatory diseases.


Assuntos
Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/farmacologia , Antiprotozoários/farmacologia , Neoplasias/tratamento farmacológico , Terpenos/farmacologia , Animais , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antiprotozoários/química , Antiprotozoários/isolamento & purificação , Garcinia/química , Humanos , Terpenos/química , Terpenos/isolamento & purificação
17.
Molecules ; 24(16)2019 Aug 10.
Artigo em Inglês | MEDLINE | ID: mdl-31405117

RESUMO

Two new terpene glycosides (1-2) along with two known analogs (3-4) were obtained from the root of Sanguisorba officinalis, which is a common traditional Chinese medicine (TCM). Their structures were elucidated by nuclear magnetic resonance (NMR), electrospray ionization high resolution mass spectrometry (HRESIMS), and a hydrolysis reaction, as well as comparison of these data with the literature data. Compounds 1-4 exhibited anti-inflammatory properties in vitro by attenuating the production of inflammatory mediators, such as nitric oxide (NO) as well as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6). An anti-inflammatory assay based on the zebrafish experimental platform indicated that compound 1 had good anti-inflammatory activity in vivo by not only regulating the distribution, but also by reducing the amount of the macrophages of the zebrafish exposed to copper sulfate.


Assuntos
Anti-Inflamatórios , Glicosídeos , Sanguisorba/química , Terpenos , Animais , Anti-Inflamatórios/química , Anti-Inflamatórios/isolamento & purificação , Anti-Inflamatórios/farmacologia , Glicosídeos/química , Glicosídeos/isolamento & purificação , Glicosídeos/farmacologia , Inflamação/tratamento farmacológico , Inflamação/metabolismo , Inflamação/patologia , Interleucina-6/metabolismo , Camundongos , Óxido Nítrico/metabolismo , Células RAW 264.7 , Terpenos/química , Terpenos/isolamento & purificação , Terpenos/farmacologia , Fator de Necrose Tumoral alfa/metabolismo , Peixe-Zebra
18.
Molecules ; 24(15)2019 Jul 31.
Artigo em Inglês | MEDLINE | ID: mdl-31370240

RESUMO

Arabidopsis roots accumulate a complex mixture of dolichols composed of three families, (i.e., short-, medium- and long-chain dolichols), but until now none of the cis-prenyltransferases (CPTs) predicted in the Arabidopsis genome has been considered responsible for their synthesis. In this report, using homo- and heterologous (yeast and tobacco) models, we have characterized the AtCPT1 gene (At2g23410) which encodes a CPT responsible for the formation of long-chain dolichols, Dol-18 to -23, with Dol-21 dominating, in Arabidopsis. The content of these dolichols was significantly reduced in AtCPT1 T-DNA insertion mutant lines and highly increased in AtCPT1-overexpressing plants. Similar to the majority of eukaryotic CPTs, AtCPT1 is localized to the endoplasmic reticulum (ER). Functional complementation tests using yeast rer2Δ or srt1Δ mutants devoid of medium- or long-chain dolichols, respectively, confirmed that this enzyme synthesizes long-chain dolichols, although the dolichol chains thus formed are somewhat shorter than those synthesized in planta. Moreover, AtCPT1 acts as a homomeric CPT and does not need LEW1 for its activity. AtCPT1 is the first plant CPT producing long-chain polyisoprenoids that does not form a complex with the NgBR/NUS1 homologue.


Assuntos
Arabidopsis/enzimologia , Raízes de Plantas/enzimologia , Terpenos/química , Transferases/química , Arabidopsis/genética , /genética , Retículo Endoplasmático , Genoma de Planta/genética , Raízes de Plantas/genética , Transferases/genética
19.
J Agric Food Chem ; 67(36): 10273-10284, 2019 Sep 11.
Artigo em Inglês | MEDLINE | ID: mdl-31418566

RESUMO

Shiraz wine volatomes from two Australian geographical indications (GIs), that is, Orange and Riverina, were compared using comprehensive two-dimensional gas chromatography coupled to time-of-flight mass spectrometry. Shiraz wines were made in triplicate from grapes harvested at two harvest dates from six vineyards in the two GIs. A total of 133 compounds showed a significant trend between wines from the cooler Orange GI and warmer Riverina. Compounds associated with wines from the cooler climate were grape-derived volatiles, such as monoterpenes, sesquiterpenes, green leaf volatiles, and some norisoprenoids. Fermentation-derived compounds, such as esters and S-containing compounds, showed no specific trend related to grape origin. In addition, wines could be also clearly separated according to the harvest date, irrespective of the climate, with C6 compounds, higher alcohol acetates, and other esters contributing utmost to the differentiation of samples, whereas terpenoids and norisoprenoids did not have an influence. This study demonstrated the plasticity of wine volatome related to grape origin and also the maturity level (harvest date), irrespective of climate.


Assuntos
Cromatografia Gasosa-Espectrometria de Massas/métodos , Vitis/química , Compostos Orgânicos Voláteis/química , Vinho/análise , Austrália , Clima , Análise Discriminante , Frutas/química , Odorantes/análise , Terpenos/química
20.
Molecules ; 24(17)2019 Aug 21.
Artigo em Inglês | MEDLINE | ID: mdl-31438523

RESUMO

In the present study we aimed to investigate the volatile organic compounds (VOCs) that may potentially be responsible for specific descriptors of Madeira wine providing details about Madeira wine aroma notes at molecular level. Moreover, the wine aroma profile, based on the obtained data, will be a starting point to evaluate the impact of grape variety (Malvasia, Bual, Sercial, Verdelho and Tinta Negra), type (sweet, medium sweet, dry and medium dry), and age (from 3 to 20 years old) on Madeira wine sensorial properties. Firstly, a comprehensive and in-depth Madeira wine volatile profiling was carried out using headspace solid-phase microextraction combined with gas chromatography-mass spectrometry (HS-SPME/GC-qMS). Secondly, a relation among the varietal, fermentative and aging aroma compounds, and their aroma descriptors with the Madeira wine sensorial properties was assessed. A total of 82 VOCs, belonging to different chemical families were identified, namely 21 esters, 13 higher alcohols, ten terpenic compounds, nine fatty acids, seven furanic compounds, seven norisoprenoids, six lactones, four acetals, four volatile phenols and one sulphur compound. From a sensorial point of view, during the aging process the wine lost its freshness and fruitiness odor related to the presence of some varietal and fermentative compounds, whereas other descriptors such as caramel, dried fruits, spicy, toasty and woody, arose during ageing. The Maillard reaction and diffusion from the oak were the most important pathways related with these descriptors. A relationship-based approach was used to explore the impact of grape variety, wine type, and age on Madeira wine sensorial properties based on shared number of VOCs and their odors.


Assuntos
Odorantes/análise , Vinho , Acetais/química , Álcoois/química , Ácidos Graxos/química , Cromatografia Gasosa-Espectrometria de Massas , Lactonas/química , Microextração em Fase Sólida , Terpenos/química , Vitis/química , Compostos Orgânicos Voláteis/análise
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