Your browser doesn't support javascript.
loading
Mostrar: 20 | 50 | 100
Resultados 1 - 20 de 558
Filtrar
Mais filtros










Filtros aplicados
Base de dados
Intervalo de ano de publicação
1.
J Agric Food Chem ; 68(6): 1684-1690, 2020 Feb 12.
Artigo em Inglês | MEDLINE | ID: mdl-31957431

RESUMO

The carotenoid-derived volatile ß-ionone plays an important role in the formation of green and black tea flavors due to its low odor threshold, but its formation and the gene(s) involved in its biosynthesis during the tea withering process is(are) still unknown. In this study, we found that the content of ß-ionone increased during the tea withering process catalyzed by an unknown enzyme(s). Correlation analysis of expression patterns of Camellia sinensis carotenoid cleavage dioxygenase genes (CsCCDs) and the ß-ionone content during the withering period revealed CsCCD4 as the most promising candidate. The full-length CsCCD4 gene was amplified from C. sinensis, and the biochemical function of the recombinant CsCCD4 protein was studied after coexpression in Escherichia coli strains engineered to accumulate ß-carotene. The recombinant protein was able to cleave a variety of carotenoids at the 9-10 and 9'-10' double bonds. Volatile ß-ionone was detected as the main product by gas and liquid chromatography-mass spectrometry. The accumulation of ß-ionone was consistent with the expression levels of CsCCD4 in different tissues and during the withering process. The CsCCD4 expression was induced by low temperature and mechanical damage stress but not by dehydration stress. The results demonstrate that CsCCD4 catalyzes the production of ß-ionone in the tea plant and provide insight into its formation mechanism during the withering process.


Assuntos
Camellia sinensis/enzimologia , Carotenoides/metabolismo , Dioxigenases/metabolismo , Norisoprenoides/metabolismo , Proteínas de Plantas/metabolismo , Sequência de Aminoácidos , Biocatálise , Camellia sinensis/química , Camellia sinensis/genética , Camellia sinensis/metabolismo , Dioxigenases/genética , Manipulação de Alimentos , Espectrometria de Massas , Filogenia , Folhas de Planta/química , Folhas de Planta/enzimologia , Folhas de Planta/metabolismo , Proteínas de Plantas/genética , Plantas/classificação , Plantas/enzimologia , Plantas/genética , Alinhamento de Sequência
2.
Carbohydr Polym ; 231: 115733, 2020 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-31888823

RESUMO

All-trans retinoic acid (ATRA) was grafted to hyaluronan (HA) via esterification. The reaction was mediated by mixed anhydrides. A perfect control of the degree of substitution (0.5-7.5%) was obtained by varying the molar ratio of retinoic acid in the feed. The degree of substitution plays a significant role in the long-term stability. The photodegradation of HA-ATRA upon UVA irradiation resulted in ß-ionone, ß-cyclocitral and 5,6-epoxy-(E)-retinoic acid. The photostability of the conjugate had increased with the combination with morin. The chemical structure of HA-ATRA and its degradation products was elucidated using NMR spectroscopy, SEC-MALLS, and gas chromatography-mass spectrometry (GC-MS). ATRA did not loss its biological activity after conjugation, as demonstrated by gene expression. The derivative was able to penetrate across the stratum corneum. Besides, HA-ATRA downregulated the expression of anti-inflammatory interleukins 6 and 8. HA-ATRA would be expected to be used for transdermal drug delivery or cosmetics.


Assuntos
Antioxidantes/farmacologia , Ácido Hialurônico/química , Pele/efeitos dos fármacos , Tretinoína/química , Administração Cutânea , Anidridos/química , Animais , Antioxidantes/química , Esterificação , Flavonoides/química , Ácido Hialurônico/síntese química , Ácido Hialurônico/farmacologia , Camundongos , Células NIH 3T3 , Norisoprenoides/química , Norisoprenoides/farmacologia , Fotólise/efeitos dos fármacos , Pele/efeitos da radiação , Tretinoína/síntese química , Tretinoína/farmacologia , Raios Ultravioleta
3.
Food Chem ; 306: 125623, 2020 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-31606633

RESUMO

In this study, apple juice was fermented using Hanseniaspora osmophila X25-5 in pure culture as well as mixed culture with Torulaspora quercuum X24-4, which was inoculated simultaneously or sequentially. H. osmophila inhibited the growth of T. quercuum, while T. quercuum had little effect on the growth of H. osmophila. The simultaneous fermentation consumed relatively more sugar and resulted in the highest ethanol content. The production of organic acids varied depending on the yeast species employed and inoculation modality. Esters and alcohols were the main volatile families produced during fermentation, while ethyl esters and terpenes contributed most to the temperate fruity aroma. Gas chromatography-olfactometry (GC-O) showed that 3-methyl-1-butanol, ethyl 2-methylbutanoate, phenylethyl alcohol, ß-phenethyl acetate, and ß-damascenone were the most potent odorants in all samples. This study suggested that simultaneous fermentation with H. osmophila and T. quercuum might represent a novel strategy for the future production of cider.


Assuntos
Acetatos/análise , Fermentação , Hanseniaspora/metabolismo , Malus/metabolismo , Odorantes/análise , Torulaspora/metabolismo , Bebidas Alcoólicas , Cromatografia Gasosa , Ésteres/análise , Frutas/química , Norisoprenoides/análise , Olfatometria , Vinho/análise
4.
Chem Pharm Bull (Tokyo) ; 67(12): 1337-1346, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31787660

RESUMO

The 1-BuOH-soluble fraction of the methanol (MeOH) extract of Diospyros maritima was separated by chromatographic techniques to give three new oleanane-type and one new ursane-type triterpene glucoside, named ebenamariosides A-D (1-4); two megastigmanes were also isolated. The structures of triterpene glucosides was elucidated with extensive investigation by one and two dimensional NMR spectroscopy and the structures were confirmed by partial enzymatic hydrolyses to give the corresponding mono-glucosides and aglycones. The structures of the megastigmanes, including their absolute stereochemistries, were elucidated by spectroscopic evidence and by the modified Mosher's method. Two megastigmanes were chemically correlated and their absolute structures were unambiguously determined. The cytotoxicity of the triterpene glucosides and their degradation products were assayed. They did not show any significant activity.


Assuntos
Diospyros/química , Glucosídeos/isolamento & purificação , Norisoprenoides/isolamento & purificação , Folhas de Planta/química , Triterpenos/isolamento & purificação , Células A549 , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Glucosídeos/química , Glucosídeos/farmacologia , Humanos , Conformação Molecular , Norisoprenoides/química , Norisoprenoides/farmacologia , Estereoisomerismo , Relação Estrutura-Atividade , Triterpenos/química , Triterpenos/farmacologia
5.
Molecules ; 25(1)2019 Dec 19.
Artigo em Inglês | MEDLINE | ID: mdl-31861560

RESUMO

Apocarotenoids, such as ß-cyclocitral, α-ionone, ß-ionone, and loliolide, are derived from carotenes via chemical or enzymatic processes. Recent studies revealed that ß-cyclocitral and loliolide play an important role in various aspects of plant physiology, such as stress responses, plant growth, and herbivore resistance. However, information on the physiological role of α-ionone is limited. We herein investigated the effects of α-ionone on plant protection against herbivore attacks. The pretreatment of whole tomato (Solanum lycopersicum) plants with α-ionone vapor decreased the survival rate of western flower thrips (Frankliniella occidentalis) without exhibiting insecticidal activity. Exogenous α-ionone enhanced the expression of defense-related genes, such as basic ß-1,3-glucanase and basic chitinase genes, in tomato leaves, but not that of jasmonic acid (JA)- or loliolide-responsive genes. The pretreatment with α-ionone markedly decreased egg deposition by western flower thrips in the JA-insensitive Arabidopsis (Arabidopsis thaliana) mutant coi1-1. We also found that common cutworm (Spodoptera litura) larvae fed on α-ionone-treated tomato plants exhibited a reduction in weight. These results suggest that α-ionone induces plant resistance to western flower thrips through a different mode of action from that of JA and loliolide.


Assuntos
Resistência à Doença , Lycopersicon esculentum/efeitos dos fármacos , Norisoprenoides/farmacologia , Tisanópteros/efeitos dos fármacos , Animais , Arabidopsis/efeitos dos fármacos , Arabidopsis/genética , Arabidopsis/parasitologia , Ciclopentanos/metabolismo , Feminino , Flores/efeitos dos fármacos , Flores/parasitologia , Regulação da Expressão Gênica de Plantas/efeitos dos fármacos , Lycopersicon esculentum/genética , Lycopersicon esculentum/parasitologia , Oxilipinas/metabolismo , Doenças das Plantas/genética , Doenças das Plantas/parasitologia , Doenças das Plantas/prevenção & controle , Proteínas de Plantas/genética
6.
Fitoterapia ; 139: 104408, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31698058

RESUMO

One new pseudoguaianolide (1), one new megastigmane (6), and one new ent-abietane diterpene (9), together with seven known compounds (2-5, 7, 8, and 10) were isolated from the aerial parts of Euphorbia thymifolia. The structures of the new compounds and their relative configurations were determined by spectroscopic data analysis. The absolute configurations of compounds 1, 6, and 9 were determined by single-crystal X-ray crystallographic analysis, modified Mosher's method and calculated ECD experiment, respectively. All compounds were tested for their inhibitory effects against LPS-induced NO production in BV-2 microglial cells, and pseudoguaianolides (1-5) showed significant activity with IC50 values of 0.41-15.32 µM.


Assuntos
Diterpenos/farmacologia , Euphorbia/química , Fármacos Neuroprotetores/farmacologia , Sesquiterpenos/farmacologia , Abietanos , Animais , Linhagem Celular Tumoral , China , Cicloexanonas , Diterpenos/isolamento & purificação , Glucosídeos , Camundongos , Microglia/efeitos dos fármacos , Estrutura Molecular , Fármacos Neuroprotetores/isolamento & purificação , Óxido Nítrico , Norisoprenoides , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Componentes Aéreos da Planta/química , Sesquiterpenos/isolamento & purificação
7.
Environ Sci Pollut Res Int ; 26(33): 34510-34520, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31643015

RESUMO

The odor problem caused by the decay of aquatic plants is widespread in many freshwater lakes. In this study, the spatial distributions of seven taste and odor (T&O) compounds (dimethyl sulfide, dimethyl disulfide, dimethyl trisulfide, 2-methylisoborneol, geosmin, ß-cyclocitral, and ß-ionone) in the sediments and overlying water of the east of Taihu Lake were investigated. The effects of plant and physico-chemical parameters on the release of T&O compounds were also analyzed. The results showed that high concentrations of T&O compounds were detected in the area where Eichhornia crassipes was flourishing. Volatile organic sulfur compounds were not found in the water source area, which was not covered by aquatic plants. High plant biomass and aquiculture activities might increase the release of the taste and odor compounds. The correlation between the concentrations of odorous compounds and nutrients in the sediment was also analyzed. The production of odorants was positively correlated with the nitrogen, and they may migrate from sediment to overlying water. The result suggested that controlling the plant density and aquaculture activities could reduce the release of odorous compounds.


Assuntos
Organismos Aquáticos/química , Odorantes/análise , Plantas/química , Paladar , Aldeídos , Canfanos , China , Diterpenos , Sedimentos Geológicos/química , Lagos/química , Naftóis , Norisoprenoides , Sulfetos , Compostos Orgânicos Voláteis , Poluentes Químicos da Água/análise
8.
Molecules ; 24(19)2019 Sep 23.
Artigo em Inglês | MEDLINE | ID: mdl-31547525

RESUMO

Tobacco (Nicotiana tabacum L.) aroma is an important attribute of tobacco quality and is influenced by a variety of minor chemical components, including carotenoid degradation products. The objectives of this work were to determine the content of the most important fragrance-shaping carotenoid degradation products in the essential oils (EOs) of the three types of Bulgarian tobacco-Oriental (OR), flue-cured Virginia (FCV), and Burley (BU)-and to compare them with other aromatic products from tobacco. The content of total carotenoids and ß-carotene was highest in BU tobacco (22.23 and 20.34 mg/100 g DW, respectively), followed by OR (13.60 and 12.09 mg/100 g DW in variety "Plovdiv 7" (Pd7); 6.27 and 5.45 mg/100 g DW in "Krumovgrad" (Kr), and FCV (5.93 and 3.73 mg/100 g DW). EOs were obtained by hydrodistillation in an acidified medium, and the main aroma-impact compounds from carotenoid degradation (identified by GC-MS) were as follows: FCV-α-ionone (0.61 mg/100 g DW), dihydro-ß-ionone (0.96 mg/100 g DW), ß-damascenone (1.26 mg/100 g DW); BU-α-ionone (0.73 mg/100 g DW), dihydro-ß-ionone (1.19 mg/100 g DW), ß-damascenone (1.35 mg/100 g DW); OR(Kr)-α-ionone (0.20 mg/100 g DW), ß-ionone (1.08 mg/100 g DW), dihydro-ß-ionone (1.34 mg/100 g DW), ß-damascenone (0.36 mg/100 g DW); OR(Pd7)-α-ionone (1.43 mg/100 g DW), dihydro-ß-ionone (1.73 mg/100 g DW), ß-damascenone (1.23 mg/100 g DW). Ionone and its derivatives were not identified in the aroma extraction products concrete, resinoid, or absolute. The results suggest that temperature, pH of the medium, process duration, and possibly other unknown factors affect carotenoid transformation. The study provides insight into the composition of tobacco EOs and may be of interest to the fragrance industry.


Assuntos
Carotenoides/química , Óleos Voláteis/química , Tabaco/química , Cromatografia Gasosa-Espectrometria de Massas , Norisoprenoides/química
9.
J Chem Ecol ; 45(10): 849-857, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31512099

RESUMO

Odorant binding proteins (OBPs) play a key role in chemoreception in insects. In an earlier study, we identified CmedOBP14 from the rice leaf folder, Cnaphalocrocis medinalis, with potential physiological functions in olfaction. Here, we performed a competitive binding assay under different pH conditions as well as knockdown via RNA interference to determine the specific role of CmedOBP14 in C. medinalis. CmedOBP14 displayed broad binding affinities to many host-related compounds, with higher affinities at pH 7.4 compared with pH 5.0. After treatment with CmedOBP14-dsRNA, the transcript level of OBP14 was significantly decreased at 72 h compared with controls, and the electroantennogram response evoked by nerolidol, L-limonene and beta-ionone was reduced. Furthermore, behavioral assays revealed consistent patterns among these compounds, especially for nerolidol, with adults could no longer able to differentiate 0.1% nerolidol from controls. RNAi experiments suggest that at least in part, CmedOBP14 mediates the ability to smell nerolidol and beta-ionone.


Assuntos
Proteínas de Insetos/metabolismo , Mariposas/metabolismo , Receptores Odorantes/metabolismo , Animais , Antenas de Artrópodes/metabolismo , Comportamento Animal/efeitos dos fármacos , Ligação Competitiva , Fenômenos Eletrofisiológicos/efeitos dos fármacos , Concentração de Íons de Hidrogênio , Proteínas de Insetos/antagonistas & inibidores , Proteínas de Insetos/genética , Norisoprenoides/farmacologia , Interferência de RNA , RNA de Cadeia Dupla/metabolismo , Receptores Odorantes/antagonistas & inibidores , Receptores Odorantes/genética , Sesquiterpenos/farmacologia
10.
Molecules ; 24(16)2019 Aug 16.
Artigo em Inglês | MEDLINE | ID: mdl-31426361

RESUMO

Key odorants of red wine made from the hybrid grapes of Marselan (Vitis vinifera L.) were isolated by solid-phase extraction (SPE) and explored by gas chromatography-olfactometry (GC-O) analysis. Application of aroma extract dilution analysis (AEDA) revealed 43 odor-active compounds, and 31 odorants among them were detected with flavor dilution (FD) factors ranging from 9 to 2187. Comprehensive two-dimensional gas chromatography and time-of-flight mass spectrometry (GC × GC-TOF-MS) were exploited to quantitate the aroma-active compounds with FD ≥9. The identification indicated ß-damascenone as having the highest FD factors, followed by eugenol, 2,3-butanedione, citronellol, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, phenethyl acetate, guaiacol, and 2-methoxy-4-vinylphenol. A total of 21 compounds were found to have odor activity values (OAVs) >1.0. Aroma reconstitution validation experiments showed a good similarity of blackberry, green pepper, honey, raspberry, caramel, smoky, and cinnamon aroma attributes between the original Marselan wine and the reconstructed wine. In addition, omission tests were carried out to further determine the contribution of odorants to the overall aroma.


Assuntos
Odorantes/análise , Olfato/fisiologia , Vitis/química , Compostos Orgânicos Voláteis/isolamento & purificação , Vinho/análise , Monoterpenos Acíclicos/isolamento & purificação , Diacetil/isolamento & purificação , Eugenol/isolamento & purificação , Feminino , Furanos/isolamento & purificação , Cromatografia Gasosa-Espectrometria de Massas , Guaiacol/análogos & derivados , Guaiacol/isolamento & purificação , Humanos , Masculino , Norisoprenoides/isolamento & purificação , Olfatometria/instrumentação , Olfatometria/métodos , Extração em Fase Sólida/métodos , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz , Paladar/fisiologia , Compostos de Vinila/isolamento & purificação , Compostos Orgânicos Voláteis/classificação
11.
Environ Pollut ; 254(Pt A): 112954, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31398637

RESUMO

Organic matter-induced black bloom frequently occurs in a number of large eutrophic shallow lakes; this can result in the release of malodorous compounds and has a negative impact on water quality. In the study, a microcosm system containing Zizania latifolia (Z. latifolia), a common aquatic plant, was established and the release of seven taste and odour compounds, dimethyl sulphide (DMS), dimethyl disulphide (DMDS), dimethyl trisulphide (DMTS), 2-methylisoborneol (MIB), geosmin (GSM), ß-cyclocitral, and ß-ionone, was investigated. The results showed that these compounds were all detected during Z. latifolia decay, and that volatile organic sulphur compounds (VOSCs), such as DMS, DMDS, and DMTS, were the main factors responsible for the strong foul odour (the maximum reached 5.0 µg L-1). The release of odorous compounds was stronger during the initial seven days, and then progressively decreased in the middle stage of the experiment. Furthermore, large amounts of nutrients were released into the overlying water; nutrient concentration increased with increasing plant biomass. A positive correlation was observed between the odorant concentration and plant biomass. These results indicate that the density of aquatic plants should be controlled as part of future management of aquatic ecosystems.


Assuntos
Biodegradação Ambiental , Ecossistema , Odorantes/análise , Poaceae , Aldeídos , Canfanos , Diterpenos , Lagos , Naftóis , Norisoprenoides , Sulfetos , Paladar , Compostos Orgânicos Voláteis , Qualidade da Água
12.
Pharmazie ; 74(7): 443-446, 2019 07 01.
Artigo em Inglês | MEDLINE | ID: mdl-31288903

RESUMO

The pharmacist and chemist Ferdinand Tiemann (1848-1899) having succeeded in the synthesis of vanillin, is considered to be the father of Geschmackstoff-Chemie (flavor chemistry). Tiemann, together with Paul Krüger (1859-1916) and then with Friedrich-Wilhelm Semmler (1860-1931), developed a method to obtain with a good yield Veilchenduft (violet scent); they condensed citral with di-methyl-ketone (acetone) thus generating an intermediate which upon exposure to an acidic environment cyclizes to ionone. By doing so the fragrance chemistry was born. Ionone (the compound responsible for the violet scent) was produced on an industrial scale at the factory of Wilhelm Haarmann (1847-1931) in Holzminden, factory renamed 1876 Haarmann & Reimer, after Karl Reimer (1845-1881) joined the group of owners. While a number of chemists and pharmacists were involved in the synthesis of Ionone (Veilchenduft; violet scent) and irone (iris scent), with few exceptions, their biographies are pretty well documented. In contrast, very little transpired about Dr. Paul Krüger, who spent some seven years trying to iron out the difficulties of ionone synthesis. The purpose of this short contribution is to shed some light on the life and work of Paul Krüger while providing an overview on the status of ionone pharmacology and to highlight the historical significance of ionone synthesis.


Assuntos
Norisoprenoides/história , Odorantes/análise , História do Século XIX , História do Século XX , Humanos , Norisoprenoides/síntese química , Norisoprenoides/farmacologia , Perfumes/história , Receptores Odorantes/história
13.
Fitoterapia ; 137: 104265, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31302252

RESUMO

The aromatic plants of Vitex negundo var. heterophylla are not only herb medicine but also a functional food and an industrial crop. Its leaves can be used as a functional food for improving human's health, but the previous studies mainly focused on the volatile constituents, lignans, and iridoids. Our research led to the isolation of four new terpenoids (1-4), together with fifteen known compounds including seven flavonoids (9-15), two jasmonates (7-8) and six terpenoids (5-6, 16-19) from the leaves. Among all these compounds, 1, 2, 11, and 19 exhibited strong inhibitory activity against NO production in lipopolysaccharide (LPS)-induced RAW264.7 macrophage. The anti-inflammatory mechanism of the most active compound (2) is related to the inhibition of iNOS and COX-2, and the suppression of NF-κB pathway. Therefore, terpenoids and flavonoids from the leaves of Vitex negundo var. heterophylla might be used as potential anti-inflammatory candidates for developing medicine or value-added functional food.


Assuntos
Anti-Inflamatórios/farmacologia , Diterpenos/farmacologia , Norisoprenoides/farmacologia , Vitex/química , Animais , Anti-Inflamatórios/isolamento & purificação , China , Ciclo-Oxigenase 2/metabolismo , Diterpenos/isolamento & purificação , Interleucinas/metabolismo , Camundongos , Estrutura Molecular , Óxido Nítrico Sintase Tipo II/metabolismo , Norisoprenoides/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Células RAW 264.7
14.
Food Chem ; 299: 125089, 2019 Nov 30.
Artigo em Inglês | MEDLINE | ID: mdl-31319343

RESUMO

Synthesis of ß-ionone in recombinant Saccharomyces cerevisiae is limited by the efficiency of Carotenoid Cleavage Dioxygenases (CCD), membrane-tethered enzymes catalyzing the last step in the pathway. We performed in silico design and membrane affinity analysis, focused on single-point mutations of PhCCD1 to improve membrane anchoring. The resulting constructs were tested in a ß-carotene hyper-producing strain by comparing colony pigmentation against colonies transformed with native PhCCD1 and further analyzed by ß-ionone quantification via RP-HPLC. Two single-point mutants increased ß-ionone yields almost 3-fold when compared to native PhCCD1. We also aimed to improve substrate accessibility of PhCCD1 through the amino-terminal addition of membrane destination peptides directed towards the endoplasmic reticulum or plasma membrane. Yeast strains expressing peptide-PhCCD1 constructs showed ß-ionone yields up to 4-fold higher than the strain carrying the native enzyme. Our results demonstrate that protein engineering of CCDs significantly increases the yield of ß-ionone synthesized by metabolically engineered yeast.


Assuntos
Carotenoides/metabolismo , Dioxigenases/genética , Dioxigenases/metabolismo , Norisoprenoides/biossíntese , Engenharia de Proteínas , Saccharomyces cerevisiae/metabolismo , Engenharia Metabólica , Saccharomyces cerevisiae/citologia , Saccharomyces cerevisiae/genética
15.
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
17.
Chem Biol Interact ; 308: 377-384, 2019 Aug 01.
Artigo em Inglês | MEDLINE | ID: mdl-31150631

RESUMO

Among the primary neoplasias that affect the liver, hepatocellular carcinoma (HCC) is the most frequent and the third leading cause of death related to cancer. Several risk factors predispose individuals to HCC such as nonalcoholic fatty liver disease (NAFLD), whose incidence has significantly increased worldwide. ß-ionone (ßI) isoprenoid is a known chemopreventive of hepatocarcinogenesis. However, the effects of this compound on NAFLD isolated or in association with hepatocarcinogenesis have not yet been evaluated. A high-fat emulsion administered for 6 weeks resulted in NAFLD in male rats, and oral treatment with ßI during this period significantly attenuated its development. Moreover, the presence of NAFLD potentiated hepatocarcinogenesis induced by the resistant hepatocyte (RH) model in these animals by increasing the number and percentage of the liver section area occupied by placental glutathione S-transferase (GST-P)-positive persistent preneoplastic lesions (pPNLs), that are thought to evolve into HCC. This indicates that this NAFLD/RH protocol is suitable for studies of the influence of NAFLD on the HCC development. Therefore, here we also investigated the chemopreventive effect of ßI under these two associated conditions. In this context, ßI reduced the number and percentage of the liver section area occupied by pPNLs, as well as cell proliferation and the number of oval cells, which are considered potential targets for the development of HCC. Thus, ßI presents not only a promising inhibitory effect on NAFLD isolated but also chemopreventive activity when it is associated with hepatocarcinogenesis.


Assuntos
Carcinoma Hepatocelular/prevenção & controle , Neoplasias Hepáticas/prevenção & controle , Hepatopatia Gordurosa não Alcoólica/prevenção & controle , Norisoprenoides/uso terapêutico , Administração Oral , Animais , Apoptose/efeitos dos fármacos , Carcinoma Hepatocelular/induzido quimicamente , Carcinoma Hepatocelular/patologia , Proliferação de Células/efeitos dos fármacos , Glutationa Transferase/metabolismo , Fígado/efeitos dos fármacos , Fígado/metabolismo , Fígado/patologia , Neoplasias Hepáticas/patologia , Masculino , Hepatopatia Gordurosa não Alcoólica/induzido quimicamente , Hepatopatia Gordurosa não Alcoólica/patologia , Norisoprenoides/farmacologia , Estresse Oxidativo/efeitos dos fármacos , Ratos , Ratos Wistar , Triglicerídeos/análise
18.
Nat Commun ; 10(1): 2615, 2019 06 13.
Artigo em Inglês | MEDLINE | ID: mdl-31197154

RESUMO

Balanced expression of multiple genes is central for establishing new biosynthetic pathways or multiprotein cellular complexes. Methods for efficient combinatorial assembly of regulatory sequences (promoters) and protein coding sequences are therefore highly wanted. Here, we report a high-throughput cloning method, called COMPASS for COMbinatorial Pathway ASSembly, for the balanced expression of multiple genes in Saccharomyces cerevisiae. COMPASS employs orthogonal, plant-derived artificial transcription factors (ATFs) and homologous recombination-based cloning for the generation of thousands of individual DNA constructs in parallel. The method relies on a positive selection of correctly assembled pathway variants from both, in vivo and in vitro cloning procedures. To decrease the turnaround time in genomic engineering, COMPASS is equipped with multi-locus CRISPR/Cas9-mediated modification capacity. We demonstrate the application of COMPASS by generating cell libraries producing ß-carotene and co-producing ß-ionone and biosensor-responsive naringenin. COMPASS will have many applications in synthetic biology projects that require gene expression balancing.


Assuntos
Vias Biossintéticas/genética , Engenharia Metabólica/métodos , Proteínas de Saccharomyces cerevisiae/genética , Saccharomyces cerevisiae/metabolismo , Fatores de Transcrição/metabolismo , Proteínas de Arabidopsis/genética , Proteínas de Arabidopsis/metabolismo , Técnicas Biossensoriais/métodos , Sistemas CRISPR-Cas/genética , Clonagem Molecular/métodos , Flavanonas/biossíntese , Recombinação Homóloga/genética , Norisoprenoides/biossíntese , Regiões Promotoras Genéticas/genética , Saccharomyces cerevisiae/genética , Proteínas de Saccharomyces cerevisiae/metabolismo , Biologia Sintética/métodos , Fatores de Transcrição/genética , beta Caroteno/biossíntese
19.
J Agric Food Chem ; 67(49): 13451-13459, 2019 Dec 11.
Artigo em Inglês | MEDLINE | ID: mdl-31079451

RESUMO

Metabolic engineering aims to balance intracellular pathways and increase the precursor supply. However, some heterologous enzymes are not evolved to support high flux. To remove the limitation, the catalytic properties of rate-limiting enzymes must be enhanced. Here, we engineered carotenoid cleavage dioxygenase 1 (CCD1), whose intrinsic promiscuity and low activity limited the production of α-ionone in Escherichia coli. Site-directed mutagenesis was carried out to mutate three structural elements of CCD1: an active site loop, η-helices, and α-helices. Furthermore, mutated CCD1 was fused with lycopene ε-cyclase to facilitate substrate channelling. Collectively, these methods improved the α-ionone concentration by >2.5-fold compared to our previously optimized strain. Lastly, the engineered enzyme was used in conjunction with the metabolic engineering strategy to further boost the α-ionone concentration by another 20%. This work deepens our understanding of CCD1 catalytic properties and proves that integrating enzyme and metabolic engineering can be synergistic for a higher microbial production yield.


Assuntos
Dioxigenases/metabolismo , Proteínas de Escherichia coli/metabolismo , Escherichia coli/genética , Escherichia coli/metabolismo , Norisoprenoides/metabolismo , Biocatálise , Dioxigenases/genética , Escherichia coli/enzimologia , Proteínas de Escherichia coli/genética , Engenharia Metabólica , Mutagênese Sítio-Dirigida , Norisoprenoides/química
20.
Molecules ; 24(9)2019 May 09.
Artigo em Inglês | MEDLINE | ID: mdl-31075987

RESUMO

Ultraviolet (UV) light-induced wrinkle formation is a major dermatological problem and is associated with alteration in collagen. Here, we investigated the potential of α-ionone, a naturally occurring aromatic compound, in regulation of UVB-induced photoaging in human Hs68 dermal fibroblasts and identified the mechanisms involved. We found that in human dermal fibroblasts, α-ionone inhibited UVB-induced loss of collagen. α-Ionone upregulated the molecules participating in the TGF-ß-SMAD pathway (TGF-ß1, phospho-SMAD2/3, Col1A1, and Col1A2), but downregulated the molecules involved in the MAPK-AP-1 signaling pathway (phospho-p38, phospho-JNK, phospho-ERK, phospho-c-Fos, phospho-c-Jun, MMP1, MMP3, and MMP9), in human dermal fibroblasts. α-Ionone treatment also increased hyaluronic acid contents, and this effect was accompanied by an upregulation of mRNA expression of genes (HAS1 and HAS2) involved in hyaluronic acid synthesis. Thus, α-ionone is effective in the prevention of UVB-induced decrease of collagen and hyaluronic acid in human dermal fibroblasts. We propose that α-ionone may prove beneficial for the prevention of UV-induced wrinkle formation and skin damage.


Assuntos
Derme/patologia , Fibroblastos/efeitos dos fármacos , Fibroblastos/efeitos da radiação , Norisoprenoides/farmacologia , Envelhecimento da Pele/efeitos dos fármacos , Envelhecimento da Pele/efeitos da radiação , Raios Ultravioleta , Colágeno/metabolismo , Fibroblastos/metabolismo , Humanos , Ácido Hialurônico/metabolismo , Modelos Biológicos , Norisoprenoides/química , Regulação para Cima/efeitos dos fármacos
SELEÇÃO DE REFERÊNCIAS
DETALHE DA PESQUISA