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1.
Nat Immunol ; 21(5): 555-566, 2020 05.
Artículo en Inglés | MEDLINE | ID: mdl-32327756

RESUMEN

Regulatory myeloid immune cells, such as myeloid-derived suppressor cells (MDSCs), populate inflamed or cancerous tissue and block immune cell effector functions. The lack of mechanistic insight into MDSC suppressive activity and a marker for their identification has hampered attempts to overcome T cell inhibition and unleash anti-cancer immunity. Here, we report that human MDSCs were characterized by strongly reduced metabolism and conferred this compromised metabolic state to CD8+ T cells, thereby paralyzing their effector functions. We identified accumulation of the dicarbonyl radical methylglyoxal, generated by semicarbazide-sensitive amine oxidase, to cause the metabolic phenotype of MDSCs and MDSC-mediated paralysis of CD8+ T cells. In a murine cancer model, neutralization of dicarbonyl activity overcame MDSC-mediated T cell suppression and, together with checkpoint inhibition, improved the efficacy of cancer immune therapy. Our results identify the dicarbonyl methylglyoxal as a marker metabolite for MDSCs that mediates T cell paralysis and can serve as a target to improve cancer immune therapy.


Asunto(s)
Linfocitos T CD8-positivos/inmunología , Inmunoterapia/métodos , Melanoma/inmunología , Células Supresoras de Origen Mieloide/inmunología , Piruvaldehído/metabolismo , Amina Oxidasa (conteniendo Cobre)/metabolismo , Animales , Linfocitos T CD8-positivos/trasplante , Comunicación Celular , Proliferación Celular , Humanos , Tolerancia Inmunológica , Activación de Linfocitos , Melanoma Experimental , Ratones , Ratones Transgénicos , Neoplasias Experimentales , Receptor de Muerte Celular Programada 1/metabolismo
2.
Nature ; 579(7799): 409-414, 2020 03.
Artículo en Inglés | MEDLINE | ID: mdl-32188942

RESUMEN

Plants are essential for life and are extremely diverse organisms with unique molecular capabilities1. Here we present a quantitative atlas of the transcriptomes, proteomes and phosphoproteomes of 30 tissues of the model plant Arabidopsis thaliana. Our analysis provides initial answers to how many genes exist as proteins (more than 18,000), where they are expressed, in which approximate quantities (a dynamic range of more than six orders of magnitude) and to what extent they are phosphorylated (over 43,000 sites). We present examples of how the data may be used, such as to discover proteins that are translated from short open-reading frames, to uncover sequence motifs that are involved in the regulation of protein production, and to identify tissue-specific protein complexes or phosphorylation-mediated signalling events. Interactive access to this resource for the plant community is provided by the ProteomicsDB and ATHENA databases, which include powerful bioinformatics tools to explore and characterize Arabidopsis proteins, their modifications and interactions.


Asunto(s)
Proteínas de Arabidopsis/análisis , Proteínas de Arabidopsis/química , Arabidopsis/química , Espectrometría de Masas , Proteoma/análisis , Proteoma/química , Proteómica , Secuencias de Aminoácidos , Arabidopsis/anatomía & histología , Arabidopsis/genética , Arabidopsis/metabolismo , Proteínas de Arabidopsis/biosíntesis , Proteínas de Arabidopsis/genética , Bases de Datos de Proteínas , Conjuntos de Datos como Asunto , Regulación de la Expresión Génica de las Plantas , Anotación de Secuencia Molecular , Sistemas de Lectura Abierta , Especificidad de Órganos , Fosfoproteínas/análisis , Fosfoproteínas/química , Fosfoproteínas/genética , Fosforilación , Proteoma/biosíntesis , Proteoma/genética , ARN Mensajero/análisis , ARN Mensajero/biosíntesis , ARN Mensajero/genética , Transcriptoma
3.
Plant Cell ; 34(10): 3860-3872, 2022 09 27.
Artículo en Inglés | MEDLINE | ID: mdl-35792867

RESUMEN

Altering plant water use efficiency (WUE) is a promising approach for achieving sustainable crop production in changing climate scenarios. Here, we show that WUE can be tuned by alleles of a single gene discovered in elite maize (Zea mays) breeding material. Genetic dissection of a genomic region affecting WUE led to the identification of the gene ZmAbh4 as causative for the effect. CRISPR/Cas9-mediated ZmAbh4 inactivation increased WUE without growth reductions in well-watered conditions. ZmAbh4 encodes an enzyme that hydroxylates the phytohormone abscisic acid (ABA) and initiates its catabolism. Stomatal conductance is regulated by ABA and emerged as a major link between variation in WUE and discrimination against the heavy carbon isotope (Δ13C) during photosynthesis in the C4 crop maize. Changes in Δ13C persisted in kernel material, which offers an easy-to-screen proxy for WUE. Our results establish a direct physiological and genetic link between WUE and Δ13C through a single gene with potential applications in maize breeding.


Asunto(s)
Ácido Abscísico , Zea mays , Ácido Abscísico/metabolismo , Ácido Abscísico/farmacología , Alelos , Isótopos de Carbono , Fotosíntesis/genética , Reguladores del Crecimiento de las Plantas/metabolismo , Hojas de la Planta/metabolismo , Agua/metabolismo , Zea mays/metabolismo
4.
Metab Eng ; 82: 193-200, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38387676

RESUMEN

Diterpenoids form a diverse group of natural products, many of which are or could become pharmaceuticals or industrial chemicals. The modular character of diterpene biosynthesis and the promiscuity of the enzymes involved make combinatorial biosynthesis a promising approach to generate libraries of diverse diterpenoids. Here, we report on the combinatorial assembly in yeast of ten diterpene synthases producing (+)-copalyl diphosphate-derived backbones and four cytochrome P450 oxygenases (CYPs) in diverse combinations. This resulted in the production of over 200 diterpenoids. Based on literature and chemical database searches, 162 of these compounds can be considered new-to-Nature. The CYPs accepted most substrates they were given but remained regioselective with few exceptions. Our results provide the basis for the systematic exploration of the diterpenoid chemical space in yeast using sequence databases.


Asunto(s)
Productos Biológicos , Diterpenos , Saccharomyces cerevisiae/genética , Diterpenos/química , Sistema Enzimático del Citocromo P-450/genética
5.
Plant Cell Environ ; 47(4): 1224-1237, 2024 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-38164085

RESUMEN

Plants employ a multilayered immune system to combat pathogens. In one layer, recognition of Pathogen- or Microbe-Associated Molecular Patterns or elicitors, triggers a cascade that leads to defence against the pathogen and Pattern Triggered Immunity. Secondary or specialised metabolites (SMs) are expected to play a role, because they are potentially anti-fungal compounds. Tomato (Solanum lycopersicum) plants inoculated with Alternaria solani s.l. show symptoms of infection after inoculation. Plants inoculated with Alternaria alternata remain symptomless. We hypothesised that pattern-triggered induction of resistance related metabolites in tomato contributes to the resistance against A. alternata. We compared the metabolomic profile (metabolome) of tomato after treatments with A. alternata, A. solani and the fungal elicitor chitin, and identified SMs involved in early defence of tomato plants. We revealed differential metabolome fingerprints. The composition of A. alternata and chitin induced metabolomes show larger overlap with each other than with the A. solani induced metabolome. We identify 65 metabolites possibly associated with PTI in tomato plants, including NAD and trigonelline. We confirm that trigonelline inhibits fungal growth in vitro at physiological concentrations. Thus, a true pattern-triggered, chemical defence is mounted against A. alternata, which contains anti-fungal compounds that could be interesting for crop protection strategies.


Asunto(s)
Proteínas de Plantas , Solanum lycopersicum , Proteínas de Plantas/metabolismo , Resistencia a la Enfermedad , Enfermedades de las Plantas/microbiología , Alternaria/metabolismo , Quitina
6.
Proc Natl Acad Sci U S A ; 118(39)2021 09 28.
Artículo en Inglés | MEDLINE | ID: mdl-34561304

RESUMEN

Plant innate immunity is activated upon perception of invasion pattern molecules by plant cell-surface immune receptors. Several bacteria of the genera Pseudomonas and Burkholderia produce rhamnolipids (RLs) from l-rhamnose and (R)-3-hydroxyalkanoate precursors (HAAs). RL and HAA secretion is required to modulate bacterial surface motility, biofilm development, and thus successful colonization of hosts. Here, we show that the lipidic secretome from the opportunistic pathogen Pseudomonas aeruginosa, mainly comprising RLs and HAAs, stimulates Arabidopsis immunity. We demonstrate that HAAs are sensed by the bulb-type lectin receptor kinase LIPOOLIGOSACCHARIDE-SPECIFIC REDUCED ELICITATION/S-DOMAIN-1-29 (LORE/SD1-29), which also mediates medium-chain 3-hydroxy fatty acid (mc-3-OH-FA) perception, in the plant Arabidopsis thaliana HAA sensing induces canonical immune signaling and local resistance to plant pathogenic Pseudomonas infection. By contrast, RLs trigger an atypical immune response and resistance to Pseudomonas infection independent of LORE. Thus, the glycosyl moieties of RLs, although abolishing sensing by LORE, do not impair their ability to trigger plant defense. Moreover, our results show that the immune response triggered by RLs is affected by the sphingolipid composition of the plasma membrane. In conclusion, RLs and their precursors released by bacteria can both be perceived by plants but through distinct mechanisms.


Asunto(s)
Arabidopsis/inmunología , Arabidopsis/microbiología , Glucolípidos/metabolismo , Inmunidad de la Planta/fisiología , Pseudomonas syringae/patogenicidad , Proteínas de Arabidopsis/genética , Proteínas de Arabidopsis/inmunología , Proteínas de Arabidopsis/metabolismo , Señalización del Calcio , Resistencia a la Enfermedad/inmunología , Glucolípidos/química , Interacciones Huésped-Patógeno/fisiología , Inmunidad Innata , Fosforilación , Enfermedades de las Plantas/inmunología , Enfermedades de las Plantas/microbiología , Plantas Modificadas Genéticamente , Proteínas Serina-Treonina Quinasas/genética , Proteínas Serina-Treonina Quinasas/inmunología , Proteínas Serina-Treonina Quinasas/metabolismo , Pseudomonas syringae/metabolismo , Especies Reactivas de Oxígeno/metabolismo , Nicotiana/genética , Nicotiana/metabolismo
7.
J Exp Bot ; 74(10): 3240-3254, 2023 05 19.
Artículo en Inglés | MEDLINE | ID: mdl-36880316

RESUMEN

Natural plant populations are polymorphic and show intraspecific variation in resistance properties against pathogens. The activation of the underlying defence responses can depend on variation in perception of pathogen-associated molecular patterns or elicitors. To dissect such variation, we evaluated the responses induced by laminarin (a glucan, representing an elicitor from oomycetes) in the wild tomato species Solanum chilense and correlated this to observed infection frequencies of Phytophthora infestans. We measured reactive oxygen species burst and levels of diverse phytohormones upon elicitation in 83 plants originating from nine populations. We found high diversity in basal and elicitor-induced levels of each component. Further we generated linear models to explain the observed infection frequency of P. infestans. The effect of individual components differed dependent on the geographical origin of the plants. We found that the resistance in the southern coastal region, but not in the other regions, was directly correlated to ethylene responses and confirmed this positive correlation using ethylene inhibition assays. Our findings reveal high diversity in the strength of defence responses within a species and the involvement of different components with a quantitatively different contribution of individual components to resistance in geographically separated populations of a wild plant species.


Asunto(s)
Phytophthora infestans , Solanum lycopersicum , Solanum tuberosum , Solanum , Etilenos , Glucanos , Phytophthora infestans/fisiología , Enfermedades de las Plantas
8.
J Exp Bot ; 74(21): 6820-6835, 2023 11 21.
Artículo en Inglés | MEDLINE | ID: mdl-37668551

RESUMEN

Plants often face simultaneous abiotic and biotic stress conditions; however, physiological and transcriptional responses under such combined stress conditions are still not fully understood. Spring barley (Hordeum vulgare) is susceptible to Fusarium head blight (FHB), which is strongly affected by weather conditions. We therefore studied the potential influence of drought on FHB severity and plant responses in three varieties of different susceptibility. We found strongly reduced FHB severity in susceptible varieties under drought. The number of differentially expressed genes (DEGs) and strength of transcriptomic regulation reflected the concentrations of physiological stress markers such as abscisic acid or fungal DNA contents. Infection-related gene expression was associated with susceptibility rather than resistance. Weighted gene co-expression network analysis revealed 18 modules of co-expressed genes that reflected the pathogen- or drought-response in the three varieties. A generally infection-related module contained co-expressed genes for defence, programmed cell death, and mycotoxin detoxification, indicating that the diverse genotypes used a similar defence strategy towards FHB, albeit with different degrees of success. Further, DEGs showed co-expression in drought- or genotype-associated modules that correlated with measured phytohormones or the osmolyte proline. The combination of drought stress with infection led to the highest numbers of DEGs and resulted in a modular composition of the single-stress responses rather than a specific transcriptional output.


Asunto(s)
Fusarium , Hordeum , Hordeum/genética , Hordeum/microbiología , Sequías , Fusarium/fisiología , Perfilación de la Expresión Génica , Transcriptoma , Enfermedades de las Plantas/genética , Enfermedades de las Plantas/microbiología
9.
PLoS Genet ; 16(1): e1008433, 2020 01.
Artículo en Inglés | MEDLINE | ID: mdl-31961852

RESUMEN

Plant cells are encased in a semi-rigid cell wall of complex build. As a consequence, cell wall remodeling is essential for the control of growth and development as well as the regulation of abiotic and biotic stress responses. Plant cells actively sense physico-chemical changes in the cell wall and initiate corresponding cellular responses. However, the underlying cell wall monitoring mechanisms remain poorly understood. In Arabidopsis the atypical receptor kinase STRUBBELIG (SUB) mediates tissue morphogenesis. Here, we show that SUB-mediated signal transduction also regulates the cellular response to a reduction in the biosynthesis of cellulose, a central carbohydrate component of the cell wall. SUB signaling affects early increase of intracellular reactive oxygen species, stress gene induction as well as ectopic lignin and callose accumulation upon exogenous application of the cellulose biosynthesis inhibitor isoxaben. Moreover, our data reveal that SUB signaling is required for maintaining cell size and shape of root epidermal cells and the recovery of root growth after transient exposure to isoxaben. SUB is also required for root growth arrest in mutants with defective cellulose biosynthesis. Genetic data further indicate that SUB controls the isoxaben-induced cell wall stress response independently from other known receptor kinase genes mediating this response, such as THESEUS1 or MIK2. We propose that SUB functions in a least two distinct biological processes: the control of tissue morphogenesis and the response to cell wall damage. Taken together, our results reveal a novel signal transduction pathway that contributes to the molecular framework underlying cell wall integrity signaling.


Asunto(s)
Proteínas de Arabidopsis/metabolismo , Celulosa/metabolismo , Proteínas Tirosina Quinasas Receptoras/metabolismo , Arabidopsis , Proteínas de Arabidopsis/genética , Tamaño de la Célula , Pared Celular/metabolismo , Raíces de Plantas/genética , Raíces de Plantas/crecimiento & desarrollo , Raíces de Plantas/metabolismo , Proteínas Tirosina Quinasas Receptoras/genética , Transducción de Señal , Estrés Fisiológico
10.
PLoS Genet ; 15(8): e1008327, 2019 08.
Artículo en Inglés | MEDLINE | ID: mdl-31465451

RESUMEN

Karrikins are smoke-derived compounds presumed to mimic endogenous signalling molecules (KAI2-ligand, KL), whose signalling pathway is closely related to that of strigolactones (SLs), important regulators of plant development. Both karrikins/KLs and SLs are perceived by closely related α/ß hydrolase receptors (KAI2 and D14 respectively), and signalling through both receptors requires the F-box protein MAX2. Furthermore, both pathways trigger proteasome-mediated degradation of related SMAX1-LIKE (SMXL) proteins, to influence development. It has previously been suggested in multiple studies that SLs are important regulators of root and root hair development in Arabidopsis, but these conclusions are based on phenotypes observed in the non-specific max2 mutants and by use of racemic-GR24, a mixture of stereoisomers that activates both D14 and KAI2 signalling pathways. Here, we demonstrate that the majority of the effects on Arabidopsis root development previously attributed to SL signalling are actually mediated by the KAI2 signalling pathway. Using mutants defective in SL or KL synthesis and/or perception, we show that KAI2-mediated signalling alone regulates root hair density and root hair length as well as root skewing, straightness and diameter, while both KAI2 and D14 pathways regulate lateral root density and epidermal cell length. We test the key hypothesis that KAI2 signals by a non-canonical receptor-target mechanism in the context of root development. Our results provide no evidence for this, and we instead show that all effects of KAI2 in the root can be explained by canonical SMAX1/SMXL2 activity. However, we do find evidence for non-canonical GR24 ligand-receptor interactions in D14/KAI2-mediated root hair development. Overall, our results demonstrate that the KAI2 signalling pathway is an important new regulator of root hair and root development in Arabidopsis and lay an important basis for research into a molecular understanding of how very similar and partially overlapping hormone signalling pathways regulate different phenotypic outputs.


Asunto(s)
Proteínas de Arabidopsis/metabolismo , Arabidopsis/crecimiento & desarrollo , Hidrolasas/metabolismo , Raíces de Plantas/crecimiento & desarrollo , Arabidopsis/genética , Proteínas de Arabidopsis/genética , Regulación del Desarrollo de la Expresión Génica , Regulación de la Expresión Génica de las Plantas , Hidrolasas/genética , Péptidos y Proteínas de Señalización Intracelular/genética , Péptidos y Proteínas de Señalización Intracelular/metabolismo , Mutación , Reguladores del Crecimiento de las Plantas/biosíntesis , Plantas Modificadas Genéticamente , Transducción de Señal/genética
11.
Int J Mol Sci ; 23(18)2022 Sep 09.
Artículo en Inglés | MEDLINE | ID: mdl-36142393

RESUMEN

Flaxseeds are typically consumed either as whole flaxseed, ground flaxseed, flaxseed oil, partially defatted flaxseed meal, or as a milk alternative. They are considered a rich source of vitamins, minerals, proteins and peptides, lipids, carbohydrates, lignans, and dietary fiber, which have shown hypolipidemic, antiatherogenic, anticholesterolemic, and anti-inflammatory property activity. Here, an in vitro batch culture model was used to investigate the influence of whole milled flaxseed and partially defatted milled flaxseed press cake on the gut microbiota and the liberation of flaxseed bioactives. Microbial communities were profiled using 16S rRNA gene-based high-throughput sequencing with targeted mass spectrometry measuring lignan, cyclolinopeptide, and bile acid content and HPLC for short-chain fatty acid profiles. Flaxseed supplementation decreased gut microbiota richness with Firmicutes, Proteobacteria, and Bacteroidetes becoming the predominant phyla. Secoisolariciresinol, enterodiol, and enterolactone were rapidly produced with acetic acid, butyric acid, and propionic acid being the predominant acids after 24 h of fermentation. The flaxseed press cake and whole flaxseed were equivalent in microbiota changes and functionality. However, press cake may be superior as a functional additive in a variety of foods in terms of consumer acceptance as it would be more resistant to oxidative changes.


Asunto(s)
Lino , Microbioma Gastrointestinal , Lignanos , Antiinflamatorios , Ácidos y Sales Biliares , Ácido Butírico , Fibras de la Dieta/análisis , Ácidos Grasos Volátiles , Lino/metabolismo , Humanos , Lignanos/química , Aceite de Linaza , Metaboloma , Propionatos , ARN Ribosómico 16S/metabolismo , Vitaminas/análisis
12.
Molecules ; 27(3)2022 Jan 27.
Artículo en Inglés | MEDLINE | ID: mdl-35164132

RESUMEN

The emetic Bacillus cereus toxin cereulide (1) poses a significant safety risk in the food industry, causing emesis and nausea after consumption of contaminated foods. Analogously to cereulide, the structures of various isocereulides, namely, isocereulides A-G, have been recently reported and could also be identified in B. cereus-contaminated food samples. The HPLC fractionation of B. cereus extracts allows us to isolate additional isocereulides. By applying MSn sequencing, post-hydrolytic dipeptide, amino acid and α-hydroxy acid analyses using UPLC-ESI-TOF-MS to purify the analytes, seven new isocereulides H-N (2-8) could be elucidated in their chemical structures. The structure elucidation was supported by one-dimensional and two-dimensional NMR spectra of the isocereulides H (2), K (5), L and N (6 + 8) and M (7). The toxicity of 2-8 was investigated in a HEp-2 cell assay to determine their respective 50% effective concentration (EC50). Thus, 2-8 exhibited EC50 values ranging from a 0.4- to 1.4-fold value compared to cereulide (1). Missing structure-activity correlations indicate the necessity to determine the toxic potential of all naturally present isocereulides as single compounds to be able to perform a thorough toxicity evaluation of B. cereus-contaminated foods in the future.


Asunto(s)
Bacillus cereus/química , Toxinas Bacterianas/química , Depsipéptidos/química , Espectrometría de Masas , Resonancia Magnética Nuclear Biomolecular , Microbiología de Alimentos
13.
Int J Mol Sci ; 22(20)2021 Oct 15.
Artículo en Inglés | MEDLINE | ID: mdl-34681798

RESUMEN

Salix cortex-containing medicine is used against pain conditions, fever, headaches, and inflammation, which are partly mediated via arachidonic acid-derived prostaglandins (PGs). We used an activity-guided fractionation strategy, followed by structure elucidation experiments using LC-MS/MS, CD-spectroscopy, and 1D/2D NMR techniques, to identify the compounds relevant for the inhibition of PGE2 release from activated human peripheral blood mononuclear cells. Subsequent compound purification by means of preparative and semipreparative HPLC revealed 2'-O-acetylsalicortin (1), 3'-O-acetylsalicortin (2), 2'-O-acetylsalicin (3), 2',6'-O-diacetylsalicortin (4), lasiandrin (5), tremulacin (6), and cinnamrutinose A (7). In contrast to 3 and 7, compounds 1, 2, 4, 5, and 6 showed inhibitory activity against PGE2 release with different potencies. Polyphenols were not relevant for the bioactivity of the Salix extract but salicylates, which degrade to, e.g., catechol, salicylic acid, salicin, and/or 1-hydroxy-6-oxo-2-cycohexenecarboxylate. Inflammation presents an important therapeutic target for pharmacological interventions; thus, the identification of relevant key drugs in Salix could provide new prospects for the improvement and standardization of existing clinical medicine.


Asunto(s)
Inflamación/tratamiento farmacológico , Salicilatos/aislamiento & purificación , Salix/química , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Células Cultivadas , Cromatografía Liquida , Dinoprostona/metabolismo , Humanos , Leucocitos Mononucleares/efectos de los fármacos , Leucocitos Mononucleares/metabolismo , Terapia Molecular Dirigida/métodos , Terapia Molecular Dirigida/tendencias , Dolor/tratamiento farmacológico , Fitoterapia/métodos , Corteza de la Planta/química , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología , Extractos Vegetales/uso terapéutico , Salicilatos/análisis , Salicilatos/farmacología , Espectrometría de Masas en Tándem
14.
Int J Mol Sci ; 22(13)2021 Jun 23.
Artículo en Inglés | MEDLINE | ID: mdl-34201817

RESUMEN

The usefulness of anti-inflammatory drugs as an adjunct therapy to improve outcomes in COVID-19 patients is intensely discussed in this paper. Willow bark (Salix cortex) has been used for centuries to relieve pain, inflammation, and fever. Its main active ingredient, salicin, is metabolized in the human body into salicylic acid, the precursor of the commonly used pain drug acetylsalicylic acid (ASA). Here, we report on the in vitro anti-inflammatory efficacy of two methanolic Salix extracts, standardized to phenolic compounds, in comparison to ASA in the context of a SARS-CoV-2 peptide challenge. Using SARS-CoV-2 peptide/IL-1ß- or LPS-activated human PBMCs and an inflammatory intestinal Caco-2/HT29-MTX co-culture, Salix extracts, and ASA concentration-dependently suppressed prostaglandin E2 (PGE2), a principal mediator of inflammation. The inhibition of COX-2 enzyme activity, but not protein expression was observed for ASA and one Salix extract. In activated PBMCs, the suppression of relevant cytokines (i.e., IL-6, IL-1ß, and IL-10) was seen for both Salix extracts. The anti-inflammatory capacity of Salix extracts was still retained after transepithelial passage and liver cell metabolism in an advanced co-culture model system consisting of intestinal Caco-2/HT29-MTX cells and differentiated hepatocyte-like HepaRG cells. Taken together, our in vitro data suggest that Salix extracts might present an additional anti-inflammatory treatment option in the context of SARS-CoV-2 peptides challenge; however, more confirmatory data are needed.


Asunto(s)
Antiinflamatorios/farmacología , Aspirina/farmacología , Tratamiento Farmacológico de COVID-19 , COVID-19/inmunología , Extractos Vegetales/farmacología , Antiinflamatorios/química , Alcoholes Bencílicos/metabolismo , COVID-19/virología , Células CACO-2 , Ciclooxigenasa 2/efectos de los fármacos , Citocinas/metabolismo , Dinoprostona/metabolismo , Glucósidos/metabolismo , Células HT29 , Humanos , Inflamación , Leucocitos Mononucleares/efectos de los fármacos , Lipopolisacáridos/inmunología , Corteza de la Planta/química , Extractos Vegetales/química , SARS-CoV-2/inmunología
15.
J Nat Prod ; 81(8): 1734-1744, 2018 08 24.
Artículo en Inglés | MEDLINE | ID: mdl-30063346

RESUMEN

European licorice roots ( Glycyrrhiza glabra), used in the food and beverage industry due to their distinctive sweet and typical licorice flavor, were fractionated, with the triterpenoid saponins isolated and their chemical structures determined by means of ESIMS, ESIMS/MS, HRESIMS, and 1D/2D NMR experiments. Next to the quantitatively predominant saponin glycyrrhizin (11) and some previously known saponins, the structures of 10 monodesmosidic saponins were assigned unequivocally for the first time, namely, 30-hydroxyglycyrrhizin (1), glycyrrhizin-20-methanoate (2), 24-hydroxyglucoglycyrrhizin (3), rhaoglycyrrhizin (4), 11-deoxorhaoglycyrrhizin (5), rhaoglucoglycyrrhizin (6), rhaogalactoglycyrrhizin (7), 11-deoxo-20α-glycyrrhizin (8), 20α-galacturonoylglycyrrhizin (9), and 20α-rhaoglycyrrhizin (10).


Asunto(s)
Glycyrrhiza/química , Raíces de Plantas/química , Saponinas/farmacología , Antioxidantes/análisis , Espectroscopía de Resonancia Magnética , Estructura Molecular , Monosacáridos/química , Extractos Vegetales/química , Espectrometría de Masa por Ionización de Electrospray
16.
J Agric Food Chem ; 2024 Jun 04.
Artículo en Inglés | MEDLINE | ID: mdl-38833300

RESUMEN

The application of high-performance liquid chromatography-mass spectrometry (HPLC-MS/MS) revealed the origin and evolution of antioxidants during the brewing process of hopped and unhopped reference beer. As tachioside (3-methoxy-4-hydroxyphenyl-ß-d-glucopyranoside), arbutin (4-hydroxyphenyl-ß-d-glucopyranoside), and hordatines clearly increased during the fermentation step, the raw material barley was investigated as a source of the corresponding precursors. Therefore, 4-hydroxyphenyl-ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranoside, 4-hydroxy-3-methoxyphenyl-ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranoside, 4-hydroxy-3-methoxyphenyl-ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranoside, and 4-hydroxy-2-methoxyphenyl-ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranoside were isolated from barley for the first time, and identified using liquid chromatography-mass spectrometry (LC-MS) and one-dimensional/two-dimensional-nuclear magnetic resonance (1D/2D-NMR) experiments. Moreover, hordatine glucosides A, B, and C were isolated and identified from barley, and hordatine C glucoside was characterized for the first time. A fermentation model followed by HPLC-MS/MS analysis substantiated the release of tachioside from 4-hydroxy-3-methoxyphenyl-ß-d-glucopyranosyl-(1 → 6)-ß-d-glucopyranoside by Saccharomyces cerevisiae. Quantitation experiments monitoring the content in wheat, barley, and different barley malt types demonstrated a wide range of concentrations, providing a basis for further comprehensive investigations to optimize the antioxidant yield in beer to contribute to improved flavor stability.

17.
Food Chem ; 440: 138252, 2024 May 15.
Artículo en Inglés | MEDLINE | ID: mdl-38160594

RESUMEN

A balanced flavor is a major quality attribute of orange juice. Formation of 4-vinylguaiacol during storage can lead to an undesirable clove-like off-flavor. However, clove-like off-flavors were occasionally reported despite low 4-vinylguaiacol concentrations, suggesting an alternative molecular background. Application of gas chromatography-olfactometry and aroma extract dilution analysis to an orange juice with a pronounced clove-like off-flavor resulted in the identification of 5-vinylguaiacol. The compound showed the same odor as 4-vinylguaiacol, but was previously unknown in orange juice. In five of six commercial orange juices with clove-like off-flavors, 5-vinylguaiacol was even more odor-active than 4-vinylguaiacol. Spiking and model studies suggested that 5-vinylguaiacol is formed during pasteurization from the natural orange juice component hesperidin and residual peracetic acid used as cleaning agent by a Baeyer-Villiger oxidation. An activity-guided screening approach confirmed the role of hesperidin as 5-vinylguaiacol precursor. In conclusion, peracetic acid should no longer be used in orange juice processing plants.


Asunto(s)
Citrus sinensis , Guayacol/análogos & derivados , Hesperidina , Syzygium , Citrus sinensis/química , Hesperidina/farmacología , Ácido Peracético , Odorantes/análisis
18.
J Agric Food Chem ; 72(18): 10558-10569, 2024 May 08.
Artículo en Inglés | MEDLINE | ID: mdl-38668637

RESUMEN

As a traditional Thai condiment, Pla-ra is used to add flavor and richness to dishes. Nine treatment combinations of Pla-ra formulations created from 3 types of fish (Mor fish, Kradee fish, and Mor + Kradee fish) and 4 different carbohydrate sources (none, rice bran, roasted rice, and rice bran─roasted rice mixture) were studied through a 12 month fermentation period (1, 3, 5, 7, 8, 9, 10, 11, and 12 months). 16S rRNA Next Generation Sequencing (NGS) and LC-MS/MS techniques were used to analyze the microbial diversity and identify taste-enhancing peptides. Descriptive sensory analysis was performed on the extracts of the 108 Pla-ra samples mixed in a model broth. Koku perception and saltiness-enhancing attributes were clearly perceived and dominant in all samples, even though glutamyl peptides, including γ-Glu-Val-Gly, were found at subthreshold levels. The samples from mixed fish and Mor fish fermented with roasted ground rice and rice bran for 12 months had the most typical Pla-ra odors and tastes and had high taste-enhancing activities. NGS analysis revealed the presence of bacteria containing a large number of protease and aminopeptidase genes in the samples. Bacillus spp., Gallicola spp., and Proteiniclasticum spp. correlated well with the generation of glutamyl and arginyl peptides and typical odors in the samples. These results confirmed the typical sensory quality of Pla-ra depended on protein sources, carbohydrate sources, and bacteria communities. Further optimization of the microbial composition found could lead to the development of starter cultures to control and promote flavor development in fermented fish products.


Asunto(s)
Bacterias , Fermentación , Peces , Aromatizantes , Microbiota , Péptidos , Gusto , Animales , Bacterias/clasificación , Bacterias/genética , Bacterias/aislamiento & purificación , Bacterias/metabolismo , Aromatizantes/química , Aromatizantes/metabolismo , Peces/microbiología , Tailandia , Humanos , Péptidos/metabolismo , Productos Pesqueros/análisis , Productos Pesqueros/microbiología , Alimentos Fermentados/análisis , Alimentos Fermentados/microbiología , Odorantes/análisis , Masculino , Femenino , Adulto , Oryza/química , Oryza/microbiología , Oryza/metabolismo , ARN Ribosómico 16S/genética , Condimentos/análisis , Condimentos/microbiología , Pueblos del Sudeste Asiático
19.
Foods ; 13(4)2024 Feb 08.
Artículo en Inglés | MEDLINE | ID: mdl-38397504

RESUMEN

In order to characterize red wine polymers with regard to their binding properties to aroma compounds (odorants), a qualitative and quantitative analysis of chemical degradation products after different chemical treatments (thiolytic, acidic, and alkaline depolymerization) of high -molecular-weight (HMW) fractions of red wine was performed. Using 1H NMR, LC-ToF-MS, LC-MS/MS, and HPIC revealed key structural features such as carbohydrates, organic acids, phenolic compounds, anthocyanins, anthocyanidins, amino acids, and flavan-3-ols responsible for odorant-polymer interactions. Further, NMR-based interaction studies of the selected aroma compounds 3-methylbutanol, cis-whisky lactone, 3-methylbutanoic acid, and 3-isobutyl-2-methoxypyrazine with HMW polymers after chemical treatment demonstrated a reduced interaction affinity of the polymer compared to the native HMW fractions, and further, the importance of aromatic compounds such as flavan-3-ols for the formation of odorant polymer interactions. In addition, these observations could be verified by human sensory experiments. For the first time, the combination of a compositional analysis of red wine polymers and NMR-based interaction studies with chemically treated HMW fractions enabled the direct analysis of the correlation of the polymer's structure and its interaction affinity with key odorants in red wine.

20.
Food Res Int ; 180: 114070, 2024 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-38395559

RESUMEN

This study aimed to modify the sensory properties of rapeseed protein concentrate using a combination of fermentation and high-moisture extrusion processing for producing meat analogues. The fermentation was carried out with Lactiplantibacillus plantarum and Weissella confusa strains, known for their flavour and structure-enhancing properties. Contrary to expectations, the sensory evaluation revealed that the fermentation induced bitterness and disrupted the fibrous structure formation ability due to the generation of short peptides. On the other hand, fermentation removed the intensive off-odour and flavour notes present in the native raw material. Several control treatments were produced to understand the reasons behind the hindered fibrous structure formation and induced bitterness. The results obtained from peptidomics, free amino ends, and solubility analyses strongly indicated that the proteins were hydrolysed by endoproteases activated during the fermentation process. Furthermore, it was suspected that the proteins and/or peptides formed complexes with other components, such as hydrolysis products of glucosinolates and polysaccharides.


Asunto(s)
Brassica napus , Brassica rapa , Fermentación , Sustitutos de la Carne , Polisacáridos , Concentración de Iones de Hidrógeno
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