•Abiotic stress produces changes in the metabolome of purslane.•Adverse salinity conditions lead to a higher concentration of functional metabolites.•Low fertilization levels in field or hydroponics ...stimulate the production of nutraceutical compounds in purslane.•Metabolomics techniques based on 1H NMR have helped to elucidate the metabolome of purslane under stress growth conditions.
Purslane (Portulaca oleracea L.) is an herbaceous plant consumed in Italy, the United Kingdom, Spain, Greece, Turkey, Iran, Malaysia, the Philippines, China, North Africa, Australia, the United States, Brazil, and Mexico. Purslane contains nutraceutical compounds that can be potentiated based on biotic and abiotic stress practices. It provides substantial contributions of minerals, polysaccharides, fatty acids, proteins, alkaloids, terpenoids, sterols, phenols, flavonoids, and vitamins, which together or individually provide neuroprotective, antimicrobial, antidiabetic, antioxidant, anti-inflammatory, antiulcerogenic, anticancer, and anticholinesterase properties. The preference for foods with high nutraceutical value, which provide benefits to human health and contribute to the prevention of diseases, mainly chronic-degenerative diseases, is increasing. In this review, the information regarding the effects of crop management on the chemical composition, medicinal effects, and new functional compounds with techniques based on metabolomics is updated. Under adverse edaphoclimatic conditions, an increase in nutraceutical compounds has been observed, which represents a production alternative given its nutritional and commercial value. Metabolomics techniques based on 1H NMR have helped elucidate the metabolome of purslane under specific growth conditions (stress, hydroponics, open field, and controlled), with reports of new compounds from the groups of lignans, flavonoids, homoisoflavonoids, homoisoflavones, amide glycosides, alkaloids, amide and isoindole alkaloids, and phenolic alkaloids such as oleraceins; this has broadened the potential food and medicinal panorama of this plant.
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In marine environments, biofilm can cause negative impacts, including the biofouling process. In the search for new non-toxic formulations that inhibit biofilm, biosurfactants (BS) produced by the ...genus
have demonstrated considerable potential. To elucidate the changes that BS from
promote in growth inhibition and biofilm formation, this research performed a nuclear magnetic resonance (NMR) metabolomic profile analysis to compare the metabolic differences between planktonic cells and biofilms of
, a pioneer fouling bacteria. The multivariate analysis showed a clear separation between groups with a higher concentration of metabolites in the biofilm than in planktonic cells of
. When planktonic and biofilm stages were treated with BS, some differences were found among them. In planktonic cells, the addition of BS had a minor effect on growth inhibition, but at a metabolic level, NADP+, trehalose, acetone, glucose, and betaine were up-regulated in response to osmotic stress. When the biofilm was treated with the BS, a clear inhibition was observed and metabolites such as glucose, acetic acid, histidine, lactic acid, phenylalanine, uracil, and NADP+ were also up-regulated, while trehalose and histamine were down-regulated in response to the antibacterial effect of the BS.
Rhizopus rot is a common postharvest disease that causes devastating economic losses for peach producers around the world. Thus, new alternatives for the control of this disease are required. Herein ...we report on the obtainment of a new hydrotalcite/shilovite (HT/Sh) composite with in situ fungistatic properties on Rhizopus stolonifer. The protective effect of this composite was studied at the metabolic level by non-targeted 1H NMR metabolomics (coupled to PCA and OPLS-DA models) and RP-HPLC to determine possible changes in the primary and secondary metabolism of peaches. Our results demonstrated that the HT/Sh composite exerted a protective effect on the levels of specific sugars (glucose, ribose, and xylose) amino acids (glutamic acid, glutamine, histidine, isoleucine, leucine threonine, and valine), phenols (chlorogenic and neochlorogenic acids) and carotenoids (neoxanthin, violaxanthin, lutein, zeaxanthin, β-cryptoxanthin, and β-carotene). Our findings demonstrated that the new HT/Sh composite reported in this work was able to retard the emergence of Rhizopus rot in peaches for ten days and promoted the conservation of their nutraceutical content.
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•A new antifungal shilovite/hydrotalcite composite was synthesized.•This material avoided side effects of peaches infected with Rhizopus infection.•Changes in the nutraceutical content were determined through NMR and HPLC.
The
H-NMR metabolomics profiling of six edible mushrooms consumed in the northeastern highlands of Puebla, Mexico is presented. These fungi were morpho- and molecularly identified as Infundibulicybe ...squamulosa, Amanita jacksonii, Lepista nuda, Russula delica, Russula brevipes, and Lactarius indigo. The chemical profiling confirmed the presence of eight essential amino acids and their derivatives, six organic acids, six nucleosides, low amounts of reducing sugars, and valuable nutraceuticals such as betaine, carnitine, glycero-3-phosphocholine and O-acetylcarnitine which were differentially determined and quantified in the six mushrooms by qNMR. Principal component analysis (PCA) and orthogonal projections to latent structures discriminant analysis (OPLS-DA) generated four different groups. Two of these groups were constituted by fungal species with phylogenic relationships whereas non-phylogenetic related species were separated from each other. The potential use of
H-NMR metabolomics and chemometrics to group macromycetes and determine the nutritional and nutraceutical potential of these local foods is demonstrated.
Mexico is one of the main producers of prickly pear worldwide and has around 50 registered accessions. Despite its great nutritional value, there are no reports on its metabolite profile. The ...objective of this study was to analyze 12 accessions of prickly pear (TAC, TNL, TCB, TCO, TV, TZ, TRI, TRP, TRR, TS, TSH and TT) of different colors using nuclear magnetic resonance (NMR) spectroscopy to identify their metabolic profiles. Principal component analysis (PCA) and orthogonal partial least squares discriminant analysis (OPLS-DA) were used to compare the metabolome. In total, 34 primary metabolites were identified in the 1H NMR spectra. The PCA model used to compare the 12 accessions did not show a clear separation between the groups. The OPLS-DA model made it possible to discriminate the TRI and TCB accessions. The heatmap showed that these accessions have a higher concentration of some metabolites. The TCB accession has high concentrations of sugars and amino acids while the TRI accession has high concentrations of organic acids. In addition, The TCO accession has a lower concentration of primary metabolites. The OPLS-DA model made it possible to classify the prickly pears by color. For orange prickly pears, the TNL accession has a higher concentration of primary metabolites than the TAC accession. In green prickly pears, the accession with the highest concentration of primary metabolites is the TCB accession, while it is the TRI accession in red prickly pears. This work demonstrated that NMR-based metabolomics is a highly reproducible and robust methodology to classify prickly pear accessions.
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•The 1H NMR metabolomics profiling of prickly pears accession is studied.•Thirty-four metabolites were identified in prickly pear accessions.•Metabolic profile was used to discriminate between prickly pear accessions of different colour.•With the multivariate analysis, biomarkers were identified between prickly pear accessions.
The northern highlands of Puebla harbor several plant foods consumed since pre-Columbian times. Most of the native vegetables from this geographical region are still uncharacterized at the ...nutraceutical level. This investigation was focused on the elucidation of chemical and biochemical properties of the edible organs from Rhamnus pompana, Solanum nigrescens, Sechium edule, Yucca aloifolia, Piper auritum, Amaranthus hybridus and Rumex obtusifolius, which are used as traditional foods in this region. The content of basic nutrients (including vitamins of the B complex), nutraceuticals (carotenoids, flavonoids, and fatty acids), phenolics (including antioxidant capacity), and inhibitory properties of these plants on specific enzymes linked to carbohydrate and lipid metabolism were determined. In addition, extracts of these plants were evaluated against pathogenic microorganisms of the gastrointestinal tract. Our results demonstrated statistically significant divergences (p < 0.05) in the content protein (12.5 g/100 g), fiber (9.8 g/100 g), fat (81.2 mg/100 g), beta-carotene (2.48 mg/100 g), beta-cryptoxanthin (1.24 mg/100 g), thiamine (159.6 µg/100 g), riboflavin (106.4 µg/100 g), and vitamin B6 between Y. aloifolia and other plants studied. All plants showed low amounts of reducing sugars (<150 mg/100 g) and sodium (<70 mg/100 g), but the berries of R. pompana exhibited substantial differences (p < 0.05) in the levels of vitamin C (14.6 mg/100 mg). The edible leaves of R. obtusifolius were particularly rich in quercetin (4.38 mg/100 g), kaempferol (2.38 mg/100 g) and lutein (2.52 mg/100 g), whereas the aerial parts of S. edule contained high concentrations of folate (50.6 µg/100 g). All plants showed variable phenolic content and antioxidant capacity; however, Y. aloifolia had the highest values (23 GAE/mg/g and 440 TEAC/µM/g). The ethanolic extracts from Y. aloifolia efficiently inhibited pancreatic lipase (IC50, 43.76 µg/mL) and alpha-glucosidase (IC50, 60.04 µg/mL), whereas those from S. edule inhibited alpha-glucosidase (IC50, 47.4 µg/mL) and HMG-CoA reductase (IC50, 33.6 µg/mL). Only the ethanolic extracts of R. pompana (IC50, 35.36 µg/mL) and Y. aloifolia (IC50, 53.28 µg/mL) inhibited ornithine decarboxylase. All plant extracts exerted moderated antimicrobial activity in at least one species associated with the gastrointestinal tract.
The leaves of Piper auritum Kunth ('Hoja Santa') have been consumed for centuries by native people of central and southern Mexico as a fresh vegetable or condiment. Herein we present the result of ...the
H-NMR metabolomics profiling of three accessions of P. auritum harvested in three different provinces of Mexico (Puebla, Tlaxcala, and Oaxaca). The volatile content associated with the flavoring properties of the plant was also determined by GC/MS. The non-targeted metabolome of these samples revealed that P. auritum is a source of free essential amino acids such as isoleucine, leucine, threonine, valine, histidine, phenylalanine, and tryptophan as well as organic acids, free monosaccharides, and valuable nutraceuticals such as trigonelline, Myo-inositol, betaine, and choline. Principal component analysis and orthogonal partial least squares discriminated analysis of the metabolites found in P. auritum revealed trigonelline as the main differential compound found in the three studied accessions, suggesting this metabolite as a possible chemical marker. According to these statistical approaches, 60 % of the differential metabolites were provided by Oaxaca samples, suggesting that leaves harvested in this province have better (p<0.05) nutritional properties than the other samples analyzed. Nevertheless, the high abundance of the anti-nutrient safrole (90 %) in the volatile fraction, advises the potential toxicity of P. auritum consumed in Oaxaca. On the other hand, samples harvested in the northern highlands of Puebla, contained the lowest levels of safrole (30 %) and acceptable levels of nutrients and nutraceuticals including choline. From the three groups of studied plants, those harvested in the northern highlands from Puebla, could be considered safer for human consumption than the other analyzed accessions.
The objective of our research was to contrast the resonance techniques on tubers with the more commonly used morphological analyses. With the aims of establishing a classification among ecotypes and ...food fingerprint of mashua tuber, a multivariable data analysis like principal component analysis (PCA) and orthogonal projections to latent structures discriminant analysis (OPLS-DA), were performed with morphological and metabolomic profiling data. Accordingly, the morphological traits showed a clear separation among most of the studied ecotypes. For a 1H NMR metabolic profiling, at least 35 compounds were identified in tubers. The relative concentration of these compounds was used to perform a PCA and OPLS-DA analysis. A clear separation, according to PC1 = 31.7%, was between TTE_01 & TTE_02 and the ecotypes TTE_06 and TTE_05 with significantly higher concentrations of disaccharides such as maltose and sucrose. Amino acids such as proline and alanine were found and organic acid including succinic, fumaric, formic and acetic acid. In contrast, TTE_05 and TTE_06 ecotypes contained higher concentrations of monosaccharides such as fructose, glucose. Metabolic profile demonstrated to be a more reliable technique than morphological analysis for classification of ecotypes.
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•A food fingerprint for six ecotypes of T.tuberosum was determinate by NMR.•Differential metabolites were used to classify and evaluate ecotype similarities.•Classification by differential metabolites match with metabolomic profile (1H NMR).•Metabolic profile is a more reliable than morphological analysis for classification.
Celery is a vegetable widely consumed as a condiment to prepare diverse dishes around the world. Nevertheless, this plant is susceptible to the attack of several phytopathogens including those of the ...Fusarium genus which is translated into devastating losses for the production chain. Herein we report on the metabolic changes produced during the celery wilt caused by Fusarium oxysporum which was determined through untargeted
H-NMR metabolomics. The changes in the metabolite content of celery were measured at 16, 24, and 32 days post-inoculation using viable conidia obtained from the native F. oxysporum strain FO3. Our results demonstrated that the parasitic activity of the fungus reduced the endogenous levels of free sugars (fructose, galactose, glucose isomers, mannose, Myo-inositol, mannitol, and sucrose) amino acids (alanine, aspartate GABA, glutamate, glutamine, histidine, isoleucine, leucine, methionine, proline, threonine, tyrosine, and valine), nucleosides (adenosine, cytidine, guanosine, and uridine) and organic acids (citric acid, fumaric acid, malic acid, and succinic acid). Interestingly, the levels of tyrosine and tryptophan were triggered as a consequence of F. oxysporum infection. This tendency was correlated with an increase in the levels of chlorogenic acid, apiin, and apigenin derivatives, suggesting their involvement in the chemical defense of celery against fungal colonization. According to principal component analysis (PCA) and Orthogonal Projections to Latent Structures Discriminant Analysis (OPLS-DA) methanol was the main differential metabolite and it was considered as a new chemical marker associated with F. oxysporum infection. Our results demonstrate that infected celery plants dramatically reduced their nutritional and nutraceutical contents during Fusarium wilt after 32 days post-inoculation. However, these findings also suggest that the phenylpropanoid pathway is strongly related with the chemical defense of celery against F. oxysporum.
The epigenetic regulation of genes in cancer could be targeted by inhibiting Histone deacetylase 6 (HDAC6), an enzyme involved in several types of cancer such as lymphoma, leukemia, ovarian cancer, ...etc.
Through in silico methods, a set of Phenyl butyric acid derivatives with possible HDAC6 inhibitory activity were designed, rendering monophenylamides and biphenylamides using tubacin (HDAC6 selective inhibitor) as reference.
The target compounds were submitted to theoretical ADMET analyses and their binding properties on different HDAC6 conformers were evaluated through docking calculations.
These in silico studies allowed us to identify a compound named B-R2B. In order to have more information about the B-R2B binding recognition properties on HDAC6, the B-R2B-HDAC6 complex was submitted through 100 ns-long Molecular Dynamics (MD) simulation coupled to MMGBSA approach, revealing that B-R2B is located at the entrance of HDAC6 active pocket, blocking the passage of the substrate without reaching the HDAC6 binding site. Based on these results, B-R2B was synthesized, characterized and biologically tested. The HDAC6 fluorometric drug discovery kit Fluor-de-Lys (ENZO Life Sciences Inc.) was used to determine the HDAC6 human inhibitory activity (IC50 value) of B-R2B compound. In addition, B-R2B show IC50 values on cancer cell lines (HeLa; IC50 = 72.6 µM), acute myeloid leukemia (THP-1; IC50 = 16.5 µM), human mast leukemia (HMC; IC50 = 79.29 µM) and chronic myelogenous leukemia (Kasumi; IC50 = 101 µM).
These results show that B-R2B is a HDAC6 inhibitor, specifically a non-competitive type in a similar way that tubacin does, according to MD simulations.
