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1.
Antibiotics (Basel) ; 12(5)2023 May 08.
Article in English | MEDLINE | ID: mdl-37237772

ABSTRACT

Pest resistance against fungicides is a widespread and increasing problem, with impact on crop production and public health, making the development of new fungicides an urgent need. Chemical analyses of a crude methanol extract (CME) of Guiera senegalensis leaves revealed the presence of sugars, phospholipids, phytosterols, guieranone A, porphyrin-containing compounds, and phenolics. To connect chemical composition with biological effects, solid-phase extraction was used to discard water-soluble compounds with low affinity for the C18 matrix and obtain an ethyl acetate fraction (EAF) that concentrates guieranone A and chlorophylls, and a methanol fraction (MF) dominated by phenolics. While the CME and MF exhibited poor antifungal activity against Aspergillus fumigatus, Fusarium oxysporum and Colletotrichum gloeosporioides, the EAF demonstrated antifungal activity against these filamentous fungi, particularly against C. gloeosporioides. Studies with yeasts revealed that the EAF has strong effectiveness against Saccharomyces cerevisiae, Cryptococcus neoformans and Candida krusei with MICs of 8, 8 and 16 µg/mL, respectively. A combination of in vivo and in vitro studies shows that the EAF can function as a mitochondrial toxin, compromising complexes I and II activities, and as a strong inhibitor of fungal tyrosinase (Ki = 14.40 ± 4.49 µg/mL). Thus, EAF appears to be a promising candidate for the development of new multi-target fungicides.

2.
Molecules ; 28(10)2023 May 16.
Article in English | MEDLINE | ID: mdl-37241874

ABSTRACT

Wheat is critical for food security, and is challenged by biotic stresses, chiefly aphids and the viruses they transmit. The objective of this study was to determine whether aphids feeding on wheat could trigger a defensive plant reaction to oxidative stress that involved plant oxylipins. Plants were grown in chambers with a factorial combination of two nitrogen rates (100% N vs. 20% N in Hoagland solution), and two concentrations of CO2 (400 vs. 700 ppm). The seedlings were challenged with Rhopalosiphum padi or Sitobion avenae for 8 h. Wheat leaves produced phytoprostanes (PhytoPs) of the F1 series, and three types of phytofurans (PhytoFs): ent-16(RS)-13-epi-ST-Δ14-9-PhytoF, ent-16(RS)-9-epi-ST-Δ14-10-PhytoF and ent-9(RS)-12-epi-ST-Δ10-13-PhytoF. The oxylipin levels varied with aphids, but not with other experimental sources of variation. Both Rhopalosiphum padi and Sitobion avenae reduced the concentrations of ent-16(RS)-13-epi-ST-Δ14-9-PhytoF and ent-16(RS)-9-epi-ST-Δ14-10-PhytoF in relation to controls, but had little or no effect on PhytoPs. Our results are consistent with aphids affecting the levels of PUFAs (oxylipin precursors), which decreased the levels of PhytoFs in wheat leaves. Therefore, PhytoFs could be postulated as an early indicator of aphid hosting for this plant species. This is the first report on the quantification of non-enzymatic PhytoFs and PhytoPs in wheat leaves in response to aphids.


Subject(s)
Aphids , Oxylipins , Animals , Aphids/physiology , Triticum , Carbon Dioxide , Plant Leaves
3.
Bioorg Chem ; 138: 106614, 2023 09.
Article in English | MEDLINE | ID: mdl-37216893

ABSTRACT

The inflammatory response is a vital mechanism for repairing damage induced by aberrant health states or external insults; however, persistent activation can be linked to numerous chronic diseases. The nuclear factor kappa ß (NF-κB) inflammatory pathway and its associated mediators have emerged as critical targets for therapeutic interventions aimed at modulating inflammation, necessitating ongoing drug development. Previous studies have reported the inhibitory effect of a hydroethanol extract derived from Parinari excelsa Sabine (Chrysobalanaceae) on tumour necrosis factor-alpha (TNF-α), but the phytoconstituents and mechanisms of action remained elusive. The primary objective of this study was to elucidate the phytochemical composition of P. excelsa stem bark and its role in the mechanisms underpinning its biological activity. Two compounds were detected via HPLC-DAD-ESI(Ion Trap)-MS2 analysis. The predominant compound was isolated and identified as naringenin-8-sulphonate (1), while the identity of the second compound (compound 2) could not be determined. Both compound 1 and the extract were assessed for anti-inflammatory properties using a cell-based inflammation model, in which THP-1-derived macrophages were stimulated with LPS to examine the treatments' effects on various stages of the NF-κB pathway. Compound 1, whose biological activity is reported here for the first time, demonstrated inhibition of NF-κB activity, reduction in interleukin 6 (IL-6), TNF-α, and interleukin 1 beta (IL-1ß) production, as well as a decrease in p65 nuclear translocation in THP-1 cells, thus highlighting the potential role of sulphur substituents in the activity of naringenin (3). To explore the influence of sulphation on the anti-inflammatory properties of naringenin derivatives, we synthesized naringenin-4'-O-sulphate (4) and naringenin-7-O-sulphate (5) and evaluated their anti-inflammatory effects. Naringenin derivatives 4 and 5 did not display potent anti-inflammatory activities; however, compound 4 reduced IL-1ß production, and compound 5 diminished p65 translocation, with both exhibiting the capacity to inhibit TNF-α and IL-6 production. Collectively, the findings demonstrated that the P. excelsa extract was more efficacious than all tested compounds, while providing insights into the role of sulphation in the anti-inflammatory activity of naringenin derivatives.


Subject(s)
Chrysobalanaceae , NF-kappa B , Humans , NF-kappa B/metabolism , Interleukin-6/metabolism , Tumor Necrosis Factor-alpha/metabolism , Chrysobalanaceae/metabolism , Plant Bark/metabolism , Anti-Inflammatory Agents/therapeutic use , Inflammation/metabolism , Plant Extracts/pharmacology , Plant Extracts/therapeutic use , Lipopolysaccharides/pharmacology
4.
Food Res Int ; 167: 112615, 2023 05.
Article in English | MEDLINE | ID: mdl-37087203

ABSTRACT

Kitul (Caryota urens L.) inflorescences are broadly used for sweet sap production in Asian countries and Kitul food products are known as being suitable for diabetic patients. Considering the strong ability to inhibit α-glucosidase, we hypothesize that kitul antidiabetic properties might also involve the modulation of inflammatory pathways and hyperglycaemia-induced oxidative damage. Hence, the effects of an inflorescence's methanol extract were investigated in glucose-stimulated pancreatic cells (RIN-5F) and LPS-stimulated RAW 264.7 macrophages. The extract reduced the overproduction of intracellular reactive species in pancreatic cells and also NO, L-citrulline and IL-6 levels in LPS-stimulated RAW 264.7 macrophages. Inhibition of 5-lipoxygenase (IC50 = 166.1 µg/mL) through an uncompetitive manner was also recorded upon treatment with C. urens inflorescences extract. The phenolic profile of the inflorescences was characterized by HPLC-DAD, six hydroxycinnamic acids being identified and quantified. Overall, our data provide additional evidence on the pleiotropic mechanisms of Kitul inflorescences as an antidiabetic agent.


Subject(s)
Glucose , Plant Extracts , Humans , Mice , Animals , RAW 264.7 Cells , Plant Extracts/pharmacology , Plant Extracts/metabolism , Glucose/metabolism , Hypoglycemic Agents/pharmacology , Hypoglycemic Agents/metabolism , Inflammation Mediators/metabolism , Lipopolysaccharides/pharmacology , Anti-Inflammatory Agents/pharmacology , Anti-Inflammatory Agents/metabolism , Macrophages , Plants, Edible/metabolism
5.
Foods ; 12(6)2023 Mar 11.
Article in English | MEDLINE | ID: mdl-36981113

ABSTRACT

Borututu (Cochlospermum angolense Welw.) roots have been described as a rich source of phenolic compounds. Despite the potential of this plant for the production of bioactive extracts, studies reported until now have been scarce, and they have been based on the use of inefficient conventional extraction techniques. In this study, pressurized liquid extraction (PLE) was investigated for the production of borututu root extracts. Different temperatures (50-200 °C) and solvents (water, ethanol, and 50% ethanol:water) were applied. The total phenolic compound (TPC) content, the main phenolic compounds and the in vitro antioxidant activity of the extracts were evaluated. The results were compared with those obtained by conventional decoction with water. The highest concentrations of TPC and antioxidant activity were obtained with 50% ethanol:water, followed by water. The extract obtained with 50% ethanol:water at 150 °C had a TPC concentration of 343.80 mg/g and presented the largest antioxidant activity (1488 and 4979 µmol Trolox/g extract, determined by DDPH and ABTS assay, respectively). These values were considerably higher than those obtained by conventional decoction. Ellagic acid, and ellagic and methyl ellagic acid glycosides were the main phenolic compounds found in the extracts. Therefore, was PLE demonstrated to be a selective and efficient technique to obtain extracts with high concentrations of phenolic compounds and high antioxidant activity form borututu roots.

6.
Life (Basel) ; 13(2)2023 Feb 01.
Article in English | MEDLINE | ID: mdl-36836763

ABSTRACT

The present work aimed to detail the mechanisms elicited by Allophylus africanus P. Beauv. stem bark extract in human stomach cancer cells and to identify the bioactives underlying the cytotoxicity. MTT reduction and LDH leakage assays allowed characterizing the cytotoxic effects in AGS cells, which were further detailed by morphological analysis using phalloidin and Hoechst 33258. Proapoptotic mechanisms were elucidated through a mitochondrial membrane potential assay and by assessing the impact upon the activity of caspase-9 and -3. The extract displayed selective cytotoxicity against AGS cells. The absence of plasma membrane permeabilization, along with apoptotic body formation, suggested that pro-apoptotic effects triggered cell death. Intrinsic apoptosis pathway activation was verified, as mitochondrial membrane potential decrease and activation of caspase-9 and -3 were observed. HPLC-DAD profiling enabled the identification of two apigenin-di-C-glycosides, vicenin-2 (1) and apigenin-6-C-hexoside-8-C-pentoside (3), as well as three mono-C-glycosides-O-glycosylated derivatives, apigenin-7-O-hexoside-8-C-hexoside (2), apigenin-8-C-(2-rhamnosyl)hexoside (4) and apigenin-6-C-(2-rhamnosyl)hexoside (5). Isovitexin-2″-O-rhamnoside (5) is the main constituent, accounting for nearly 40% of the total quantifiable flavonoid content. Our results allowed us to establish the relationship between the presence of vicenin-2 and other apigenin derivatives with the contribution to the cytotoxic effects on the presented AGS cells. Our findings attest the anticancer potential of A. africanus stem bark against gastric adenocarcinoma, calling for studies to develop herbal-based products and/or the use of apigenin derivatives in chemotherapeutic drug development.

7.
Food Res Int ; 155: 111082, 2022 05.
Article in English | MEDLINE | ID: mdl-35400458

ABSTRACT

Among several extracts from species from Guinea-Bissauan flora, the hydroethanol extract obtained from the leaves of gingerbread plum (Neocarya macrophylla (Sabine) Prance ex F. White.) revealed to be one of the most cytotoxic towards human gastric AGS carcinoma cells. Considering the increasing use of N. macrophylla in the food industry and the abundant biomass of agricultural wastes being generated, the identification of phenolic bioactives has been attained by HPLC-DAD-ESI/MSn and UHPLC-ESI/QTOF/MSn. Twenty-seven phenolic constituents were identified for the first time in the monotypic genus Neosartorya, 5-O-caffeoylquinic acid being detected as the major constituent (4.90 ± 0.20 mg g-1 dry extract). While 15 flavan-3-ols derivatives were determined, the extract is predominantly characterized by the occurrence of quercetin, kaempferol, apigenin and chrysoeriol glycosides. Typical apoptotic changes in gastric adenocarcinoma AGS cells upon exposure to N. macrophylla leaf extract were observed. The apoptotic cell death is mediated by the activation of the mitochondrial pathway, as loss of mitochondrial membrane potential was detected, as well as increased caspase-9 and -3 activities. The industrial relevance of this plant material, along with the data presented here on the potential anticancer effects of N. macrophylla and the efficient extraction of phenolic bioactives using water and ethanol (GRAS substance), calls for further research on the leaves as a potential functional food and/or ingredient.


Subject(s)
Carcinoma , Chrysobalanaceae , Chromatography, High Pressure Liquid , Humans , Phenols/analysis , Phenols/pharmacology , Plant Extracts/pharmacology , Polyphenols/pharmacology , Spectrometry, Mass, Electrospray Ionization
8.
J Agric Food Chem ; 69(47): 14165-14175, 2021 Dec 01.
Article in English | MEDLINE | ID: mdl-34797062

ABSTRACT

Recently, new bioactive compounds were identified in olive oil, lipophenols, which are composed of a fatty acid (FA) and a phenolic core, such as HT (HT-FA). However, their bioaccessibility remains unknown. Thus, the present study uncovers the impact of the separate phases of gastrointestinal digestion on the release and stability of HT-FAs from oily matrices under in vitro simulated conditions. Accordingly, it was found that the bioaccessibility of HT derivatives is largely dependent on the type of FA that esterifies HT, as well as the food matrix. Also, the generation of HT-FAs during intestinal digestion was observed, with pancreatin being the enzyme responsible, to a higher extent, for the de novo formation of lipophenolic derivatives. These findings prompt us to identify new applications to oily matrices and their byproducts as potential functional ingredients for the promotion of health, where the possible formation of new lipophenols during digestion should be taken into consideration.


Subject(s)
Fatty Acids , Plant Oils , Biological Availability , Digestion , Esters , Olive Oil
9.
Nutrients ; 13(7)2021 Jul 13.
Article in English | MEDLINE | ID: mdl-34371907

ABSTRACT

The effect of coffee and cocoa on oxidative damage to macromolecules has been investigated in several studies, often with controversial results. This study aimed to investigate the effect of one-month consumption of different doses of coffee or cocoa-based products containing coffee on markers of DNA damage and lipid peroxidation in young healthy volunteers. Twenty-one volunteers were randomly assigned into a three-arm, crossover, randomized trial. Subjects were assigned to consume one of the three following treatments: one cup of espresso coffee/day (1C), three cups of espresso coffee/day (3C), and one cup of espresso coffee plus two cocoa-based products containing coffee (PC) twice per day for 1 month. At the end of each treatment, blood samples were collected for the analysis of endogenous and H2O2-induced DNA damage and DNA oxidation catabolites, while urines were used for the analysis of oxylipins. On the whole, four DNA catabolites (cyclic guanosine monophosphate (cGMP), 8-OH-2'-deoxy-guanosine, 8-OH-guanine, and 8-NO2-cGMP) were detected in plasma samples following the one-month intervention. No significant modulation of DNA and lipid damage markers was documented among groups, apart from an effect of time for DNA strand breaks and some markers of lipid peroxidation. In conclusion, the consumption of coffee and cocoa-based confectionery containing coffee was apparently not able to affect oxidative stress markers. More studies are encouraged to better explain the findings obtained and to understand the impact of different dosages of these products on specific target groups.


Subject(s)
Biomarkers/blood , Chocolate , Coffee , DNA Damage , Lipid Peroxidation , Oxidative Stress , 8-Hydroxy-2'-Deoxyguanosine/blood , Chocolate/adverse effects , Chromatography, High Pressure Liquid , Coffee/adverse effects , Comet Assay , Cross-Over Studies , Cyclic GMP/analogs & derivatives , Cyclic GMP/blood , Female , Guanine/analogs & derivatives , Guanine/blood , Humans , Male , Tandem Mass Spectrometry , Young Adult
10.
Food Res Int ; 141: 110121, 2021 03.
Article in English | MEDLINE | ID: mdl-33641988

ABSTRACT

While the fruits of Xylopia aethiopica (Dunal) A. Rich. are important in African countries as a local trade product, their composition remains scarcely investigated. Phenolic fingerprint is herein delivered through HPLC-DAD-ESI(Ion Trap)-MSn and UPLC-ESI-QTOF-MS2 analysis, six cinnamoylquinic acid derivatives and twenty-four flavonoid glycosides being determined, chrysoeriol-7-O-glycosides being the main constituents. A cytotoxicity screening of twenty-eight hydroethanol extracts, obtained from a collection of Guinea-Bissauan plants, against A549 and AGS carcinoma cells, revealed the selective and potent effect towards AGS cells (IC50 = 151 × 10-3 g L-1), upon exposure to the extract from X. aethiopica fruits. Additional experiments demonstrated insignificant effect on LDH release at 151 × 10-3 g L-1, morphological analysis further suggesting induction of apoptosis. Pro-apoptotic effects were confirmed, as the extract enabled the activation of the effector caspase-3, broadening the knowledge on the anticancer mechanisms elicited by the fruits of X. aethiopica. Phenolic constituents might contribute to the cytotoxic effects, particularly via caspase-3 activation. Considering that X. aethiopica fruit is very often referred as an anticancer ingredient in Africa, but mainly the potent cytotoxicity herein recorded, our results call for additional research aiming to identify non-phenolic constituents contributing to the effects and also to further detail the anticancer mechanisms.


Subject(s)
Adenocarcinoma , Xylopia , Africa , Caspase 3 , Chromatography, High Pressure Liquid , Fruit , Plant Extracts/pharmacology , Stomach Neoplasms
11.
J Ethnopharmacol ; 269: 113746, 2021 Apr 06.
Article in English | MEDLINE | ID: mdl-33359184

ABSTRACT

ETHNOPHARMACOLOGICAL RELEVANCE: According to ethnobotanical surveys, Cassia sieberiana DC. (1825) is a particularly reputed species in African folk Medicine, namely due to the application of its leaves and roots for the treatment of diseases and symptomatology that appear to be related with an inflammatory background. In contrast with the roots of the plant, the leaves remain to be investigated, which prompted us to further detail mechanisms underlying their anti-inflammatory properties, by using in vitro models of disease. AIM OF THE STUDY: Considering its use in the amelioration and treatment of conditions that frequently underlie an inflammatory response, C. sieberiana leaves extract was prioritized amongst a collection of extracts obtained from plants collected in Guinea-Bissau. As such, this work aims to deliver experimental data on the anti-inflammatory properties of C. sieberiana leaf and to establish possible associations with its chemical composition, thus providing a rationale on its use in folk Medicine. MATERIALS AND METHODS: The chemical profile of an hydroethanol extract obtained from the leaves of the plant was established by HPLC-DAD-ESI/MSn in order to identify bioactives. The extract and its main compound were tested towards a series of inflammatory mediators, both in enzymatic and cell-based models. The capacity to interfere with the eicosanoid-metabolizing enzymes 5-lipoxygenase (5-LOX), cyclooxygenase-1 (COX-1) and -2 (COX-2) was evaluated in cell-free systems, while the effects in interleukin 6 (IL-6) and tumour necrosis factor-α (TNF-α) levels produced by THP-1 derived macrophages were assessed through ELISA. RESULTS: HPLC-DAD-ESI/MSn analysis of the extract elucidated a chemical profile qualitatively characterized by a series of anthraquinones, particularly rhein derivatives, and nine flavonols, most of which 3-O-glycosylated. Considering the concentrations of the identified compounds, quercetin was detached as the main component. Effects of the hydroethanol extract obtained from C. sieberiana leaves against key enzymes of the arachidonic acid cascade were recorded, namely a concentration-dependent inhibition against 5-LOX, at concentrations ranging from 16 to 250 µg mL-1 and a selective inhibitory action upon COX-2 (IC50 = 3.58 µg mL-1) in comparison with the isoform COX-1 (IC50 = 9.10 µg mL-1). Impact on inflammatory cytokines was also noted, C. sieberiana leaf extract significantly decreasing IL-6 levels in THP-1 derived macrophages at 250 and 500 µg mL-1. In contrast, TNF-α levels were found to be increased in the same model. Quercetin appears to partially account for the observed effects, namely due to the significant inhibitory effects on the activity of the arachidonic acid metabolizing enzymes COX-2 and 5-LOX. CONCLUSIONS: The anti-inflammatory effects herein reported provide a rationale for the use of C. sieberiana leaves in African folk practices, such as in the treatment of arthritis, rheumatism and body aches. Considering the occurrence of flavonoidic and anthraquinonic constituents, as well as the observed anti-inflammatory properties of quercetin, recorded effects must be related with the presence of several bioactives.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Cassia/chemistry , Enzyme Inhibitors/pharmacology , Inflammation/drug therapy , Plant Extracts/pharmacology , Anthraquinones/chemistry , Anti-Inflammatory Agents/chemistry , Cyclooxygenase 1/drug effects , Cyclooxygenase 2/drug effects , Cytokines/antagonists & inhibitors , Eicosanoids/metabolism , Enzyme Inhibitors/chemistry , Flavonoids/chemistry , Flavonoids/pharmacology , Guinea-Bissau , Humans , Inflammation/chemically induced , Lipopolysaccharides/toxicity , Medicine, Traditional , Phenols/chemistry , Plant Extracts/chemistry , Plant Leaves/chemistry , THP-1 Cells
12.
Eur J Nutr ; 60(2): 905-915, 2021 Mar.
Article in English | MEDLINE | ID: mdl-32524230

ABSTRACT

PURPOSE: Several studies have demonstrated the properties of hydroxytyrosol, a phenolic compound present in olive oils and olives with a well-characterized impact on human health. Nevertheless, some knowledge gaps remain on its bioavailability and metabolism; overall concerning to the real rate per cent of absorption and biovailability of dietary hydroxytyrosol and the influence of the dietary food-containing hydroxytyrosol on it. METHODS: A double-blind study was performed including 20 volunteers who ingested 5 mg of hydroxytyrosol through diverse food matrices, to discover the influence on pharmacokinetics and bioavailability of HT metabolites (hydroxytyrosol acetate, 3,4-dihydroxyphenylacetic acid (DOPAC), tyrosol, and homovanillic alcohol) of the distinct matrices by UHPLC-ESI-QqQ-MS/MS. RESULTS: The HT pharmacokinetics after consumption of different food matrices was strongly dependent on the food matrix. In this aspect, the intake of extra virgin olive exhibited significantly higher plasma concentrations after 30 min of oral intake (3.79 ng/mL) relative to the control. Regarding the hydroxytyrosol bioavailability, the intake of extra virgin olive oil, as well as fortified refined olive, flax, and grapeseed oils provided significantly higher urinary contents (0.86, 0.63, 0.55, and 0.33 µg/mg creatinine, respectively) compared with basal urine, whereas hydroxytyrosol metabolites showed no significant changes. No differences were found between men and women. CONCLUSIONS: The metabolic profile of hydroxytyrosol is influenced by the food matrix in which is incorporated, with the oily nature for the final bioavailability being relevant. Extra virgin olive oil was identified as the best matrix for this compound. The results described contribute to the understanding of the relevance of the food matrices for the final absorption of hydroxytyrosol and hence, the achievement of the highest health protection potential.


Subject(s)
Olea , Phenylethyl Alcohol , Biological Availability , Female , Humans , Male , Olive Oil , Phenylethyl Alcohol/analogs & derivatives , Plant Oils , Tandem Mass Spectrometry
13.
Plants (Basel) ; 11(1)2021 Dec 23.
Article in English | MEDLINE | ID: mdl-35009040

ABSTRACT

This work aimed to identify the bioactive compounds present in adult maqui (Aristotelia chilensis) leaves from different stages of development and seasons of the year and compare them with leaves obtained from maqui plants grown in vitro. The qualitative and quantitative analysis of maqui leaf extracts by HPLC-DAD-ESI-MSn showed the presence of different polyphenolic compounds classified into galloyl and caffeoyl quinic acids, ellagitannins and ellagic acid- and flavonoid-derivatives. In general, the total phenolic content of the in vitro samples was higher than that of ex vitro samples, whereas the total flavonoid content was higher in winter basal leaves. Additionally, the analysis by HPLC-MS showed that the extract from spring basal leaves was enriched in quercetin, catechin, kaempferol and 3-caffeoyl quinic acids, while in the in vitro leaves extract, quercetin was not present. As regards lipophilic compounds identified by GC/MS, the samples of in vitro leaves showed a high presence of α-tocopherol and ß-sitosterol. In contrast, the samples of adult leaves presented a hight level of linolenic and linoleic acids. These results suggest that maqui leaves could be an excellent source of antioxidants and lipophilic compounds for many industries, such as the nutraceutical and pharmaceutical industries.

14.
Food Chem ; 342: 128323, 2021 Apr 16.
Article in English | MEDLINE | ID: mdl-33069534

ABSTRACT

Caryota urens L. has long been valued as a traditional food, the edible fruits being eaten raw and the inflorescences commonly used on sweet sap and flour production. In the current work, the phenolic profile of methanol extracts obtained from the inflorescences and fruits was unveiled for the first time, nine caffeic acid derivatives being identified and quantified. Since kitul products have been reported for their antidiabetic properties, extracts radical scavenging activity and α-amylase, α-glucosidase and aldose reductase inhibitory activity were assessed. The inflorescences' extract was particularly active against yeast α-glucosidase (IC50 = 1.53 µg/mL), acting through a non-competitive inhibitory mechanism. This activity was also observed in enzyme-enriched homogenates obtained from human Caco-2 cells (IC50 = 64.75 µg/mL). Additionally, the extract obtained from the inflorescences showed no cytotoxicity on HepG2, AGS and Caco-2 cell lines. Our data suggest that C. urens inflorescences can support the development of new functional foods with α-glucosidase inhibitory activity.


Subject(s)
Fruit/metabolism , Inflorescence/metabolism , Plants, Edible/metabolism , Caco-2 Cells , Caffeic Acids , Glycoside Hydrolase Inhibitors/pharmacology , Humans , Hypoglycemic Agents/pharmacology , Phenols/analysis , Plant Extracts/pharmacology , alpha-Amylases/antagonists & inhibitors , alpha-Glucosidases/metabolism
15.
Food Res Int ; 137: 109694, 2020 11.
Article in English | MEDLINE | ID: mdl-33233268

ABSTRACT

Notwithstanding Gustavia gracillima Miers widespread distribution in neotropical regions, its chemical profile and biological properties remain uninvestigated. A methanol extract obtained from the flowers was characterized through HPLC-DAD-ESI/MSn, nine ellagic acid derivatives and twelve kaempferol 3-O-glycosides being identified and quantitated for the first time at the species and genus. Preliminary cytotoxicity screening did not reveal noticeable effects upon gastrointestinal representative cell lines (AGS, Caco-2 and Hep G2), which further prompted us to evaluate the impact in a series of targets involved in metabolic disorders and associated complications. Despite of the moderate inhibition towards 5-lipoxygense activity, G. gracillima methanol extract displayed significant effects on carbohydrates-hydrolysing enzymes. In contrast with the antidiabetic reference drug acarbose, the extract was able to selectively inhibit yeast α-glucosidase activity (IC50 = 4.72 µg/mL), with negligible inhibitory effects upon α-amylase. Kinetic studies pointed to a model of mixed inhibition with a great binding activity, characterized by an inhibitory constant of 2.91 µg/mL. The notable inhibitory activity was also confirmed in α-glucosidase homogenates isolated from human intestinal cells (IC50 = 34.03 µg/mL). Moreover, the extract obtained from the flowers of G. gracillima displayed significant aldose reductase inhibition (IC50 = 61.88 µg/mL), as well as O2- and NO scavenging properties. A moderate inhibitory effect was also recorded against pancreatic lipase (IC50 = 362.17 µg/mL) through a mixed inhibition mode. Recorded data supports the potential incorporation of G. gracillima flowers on antidiabetic herbal formulations and/or supplements, with not only straight action on carbohydrates digestion, but also direct interference with targets involved on subsequent diabetes events, such as triglycerides metabolism, inflammation and radical-mediated stress.


Subject(s)
Antioxidants , Plant Extracts , Antioxidants/pharmacology , Caco-2 Cells , Chromatography, High Pressure Liquid , Enzyme Inhibitors , Flowers , Humans , Kinetics , Plant Extracts/pharmacology
16.
Food Chem ; 333: 127456, 2020 Dec 15.
Article in English | MEDLINE | ID: mdl-32663750

ABSTRACT

Bioprospecting for seaweed-derived multimodal acting products have earned increasing attention in the fight against diseases of multifactorial origin, such as neurodegenerative conditions. This is a pioneer study on the in vitro screening of neuroactive properties of phlorotannin-targeted extracts from edible Fucus species. Phlorotannin extracts exhibited multifunctional antioxidant properties, which were suggested to be responsible for counteracting glutamate toxicity in neuronal human-derived SH-SY5Y cells. They also inhibited the activity of enzymes (cholinesterases, monoaminoxidases A and B, and tyrosinase) linked to a set of events that contribute to the onset/progression of neurodegeneration. In general, the bioactivities were correlated with the total phlorotannin content and phloroglucinol tetramers were suggested to be behind the observed effects. The capacity of the phlorotannin extracts to interact with multiple in vitro targets underpinning neurodegeneration points to the potential interest of the selected seaweed species for development of new added-value products and promising neuroactive agents.


Subject(s)
Antioxidants/chemistry , Antioxidants/pharmacology , Fucus/chemistry , Neuroprotective Agents/chemistry , Neuroprotective Agents/pharmacology , Cell Line , Drug Evaluation, Preclinical/methods , Enzyme Inhibitors/chemistry , Enzyme Inhibitors/pharmacology , Food , Glutamic Acid/toxicity , Humans , Lipid Peroxidation/drug effects , Neurodegenerative Diseases/drug therapy , Neurons/drug effects , Phloroglucinol/chemistry , Phloroglucinol/pharmacology , Polyphenols/chemistry , Polyphenols/pharmacology , Principal Component Analysis , Seaweed/chemistry
17.
J Agric Food Chem ; 68(33): 8915-8924, 2020 Aug 19.
Article in English | MEDLINE | ID: mdl-32683865

ABSTRACT

Pistachio (Pistacia vera L.) is a drought-tolerant species grown under the semiarid conditions of the Mediterranean basin. For this reason, it is essential to make an exhaustive quantification of yield and quality benefits of the kernels because the regulated deficit irrigation will allow significant water savings with a minimum impact on yield while improving kernel quality. The goal of this scientific work was to study the influence of the rootstock, water deficit during pit hardening, and kernel roasting on pistachio (P. vera, cv. Kerman) fruit yield, fruit size, and kernel content of fatty acids phytoprostanes (PhytoPs) and phytofurans (PhytoFs) for the first time. Water stress during pit hardening did not affect the pistachio yield. The kernel cultivar showed a lower oleic acid and a higher linoleic acid contents than other cultivars. Kernels from plants grafted on the studied rootstocks showed very interesting characteristics. P. integerrima led to the highest percentage of monounsaturated fatty acids. Regarding the plant oxylipins, P. terebinthus led to the highest contents of PhytoPs and PhytoFs (1260 ng/100 g and 16.2 ng/100 g, respectively). In addition, nuts from trees cultivated under intermediate water deficit during pit hardening showed increased contents of the 9-series F1-phytoprostanes and ent-16(RS)-9-epi-ST-Δ14-10-phytofuran. However, roasting of pistachios led to PhytoP degradation. Therefore, plant cultivar, deficit irrigation, rootstock, and roasting must be considered to enhance biosynthesis of these secondary metabolites. New tools using agricultural strategies to produce hydroSOS pistachios have been opened thanks to the biological properties of these prostaglandin-like compounds linking agriculture, nutrition, and food science technology for further research initiatives.


Subject(s)
Fatty Acids/chemistry , Furans/chemistry , Pistacia/metabolism , Plant Extracts/chemistry , Seeds/chemistry , Agricultural Irrigation , Cooking , Fatty Acids/metabolism , Furans/metabolism , Pistacia/chemistry , Pistacia/growth & development , Plant Extracts/metabolism , Plant Roots/chemistry , Plant Roots/growth & development , Plant Roots/metabolism , Seeds/growth & development , Seeds/metabolism , Water/metabolism
18.
J Agric Food Chem ; 68(29): 7789-7799, 2020 Jul 22.
Article in English | MEDLINE | ID: mdl-32603105

ABSTRACT

Lipophenols have been stressed as an emerging class of functional compounds. However, little is known about their diversity. Thus, this study is aimed at developing a new method for the extraction, cleanup, and ultrahigh-performance liquid chromatography-electrospray ionization-triple quadrupole mass spectrometry (UHPLC-ESI-QqQ-MS/MS)-based analysis of the lipophenols derived from hydroxytyrosol (HT): α-linolenic (HT-ALA), linoleic acid (HT-LA), and oleic acid (HT-OA). The method validated provides reliable analytical data and practical applications. It was applied to an array of oily (extra virgin olive oil, refined olive oil, flaxseed oil, grapeseed oil, and margarine) and aqueous (pineapple juice) matrices, nonfortified and fortified with HT. Also, the present work reported the formation of fatty acid esters of HT (HT-FAs) that seem to be closely dependent on the fatty acid profile of the food matrix, encouraging the further exploration of the theoretical basis for the generation of HT-FAs, as well as their contribution to the healthy attributions of plant-based foods.


Subject(s)
Fatty Acids/chemistry , Food, Fortified/analysis , Phenylethyl Alcohol/analogs & derivatives , Plant Oils/chemistry , Cell Survival/drug effects , Chromatography, High Pressure Liquid , Fatty Acids/pharmacology , Humans , Lipidomics , Phenylethyl Alcohol/chemistry , Phenylethyl Alcohol/pharmacology , Plant Oils/pharmacology , Tandem Mass Spectrometry
19.
Antioxidants (Basel) ; 9(6)2020 Jun 10.
Article in English | MEDLINE | ID: mdl-32532110

ABSTRACT

The potential use as food ingredients of 12 commercial seed species belonging to the Lamiaceae family constitutes the main goal of this research. For that, the oil yield, the lipid profile, tocopherol content, phenolic profile and antioxidant capacities were determined. Seeds from Satureja hortensis, S. montana, Lavandula angustifolia, L. latifolia and Origanum vulgare can be considered as important sources of ω-3 polyunsaturated fatty acids (50.5; 52.4; 52.1; 48.5 and 45.5 g/100 g, respectively), likewise for seed oils from Salvia lavandulifolia and Rosmarinus officinalis regarding ω-6 polyunsaturated fatty acids (52.2 and 50.0 g/100 g, respectively). The total tocopherol concentration varied between 42.8 and 113.8 mg/100 g of oil. The highest antioxidant capacities corresponded to Thymbra capitata and Origanum vulgare seed oils, in which carvacrol was the major phenolic monoterpene quantified. The presence of cinnamoyl-apigenin derivatives and hydroxycoumarin-apigenin-derivatives in spike lavender is described for the first time. Most of these seeds can be considered as an important source of oil rich in bioactive components of interest for human nutrition.

20.
Free Radic Biol Med ; 146: 340-349, 2020 01.
Article in English | MEDLINE | ID: mdl-31734358

ABSTRACT

Oxylipins such as isoprostanes (IsoPs), prostaglandins (PGs) and thromboxanes (TXs) are lipid mediators derived from the oxidation of polyunsaturated fatty acids, which regulate the magnitude of oxidative stress and inflammation processes and play an important role in pathophysiological processes in the kidney. A total of 36 oxylipins were analyzed by UHPLC-QqQ-MS/MS in the urine of 41 renal recipients from cadaveric donors of the Nephrology Unit of the University Hospital Virgen de la Arrixaca during the first six months after renal transplantation, in order to investigate several candidate oxylipins as more accurate and predictive biomarkers in renal transplantation than classical biological variables. A decrease in nine PGs, mostly from the AA-D pathway (p < 0.05) and one IsoP: 15-keto-15-F2t-IsoP (p < 0.001) was observed. Moreover, two PGs (2,3-dinor-11ß-PGF2α and 17-trans-PGF3α) increased between five days and six months after renal transplantation (p < 0.05). In addition, when kidney function improved, a positive correlation between oxylipin levels and the excretion of urine proteins was observed. These results suggest that oxylipins could be useful markers for monitoring renal function in the post-renal transplantation period. These findings could be of utility not only for the development of strategies for long-term preservation of graft function, but also for innovative and alternative therapies -using oxylipins as predictive markers-to avoid organ rejection.


Subject(s)
Kidney Transplantation , Oxylipins , Allografts , Biomarkers , Humans , Kidney Transplantation/adverse effects , Tandem Mass Spectrometry
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