RESUMEN

4-Coumarate-CoA Ligase (4CL) is an important enzyme in the phenylpropanoid biosynthesis pathway. Multiple 4CLs are identified in Ocimum species; however, their in planta functions remain enigmatic. In this study, we independently overexpressed three Ok4CL isoforms from Ocimum kilimandscharicum (Ok4CL7, -11, and -15) in Nicotiana benthamiana. Interestingly, Ok4CL11 overexpression (OE) caused a rootless or reduced root growth phenotype, whereas overexpression of Ok4CL15 produced normal adventitious root (AR) growth. Ok4CL11 overexpression in N. benthamiana resulted in upregulation of genes involved in flavonoid biosynthesis and associated glycosyltransferases accompanied by accumulation of specific flavonoid-glycosides (kaempferol-3-rhamnoside, kaempferol-3,7-O-bis-alpha-l-rhamnoside [K3,7R], and quercetin-3-O-rutinoside) that possibly reduced auxin levels in plants, and such effects were not seen for Ok4CL7 and -15. Docking analysis suggested that auxin transporters (PINs/LAXs) have higher binding affinity to these specific flavonoid-glycosides, and thus could disrupt auxin transport/signaling, which cumulatively resulted in a rootless phenotype. Reduced auxin levels, increased K3,7R in the middle and basal stem sections, and grafting experiments (intra and inter-species) indicated a disruption of auxin transport by K3,7R and its negative effect on AR development. Supplementation of flavonoids and the specific glycosides accumulated by Ok4CL11-OE to the wild-type N. benthamiana explants delayed the AR emergence and also inhibited AR growth. While overexpression of all three Ok4CLs increased lignin accumulation, flavonoids, and their specific glycosides were accumulated only in Ok4CL11-OE lines. In summary, our study reveals unique indirect function of Ok4CL11 to increase specific flavonoids and their glycosides, which are negative regulators of root growth, likely involved in inhibition of auxin transport and signaling.

Asunto(s)

Flavonoides , Glicósidos , Nicotiana , Proteínas de Plantas , Raíces de Plantas , Flavonoides/metabolismo , Raíces de Plantas/crecimiento & desarrollo , Raíces de Plantas/metabolismo , Raíces de Plantas/genética , Glicósidos/metabolismo , Proteínas de Plantas/metabolismo , Proteínas de Plantas/genética , Nicotiana/genética , Nicotiana/crecimiento & desarrollo , Nicotiana/metabolismo , Regulación de la Expresión Génica de las Plantas , Plantas Modificadas Genéticamente , Coenzima A Ligasas/metabolismo , Coenzima A Ligasas/genética

RESUMEN

BACKGROUND: Despite the heightened threat to unforeseen nuclear/radiological exposures worldwide, no countermeasures are currently approved to prevent gastrointestinal (GI) toxicity induced by radiation in humans. PURPOSE: In this study, we aim to establish the gastroprotective role of flavonoid, Quercetin-3-O-rutinoside (Q-3-R) against 7.5 Gy total body gamma radiation dose that contributes to the hematopoietic syndrome. METHODS: Q-3-R (10 mg/kg body weight) was administered intramuscularly to C57BL/6 male mice before exposure to 7.5 Gy and monitored for morbidity and mortality. The GI protection against radiation was ascertained by histopathological and xylose absorption studies. Intestinal apoptosis, crypt proliferation and apoptotic signaling were also investigated in different treatment groups. RESULTS: We found that Q-3-R prevented the radiation-induced loss of mitochondrial membrane potential, maintained ATP levels, regulated the apoptotic pathway, and activated crypt cell proliferation in the intestine. Radiation-induced villi and crypt damage as well as mal-absorption were significantly minimized in the Q-3-R treated group. We observed 100% survival post Q-3-R administration against 33.3% lethality in 7.5 Gy (LD33.3/30) exposed C57BL/6 mice. The Q-3-R pre-treated mice that survived the 7.5 Gy dose revealed no pathological changes related to the development of fibrosis in the intestine and thickened mucosal wall till 4 months post irradiation. Complete hematopoietic recovery was observed in these surviving mice when compared to age matched control. CONCLUSION: The findings revealed that Q-3-R regulated the apoptotic process to achieve GI protection against LD33.3/30 dose (7.5 Gy) that primarily caused death due to hematopoietic failure. The recovery observed in mice survivors suggested that this molecule may also have the potential to minimize side effects on normal tissues during radiotherapy.

Asunto(s)

Flavonoides , Quercetina , Humanos , Masculino , Animales , Ratones , Ratones Endogámicos C57BL , Quercetina/farmacología , Apoptosis

RESUMEN

BACKGROUND: Oxidation is a major problem for oils and fats, which can be mitigated by antioxidants. Rutin has excellent antioxidant activity, but its poor lipid solubility greatly limits its practical application. In this study, an efficient enzymatic synthesis route of lipophilic rutin ester was established using oleic acid as an acyl donor, and the antioxidant potential of rutin oleate was evaluated for the first time by proton (1 H) nuclear magnetic resonance (NMR) spectroscopy. RESULTS: The synthesized product was finally identified as rutin oleate by Fourier transform infrared, high-performance liquid chromatography-mass spectrometry, and 1 H, carbon-13, and DEPT-135 NMR analyses, and the acylation site was the 4‴-OH of the rhamnose group in the rutin molecule. The maximum conversion was over 93% after 48 h of reaction using Novozym 435 as catalyst under the best conditions among these tests. The conversion of rutin ester decreased with the increase of carbon chain length and the number of carbon-carbon double bonds of the fatty acid molecule. Most importantly, rutin oleate exhibited antioxidant capacity comparable to butylated hydroxytoluene and its counterparts (rutin and oleic acid) at low temperatures (60° C), but had a significant advantage at high temperatures (120° C). CONCLUSION: The antioxidant activity of rutin was significantly enhanced by lipase-mediated esterification with oleic acid. Therefore, rutin oleate could be further developed as a novel antioxidant for use in oil- and fat-based foods. © 2023 Society of Chemical Industry.

Asunto(s)

Antioxidantes , Rutina , Antioxidantes/química , Ácido Oléico/química , Lipasa/química , Carbono/química , Ésteres , Aceites

RESUMEN

Berries are rich food sources of potentially health-beneficial (poly)phenols. However, they may undergo chemical modifications during gastrointestinal digestion. The effect of simulated gastrointestinal digestion on the content and composition of secondary metabolites from Gaultheria phillyreifolia and G. poeppigii berries was studied. The influence of the digested extracts on the in vitro metabolism and absorption of carbohydrates was evaluated. After simulated digestion, 31 compounds were detected by UHPLC-DAD-MS. The total content of anthocyanins decreased by 98-100%, flavonols by 44-56%, phenylpropanoids by 49-75% and iridoids by 33-45%, the latter showing the highest stability during digestion. Digested extracts inhibited α-glucosidase (IC50 2.8-24.9 µg/mL) and decreased the glucose uptake in Caco-2 cells by 17-28%. Moreover, a decrease in the mRNA expression of glucose transporters SGLT1 (38-92%), GLUT2 (45-96%), GLUT5 (28-89%) and the enzyme sucrase-isomaltase (82-97%) was observed. These results show the effect of simulated gastrointestinal digestion on the content and composition of Gaultheria berries.

Asunto(s)

Gaultheria , Polifenoles , Antocianinas , Antioxidantes , Células CACO-2 , Digestión , Frutas/química , Glucosa , Humanos , Iridoides , Extractos Vegetales , Polifenoles/análisis

RESUMEN

The extract of Ginkgo biloba leaf is a popular herbal product or dietary supplement in the world to treat various diseases, and flavonol glycosides are considered as the main bioactive constituents. In this study, 37 flavonol glycosides were rapidly screened out by precursor ion scanning in positive ion mode with production ions at m/z 287.05, 303.05, and 317.06. Subsequently, a reliable and sensitive ultra-high-performance liquid chromatography coupled with triple quadrupole-linear ion trap mass spectrometry approach was established and validated to quantify the 20 prototype flavonol glycosides in rat plasma. Calibration curves showed good linearity (R2 ≥ 0.9894) over the corresponding concentration range. The precision, accuracy, extraction recovery, matrix effect, and stability were also satisfactory. The validated method was successfully applied to a pharmacokinetic study of prototype flavonol glycosides in rat after oral administration of the extract of G. biloba leaf. As a result, the Tmax of flavonol glycosides was short at 0.11-0.60 h. Quercetin-3-O-(2",6″-di-O-rhamnosyl)-glucoside, kaempferol-3-O-(2'',6''-di-O-rhamnosyl)-glucoside, quercetin-3-O-rutinoside, quercetin- 3-O-glucosyl-(1-2)-O-rhamnoside, and kaempferol-3-O-glucoside presented relatively high systemic exposure levels with AUC0-∞  > 500 µg h/L and Cmax  > 100 µg/L. This study would provide the valuable information for further scientific research and clinical application of the extract of G. biloba leaf.

Asunto(s)

Glicósidos , Espectrometría de Masas en Tándem , Animales , Cromatografía Líquida de Alta Presión/métodos , Flavonoides , Flavonoles , Ginkgo biloba/química , Glicósidos/análisis , Extractos Vegetales/química , Hojas de la Planta/química , Ratas , Espectrometría de Masas en Tándem/métodos

RESUMEN

Elderflowers are a well-known source of bioactive compounds. The amount of isolated bioactive compounds may be increased by applying various abiotic and biotic factors. Gaseous ozone (10 and 100 ppm) was used in the process of preparing flowers. Next, the flowers were treated with sugar syrup to extract bioactive compounds. It was shown that this treatment, including the influence of extraction temperature, significantly affects the contents of polyphenols (liquid chromatography-mass spectrometry (LC-MS) methods) and vitamin C, as well as the antioxidant potential (cupric reducing antioxidant capacity (CUPRAC method)), the profile of volatile substances (head space-solid-phase microextraction (HS-SPME methods)) and the colour of the syrup (Commission Internationale de l'Eclairage (CIE) L*a*b* methods). The findings show that an increased dose of ozone and higher extraction temperature applied in the process of syrup production resulted in higher contents and different compositions of bioactive compounds. The highest contents of bioactive compounds were identified in syrup obtained from raw material treated with ozone for 15 min (concentration = 10 ppm) and extraction with sugar syrup at a temperature of 60 °C.

Asunto(s)

Ozono , Fitoquímicos , Sambucus nigra , Antioxidantes , Flores

RESUMEN

Oxidative stress is usually associated with prolonged intake of high-fat diet (HFD). However, little is known about the impact of maternal HFD on endogenous modulation of antioxidant-defence-enzyme-network, its link to adverse fetal growth and overall effects of Quercetin-3-o-rutinoside (QR) supplementation. Sprague-Dawley rats were initially assigned to normal diet (ND) or HFD for 8 weeks and mated. Post-conception, rats were further divided into four groups, of which two groups had diets supplemented with QR while others continued with their respective diets until delivery. Measurements include food and water consumption, physical parameters (body weight, body mass index (BMI) and fur appearance), oral glucose tolerance, lipid profiles, and placental/liver oxidative changes. We observed that water consumption was significantly increased in dams fed HFD without marked differences in food intake, body weight, BMI and glucose tolerance. Surprisingly, offspring of HFD-fed dams had reduced body weight marked by delayed fur appearance compared to the ND offspring. In dams, there were alterations in lipid profile. Lipid peroxidation was increased in the placenta and liver of gestational day (GD) 19 HFD-fed dams and their postnatal day (PND) 21 male offspring. There was evidence of HFD-induced nitrosative stress in dams and PND28 female offspring. Adaptive defence indicate decreased placenta and liver superoxide dismutase (SOD) levels as well as differential changes in total antioxidant capacity (TAC) and catalase (CAT) activity in HFD treated dams and their progenies. Overall, the results indicate that intrauterine metabolic alterations associated with maternal high-fat consumption may induce oxidative challenge in the offspring accompanied by mild developmental consequences, while QR supplementation has little or no beneficial effects.

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Thalictrum minus L., which is widespread across Eurasia, is utilized as a folk medicine for treating dysentery, bedsore, fungal infection and lung inflammation in China, Mongolia and Iran. AIM OF THE STUDY: A Mongolian folk medicinal plant named Thalictrum minus L. (TML) has been extensively used for the treatment of lung inflammation, bacterial and fungal infection and tuberculosis. Our present study aims to investigate the effectiveness of TML against particulate matter (PM)-induced acute lung injury (ALI) and the potential underlying mechanisms. MATERIALS AND METHODS: Initially, HPLC-Q-TOF was applied for the qualitative analysis and HPLC was used for quantitative analysis of main components in TML. Then, the mice model of ALI was induced by PM via intratracheally instilled with 50 mg/kg body weight of Standard Reference Material1648a (SRM1648a), and TML (10, 20, 40 mg/kg) were administered orally 1 h prior to PM. The efficacy and molecular mechanisms in the presence or absence of TML were elucidated. RESULTS: Eleven main ingredients were detected in TML and the contents of homoorientin and berberine were quantified. Additionally, the results demonstrated that TML profoundly inhibited weight loss in mice and ameliorated lung pathological injury induced by PM. Furthermore, we also found that TML significantly decreased the lung wet to dry weight (W/D) ratios, reduced total protein in bronchoalveolar lavage fluid (BALF), and effectively attenuated PM-induced increased leukocyte and macrophages in BALF. Meanwhile, TML could pronouncedly inhibited myeloperoxidase (MPO) activity in lung tissues, decreased the PM-induced inflammatory cytokines including tumor necrosis factor-α (TNF-α), interleukin-6 (IL-6) and interleukin-1ß (IL-1ß), reduced nitric oxide (NO) and increased superoxide dismutase (SOD) in BALF. In addition, TML markedly facilitated the expression of p-AMPK-Nrf2 and suppressed the expression of KEAP, prohibited the activation of the MAPKs-NLRP3/caspase-1 and cyclooxygenase-2 (COX2), and inhibited apoptotic pathways. CONCLUSION: These findings indicated that TML attenuated PM-induced ALI through suppressing the release of inflammatory cytokines and alleviating oxidative damage correlated with the AMPK-Nrf2/KEAP signaling pathways, MAPKs-NLRP3/caspase-1 signaling pathways, as well as apoptotic pathways.

Asunto(s)

Lesión Pulmonar Aguda/inducido químicamente , Lesión Pulmonar Aguda/tratamiento farmacológico , Antiinflamatorios/uso terapéutico , Material Particulado/efectos adversos , Extractos Vegetales/uso terapéutico , Thalictrum , Lesión Pulmonar Aguda/metabolismo , Animales , Antiinflamatorios/aislamiento & purificación , Antiinflamatorios/farmacología , Relación Dosis-Respuesta a Droga , Mediadores de Inflamación/antagonistas & inhibidores , Mediadores de Inflamación/metabolismo , Masculino , Ratones , Ratones Endogámicos C57BL , Extractos Vegetales/aislamiento & purificación , Extractos Vegetales/farmacología

RESUMEN

Ziziphi Spinosae Folium, the leaf of Ziziphus jujuba Mill. Var. spinosa (Bunge) Hu ex H. F. Chou (LZJS), is currently used as a healthy tea in China. This study evaluated the chemical components and antioxidant activities of LZJS flavonoid (LZJSF) and fermented LZJSF (FLZJSF) using human intestinal bacteria (HIB) through dynamic fermentation. Eighteen flavonoids were simultaneously identified in LZJSF using UHPLC-Q-Orbitrap-MS method, nine of which were targeted for a HIB metabolism study. Seven small phenolic acids were identified in FLZJSF. Not only at chemical level but also at PC12 cell level, FLZJSF samples fermented for 4 and 6 h showed significant positive correlation between their activities and flavonoid aglycones, which were transformed from LZJSF. However, FLZJSF samples (8 h and longer time) mainly contained phenolic acids and indicated weak activities. Thus, LZJSF was found to result in increased antioxidant activity and could be commercially utilized as a novel functional food.

Asunto(s)

Antioxidantes/metabolismo , Bacterias/metabolismo , Alimentos Fermentados/microbiología , Flavonoides/análisis , Ziziphus/metabolismo , Adulto , Animales , Antioxidantes/análisis , Antioxidantes/farmacología , Cromatografía Líquida de Alta Presión/métodos , Femenino , Flavonoides/metabolismo , Microbioma Gastrointestinal , Humanos , Masculino , Células PC12 , Extractos Vegetales/análisis , Extractos Vegetales/metabolismo , Hojas de la Planta/química , Hojas de la Planta/metabolismo , Ratas , Ziziphus/química

RESUMEN

Apple is rich in flavonol glycosides, which are believed to contribute to putative health benefits associated with apple consumption. Glycosylation, catalyzed by uridine diphospho-glycosyltransferases (UGTs), is the last step in flavonol biosynthesis, which confers molecular stability and solubility to the flavonol. In the present study, the involvement of two UGTs, MdUGT75B1 and MdUGT71B1, in flavonol biosynthesis in apple was investigated. The major flavonols are quercetin 3-O-glycosides, and UV-B and blue light treatment significantly enhanced the accumulation of quercetin 3-O-galactoside, quercetin 3-O-glucoside, and kaempferol 3-O-galactoside. Transcript levels of MdUGT75B1 and MdUGT71B1 in fruit subjected to different treatments were correlated well with flavonol accumulation. MdUGT75B1 showed flavonol-specific activity with a preference for UDP-galactose as the sugar donor, while MdUGT71B1 using UDP-glucose exhibited a wider substrate acceptance. Thus, MdUGT75B1 and MdUGT71B1 are key UGTs involved in flavonol biosynthesis and may have important roles in regulating accumulation of these health-promoting bioactive compounds in apple.

Asunto(s)

Galactósidos/biosíntesis , Glucósidos/biosíntesis , Glicosiltransferasas/metabolismo , Quempferoles/biosíntesis , Malus/química , Quercetina/análogos & derivados , Frutas/química , Frutas/metabolismo , Malus/metabolismo , Quercetina/biosíntesis , Uridina/metabolismo

RESUMEN

ETHNOPHARMACOLOGICAL RELEVANCE: Ethnopharmacological surveys on Guinea-Bissauan flora reveal that several species are used to treat or ameliorate the symptomatology of conditions with an inflammatory background. As such, extracts obtained from a series of plants recorded in those surveys were screened for their anti-inflammatory properties, a hydroethanolic extract obtained from the leaves of Xylopia aethiopica (Dunal) A. Rich, (Annonaceae), used on the treatment of headache, muscular pain and rheumatic pain, scoring positively and being further investigated. AIM OF THE STUDY: In order to identify species with anti-inflammatory properties, extracts were screened for their ability to interfere with LPS-induced TNF-α levels. Since significant effects were recorded upon treatment with the extract of the leaves obtained from X. aethiopica, further assays were conducted to elucidate additional mechanisms underlying its anti-inflammatory potential. Since little is known on the chemical composition of the plant, we also aimed to characterise its phenolic profile. MATERIALS AND METHODS: Interference with cytokines was evaluated by ELISA assay, through the quantification of TNF-α and IL-6 levels in the culture medium collected from LPS-activated THP-1-derived-macrophages. Inhibition of 5-lipoxygenase was assessed based on the oxidation of linoleic acid to 13-hydroperoxylinoleic acid. Characterization of the phenolic profile was attained by HPLC-DAD. RESULTS: Evaluation of TNF-α levels in LPS-challenged THP-1 macrophages evidenced a significant inhibition (>90%) upon treatment with the hydroethanolic extract obtained from X. aethiopica leaves at a concentration of 500 µg/mL. Additional anti-inflammatory effects were recorded, including a significant decrease on IL-6 levels at 250 and 500 µg/mL. The extract proved to be active towards 5-LOX, leading to significant inhibition at concentrations ranging from 16 to 250 µg/mL (IC50 = 85 µg/mL). Phenolic profiling allowed the identification and quantitation of eight constituents, including caffeoylquinic acids (1-3), mono-O-glycosylated flavonols (5-8), and the mono-O-glycosyl flavone luteolin-7-O-glucoside (4). The main phenolic constituent, kaempferol-3-O-rutinoside (8), was found to significantly contribute to the anti-inflammatory effects, namely through the inhibition of 5-LOX. However, no effects on the decrease of TNF-α and IL-6 levels caused by this phenolic compound were found. CONCLUSION: The anti-inflammatory effects of X. aethiopica leaves are demonstrated experimentally, thus substantiating its use in folk Medicine. Relevantly, the observed anti-inflammatory properties can stimulate further studies in order to fully unveil the therapeutic potential of the plant, namely as a source of phenolic compounds with a significant ability to interfere with conventional inflammatory targets.

Asunto(s)

Antiinflamatorios/farmacología , Flavonoides/farmacología , Mediadores de Inflamación/metabolismo , Interleucina-6/metabolismo , Macrófagos/efectos de los fármacos , Extractos Vegetales/farmacología , Hojas de la Planta , Factor de Necrosis Tumoral alfa/metabolismo , Xylopia , Antiinflamatorios/aislamiento & purificación , Araquidonato 5-Lipooxigenasa/metabolismo , Flavonoides/aislamiento & purificación , Humanos , Lipopolisacáridos/toxicidad , Macrófagos/metabolismo , Extractos Vegetales/aislamiento & purificación , Hojas de la Planta/química , Células THP-1 , Xylopia/química

RESUMEN

Jabuticaba is a Brazilian berry rich in phenolic compounds (PC), which are mainly concentrated in its peel and seed (JPS), fractions that are not usually consumed. Thus, to develop a powder with potential functional properties, we investigated the effect of pressurization and dehydration methods on the chemical composition of JPS, with emphasis on PC. JPS showed a very diverse PC profile, including phenolic acids, flavonoids, ellagitannins and proanthocyanidins. Contrary to our hypothesis, pressurization was ineffective in increasing total PC contents of JPS. Freeze-drying and oven-drying at 75 °C yielded powders with similar total PC contents, but with distinct profile, the former richer in anthocyanins and the latter in ellagitannins. Considering that both dehydration methods produced a jabuticaba powder rich in PC, and that freeze-drying is a higher cost method, the choice between these drying methods depends on the purpose of the final product.

Asunto(s)

Cromatografía Líquida de Alta Presión , Espectrometría de Masas , Myrtaceae/química , Fenoles/química , Antocianinas/química , Antioxidantes/química , Liofilización , Frutas/química , Frutas/metabolismo , Taninos Hidrolizables/química , Presión Hidrostática , Myrtaceae/metabolismo , Fenoles/análisis , Extractos Vegetales/química , Semillas/química , Semillas/metabolismo

RESUMEN

Objective: To establish a method for determination of quercetin-3-O-gentiobioside, quercetin-3-O-rutinoside, isoquercitrin, quercetin, and 5,7,4'-trihydroxyflavone in Abelmoschus esculentus from 12 different regions of China. Methods: COSMOSIL column (250 mm × 4.6 mm, 5.4 μm) was used. The gradient elution was carried out with acetonitrile and 0.2% phosphoric acid aqueous solution. The detection wavelength was 353 nm and the flow rate was 1 mL/min. Results: The contents of quercetin-3-O-gentiobioside, quercetin-3-O-rutinoside, isoquercitrin, quercetin and 5,7,4'-trihydroxyflavone had good linear relationship in the ranges of 15.72- 251.50 μg/mL (r = 0.999 5), 15.47-247.50 μg/mL (r = 0.999 6), 14.41-230.50 μg/mL (r = 0.999 5), 21.88-350.00 μg/mL (r = 0.999 7), and 17.25-276.00 μg/mL (r = 0.999 1). The average sample recovery rate was 97.46%, 96.74%, 100.21%, 95.66%, 98.35%, and RSD was 1.97%, 1.37%, 1.86%, 2.72%, 2.23%, respectively. Conclusion: This method is simple and accurate. It is suitable for simultaneous determination of quercetin-3-O-gentiobioside, quercetin-3-O-rutinoside, isoquercitrin, quercetin and 5,7,4'-trihydroxyflavone. The content of the five flavones can be used as one of the methods for evaluating the quality of A. esculentus.

RESUMEN

Syrah must was co-inoculated with mixed cultures of Saccharomyces + O. oeni/Lb. plantarum and Saccharomyces + non-Saccharomyces + O. oeni/Lb. plantarum to evaluate the effect on phenolics and sensory attributes. Reference wines were produced by S. cerevisiae. Malvidin-3-O-glucoside, flavan-3-ols, flavonols and phenolic acids were quantified using a RP-HPLC technique. Physicochemical characteristics and sensory attributes were measured. Total acidity and alcohol in mixed co-inoculations were different from reference wines. The concentration of l-malic acid was 7-times less in mixed co-inoculations. Mixed co-inoculations had ca. 1.3-times more malvidin-3-O-glucoside and phenolic acids than reference wines. Flavan-3-ols and flavonols were not different between mixed co-inoculations and reference wines. Acidity and astringency were least in mixed co-inoculations. Mouthfeel and bitterness least in S. cerevisiae wines. Tasters preferred mixed co-inoculated wines. Mixed co-inoculation is a strategy to contemplate for Syrah vinification but the modalities of inoculation need further investigation. Success depends on a suitable combination of yeast/bacteria and consideration of strain variation.

RESUMEN

The berries from the native Chilean Gaultheria phillyreifolia and G. poeppigii are appreciated for their sweet taste and aroma. Fruits from both species were investigated for their secondary metabolite composition and antioxidant activity. The extracts were submitted to membrane chromatography to separate anthocyanins from copigments. Four anthocyanins were isolated by counter-current chromatography (CCC) and identified as cyanidin galactoside, cyanidin arabinoside, delphinidin galactoside and delphinidin arabinoside. From the copigments, CCC allowed the separation of quercetin(Q)-3-arabinoside, Q-3-rutinoside Q-3-rhamnoside and 3-caffeoylquinic acid. Additionally, the iridoids monotropein-10-trans-coumarate, monotropein-10-trans-cinnamate and 6α-hydroxy-dihydromonotropein-10-trans-cinnamate were isolated. The latter two iridoids are reported here for the first time. Some 34 other compounds were tentatively identified by HPLC-DAD-ESI-MSn. The antioxidant activity showed differences between anthocyanins and copigments from both species. Main compounds were quantified and submitted to a Partial-Least Square Discriminant Analysis (PLS-DA). This is the first report on the isolation of phytochemicals from the selected Chilean Gaultheria species.

Asunto(s)

Antioxidantes/química , Gaultheria/química , Iridoides/química , Polifenoles/química , Chile , Cromatografía Líquida de Alta Presión , Distribución en Contracorriente , Análisis Discriminante , Frutas/química , Frutas/metabolismo , Gaultheria/metabolismo , Iridoides/aislamiento & purificación , Análisis de los Mínimos Cuadrados , Extractos Vegetales/química , Polifenoles/aislamiento & purificación , Espectrometría de Masa por Ionización de Electrospray

RESUMEN

Phenolic compounds are a large class of plant secondary metabolites with various health-promoting effects, and are known for their structural diversity. Therefore, high efficiency characterization of phenolic profiles is of key importance in identifying their potential bioactivity. In the present study, Global Natural Products Social (GNPS) Molecular Networking was applied to trace the phenolic compounds in plants, which allowed the characterization of 9 procyanidins and 11 flavonoid glycosides (di-, tri-, or tetra-saccharides of kaempferol, quercetin, isorhamnetin and myricetin) in litchi pulp extracts. Six compounds were reported for the first time in litchi pulp. In addition, quercetin-3-O-rutinoside-(1 → 2)-O-rhamnoside, the most abundant flavonoid glycoside in litchi pulp, was proved to have considerable α-glucosidase inhibitory activity, illustrating the anti-diabetic potential of phenolic-rich litchi pulp extracts.

Asunto(s)

Litchi/química , Fenoles/análisis , Espectrometría de Masas en Tándem , Cromatografía Líquida de Alta Presión , Frutas/química , Frutas/metabolismo , Glicósidos/análisis , Litchi/metabolismo , Espectroscopía de Resonancia Magnética , Extractos Vegetales/química , Proantocianidinas/análisis

RESUMEN

Assembling between polyphenols and proteins has been freshly spotlighted. We studied the antiglycation and anti-hardening effects of microencapsulated mulberry polyphenols (MMPs) in a high-protein-sugar ball (HPSB) model during storage using multi-dimensional approaches, including UPLC-ESI-MS/MS, SDS-PAGE, MALDI-TOF-MS, FTIR, and a molecular docking study. It was found that MMPs significantly relegated the browning development, AGEs, and/or CML levels of HPSB after 45 d of storage at 45 °C. MMPs also downgraded the protein insolubility, aggregation, oligomerization, and glycoxidation during late-storage. A molecular docking scrutiny proved that cyanidin 3-O-rutinoside and quercetin 3-O-rutinoside interacted with whey proteins subunits via H-bonding and π-π interactions. This binding blocked some glycation residues of whey proteins especially lysyl residues, namely Lys5, 16, 60, 69, 93, 94, and 122. Our data disclosed that MMPs could be valorized as promising antiglycative ingredients to mitigate AGEs-generation and other subsequent unwanted changes in protein-rich food matrices.

Asunto(s)

Glicosilación/efectos de los fármacos , Dureza/efectos de los fármacos , Morus/química , Polifenoles/farmacología , Azúcares/metabolismo , Proteína de Suero de Leche/metabolismo , Antocianinas/farmacología , Frutas/química , Glucósidos/farmacología , Simulación del Acoplamiento Molecular/métodos , Extractos Vegetales/farmacología , Quercetina/análogos & derivados , Quercetina/farmacología , Espectrometría de Masas en Tándem/métodos

RESUMEN

The hypocholesterolemic effect of Lonicera caerulea berry extract rich in polyphenols (LCBP) on high cholesterol-induced hypercholesterolemia and lipoprotein metabolite changes was examined in Caco-2 cells and rats. Cyanidin-3-glucoside, catechin, and chlorogenic acid are the major phenolic components of LCBP. The cholesterol-reducing effect and antioxidant capacity of these components were compared in Caco-2 cells. LCBP (80 µg/mL) and cyanidin-3-glucoside, catechin, and chlorogenic acid (50 µM) were found to be effective (p < 0.05). Rats were fed a high cholesterol diet (HCD) with or without LCBP supplementation (75, 150, and 300 mg/kg body weight intragastrically once daily) for 12 weeks. Compared with the HCD control group, LCBP supplementation at 150 and 300 mg/kg decreased the levels of TC, TG, and LDL-C, but increased that of HDL-C. LCBP treatment promoted greater neutral and acidic sterol excretion (p < 0.05) and improved the antioxidant capacity of the colon tissue, colon contents, and blood. Moreover, trimethylamine N-oxide (TMAO) levels were decreased in serum (p < 0.05). NPC1L1, ACAT2, and MTP mRNA and protein expression were reduced and ABCG5/8 expression was increased (p < 0.05) after LCBP treatment. Our results suggest that LCBP could be used as a functional food for the prevention and treatment of diseases related to excessive cholesterol accumulation.

Asunto(s)

Anticolesterolemiantes/farmacología , Antioxidantes/farmacología , Colesterol/sangre , Frutas , Hipercolesterolemia/prevención & control , Lonicera , Estrés Oxidativo/efectos de los fármacos , Extractos Vegetales/farmacología , Polifenoles/farmacología , Animales , Anticolesterolemiantes/aislamiento & purificación , Antioxidantes/aislamiento & purificación , Biomarcadores/sangre , Células CACO-2 , Modelos Animales de Enfermedad , Heces/química , Frutas/química , Humanos , Hipercolesterolemia/sangre , Absorción Intestinal/efectos de los fármacos , Mucosa Intestinal/efectos de los fármacos , Mucosa Intestinal/metabolismo , Lipoproteínas/sangre , Lonicera/química , Masculino , Extractos Vegetales/aislamiento & purificación , Polifenoles/aislamiento & purificación , Ratas Sprague-Dawley , Triglicéridos/sangre

RESUMEN

The transglycosylation activity of amylosucrase (ASase) has received significant attention owing to its use of an inexpensive donor, sucrose, and broad acceptor specificity, including glycone and aglycone compounds. The transglycosylation reaction of recombinant ASase from Deinococcus radiopugnans (DRpAS) was investigated using various phenolic compounds, and quercetin-3-O-rutinoside (rutin) was found to be the most suitable acceptor molecule used by DRpAS. Two amino acid residues in DRpAS variants (DRpAS Q299K and DRpAS Q299R), assumed to be involved in acceptor binding, were constructed by site-directed mutagenesis. Intriguingly, DRpAS Q299K and DRpAS Q299R produced 10-fold and 4-fold higher levels of rutin transglycosylation product than did the wild-type (WT) DRpAS, respectively. According to in silico molecular docking analysis, the lysine residue at position 299 in the mutants enables rutin to more easily position inside the active pocket of the mutant enzyme than in that of the WT, due to conformational changes in loop 4.

Asunto(s)

Proteínas Bacterianas/química , Proteínas Bacterianas/metabolismo , Deinococcus/enzimología , Glucosiltransferasas/química , Glucosiltransferasas/metabolismo , Rutina/metabolismo , Secuencias de Aminoácidos , Proteínas Bacterianas/genética , Sitios de Unión , Deinococcus/química , Deinococcus/genética , Glucosiltransferasas/genética , Glicosilación , Cinética , Simulación del Acoplamiento Molecular , Rutina/química , Especificidad por Sustrato

RESUMEN

This study optimizes the application of portable Near Infrared-Acousto Optically Tunable Filter (NIR) device to meet the increasing demand for cost-effective, non-invasive and easy-to-use methods for measuring physical and chemical properties during olive fruit development. Fruits from different phenotypically cultivars were sampled for firmness, total and specific phenols detection by HPLC, total anthocyanins, chlorophyll and carotenoids detection by spectrophotometry. On the same fruits, a portable NIR device in diffuse reflectance mode was employed for spectral detections. Predictive models for firmness, chlorophyll, anthocyanins, carotenoids and rutin were developed by Partial Least Square analysis. Oleuropein, verbascoside, 3,4-DHPEA-EDA, and total phenols were used to develop a validation model. Internal cross-validation was applied for calibration and predictive models. The standard errors for calibration, cross-validation, prediction, and RPD ratios (SD/SECV) were calculated as references for the model effectiveness. The determination of the optimal harvesting time facilitates the production of high quality extra virgin olive oil and table olives.

Asunto(s)

Olea/química , Aceite de Oliva/normas , Calibración , Frutas/química , Análisis de los Mínimos Cuadrados , Mutación , Fenoles/análisis , Espectroscopía Infrarroja Corta