Antioxidant and α-glucosidase inhibitory activities of eight neglected fruit extracts and UHPLC-MS/MS profile of the active extracts

The 70% ethanolic extracts from eight neglected fruits; Muntingia calabura, Leucaena leucocephala, Spondias dulcis, Syzygium jambos, Mangifera caesia, Ardisia elliptica, Cynometra cauliflora and Ficus auriculata were evaluated for their 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging, α-glucosidase inhibitory activities as well as total phenolic content. The results of this study revealed that M. caesia fruit extract demonstrated the most potent radical scavenging activity. Among the fruits examined for α-glucosidase inhibitory activity, M. calabura and F. auriculata exhibited strong activity with no significant difference. The Pearson correlation indicated that the activities of M. caesia and F. auriculata contributed by phenolic compounds. A total of 65 metabolites were tentatively identified by using ultra-high-performance liquid chromatography tandem mass spectrometry (UHLPC-MS/MS). These findings suggested that the possible application of M. caesia and F. auriculata as a functional food with antioxidant and α-glucosidase inhibitory properties.     

LC–MS/MS characterization,antidiabetic, antioxidative,and antibacterial effects of different solvent extracts of Anamur banana (Musa Cavendishii)

Food Science and Biotechnology - The main objective of this study was to examine the phenolic compounds and the antibacterial, antioxidant, anti-α-glucosidase and anti-α-amylase...     

Characterization of gluten-free rice bread prepared using a combination of potato tuber and ramie leaf enzymes

A combination of freeze-dried powder of disproportionating enzyme (D-enzyme)-containing potato tuber and β-amylase-containing ramie leaf was used to improve the gluten-free (GF) bread, and its physicochemical properties were characterized. The presence of D-enzyme and β amylase in the potato tuber and ramie leaf was confirmed. Sixty five percent of partially gelatinized rice flour and 20% corn starch was combined with 10% freeze-dried potato tuber and 1% ramie leaf powder, and baked. The specific volume increased by 23% compared to the control with improved internal characteristics. Texture profile analysis revealed that retrogradation of the bread was retarded when stored for 90 h at 4 °C. The bread crumb amylose content was reduced from 14 to 9% and amylopectin branch chain-length distribution was rearranged, whereby the proportions of the branch chains with Degree of polymerization (DP) < 9 and DP > 19 decreased. The results suggest that D-enzyme and β-amylase cooperatively altered amylose/amylopectin ratio and amylopectin structure.     

Thermal decomposition and oxidation of β-caryophyllene in black pepper during subcritical water extraction

Subcritical water extraction is an efficient technique for extracting components from various plants by changing the polarity of water. β-caryophyllene is a natural bicyclic sesquiterpene with the highest content found among black pepper essential oils. In this study, the efficiency of extraction and yield of β-caryophyllene from black pepper were investigated using a subcritical water extraction technique. The optimal conditions of β-caryophyllene (1.19 ± 0.38 mg/g), and caryophyllene oxide (0.82 ± 0.38 mg/g) were obtained from black pepper under extraction conditions of 170 °C/10 min, and 200 °C/15 min, respectively. As the extraction temperature was increased, β-caryophyllene oxidation proceeded and the extraction content of caryophyllene oxide increased. It is anticipated that both β-caryophyllene and caryophyllene oxide with high biological activity can be used to selectively extract compounds using subcritical water extraction, which will be helpful in industrial applications.     

Recovery of hesperidin and narirutin from waste Citrus unshiu peel using subcritical water extraction aided by pulsed electric field treatment

The objective of this study was to identify whether the efficacy of extracting hesperidin and narirutin from Citrus unshiu peel by-products can be increased by combining pulsed electric field (PEF) and subcritical water extraction (SWE). The samples were treated with a PEF at a strength of 3 kV/cm for 60 and 120 s. Subsequent SWE was conducted at extraction temperatures of 110–190 °C for 3–15 min. The concentration of hesperidin was highest at 46.96 ± 3.37 mg/g peel (dry basis) after PEF treatment at 120 s, combined with SWE at 150 °C for 15 min, while that of narirutin peaked at 8.76 ± 0.83 mg/g after PEF treatment at 120 s, integrated with SWE at 190 °C for 5 min. The concentrations of both hesperidin and narirutin increased with PEF treatment time. The PEF increased the amounts of hesperidin and narirutin extracted by 22.1% and 33.6%, respectively. This study demonstrate the potential of PEF pretreatment for enhancing the SWE of flavonoids from C. unshiu peel.     

A Novel α-Glucosidase of the Glycoside Hydrolase Family 31 from Aspergillus sojae

We characterized an α-glucosidase belonging to the glycoside hydrolase family 31 from Aspergillus sojae. The α-glucosidase gene was cloned using the whole genome sequence of A. sojae, and the recombinant enzyme was expressed in Aspergillus nidulans. The enzyme was purified using affinity chromatography. The enzyme showed an optimum pH of 5.5 and was stable between pH 6.0 and 10.0. The optimum temperature was approximately 55 °C. The enzyme was stable up to 50 °C, but lost its activity at 70 °C. The enzyme acted on a broad range of maltooligosaccharides and isomaltooligosaccharides, soluble starch, and dextran, and released glucose from these substrates. When maltose was used as substrate, the enzyme catalyzed transglucosylation to produce oligosaccharides consisting of α-1,6-glucosidic linkages as the major products. The transglucosylation pattern with maltopentaose was also analyzed, indicating that the enzyme mainly produced oligosaccharides with molecular weights higher than that of maltopentaose and containing continuous α-1,6-glucosidic linkages. These results demonstrate that the enzyme is a novel α-glucosidase that acts on both maltooligosaccharides and isomaltooligosaccharides, and efficiently produces oligosaccharides containing continuous α-1,6-glucosidic linkages.     

Effect of thermal processing on phenolics, antioxidant activity and health-relevant functionality of select grain sprouts and seedlings

The effect of thermal processing via autoclaving on modifications of total phenolics, antioxidant activity and functionality of wheat, buckwheat, corn and oats sprouts and seedlings were investigated. Functionality for type 2 diabetes related α-amylase, α-glucosidase inhibition and levo-dihydroxy phenylalanine (l-DOPA) content, hypertension related angiotensin converting enzyme 1 (ACE) inhibition and ulcer related Helicobacter pylori inhibition were evaluated using in vitro assays. Thermal processing in general resulted in tissue browning leading to higher total phenolic content and free radical scavenging-linked antioxidant activity. It increased α-amylase inhibitory activity in buckwheat and oats but decreased in wheat and corn sprouts and seedlings. It increased α-glucosidase inhibitory activity in wheat, buckwheat and oats but decreased in corn sprouts. It reduced the cognitive function/diabetes related l-DOPA content in all grains sprouts and seedlings tested. It increased ACE inhibitory activity in buckwheat and oats, but decreased in wheat and corn sprouts. It also improved the ulcer related H. pylori inhibitory activity in all grain sprouts and seedlings studied. These changes in functionality are suggested to be due to modifications in the total phenolic content and profile by phenolic oxidation or polymerization caused by thermal processing. Therefore, diet designs for chronic disease management will have to consider thermal processing-linked modification of bioactive ingredient profiles.

Industrial relevance

Thermal processing altered the total phenolic content and antioxidant activity in winter wheat, buckwheat, corn and oats sprouts and seedlings. It modified the α-amylase inhibitory activity, α-glucosidase inhibitory activity, l-DOPA content, ACE inhibitory activity and H. pylori inhibitory activity of samples. Therefore, the food processing industry and diet design for chronic disease management will have to consider thermal processing-linked modification of bioactive ingredient profiles for more effective health benefits.     

Chemical composition and bioactivities of the polyphenolic-rich extract of Ormenis africana Jord. and Fourr

Ormenis africana is an endemic North African species used in folk medicine because of its hypoglycemic property. In this study, the α-amylase and α-glucosidase inhibition and antioxidant activities of the polyphenolic-rich extract from O. africana were determined. The chemical composition was made using liquid chromatography with photodiode array and electrospray ionization mass spectrometry method and the identification of phenolics was assessed by comparing their retention times and ultraviolet and mass spectra with those of the standards and/or reported in the literature. The total phenolic content was estimated by the Folin–Ciocalteu method. The antidiabetic potential was estimated by the determination of α-amylase and α-glucosidase inhibition in vitro. Four assays were used for the evaluation of antioxidant activity of the extracts. Seventeen phenolic compounds were detected. The major peaks are chlorogenic acid, 5-O-di-caffeoylquinic acid, and apigenin and luteolin derivatives. The polyphenolic-rich extract showed remarkable α-amylase and α-glucosidase inhibition activity in a concentration dependent manner. Furthermore, the extract also demonstrated high antioxidant activities. O. africana can serve as a potential natural source for the development of a novel α-amylase and α-glucosidase inhibitory agents against diabetic complications.     

Antioxidant Capacities,Phenolic Contents,and GC/MS Analysis of Rhodiola imbricata Edgew. Root Extracts from Trans‐Himalaya

Our aim was to assess the antioxidant capacities and phenolic constituents of methanol and aqueous extracts of Rhodiola imbricata Edgew. root from Trans‐Himalayan cold desert of Ladakh. The 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) and 2,2′‐azinobis‐(3‐ethylbenzothiazoline‐6‐sulfonic acid (ABTS) radical scavenging capacity of the root extracts increased in a dose‐dependent manner (up to 0.1 mg/mL) and root extract concentrations required for 50% inhibition of radical scavenging effect (IC₅₀) were recorded as 0.013 and 0.014 mg/mL (for DPPH) and 0.016 and 0.017 mg/mL (for ABTS) for methanol and aqueous extracts, respectively. The total antioxidant power of the extract was determined by ferric reducing antioxidant power (FRAP) assay. Total polyphenol and phenolic acid content of methanol and aqueous extracts were 112.24, 59.06, 39.02, and 16.95 mg gallic acid equivalent/g of extract, respectively. Total flavonoid and flavonol contents were estimated to be 30.2, 17.67, 20.68, and 7.38 mg quercetin equivalent/g of extract, respectively. In all antioxidant capacity assays, the methanol extract exhibited significantly higher antioxidant capacity than that of aqueous extract due to the presence of significantly higher amount of vital phytoconstitiuents, viz. polyphenol, phenolic acid, and flavonol. GC/MS analysis showed that phytosterols, alkyl halide, phenols, and fatty acid esters were major phytochemical clusters. On the other hand, monoterpenes, fatty acids, tocopherols, aliphatic hydrocarbons, and ethers were found to be present in comparatively less amount in the methanol extract. Hence, our study signifies that this high‐altitude medicinal herb could be used as the natural source of antioxidants and supports its use in traditional system of medicine to ameliorate oxidative stress and high‐altitude maladies.     

Analysis of physiochemical composition and antioxidant properties between hulls of the genetically modified glyphosate-tolerant soybean and northeast soybean

In this study, the physiochemical and antioxidant properties of the soybean hulls from the genetically modified glyphosate-tolerant soybeans (line 40-3-2) and local cultivar northeast soybeans were investigated. The levels of fat, total phenolic, total extractable pectin and soluble dietary fiber in northeast soybeans hulls were less than that in glyphosate-tolerant soybeans hulls, respectively. The antioxidant capacity of total phenolic, water soluble pectin, and soluble dietary fiber showed that DPPH free radical scavenging activities of glyphosate-tolerant soybeans hulls were 118.23, 57.34 and 197.22 μg AAE/g, which were 2.3, 1.2 and 9.4 times of northeast soybeans hulls, respectively (p < 0.05), and FRAP of glyphosate-tolerant soybeans hulls were 401.67, 747.51 and 328.53 μg AAE/g, which were 1.8, 8.7 and 4.8 times of northeast soybeans hulls (p < 0.05). Glyphosate-tolerant soybeans hulls extract showed the stronger antioxidant activity, which was positively correlated with total phenolic content (r = 0.890, p = 0.001). It provides evidence on developing value-added utilization of hulls, soybean processing by-products, as nutraceuticals or functional food ingredients.     

Analysis of Transglucosylation Products of Aspergillus niger α-Glucosidase that Catalyzes the Formation of α-1,2- and α-1,3-Linked Oligosaccharides

According to whole-genome sequencing, Aspergillus niger produces multiple enzymes of glycoside hydrolases (GH) 31. Here we focus on a GH31 α-glucosidase, AgdB, from A. niger . AgdB has also previously been reported as being expressed in the yeast species, Pichia pastoris ; while the recombinant enzyme (rAgdB) has been shown to catalyze tranglycosylation via a complex mechanism. We constructed an expression system for A. niger AgdB using Aspergillus nidulans . To better elucidate the complicated mechanism employed by AgdB for transglucosylation, we also established a method to quantify glucosidic linkages in the transglucosylation products using 2D NMR spectroscopy. Results from the enzyme activity analysis indicated that the optimum temperature was 65 °C and optimum pH range was 6.0–7.0. Further, the NMR results showed that when maltose or maltopentaose served as the substrate, α-1,2-, α-1,3-, and small amount of α-1,1-β-linked oligosaccharides are present throughout the transglucosylation products of AgdB. These results suggest that AgdB is an α-glucosidase that serves as a transglucosylase capable of effectively producing oligosaccharides with α-1,2-, α-1,3-glucosidic linkages.     

红薯叶不同溶剂提取物抗氧化性及活性成分鉴定

研究不同极性溶剂对红薯叶中酚类化合物的提取以及提取物抗氧化性的影响,并鉴定提取物中的主要抗氧化成分组成。分别采用极性不同的7 种溶剂（蒸馏水、甲醇、无水乙醇、丙酮、正丁醇、乙酸乙酯和氯仿）从红薯叶中提取多酚,并评价提取物中总酚、总黄酮和花青素的含量,以及对1,1-二苯基-2-三硝基苯肼（1,1-diphenyl-2-picrylhydrazyl,DPPH）自由基清除能力和还原能力,最后运用高效液相色谱-串联质谱（high performance liquidchromatography tandem mass spectroscopy,HPLC-MS/MS）技术分析抗氧化活性最好的提取物中多酚的主要组成成分。结果表明：提取溶剂的极性对红薯叶中多酚类化合物的提取效率和提取物抗氧化活性有很大的影响,水提物具有最高的粗提物得率（（37.13±1.60）%）,而甲醇提取物中总酚含量（13.80 mg GAE/g）和总黄酮含量（（5.68±0.35）mg QE/g）最高,且具有最好的DPPH自由基清除能力（IC50为0.32 mg/mL）与还原能力（ρ0.5为0.95 mg/mL）。采用HPLC-MS/MS从红薯叶甲醇提取物中鉴定9 种、初步鉴定3 种酚类化合物,鉴定的化合物为咖啡酸、对羟基苯甲酸、1-咖啡酸奎宁酸、3-咖啡酸奎宁酸、异绿原酸A、异绿原酸B、异绿原酸C、3,4,5-三咖啡酰奎尼酸和金丝桃苷。     

Chemical profiling of Punica granatum peels from Jordan using LC–MS/MS and study on their biological activities

A paucity of local information concerning the chemical profiles and biological activities of extracts obtained from less-studied P. granatum peel of Jordanian origin was considered in this study for the first time. Fractionation of the crude ethanol extracts was performed because of their higher phenolic and flavonoid contents compared to the water and acetone extracts. The chemical compositions of the respective samples, that is, extracts/fractions were identified by LC–MS/MS, and the elemental content of the raw materials was also analysed using atomic absorption spectrometry. Antioxidant activities of extracts and fractions were evaluated against DPPH and ABTS radical scavenging assays, and the antibacterial activities were investigated by disc diffusion method and MIC (Minimum Inhibitory Concentration). The LC–MS/MS results correlated strongly with the total phenolic and flavonoid contents, where ethanol displayed higher efficacy for extracting bioactive ingredients. Overall, a total of 19 phenolics were detected in the ethanolic peel extract of P. granatum. All of the analysed extracts showed strong antioxidant activities. Fractionation of ethanolic extracts resulted in fractions with almost similar chemical LC–MS/MS profiles, but the relative proportion of constituents was different. All fractions showed lower intensities of antioxidant capacities than crude extracts, highlighting the superiority of some components, either individually or combined, as well as their relative proportion on the biological activity of each fraction. The results of the present study emphasise the need to further explore the effect of putative interactions among plant bioactive ingredients and focus on possible interactions with drugs along with foods.     

Evaluation of solvent effects on the DPPH reactivity for determining the antioxidant activity in oil matrix

Reactivity of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in methanol, ethanol, isopropanol, isooctane, and ethyl acetate, was evaluated to assess the antioxidant capabilities in medium chain triacylglycerol. DPPH loss values were obtained over 30 min, with sampling every 5 min. Even the same concentration of antioxidants showed different DPPH reactivity depending on solvent. In methanol, 5 min was enough for α-tocopherol to react with DPPH, whereas BHT did not react with DPPH even after 30 min. Gallate series showed higher DPPH reactivity than TBHQ, sesamol, or BHA in methanol, while lower reactivity in isooctane. Antioxidants in ethanol and isopropanol reacted with DPPH less efficiently compared to those in methanol, the exception being sesamol. DPPH reactivity of gallate series in isooctane was lower than that of sesamol, TBHQ, and α-tocopherol. Combinatorial usage of methanol and isooctane for DPPH reactivity could provide reliable information on the antioxidant capacities of chemicals in edible oils.Supplementary InformationThe online version contains supplementary material available at 10.1007/s10068-020-00874-9.     

Brewing of glucuronic acid-enriched apple cider with enhanced antioxidant activities through the co-fermentation of yeast (Saccharomyces cerevisiae and Pichia kudriavzevii) and bacteria (Lactobacillus plantarum)

Co-fermentation using yeast (Saccharomyces cerevisiae and Pichia kudriavzevii) and the bacteria (Lactobacillus plantarum) as starters isolated from spontaneous sourdough was conducted for the brewing of glucuronic acid (GlcA)-enriched apple cider. The concentration of GlcA in the apple cider co-fermented for 14 d with commercial S. cerevisiae and L. plantarum was 37.7 ± 1.7 mg/mL while a concentration of 62.8 ± 3.1 mg/mL was recorded for fermentation with P. kudriavzevii and L. plantarum, which was higher than the corresponding single yeast fermentation. The co-fermented apple cider revealed higher 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity of 171.67 ± 0.79 µg trolox equivalents (TE)/mL using P. kudriavzevii and L. plantarum, compared to the control (143.89 ± 7.07 µg TE/mL) just using S. cerevisiae. Thus, the co-fermentation of S. cerevisiae and L. plantarum and P. kudriavzevii and L. plantarum provided a new strategy for the development of GlcA-enriched apple cider with enhanced antioxidant capacity.     

Biological activity of rice extract and the inhibition potential of rice extract,rice volatile compounds and their combination against α-glucosidase, α-amylase and tyrosinase

Rice is produced for consumption and traditional medicine. Rice is also used as an ingredient in cosmetic products. In this study, the author investigated the biological activity and inhibition potential against α-glucosidase, α-amylase and tyrosinase activity of rice extract (black rice [BR], red rice [RR] and white rice [WR]), rice volatile compounds, rice extract combined with volatile compounds, rice extract combined with standard inhibitors and volatile compounds combined with standard inhibitors. The results revealed that the free-radical scavenging capacity of rice extract is related to the phenolic content and flavonoids. BR showed the highest potential to inhibit α-glucosidase and α-amylase activity, whereas WR showed the highest potential to inhibit tyrosinase activity. Among rice volatile compounds, vanillin and vanillyl alcohol had the highest inhibition potential against α-glucosidase and α-amylase, respectively, whereas guaiacol had the highest inhibitory activity against tyrosinase. Molecular docking supported by the high binding efficiency was also obtained from vanillin and guaiacol when located at the active site of these enzymes. The combination of RR with acarbose (AB) had the highest inhibition potential and showed a synergic effect on both α-glucosidase and α-amylase. Interestingly, the combination of rice extract (BR, RR and WR) and vanillin and vanillyl alcohol had a synergic effect on α-amylase. Moreover, the combination of WR and vanillyl alcohol had the highest inhibition potential and showed a synergic effect on tyrosinase, whereas rice volatile compounds had a synergic effect on tyrosinase obtained from 2-pentylfuran/kojic acid (KA), vanillin/KA and vanillyl alcohol/KA.     

Profiling of phenolic compounds using UPLC–Q-TOF-MS/MS and nephroprotective activity of Indian green leafy vegetable Merremia emarginata (Burm. f.)

The present study aimed at optimization and identification of phenolic compounds from Merremia emarginata (Burm. f.) through RP-HPLC and UPLC–MS/MS. Further, to investigate nephroprotective effect of M. emarginata against gentamicin induced nephrotoxicity in albino Wistar rats phenolic compound identification was carried out using UPLC–MS/MS in both positive and negative modes of ionization. There are about 29 known and 19 unknown phenolic compounds that have been detected in M. emarginata based on MS/MS fragmentation pattern. The nephrotoxicity was induced by gentamicin in albino Wistar rats through i.p. injection (20 mg/kg of b.wt) and the rats were treated orally with ethanol extract of M. emarginata (150, 200 and 250 mg/kg of b.wt) for fifteen days. Serum biochemical parameters were analyzed and histopathological study was carried out to evaluate nephroprotective activity. The histopathology study shows that compared to the control group, the kidney of the diseased group was highly damaged and the plant extract treated group shows regeneration of glomerular and tubular epithelial cells of damaged kidney.     

老山芹降血糖功能成分提取及活性研究

为增加老山芹资源的开发利用价值,以老山芹为原料,采用不同溶剂(不同浓度乙醇溶液、甲醇、乙酸乙酯)超声波辅助提取老山芹活性成分,以α-葡萄糖苷酶抑制率和α-淀粉酶抑制率为指标,确定适宜的提取溶剂,并通过单因素和响应面优化试验确定可保留老山芹降血糖功能成分的最佳提取条件。结果表明:适宜的提取溶剂为80%乙醇溶液,优化后的提取条件为超声温度49 ℃,超声时间114.5 min,料液比1:15.3 (g/mL),在此条件下得到老山芹提取液对α-葡萄糖苷酶抑制率为69.52%±1.13%,α-淀粉酶抑制率为56.38%±0.96%,二者的IC₅₀分别为0.169、0.339 mg/mL。老山芹可以作为具有降血糖功能的抑制α-葡萄糖苷酶和α-淀粉酶的物质来源。     

Determination of antioxidant activity and phenolic compounds of Muntingia calabura Linn. peel by HPLC‐DAD and UPLC‐ESI‐MS/MS

Antioxidant activity in Muntingia calabura Linn. peel was evaluated by DPPH radical, ORAC, ABTS cation radical, FRAP assays and total phenolic contents by different extraction conditions. In addition, a method for determination of phenolic compounds in calabura peel samples harvested in Brazil using methanol:water and magnetic stirring as the extraction method, HPLC‐DAD and UPLC‐ESI‐MS/MS analysis were developed. Calabura peel showed antioxidant activity for all extraction conditions and assays evaluated, the most polar solvents being more effective. The developed HPLC‐DAD method allowed the accurate determination of phenolic compounds, with recoveries in the range of 72–107% and precision values ≤4%, with exception for chlorogenic acid. Gallic acid was determined at the highest concentration levels, followed by myricetin, ferulic acid and vanillic acid. However, all the five proposed phenolic compounds were identified in calabura peel samples by UPLC‐ESI‐MS/MS. Thus, calabura peel, an uncommon edible fruit part, can be appointed as a rich source of phenolic compounds.     

超高效液相色谱-质谱联用分析茶叶中酚酸类化合物的组成及分布

采用超高效液相色谱-串联质谱技术建立同时测定茶叶样品中游离型、游离酯型、结合型、可溶性糖苷型及不溶性糖苷型等不同形态酚酸的分析方法。以70%甲醇溶液直接提取样品中的游离型酚酸,该提取液分别以2 mol/L NaOH溶液（含1 g/100 mL抗坏血酸和10 mmol/L乙二胺四乙酸）和1 mol/L HCl溶液水解以释放游离酯型与可溶性糖苷型酚酸;提取后的样品残渣分别以碱水解、酸水解方式释放结合型与不溶性糖苷型酚酸。23 种酚酸类化合物在50～1 000 μg/L范围内呈良好线性关系,相关系数（r）均高于0.996,相对标准偏差小于8.84%;茶叶样品中游离型酚酸的回收率为71.14%～105.43%,游离酯型酚酸和可溶性糖苷型酚酸的回收率分别为82.81%～108.93%、39.09%～102.25%。在茶叶中鉴定出14 种酚酸类化合物,总含量范围为7.84～12.90 mg/g。