Antioxidant Effects and Phytochemical Properties of Seven Taiwanese Cirsium Species Extracts

In the present investigation, we compared the radical-scavenging activities and phenolic contents of seven Taiwanese Cirsium species with a spectrophotometric method. We further analyzed their phytochemical profiles with high-performance liquid chromatography–photodiode array detection (HPLC–DAD). We found that the flower part of Cirsium japonicum var. australe (CJF) showed the best radical-scavenging activities against 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and the hypochlorite ion, for which the equivalents were 6.44 ± 0.17 mg catechin/g, 54.85 ± 0.66 mmol Trolox/g and 418.69 ± 10.52 mmol Trolox/g respectively. CJF also had the highest contents of total phenolics (5.23 ± 0.20 mg catechin/g) and phenylpropanoids (29.73 ± 0.72 mg verbascoside/g). According to the Pearson’s correlation coefficient, there was a positive correlation between the total phenylpropanoid content and ABTS radical-scavenging activities (r = 0.979). The radical-scavenging activities of the phenylpropanoids are closely related to their reducing power (r = 0.986). HPLC chromatograms obtained in validated HPLC conditions confirm that they have different phytochemical profiles by which they can be distinguished. Only CJF contained silicristin (0.66 ± 0.03 mg/g) and silydianin (9.13 ± 0.30 mg/g). CJF contained the highest contents of apigenin (5.56 ± 0.09 mg/g) and diosmetin (2.82 ± 0.10 mg/g). Among the major constituents, silicristin had the best radical-scavenging activities against DPPH (71.68 ± 0.66 mg catechin/g) and ABTS (3.01 ± 0.01 mmol Trolox/g). However, diosmetin had the best reducing power and radical-scavenging activity against the hypochlorite anion (41.57 ± 1.14 mg mmol Trolox/g). Finally, we found that flavonolignans (especial silicristin and silydianin) and diosmetin acted synergistically in scavenging radicals.     

Comparative study on the antioxidant activities of extracts of Coreopsis tinctoria flowering tops from Kunlun Mountains,Xinjiang, north-western China

Coreopsis tinctoria flowering tops (CTFs) from the Kunlun Mountains in Xinjing (north-western China) have been used for tea production for about a century. This study aims to assess the antioxidant activities and total phenolic, flavonoid and proanthocyanidin contents of various solvent extracts of CTF. CTF was extracted using n-hexane, chloroform, ethyl acetate, n-butanol, 75% aqueous ethanol (AEE) and water. The antioxidant activities of the CTF extracts were investigated through DPPH, ABTS, ^*OH, ^*O₂^? , total antioxidant capacity and reducing power assays. The results showed that n-butanol extract showed the highest contents of total phenols and flavonoids, with DPPH, ABTS and ^*OH radical-scavenging activities with IC₅₀ values of 134, 90.72 and 13.8 μg mL^? 1, respectively. The AEE demonstrated the strongest DPPH and ABTS radical-scavenging activities, with IC₅₀ values of 103 and 75.16 μg mL^? 1, respectively. Given its high antioxidant effect, CTF is a good source of natural antioxidants or functional food materials.     

Antioxidant phenolic compounds of Dracaena cambodiana

The antioxidant activities of the petroleum ether, ethyl acetate, n-BuOH and water extract fractions from Dracaena cambodiana Pierre ex Gagnep were evaluated in this study. The ethyl acetate fraction contained the highest amount of total phenolics and total flavonoids, and showed the greatest DPPH˙, ABTS+ and Superoxide anion radical-scavenging capacities. The DPPH˙, ABTS+ and Superoxide anion radical-scavenging capacities of nine compounds isolated from the ethyl acetate fraction were also evaluated. The results indicated that these compounds contributed to the antioxidant activity of D. cambodiana. Therefore, D. cambodiana and these compounds might be used as natural antioxidants.     

GC/MS and LC-MS/MS phytochemical evaluation of the essential oil and selected secondary metabolites of Ajuga orientalis from Jordan and its antioxidant activity

The current investigation aimed to shed light in the volatile and non-volatile secondary metabolites of Ajuga orientalis L. from Jordan. GC/MS and GC/FID analysis of the hydrodistilled essential oil obtained from aerial parts of the plant revealed tiglic acid (18.90 %) as main constituent. Each of the methanol and butanol fractions of A. orientalis were screened for their total phenol content (TPC), total flavonoid content (TFC), and antioxidant activity determined by DDPH and ABTS methods. The extracts were then analyzed by LC-ESI-MS/MS to unveil their chemical constituents, especially phenols and flavonoids. Results showed that the AO-B extract had the highest TPC (217.63 ± 2.65 mg gallic acid/g dry extract), TFC (944.41 ± 4.77 mg quercetin /g dry extract), highest DPPH and ABTS antioxidant activity ((4.00 ± 0.20) × 10^-2; (3.00 ± 0.20) × 10^-2 mg/mL, respectively) as compared to the AO-M extract. LC-ESI-MS/MS analysis of both extracts revealed the presence of several phenolics, flavonoids and nonphenolic acids.     

Novel 1,3,4-thiadiazole conjugates derived from protocatechuic acid: Synthesis,antioxidant activity,and computational and electrochemical studies

A series of 15 novel 1,3,4-thiadiazole amide derivatives containing a protocatechuic acid moiety were synthesized and structurally characterized. In addition, the corresponding imino (4) and amino (5) analogues of a phenyl-substituted 1,3,4-thiadiazole amide derivative 3a were prepared to compare the effects of the structural changes on the radical-scavenging activity. The obtained compounds were examined for their antioxidative potential by 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. In addition, selected compounds were studied by density functional theory (DFT) and cyclic voltammetry experiments. The tested compounds showed high potential to scavenging DPPH radical and ABTS radical cation compared with the referent antioxidants ascorbic acid and nordihydroguaiaretic acid (NDGA). On the basis of the calculated thermodynamic parameters, it can be concluded that the sequential proton loss electron transfer (SPLET) mechanism represents the most probable reaction path in a polar solvent for DPPH radical–scavenging activity. On the other hand, the single electron transfer followed by proton transfer (SET-PT) can be a likely mechanistic pathway in the case of an ABTS radical cation.     

Proteome Analysis and In Vitro Antiviral,Anticancer and Antioxidant Capacities of the Aqueous Extracts of Lentinula edodes and Pleurotus ostreatus Edible Mushrooms

In this study, we examined aqueous extracts of the edible mushrooms Pleurotus ostreatus (oyster mushroom) and Lentinula edodes (shiitake mushroom). Proteome analysis was conducted using LC-Triple TOF-MS and showed the expression of 753 proteins by Pleurotus ostreatus, and 432 proteins by Lentinula edodes. Bioactive peptides: Rab GDP dissociation inhibitor, superoxide dismutase, thioredoxin reductase, serine proteinase and lectin, were identified in both mushrooms. The extracts also included promising bioactive compounds including phenolics, flavonoids, vitamins and amino acids. The extracts showed promising antiviral activities, with a selectivity index (SI) of 4.5 for Pleurotus ostreatus against adenovirus (Ad7), and a slight activity for Lentinula edodes against herpes simplex-II (HSV-2). The extracts were not cytotoxic to normal human peripheral blood mononuclear cells (PBMCs). On the contrary, they showed moderate cytotoxicity against various cancer cell lines. Additionally, antioxidant activity was assessed using DPPH radical scavenging, ABTS radical cation scavenging and ORAC assays. The two extracts showed potential antioxidant activities, with the maximum activity seen for Pleurotus ostreatus (IC50 µg/mL) = 39.46 ± 1.27 for DPPH; 11.22 ± 1.81 for ABTS; and 21.40 ± 2.20 for ORAC assays. This study encourages the use of these mushrooms in medicine in the light of their low cytotoxicity on normal PBMCs vis à vis their antiviral, antitumor and antioxidant capabilities.     

Cyclopeptides and polyketides from coral-associated fungus, Aspergillus versicolor LCJ-5-4

Three new cyclopentapeptides, versicoloritides A-C (1-3), a new orcinol tetramer, tetraorcinol A (4), and two new lactones, versicolactones A and B (5 and 6) together with three known metabolites, diorcinol, glyantrypine, and cordyol C were isolated from the fermentation broth of the coral-associated fungus Aspergillus versicolor LCJ-5-4. Their structures were elucidated by spectroscopic and chemical methods. The new compounds 1-4 were evaluated for their radical-scavenging activity and antimicrobial activity against Staphylococcus aureus, Escherichia coli, Enterobacter aerogenes, Bacillus subtilis, Pseudomonas aeruginosa, and Candida albicans and cytotoxicity against P388 and Hela cell lines. Compound 4 showed weak radical-scavenging activity against the DPPH radical with an IC₅₀ value of 67 μM.     

Antioxidant activity of papaya seed extracts

The antioxidant activities of the ethanol, petroleum ether, ethyl acetate, n-butanol and water extract fractions from the seeds of papaya were evaluated in this study. The ethyl acetate fraction showed the strongest DPPH and hydroxyl free radical-scavenging activities, and its activities were stronger than those of ascorbic acid and sodium benzoate, respectively. The n-butanol fraction demonstrated the greatest ABTS? radicals scavenging activity. The ethyl acetate fraction and the n-butanol fraction not only showed higher antioxidant activities than the petroleum ether fraction, water fraction and ethanol fraction, but also showed higher superoxide anion and hydrogen peroxide radicals scavenging activities than those of the other extract fractions. The high amount of total phenolics and total flavonoids in the ethyl acetate and n-butanol fractions contributed to their antioxidant activities. The ethyl acetate fraction was subjected to column chromatography, to yield two phenolic compounds, p-hydroxybenzoic acid and vanillic acid, which possessed significant antioxidant activities. Therefore, the seeds of papaya and these compounds might be used as natural antioxidants.     

Assessment of antioxidant activities of three wild medicinal plants from Bahrain

This study reports the antioxidant properties of three wild medicinal plants from Bahrain, namely Aizoon canariense L., Asphodelus tenuifolius Cav., and Emex spinosus (L.) Campdera. Antioxidant and antiradical activities of dried materials of these plants were investigated using FRAP, DPPH and ABTS assays. Total phenolics, free phenolics and total flavonoids were also determined. E. spinosus was ranked by the assays as the plant possessing the highest antioxidant and antiradical activities with an average FRAP value of 1.84 mmol/g and IC₅₀ of 10.7 and 7.75 mg/ml for DPPH and ABTS assays, respectively. A. tenuifolius ranked second with a mean FRAP value of 0.69, IC₅₀ DPPH of 1.72 and ABTS of 0.36. A. canariense possessed the lowest activities with a mean FRAP value of 0.6, and averaged IC₅₀ of 103.8 and ABTS of 14.6. E. spinosus possessed the highest content of free phenolics (mg/100 g) (64.64) followed by A. tenuifolius (45.21) and A. canariense (32.23). E. spinosus also exhibited the highest total flavonoids with an average 82.71 mg/100 g followed by A. canariense (55.92) and A. tenuifolius (49.10). The studied medicinal plants possess considerable antioxidant activities and may contribute to the well-being of individuals who consume them.     

New Insights on Acanthus ebracteatus Vahl: UPLC-ESI-QTOF-MS Profile,Antioxidant, Antimicrobial and Anticancer Activities

This study investigated the antioxidant, antimicrobial, anticancer, and phytochemical profiling of extracts from the leaves and stem/root of Acanthus ebracteatus (AE). The total phenolic content (TPC), total flavonoid content (TFC), 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) radical-scavenging activity, 2, 2′-azino-Bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical-scavenging activity, metal chelating activities (MCA), ferric reducing antioxidant power (FRAP) and oxygen radical antioxidant capacity (ORAC) were used for antioxidant assessment. The ethanolic extracts of the leaves (AEL-nor) and stem/root (AEWP-nor) without chlorophyll removal and those with chlorophyll removal, using sedimentation process (AEL-sed and AEWP-sed), were prepared. Generally, AEL-sed showed the highest antioxidant activity (FRAP: 1113.2 µmol TE/g; ORAC: 11.52 µmol TE/g; MCA: 47.83 µmol EDTA/g; ABTS 67.73 µmol TE/g; DPPH 498.8 µmol TE/g; TPC: 140.50 mg/GAE g and TFC: 110.40 mg/CE g) compared with other extracts. Likewise, AEL-sed also showed the highest bacteriostatic (MIC) and bactericidal (MBC) effects, as well as the highest anticancer and antiproliferative activity against oral squamous carcinoma (CLS-354/WT) cells. UPLC-ESI-QTOF/MS analysis of AEL-sed and AEWP-sed tentatively identified several bioactive compounds in the extracts, including flavonoids, phenols, iridoids, and nucleosides. Our results provide a potentially valuable application for A. ebracteatus, especially in further exploration of the plant in oxidative stress-related disorders, as well as the application of the plant as potential nutraceuticals and cosmeceuticals.     

Bromination of phenols in bromoperoxidase-catalyzed oxidations

Phenol and ortho-substituted derivatives furnish products of selective para-bromination, if treated with sodium bromide, hydrogen peroxide, and the vanadate(V)-dependent bromoperoxidase I from the brown alga Ascophyllum nodosum. Relative rates of bromination in morpholine-4-ethane sulfonic acid (MES)-buffered aqueous tert-butanol (pH 6.2) increase by a factor 32, as the ortho-substituent in a phenol changes from F via Cl, OCH₃, C(CH₃)₃, and H to CH₃. The polar effect in phenol bromination by the enzymatic method, according to a Hammett-correlation (ρ=−3), compares to reactivity of molecular bromine under identical conditions (ρ=−2). Hypobromous acid is not able to electrophilically substitute bromine for hydrogen at pH 6.2 in aqueous tert-butanol. The tribromide anion behaves in MES-buffered aqueous tert-butanol as electrophile (ρ∼−3), showing a similar polar effect in phenol bromination as molecular bromine.     

Antioxidant activity of protein hydrolysates from aqueous extract of velvet antler (Cervus elaphus) as influenced by molecular weight and enzymes

The crude protein hydrolysates from aqueous extract of velvet antler (AEVA) were prepared by simulated gastrointestinal digestion (SGI, pepsin-pancreatin) using pancreatin-pepsin, alcalase and neutrase. The resulting hydrolysates were separated by sequential ultrafiltration into four fractions. The antioxidant activities of peptide fractions were evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, ferric reducing antioxidant power (FRAP), 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging and Fe(2+)-chelating assays. Results showed that the hydrolysate prepared by SGI had a low degree of hydrolysis, which was significantly improved with altered proteases, such as pancreatin-pepsin and alcalase. Antioxidant activities of peptide fractions varied with molecular weight (MW) and the enzyme used. Generally, low-MW peptide fractions had higher ABTS radical scavenging activity and Fe(2+)-chelating ability, and high-MW peptide fractions were more effective in DPPH radical scavenging activity and reducing power.     

Synthesis,biological evaluation,quantitative-SAR and docking studies of novel chalcone derivatives as antibacterial and antioxidant agents

In the present study, a series of chalcone derivatives including 17 new compounds were synthesised; their antibacterial activities against eleven bacteria, and their free radical-scavenging activities using DPPH were evaluated. All compounds showed significant antibacterial activities against both Gram-positive and Gram-negative bacteria. In particular, compound IIIf strongly inhibited Staphylococcus aureus (JMC 2151) and Enterococcus faecalis (CARS 2011-012) with MIC values of 6.25 µg mL^?1 and 12.5 µg mL^?1, respectively, which are comparable to that of the standard antibiotic, nalidixic acid. Compound IIIg also inhibited S. aureus with a MIC value similar to that of nalidixic acid (6.25 µg mL^?1). Furthermore, like nalidixic acid (MIC value of 25 µg mL^?1), compounds IIIa, IIIc and IIId inhibited Listeria monocytogenes (ATCC 43256) with MIC values of 25 µg mL^?1, 12.5 µg mL^?1 and 25 µg mL^?1, respectively. Quantitative structure-activity relationship (Q-SAR) studies using physicochemical calculations indicated that the antibacterial activities of chalcone derivatives correlated well with predicted physicochemical parameters (logP and PSA). Docking simulation by positioning the most active compound IIIf in the active site of the penicillin-binding protein (PBP-1b) of S. aureus was performed to explore the feasible binding mode. Furthermore, most of the compounds synthesised exhibited significant DPPH radical-scavenging activity, although compounds IIc and IIIc exhibited the greatest antioxidant activity with IC₅₀ values of 1.68 µM and 1.44 µM, respectively, comparable to that of the standard antioxidant, ascorbic acid (1.03 µM).     

Moringa oleifera leaves from Brazil: Influence of seasonality,regrowth age and,region in biochemical markers and antioxidant potential

Moringa oleifera leaves are cultivated in warm regions of Brazil for commercial ends due to their nutritional and biological properties. This study evaluated, by chemometric tools, the influence of seasonality (winter, spring, autumn, and summer), growing area in Brazil (South, Southeast, and Northeast), and regrowth age (40 and 80 days) in antioxidant potential, and biochemical markers determined by HPLC-DAD. The results obtained in the present study showed that all the parameters evaluated were affected by seasonality, regrowth age, and growing region. The content of phenolic compounds and antioxidant activity using the ABTS method was higher in samples cultivated in the southeast (59.4 mg GAE g^?1 and 346 µmol TEAC g^?1, respectively). The highest antioxidant activities evaluated by DPPH and FRAP methods were obtained from leaves of the southeast and northeast. In addition, young leaves presented higher antioxidant potential and total phenolic content. The cultivation region significantly influenced the content of chlorogenic acid, isoquercitrin, and astragalin, which ranged from 4.2 to 7.2 mg g^?1, 8.0 to 10.7 mg g^?1, and 2.2 to 3.8 mg g^?1, respectively. In addition, a positive correlation between solar radiation and temperature with caffeic acid, rutin, phenolic compounds, and antioxidant assay from the DPPH method was observed. Additionally, the RGB pattern of the images of these leaves was correlated with the levels of compounds with antioxidant activity. Models generated through machine learning showed good performances, and ABTS and rutin analyses developed the best models with a coefficient of determination above 75 %. Thus, color patterns can be used to measure the antioxidant activity by the ABTS method and to determine the rutin concentration in M. oleifera leaves.     

Synthesis and antioxidant properties of novel α-tocopherol glycoconjugates

Glycoconjugates of α-tocopherol (1), synthesized using click chemistry between α-tocopherol-azide and glyco-alkynes are solids, have enhanced water solubility and exhibit radical-scavenging activities comparable to 1, as determined by DPPH and lipid peroxidation assay methods.     

Antioxidant,cholinesterase inhibition activities and essential oil analysis of Nelumbo nucifera seeds

Nelumbo nucifera seeds’ essential oil (EO), crude extract and subsequent fractions were evaluated for their DPPH, ABTS and superoxide anion-free radical scavenging and cholinesterase inhibitory activities. The ethyl acetate fraction and EO showed outstanding antioxidant activities with IC₅₀ values of 191, 450 μg/mL (DPPH), 123, 221 μg/mL (ABTS) and 69, 370 μg/mL (superoxide anion). The ethyl acetate fraction and EO also caused significant inhibition of acetylcholinesterase and butyrylcholinesterase with IC₅₀ values of 70 ± 0.6, 64 ± 0.8 and 75 ± 0.3, 58 ± 0.2, in dose-dependent manner. The first ever gas chromatography–mass spectrometry analysis of the EO obtained from N. nucifera seeds resulted in identification of 19 constituents, mainly comprised of oxygenated sesquiterpenes responsible for their promising bioactivity. The crude and fractions revealed the presence of saponins, flavonoids, steroids, alkaloids, terpenoids and cardiac glycosides in phytochemical investigation.     

Antioxidant potential and radical-scavenging effects of flavonoids from the leaves of Psidium cattleianum grown in French Polynesia

Psidium cattleianum J. Sabine (Myrtaceae) is a traditional medicinal plant in French Polynesia. The leaves and roots possess many medicinal properties. These effects may be correlated with the presence of antioxidant compounds. Seven flavonoids along with a benzoic acid were isolated from the leaves of P. cattleianum. The compounds indicated strong antioxidant and radical-scavenging activities in ALP, DPPH(·), ABTS(·-) and ORAC assays. This study demonstrates that the leaves of P. cattleianum possess main compounds with interesting antioxidant and radical-scavenging activities, as clarified by four biological assays. Our findings may justify the use of these leaves in the traditional medicine of French Polynesia. Among the total eight known compounds, reynoutrin and luteolin were isolated for the first time from the genus Psidium.     

Synthesis and Evaluation of Antioxidant Properties of 2-Substituted Quinazolin-4(3H)-ones

Quinazolinones represent an important scaffold in medicinal chemistry with diverse biological activities. Here, two series of 2-substituted quinazolin-4(3H)-ones were synthesized and evaluated for their antioxidant properties using three different methods, namely DPPH, ABTS and TEAC_CUPRAC, to obtain key information about the structure–antioxidant activity relationships of a diverse set of substituents at position 2 of the main quinazolinone scaffold. Regarding the antioxidant activity, ABTS and TEAC_CUPRAC assays were more sensitive and gave more reliable results than the DPPH assay. To obtain antioxidant activity of 2-phenylquinazolin-4(3H)-one, the presence of at least one hydroxyl group in addition to the methoxy substituent or the second hydroxyl on the phenyl ring in the ortho or para positions is required. An additional ethylene linker between quinazolinone ring and phenolic substituent, present in the second series (compounds 25a and 25b), leads to increased antioxidant activity. Furthermore, in addition to antioxidant activity, the derivatives with two hydroxyl groups in the ortho position on the phenyl ring exhibited metal-chelating properties. Our study represents a successful use of three different antioxidant activity evaluation methods to define 2-(2,3-dihydroxyphenyl)quinazolin-4(3H)-one 21e as a potent antioxidant with promising metal-chelating properties.     

Studies on the potential antioxidant properties of Senecio stabianus Lacaita (Asteraceae) and its inhibitory activity against carbohydrate-hydrolysing enzymes

This study showed for the first time the antioxidant and hypoglycaemic properties of the methanol, n-hexane and ethyl acetate extracts from Senecio stabianus Lacaita, a plant that belongs to the Asteraceae family. The antioxidant activities were carried out using two different in vitro assays, namely 2,2-diphenyl-1-picrylhydrazyl (DPPH) test and 2,2'-azinobis(3-ethylbenzthiazoline-6-sulphonate) (ABTS) test. The ethyl acetate extract showed the highest activity with inhibitory concentration 50% (IC(50)) values of 35.5 and 32.7?μg?mL(-1) on DPPH test and ABTS test, respectively. This activity may be related to a good total phenol and flavonoid content. All extracts were also tested for their potential inhibitory activity of α-amylase and α-glucosidase digestive enzymes. The n-hexane extract exhibited the highest α-amylase inhibition with an IC(50) value of 0.21?mg?mL(-1). Through bioassay-guided fractionation processes seven fractions (A-G) were obtained and tested. Based on the phytochemical analysis, the activity of n-hexane extract may be related to the presence of monoterpenes and sesquiterpenes.