Identification of phenolic antioxidants from Sword Brake fern (Pteris ensiformis Burm.)

Sword Brake fern (Pteris ensiformis Burm.) is one of the most common ingredients of traditional herbal drinks in Taiwan. In an effort to identify antioxidants from the aqueous extract of Sword Brake fern (SBF), the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity-guided isolation was employed. Three new compounds, kaempferol 3-O-α-l-rhamnopyranoside-7-O-[α-d-apiofuranosyl-(1-2)-β-d-glucopyranoside] (1), 7-O-caffeoylhydroxymaltol 3-O-β-d-glucopyranoside (3) and hispidin 4-O-β-d-glucopyranoside (4), together with five known compounds, kaempferol 3-O-α-l-rhamnopyranosid-7-O-β-d-glucopyranoside (2), caffeic acid (5), 5-O-caffeoylquinic acid (6), 3,5-di-O-caffeoylquinic acid (7) and 4,5-di-O-caffeoylquinic acid (8) were isolated and determined on the basis of spectroscopic analyses. HPLC with UV detector was further employed to analyze the content of each compound in SBF based on the retention time by comparison with isolated pure compounds. It was found that the most abundant phenolic compound was compound 3, followed by compounds 7 and 4. The di-O-caffeoylquinic acids (7 and 8) have the strongest DPPH scavenging potential with IC₅₀ around 10 μM and the highest Trolox equivalent antioxidant capacity (TEAC) about 2 mM. This data indicates that SBF is rich in phenolic antioxidants.     

Identification and evaluation of antioxidants defatted Camellia oleifera seeds by isopropanol salting-out pretreatment

Seven flavonoid glycosides (1–7) and one theasaponin (8) were isolated from the defatted Camellia oleifera seeds using the isopropanol salting-out pretreatment (ISP) technique, followed by column chromatography. Among them, compounds 5, 7, and 8 are new compounds. The comparison of oxygen radical absorbance capacity (ORAC) of crude extracts extracted by the n-butanol partition (BP) with those extracted by the ISP showed that the latter method yields eight times greater scavenging capacities than that of the former approach. Besides, ISP exhibited almost twice the extraction efficiency than that of BP. ORAC and Trolox equivalent antioxidant capacity (TEAC) analysis revealed that the most potent antioxidants are compounds 1 and 2, which exhibited 1.78 and 1.41 times higher antioxidant activity than that of Trolox, respectively. These results indicated that the ISP approach improves the extraction efficiency in the isolation of potent antioxidants, making the defatted C. oleifera seeds valuable in the food additive industry.     

TLC bioautography-guided isolation of antioxidants from fruit of Perilla frutescens var. acuta

Guided isolation through bioautography on TLC using 1,1-diphenyl-2-picryl-hydrazyl radical (DPPH) as a detection reagent led to the isolation of four antioxidant compounds from fruit of Perilla frutescens var. acuta. These compounds were identified as rosmarinic acid (1), luteolin (2), apigenin (3), and chrysoeriol (4), by means of UV, NMR, and ESI MS. All the compounds were isolated for the first time from the fruit of the plant. Compounds 1 and 2 showed significant DPPH scavenging capacities, with IC₅₀ values of 8.61 and 7.50 μM, respectively. Further quantitative HPLC analysis confirmed that compounds 1-4 are the predominant contributors to the free radical scavenging activity of the extract of P. frutescens var. acuta.     

Screening,determination and quantification of major antioxidants from Balanophora laxiflora flowers

In this study, antioxidant phytochemicals of Balanophora laxiflora flowers were detected by online HPLC–DPPH method. Accordingly, five phytochemicals including 1-O-(E)-caffeoyl-β-d-glucopyranose (1), 1-O-(E)-p-coumaroyl-β-d-glucopyranose (2), caffeic acid (3), 1,3-di-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-β-d-glucopyranose (4), and 1-O-(E)-caffeoyl-4,6-(S)-hexahydroxydiphenoyl-β-d-glucopyranose (5) were isolated using the developed screening method. Of these, compounds 1 and 5 were found to be major bioactive phytochemicals, and their contents were determined to be 10.8 mg and 9.5 mg per gramme of crude extract, respectively. In addition, compared with (+)-catechin, a well-known antioxidant, compounds 4 and 5 exhibited stronger DPPH radical and superoxide radical scavenging activities than (+)-catechin. These results demonstrated that the flower extracts of B. laxiflora have excellent antioxidant activities and thus have great potential as a source for natural health products.     

Optimisation of antioxidants extraction from soybeans fermented by Aspergillus oryzae

The extraction of antioxidant compounds from soybeans fermented with Aspergillusoryzae was optimised using a factorial design. A kinetic study of the total phenolic production and DPPH radical scavenging activity was first performed at the points selected in the factorial design. In both cases, the experimental profiles were fitted to a modified first-order kinetic model. To investigate the combined effects of temperature and solvent concentration on the extraction, the parameters obtained from the fitted kinetic models were used as response variables in a rotatable second-order design with quintuple replications in the centre of the experimental domain. The results obtained indicate that temperature had the most significant effect. The response surfaces show a maximum in the experimental domain studied. The optimum conditions for the extraction of total phenolic content were 65.3 °C and 73.1% ethanol, in which 56.2 mg of GAE/g were predicted. A scavenging activity of 81.6% DPPH radical was predicted at the optimum conditions of 61.6 °C and 60% ethanol.     

Phenolic antioxidants from Chinese toon (fresh young leaves and shoots of Toona sinensis)

Chinese toon (the fresh young leaves and shoots of Toona sinensis), known as a tree vegetable, belongs to the family of Meliaceae. It is one of the most popular vegetables in China. The 80% acetone extract of Chinese toon exhibited considerable antioxidant activity in the 1,1-diphenyl-2-picryldydrazyl (DPPH) radical-scavenging assay. Bioassay-guided purification of the extract led to the isolation of 12 phenolic compounds (1–12), whose structures were determined by detailed spectroscopic analyses, including UV, IR, MS, 1D and 2D NMR techniques. Of them, compounds 3–8 and 11 were isolated from T. sinensis for the first time. All of the isolated compounds were examined for their antioxidant activities by the DPPH method, and the results showed that gallic acid and its derivatives, gallotannins and flavonoids were the main constituents contributing to the antioxidant activity of Chinese toon. From the health point of view, Chinese toon is an ideal dietary vegetable with natural antioxidants.     

Insecticidal activity of asarones identified in Acorus gramineus rhizome against three coleopteran stored-product insects

The insecticidal activities of Acorus gramineus rhizome-derived materials against adults of Sitophilus oryzae (L.), Callosobruchus chinensis (L.) and Lasioderma serricorne (F.) were examined using direct contact application and fumigation methods. The biologically active constituents of the Acorus rhizome were characterized as the phenylpropenes (Z)- and (E)-asarones by spectroscopic analysis. Responses varied with insect species, compound and exposure time rather than dose. In a filter paper diffusion test, (Z)-asarone caused 70% and 90% mortality against S. oryzae adults at 0.064 and 0.255 mg/cm² at 4 days after treatment, respectively, with 100% mortality at 7 days after treatment. (E)-Asarone at 0.255 mg/cm² was almost ineffective against S. oryzae adults at 7 days after treatment. Against C. chinensis adults at 0.064 mg/cm², (Z)- and (E)-asarones gave 100% mortality at 3 and 7 days after treatment, respectively. Against L. serricorne adults, (Z)-asarone gave 90% and 83% mortality at 0.255 and 0.064 mg/cm² at 7 days after treatment, respectively, whereas (E)-asarone at 0.255 mg/cm² was almost ineffective at 7 days after treatment. These results indicate that the toxicity of asarones might be due to the cis configuration rather than to the position of the double bond. In a fumigation test, (Z)-asarone at 0.577 mg/cm² was much more effective against adults of all three insect species in sealed containers than in open ones, indicating that the insecticidal activity of the compound was largely attributable to fumigant action.     

Raw Millefiori honey is packed full of antioxidants

Total polyphenols, flavonoids and antioxidant power of raw honey samples from two of the most common Italian varieties, i.e., Millefiori and Acacia, were evaluated. Phenolic content, expressed as caffeic acid equivalents, ranged from 12.5 to 17.5 mg/100 g and from 3 to 11 mg/100 g in Millefiori and Acacia honeys, respectively. All Millefiori samples exhibited the highest flavonoid concentration being between 1.23 and 2.93 mg catechin equivalents (CE)/100 g honey. Total flavonoids in 100 g Acacia honeys were in the range of 0.45–1.01 mg CE. Acacia honeys had lower total antioxidant power, as assessed by ferric reducing/antioxidant power assay, than Millefiori. The relationship between phenolic content and antioxidant power was discussed. Comparative experimental analysis was performed with an artificial honey and processed honeys. Raw Millefiori honey is rich in both amount and variety of antioxidant substances, and its inclusion in the diet may be recommended to complement other polyphenol sources.     

Anti-proliferative and potential anti-diabetic effects of phenolic-rich extracts from edible marine algae

Phenolic-rich extracts from four edible marine macroalgae commonly found in UK waters were tested for their potential biological effects towards cultured colon cancer cells and for their ability to inhibit digestive enzymes to achieve potential anti-diabetic effects. Extracts from Palmaria, Ascophyllum and Alaria, but not Ulva, gave reasonable recoveries of phenolics and inhibited the proliferation of colon cancer cells in a dose-responsive manner. Alaria extracts were more effective than Palmaria or Ascophyllum extracts, but Palmaria and Ascophyllum would provide greater amounts of phenolics per gram intake.     

New diarylheptanoids from the rhizome of Alpinia officinarum Hance

Three diarylheptanoids, officinaruminane A (1), officinaruminane B (2), 5(S)-acetoxy-7-(4-dihydroxyphenyl)-1-phenyl-3-heptanone (3), together with six known ones , (5R)-5-hydroxy-1-(4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-3-heptanone (4),(5R)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4,5-dihydroxy-3-methoxyphenyl)-3-heptanone (5), 1-phenyl-7-(4-hydroxy-3-methoxyphenyl)-4E-en-3-heptanone (6), 1-(4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-4E-en-3-heptanone (7), 1-phenyl-7-(4-hydroxyphenyl)- 4E- en-3-heptanone (8), and 3,6-furan-7-(4′′-hydroxy-3′′-methoxyphenyl)-1-phenylheptane (9), were isolated from the rhizomes of Alpinia officinarum Hance by column chromatography on silica gel, MPLC and preparative thin-layer chromatography (TLC). The structures of these compounds were elucidated on the basis of mass spectrometry, ¹H NMR, ¹³C NMR, HMQC and HMBC data. Among them, 1 is a diarylheptanoid with a pyridine ring, and 2 is a diarylheptane monoterpene.     

Effect of antioxidants and competing mycoflora on Fusarium verticillioides and F. proliferatum populations and fumonisin production on maize grain

This study was carried out to determine the temporal effect of the antioxidants butylated hydroxyanisol (BHA) and propyl paraben (PP) at doses of 500 and 1000 μg/g on the growth of Fusarium verticillioides and F. proliferatum inoculated on natural maize grain in the presence of the competing mycoflora and fumonisin production at 0.98 and 0.95 water activity (a_w) over a 28-day storage period. The reduction in the log colony forming units (CFU) of Penicillium, Aspergillus and Fusarium populations was 10-100 fold depending on dose of BHA or PP, a_w and time. However, the populations of all three groups were higher at 0.98 a_w than 0.95 a_w. BHA at 500 μg/g and 0.95 a_w reduced the fumonisin content by 82% after 7-14 days incubation, but at the end of the experimental period the reduction was only 32%. A higher reduction in the level of fumonisin produced (77%) was achieved with BHA at 1000 μg/g after 28 days. PP at 500 and 1000 μg/g decreased fumonisin production throughout the incubation period in the drier treatment, but at 0.98 a_w control of toxin production was only achieved after 7-14 days. The reduction in the fumonisin levels could be due to the combined effect of antioxidants, and the competing mycoflora, mainly Aspergillus and Penicillium species.     

Effects of binary solvent extraction system,extraction time and extraction temperature on phenolic antioxidants and antioxidant capacity from mengkudu (Morinda citrifolia)

An investigation into the effects of ethanol concentration (0–100%, v/v), extraction time (20–120 min) and extraction temperature (25–65 °C) on the extraction of phenolic antioxidants from mengkudu (Morinda citrifolia) was performed using a single-factor experiment. Total phenolic content (TPC) and total flavonoid content (TFC) assays were used for determination of phenolic compounds. Antioxidant capacity was evaluated by measuring the scavenging effect on 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) and 2,2′-diphenyl-1-picrylhydrazyl (DPPH) radicals. Experimental results showed that extraction conditions had significant effect on extraction of phenolic compounds and antioxidant capacities. The optimised conditions were 40% ethanol for 80 min at 65 °C, with values of 919.95 mg GAE/100 g DW for TPC, 472.73 mg CE/100 g DW for TFC, 791.71 μmol TEAC/100 g DW for ABTS and 1928.5 μmol TEAC/100 g DW for DPPH. TPC was significantly correlated with DPPH under the effects of ethanol concentration (r = 0.932) and extraction time (r = −0.938).     

Integrated management of insect vectors of Aspergillus flavus in stored maize, using synthetic antioxidants and natural phytochemicals

The purpose of this study was to investigate the insecticidal activity of two benzoic acids 2(3)-tert-butyl-4 hydroxyanisole (BHA) and 2,6-di(tert-butyl)-p-cresol (BHT); two phenolic acids 3-phenyl-2-propenoic acid (CA) and trans-4-hydroxy-3-methoxycinnamic acid (FA) and two essential oils of Eugenia caryophyllata (clove tree) and Thymus vulgaris (thyme) against Sitophilus zeamais, Tribolium confusum and Rhyzopertha dominica, vector carriers of aflatoxigenic fungi in stored maize. The susceptibility of insects, the frequency of isolation of Aspergillus section Flavi in insects and maize, and the analysis of aflatoxin B₁ in maize were determined. BHA, BHT, BHA/BHT mixture and the natural phytochemicals AF and AF/AC mixture showed the highest insecticidal activity against S. zeamais, T. confusum and R. dominica after 120 days of incubation. The insecticidal efficacy of the volatile fraction of essential oils of clove and thyme showed less inhibition. There was no contamination of Aspergillus section Flavi in dead and live insects collected from maize treated with BHA. No aflatoxin B₁ accumulation was detected in the control and treatments. The information obtained shows that these substances have the potential to control pest insect vectors of aflatoxigenic fungi in stored maize in microcosms during 120 days.     

Activity guided isolation of antioxidants from the leaves of Ricinus communis L.

An activity-guided isolation and purification process was used to identify the DPPH (l,l-diphenyl-2-picrylhydrazyl) free radical scavenging components of the food plant (Ricinus communis L.) of Eri silkworm. Dry leaves of R. communis L. were extracted with different solvents and tested for their antioxidant activity against DPPH^•. The MeOH:water (8:2) extract showed strong DPPH radical-scavenging activity, and was subjected to column chromatography over silica gel. Gallic acid, quercetin, gentisic acid, rutin, epicatechin and ellagic acid were isolated as active components and characterised by different spectroscopic techniques.     

In vitro antioxidant capacity of honeybee-collected pollen of selected floral origin harvested from Romania

Total phenolic phytochemical concentration was measured in 12 honeybee-collected pollens of selected floral species as well as their antioxidant capacity. The content of total polyphenols was measured spectrophotometrically using the Folin–Ciocalteu reagent with gallic acid as standard. The antioxidant properties were evaluated by 2,2-diphenyl-picrylhydrazyl radical scavenging capacity (DPPH) assay, Trolox equivalent antioxidant Capacity procedure and Ferric ion reducing antioxidant power assay. A great variability regarding the correspondence between the antioxidant activity and the content of total polyphenols of honeybee-collected pollens with different botanical origin was found. Antioxidant activities were different for each floral species and were not clearly associated to their total phenolic content.     

Antioxidant properties of different cultivars of Portulaca oleracea

Methanolic extracts of six cultivars of Portulaca oleracea were analyzed for their total phenol content (TPC) using the Folin–Ciocalteu method. The antioxidant activity was measured using the 1,1-diphenyl-2-picrylhydrazyl, ferric-reducing antioxidant power (FRAP) and β-carotene bleaching (BCB) assays. The iodine titration method was used to determine the ascorbic acid content (AAC). The TPC of the cultivars of P. oleracea ranged from 127 ± 13 to 478 ± 45 mg GAE/100 g of fresh weight of plant. There was good correlation between the TPC value and its AEAC, IC₅₀ and FRAP values (r² > 0.9) for all the cultivars. The AAC for the cultivars ranged from 38.5 ± 0.6 to 73.0 ± 17.5 mg/100 g. The TPC value of the common variety PO1, was the lowest compared to the ornamental cultivars (PO2–PO6). The BCB assay showed that all cultivars were capable of inhibiting lipid peroxidation and the inhibition power did not correlate with TPC value.     

Exploiting Catharanthus roseus roots: Source of antioxidants

Catharanthus roseus is among the most important medicinal plants, mainly due to its anticancer alkaloids.