Identification,characterisation, and quantification of phenolic compounds in the antioxidant activity-containing fraction from the seeds of Korean perilla (Perilla frutescens) cultivars

The present research was the first to investigate phenolic compound profiles and antioxidant properties in the seeds of various perilla (Perilla frutescens) cultivars. The 80% methanol extract (50 μg/ml) of this species showed potent antioxidant activities against 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radicals. Phenolic compounds were characterised by nuclear magnetic resonance (NMR) spectroscopy, and ultra performance liquid chromatography with photodiode array detector and electrospray ionisation/mass (UPLC-PDA-ESI/MS) analysis. Nine compounds were elucidated as caffeic acid-3-O-glucoside (1), caffeic acid (2), luteolin-7-O-glucoside (3), apigenin-7-O-glucoside (4), rosmarinic acid-3-O-glucoside (5), rosmarinic acid (6), luteolin (7), apigenin (8), and chrysoeriol (9). The individual and total phenolic contents were remarkably different, especially rosmarinic acid-3-O-glucoside (5) and rosmarinic acid (6) which were the predominant compounds (>95%) in all perilla cultivars. Additionally, Yeupsil cultivar exhibited the highest phenolic content (5029.0 μg/g) and antioxidant activity, whereas the lowest was shown by Dasil (2138.7 μg/g). Therefore, these results suggest that antioxidant effects of perilla seeds are correlated with phenolic contents.     

Evaluation of antioxidant activities of various solvent extracts of Carissa opaca fruits

The chloroform and aqueous fractions of Carissa opaca fruit, a traditional medicinal fruit in Pakistan possessed a high amount of total phenolic and flavonoid contents as compare to other solvent fractions with potent antioxidant activities in scavenging DPPH, superoxides, hydroxyl, hydrogen peroxide, ABTS radicals, and had strong iron chelating activity. On the other hand, the ethyl acetate fraction showed the highest inhibition of β-carotene linoleic acid peroxidation and phosphomolybdate assay. A high correlation coefficient existed between EC₅₀ values of DPPH, superoxides, hydroxyl, hydrogen peroxide, ABTS radicals, total phenolics and flavonoids, but a non significant correlation was found in the case of iron chelaters, β-carotene and phosphomolybdate assay. This study verified that the chloroform and aqueous fractions have strong antioxidant activities which were correlated with its high level of phenolics and flavonoids. These fractions can be used as a source of potential antioxidant or functional food material.     

Anthocyanin compositions and biological activities from the red petals of Korean edible rose (Rosa hybrida cv. Noblered)

The objectives of the present study were to investigate anthocyanin profiles and their biological properties, including antioxidant, anticancer, and antiallergic, from the red petals of Korean edible rose (Rosa hybrida cv. Noblered). The acidic methanol extract of this species showed potent biological activities at a concentration of 50 μg/mL. Its anthocyanins were characterised as cyanidin 3,5-di-O-glucoside and pelargonidin 3,5-di-O-glucoside using reversed-phase C₁₈ column chromatography, NMR spectroscopy, and HPLC-DAD-ESI/MS analysis. Cyanidin 3,5-di-O-glucoside was the predominant constituent (375 mg/100 g), representing about 85% of total content. Cyanidin 3,5-di-O-glucoside exhibited good scavenging activity against DPPH radical with IC₅₀ value of 55.2 μg/mL; pelargonidin 3,5-di-O-glucoside showed potent anticancer effects against LNCap (human prostate cell line), ACHN (human renal cell line) and MOLT-4F (human leukaemia cell line) cell cultures, with IC₅₀ values of 6.43, 18.3, and 6.78 μg/mL, respectively. Antiallergic activities were only moderate.     

Flavonols, betacyanins content and antioxidant activity of cactus Opuntia macrorhiza fruits

Flavonols, betacyanins content and antioxidant activity of red-purple cactus Opuntia macrorhiza fruits, a promising cactus pear species, were evaluated in comparison to the well known cactus pear fruits of Opuntia ficus-indica. Flavonol profile was evaluated by HPLC-DAD prior to and after enzymatic hydrolysis (glycosides vs. aglycons). In addition betacyanins, responsible for the purple to red color of cactus pear fruits were also estimated and compared to Beta vulgaris ssp. (roots) and red O. ficus-indica fruits. In all cases, cactus fruit pulps showed no flavonols at all. While different derivatives of isorhamnetin glycosides were found in O. ficus-indica fruit's peel, isorhamnetin-3-O-rutinoside was the only compound in O. macrorhiza fruit. Correspondingly, antioxidant activity assays showed a high antioxidant activity of both, O. macrorhiza fruit's peel and pulp. With regard to betacyanins, O. macrorhiza fruit's peel and pulp provide a deep red-purple color, whose average impact is higher compared to red beet (B. vulgaris spp.) and about 8-fold higher than red fruits from O. ficus-indica. Supporting these results, estimation of color attributes (L*, a*, b*, C and H°) showed also a high color impact of both O. macrorhiza fruit's peel and pulp.     

Quantification of the polyphenolic fraction and in vitro antioxidant and in vivo anti-hyperlipemic activities of Hibiscus sabdariffa aqueous extract

In the present study the quantification of the polyphenolic fraction, anthocyanins and other polar compounds, the antioxidant capacity and the anti-hyperlipemic action of the aqueous extract of Hibiscus sabdariffa has been achieved. Seventeen compounds were successfully quantified either by HPLC-DAD or HPLC-ESI-TOF-MS. Six of them were directly quantified by their corresponding standards, whereas the rest were indirectly quantified as equivalents using standards of similar compounds. The antioxidant capacity have also been estimated by comparing different assays, i,e, Trolox equivalent antioxidant capacity (TEAC), ferric reducing antioxidant power (FRAP), oxygen radical absorbance capacity (ORAC), and measurement of thiobarbituric acid reacting substances (TBARS). H. sabdariffa showed high reducing capacity in FRAP assay and significant capability to scavenge peroxyl radicals in the ORAC assay. Nevertheless, the extract exhibited poor efficacy to inhibit peroxyl radicals in lipid systems. The plant extract also exhibited the capacity to decrease serum triglyceride concentration on hyperlipemic mouse model.     

Polyphenols and triterpenes from Chaenomeles fruits: Chemical analysis and antioxidant activities assessment

Mugua, fruit of the genus Chaenomeles, is a valuable source of health food and Chinese medicine. To elucidate the bioactive compounds of five wild Chaenomeles species, extracts from fresh fruits were investigated by HPLC-DAD/ESI-MS/MS. Among the 24 polyphenol compounds obtained, 20 were flavan-3-ols (including catechin, epicatechin and procyanidin oligomers). The mean polymerisation degree (mDP) of procyanidins was examined by two acid-catalysed cleavage reactions; the mDP value was the highest in Chaenomeles sinensis and the lowest in Chaenomeles japonica. Total polyphenol content (TPC) reached 46.92 and 46.28 mg/g gallic acid equivalents (GAE) in Chaenomeles speciosa and Chaenomeles thibetica, respectively, although their main bioactive compounds were different (being epicatechin and procyanidin B2 in the former, and catechin and procyanidin B1 in the latter). These two species also exhibited equally strong free radical scavenging activities. Our results further showed that the antioxidant ability of Chaenomeles fruits was significantly correlated to their total polyphenol contents. Two triterpenes (oleanolic acid and ursolic acid) were the highest quantity in Chaenomeles cathayensis and C. thibetica, respectively.     

LC/ESI-MS/MS characterisation of procyanidins and propelargonidins responsible for the strong antioxidant activity of the edible halophyte Mesembryanthemum edule L.

Mesembryanthemum edule is used as a food ingredient and in traditional medicine. In this study, we investigated antioxidant activities of several extracts (methanol/acidified water, v/v: 20/80; 40/60 and 60/40) obtained from M. edule leaf, stem and root. Then, individual phenolics were characterised by reverse-phase HPLC coupled to electrospray ionisation mass spectrometry and multi-stage MS fragment analysis. Results showed that 40% methanol leaf extract, 40% methanol root extract and 20% methanol stem extract displayed the highest scavenging activity against DPPH and ABTS radicals. Regarding LC/ESI-MS/MS identification of active phenols, there were significant differences among the fractions of interest. In fact, 40% leaf extract mainly contained procyanidins, whereas propelargonidins were the major phenolics in 20% methanol stem extract, while, in 40% root extract, the active compounds remained unidentified. These results indicate that edible M. edule can be used as a nutraceutical in the pharmaceutical industry.     

Essential oil composition,antimicrobial and antioxidant properties of Mosla chinensis Maxim

The essential oil of Mosla chinensis Maxim was analysed by gas chromatography/mass spectrometry, and its main components are carvacrol (57.08%), p-cymene (13.61%), thymol acetate (12.68%), thymol (6.67%), and γ-terpinene (2.46%). The essential oil exhibited great potential antimicrobial activity against all eight bacterial and nine fungal strains. Antioxidant activity was also tested, the essential oil showing significantly higher antioxidant activity than that of the methanol extract. In addition, the amounts of total phenol components in the plant methanol extract (47.3 ± 0.4 μg/mg) and the oil (80.7 ± 0.5 μg/mg) were determined. The results presented here indicate that the essential oil of M. chinensis has antimicrobial and antioxidant properties, and is therefore a potential source of antimicrobial and antioxidant agents for the food and pharmaceutical industries.     

Structural characterisation of polysaccharides from Tricholoma matsutake and their antioxidant and antitumour activities

In this study, polysaccharides from Tricholoma matsutake (TM-P) were purified using a DEAE-Sepharose fast flow column and three polysaccharide fractions (TM-P1, TM-P2 and TM-P3) were obtained. The chemical composition and structural characteristics of TM-P2 were quite different from those of TM-P1 and TM-P3. TM-P2 consisted of glucose, galactose and mannose with a molar ratio of 5.9:1.1:1.0. The glycosidic linkages were mainly composed of 1,6- and 1-linked glucose. Furthermore, TM-P2 showed the strongest in vitro antioxidant and antitumour activities. The oxygen radical absorbance capacity (ORAC) of TM-P2 was 2100.44 μmol Trolox/g. The antiproliferative activities of TM-P2 (4.0 mg/ml) on the growth of HepG2 and A549 cells were 67.98% and 59.04%, respectively.     

Identification of antioxidant components and fatty acid profiles of the leaves and fruits from Averrhoa carambola

The antioxidant compounds of leaves and fruits from Averrhoa carambola were extracted with acetone:water (7:3, v/v) and distilled water. The acetone:water extracts (AWE) were separated into five different subfractions, three obtained by liquid–liquid extraction using n-hexane (HF), ethyl acetate (EAF) and water (WF), and the other two obtained by further fractionation of the WF on a Sephadex LH-20 column (WS1 and WS2). The antioxidant activities, total phenolics and total flavonoids of these extracts and fractions were investigated. Results showed that all the extracts and fractions possessed potent antioxidant activities, as measured by DPPH, ABTS and FRAP methods, with the strongest for WS2 fractions accompanied with the highest total phenolics and total flavonoids. Reversed-phase HPLC, normal-phase HPLC, MALDI-TOF-MS and ¹³C NMR analyses identified that the main antioxidant components present in WS2 fractions were essentially of procyanidin-type proanthocyanidins, consisting mainly of epicatechin units linked by B-type interflavan bonds. In addition, GC–MS analysis revealed that the most abundant fatty acids were α-linolenic acid (62.04 ± 1.65%) for leaves and oleic acid (55.44 ± 1.37%) for fruits. The amount of total unsaturated fatty acids in leaves and fruits comprised more than 77% of total fatty acid.     

Essential oil composition,antimicrobial and antioxidant activities of Satureja cuneifolia Ten.

Satureja cuneifolia Ten. is a well-known aromatic plant which is frequently used as a spice and herbal tea in Anatolia. S. cuneifolia oil was analyzed by gas chromatography/mass spectrometry (GC/MS). The major components of S. cuneifolia oil were carvacrol (44.99%) and p-cymene (21.61%). The essential oil of S. cuneifolia exhibited antimicrobial activity against all of the tested foodborne and spoilage bacteria. The minimum inhibitory concentration (MIC) values for test bacteria which were sensitive to the essential oil of S. cuneifolia were in the range of 600–1400 μg/ml. Antioxidant activities of the essential oil and the methanolic extract from S. cuneifolia were evaluated by using DPPH radical scavenging, β-carotene–linoleic acid bleaching and metal chelating activity assays. In addition, the amounts of total phenol components in the plant methanolic extract (222.5 ± 0.5 μg/mg) and the oil (185.5 ± 0.5 μg/mg) were determined.     

Phenolics, betacyanins and antioxidant activity in Opuntia joconostle fruits

Sour prickly pears (xoconostles) are fruits from Opuntia joconostle cactus, which are cultivated in the central Mexico area. Phenolic and pigment content in various parts of O. joconostle fruits were analyzed. The antioxidant activity of a methanolic extraction and different semi-purified fractions were also evaluated by the DPPH⁺ method. Xoconostle fruits were obtained from a commercial orchard in Mexico State. Fruits were analyzed as whole fruit and each fruit part including pericarp, mesocarp and endocarp. Samples were homogenized and kept at 4 °C until sample preparation. Total phenolic content and total flavonoid content varied among the different parts of the fruit. The highest amount of phenolic compounds and total flavonoids content were found in pericarp 2.07 mg gallic acid equivalents (GAE)/g fresh weight (FW) and 0.46 mg(+)-catechin equivalents (CE)/g FW respectively. Seven phenolics were identified as protocatechuic, 4-hydroxybenzoic, caffeic, vanillic and syringic acids, rutin, and quercetin. The color of the fruit parts was mainly due to the presence of betacyanins. The betacyanin concentration was higher in the endocarp (23.03 mg betanin equivalents/100 g fresh weight) than in the pericarp and mesocarp. Betacyanins were identified by HPLC-PDA-MS as betanin, isobetanin, betanidin, isobetanidin, and phyllocactin. Methanolic extracts and semi-purified fractions A (phenolics and flavonols) and B (betacyanins) of xoconostle showed high antioxidant activity mainly in the pericarp. These results suggest that xoconostle is a rich source of antioxidant compounds such as phenolic compounds and betacyanins.     

Hepatoprotective and antioxidant activity of ethanolic extracts of edible lotus (Nelumbo nucifera Gaertn.) leaves

Lotus (Nelumbo nucifera Gaertn.), an aquatic vegetable, is extensively cultivated in eastern Asia, particularly in China. An ethanolic extract of the leaves was studied for its hepatoprotective activity against CCl₄-induced liver toxicity in rats. In vitro and in vivo antioxidant activity was also assessed. The results showed the hepatoprotective activity of lotus leaf extract (LLE) at doses of 300 and 500 mg/kg and in vivo antioxidant activity at 100 mg/kg that was comparable with that of a standard treatment comprising 100 mg/kg of silymarin, a known hepatoprotective drug. These data were supplemented with histopathological studies of rat liver sections. The main flavonoids and phenolic compounds of LLE were analysed by HPLC-DAD-ESI/MS methods. Six of the compounds detected were tentatively characterised, one as catechin glycoside and five as flavonoid glycoside derivatives: miricitrin-3-O-glucoside, hyperin, isoquercitrin, quercetin-3-O-rhamnoside and astragalin.     

Soluble phenols and antioxidant activity in mamey sapote (Pouteria sapota) fruits in postharvest

Mamey sapote (Pouteria sapota (Jacq.) H. E. Moore & Stearn) is a tropical species from the Sapotaceae family native to Mexico and Central America. Its tree produces an edible climacteric fruit, whose weight can range from 250 to 900 g. The flesh is soft, comprises about 78% of the fruit, and has high sugars to acidity ratio, which gives it a sweet taste when ripe. Because of current public interest to consume products that promote health, the aim of the work was to characterize soluble phenolic content and antioxidant activity in mamey sapote fruits from Chiapas, Mexico, at different maturity stages. Storage at 12 (± 1) °C was conducted for 18 d. When fruits ripened firmness flesh varied, in average, from 41.8 to 3.0 N, soluble solids content from 17.7 to 28.1 ºBrix, hue angle from 56.4 to 46.3º, and lightness from 67.3 to 42.0. Phenolic content was affected by ripening since average values of 2563 and 234 ??g/g were found in unripe and consumption maturities, respectively. In a soluble phenolics extract from flesh, gallic acid (GA), gallocatechin-3-gallate (G3G), epicatechin (ECT), and catechin (C) were found, being the latter the most abundant compound, which increased with ripening from 9.9 to 113.1 ??g/g, while GA, G3G, and ECT had average values of 4.7, 11.9, and 5.8 ??g/g, respectively, without significant variation. Antioxidant activity, expressed through the IC₅₀ parameter, remained practically unchanged and showed an average value of 12.9 ??g/mL. Based on phenolic composition the mamey sapote fruit may constitute a good source of antioxidant compounds.     

Identification,quantification and antioxidant activity of acylated flavonol glycosides from sea buckthorn (Hippophae rhamnoides ssp. sinensis)

A novel acylated flavonol glycoside: isorhamnetin (3-O-[(6-O-E-sinapoyl)-β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl-7-O-α-l-rhamnopyranoside) (1), together with two known acylated flavonol glycosides: quercetin (3-O-[(6-O-E-sinapoyl)-β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl-7-O-α-l-rhamnopyranoside) (2) and kaempferol (3-O-[(6-O-E-sinapoyl)-β-d-glucopyranosyl-(1 → 2)]-β-d-glucopyranosyl-7-O-α-l-rhamnopyranoside) (3) were isolated from the n-butanol fraction of sea buckthorn (Hippophae rhamnoides ssp. sinensis) berries for the first time by chromatographic methods, and their structures were elucidated using UV, MS, ¹H and ¹³C NMR, and 2D NMR. Compounds 1–3 showed good scavenging activities, with respective IC₅₀ values of 8.91, 4.26 and 30.90 μM toward the 2,2′-diphenyl-1-picrylhydrazyl (DPPH) radical; respective Trolox equivalent antioxidant capacities of 2.89, 4.04 and 2.44 μM μM⁻¹ toward 2,2′-azino-bis-3-ethyl-benzothiazoline-6-sulphonate (ABTS) radical. The quantitative analysis of the isolated acylated flavonol glycosides was performed by HPLC–DAD method. The contents of compounds 1–3 were in the range of 12.2–31.4, 4.0–25.3, 7.5–59.7 mg/100 g dried berries and 9.1–34.5, 75.1–182.1, 29.2–113.4 mg/100 g dried leaves, respectively.     

Studies on the antioxidant potential of flavones of Allium vineale isolated from its water-soluble fraction

The aim of this work was to examine the chemical constituents and antioxidant potential of water-soluble fractions from the commonly consumed vegetable, Allium vineale. The water-soluble fraction, containing phenolic compounds, was extracted with ethyl acetate to obtain flavonoids which were separated and purified by repeated column chromatography over Sephadex LH-20, RP C18 and silica gel. The isolated compounds were identified according to their physicochemical properties and spectral data (UV, HPLC–TOF/MS, ¹H NMR, ¹³C NMR and 2D NMR). Three flavonoids were isolated and identified as chrysoeriol-7-O-[2″-O-E-feruloyl]-β-d-glucoside (1), chrysoeriol (2), and isorhamnetin-3-β-d-glucoside (3). Antioxidant studies of the aqueous extract and three isolated compounds, 1, 2, 3, were undertaken and they were found to have significant antioxidant activity. Antioxidant activities were evaluated for total antioxidant activity by the ferric thiocyanate method, ferric ion (Fe³⁺) reducing antioxidant power assay (FRAP), ferrous ion (Fe²⁺) metal chelating activity, and DPPH free radical-scavenging activity. The water-soluble ethyl acetate and methanol extraction methods were also compared using HPLC–TOF/MS.     

Phenolic acid analysis and antioxidant activity assessment of oil palm (E. guineensis) fruit extracts

Phenolic compounds in oil palm fruit (E. guineensis) were extracted in soluble free (SFP), insoluble-bound (ISBP) and esterified (EFP) forms. The total phenolic content (TPC) of the oil palm fruit extracts was determined using the Folin–Ciocalteu method and found to range from 5.03 to 9.04 g/L per g of dried weight (DW). The antioxidant activities of oil palm phenolic extracts were analysed using free radical scavenging assays and results showed that oil palm phenolic extracts contained antioxidant activities in the order of ISBP > EFP > SFP. Eight different phenolic acids were identified and quantified using a simple reversed-phase high performance liquid chromatography (HPLC) with a diode array detector (DAD) and liquid chromatography/tandem mass spectrometry (LC/MS/MS). Ferulic, p-hydroxybenzoic and p-coumaric acid were the dominant phenolic acids found in oil palm fruit extracts and ranged from 55 to 376 μg/g of DW.     

Major anthocyanins and antioxidant activity of Nasturtium flowers (Tropaeolum majus)

Major anthocyanins, ascorbic acid content, total phenolic content, and the radical scavenging activity against ABTS and DPPH radicals in petals of orange Nasturtium flowers (Tropaeolum majus), were investigated. Anthocyanin (ACN) content in the petals was 72 mg/100 g FW and pelargonidin 3-sophoroside represented 91% of the total ACN content. The ascorbic acid content was 71.5 mg/100 g and the total phenolic content as determined by the Folin–Ciocalteau method was 406 mg GAE/100 g FW. The radical scavenging activities against ABTS and DPPH radicals were 458 and 91.87 μm trolox eq/g FW, respectively. The excellent free radical scavenging activities along with high phenolic and ascorbic acid content of Nasturtium flowers suggest that they could be source of natural pigments and antioxidants for applications in functional foods.     

Isolation,identification, and antioxidant activity of anthocyanin compounds in Camarosa strawberry

This paper explores the bioactive composition of strawberry (Camarosa variety) [Fragaria × ananassa (Rosaceae Family)] describing its anthocyanin composition and measuring the antioxidant activity (AA) of isolated pigments.