Isolation, structure elucidation and antioxidant potential of the major phenolic and flavonoid compounds in brined olive drupes (original) (raw)
Journal of Agricultural and Food Chemistry, 2006
Carotenoid metabolites are common plant constituents with significant importance for the flavor and aroma of fruits. Three new carotenoid derivatives, (2E,4E)-8-hydroxy-2,7-dimethyl-2,4-decadiene-1,10-dioic acid 1-O-D-glucopyranosyl ester (1), (2Z,4E)-8-D-glucopyranosyloxy-2,7-dimethyl-2,4decadiene-1,10-dioic acid (3), and 3,9-dihydroxymegastigmast-5-ene-3-O-[-D-glucopyranosyl-(1f6)]-D-glucopyranoside (5), as well as three known compounds, have been isolated from the ethanolic extract of peels of Cydonia vulgaris, the fruit of a shrub belonging to the same family as the apple. All the compounds were identified by spectroscopic techniques, especially 1D and 2D NMR. Antioxidant activities of all the isolated metabolites were assessed by measuring their ability to scavenge DPPH radical and superoxide radical (O 2 •-) and to induce the reduction of Mo(VI).
Isolation and Structure Elucidation of Antioxidant Polyphenols from Quince (Cydonia vulgaris) Peels
Journal of Agricultural and Food Chemistry, 2008
Thirteen new compounds, as well as 16 already known, have been isolated from organic extracts of peels of Cydonia vulgaris, a fruit of a shrub belonging to the same tribe as the apple. All of the structures were elucidated by EI-or ESI-MS and 1 H and 13 C NMR after purification of individual compounds by HPLC. Thirteen fatty acid esters of cinnamyl alcohols, three fatty acid esters of hydroxybenzoic acid, three fatty acid esters of hydroxybenzaldehyde, three glucosides of aromatic acids, four chlorogenic acids, two flavonols, and a benzylamine have been identified. The fatty acid moieties have been identified by GC-MS analysis of the methanolysis products. All of the compounds were tested for their radical scavenging and antioxidant activities by measuring their capacity to scavenge the 2,2′-diphenyl-1-picrylhydrazyl (DPPH) radical and anion superoxide radical and to induce the reduction of Mo(VI) to Mo(V). The chlorogenic acids and the flavonols exhibited more antioxidant and radical scavenger capacity than the positive standards R-tocopherol and ascorbic acid. The results of the tests were analyzed by cluster analysis that grouped all of the compounds on the basis of the substituents on the aromatic ring.
Journal of Agricultural and Food Chemistry, 2005
Increasing interest in phenolic compounds in olives is due to their antioxidant and health-enhancing properties. In this study the phenolics in fruits of the Tunisian olive cultivar Chemlali were extracted by methanol-water and fractionated using Sephadex LH-20 column chromatography. The identification of phenolic monomers and flavonoids was based on separation by high-performance liquid chromatography equipped with a diode array detector followed by liquid chromatography-mass spectrometry and gas chromatography-mass spectrometry analysis. Oleuropein, a secoiridoid glycoside esterified with a phenolic acid, was the major compound. Eight phenolic monomers and 12 flavonoids were also identified in Chemlali olives. Five flavonoids were isolated and purified using Sephadex LH-20 column chromatography and preparative paper chromatography. The antioxidant activity of the extract and the purified compounds was evaluated by measuring the radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl and by using the-carotene-linoleate model assay. Acid hydrolysis of the extract enhanced its antioxidant activity. Hydroxytyrosol and quercetin showed antioxidant activities similar to that of 2,6-di-tert-butyl-4-methylphenol. A hydroxyl group at the ortho position at 3′ on the B ring of the flavonoid nucleus could contribute to the antioxidant activity of the flavonoids.
Phenolic Compounds in Olive Leaf Extract as a Source of Useful Antioxidants
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Using electron paramagnetic resonance (EPR) spectroscopy, antioxidant properties of olive leaves extracts obtained of three autochthonous olive varieties grown in Istria, Buža, Istarska bjelica and Rosinjola have been investigated. The highest content of total phenolic compounds ((57.6 ± 0.1) mg quercetin equivalents/g of dry extract) was obtained for extract of Buža. The analysis of chemical composition of extracts was performed by HPLC/DAD and LC/MS method. Futhermore, Buža has shown the highest antioxidant activity in scavenging DPPH radical (AA=80.0 ± 3.0%), followed by extracts of Rosinjola and Istarska bjelica. In DPPH radical scavenging assay fi nal concentration of extracts in was 0.1 mg/mL. Antioxidant activity was in good correlation with total phenolics. It seems that these bioproducts could be useful in therapy of conditions related with oxidative stress. The results have indicated a high potential of application of olive leaf and olive leaf extract in foodstuff and food additive. Also, it can be used to improve the shelf life of foods and to develop functional foods.
Antioxidant activity of polyphenols from solid olive residues of c.v. Coratina
Fitoterapia, 2006
The antioxidant profile of extracts from solid olive residue (SOR) of c.v. Coratina, a cultivar widely diffused in the south of Italy, using both cell-free and cell-based experimental models, was investigated. A total hydroalcoholic extract (polyphenols content 19.7%) and a purified extract (Oleaselect™) (polyphenols content 35.1%) were tested for their ability to quench the stable free radical DPPH, the peroxyl radicals (ORAC assay), by monitoring the loss in fluorescence of R-phycoerythrin induced by the peroxyl radical generator AAPH and their ability to inhibit the cumene hydroperoxide-induced lysis of rat red blood cells (RBC).
Acta Horticulturae, 2011
Ten Greek olive cultivars, 'Koroneiki', 'Lianolia Kerkyras', 'Mastoidis', 'Arbequina', 'Adramytini', 'Megaritiki', 'Gaidourelia', 'Kalamon', 'Konservolia' and 'Chalkidiki', were studied in order to determine the phenolic profile, the phenolic content, and the antioxidant activity, both in leaves and drupes (green and black) in each cultivar. Total phenolic content, in new season leaves, ranged between 1.01 mg GAE/g ('Adramytini') and 2.06 mg GAE/g ('Konservolia'), while the antioxidant activity ranged between 157.64 ppm ('Konservolia') and 285.80 ppm ('Adramytini'). In green drupes, total phenolic content ranged between 0.59 mg GAE/g ('Megaritiki') and 1.98 mg GAE/g ('Mastoidis') while the antioxidant activity ranged between 119.66 ppm ('Lianolia Kerkyras') and 496.45 ppm ('Megaritiki'). Total phenolic content in black drupes ranged between 0.54 mg GAE/g ('Gaidourelia') and 0.99 mg GAE/g ('Lianolia Kerkyras'), while the antioxidant activity ranged between 284.23 ppm ('Lianolia Kerkyras') and 886.36 ppm ('Chalkidiki'). The HPLC analysis showed the presence of flavonoids, hydroxycinnamic derivatives and secoiridoids. In leaves the most abundant compounds were oleuropein, luteolin-7-o-glucoside and rutin while luteolin-4-o-glucoside, hydroxytyrosol and caffeic acid were detected in lower amounts. In drupes the most abundant compounds were verbascoside and oleuropein.
Composition and Antioxidant Activity of Olive Leaf Extracts from Greek Olive Cultivars
Journal of the American Oil Chemists' Society, 2010
The olive leaf phenolic composition of the Greek cultivars koroneiki, megaritiki and kalamon was determined using LC/MS. Furthermore, the antioxidant activity of olive leaf extracts from the above three cultivars, using solvents of increasing polarity (petroleum ether, dichloromethane, methanol and methanol/water: 60/40) was evaluated using the stable free radical diphenylpicrylhydrazyl (DPPH) test. Furthermore the oxidative stability index (OSI) was compared to that of the synthetic antioxidant TBHQ and commercial oleoresin (rosemary extract). The ability of phenolic compounds to inhibit the lipoxygenase (LOX) activity was also investigated. The ten main components determined in the olive tree leaf extracts for the cultivars koroneiki and kalamon were: secologanoside, dimethyloleuropein, oleuropein diglucoside, luteolin-7-O-glucoside, rutin, oleuropein, oleuroside, quercetin, ligstroside and verbascoside. Respective compounds for the cultivar megaritiki were: secologanoside, dimethyloleuropein, oleuropein diglucoside, luteolin7-O-glucoside, oleuropein, oleuroside, quercetin and ligstroside. In all three cultivars, oleuropein represented the main phenolic component. The solvent polarity influenced the total amount of the phenolic compounds determined. When methanol/water (60/40) was used, as solvent, more phenolic compounds were determined. The total amounts of phenols determined in the extracts, obtained by successive extractions using the above solvents, were 6,094, 5,579 and 6,196 mg/kg (mg gallic acid/kg dried olive leaves) for the cultivars megaritiki, kalamon and koroneiki, respectively. Among all extracts, methanol/water extracts exhibited the highest antioxidant activity as shown through the application of the DPPH and OSI methods. The OSI antioxidant activity followed the sequence: synthetic antioxidant TBHQ [ commercial oleoresin [ olive tree leaf extracts [ control. Likewise, methanol/water olive leaf extracts significantly inhibited soybean lipoxygenase, although some small differences in the activity among the olive leaf extracts of the different cultivars were observed. The solvent polarity as well as the amount of the extract influenced the inhibitory activity. A positive correlation was shown between the antioxidant activity of leaf extracts and the total phenol content.
Classification, Biotransformation and Antioxidant Activity of Olive Fruit Biophenols: A Review
Current Bioactive Compounds, 2012
Olive biophenols affect the organoleptic and nutraceutical properties of fruits; therefore, it is an emerging research field. In addition, a plethora of health-promoting properties have been attributed to the phenolic content of olive fruits. The main biophenols can be divided into different sub-groups such as phenolic acids and alcohols, flavonoids, lignans and secoiridoids. The latter sub-group of biophenols is typical in olive fruits, since oleuropein and the products of its biotransformation characterize olive fruit. An array of genetic, agronomic and technological factors that affect the rate of synthesis and biotransformation of secoiridoids in olive fruits is discussed. Furthermore, the relationship between antioxidant activity and structures of olive biophenols is explored.
Antioxidant activities and phenolic composition of Olive (Olea europaea) leaves
The present study compares the antioxidant activities of leaves of eight cultivars of olive. The aqueous extracts of leaves showed inhibition against thiobarbituric acid reactive species (TBARS) induced by pro-oxidant (10 μM FeSO 4) in mice liver. The order of the antioxidant activity among cultivars on lipid peroxidation assay is Gemlik > Frantio > Doleca-Agogia > Moriolo > Mission > Uslu > Leccino > Carotina. Different varieties of olive showed good antioxidant properties, IC 50 values ranged between 22.46 to 198 μg/ml on 2,2-diphenyl-1-picrylhydrazyl (DPPH) assay. The major phenolic acids, some flavonoid aglycone and glycosides were identified in leaves by high performance liquid chromatography. Ellagic acid (29.80 ± 0.02 mg/g), caffeic acid (15.73 ± 0.01mg/g), gallic acid (15.69 ± 0.01 mg/g), rutin (34.56 ± 0.03 mg/g), quercetin (16.41 ± 0.01 mg/g), epicatechin (11.04 ± 0.01 mg/g) and quercitrin (15.32 ± 0.03 mg/g) were predominant in infusion of olive.
Journal of Agricultural and Food Chemistry, 2010
The contribution of flavonoids to the overall radical scavenging activity of olive leaf polar extracts, known to be good sources of oleuropein related compounds, was examined. Off line and on line HPLC-DPPH • assays were employed, whereas flavonoid content was estimated colorimetrically. Individual flavonoid composition was first assessed by RP-HPLC coupled with diode array and fluorescence detectors and verified by LC-MS detection system. Olive leaf was found a robust source of flavonoids regardless sampling parameters (olive cultivar, leaf age or sampling date). Total flavonoids accounted for the 13-27% of the total radical scavenging activity assessed using the on line protocol. Luteolin 7-O-glucoside was one of the dominant scavengers (8-25%). Taking into consideration frequency of appearance the contribution of luteolin (3-13%) was considered important, too. Our findings support that olive leaf, except for oleuropein and related compounds, is also a stable source of bioactive flavonoids.
GIDA - Journal of Food, 2012
White-flesh guava is widely planted in tropical or subtropical areas of Southeast Asia. Despite of folk statements on specific function, few researches are focused on the description of its plant secondary metabolites. In the present work, contents of total phenolics and flavonoids as well as antioxidant activity from different parts (peel, flesh and seed) were determined. The constituents of ethanol extracts were characterized by HPLC-QTOF-MS. A total of 69 phenolic compounds as well as 9 polar compounds were detected, with flavonoids, hydrolyzable tannins, phenolic acid derivatives and benzophenones of the four predominant phenolic compounds. Moreover, the presence of other phenolics (lignan, phenylethanoid, stilbenoid and dihydrochalcones) were revealed. Simultaneously, the polar compounds, such as triterpenoids, iridoid were identified. Benzophenones and triterpenoids were proved to be marked constitutes of peel and flesh respectively. The existence of isoflavonoids, lignan, phenylethanoid were firstly reported for
Journal of Food Science and Technology, 2018
The leaves of seventeen cultivars of olive growing in the north of Iran were investigated for total phenol content and antioxidant activity. The identification and quantification of main phenolic compounds were performed by reverse phase high performance liquid chromatography with diode array detector. The cultivars Kalamon, Gordal, and Coratina contained the highest concentration of phenolic compounds (190.65 ± 0.03, 184.72 ± 0.001, and 155.91 ± 0.06 mg GAE/g extract, respectively). The maximum radical scavenging activities were found in Gordal, Coratina, and Kalamon extracts (IC 50 20.66, 22.95, and 26.74 lg ml-1 , respectively). The extracts of Mishen, Fishomi, and Arbequina (1971.37 ± 0.007, 1794.57 ± 0.001, and 1760.57 ± 0.005 lmol Fe II/g dried extract, respectively) showed highest antioxidant activity in FRAP assay. The identification analysis demonstrated the present of vanillin, rutin, luteolin 7-O-glucoside, oleuropein, and quercetin. The highest oleuropein concentrations were detected in cultivars Mishen, Beleidi, Kalamon, and Roghani while it was not detected in cultivars Conservolea, Amigdalolia, Leccino, and Fishomi.
Journal of Agricultural and Food Chemistry, 2001
The isolation of nine triterpenoid saponins (1-9), among them six new natural compounds (1-6), from the MeOH extract of the fruits of Cyclanthera pedata is reported. All of the structures were elucidated by spectroscopic methods, including the concerted application of one-dimensional 1 H-1 H total correlation spectroscopy, 1 H-1 H nuclear Overhauser effect spectroscopy), and 13 C-13 C DEPT-NMR and two-dimensional NMR techniques (double-quantum filtered correlated spectroscopy, rotating-frame Overhauser enhancement spectroscopy, heteronuclear single quantum coherence, and heteronuclear multiple bond correlation). A comparative study of seeds and fruits has been also carried out.
Molecules
The phenolic compound contents and antioxidant activities of the leaf extracts of nine olive genotypes were determined, and the obtained data were analysed using chemometric techniques. In the crude extracts, 12 compounds belonging to the secoiridoids, phenylethanoids, and flavonoids were identified. Oleuropein was the primary component for all genotypes, exhibiting a content of 21.0 to 98.0 mg/g extract. Hydroxytyrosol, verbascoside, luteolin 7-O-glucoside, and luteolin 4′-O-glucoside were also present in noticeable quantities. Genotypes differed to the greatest extent in the content of verbascoside (0.45–21.07 mg/g extract). The content of hydroxytyrosol ranged from 1.33 to 4.03 mg/g extract, and the aforementioned luteolin glucosides were present at 1.58–8.67 mg/g extract. The total phenolic content (TPC), DPPH• and ABTS•+ scavenging activities, ferric reducing antioxidant power (FRAP), and ability to inhibit the oxidation of -carotene-linoleic acid emulsion also varied significa...
Journal of food science and technology, 2018
The leaves of seventeen cultivars of olive growing in the north of Iran were investigated for total phenol content and antioxidant activity. The identification and quantification of main phenolic compounds were performed by reverse phase high performance liquid chromatography with diode array detector. The cultivars Kalamon, Gordal, and Coratina contained the highest concentration of phenolic compounds (190.65 ± 0.03, 184.72 ± 0.001, and 155.91 ± 0.06 mg GAE/g extract, respectively). The maximum radical scavenging activities were found in Gordal, Coratina, and Kalamon extracts (IC 20.66, 22.95, and 26.74 µg ml, respectively). The extracts of Mishen, Fishomi, and Arbequina (1971.37 ± 0.007, 1794.57 ± 0.001, and 1760.57 ± 0.005 µmol Fe II/g dried extract, respectively) showed highest antioxidant activity in FRAP assay. The identification analysis demonstrated the present of vanillin, rutin, luteolin 7-O-glucoside, oleuropein, and quercetin. The highest oleuropein concentrations were d...
Determination and Identification of The Biologically Active Compounds in Olive Leaves
Scientific Journal of Agricultural Sciences, 2024
Olive leaf extract (OLE) is one of the natural extracts utilized to obtain bioactive components. It contains the potential sources of several phenolic compounds. The total flavonoid concentration, total phenolic content, antioxidant activity, and drying procedures of OLE, air-dried (AD), freeze-dried (FD), and fresh extract (FE) were evaluated via HPLC. LC-MS/MS characterization and identification were subsequently conducted to obtain additional structural information on the separated compounds. The extract obtained using ethanol (80%) had a high total phenolic content (114.55 FD, 91.95 AD, and 63.41 mg FE/g dw) and TFC (251.25 FD, 254.43 AD, and 111.67 mg FE/g dw). Additionally, the DPPH technique was used to assess the antioxidant activity of OLE (82.43 FD, 89.53 AD, and 64.13 mg FE/g dw). HPLC was used to characterize and identify 21 bioactive compounds. Phenolic compounds such as Oleuropein, Apigenin-7-O-glucoside, Luteolin-7-Oglucoside, Luteolin, Quercetin, Homo vanillic acid, Apigenin, Hydroxytyrosol, Caffeic acid, Tyrosol, and Vanillin were identified via the LC-MS/MS profile of OLE. The results of this study indicate that the bioactive components obtained from olive leaf extract are valuable sources of antioxidants, which may lead to applications in the pharmaceutical and food industries.
Horticulturae
Olive leaves are rich in phenolic compounds, which give them antioxidant properties that are associated with a lower incidence of disease. Therefore, the aim of this work was to determine the phenolic content, antioxidant activity, and toxicity of the aqueous extracts of olive leaves of the main Spanish and Greek cultivated and wild genotypes. For these purposes, ‘Picual’ and ‘Arbequina’ leaves from Spain and ‘Koronoeiki’ and ‘Kalamon’ leaves from Greece were collected, as were wild olive leaves from both countries. The aqueous extracts of these genotypes were analyzed by HPLC-DAD, and the DPPH·, ABTS·+ Folin–Ciocalteu, and Microtox® methods were also used. ‘Picual’ had the highest oleuropein values, followed by wild olive leaves from both countries and ‘Arbequina’. The latter was reflected in the antioxidant activity measured by DPPH· and ABTS·+, which positioned the leaves of ‘Arbequina’, ‘Picual’, and the wild genotypes as having the most antioxidant activity. As expected, these ...
In vitro antioxidant activity of hydroalcoholic extract of Cyamopsis tetragonolobus
2011
An antioxidant is a molecule capable of slowing or preventing the oxidation of other molecules. The most common reactive oxygen species (ROS) include superoxide (O 2− ) anion, hydrogen peroxide (H 2 O 2 ), peroxyl (ROO − ) radicals, and reactive hydroxyl (OH − ) radicals. The nitrogen-derived free radicals are nitric oxide (NO) and peroxynitrite anion (ONOO). Under normal state of affairs, the ROS generated are detoxified by the antioxidants nearby in the body and there is symmetry between the ROS generated and the antioxidant present. However, due to ROS over production and/or derisory antioxidant argument, this equilibrium is hindered favoring the ROS gain that culminates in oxidative hassle. The ROS readily attack and induce oxidative damage to various biomolecules including proteins, lipids, lipoproteins and DNA. This oxidative damage is decisive etiological factor concerned in quite a lot of chronic human diseases such as diabetes mellitus, cancer, atherosclerosis, arthritis, and neurodegenerative diseases and also in the ageing course. Based on growing interest in free radical biology and the lack of effective therapies for most chronic diseases, the expediency of antioxidants in protection against these diseases is defensible. Epidemiological studies have shown that the intake of antioxidants such as vitamin C reduces the risk of
Chemical research in …, 2008
The major biophenols in olives and the crude extract and ethyl acetate fraction from olive mill waste were studied for their ability to counteract different stages of oxidative damage, that is, hydrogen peroxide, superoxide radical (SOR), and hydroxyl radical in vitro. Antiproliferative activity on colon cancer (HT-29) and gastric cancer (AGS) cell lines was measured by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide bioassay. Emphasis was given to how the observed in vitro activity is controlled by the structural feature of biophenols and possible synergism and antagonism. While in some bioassays, for example, 2,2′-diphenyl-1-picrylhydrazyl, the nonphenolic moiety had minimal affect, it had a significant role in the SOR scavenging bioassay. Verbascoside was more active than caffeic acid or hydroxytyrosol evaluated individually or in equimolar mixtures in some bioassays. Mixtures of biophenols were more active than individual biophenols as antiproliferative agents. Overall, the mixture of hydroxytyrosol/ caffeic acid and the biophenol extracts were more effective in protecting DNA from oxidative damage and inhibiting the growth of cancer cells.