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Phenolic Profile Characterization of Chemlali Olive Stones by Liquid Chromatography-Ion Trap Mass Spectrometry
Abstract
Aqueous methanol extracts of Chemlali olive stones were analyzed by reverse phase high-performance liquid chromatography (HPLC) with diode array detection and mass spectrometry [LC-MS/MS]. Oleoside, oleoside 11-methyl ester, nuezhenide, oleoside 11-methyloleoside, nuezhenide 11-methyloleoside, oleuropein and glycosides of tryosol and hydroxytyrosol glycosides were identified in stones of Chemali olives. The antioxidant activity observed for the extract of the olive stones (IC50= 13.84 µg/ml, TEAC= 0.436 mM) may be due to the high content of phenolic compounds of which the main compounds are nuezhenide (325.78 mg/100g), methoxy derivative of nuezhenide (132.46 mg/100g) and nuzhenide-11-methyloleoside (82.91 mg/100g). These results suggest the use of olive stones as sources of natural antioxidants.
... The phenolic profile of olive seed has been the central point of interest in few studies. Nevertheless, some phenolic compounds such as alidroside, nuezhenide, hydroxytyrosol, nuezhenide 11-methyl oleoside, oleuropein, tyrosol, and demethyloleuropein were identified (Mansour et al., 2015b;Silva et al., 2010). Mansour et al. (2015b) studied the phenolic composition of olive stones obtained from the Chemlali cultivar. ...
... Nevertheless, some phenolic compounds such as alidroside, nuezhenide, hydroxytyrosol, nuezhenide 11-methyl oleoside, oleuropein, tyrosol, and demethyloleuropein were identified (Mansour et al., 2015b;Silva et al., 2010). Mansour et al. (2015b) studied the phenolic composition of olive stones obtained from the Chemlali cultivar. Nuezhenide was present in a higher concentration, followed by a methoxy derivative of nuezhenide and nuezhenide-11methyloleoside. ...
... Nuezhenide was present in a higher concentration, followed by a methoxy derivative of nuezhenide and nuezhenide-11methyloleoside. Other minor phenolic compounds were detected as hydroxytyrosol, tyrosol, and oleuropein (Mansour et al., 2015b). The fatty acid content and squalene of virgin oils produced with different parts of olive fruit (pulp, seeds, and whole fruits) of Chemlali and Oueslati olive varieties were also studied. ...
This comprehensive review points out the major developments on the recovery of bioactive compounds of olive by-products, intending innovative food applications and enhanced technological functions. Nutritional and sensorial factors influencing consumers' acceptance are also discussed. Besides being an economic burden for producers, olive oil by-products also represent a severe environmental problem. Simultaneously, these are rich in bioactive compounds, which are remarkable added-value ingredients for other industries. New applications have been focused in ameliorating the food nutritional profile, replacing or improving technological properties/functions of food additives, and extending food products shelf life. Eco-friendly food packaging is also a promissory application field. The improvement of nutritional functionality and sensory quality of enriched food is another challenging task. Despite the large chemical characterization of olive products and olive oil processing by-products, further research is still needed to fully understand the potential of this valuable raw material.
... Oleoside and a di glucoside of tyrosol were first reported in olive stone which may need confirmation in other cvs. or tree origins (Ben Mansour, et al., 2015). To provide a comprehensive metabolite profile in different olive matrices, a multiplex approach (LC-ESI/APCI-MS and GC/MS) was used for profiling 6 olive samples (olive leaf, seed, skin, pulp, and stem, in addition to virgin olive oil) derived from Picudo cv. in Spain. ...
... The major phenolics portion in olive fruit is typically not extracted during olive oil production and rather remains in its wastewater, pomace or seed (Borja, Alba, & Banks, 1997), as 1 L of crude OMWW provides 1 g of pure hydroxytyrosol (Allouche, Fki, & Sayadi, 2004). LC− MS analysis of O. europea Chemlali stone revealed the presence of 2-(dihydroxyphenyl) ethanol-O-hexoside, 2-(hydroxyphenyl) ethanol di-O-hexoside, 2 (hydroxyphenyl) ethanol-O-hexoside, oleoside, oleoside 11-methyl ester, alongside with oleuropein to account for several of its health benefits (Ben Mansour, et al., 2015). Less attention towards profiling OMWW has been made in literature compared to seed or pomace warranting for more future studies especially considering its large volume in oil production. ...
... In Tunisia, the oleoculture depends principally on two varieties: Chetoui and Chemlali [10]. In addition, there are also other secondary local varieties specific to minor regions such as "Sayali" in the northern regions, "Oueslati" in Kairouan, "Zalmati", and "Zarrazi" in Zarzis [8]. ...
... In Tunisia, olive orchards are characterized by the cultivar population Chemlali planted in the north, the Sahel, the centre and the south covering approximately 80% of the Tunisian olive grove [10]. Similarly, Chemlali cultivar endures an important lack of rainfall unhelpful for growth and reproductive expansion in cultivated dry areas [16]. ...
Olive oil composition and connection between effective physicochemical factors characterizing accessions from different Tunisian farming sites viz. Chemlali Sfax, Chemalali Medenine, and Zalmati Medenine, located in the centre and the south of Tunisia, was probed in this study. The relationship between olive oil composition and physicochemical characteristics from different Tunisian cultivars, namely, Chemlali Sfax, Chemlali Medenine, and Zalmati Medenine, located in the centre and the south of Tunisia, was investigated using multivariate statistical analysis. Multiple linear regressions (MLR) and artificial neural network (ANN) methodologies were employed to expose hidden relationships between oxidative stability and olive oil components such as fatty acids, phenolic acids, and sterol contents. Obtained results showed not only that the selected components are dependent on geographical location and varietal origin of olive oils, but also that fatty acids (C16:1, C17:1, C18:0, C18:1, and C18:2), specific phenols (p-hydroxyphenylacetic, o-coumaric, and gallic acids), and sterols (campestanol, stigmasterol, and sitostanol) are directly implied in the oxidative stability variation. However, ANN analysis allowed to obtain more accurate models with higher robustness (R²> 98%). The combined analytical approaches, MLR and ANNs, could be considered as an adequate experimental model to restrain the influence of olive oil components in characterization of olive oil quality. Here, we have addressed the aim of using different analytical instruments in this field and the application of chemometrics for sterols, phenolic acids, and fatty acid analysis.
... 51 Our results revealed only slight differences in quality parameter values of VOOs from different regions, in agreement with previous studies including VOO of Chemlali variety. 28,52,53 Polyphenols and pigment contents The content of phenolic compounds in VOO is an important factor when evaluating its quality, given that the natural phenols improve its resistance to oxidation and preserve VOO quality during storage. As shown in Table 3, the average levels of polyphenols in the Chemlali VOOs studied ranged between 120 and 360 mg/kg, consistent with the results of Ben Hlima et al. 25 In agreement with other studies, 12,14,28 a relationship was found between the geographical area of production of VOOs and their total phenol content (P < 0.001) ( Table 3). ...
Background:
despite their high potential, Tunisian virgin olive oils (VOOs) are mainly exported in bulk or blended with VOOs of other origin, hindering their international market placement. To face this situation, their valorization is needed by highlighting their unique features and by developing tools to guarantee their geographical authenticity. Compositional features of Chemlali VOOs produced in three Tunisian regions were assessed to identify suitable authenticity markers.
Results:
quality indices ensured the quality of the VOOs studied. Volatile compounds, total phenols, fatty acid (FA) and chlorophylls resulted significantly influenced by the region of origin, which was justified by the differences found in soil and climatic conditions of the three geographical regions. To explore the capabilities of these markers for the geographical authentication of Tunisian Chemlai VOOs, classification models based on partial least square-discriminant analysis (PLS-DA) were developed by grouping the minimum number of variables allowing the highest discrimination power, minimizing in this way the analytical procedure. The PLS-DA authentication model based on combining volatile compounds with FA or with total phenols achieved a correct classification of 95.7%of the VOOs according to their origin, as assessed by 10%-out cross-validation.Sidi Bouzid Chemlali VOOs achieved 100% of correct classification, while the misclassification between Sfax and Enfidha ones did not exceed 10%.
Conclusions:
these results allowed to establish the most promising and affordable combination of markers for the geographical authentication of Tunisian Chemlali VOOs from distinct production regions and provide the basis for further develop authentication models based on wider datasets. This article is protected by copyright. All rights reserved.
... The olive tree (Olea europaea and Oleaceae) is within the oldest and most widespread fruit bearing tree species grown in the Mediterranean basin (Ben Mansour et al., 2015).The main producers of olives are still the Mediterranean countries, led by Spain, Italy and Greece. As a result, the European Union (EU) is responsible for 70% of global olive production, generating a production value of 7,000 million Euros each year, becoming a key factor for the development of the agro-industrial sector and, consequently, a social and economic driver for the southern regions of the European Union (Rossi, 2017). ...
In this study, the physicochemical properties and bioactive compounds of olive oils from
cultivars koroneikiand “coratina, grown in Khatatba, Sadat city, Minufiya Governorate,
Egypt, have been evaluated. Polyphenols are a large family of compounds found in fruits
and vegetables, which exhibit strong antioxidant activity by scavenging different families
of Reactive Oxygen Species (ROS). Polyphenols and secoiridoids found in EVOO,
including oleocanthal (180.00 and 171.00 mg/kg), hydroxythyrosol (3.53 and 9.46 mg/ kg)
and oleuropein aglycone (OLE) (575.76 and 664.91 mg/kg), in both Koroneiki and
Coratina olive oils, respectively. In all oil samples analyzed the highest antioxidant
capacity was attributed tokoroneiki olive oil (35.85% I of DPPH and 4.37% I of ABTS)
compared tocoratina, (26.37% I of DPPH and 2.82% I of ABTS). The main characteristics
of the koroneiki cultivar were a very high concentration of total phenols (530.00 mg/kg of
gallic acid) and α-tocopherol (155.00 mg/kg).
... Dissimilarities can also be ascribed to the source of the matrix, the TPC extraction procedure, and the collection season [58], as well as to geographic origin or climatic factors. About Chemlale, a famous cultivated variety in the Mediterranean region for the quality of its oil, previous works have been done even on the olive stones [53,63] which confirmed our results concerning the highest polyphenol content and antioxidant activity of this cultivar. Regarding the never previously studied varieties Atefah and Azeboudj, which is an oleaster, we found that they have a great antioxidant power. ...
The recovery of food waste is a stimulating opportunity for and competitive development of agroindustries. In this context, the objective of this study was to report the antioxidant potential and phenolic compounds content of olive stones (OS) of six Algerian cultivars. Two extraction methods were used: microwave assisted extraction (MAE) and conventional solvent extraction (CSE) in order to improve the recovery of total phenolic content (TPC) and the maximization of the two extraction processes by the Box-Behnken design (BBD) from olive stone of Olea Europaea L. cv Ayemele. The optimal processing parameters obtained were (i) for MAE: 22% (v/v) ethanol, 40 s, 500 W, and ratio 65:1 (mL/g) and (ii) for CSE: 33% (v/v) ethanol, 24 min, 71 °C, and ratio 60:1 (mL/g). Phenolic compounds were then extracted from olive stones of six Algerian cultivars with MAE best extraction conditions, as it was the best strategy in term of TPC recovery. The phenolic content was different according to the olive variety. The stones of Chemlale were the richest in TPC (7.23 mg GAE/g) followed by Azeboudj (6.33 mg GAE/g), Atefah (6.04 mg GAE/g), Agraraz (5.63 mg GAE/g), Azeradj (5.35 mg GAE/g) and Ayemel (5.14 mg GAE/g). A similar profile was observed with total flavonoids content and antioxidant activities. The anti-inflammatory effects of the optimized extracts by MAE were assessed regarding their ability to prevent lipopolysaccharide-induced of reactive oxygen species and nitric oxide production in a macrophage cell line (RAW 264.7). Olive stones that are issued from the production of olive oil, and table olives can therefore be considered as renewable by-products thanks to their compounds with high added value. These bioactive compounds can target the food natural additives markets, pharmaceutical and cosmetic industries, all of which are currently very receptive such natural products.
Graphic abstract
... The structural analysis of the most abundant compounds leads to their allocation into the group of secoiridoid compounds (elenolic acid derivatives) including oleuropein and structurally related substances (demethyloleuropein and ligstroside), and nüzhenide derivatives. In general, these compositional data agree with those obtained from olive pulp (Servili et al. 1999) and whole pits (Ben Mansour et al. 2015). Several of the identified compounds were present as glycosides in contrast with data from Alu'datt et al. (2011) who found the predominant phenolic compounds in olive seeds in free form. ...
Olive seeds, a potential food by-product from both table olive and olive oil industries, were examined for their overall proximate composition, oil, protein, mineral and phenolic components. Proximate analysis indicates that olive seeds are an unusually rich source of total dietary fibre (≅ 47% dry weight basis, DWB), as well as lipids (≅ 30%) and proteins (≅ 17%). Oil composition shows high levels of oleic (≅ 62% of total fatty acids) and linoleic (≅ 24%) acids, moderate concentrations of tocopherols (≅ 460 mg/kg) and squalene (≅ 194 mg/kg), and relatively high amounts of several sterols and non-steroidal triterpenoids. Olive seed proteins are a rich source of essential amino acids (about 46% of the total AA content). Olive seeds also contain significant amounts of some essential macro-elements (K, Ca, Mg, Na, P) and micro-elements (Zn, Mn, Cu). Phenolic compounds are present at relatively high quantities (≅ 2.8 mg/g seed, DWB); the most abundant belong to the group of secoiridoid compounds (elenolic acid derivatives) including oleuropein and structurally related substances (demethyloleuropein and ligstroside), and nüzhenide derivatives. Based on the general nutritional profile and nutraceutical components, olive seeds have value-added potential as a source of edible oil, proteins or meal serving as feed supplements.
... Specific compounds which are present in various tissues of the fruit like stone, leaf, mesocarp and exocarp have been discovered by the investigation of phenolic profiles in these tissues. For example, flavonoids (Figure 1) quercetin, rutin and luteolin-7-glucosidewere found to be present only in the fruit peel Servili et al.[41].Similarly, only olive seeds contain phenolic compounds salidroside and nuzhenide Ryan et al.[42]; Mansour et al.[43]. A crucial gene, CHI(Figure 1) was observed for enhancing flavonol production. ...
... Gl3 isomers are the methyloleoside derivatives of nuezhenide, and their MS 2 spectra were compared to those reported in the literature. 20 Other nuezhenide derivatives were found with m/z 701.7 (11) and 715.7 (12); these compounds shared the same fragmentation pattern and were assigned as neonuezhenide 26 and methoxy nuezhenide, 27 respectively. The fragments of the ion at m/z 701.7 (m/z 315.1, 297.2, and 135.1) were 16 Da greater than the typical fragments (m/z 299.1, 281.2, and 119.1), suggesting the hydroxy group was located on the phenylethanol moiety; the product ion that arose from the deprotonated molecular ions at m/z 715.7 were 30 Da greater than the typical fragments, suggesting the presence of a methoxy group. ...
Ripe O. fragrans fruit is composed of purple peels, green pulps and light brown seeds. Since the biological effects such as antioxidative activities and platelet-aggregation inhibition are related to the phenolic compounds and flavonoids in O. fragrans fruits, these components have a great potential as functional food ingredient. In the work, active components in O. fragrans fruits extraction were investigated by HPLC-ESI-MS/MS. A total of twenty-eight compounds were identified and sixteen components were first discovered in O. fragrans fruits, most of which were a series of phenylethanoid glucosides. These compounds are assigned as methyloleoside neonuezhenide and possible fragmentation pathway of mass spectrometry is first elucidated. Additionally, sensitive HPLC-ESI-MS/MS method for five phenylethanoid glycosides of salidroside, acteoside, isoacteoside, neonuezhenide and nuezhenide and two triterpenes of oleanolic acid and ursolic acid has been established for the quality of O. fragrans fruits comprehensively.
... From a total of 144 detected metabolites 56 (39%) were unambiguously or tentatively identified, amongst them sugars, amino acids, nineteen phenolics and twenty-five flavonoids (mainly C-glycosides). As further examples the comprehensive LC-MS/MS profiling of phenolics in olive stones [119], in brewery residues and chestnut leaves [120], or in Pitomba (Talisia esculenta), a widely consumed but little studied Brazilian exotic fruit [121], should be mentioned. In the latter nine phenolics were subsequently quantified by UPLC-QTOF-MS/MS with a previously validated method. ...
The separation, identification and quantification of constituents in complex plant extracts always has been, and most likely will be, a challenging task. Nevertheless, today a multiplicity of different separation techniques, specific stationary phases and detectors are available, helping to achieve the desired selectivity, sensitivity and speed for nearly any separation problem. The most prominent and popular technique in this area of research is definitely the combination of liquid chromatography and mass spectrometry. More than 40 years after its beginning LC-MS can be considered a well-established routine technique, however there is a steady advancement in terms of instrumentation (ultra-high-performance LC, ion mobility MS, etc.), the hyphenation of different techniques (supercritical fluid chromatography − mass spectrometry, two-dimensional techniques, etc.), or the type of analysed compounds (novel applications). The here presented review aims to consider all of these aspects, focusing on natural products/medicinal plants related LC-MS papers published within the years 2011–2016. It gives a short overview of recent technical trends as well summarizes the most relevant applications ordered by the type of natural products assessed (e.g. acids, alkaloids, flavonoids, terpenes). The respective reports are also differentiated according to the studies purpose (analysis of plant material or pharmacological investigation) and a special chapter is devoted to Traditional Chinese Medicine. For selected reports relevant methodological details are provided and limitations or advantages discussed, so that the current status of LC-MS for natural products analysis is reflected comprehensively.
... Although, the severity of attack mainly influenced by the virulence of the pathogen, it depends also on the resistance level of each olive cultivar [4]. However, recent studies of the olive cultivars susceptibility has revealed breaking down in the resistance of the main olive cultivar; Chemlali, which occupy more than 80% of the cultivated area [5]. Similarly, severe VWO epidemics occur in regions cropped with the cultivar; Chemlali for consecutive years [6]. ...
... Phytochemical analysis of the EP1 extract was performed through HPLC separation technique couled to both DAD and ESI-TOF/MS analysis (Ben Mansour et al., 2015). A Thermo Scientific System consisting of an AccelaU-HPLC unit with a photodiode array detector and an LTQ Orbitrap XL mass spectrometer fitted with an electrospray source was used. ...
Punica granatum L. is widely recognized for its potency against a broad spectrum of bacterial pathogens. The purpose of this study was to explore the inhibitory and the bactericidal activities of Punica granatum against Salmonella strains. The effect of extracts obtained from different parts (peels, seeds, juice and flowers) of pomegranate and using different solvents against Salmonella enterica serovars Kentucky and Enteritidis isolated from chicken meat was thus investigated. Salmonella strains were identified with the standard API-20E system and confirmed by real time PCR.
The obtained results showed that the highest antibacterial activity against Salmonella strains was observed with the peels ethanolic extract giving MIC values ranging from 10.75 to 12.5 mg/mL. The ethanolic extract of P. granatum Nana peels at 0.8 and 1.6 mg/g significantly inhibited the growth of Salmonella Kentucky in chicken meat stored at 4 °C.
The phenolic composition of the ethanolic peel extract was explored by HPLC coupled to both DAD and ESI/TOF-MS detections. The obtained results allowed the detection of 21 phytochemical compounds among which various phenolic compounds have been identified on the basis of their UV and MS spectra as well as with literature data. Among the detected compounds, anthocyanins, ellagitannins, ellagic acid derivatives and flavanols were further characterized through MS-MS analysis.
Our results showed thus that the Tunisian variety Nana pomegranate constitutes a good source of bioactive compounds with potent antimicrobial activity on the growth of Salmonella strains suggesting that the studied pomegranate cultivar could be a natural remedy to minimize the emergence of Salmonella enterica strains which is often involved in food borne illness.
... Subsequently, the behavior of these cultivars under inoculation condition was studied at physiological and molecular levels. Overall, the results of this study indicate that most of the Tunisian cultivars were extremely susceptible to VWO, including the two main cultivars, Chemlali and Chetoui, which represent approximately 70 % of the orchards (Ben Mansour et al. 2015). The resistance breakdown observed in these two cultivars is mainly due to the change in olive cultivation practices, Data were compared using the Tukey HSD test such as the transition from the rainfall regime to olive intensification, which resulted in the occurrence of favorable ecosystem for the development of many olive pathogens (López-Escudero et al. 2010). ...
New olive cultivars adapted to Tunisia’s growing conditions were examined for their resistance to verticillium wilt (VWO) to determine whether differences in susceptibility among currently grown cultivars might contribute to the management of this disease. Based on the evaluation of 14 cultivars, 10 were classified as susceptible or extremely susceptible (Chetoui, Chemlali, Rkhami, Jarboui, Zalmati, Jarboui, Oueslati, Manzanille, Picholine and Frangivento), 2 as moderately susceptible (Koroneiki and Coratina), and 2 as resistant (Meski and Sayali) to VWO. Three cultivars with different susceptibility levels were selected to examine the levels of hydrogen peroxide (H2O2), soluble sugars (SS), soluble proteins (SP), total polyphenols (TP), lipid peroxidation, activities of antioxidant enzymes, and fungal biomass in planta. V. dahliae DNA occurred early in the roots at 15 dpi and reached a maximum of 3.507 and 2.52 ng/100 ng of plant DNA, respectively, in the extremely susceptible and resistant cultivars. Fungal DNA in the stems occurred at 30 dpi and increased slowly to reach a maximum of 0.23 ng/100 ng of total DNA in the extremely susceptible cultivars. We showed that the amount of fungal DNA in planta was roughly correlated with the susceptibility to VWO (P < 0.0001; r = 0.95). The comparison of cultivars at the physiological level indicated that olive resistance is roughly correlated with the antioxidant enzymes activity, H2O2 concentration, and TP and SP contents. The results of this study open new perspectives for olive genetic improvement programs aiming at developing new cultivars resistant to this wilt.
... An Eclipse XDB-C18 column (250 mm× 4.6 mm, i.d., 5 µm particle size; Waters Co., Milford, MA) was used, maintained at ambient temperature (25 °C) with an injection volume of 10 µL and a flow rate of 0.8 mL/min. The mobile phase was composed of 0.25 % acetic acid in water (solvent A)-methanol (solvent B) at a flow rate of 0.8 mL/min, with the following steps: 0 min, 5 % B; 7 min, 35 % B; 12 min, 45 % B; 17 min, 50 % B; 22 min, 60 % B; 25 min, 95 % B; 27 min, 5 % B; and then a conditioning cycle of 5 min at the same conditions for the subsequent analysis [23]. ...
This paper reports the quality indices, the volatile components, phenolic compounds and the oxidative stability of monovarietal Tunisian cultivar (cv. Neb Jmel) extra-virgin olive oils cultivated in eight regions. Headspace solid-phase microextraction and HPLC–DAD were applied to analyze and quantify the volatile and phenolic compounds of the obtained extra-virgin olive oils. Twenty compounds have been identified and quantified, revealing the complex profile of Neb Jmel EVOO, composed, in order of abundance, by secoiridoids, phenolic alcohols, lignans, flavonoids and phenolic acids. A total of 40 volatile compounds belonging mainly to esters, aldehydes, ketones, aliphatic alcohols and hydrocarbons were determined. Significant differences in the proportions of volatile and phenolic constituents of oils from different geographical origins were observed. The major volatile component was the C6 aldehyde (hexanal and (E)-2-hexenal) fraction, whose content was highly variable between the areas studied. The content of (E)-2-hexenal ranged from 50.9 % in the Melloulech EVOO to approximately 39.8 % for El-Ala EVOO.
... Several studies that have been carried out on some of these plants have led to the development of natural antioxidant formulations for food, cosmetic, and other applications [1,2]. Among these natural compounds, phenols constitute one of the major groups of herbal compounds acting as radical scavengers and antioxidants [3,4]. Nowadays, scientific research reveals that the antioxidant properties of the plant extracts give beneficial effect to human health [5]. ...
Objective: To investigate the total phenolics, flavonoids and tannins content and the in-vitro antioxidant activities of methanolic extracts of six wild Mentha species which are Mentha aquatica, Mentha arvensis, Mentha piperita, Mentha pulegium, Mentha rotundifolia and Mentha villosa.
Methods: The Folin-Ciocalteu method was used to determine the total phenols content while flavonoids were estimated according to the aluminum chloride colorimetric method. To evaluate tannins content, vanilline and HCl were added to methanolic extracts. The antioxidant potential was measured by 1,1-diphenyl-2-picrylhydrazyl radical scavenging, ferrous ion chelating and the inhibition of β-carotene bleaching assays.
Results: The methanol extracts of Algerian mints were rich in phenolic compounds and exhibited powerful antioxidant activity ranging from 7.5 μg/mL to 44.66 μg/mL, which varied significantly among species. Mentha aquatica stood out with efficient antioxidant ability which was correlated to the high total phenolics content, followed by Mentha arvensis and Mentha piperita with very close values, comparing to Mentha pulegium, Mentha rotundifolia and Mentha villosa with lowest values.
Conclusions: These results show that methanolic extracts of Mentha species from Algeria have a great potential of polyphenols which can be used as a natural food preservative and antioxidant source.
... surprising since these compounds, especially flavonoids, act as UV filters, protecting some cell structures, like chloroplasts, from harmful effects of UV radiation [34]. In the review by Saoudi Antioxidants have recently become a topic of increasing interest to health and food science researchers and medical experts [36]. The antioxidant potential of F. carica pulps, peels and leaves was checked [13,18]. ...
Objective: To determine the total phenolic and flavonoid contents, antioxidant and antimicrobial activities of methanolic leaf extracts of ten Algerian fig (Ficus carica L.) varieties (uniferous, biferous and caprifig tree).
Methods: Phenolics were extracted by Soxhlet method and analyzed by the Folin–Ciocalteu colorimetric method. Flavonoids were determined by aluminum trichloride assay and the antioxidant capacity was determined by the 2,2-diphenyl-1-picrylhydrazyl radical scavenging assay. The antimicrobial activity was studied with the disc diffusion method and a macrodilution broth method was used to determine the minimal inhibitory concentrations and minimal lethal concentrations.
Results: The mean extract yield was 14.10% ± 0.66% (n = 10). Leaf extract of biferous followed by uniferous varieties had the highest total phenolic contents [(52.296 ± 5.232) and (48.973 ± 2.015) mg gallic acid equivalent/g of dry plant extract respectively], flavonoids [(14.388 ± 0.333) and (14.136 ± 1.082) mg quercetin equivalent/g of dry plant extract] and antioxidant capacity [IC50 (798.754 ± 108.590) and (825.004 ± 110.835) μg/mL]. Antioxidant capacity of fig leaves was significantly correlated with phenolic contents (r = 0.748). These extracts showed bactericidal activity and moderate antifungal activity, and the minimal inhibitory concentrations and minimal lethal concentrations were determined on Bacillus cereus and Staphylococcus aureus.
Conclusions: All tested extracts contain phenolic compounds and exhibited an antioxidant activity and an antimicrobial effect against Gram-positive and Gram-negative bacteria. Further researches on identification and purification of phenolic compounds are required.
... Antioxidants have recently become a topic of increasing interest to health and food science researchers and medical experts (Ben Mansour et al., 2015). The antioxidant activities of the fig achenes oil extract were measured (DPPH and ABTS) and compared to that of commercial synthetic antioxidants such as BHT (IC 50 = 9.12 lg/ mL, TEAC = 1.59 mM). ...
The olive oil sector generates a high quantity of biomasses every year, especially in the Mediterranean region. Olive pomace is the main one, but depending on the extraction and subsequent processing, other derived biomass by‐products are generated like pâté, exhausted olive pomace, olive stone, and residual pulp. Their sustainable valorization is crucial. Therefore, this review first conceptualizes the current situation of the olive oil sector and describes these biomasses from a qualitative and quantitative point of view. Second, information on the bioactive compounds they present, the technologies used for their extraction, and examples of applications for their extracts is provided. Third, since the extraction of bioactive compounds will generate new residual biomasses, this review takes a step forward by integrating the extraction step in biorefinery cascading schemes. It also analyzes the benefits of this integration, the contribution to a circular (bio)economy, and the achievement of sustainable development goals.
Several articles in the literature deal with and analyze components extracted from the olive tree, but these researches are mainly focused on the quality of olive oil and more precisely its volatile components, often related to their antioxidant properties, which denies other derivatives of the olive tree that are traditional sources of several healing broths. A thorough comparison of the richness of the different derivatives as well as the methods of extraction and identification will help to provide a useful decision-making tool. Olive tree derivatives were extracted in different ways to better understand the chemical composition of the Chemlali olive tree variety as well as to evaluate the efficiency of advanced extraction procedures. A comparison through the IC50 of the Chemlali variety with other olive cultivars was performed. It shows the richness of this variety in polyphenols. In addition, we present here a qualitative and quantitative table of basic chemicals for pharmacological use derived from olive oil, leaf, and bark that have been previously described in the literature. Diverse types and concentrations of phenolic compounds—an important class of natural antioxidants—can be found in different components of olives, including leaves, fruit, pits, seeds, bark, and paste. However, comprehensive studies are deficient in comparing the quantities extracted from these different sources. Indeed, this review attempt shows the diversity of Chemlali through the use of high-value-added molecules (VAT), which can be categorized as diterpenes such as tyrosol and phytol, triterpenes such as squalene, as well as cinnamates.
Bergenia ligulata is the prominent ayurvedic herb for anticancer activity. The leaf of Bergenia ligulata was extracted with methanol and evaluated by phytochemical analysis for the content of innumerable metabolites like primary and secondary. The antioxidant efficacy was assessed through method DPPH free radical scavenging activity. Estimation of total phenolic content, total flavonoid content and tannin content were done to confirm the presence of these photochemical. The cytotoxic effect was determined against the Adrenal gland cancer cell lines (PC12 using MTT assay). It was revealed from the phytochemical analysis of methanol extract of Bergenia ligulata that tannin, saponin, cardio glycosides, protein, quinines, phenols and flavonoid were present. A significant antioxidant activity was revealed by the methanol extract 42.8+3.40%. Quantity of total phenol content, total flavonoid content and tannin content were the highest in the139.8 +9.06mg of GAE/g, 77+6.40 mg of QE/g, 70.4+6.40mg of TAE/g at 500 µg concentration. At lowest concentration of 3.12 µg/ml of methanol extract of Bergenia ligulata cell death was observed with the highest value of 61.1+4.86% respectively. The IC 50 value of methanol extract of Bergenia ligulata was found to be 53.925% µg/ml respectively against PC12 cell line. The study suggests that methanol extract of Bergenia ligulata has significantly antioxidant property. Bergenia ligulata is a good candidate for isolation of antioxidant, total phenol content, total flavonoid content, tannin and anticancer activity that can be a breakthrough for pharmaceutical industry. The antioxidant activity present in Bergenia ligulata have strong cytotoxic activity suggests that it can be considered for anti-cancer treatment.
Objective
To determine the in vitro antioxidant and antimicrobial properties of Nephrolepis biserrata (Sw.) Schott leaf extracts against different microbial strains, including 4 Gram-positive bacteria, 4 Gram-negative bacteria, 3 yeast, and 4 mould
Methods
The agar well diffusion method examined Nephrolepis biserrata leaf extracts antimicrobial activity against test micro-organisms. Additionally, TPC (total phenolic content), TFC (total flavonoid content), and 2, 2-diphenyl-1-picrylhydrazyl (DPPH) free radical assay of extracts were determined.
Results
Preliminary phytochemical screening of all three extracts revealed the presence of tannins, terpenoids, alkaloids, saponin glycosides, and flavonoids. Results obtained were compared with the antibiotics Amphotericin B, Fluconazole, and Gentamicin used as standards. The mean zones of inhibition of methanol extract varied from 7 to 25 mm. However, with petroleum ether extract, the range varied from 9 to 12 mm and with acetone extract from 8 to 13 mm at two different concentrations of 250 and 500µg/disc. All extracts possessed significant antimicrobial activity against bacterial strain including Bacillus cereus, B.subtilis, Staphylococcus aureus, S.epidermis, Pseudomonas aeuginosa, Escherichia coli, Proteus Vulgaris, Klebsiella pneumonia compared to fungal microbes such as Cryptococcus luteolus, Candida albicans, C.tropicalis, Aspergillus candidus, A.niger, and Mucor hiemalis wehmer, respectively. However, amongst all the three extracts, methanol leaf extract showed maximum antimicrobial activity.
Conclusion
From the present study, it has been summarized that the antimicrobial activity of plants might be due to the presence of flavonoid and tannin components. In conclusion, still advanced research is required to isolate the active principles from plant extracts, showing antimicrobial activity that may lead to the development of a phytomedicine.
Salicylic acid is a phenolic plant growth regulator found in plants with various important physiological roles. This investigation was aimed to study the effect of exogenous application of salicylic acid on the growth, metabolism and health status of Mentha spicata, an aromatic medicinal plant having several monoterpenes and antioxidants which show various kinds of medicinal properties. In the present work, some growth and biochemical parameters were recorded at 30 and 60 days after treatment with different concentrations of salicylic acid (0, 100, 200 and 300 µg ml-1). Results clearly revealed that salicylic acid particularly at 200 µg ml-1 concentration significantly enhanced most of the growth and some of the biochemical attributes as well as the antioxidant property when compared with that of control plants. It can be concluded that exogenously applied salicylic acid at particular doses can enhance the biomass production as well as the medicinal potential of M. spicata as evidenced from some reliable physiobiochemical parameters.
The roots of O. fragrans are also a valuable resource in addition to its flowers and fruits. In this study, the HPLC-MS/MS method used for analyzing the chemical constituents in O. fragrans roots extract was developed, which showed high sensitivity for both qualitative and quantitative analysis. Thirty-two compounds were first discovered in O. fragrans roots, one compound of which was reported for the first time. The simultaneous determination method for acteoside, isoacteoside, oleuropein and phillyrin was validated to be sensitive and accurate. Then it was applied to determine the content of bioactive components in O. fragrans roots from different cultivars. The content of oleuropein and phillyrin in the twelve batches was relatively stable, while the content of acteoside and isoacteoside varied greatly. Moreover, the therapeutic material basis and mechanism of O. fragrans roots exerting its traditional pharmacodynamics were analyzed by network pharmacology. The results showed that O. fragrans roots might be effective for the treatment of inflammation, cardiovascular disease, cancer, and rheumatoid arthritis, which is consistent with the traditional pharmacodynamics of O. fragrans roots. This work can provide the analytical method for the comprehensive development of O. fragrans roots.
Olive oil is a characteristic product of Mediterranean countries, and its production is rapidly expanding to many other regions due to the health benefits attributed to the consumption of high-quality olive oil. Taking into account that the oil content is, on average, only 20% by weight of olives, a great amount of biomass, including leaves, pits, and pomace, is produced in the mill along with the main product. Moreover, the pruning of olive trees and the production of the olive pomace also generates a great amount of biomass. Currently, the usual practices for disposal of these different biomasses do not take advantage of the wide range of products that can be produced from them. This work summarizes the most relevant practices considering both the bioprocesses studied for the exploitation of the olive-derived biomass and the potential products obtained. The integration of processes in a single facility, i.e., the concept of a biorefinery based on olive-derived biomass, is also reviewed, including technoeconomic and environmental assessment.
Olive trees are cultivated in more than 40 countries worldwide over more than 10 million hectares. In addition to olive oil, a large amount of biomass is produced annually. All this biomass must be adequately handled and disposed of. Conventional disposal methods include direct burning or spreading in fields, but this has economical costs and environmental concerns, as well as wasting a source of energy and chemicals. This review summarizes the most recent proposals for the use of biomass derived from olive tree cultivation and olive oil production processes. Biomass produced from pruning, leaves, olive stones and pomace, extracted olive pomace, and olive waste water are considered, and the main options for processing are reviewed according to recent advances in the literature. The biorefinery concept applied to olive-derived biomass is also presented and representative works are discussed. © 2017 Society of Chemical Industry and John Wiley & Sons, Ltd
Antioxidant contents and activities of different extracts from four Tunisian pomegranate peels, locally called “Acide”, “Gabsi”, “Nebli” and “Tounsi”, were studied. Peels samples were extracted with three solvents (water, ethanol and acetone). For each extract, the total phenol contents and antioxidant activity were evaluated. The highest values of polyphenol, tannins, flavonoids and anthocyanins were recorded in the acetone extract of Acide ecotype with 304.6 mg gallic acid equivalent/g; 292.23 mg gallic acid equivalent/g; 15.46 mg Quercetin/g and 54.51 mg cy-3-glu/100 g, respectively. The acetone extract of Acide ecotype also showed the highest free radical-scavenging and reducing power activity compared to other extracts. Besides, the phytochemical analysis by LC–MS/MS revealed a high content of ellagitannins with punicalagin and punicalagin derivatives as the major compounds that might be responsible for promising antioxidant activity of pomegranate peel extracts. Two compounds (Castalagin derivative and Galloyl-bis-HHDP-hex derivative) were detected only in “Acide” ecotype in important contents.
Introduction:
Olea europaea L. organs such as leaves, stems and roots have been associated with numerous in vivo and in vitro biological activities and used for traditional medicinal purposes. However, tree wood is an untapped resource with little information about their chemical composition.
Objective:
That is why, the objective of this study is to increase the knowledge about phytochemicals from 'Chemlali' olive wood by means of mass spectrometry-based analyses. Its comparison with by-products derived from leaves was also studied.
Methodology:
Hydromethanol extracts from wood and leaves with stems of 'Chemlali' olive cultivar were analysed using reversed-phase (RP) high-performance liquid chromatography (HPLC) coupled to two detection systems: diode-array detection (DAD) and quadrupole time-of-flight (QTOF) mass spectrometry (MS) in negative ion mode. Tandem MS experiments were performed to establish the chemical structure of olive phytochemicals.
Results:
A total of 85 compounds were characterised in the studied olive parts and classified as: sugars (3), organic acids (5), one phenolic aldehyde, simple phenolic acids (6), simple phenylethanoids (5), flavonoids (14), coumarins (3), caffeoyl phenylethanoid derivatives (6), iridoids (5), secoiridoids (32), and lignans (5). To our knowledge, the major part of these metabolites was not previously reported in olive tree wood, and 10 olive chemical constituents were identified for the first time in the Oleaceae family.
Conclusion:
The results presented here demonstrated the usefulness of the methodology proposed, based on RP-HPLC-DAD-ESI-QTOF-MS and MS/MS, to develop an exhaustive metabolic profiling and to recover new biologically active compounds in olive wood with pharmacologic and cosmetic potential. Copyright © 2017 John Wiley & Sons, Ltd.
Background:
Olive oil contains compounds with interesting biological activities which are influenced by the cultivar, the geographic origin and other factors. The aim of this work was to investigate these factors in Neb Jmel olive oil from various Tunisian origins. The aim of this work was to attest the influence of geographic conditions on phenolic composition of Neb Jmel olive oil and consequently on the antioxidant compounds, and to verify if it is permit to discriminate the geographical origin.
Results:
The characterization of extra-virgin Neb Jmel olive oil produced in their original place has been conducted. Owing to the effect of the genotype and environmental, agronomic and technological factors on the chemical composition of olive oil and its quality, all studied olives were collected at the same season, and their oil obtained under the same processing technique. Many analyses were carried out to characterize the different olive oils: free acidity, peroxide value, fatty acid composition, Rancimat assay, pigments content and phenolic compounds by (1) H NMR. A recently developed method for the direct measurement of the oleocanthal and oleacein levels in olive oil by quantitative (1) H NMR was applied. The method was applied to the study of four Neb Jmel olive oils samples, and a broad variation of concentrations of all four secoiridoids was recorded. The concentration of each one ranged from 55 to 529 mg/kg and the sum of the four major secoiridoids (known as D3) ranged from 436 to 1063 mg/kg.
Conclusion:
The quantification of major phenolic compounds of olive oil by NMR method indicated that environmental conditions influence the production of qualitative phenolic fractions. All these compounds can be used as base '' markers' to characterize and differentiate these olive oil on geographic origin.
The present work has been carried out to ascertain the influence of different processing systems employed in olive process on the chemical composition, quality and stability of three Chemlali olive oils. Among these oils, two were classified as extra-virgin olive oils and the third named repassed olive oil was classified as an ordinary virgin olive oil. The analysis of the effect of the processing (two- and three-phases) on the analytical determinations values, revealed statistically significant differences (p<0.05) in some parameters, mainly in oxidative stability, antioxidant activity, total waxes, total phenols, o-diphenols and α-tocopherol contents as well as phenolic composition. The phenolic composition values were higher in the extra-virgin olive oil obtained from the two-phase system than in that obtained from the three-phase processing because it does not require the addition of water to the olive paste. Nevertheless, they were lower in the ordinary virgin olive oil (repassed olive oil) which was obtained by introducing hot water to the wet residues into the centrifugation processing at two-phases, than those in the extra-virgin olive oils obtained from the two- and three-phase processing.
The present work aims at the characterizing chemlali extra-virgin olive oils from different locations in northern, central and southern Tunisia in terms of their quality indices, fatty acids, sterol content, phenolic composition and sensory profiles to show the classification of oil samples according to the geographical area. The majority of the analytical parameters have presented statistically significant differences (p < 0.05). The main sterols found in all chemlali olive oils were β-sitosterol, ∆-5-avenasterol, campesterol and stigmasterol. The phenolic compounds present in five olive oil samples were analysed by high-performance liquid chromatography (HPLC) method, thus identifying 16 phenolic compounds belonging to different phenolic types. The results have shown no qualitative differences in the phenolic fractions among extra-virgin olive oils from different geographical regions. However, the quantitative differences were observed in a wide number of phenolic compounds. In all studied olive oil samples, secoiridoids were the most abundant, followed by lignans, phenolic alcohols and flavonoids, respectively. Although there is no significant influence on the sensory scores of oils, some slight changes in sensorial profiles were noted: slightly higher intensities of sensory characteristics that are pungent, fruity and bitter in chemlali olive oil from Hammamet and Gafsa.
Phenolic compounds from olive (Olea europaea)
Certain plant properties, such as the colour, the nutritional value, the
resistance to microorganisms, the pharmacologic eflects and the
organoleptic character, are due to the phenolic compounds. lt is interesting
the study o! phenolic compounds from olive because they:
-lnhibit Gram+ microorganisms, such as Lactobacillus, which are
involved in the fermentation o! the olive fruit.
-lnhibit the activity o! cellulases and other enzymes.
-Contribute to the stability and organoleptic character o! virgin olive
oil.
-lnhibit the eflect o! microorganisms involved in the anaerobic
depuration o! vegetation water. Thus, the phenolic compounds are
the major bothersome contaminants o! these wastewater.
-Are natural antioxidants.
In the present review we describe the composition o! !he phenolic compounds
from the olive fruit (pulp and seed), the olive oil and its by-products
(vegetation water and rape) and the olive leaves.
A study on the possibility of recycling waste materials, such as olive husk, the solid phase derived from an olive oil mill, in blend with thermoplastic polymers to produce new materials for manufacturer of, for example, containers and formworks, has been carried out. The present paper describes the methodology used for the preparation and the characterization of composite samples prepared by mixing various percentages of olive husk and polypropylene. A screening on the chemical-physical characteristics of the olive husk is reported, as well as a set of tests applied to evaluate the mechanical properties of the manufactured products obtained.
Olive from Olea europaea is native to the Mediterranean region and, both the oil and the fruit are some of the main components of the Mediterranean diet. The main active constituents of olive oil include oleic acid, phenolic constituents, and squalene. The main phenolic compounds, hydroxytyrosol and oleuropein, give extra-virgin olive oil its bitter, pungent taste. The present review focuses on recent works that have analyzed the relationship between the major phenolic compound oleuropein and its pharmacological activities including antioxidant, anti-inflammatory, anti-atherogenic, anti-cancer activities, antimicrobial activity, antiviral activity, hypolipidemic and hypoglycemic effect.
From the seeds of Olea europaea , three known glucosides, salidroside (tyrosol-glucose), nüzhenide (glucose-elenolic acid-glucosetyrosol) and nüzhenide-oleoside have been isolated as well as two new secoiridoid glucosides with tyrosol, elenolic acid and glucose moieties in unknown sequence.
Se han aislado de semillas de aceituna ( Olea europaea ) tres glucósidos secoiridoides ya conocidos: salidrósido (tirosol-glucosa), nuzhenida (glucosa-ácido elenólico-glucosa-tirosol) y nuzhenida-oleósido, así como otros dos glucósidos secoiridoides que también tienen en su molécula tirosol, ácido elenólico y glucosa cuyas secuencias no se han podido establecer.
The seed extracts of olive tree cultivars were analyzed by reverse phase HPLC with diode array detection and mass spectrometry. HPLC hyphenation with mass spectrometry (ESI source) in both polarity modes enabled the identification in olive seeds of nüzhenide and nüzhenide 11-methyl oleoside, among other 11-methyl oleosides, by means of MS<sup>n</sup>. The methods used allowed us to obtain olive seed profiles of phenolic components and to conclude that they are mainly secoiridoids. The quantification of detected phenolic secoiridoids was also achieved using ultraviolet detection (λ = 240 nm) which enabled comparison of the samples. Nüzhenide and nüzhenide 11-methyl oleoside were the major components detected in olive seeds of all the cultivars studied, but variations in individual components of olive seeds were verified among the cultivars. The results also support the existence of di and tri(11-methyl oleosides) of nüzhenide.
Extractos de semillas de tres cultivos fueron analizados por HPLC en fase reversa con detector de diodos y espectrometría de masas. La unión del HPLC con la especrometría de masas (modo ESI) en ambas polaridades permitió la identificación de nuzenida y 11-metil oleósido de nuzenida entre otros 11-metil oleósidos. El método usado nos permitió obtener los perfiles de los compuestos fenólicos en las semillas de aceitunas y concluir que ellos son secoiridoides. La cuantificación de los secoiridoides fenólicos detectados fue también llevada a cabo usando detección por ultravioleta (λ = 240 nm) lo que permitió la comparación de las muestras. Nuzenida y el 11-metil oleósido de nuzenida fueron los principales componentes detectados en semillas de aceitunas en todos los cultivos estudiados, aunque variaciones en los componentes individuales de las semillas de aceitunas fueron verificados entre los cultivos. Los resultados también apoyan la existencia de di y tri(11-metil oleósidos) de nuzenida.
Olive stone meal is a low-digested fibre source potentially useful in the prevention of digestive troubles in growing rabbit permitting a better balance of dietary fibre fractions. To evaluate its efficacy, three experimental diets containing 0, 3 or 6% olive stone meal were fed to 222 rabbits from weaning (28 d) to slaughter (73 d). Olive stone inclusion increased the proportion of large dietary particles while did not affect growth performance, digestive physiology and carcass and meat quality. Due to optimum health status observed in all experimental groups, the preventive action of olive stone meal against the occurrence of digestive troubles was not proven.
Hydrophilic phenols are the most abundant natural antioxidants of virgin olive oil (VOO), in which, however, tocopherols and carotens are also present. The prevalent classes of hydrophilic phenols found in VOO are phenolic alcohols, phenolic acids, flavonoids, lignans and secoiridoids. Secoiridoids including aglycon derivatives of oleuropein, demethyloleuropein and ligstroside, that are present in olive fruit, are the most abundant phenolic antioxidants of VOO. In this paper, the phenolic composition of VOO as well as the agronomic and technological parameters that affect their concentration in the oil are discussed. The olive cultivar and the ripening stage of fruit, in fact, have always been the most studied agronomic aspects that affect phenolic concentration in VOO. However, the malaxation conditions and the extraction systems used to separate oil from olive pastes (i.e. pressure three-phases and two-phases centrifugation systems) are also of great importance.
We studied the production of furfural by acid hydrolysis of olive stones, which in Spain are an abundant lignocellulosic residue derived from the production of olive oil. We focused on the hydrolysis in dilute sulfuric acid (0.05 to 0.250moll−1), at high temperature (220–240°C), and short reaction times, of a few minutes at the most. The experimental study was performed in a tubing-bomb reactor system that approximately reproduces the temperature profiles obtained in a continuous tubular reactor. We obtained maximum furfural yields ranging from 50% to 65% of the potential depending on acid concentration and temperature.
Olive stone residues (23%wt) were liquefied in phenol (71%wt) in the presence of sulfuric acid (6%wt) as catalyst at 170°C during 2h. A 500 ml classic reactor under atmospheric conditions was used to establish the characteristics of the new 2001 liquefaction reactor. The liquefied products can be used as raw material for phenol-formaldehyde resins. The batch feeding procedure, the average temperature and the configuration of the reactor largely determined the viscosity and the molecular weight of the liquefied products. These parameters were positively modified by the constantly presence of olive stone moisture and water from depolymerization in the reaction medium. A jacketed cooling wall in the upper half of the 2001 reactor and a heat exchanger were necessary to accelerate vapour condensation, and to improve the contact in the reaction mixture. The recovery of liquefied products was also improved by using a closed container with a pressure-equalizing system that avoids the release of phenol vapour to the atmosphere.
The removal of As(III) from aquatic solutions at different concentrations and pH by using four types of activated carbons obtained from solvent extracted olive pulp and olive stone waste materials was studied. The adsorbents are obtained by chemical (K2CO3 and HNO3) activation and physical (water vapor) activation. The results show that carbons produced by chemical and physical activation of solvent extracted olive pulp and olive stones are efficient adsorbents for arsenic removal. Arsenic adsorption follows a Langmuir isotherm. The best results were obtained with the adsorbent, obtained from extracted olive pulp by pyrolysis in the presence of water vapor. The maximum removal was found to be 18.60 μmol/g. The adsorption capacity for adsorbents, obtained from extracted olive pulp and olive stones, is 11.42 and 9.85 μmol/g, respectively. The test showed that alkaline aqueous medium favored the removal of As(III). Some experiments were carried out to study the oxidation of arsenite to arsenate in the presence of activated carbons.
Pneumatically assisted electrospray (ionspray) coupled with liquid chromatography was applied in the identification of antioxidants present in traces in the leaves of Olea europea L. cv. Cassanese, a typical olive tree from the northeastern part of Calabria region in Italy. The structures of these potential biomarkers were evaluated with reference to established mass spectrometric rules or, in one case, by matching the tandem mass spectrum of the unknown with that of an authentic sample obtained by synthesis. Copyright © 1999 John Wiley & Sons, Ltd.
Electrospray ionization (ESI) is nowadays the most important technique for on-line liquid chromatography/mass spectrometry (LC/MS) coupling. Different ESI probe designs including the microESI and pneumatically assisted ESI (ionspray) interfaces allow the introduction of sample at flow-rates ranging from a few hundred nl min−1 to 1–2 ml min−1. In this paper, an overview of the different LC/ESIMS devices is presented from the point of view of their flow compatibility. Several parameters for LC/ESIMS miniaturization and its effects on sensitivity are considered from the practical point of view. Low-flow ESI requires the use of narrow-bore and capillary columns. Sample preconcentration microdevices are recommended in order to circumvent some miniaturization drawbacks such as the low optimum injection volume and the low column capacity. Some considerations on fused-silica microcolumn and microESI needle construction are also presented. Copyright © 1999 John Wiley & Sons, Ltd.
The growing interest in the substitution of synthetic food antioxidants by natural ones has fostered research on vegetable sources and the screening of raw materials for identifying new antioxidants. Oxidation reactions are not an exclusive concern for the food industry, and antioxidants are widely needed to prevent deterioration of other oxidisable goods, such as cosmetics, pharmaceuticals and plastics. Polyphenols are the major plant compounds with antioxidant activity, although they are not the only ones. In addition, other biological properties such as anticarcinogenicity, antimutagenicity, antiallergenicity and antiaging activity have been reported for natural and synthetic antioxidants. Special attention is focussed on their extraction from inexpensive or residual sources from agricultural industries. The aim of this review, after presenting general aspects about natural antioxidants, is to focus on the extraction of antioxidant compounds (mainly polyphenols) from agricultural and industrial wastes, as well as to summarize available data on the factors affecting their antioxidant activity and stability, and, in some cases, the reported major active compounds identified.
The molecular structure of the microcomponents of olive fruit was investigated in order to evidence new molecules which could be transferred to the resulting oil and therefore be typical of olive oil. The three glucosides of 2(3,4-dihydroxy-phenyl)ethanol, 1, 2 and 3 were isolated together with other glucosides previously identified in Olea europaea. Glucosides 1–3 were detected in the olive oil, there being always present a small quantity of water as an emulsion, together with the aglycone, the 2(3,4-dihydroxy-phenyl)ethanol. The presence of glucosides 1–3 is closely linked with the organoleptic characteristics and to the recognized antioxidant properties of olive oil..
The chemical modification of lignocellulosic materials based on waste flour, using catalyst and solvent-free reactions with acetic and propionic anhydride, was studied. The reaction of esterification between the acetyl/propionyl groups and the hydroxyl groups of the flour was confirmed by Fourier transform infrared (FTIR) analysis, while its extent was assessed by titration. Thermogravimetric analysis (TGA), X-ray diffraction (XRD) and scanning electron microscopy (SEM) were used to characterize the thermal stability, crystallinity and surface morphology of the untreated and esterified flours. The ester content of all three flours was higher for the treatment with acetic as compared to propionic anhydride. The highest extent of the esterification was achieved for the olive husk flour due to its high lignin/hemicelluloses content. The esterified flours exhibited a decreased hydrophilicity as indicated by their moisture content reduction, while their thermal stability was slightly decreased. It was also shown that the flour crystallinity decreased slightly as a result of esterification.
Lactobacillus plantarum is the main species responsible for the spontaneous fermentation of Spanish-style green olives. Olives and virgin oil provide a rich source of phenolic compounds. This study was designed to evaluate inhibitory growth activities of nine olive phenolic compounds against four L. plantarum strains isolated from different sources, and to explore the L. plantarum metabolic activities against these phenolic compounds. None of the nine compounds assayed (oleuropein, hydroxytyrosol, tyrosol, as well as vanillic, p-hydroxybenzoic, sinapic, syringic, protocatechuic and cinnamic acids) inhibited L. plantarum growth at the concentration found in olive products. Oleuropein and tyrosol concentrations higher than 100 mM were needed to inhibit L. plantarum growth. On the other hand, sinapic and syringic acid showed the highest inhibitory activity since concentrations ranging from 12.5 to 50 mM inhibited L. plantarum growth in all the strains analyzed. Among the nine compounds assayed, only oleuropein and protocatechuic acid were metabolized by L. plantarum strains grown in the presence of these compounds. Oleuropein was metabolized mainly to hydroxytyrosol, while protocatechuic acid was decarboxylated to catechol. Metabolism of oleuropein was carried out by inducible enzymes since a cell-free extract from a culture grown in the absence of oleuropein was unable to metabolize it. Independent of their isolation source, the four L. plantarum strains analysed showed similar behaviour in relation to the inhibitory activity of phenolic compounds, as well as their ability to metabolize these compounds.
Two new secoiridoid glucosides, namely iso-oleonuezhenide (1) and methyloleoside 7-ethyl ester (2), along with five known ones, oleonuezhenide (3), nuezhenide (4), oleuropein (5), G13 (6), and jaspolyside methyl ester (7), were isolated from the fruits of Ligustrum lucidum. Their structures were assigned based on 1H-NMR, 13C-NMR, and 2D-NMR analyses, in combination with HR-MS experiments and the comparison with literature data of related compounds, as well as on chemical experiments. We have examined the ability of these compounds to activate ERK and CREB in cultured cortical neurons. Our studies demonstrate that compound 1 induces ERK and CREB phosphorylation in primary cortical neurons in a dose- and temporal-dependent manner, suggesting its bioactivity on neurons.
The recent explosion of interest in the bioactivity of the flavonoids of higher plants is due, at least in part, to the potential health benefits of these polyphenolic components of major dietary constituents. This review article discusses the biological properties of the flavonoids and focuses on the relationship between their antioxidant activity, as hydrogen donating free radical scavengers, and their chemical structures. This culminates in a proposed hierarchy of antioxidant activity in the aqueous phase. The cumulative findings concerning structure-antioxidant activity relationships in the lipophilic phase derive from studies on fatty acids, liposomes, and low-density lipoproteins; the factors underlying the influence of the different classes of polyphenols in enhancing their resistance to oxidation are discussed and support the contention that the partition coefficients of the flavonoids as well as their rates of reaction with the relevant radicals define the antioxidant activities in the lipophilic phase.
A method for the screening of antioxidant activity is reported as a decolorization assay applicable to both lipophilic and hydrophilic antioxidants, including flavonoids, hydroxycinnamates, carotenoids, and plasma antioxidants. The pre-formed radical monocation of 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS*+) is generated by oxidation of ABTS with potassium persulfate and is reduced in the presence of such hydrogen-donating antioxidants. The influences of both the concentration of antioxidant and duration of reaction on the inhibition of the radical cation absorption are taken into account when determining the antioxidant activity. This assay clearly improves the original TEAC assay (the ferryl myoglobin/ABTS assay) for the determination of antioxidant activity in a number of ways. First, the chemistry involves the direct generation of the ABTS radical monocation with no involvement of an intermediary radical. Second, it is a decolorization assay; thus the radical cation is pre-formed prior to addition of antioxidant test systems, rather than the generation of the radical taking place continually in the presence of the antioxidant. Hence the results obtained with the improved system may not always be directly comparable with those obtained using the original TEAC assay. Third, it is applicable to both aqueous and lipophilic systems.
The results demonstrate the potential of electrospray ionisation mass spectrometry for the specific detection of phenolic species in olives. Phenolic compounds were detected with greater sensitivity in the negative ion mode, but results from positive and negative ion modes were complementary with the positive ion mode showing structurally significant fragments. This is demonstrated by the identification of oleuropein and isomers of verbascoside. The structure of the latter were confirmed by retention, mass spectral and nuclear magnetic resonance data. These isomers have not previously been reported in olive.
The phenolic composition of peel, pulp, and seed of the olive fruit was studied for several Italian cultivars used for oil extraction. The seed contained a compound never previously detected in peel and in pulp. The spectroscopic characterization of this compound proved, for the first time, the presence of nüzhenide in the olive seed. Study of the phenolic composition showed that oleuropein, demethyloleuropein, and verbascoside were present in all of the constitutive parts of the fruit; by contrast, nüzhenide was exclusively present in the seeds of all the cultivars at all ripening stages studied.
A simple analytical method for the quantitative determination of phenols, flavones, and lignans in virgin olive oils was developed. The polar fraction was isolated from small amounts of oil sample (2.5 g) by solid-phase extraction (SPE) using diol-phase cartridges, and the extract was analyzed by reversed-phase HPLC coupled with diode array UV detection. Chromatographic separation of pinoresinol, cinnamic acid, and 1-acetoxypinoresinol was achieved. Repeatability (RSD < 6.5%), recovery (> 90%), and response factors for each identified component were determined. SPE on amino-phase cartridges was used for isolating acidic phenols and as an aid for phenol identification. For the first time, 2-(4-hydroxyphenyl)ethyl acetate was detected in olive oils. The aldehydic structure of the ligstroside aglycon was confirmed by NMR spectroscopy. The colorimetric determination of total o-diphenolic compounds by reaction with molybdate was consistent with their HPLC determination. Differences between results obtained by liquid-liquid extraction and SPE were not statistically significant.
This investigation was designed to characterize phenolic metabolism of the olive cultivar, Hardy's Mammoth, by examining its constitutive tissues. The phenolic profiles of pulp, seed, stone, and new and old season leaves were monitored over two fruiting seasons, to investigate possible relationships between tissues and phenol content and to determine the impact of alternate fruit bearing. No major qualitative differences in phenolic composition were found between the various tissues; however, distinct differences between the tissues with respect to quantifiable phenols were established. Relationships between 2-(3,4-dihydroxyphenyl)ethyl (3E,4E)-4-formyl-3-(2-oxoethyl)hex-4-enoate ester, oleuropein, and hydroxytyrosol in pulp and leaf were identified and found to be related to alternate bearing. Concentrations of 5-caffeoylquinic acid in old season leaves differed dramatically between seasons, confirming earlier studies.
Convenient syntheses were developed to obtain on a multigram scale the novel taste enhancer N-(1-carboxyethyl)-6-(hydroxymethyl)pyridinium-3-ol 1, called alapyridaine, as a racemic mixture and as pure (+)-(S) and (-)-(R) enantiomers, respectively. 5-(Hydroxymethyl)-2-furaldehyde was used as key intermediate and was reacted with l-alanine under alkaline conditions to obtain racemic 1. Alternatively, reductive amination of 5-(hydroxymethyl)-2-furaldehyde with Raney-Ni/hydrogen and l- or d-alanine followed by mild oxidation led to (+)-(S)-1 and (-)-(R)-1, respectively. Racemization was promoted under alkaline and boiling conditions via a carbanion, the formation of which was facilitated by the electron-withdrawing effect of the iminium cation and the resonance-stabilizing capacity of the pyridinium moiety. Under these conditions, 1 was obtained in a 1:1 mixture of the phenol (1) and phenolate (1-H) forms as shown by X-ray diffraction. Racemic 1 formed monoclinic crystals of high molecular organization in which the phenol-type (RS)-1, the phenolate-type (RS)-1-H, sodium cations, and ethanol molecules are present. The crystal structure of [Na(1)(1-H).(C(2)H(6)O)] shows one-dimensional mu(2)-bridging-oxygen polymers stabilized by a three-dimensional network of ionic, hydrogen bond, and pi-stacking interactions with channels occupied by solvent molecules.
Adulteration of vegetable oil is of concern for both commercial and health reasons. Compositional based fingerprints can potentially reveal both the oil source and its possible adulteration. Here, electrospray ionization (ESI) Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS) resolves and identifies literally thousands of distinct chemical components of commercial canola, olive, and soybean oils, without extraction or other wet chemical separation pretreatment. In negative-ion ESI FT-ICR MS, the acidic components of soybean oil are easily distinguished from those of canola and olive oil based on relative abundances of C(18) fatty acids, whereas olive oil differs from canola and soybean oil based on relative abundances of tocopherols. In positive-ion ESI FT-ICR MS, the three oils are readily distinguished according to the relative abundances of di- and triacylglycerols with various numbers of double bonds in the fatty acid chains. We demonstrate the detection of soybean oil as an adulterant of olive oil, based on relative abundances of members of each of several chemical families. We suggest that the detailed chemical compositions of vegetable oils can be used to characterize them and to detect and identify adulterants.
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 beta-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.
Activated carbon was produced from olive stones(OSAC) by a physical process in two steps. The adsorption character of this activated carbon was tested on three colour dyes molecules in aqueous solution: Methylene blue (MB), Rhodamine B (RB) and Congo Red(CR). The adsorption equilibrium was studied through isotherms construction at 30 degrees C, which were well described by Langmuir model. The adsorption capacity on the OSAC was estimated to be 303 mg/g, 217 mg/g and 167 mg/g respectively for MB, RB and CR. This activated carbon has a similar adsorption properties to that of commercial ones and show the same adsorption performances. The adsorption kinetics of the MB molecule in aqueous solution at different initial concentrations by OSAC was also studied. Kinetic experiments were well fitted by a simple intra-particle diffusion model. The measured kinetics constant was influenced by the initial concentration and we found the following correlation: Kid = 1.55 C0(0.51).
Two new secoiridoid glucosides, oleonuezhenide and isonuezhenide, have been isolated along with known secoiridoid glucosides, from the fruits of LIGUSTRUM JAPONICUM. Their structures have been elucidated on the basis of chemical and spectral data.
Two flavonol tetraglycosides comprising a trisaccharide at C-3 and a monosaccharide at C-7 were isolated from the leaves of Styphnolobium japonicum (L.) Schott and characterised as the 3-O-alpha-rhamnopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-glucopyranoside-7-O-alpha-rhamnopyranosides of quercetin and kaempferol. The 3-O-alpha-rhamnopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-galactopyranoside-7-O-alpha-rhamnopyranoside of kaempferol, the 3-O-alpha-rhamnopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-glucopyranosides of kaempferol and quercetin and the 3-O-alpha-rhamnopyranosyl(1-->2)[alpha-rhamnopyranosyl(1-->6)]-beta-galactopyranoside of kaempferol were also obtained from this species for the first time. Some or all of these flavonol tetra- and triglycosides were detected in 17 of 18 specimens of S. japonicum examined from living and herbarium material, although the most abundant flavonoid in the leaves was generally quercetin 3-O-alpha-rhamnopyranosyl(1-->6)-beta-glucopyranoside (rutin). The triglycosides, but not the tetraglycosides, were detected in herbarium specimens of Styphnolobium burseroides M. Sousa, Rudd & Medrano and Styphnolobium monteviridis M. Sousa & Rudd, but specimens of Styphnolobium affine (Torrey & A. Gray) Walp. contained a different profile of flavonol glycosides. The flavonol tetra- and triglycosides of S. japonicum were also present in leaves of Cladrastis kentukea (Dum. Cours.) Rudd, a representative of a genus placed close to Styphnolobium in current molecular phylogenies. An additional constituent obtained from leaves of Styphnolobium japonicum was identified as the maltol derivative, 3-hydroxy-2-methyl-4H-pyran-4-one 3-O-(4'-O-p-coumaroyl-6'-O-(3-hydroxy-3-methylglutaroyl))-beta-glucopyranoside.
Chemical screening using reversed phase HPLC-photodiode array detection (RPLC-DAD) and RPLC-electrospray ionisation mass spectrometry (RPLC-ESI-MS) is widely applied as an approach to streamline natural products research. The full potential of this approach is demonstrated in this paper by application to the chemical screening of olive products including olive mill waste (OMW). Out of 100 biophenols previously reported in olive products, the on-line RPLC-DAD-ESI-MS was able to confirm the presence of 52 compounds in OMW. This included a number of simple phenols, flavonoids and secoiridoids. By careful examination of the combined DAD and ESI-MS data, extra information was elucidated including: the site of glycosidation on the phenol ring of hydroxytyrosol; the identity of the other luteolin-glucoside isomer as luteolin-4'-O-glucoside; identifying rutin rather than the previously reported hesperidin (and the reasons for possible mis-assignment); and the detection of diastereomers of 4-hydroxyphenylethyl alcohol-deacetoxy elenolic acid dialdehyde (4-HPEA-DEDA) and 3,4-dihydroxyphenylethyl alcohol-deacetoxy elenolic acid dialdehyde (3,4-DHPEA-DEDA).
The olive stone and seed are an important byproduct generated in the olive oil extraction and pitted table olive industries. As a lignocellulosic material, the hemicellulose, cellulose and lignin are the main components of olive stone as wells as protein, fat, phenols, free sugars and poliols composition. The main use of this biomass is as combustion to produce electric energy or heat. Other uses such as activated carbon, furfural production, plastic filled, abrasive and cosmetic or other potential uses such as biosorbent, animal feed or resin formation have been cited. In this article, an overview of the characterization and main uses of olive stone and seed are described for the first time. Also, this review discusses the potential use of this material based on each component. In this way, a new approach to the olive stone and seed by pretreating with a steam explosion followed by chemical fractionation is described.
For a discussion of the Journal's expectations for compound characterization, please read Compound Identification: A Journal of Agricultural and Food Chemistry Perspective
- Novel Compound Characterization
Novel Compound Characterization. For a discussion of the Journal's expectations for
compound characterization, please read " Compound Identification: A Journal of
Agricultural and Food Chemistry Perspective " by R. J. Molyneux and P. Schieberle. J.
DOI: 10.1021/jf070242j) It is essential that novel compounds, either synthetic or isolated from natural sources, be characterized rigorously and unequivocally. Supporting data normally include physical form, melting point (if solid
- Agric
- Chem
Agric. Food Chem. 2007, 55, 4625–4629 (DOI: 10.1021/jf070242j). It is essential that novel
compounds, either synthetic or isolated from natural sources, be characterized rigorously and
unequivocally. Supporting data normally include physical form, melting point (if solid), UV/IR
spectra if appropriate,
1 H and
13 C NMR, mass spectrometric data, and optical rotation (when
compounds have chiral centers).
Analysis of Polyphenolic Antioxidants from the Fruits of Three Pouteria Species by Selected Ion Monitoring Liquid Chromatography–Mass Spectrometry
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Reporting liquid chromatography (HPLC) and HPLC/MS: " Analysis of Polyphenolic
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