Effect of postharvest methyl jasmonate treatment on fatty acid composition and phenolic acid content in olive fruits during storage.

BACKGROUND: The nutritional effects of both table olives and olive oil are attributed not only to their fatty acids but also to antioxidant phenolics such as phenolic acids. Delays in oil processing usually result in undesirable oxidation and hydrolysis processes leading to formation of free fatty acids. These alterations create the need to process oil immediately after olive harvest. However, phenolic content decreases drastically during olive storage resulting in lower quality oil. In the present study we propose postharvest methyl jasmonate treatment as a mean to avoid changes in fatty acid composition and losses of phenolic acids during olive storage. RESULTS: Contents of fatty acids and phenolic acids were estimated in methyl jasmonate treated olives throughout 30-day storage, as compared with those of untreated olives. Significant decreases of saturated fatty acids were observed in treated samples whereas increases of oleic, linoleic and linolenic acids were respectively measured (i.e. from 50.8% to 64.5%, from 7.2% to 9.1% and from 1.5% to 9.3%). Also, phenolic acid contents increased significantly in treated olives. Particularly, increases of gallic acid from 1.35 to 6.29 mg kg-1 , chlorogenic acid from 9.18 to 16.21 mg kg-1 , vanillic acid from 9.61 to 16.99 mg kg-1 , caffeic acid from 5.12 to 12.55 mg kg-1 , p-coumaric acid from 0.96 to 5.31 mg kg-1 and ferulic acid from 4.05 to 10.43 mg kg-1 were obtained. CONCLUSION: Methyl jasmonate treatment is proposed as an alternative postharvest technique to traditional methods to guarantee olive oil quality when oil processing is delayed and olive fruits have to necessarily to be stored. © 2016 Society of Chemical Industry.

A Phenolic Extract Obtained from Methyl Jasmonate-Treated Strawberries Enhances Apoptosis in a Human Cervical Cancer Cell Line.

In the present study, we evaluated the effect of methyl jasmonate (MeJA) treatment on strawberry phenolic composition. Strawberry extracts contain a mixture of phenolic compounds possessing several biological properties. We demonstrated that these extracts were more effective in inducing apoptosis in HeLa cells compared to phenolic preparations derived from untreated strawberries. Treatment of strawberries with 0.5% MeJA resulted in increased polyphenols content (from 7.4 to 8.6 mM quercetin equivalents) and antioxidant properties (from 3.9 to 4.6 mM quercetin equivalents). The identification and quantification of phenolic compounds by liquid chromatography-mass spectrometry in the strawberry extracts showed that cyanidin glucoside, pelargonidin glucoside, and ellagic glucoside acid were significantly higher in strawberries treated with MeJA. Phenolic extracts from MeJA-treated strawberries significantly decreased the cell viability in HeLa cells, compared to extracts derived from untreated fruits. We hypothesized that the enhanced apoptotic activity of MeJA-treated strawberries was due to a synergistic or additive effect of different phenolic compounds present in the extract, rather than the activity of a single molecule.

New Procedure to Obtain Polyphenol-Enriched Grapes Based on the Use of Chemical Elicitors.

The effect of the postharvest treatment of methyl jasmonate enantiomers in conjunction with ethanol on bioformation of resveratrol and quercetin glycosides in grapes was evaluated. The antioxidant activity of treated grape extracts as compared with untreated extracts was also assayed. Exogenous (-)-methyl jasmonate in combination with ethanol induced a significant increase in the levels of resveratrol (from 27 to 39 µg g(-1)), quercetin-3-O-glucoside (from 59 to 136 µg g(-1)), quercetin-3-O-galactoside (from 398 to 807 µg g(-1)) and quercetin-3-O-rutinoside (from 23 to 43 µg g(-1)). (+)-Methyl jasmonate with ethanol also resulted in increase of quercetin-3-O-glucoside and quercetin-3-O-rutinoside. However, no (+)-methyl jasmonate effect was observed for resveratrol and quercetin-3-O-galactoside. Both (-)- and (+)-methyl jasmonate treatments provided with extracts with higher antioxidant activity. From the results found in the present work postharvest treatment with (-)-methyl jasmonate in conjunction with ethanol is proposed as a mean to obtain polyphenol-enriched grape extracts with improved antioxidant properties. The procedure here developed is proposed as a mean to obtain functional grapes. Extracts obtained from grapes treated with (-)-methyl jasmonate with ethanol can be particularly useful for industry due to their high antioxidant capacity.

Cancer-Related Constituents of Strawberry Jam as Compared with Fresh Fruit.

The health awareness recently shown by consumers has led to a demand for health beneficial products. In particular, researchers are currently focusing their studies on the search for foods for cancer prevention activity. In the present work, we study comparatively the effect of two different processing methods on the contents of phenolic compounds (i.e., ellagic acid, myricetin, quercetin and kaempferol) with antioxidant and antitumor properties in strawberry jams. In turn, the results obtained were compared with those of unprocessed fruit. Additionally carcinogenic heat-induced compounds formed by the two jam making methods were evaluated. Decreases of total ellagic acid from 138.4 µg/g to 86.5 µg/g were measured in jam as compared with the intact fruit. Even higher losses of up to 90% of total flavonols were found in strawberry after the jam-making process. A comparison between the two processing methods proved shorter heating periods (around 60 min) even at temperatures as high as 100 °C enabled losses of antioxidant phenolics to be minimized. Carcinogenic heat-induced volatile compounds, mainly Maillard reaction products, were formed as a result of thermal treatment during jam processing. However, shorter heating periods also helped reduce the formation of these harmful compounds. These results are deeply discussed. From a practical standpoint, the processing conditions here proposed can be used by industry to obtain strawberry jam with higher content of antioxidant flavonoids and, at the same time, reduced amounts of carcinogenic compounds.

Enhancement of nutritionally significant constituents of black currant seeds by chemical elicitor application.

Black currant seeds are obtained as a residue during juice production. Black currant seed oil contains high amounts of nutritionally desirable constituents such as γ-linolenic acid (GLA), α-linolenic acid (ALA) and stearidonic acid (SA), as well as certain phenolic acids, which act as natural antioxidants. Fatty acids and phenolic acids of seeds from black currant cultivars after elicitation with methyl jasmonate (MJ) were examined. GLA contents around 25% with respect to total fatty acid content were measured in seeds after pre-harvest treatment of black currants with 0.02mM MJ in 0.05% Tween-20. High GLA samples also exhibited high SA content (higher than 10% with respect to total fatty acid content); however, ALA dropped (from 16% to 10%). High GLA content seeds also showed increased contents of gallic, caffeic, p-coumaric and ferulic acids. In particular, seeds from 0.02mM MJ treated Ben Hope black currants exerted contents of gallic, caffeic, p-coumaric and ferulic acids of 201.4, 125.9, 201.3 and 112.5µgg(-1)vs 124.3, 58.6, 165.4 and 95.8µgg(-1) measured in seeds from untreated Ben Hope black currants. Comparable results were obtained for Ben Alder and Ben Gairn berries. Chemical elicitation with 0.02 MJ is proposed as an industrial practice in such a way that, after consideration of quality issues, it would be obtained high added value black currant seeds.

In vitro fermentation of juçara pulp (Euterpe edulis) by human colonic microbiota.

This study was carried out to investigate the potential fermentation properties of juçara pulp, using pH-controlled anaerobic batch cultures reflective of the distal region of the human large intestine. Effects upon major groups of the microbiota were monitored over 24h incubations by fluorescence in situ hybridisation (FISH). Short-chain fatty acids (SCFA) were measured by HPLC. Phenolic compounds, during an in vitro simulated digestion and fermentation, were also analysed. Juçara pulp can modulate the intestinal microbiota in vitro, promoting changes in the relevant microbial populations and shifts in the production of SCFA. Fermentation of juçara pulp resulted in a significant increase in numbers of bifidobacteria after a 24h fermentation compared to a negative control. After in vitro digestion, 46% of total phenolic content still remained. This is the first study reporting the potential prebiotic effect of juçara pulp; however, human studies are necessary to prove its efficacy.

Accumulation of anthocyanins and flavonols in black currants (Ribes nigrum L.) by pre-harvest methyl jasmonate treatments.

BACKGROUND: Chemical elicitation is one of the most effective methods currently used to enrich plant foods in bioactive compounds. Methyl jasmonate (MJ) has been described as a very useful elicitor of some plant compounds, polyphenols among them. The objective of this study was to determine the effects of pre-harvest MJ application on the increase in the main flavonoids and the antioxidant properties of black currant (Ribes nigrum) cultivars. RESULTS: Significant enhancement of individual and total anthocyanins was measured after elicitation with MJ, particularly when a concentration of 0.2 mmol L(-1) was used. Total anthocyanins increased from 28288.74 ± 253.65 to 43561.08 ± 145.87 mg kg(-1) in Ben Hope black currants after elicitation with 0.2 mmol L(-1) MJ. Similarly, an increase from 35986.04 ± 287.98 to 41320.22 ± 109.38 mg kg(-1) was estimated in Ben Alder cultivar. Black currant flavonols were not individually affected by the treatment; however, total flavonols increased from 3115.21 ± 12.11 to 3268.41 ± 8.91 mg kg(-1) in Ben Hope and from 3016.38 ± 10.07 to 3110.95 ± 8.57 mg kg(-1) in Ben Alder. Antioxidant properties of black currants as measured by DPPH and ABTS assays improved proportionally to the increase in flavonoid content after MJ elicitation. CONCLUSION: Pre-harvest elicitation with MJ is proposed as a useful tool to enhance contents of anthocyanins and flavonols as well as free radical-scavenging activity of black currants. The functional black currants obtained here can be interesting for industry, for consumption as fresh fruits and for production of juice and jam. © 2015 Society of Chemical Industry.

Supercritical fluid extraction of grape seeds: extract chemical composition, antioxidant activity and inhibition of nitrite production in LPS-stimulated Raw 264.7 cells.

Grape by-products are a rich source of bioactive compounds having broad medicinal properties, but are usually wasted from juice/wine processing industries. The present study investigates the use of supercritical fluid extraction (SFE) for obtaining an extract rich in bioactive compounds. First, some variables involved in the extraction were applied. SFE conditions were selected based on the oil mass yield, fatty acid profile and total phenolic composition. As a result, 40 °C and 300 bar were selected as operational conditions. The phenolic composition of the grape seed oil was determined using LC-DAD. The antioxidant activity was determined by ABTS and DPPH assays. For the anti-inflammatory activity the inhibition of nitrite production was assessed. The grape seed oil extracted was rich in phenolic compounds and fatty acids with significant antioxidant and anti-inflammatory activities. From these results, added economic value to this agroindustrial residue is proposed using environmentally friendly techniques.

Chemical composition and antioxidant activity of seven cultivars of guava (Psidium guajava) fruits.

The antioxidant activity and identification of phenolic compounds of seven edible guava (Psidium guajava) cultivars that varied in colour from white to pink were examined. In the DPPH assay all four pink-pulp guavas (Barbie Pink, Homestead, Sardina 1, Sardina 2) included in the study showed higher activity than the white pulp cultivars (Yen 2 and Sayla) and less than the red pulp guava cultivar (Thai Maroon). In the ABTS(+) assay this trend was the same up to 20 min, but from 20 to 40 min Barbie Pink showed lower activity than the white guavas. Twenty-one compounds were characterised in the cultivars, and ten of them are reported for the first time in this fruit. Principle component analysis was performed to identify differences in chemistry among these cultivars. Our results suggest that the antioxidant activity and phytochemical composition of P. guajava vary significantly according to the cultivar and pulp colour.

Phenylalanine ammonia-lyase, flavanone 3ß-hydroxylase and flavonol synthase enzyme activity by a new in vitro assay method in berry fruits.

An HPLC method for the determination of phenylalanine ammonia-lyase, flavanone 3ß-hydroxylase and flavonol synthase enzyme activity is proposed. This method is based on the determination of the compounds produced and consumed on the enzymatic reaction in just one chromatographic analysis. Optimisation of the method considered kinetic studies to establish the incubation time to perform the assay. The method here described proved to be an interesting approach to measure the activities of the three enzymes simultaneously increasing the rapidity, selectivity and sensitivity over other exiting methods. The enzyme activity method developed was applied to strawberry, raspberry, blackberry, redcurrant and blackcurrant fruits.

Isolation of the four methyl jasmonate stereoisomers and their effects on selected chiral volatile compounds in red raspberries.

The four stereoisomers present in a commercial sample of methyl jasmonate (MJ) were isolated at semi-preparative scale by HPLC, using a permethylated ß-cyclodextrin column. This allowed the baseline resolution and collection of both major (methyl jasmonates) and minor (epi-methyl jasmonates) stereoisomers. When 1.5 mL of a 5mg per mL MJ solution were injected, isolated amounts were 3.56 mg for (-) and (+)-methyl jasmonates, with respective purities of 96.1% and 99.9%, and 0.18 mg for (-)- and (+)-epi-methyl jasmonates, with 98.6% and 91.6% respective purities. The post-harvest treatment of red raspberry fruits with the pure methyl jasmonate stereoisomers isolated proved that (-)-epi-MJ either promotes the bioformation of (+)-limonene or inhibits that of (-)-limonene to a greater extent than the other three MJ stereoisomers, while the biosynthesis of the (+)-enantiomer of α-ionone is favoured equally, whichever MJ stereoisomer used. The results obtained in the present study might be used to obtain food products with improved sensory characteristics.

Phenolic-rich extract from the Costa Rican guava (Psidium friedrichsthalianum) pulp with antioxidant and anti-inflammatory activity. Potential for COPD therapy.

The potential therapeutic effects of Costa Rican guava (Psidium friedrichsthalianum) extracts for chronic obstructive pulmonary disease were examined. The ethyl acetate fraction displayed the highest antioxidant activity, as compared to the hexane, chloroform, and n-butanol fractions, as well as the crude extract. This fraction was evaluated for its anti-inflammatory activity response relationship against interleukin-8 (IL-8) and inhibition of matrix metalloproteinase-1 (MMP-1) expression before and after treatment with cigarette smoke. The ethyl acetate fraction exhibited inhibitory activity against IL-8 production and MMP-1 expression, showing the most potent inhibitory activities in both assays at 100µg/mL, and nine compounds (1-9) were found. Phenolic compounds 1-O-trans-cinnamoyl-ß-d-glucopyranose (2), ellagic acid (3), myricetin (4), quercitrin (7), and quercetin (9) were identified using standard compounds or literature reports from related species. Compounds 1, 5, 6, and 8 were tentatively identified as 1,5-dimethyl citrate (1), sinapic aldehyde 4-O-ß-d-glucopyranose (5), 3,3',4-tri-O-methylellagic acid-4'-O-d-glucopyranoside (6), and 1,3-O-diferuloylglycerol (8), All nine compounds are reported for the first time in Costa Rican guava.

Antioxidant and metabolite profiling of North American and neotropical blueberries using LC-TOF-MS and multivariate analyses.

There are many neotropical blueberries, and recent studies have shown that some have even stronger antioxidant activity than the well-known edible North American blueberries. Antioxidant marker compounds were predicted by applying multivariate statistics to data from LC-TOF-MS analysis and antioxidant assays of 3 North American blueberry species (Vaccinium corymbosum, Vaccinium angustifolium, and a defined mixture of Vaccinium virgatum with V. corymbosum) and 12 neotropical blueberry species (Anthopterus wardii, Cavendishia grandifolia, Cavendishia isernii, Ceratostema silvicola, Disterigma rimbachii, Macleania coccoloboides, Macleania cordifolia, Macleania rupestris, Satyria boliviana, Sphyrospermum buxifolium, Sphyrospermum cordifolium, and Sphyrospermum ellipticum). Fourteen antioxidant markers were detected, and 12 of these, including 7 anthocyanins, 3 flavonols, 1 hydroxycinnamic acid, and 1 iridoid glycoside, were identified. This application of multivariate analysis to bioactivity and mass data can be used for identification of pharmacologically active natural products and may help to determine which neotropical blueberry species will be prioritized for agricultural development. Also, the compositional differences between North American and neotropical blueberries were determined by chemometric analysis, and 44 marker compounds including 16 anthocyanins, 15 flavonoids, 7 hydroxycinnamic acid derivatives, 5 triterpene glycosides, and 1 iridoid glycoside were identified.

Edible Myrciaria vexator fruits: bioactive phenolics for potential COPD therapy.

The edible fruits of Myrciaria vexator McVaugh (Myrtaceae), from northern South America, are eaten in certain locales, either fresh or processed into jellies and drinks. Activity-guided fractionation of M. vexator resulted in identification of ellagic acid (1), cyanidin-3-O-glucoside (2), delphinidin-3-O-glucoside (3), 2-O-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxyphenylacetic acid (4), and jaboticabin (5), and latter two compounds are being reported for the first time in this species. Ellagic acid was further examined, and found to inhibit cigarette smoke extract induced MMP-1 expression in vitro, and may be of significance in the treatment of chronic obstructive pulmonary (COPD). Other compounds identified for the first time from M. vexator include cyanidin-3-O-galactoside (6), cyanidin-3-O-arabinoside (7), cyanidin-3-O-rutionoside (8), petunidin (9), peonidin-3-O-galactoside (10) malvidin (11), hyperoside (12), querecetin-3-O-glucoside (13), and guajaverin (14), methyl protocatechuate (15), and protocatechuic acid (16).

Antioxidants of therapeutic relevance in COPD from the neotropical blueberry Anthopterus wardii.

Four flavone C-glycosides, isoorientin (1), orientin (2), vitexin (3), and isovitexin (4), were isolated from the neotropical blueberry of Anthopterus wardii, a so-called "superfruit", using antioxidant activity-guided fractionation. A dose-response relationship of compounds 1-4 was determined for their anti-inflammatory activity against interleukin-8 (IL-8) and for the inhibition of matrix metalloproteinase-1 (MMP-1) expression, an inflammatory marker for chronic obstructive pulmonary disease. The four flavone C-glycosides exhibited inhibitory activity against IL-8 production and MMP-1 expression, with compounds 1, 3, and 4 having the most potent inhibitory activities in both assays at 100 µg/ml. The structures of compounds 1-4 were determined by spectroscopic methods. These flavone C-glycosides are reported for the first time in the Anthopterus genus.

Anthocyanins from Eugenia brasiliensis edible fruits as potential therapeutics for COPD treatment.

Nine anthocyanins (1-9) from the edible fruits of Eugenia brasiliensis were identified by HPLC-PDA and LC-MS, and seven of these are described for the first time in this Brazilian fruit. Two of the major anthocyanins, delphinidin (8) and cyanidin (9), were studied for their inhibitory activity against chemokine interleukin-8 (IL-8) production before and after cigarette smoke extract (CSE) treatment of cells. In non-treated cells the amount of IL-8 was unchanged following treatment with cyanidin and delphinidin in concentrations 0.1-10 µM. Both delphinidin (8) and cyanidin (9) decreased the production of IL-8 in treated cells, at 1 and 10 µM, respectively. Delphinidin (8) demonstrated IL-8 inhibition in the CSE treated cells in a dose-dependent manner.

Edible neotropical blueberries: antioxidant and compositional fingerprint analysis.

Edible blueberry species are well recognized for their potential health benefits. Ericaceae fruits including the North American highbush blueberry (Vaccinium corymbosum L.) and five less common edible blueberry relatives from the New World tropics, Anthopterus wardii Ball, Cavendishia grandifolia Hoerold, Macleania coccoloboides A. C. Smith, Sphyrospermum buxifolium Poeppig & Endlicher, and Sphyrospermum cordifolium Benth, were investigated for their antioxidant properties and phenolic profiles. The neotropical berries C. grandifolia and A. wardii exhibited significantly higher 1,1-diphenyl-2-picrylhydrazyl (DPPH(•)) and 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS(• +)) free radical scavenging and iron chelation activities than V. corymbosum. Total phenolic content and high-performance liquid chromatography with photodiode array detection (HPLC-PDA) compositional fingerprint analyses were also carried out. Significant correlations were observed among total phenolic contents, DPPH(•) and ABTS(• +) scavenging, and iron chelation activities. By use of HPLC-PDA, the phenolic constituents in the berries were identified as chlorogenic acid, p-coumaric acid, hyperoside, quercetin-3-O-glucoside, isoorientin, isovitexin, orientin and vitexin. Principal component analysis reduced the dimensions of antioxidant and total phenolic data to two components, which accounted for 95% of total variation among the six fruits. Each fruit species formed its own cluster, and therefore the antioxidant profile of each species was shown to be distinct.

Exogenous methyl jasmonate diminishes the formation of lipid-derived compounds in boiled potato (Solanum tuberosum L.).

BACKGROUND: During potato storage the tubers tend to develop off-flavours, mainly due to lipid-derived aldehydes, whose formation is increased after boiling or processing. This may become a problem when boiled or precooked potatoes are used. Methyl jasmonate (MJ) is a phytohormone capable of modifying plant and food composition. The aim of this work was to control the formation of off-flavours in different cultivars of raw potato during storage by MJ treatment. RESULTS: The use of Carbowax 20M as support in MJ emulsion resulted in significantly (P < 0.05) lower levels of lipid-derived compounds than the use of lanolin. Levels of the lipid-derived aldehydes propanal, hep-2-enal, nonanal, oct-2-enal and hexanal, although dependent on variety, generally decreased significantly (P < 0.05) after treatment with MJ/Carbowax 20M emulsion. Sugar-derived compounds such as pyridine and furfural, however, were not affected by this treatment. CONCLUSION: Treatment with MJ/Carbowax 20M can be used to diminish the formation of off-flavours in boiled potato. However, this treatment is not useful to avoid the sweetening caused by sugar-derived products. Additional advantages of exogenous MJ are a delay in the appearance of sprouting and aging and hence prolongation of the storage life of potato tubers.

Impact of postharvest methyl jasmonate treatment on the volatile composition and flavonol content of strawberries.

BACKGROUND: Although strawberry aroma is very complex, certain compounds have been described as main contributors, i.e. furanones, aldehydes, alcohols, sulfur compounds and particularly methyl and ethyl esters. In addition, strawberries possess potent antioxidant activity because of their high content of phenolic compounds. Among them, flavonols are highlighted as important antioxidant compounds in strawberry. The objective of this study was to assess the effect of methyl jasmonate (MJ) on the composition of the major contributors to aroma and on the content of certain flavonols in strawberry fruits. RESULTS: The levels of all studied volatile compounds were significantly affected by MJ treatment, though the individual effect differed according to the specific compound considered. Most of them increased significantly (P < 0.05), except methyl butanoate, which always showed higher levels in untreated strawberries. In contrast to aroma compounds, the change in the concentration of flavonols (i.e. myricetin, quercetin and kaempferol) was not significant in MJ-treated strawberries. Considering the health-promoting activity of these compounds, further investigations on the experimental conditions related to the treatment are required to control flavonol bioformation by means of MJ. CONCLUSION: The exogenous application of MJ vapour to strawberry enhances, in general, the production of the most relevant aroma-active compounds. On the contrary, MJ treatment does not appear to influence the levels of myricetin, quercetin and kaempferol. Thus postharvest MJ treatment is proposed as an approach to obtain improved strawberry fruits in terms of sensory quality and health-promoting properties.

Enantiomeric analysis of chiral compounds in irradiated foods using multidimensional gas chromatography.

The usefulness of both solid phase microextraction (SPME) and multidimensional gas chromatography (MDGC) coupled to mass spectrometry (MS) to detect chiral compounds in irradiated cheese was evaluated. The enantiomeric resolution of relevant chiral aroma compound was achieved by analyzing the extracts obtained from SPME by means of a permethylated beta-CD stationary phase as the main column of the multidimensional system to separate specific selected cuts containing components unresolved in the first dimension. The proposed procedure allowed to determine, in less than 90 min, that no significant variations had been produced in the stereoisomeric distribution of limonene, 3-hydroxybutanone, and 2,3-butanediol in cheese when applying irradiation doses ranging from 0 to 8 kGy.