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Aim of study: In a social context of increasing concern about healthy diets, the development of new varieties with enhanced content in nutraceutical compounds is an important objective of the fruit breeding programs currently developed. In this sense, apricot is a fruit crop very appreciated by consumers worldwide due to its organoleptic characteristics, but also plays an important role in human nutrition due to its content of phytocompounds as sugars, organic acids, vitamins and polyphenols. Area of study: The identification of sources of variation for these traits could be useful for apricot breeding worldwide. Material and methods: New selections from the apricot breeding program carried out at the Instituto Valenciano de Investigaciones Agrarias (IVIA, Spain) and traditional varieties have been analysed aimed at identifying sources of genetic variation for fruit quality. For this purpose, sugar content, organic acids and ascorbic acid were studied during three crop years. Main results: Results revealed sucrose and glucose as the major sugars, malic and citric acid as the main organic acids, and diverse ascorbic acid content among the cultivars studied. Research highlights: Some accessions point as potential sources to increase fruit quality. In addition, the study showed that apricot peel is an excellent source of nutraceutical compounds. Moreover, this study opens up new possibilities to study the genetic control of these traits in apricot in the future.

BACKGROUND The susceptibility to chilling injury and quality changes of 'Tango' mandarins stored at different temperatures was evaluated in fruit grown at two locations in Andalusia (Spain) and grafted on Carrizo Citrange or FA5 rootstock. The peel disorders were also characterized by a microstructural study. RESULTS Fruit developed chilling injuries, manifested as pitting lesions affecting the equatorial area of the fruit stored at 1 °C or 5 °C; fruit growing on FA5 rootstock showed a slightly lower incidence. The microstructural study revealed that only the upper layers of flavedo were affected in the damaged fruit, the epidermal and hypodermal tissues being dramatically collapsed. Although the fruit was prone to accumulate ethanol, especially after the shelf life that followed the different periods of cold storage, the ethanol did not compromise the overall flavor. CONCLUSIONS Storage of 'Tango' fruit was limited by chilling injuries when stored at 1 °C or 5 °C for more than 20 days. Moreover, at these temperatures, the fruit was prone to accumulate ethanol and develop off flavors. At 9° C, the fruit could be stored for 30 days without compromising external or internal quality. Growing location and rootstock influenced some quality attributes at harvest but not during storage. © 2020 Society of Chemical Industry.

Juices from nine new late-season triploid mandarins (Tania-46 (1), Tania-47 (2), Omet (3), Albir (4), Tania-48 (5), Tania-43 (6), Tania-44 (7), Coral (8), and Matiz (9), and from their parents were analyzed for mainly internal quality attributes, vitamin C, total phenolics, flavonoids, phenolic, and organic acids. Antioxidant activity was measured by three methods, the DPPH free radical-scavenging assay, ferric reducing antioxidant power (FRAP) test, and ABTS analysis. All the new hybrids exhibited high internal and nutritional quality which may be considerate rich sources of phytochemicals. Among the nine varieties, Tania-48 hybrid was shown to be the richest in vitamin C, flavanones (hesperidin, eriocitrin, and neoeriocitrin), polymethoxyflavones, and malic and succinic acids. Furthermore, the juice of this new triploid hybrid displayed high antioxidant capacity which may make it important for human diet as a source of health-promoting components. On the other hand, Tania-44, Tania-48, and Tania-43 fruit juices exhibited greater content of eriocitrin and neoeriocitrin than the others.

There is an increasing interest in polyphenols, plant secondary metabolites, in terms of fruit quality and diet, mainly due to their antioxidant effect. However, the identification of key gene enzymes and their roles in the phenylpropanoid pathway in temperate fruits species remains uncertain. Apricot (Prunus armeniaca) is a Mediterranean fruit with high diversity and fruit quality properties, being an excellent source of polyphenol compounds. For a better understanding of the phenolic pathway in these fruits, we selected a set of accessions with genetic-based differences in phenolic compounds accumulation. HPLC analysis of the main phenolic compounds and transcriptional analysis of the genes involved in key steps of the polyphenol network were carried out. Phenylalanine ammonia-lyase (PAL), dihydroflavonol-4-reductase (DFR) and flavonol synthase (FLS) were the key enzymes selected. Orthologous of the genes involved in transcription of these enzymes were identified in apricot: ParPAL1, ParPAL2, ParDFR, ParFLS1 and ParFLS2. Transcriptional data of the genes involved in those critical points and their relationships with the polyphenol compounds were analyzed. Higher expression of ParDFR and ParPAL2 has been associated with red-blushed accessions. Differences in expression between paralogues could be related to the presence of a BOXCOREDCPAL cis-acting element related to the genes involved in anthocyanin synthesis ParFLS2, ParDFR and ParPAL2.

The physico-chemical quality parameters (external and internal color, firmness, acidity, total soluble solids, anthocyanins, sugars, hydroxycinnamic acids and flavanones) of ‘Moro’ and ‘Tarocco Rosso’ blood oranges grafted onto eight different rootstocks at three harvest time were studied. The rootstocks were ‘Carrizo’, ‘C-35’, ‘Cleopatra’ mandarin, ‘Citrus volkameriana’, ‘Citrus macrophylla’, ‘Swingle’ citrumelo, ‘Forner-Alcaide 5’ and ‘Forner-Alcaide 13’. All studied parameters were highly rootstock/scion-dependent and showed changes throughout harvest. The content of the main anthocyanins revealed their relation with internal fruit color in both cultivars. The rootstocks that led to fruit with the lowest anthocyanins displayed the least sucrose content. The differences detected in the amount of hydroxycinnamic acids (chlorogenic, ferulic and sinapic) and flavanones (hesperidin, narirutin and didymin) related to anthocyanins content, explained phenylpropanoid pathway.

Citrus rootstocks are a relevant tree part that contributes to crops adapting to biotic and abiotic conditions, it becoming a key factor to face the current era of climate change. Although the emphasis of most studies on rootstocks has been placed on the yield and optimization of the citrus fruit grown in different environments, other studies have paid attention to the effect of rootstock on fruit quality. Hence, the quality of citrus fruit is becoming increasingly more relevant as consumers demand high internal and external qualities to eat citrus fruit fresh. To better understand how rootstock influences citrus fruit quality, the literature that focuses on physico-chemical parameters, nutritional compounds and physiological disorders has been revised. This review points out the influence that the external aspects surrounding plants has on fruit quality, such as the rootstock/scion interaction, the water uptake capacity of roots, the modification of the photosynthetic rate or availability of nutrient minerals.

[EN] In this study, the effect of two hot air drying conditions (40 degrees C for 23 h and 60 degrees C for 9 h) on the content, antioxidant activity, microstructure, and luminescence properties of persimmon carotenoids in three ripening stages was studied. Based on the results from total carotenoids content and HPLC analysis, the carotenoid's content increased with the advance of ripening, highlighting the beta-cryptoxanthin fraction. In addition, drying treatments did not affect the carotenoid content and profile but decreased the antioxidant activity. Microstructural studies showed that the ripening progress and/or drying treatments, led persimmon tissues to lose integrity, allowing the diffusion of carotenoids and their degradation. Photoluminescence measurements evidenced the synthesis of beta-cryptoxanthin during the fruit ripening. After drying, a new emitting specie at 340 nm was attributed to the carotenoid's isomerisation while the emission at 500 nm experienced a shift that was related to the formation of thermal degradation products. Both facts could explain the loss of antioxidant activity in persimmon submitted to drying treatments. In this sense, photoluminescence, in combination with spectro-photometric, chromatographic and structural techniques, helps to understand the phenomena caused by both, ripening and drying treatments, in the persimmon's carotenoids fraction., The authors thank the Ministerio de Ciencia, Innovacion y Universidades for the financial support given throughout Project RTA201700045-C02-02. They would also like to thank Phillip Bentley for assistance in correcting the manuscript's English.

'Tango' mandarin is becoming one of the most demanded varieties in the Mediterranean Region. However, no information on the quality of 'Tango' fruit in this citrus area has been reported. In this study, the physico-chemical, nutritional and sensorial quality of 'Tango' mandarins grafted onto Carrizo Citrange and FA5 rootstocks from two locations (Sevilla and Huelva) was evaluated by harvest season. The fruit from Sevilla exhibited lower levels of acids and sugars than those from Huelva, which was associated with a higher sandy soil percentage in the Huelva orchard. In both orchards, the FA5-produced fruit had higher sugars and acids. Flavonoids were affected mainly by location, and the Huelva fruit exhibited the highest levels. The highest vitamin C was for the FA5 fruit. The decreased antioxidant capacity observed throughout the harvest season was related to reduced vitamin C. The sensorial evaluation corroborated changes in the quality parameters.

Apricot (Prunus armeniaca L.) species is one of the most important Mediterranean fruits. The fruits are important in the diet of Asian and Mediterranean countries in which the apricot is used as fresh and dried fruit, being an important source of nutrients. Despite of the amount of genetic resources and diversity studies available into the species, there are a few studies focused on fruit quality. Among the different compounds of fruit quality, polyphenols are classified as the most abundant antioxidants in nature, being important as a source of health benefits as well as a potential source of natural products for the food industry. The important role of polyphenols in human nutrition, outline these compounds as the most relevant for defining fruit quality. In this study, the polyphenol content on fruits from different apricot varieties included elite cultivars and hybrids from the IVIA breeding program have been compared for identifying the genotypes with relevant contribution to fruit quality. The most important compounds obtained in terms of quantity were: phenolic acids and flavonoids. Results identified the PPV resistant cultivar ‘Goldrich’ as the best cultivar for increasing the content of antioxidants in the varieties of the breeding program.

Pummelos and hybrids, such as grapefruits, have high furanocoumarin and low flavonoid contents. Furanocoumarins interact negatively with certain drugs, while flavonoids are antioxidant compounds with health benefits. To obtain new grapefruit-like varieties with low furanocoumarin and high flavonoid contents, diploid and triploid hybrid populations from crosses between diploid and tetraploid “Clemenules” clementine and diploid “Pink” pummelo were recovered and analyzed. With regard to furanocoumarins, triploids produce less bergapten, bergamottin and 6,7-DHB than diploids. Regarding flavonoids, triploids yielded more eriocitrin, narirutin, hesperidin and neohesperidin than diploids, whereas no differences were observed in neoeriocitrin and naringin. These results indicate that, the strategy to recover triploid hybrids by 4x × 2x crosses is more appropriate than the recovery of diploid hybrids by 2x × 2x crosses for obtaining grapefruit-like varieties of citrus with lower furanocoumarin and higher flavonoid contents.

This study reports the influence of eight rootstocks (&lsquo, Carrizo&rsquo, (CC), &lsquo, C-35&rsquo, (C35) &lsquo, Cleopatra&rsquo, (CL), &lsquo, Volkameriana&rsquo, (VK), &lsquo, Macrophylla&rsquo, (M), &lsquo, Forner-Alcaide 5&rsquo, (FA5), &lsquo, Forner-Alcaide 13&rsquo, (FA13) and &lsquo, Forner-Alcaide V17&rsquo, (V17)) on the physico-chemical and nutritional quality of &lsquo, Clemenules&rsquo, mandarins at three harvest times during two seasons. Fruit quality parameters were influenced by rootstocks, and this effect was mostly harvest time -dependent. External color was overall influenced by rootstocks upon the first harvest. FA13 and C35 induced a breakthrough in color change, while V17 brought about the greatest color increase. CL and V17 initially delayed the fruit maturity index. In the last harvest, while CL had one of the highest maturity indices, V17 exhibited the lowest as acidity was maintained as harvest advanced. The CC and M fruit had the highest and lowest sucrose content, respectively. The highest glucose and fructose contents in fruit were induced by V17, FA5 and CC. The highest citric acid content was displayed by V17 in all the harvests. The FA13, C35 and VK fruit exhibited the highest malic acid content. The effect that rootstock exert on ascorbic acid and flavonoid content depends on the studied season. The results reveal the importance of conducting studies during different seasons to obtain robust results.

Nowadays, consumers demand fresh fruits high in bioactive compounds because of their growing concern for health. Carotenoids are important bioactive compounds present in persimmon fruit and the content of these compounds depends on the cultivar. Before marketing fruit from astringent persimmon cultivars are routinely submitted to astringency removal treatments; however, the effect of this process on flesh carotenoids has not yet been studied in depth. This work aimed to evaluate the effect of the deastringency treatment based on high CO2 concentration on carotenoids content of persimmon fruit. To this end, total and individual carotenoids were determined in four astringent cultivars ('Aizumishirazu-A', 'Hachiya', 'Giombo' and 'Rojo Brillante') at harvest and after fruit submitted to CO2-deastringency treatment (95% CO2, 24 h, 20°C, 90% RH). Our results corroborated that the total carotenoids content depends on the cultivar, the highest content at harvest being detected in 'Hachiya' and 'Aizumishirazu-A'. The main carotenoids present in the flesh of persimmons were β-cryptoxanthin, lutein, violoxanthin, zeaxanthin, and β-carotene; in the four studied cultivars, β-cryptoxanthin was the predominant carotenoid. The CO2-deastringency treatment did not affect the total carotenoids content of 'Rojo Brillante' and 'Hachiya'. However, CO2 treatment resulted in increased carotenoids content in 'Aizumishirazu-A' and 'Giombo', and lutein and β-cryptoxanthin were the carotenoids that most markedly increased after astringency removal.

International audience; We describe the synthesis of 26 compounds, small polycerasoidol analogs, that are Lipinski’s rule-of-five compliant. In order to confirm key structural features to activate PPARα and/or PPARγ, we have adopted structural modifications in the following parts: (i) the benzopyran core (hydrophobic nucleus) by benzopyran-4-one, dihydrobenzopyran or benzopyran-4-ol; (ii) the side chain at 2-position by shortening to C3, C4 and C5-carbons versus C-9-carbons of polycerasoidol; (iii) the carboxylic group (polar head) by oxygenated groups (hydroxyl, acetoxy, epoxide, ester, aldehyde) or non-oxygenated motifs (allyl and alkyl). Benzopyran-4-ones 6, 12, 13 and 17 as well as dihydrobenzopyrans 22, 24 and 25 were able to activate hPPARα, whereas benzopyran-4-one (7) with C5-carbons in the side chain exhibited hPPARγ agonism. According to our previous docking studies, SAR confirm that the hydrophobic nucleus (benzopyran-4-one or dihydrobenzopyran) is essential to activate PPARα and/or PPARγ, and the flexible linker (side alkyl chain) should containg at least C5-carbon atoms to activate PPARγ. By contrast, the polar head (“carboxylic group”) tolerated several oxygenated groups but also non-oxygenated motifs. Taking into account these key structural features, small polycerasoidol analogs might provide potential active molecules useful in the treatment of dyslipidemia and/or type 2 diabetes.

[EN] Citrus is a wide genus in which most of the cultivated species and cultivars are natural parthenocarpic mutants or hybrids (i.e. orange, mandarin, tangerine, grapefruit). The autonomous increase in GA(1) ovary concentration during anthesis was suggested as being the stimulus responsible for parthenocarpy in Citrus regardless of the species. To determine the exact GA-role in parthenocarpic fruit set, the following hypothesis was tested: GA triggers and maintains cell division in ovary walls causing fruit set. Obligate and facultative parthenocarpic Citrus species were used as a model system because obligate parthenocarpic Citrus sp (i.e. Citrus unshiu) have higher GA levels and better natural parthenocarpic fruit set compared to other facultative parthenocarpic Citrus (i.e. Citrus clementina). The autonomous activation of GA synthesis in C. unshiu ovary preceded cell division and CYCA1.1 up regulation (a G2-stage cell cycle regulator) at anthesis setting a high proportion of fruits, whereas C. clementina lacked this GA-biosynthesis and CYCA1.1 up-regulation failing in fruit set. In situ hybridization experiments revealed a tissue-specific expression of GA20ox2 only in the dividing tissues of the pericarp. Furthermore, CYCA1.1 expression correlated endogenous GA(1) content with GA(3) treatment, which stimulated cell division and ovary growth, mostly in C clementina. Instead, paclobutrazol (GA biosynthesis inhibitor) negated cell division and reduced fruit set. Results suggest that in parthenocarpic citrus the specific GA synthesis in the ovary walls at anthesis triggers cell division and, thus, the necessary ovary growth rate to set fruit. (C) 2016 Elsevier Ireland Ltd. All rights reserved.

[EN] In this work, we study the capacity to biosynthesize gibberellins (GA) of ovules (either fertilised or unfertilised), developing seeds and pericarp from fruitlets and their relation with fruit set capacity. Experiments were performed in adult, 12-year-old trees of seeded (Pineapple) and seedless parthenocarpic (Washington navel) sweet orange [Citrus sinensis L. Osbeck] cultivars. The activity of GA20-, GA3- and GA2-oxidases and gibberellin levels were measured in the ovules and pericarp of fruitlets in different development states. The results indicate that ovules are the main sites of gibberellin synthesis in fruitlets during the post-anthesis period. The most intense GA(1) synthesis-coincident with the highest expression of GA20ox2, GA3ox1 and GA2ox1-was detected in the ovules of the seeded cultivar, probably induced by fecundation and associated with low early fruitlet abscission rates. By contrast, the low activity detected in the sterile cultivar appears to be rather developmentally or constitutively regulated. As a fruitlet develops, the GA(1) concentration is augmented in the pericarp in comparison to ovules or developing seeds, and levels therein did not exhibit noticeable differences between varieties. Furthermore, developing seeds from pineapple had higher GA(1) content than the unfertilised abortive ovules from Washington navel. Taken together, data suggest a main role for this hormone in the control of fruitlet abscission, and also demonstrate a function in seed development., We thank Drs. Isabel Lopez-Diaz and Esther Carrera for the hormone quantification carried out at the Plant Hormone Quantification Service, IBMCP, Valencia, Spain. Thanks are due to Teresa Sabater from the IBMCP, for their help. This work has been supported by two research projects, RTA2013-00024-CO2-01 from INIA (Ministerio de Economia y Competitividad, Spain) and IVIA-5423 from Conselleria de Agricultura (Generalitat Valenciana, Valencia, Spain).

Dual peroxisome proliferator-activated receptor-α/γ (PPARα/γ) agonists regulate both lipid and glucose homeostasis under different metabolic conditions and can exert anti-inflammatory activity. We investigated the potential dual PPARα/γ agonism of prenylated benzopyrans polycerasoidol (1) and polycerasoidin (2) and their derivatives for novel drug development. Nine semisynthetic derivatives were prepared from the natural polycerasoidol (1) and polycerasoidin (2), which were evaluated for PPARα, -γ, -δ and retinoid X receptor-α activity in transactivation assays. Polycerasoidol (1) exhibited potent dual PPARα/γ agonism and low cytotoxicity. Structure–activity relationship studies revealed that a free phenol group at C-6 and a carboxylic acid at C-9′ were key features for dual PPARα/γ agonism activity. Molecular modeling indicated the relevance of these groups for optimal ligand binding to the PPARα and PPARγ domains. In addition, polycerasoidol (1) exhibited a potent anti-inflammatory effect by inhibiting mononuclear leukocyte adhesion to the dysfunctional endothelium in a concentration-dependent manner via RXRα/PPARγ interactions. Therefore, polycerasoidol (1) can be considered a hit-to-lead molecule for the further development of novel dual PPARα/γ agonists capable of preventing cardiovascular events associated with metabolic disorders. Fil: Bermejo, Almudena. Universidad de Valencia; España Fil: Collado, Aida. Universidad de Valencia; España Fil: Barrachina, Isabel. Universidad de Valencia; España Fil: Marqués, Patrice. Universidad de Valencia; España Fil: El Aouad, Noureddine. Universidad de Valencia; España Fil: Franck, Xavier. Université de Rouen; Francia Fil: Garibotto, Francisco Matías. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina Fil: Dacquet, Catherine. Institut de Recherches Servier; Francia Fil: Caignard, Daniel H.. Institut de Recherches Servier; Francia Fil: Suvire, Fernando Daniel. Universidad Nacional de San Luis; Argentina Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina Fil: Piqueras, Laura. Universidad de Valencia; España Fil: Figadère, Bruno. Université Paris Sud; Francia Fil: Sanz, María-Jesús. Universidad de Valencia; España Fil: Cabedo, Nuria. Universidad de Valencia; España Fil: Cortes, Diego. Universidad de Valencia; España

[EN] Gibberellins (GA) and auxin (indole-3-acetic acid, IAA) are considered the main compounds involved in the induction of fruit set. Citrus trees flower profusely but exhibit dramatically low fruit set rates and, in particular, seeded orange cultivars also require pollination for fruit to adequately set. Consequently, they represent an excellent model to investigate the interactions between both hormones and their effect on fruit set and development. Unpollinated ovaries from 'Pineapple' sweet orange trees were treated with IAA and pollinated ones with TIBA (2,3,5-triiodobenzoic acid, inhibitor of auxin transport), and changes in ovaries were registered shortly after the treatments. The highest IAA levels were found in unpollinated ovaries treated with auxin (twofold increase compared to pollinated ones), and the lowest corresponded to pollinated ones supplemented with TIBA (30% reduction). GA content also differed substantially among samples. In general, expression of the GA-biosynthetic gene GA20ox2 in the ovule and pericarp paralleled the changes in GA(20) content in both tissues, and also expression of GA3ox1 and GA(1) content but only in the ovule. The levels of these GA in unpollinated ovaries were promoted in response to exogenous IAA, whereas expression of the GA-inactivation gene GA2ox1 and the concentration of the GA-catabolite GA(8) were reduced by this treatment. Significantly, treatments with GA(3) or IAA to unpollinated ovaries recovered fruit set to the level reached by free pollinated ones. Our study demonstrates that IAA alters GA metabolism in citrus leading to marked changes in the active GA(1) levels in ovules and pericarp, mainly through the regulation of GA-biosynthetic genes and the inhibition of the catabolic pathway., We thank Drs. Isabel Lopez-Diaz and Esther Carrera for the hormone quantification carried out at the Plant Hormone Quantification Service, IBMCP, Valencia, Spain. Thanks are due to Teresa Sabater from the IBMCP, for her help. This work has been supported by two research projects, RTA2013-00024-CO2-01 from INIA (Ministerio de Economia y Competitividad, Spain) and IVIA-51423 from Conselleria de Agricultura (Generalitat Valenciana, Valencia, Spain).

Traditionally persimmons have been consumed over-ripened to avoid astringency perception. However, the introduction of new technology that removes astringency while preserving fruit firmness has allowed the commercialization of “ready-to-eat crisp” fruits. Several studies have evaluated the nutritional composition of over-ripened persimmons and have claimed that they are a good source of primary and secondary metabolites that are favourable for human health. Yet very little is known about the nutritional composition of persimmons in the “ready-to-eat crisp” stage. In this context, we determined the main nutritional compounds in ten popular persimmon cultivars, including astringent cultivars (“Rojo Brillante”, “Tone Wase”, “Giboshi”, “Kaki Tipo”, “Aizumishirazu-A”, “Giombo”, “Hachiya”) and non-astringent cultivars (“O’gosho”, “Hana Fuyu” and “Jiro”). To this end, fruits were harvested when their texture was firm, and soluble polyphenols content, total antioxidant capacity and main sugars, organic acids and carotenoids were evaluated. In those astringent cultivars at harvest, the changes in nutritional compounds associated with applying deastringency treatment with high CO2 concentration were determined. Our results revealed the main sugars (glucose, fructose and sucrose), organic acids (citric acid, malic acid and succinic) and carotenoids (β-cryptoxanthin, lutein, violoxanthin, zeaxanthin, and β-carotene) present in the flesh of crisp persimmons. At harvest the content of these metabolites vastly varied among cultivars; astringent cultivars showed higher soluble polyphenols and greater antioxidant capacity, and presented higher contents of sugars and organic acids than non-astringent ones. The deastringency treatment applied to astringent cultivars resulted in a drastic loss of soluble polyphenols and total antioxidant capacity, and induced changes in carotenoids and sugars composition.

Twenty Citrus cultivars grown in the Mediterranean climate were analysed at different stages of fruit maturity to determinate changes in organic acids, vitamin C and sugars. High-performance liquid chromatographic methods were used to identify and quantify of these compounds. The influences of variety, rootstocks and different stages of fruit maturity were observed. Generally, the vitamin C content was higher in varieties grafted on Troyer citrange that the corresponding cultivars grafted on Cleopatra mandarin. At commercial harvest stage, lemons, clementine mandarins and sweet oranges, showed the highest concentrations of vitamin C; citrons, limes and lemons, the higher amounts of organic acids; and mandarins and hybrids the highest amounts of sugars. Since sugars and acids played an important role in fruit flavor and their nature and concentration largely affect taste characteristic and organoleptic quality, we hope to relate genotypes and differences in final fruit quality. We have found clear differences in the content of sugars, ascorbic and organic acids for the different groups in agreement with the Citrus classification. Also climatic and cultural factors have affected to fruit quality, and anticipate or delay the collection generally results in a loss of bioactive compounds. The fruit quality was affected differently and we have observed differences in accordance with the rootstocks used but, the major differences in nutritional composition must be attributed mainly to genetic factors. The data presented are an important factor to chose varieties with a high potential as nutraceutical source.

BACKGROUND: Citrus fruits have a beneficial effect on human health because of their nutritional and antioxidant properties, and their consumption is associated with a decrease in the incidence of cardiovascular disease and reduced risk of certain cancers. Seven cultivars of mandarin and orange species from the Mediterranean area, grafted onto different rootstocks (Cleopatra mandarin and Troyer citrange), have been analysed. The influence of the rootstock on the content of bioactive compounds is discussed. RESULTS: In all citrus cultivars and rootstocks studied, hesperidin and narirutin flavonoids were the main flavanone glycosides identified, β-cryptoxanthin and violaxanthin the most abundant carotenoids, limonene was the most abundant essential oil, calcium and potassium were the dominant macronutrients and, among the micronutrients, iron and boron represented the highest proportions. CONCLUSION: We have been found clear differences in the content of bioactive compounds for the different groups, in agreement with the Citrus classification. Although both mandarin and orange varieties showed similar tendencies concerning the majority of bioactive constituents, the proportion of the individual nutrients ranged among different cultivars and our results indicated differences between rootstocks although it would be necessary to carry out more analyses, and with the new rootstocks obtained from different breeding programmes, to elucidate conclusive values. Copyright © 2011 Society of Chemical Industry

A comparative study of the primary and secondary metabolites of the juice of several mandarin cultivars with different pollination, seed production and parthenocarpic abilities was carried out, and the antioxidant capacity of the hydrophilic fraction was measured. Correlation by a Principal Component Analysis and a Cluster Analysis was used. By a multivariate analysis, the 15 citrus cultivars were clustered into four groups consistently with citrus types. The presented data are an important factor for choosing varieties with high potential as a nutraceutical source. These aspects are necessary as consumers demand prevention of health problems through nutrition and certain fruit quality traits, including fruit size, internal quality, good rind color and easy peeling.

We describe herein the isolation and semisynthesis of four acetogenin derivatives (1-4) as well as their ability to inhibit the mitochondrial respiratory chain and several tumor cell lines. In addition, four nanoseconds (ns) of MD simulation of compound 4, in a fully hydrated POPC bilayer, is reported.

The objective was to evaluate the efficiency (relation between the cost and the results in health) of the treatments in psoriasis, seeking a higher quality of economic evaluations, consistency and transparency in these studies.We developed a model of economic evaluation in psoriasis collecting all the many direct and indirect costs of each treatment. The effectiveness indicator used was Psoriasis Area Severity Index [PASI 75] which is generally acceptable in studies of psoriasis. The effectiveness indicator was a PASI 75.Subsequently we calculated the Incremental Cost-Effectiveness Ratio (ICER) for the period of 12 weeks and PASI 75, ordering treatments by level of effectiveness at the expense of treatment costs.The most cost effective treatment was methotrexate (ICER -7.5) followed by acitretin (ICER 29.5). The least cost has proved effective PUVA (ICER 4,651), followed by UVB narrow band (2,886.1).when taking into account both direct and indirect costs together with efficiency, methotrexate is the most cost effective treatment.Los nuevos tratamientos biológicos, si bien mejoran la calidad de vida del paciente, incrementan los costes exponencialmente en relación al resto de tratamientos. El objetivo fue calcular el tratamiento más coste efectivo de los existentes para la psoriasis.Se desarrolló un modelo de evaluación económica en psoriasis recogiendo todos los costes directos e indirectos de cada tratamiento. El indicador de efectividad que se utilizó fue Psoriasis Area Severity Index (PASI 75), que es el aceptable de manera general en estudios de psoriasis. Posteriormente se realizó un análisis de incremento coste efectividad (ICER) para el periodo de 12 semanas y PASI 75, ordenando los tratamientos por nivel de efectividad en detrimento de los costes de los tratamientos.El tratamiento más coste efectivo fue el metotrexato (ICER -7,5) seguido de acitretina (ICER 29,5). El menos coste efectivo resultó ser PUVA (ICER 4.651) seguido de UVB de banda estrecha (2.886,1).Aunque el tratamiento más económico teniendo en cuenta solo los costes directos sería el UVBbe, al tener en cuenta los costes indirectos y ajustarlos por la efectividad, el tratamiento más coste efectivo es el metotexato.

The endogenous levels of 13 gibberellins (GAs), three cytokinins (CKs), abscisic acid (ABA), indole-3-acetic acid (IAA) and jasmonic acid (JA) were analyzed in naturally pollinated ovaries of three mandarin cultivars selected for their different capacity to produce seeds and their differing parthenocarpic ability. The varieties compared were Murcott (pollen self-compatible, highly seeded), Moncada (self-incompatible, moderately seeded), and Moncalina (pollen sterile, seedless), obtained from Moncada by bud gamma-irradiation. As expected, the 13-hydroxylation pathway was predominant in ovaries and our results further indicate that cultivar differences exist in GA metabolism. The active gibberellin GA(1) levels in ovaries seems to be related with presence of fertilized ovules and, therefore, with the ability to produce the seeds of a variety. Sterility gamma irradiation arrested the biosynthesis of GA(1) and its precursor GA(19) in Moncalina ovaries if compared to Moncada. The productive efficiency of the studied cultivars also indicated that fruit set depends strongly on the GA(1) level achieved by ovaries, which is also closely related with carbohydrate content. The study of the expression of gibberellin-oxidase genes showed that the pollination/fecundation process enhances GA20ox2 and GA3ox1 activities in naturally pollinated Murcott and Moncada ovaries compared with unpollinated Murcott and Moncalina, respectively. GA2ox1 expression was lower in the ovaries of the highly seeded cultivar Murcott than in those of Moncada or Moncalina. Unpollinated Murcott ovaries contained much lower levels of GA(1) and IAA than the naturally pollinated ovaries of this cultivar. Conversely, unpollinated ovaries, which exhibited 100 % abscission, had more ABA and JA contents. Cytokinin activity seemed constitutive and independent of pollination/fecundation. However, trans-zeatin (t-Z) and 2-isopentenyl adenine (2-IP) concentrations were higher in Murcott ovaries than in Moncada/Moncalina., We thank Drs. Isabel Lopez-Diaz and Esther Carrera for the hormone quantification carried out at the Plant Hormone Quantification Service, IBMCP, Valencia, Spain. This work has been supported by two research Projects, RTA2011-00052-00-00 and RTA2011-00114-00-00, from INIA (Ministerio de Educacion y Ciencia, Spain), by the European Community FEDER and ESF funds, and by the Conselleria de Agricultura, Pesca y Alimentacion (Generalitat Valenciana, Spain).

We report herein the synthesis of new dioxopiperazine isoquinolines using the Pictet–Spengler cyclisation. Our synthetic strategy for the preparation of two new compounds ( 5 , 6 ), with a tetrahydro-6H-pyrazino[1,2-b]isoquinoline-1,4-dione moiety was developed in only four steps. To understand better the crucial step of the synthesis reported here, theoretical calculations using semiempirical (PM3), ab initio and DFT computations were carried out on a reduced system model. The structure of chlorohydrate water solvate of tetrahydro (2-piperidinylethyl)-6H-pyrazino [1,2-b]isoquinoline-1,4-dione ( 6·HCl·2H2O ) was determined by X-ray diffraction. Theoretical calculations (RHF/3-21G and RB3LYP/6-31G(d)) were also performed for compound 6 neutralised with a chloride ion.

In this study, we utilised a number of adenoviral constructs in order to examine the role of intermediates of the NF-kappaB pathway in the regulation of inducible nitric oxide synthase (iNOS) induction in rat aortic smooth muscle cells (RASMCs). Lipopolysaccharide (LPS) stimulated a significant increase in iNOS induction and NF-kappaB DNA binding. These parameters were substantially reduced by overexpression of a wild-type Ikappa-Balpha adenoviral construct (Ad.Ikappa-Balpha), confirming a role for NF-kappaB in iNOS induction. Infection with a dominant-negative IKKalpha adenoviral construct (Ad.IKKalpha+/-) did not significantly affect iNOS induction, NF-kappaB DNA binding or Ikappa-Balpha loss. Infection of RASMCs with adenovirus encoding a dominant-negative IKKbeta (Ad.IKKbeta+/-) essentially abolished iNOS induction and activation of the NF-kappaB pathway. Pretreatment of RASMCs with a novel specific inhibitor of IKKbeta, SC-514, significantly reduced iNOS induction, NF-kappaB DNA binding and I-kappaBalpha loss in a concentration-dependent manner. In both RASMCs and human umbilical vein endothelial cells (HUVECs), infection with Ad.IKKbeta+/- also inhibited COX-2 expression in response to LPS. However, Ad.IKKalpha+/- was again without effect. These data suggest that IKKbeta plays a predominant, selective role in the regulation of NF-kappaB-dependent induction of iNOS in RASMCs.

An exhaustive conformational study on the benzyltetrahydroisoquinolines (BTHIQ) from ab initio (RHF/6-31G(d)) calculations was carried out. The effects of different substituents at chiral C 1 atom were also considered. Our results indicate that different substituents at C 1 in BTHIQ molecules introduce a significant steric hindrance which, in turn, might be responsible for a conformational restriction favouring or disfavouring the spatial orientation of the lone pairs of N atom allowing or not the electronic attachment with the side chain of Asp residue. These results can serve as an aid for designing suitable structures of BTHIQs for better dopamine D 1 -receptor inhibitory activity.

Modifications in the terminal alpha,beta-unsaturated gamma-methyl-gamma-lactone moiety or in the alkyl chain that links this terminal gamma-lactone with the alpha,alpha'-dihydroxylated THF system of the natural mono-tetrahydrofuranic acetogenins, annonacin and annonacinone, led to the preparation of eight semisynthetic derivatives. Their inhibitory effects on mitochondrial complex I is discussed and compared with that of the classical complex I inhibitor, rotenone.

We describe the preparation in a ‘one-pot’ sequence 1-cyclohexylmethyl 7,8-dioxygenated tetrahydroisoquinoline, substituted and unsubstituted in the C ring by application of the Photo–Fries transposition, followed by a tandem reduction–cyclization and further reduction. Indeed, we have accomplished for the first time regioselective hydrogenation of the benzylic ring of the tetrahydroisoquinoline systems. All 1-cyclohexylmethyl THIQ synthesized were able to displace D2 dopamine receptor from its specific binding site in rat striatal membranes, while the N-methylated derivatives showed also affinity for D1 dopamine receptors.

A series of 1-substituted 3,4-dihydroisoquinolines were synthesized and tested in vitro against the leukemia L 1210 cell line to evaluate their ability to perturb the cell cycle by arresting cells in the G1 phase. 1-Benzoylimines, 1-phenylimines, and 1-alkylimines were synthesized. The most powerful cytotoxic derivatives, 1-benzoyl-3,4-dihydroisoquinolines (1-26), were obtained from amides I via 1-benzyl-3,4-dihydroisoquinoline in good yield by a direct selective oxidation of the benzylic carbon of the corresponding imines through 10% Pd/C in acetonitrile. SAR studies let us to identify the essential structural features for cytotoxic activity. The most bioactive compounds (with IC(50)5 microM) were BzDHIQ (13, 22, 21, 8, 9, 11, 1, 20, 6, and 19), and they are characterized by the following: (i) An alpha-ketoimine moiety is necessary for potent antiproliferative activity (1-phenyl- and 1-alkyl-3,4-dihydroisoquinoline derivatives, 34-40, are less active). (ii) An hydrophobic, benzyloxy, alkyloxy, or allyloxy group at the C-6 position seems to be relevant for cytotoxicity. (iii) Regarding the influence of the benzoylic moiety, both the unsubstituted (13, 8, 9, 11, 1, and 6) and the 3'-monosubstituted (22, 21, 20, and 19) compounds were more potent than compounds with other substitutions.

Methoxymethylation of altholactone ( 1 ) led to the corresponding O -methoxymethyl derivative ( 3 ) in addition to the unexpected 6,7-dihydro-7-methoxy analogue ( 4 ), and two original tetrahydrofuranic (THF) alkyl esters ( 5 , 6 ). Moreover, when we accomplished a new method for the preparation of the furano-pyrone goniofupyrone ( 7 ) through 7-hydroxylation of 1 in acid medium, a minor compound ( 8 ) with an identical skeleton to that of compounds 5 and 6 was identified. Careful examination of the published spectral data of the reported styryl-lactones with an heptolide skeleton reveals that those structures possess also a THF alkyl ester skeleton. The revision of those structures was confirmed by chemical correlation. All altholactone derivatives assayed proved to be specific inhibitors of the mitochondrial complex I.

In the present study we examine the mechanism by which thaligrisine, a bisbenzyltetrahydroisoquinoline alkaloid, inhibits the contractile response of vascular smooth muscle. The work includes functional studies on rat isolated aorta and tail artery precontracted with noradrenaline or KCl. In other experiments rat aorta was precontracted by caffeine in the presence or absence of extracellular Ca 2 +. In order to assess whether thaligrisine interacts directly with calcium channel binding sites or with α-adrenoceptors we examined the effect of the alkaloid on [ 3 H]-(+)- cis diltiazem, [ 3 H]-nitrendipine and [ 3 H]-prazosin binding to cerebral cortical membranes. The functional studies showed that the alkaloid inhibited in a concentration-dependent manner the contractile response induced by depolarization in rat aorta (IC 50 =8.9±2.9 μM, n=5) and in tail artery (IC 50 =3.04±0.3 μM, n=6) or noradrenaline induced contraction in rat aorta (IC 50 =23.0±0.39 μM, n=9) and in tail artery (IC 50 =3.8±0.9 μM, n=7). In rat aorta, thaligrisine concentration-dependently inhibited noradrenaline-induced contraction in Ca 2 +-free solution (IC 50 = 13.3 μM, n=18). The alkaloid also relaxed the spontaneous contractile response elicited by extracellular calcium after depletion of noradrenaline-sensitive intracellular stores (IC 50 = 7.7 μM, n=4). The radioligand receptor-binding study showed that thaligrisine has higher affinity for [ 3 H]-prazosin than for [ 3 H]-(+)- cis -diltiazem binding sites, with Ki values of 0.048±0.007 μM and 1.5±1.1 μM respectively. [ 3 H]-nitrendipine binding was not affected by thaligrisine. The present work provides evidence that thaligrisine shows higher affinity for [ 3 H]-prazosin binding site than [ 3 H]-(+)- cis -diltiazem binding sites, in contrast with tetrandrine and isotetrandrine that present similar affinity for both receptors. In functional studies thaligrisine, acted as an α 1 -adrenoceptor antagonist and as a Ca 2 + channel blocker, relaxing noradrenaline or KCl-induced contractions in vascular smooth muscle. This compound specifically inhibits the refilling of internal Ca 2 +-stores sensitive to noradrenaline, by blocking Ca 2 +-entry through voltage-dependent Ca 2 +-channels.

The synthesis of N-(O,O-diisopropylphosphoryl)-benzyltetrahydroisoquinoline (3) has been achieved in a 'one pot' procedure from imine (2) and diisopropyl-phosphorochloridate (1) generated in situ (POCl3 + iPrOH). Compound 3 is the first benzyltetrahydroisoquinoline derivative found to be a potent inhibitor of mitochondrial complexes I and III, and therefore it opens a new perspective with this series of compounds as they can be considered as new class of antitumor agents.

Thirty-one bioactive styryl-lactones, with six different basic skeletons, have been isolated from Goniothalamus species. Aspects of their isolation, structural elucidation, biogenesis and biological activity are reviewed. Copyright © 1999 John Wiley & Sons, Ltd.

The fractionation of the methanolic extract of Goniothalamus arvensis (Annonaceae) stem bark led to the isolation of two novel styryl-lactones, arvensin and (+)-2-epi-altholactone. The structures of these compounds, which belong to the furano-pyrone group, were established on the basis of mass spectrometry, one- and two-dimensional nuclear magnetic resonance experiments, as well as simple chemical derivatization. The relative and absolute configurations of the compounds are discussed. Copyright © 1999 John Wiley & Sons, Ltd.

The effects of two weeks of oral administration of the angiotensin-converting enzyme inhibitors captopril (a sulphydryl-containing drug) and enalapril (which lacks the sulphydryl group) on skeletal muscle glucose uptake, arterial blood pressure, cardiac hypertrophy, proteinuria and aortic vascular reactivity in obese Zucker rats were evaluated. Captopril (50 mg kg(-1) once daily) and enalapril (10 mg kg(-1) did not modify body weight gain or food or water intake. Both drugs decreased systolic blood pressure (157+/-6, 133+/-4 and 136+/-3 mm Hg, in vehicle-, captopril- and enalapril-treated rats, respectively), blood glucose (172+/-8 vs. 151+/-7 and 158+/-5 mg dl(-1), respectively), proteinuria (46+/-10 vs. 17+/-2 and 18+/-2.5 mg dl(-1), respectively) and heart weight (2.17+/-0.03, 1.98+/-0.02 and 1.99+/-0.04 mg g(-1)of body weight, respectively). Plasma insulin concentration was significantly increased by enalapril (17+/-2 ng ml(-1) vs. 9+/-2) but not by captopril (12+/-1). In the absence of insulin, the diaphragms from captopril- or enalapril-treated rats showed a significantly higher glucose uptake than that of controls (31% and 30% vs. control group, respectively). The presence of insulin in the incubation medium did not stimulate peripheral glucose uptake in the control group but significantly increased glucose uptake in diaphragms from captopril- or enalapril-treated rats (enhancement of glucose uptake vs. control: 52% and 43%, respectively). Endothelium-intact aortic rings from control Zucker rats showed a poor relaxant response to acetylcholine (maximal relaxation of 38.4+/-4.7%). Captopril significantly improved the endothelium-dependent vascular relaxation responses to acetylcholine and the endothelium-independent relaxation to the nitric oxide donor sodium nitroprusside whereas enalapril did not modify these relaxant responses. Neither captopril nor enalapril significantly affected the vascular contractile responses to the vasoconstrictors noradrenaline or KCl. In conclusion, the angiotensin-converting enzyme inhibitors captopril and enalapril reversed insulin resistance and the associated cardiovascular complications (cardiac hypertrophy, hypertension and proteinuria) in the obese Zucker rat, an animal model of non-insulin-dependent (type II) diabetes mellitus. However, only captopril, but not enalapril, improved the impaired endothelium-dependent and independent relaxant responses in the isolated rat aorta.