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  • 1.
    Cipriano, Mariateresa
    et al.
    Umeå University, Faculty of Medicine, Department of Pharmacology and Clinical Neuroscience, Pharmacology.
    Gouveia-Figueira, Sandra
    Umeå University, Faculty of Science and Technology, Department of Chemistry. Umeå University, Faculty of Medicine, Department of Pharmacology and Clinical Neuroscience, Pharmacology.
    Persson, Emma
    Umeå University, Faculty of Medicine, Department of Radiation Sciences.
    Nording, Malin
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Fowler, Christopher
    Umeå University, Faculty of Medicine, Department of Pharmacology and Clinical Neuroscience, Pharmacology.
    The influence of monoacylglycerol lipase inhibition upon the expression of epidermal growth factor receptor in human PC-3 prostate cancer cells.2014In: BMC Research Notes, ISSN 1756-0500, E-ISSN 1756-0500, Vol. 7, p. 441-447Article in journal (Refereed)
    Abstract [en]

    Background: It has been reported that direct activation of the cannabinoid CB1 receptor in epidermal growth factor (EGR)-stimulated PC-3 prostate cancer cells results in an anti-proliferative effect accompanied by a down-regulation of EGF receptors (EGFR). In the present study, we investigated whether similar effects are seen following inhibition of the endocannabinoid hydrolytic enzyme monoacylglycerol lipase (MGL).

    Results: CB1 receptor expression levels were found to differ greatly between two experimental series conducted using PC-3 cells. The monoacylglycerol lipase inhibitor JZL184 increased levels of 2-arachidonoylglycerol in the PC-3 cells without producing changes in the levels of anandamide and related N-acylethanolamines. In the first series of experiments, JZL184 produced a small mitogenic effect for cells that had not been treated with EGF, whereas an anti-proliferative effect was seen for EGF-treated cells. An anti-proliferative effect for the EGF-treated cells was also seen with the CB receptor agonist CP55,940. In the second batch of cells, there was an interaction between JZL184 and CB1 receptor expression densities in linear regression analyses with EGFR expression as the dependent variable.

    Conclusions: Inhibition of MGL by JZL184 can affect EGFR expression. However, the use in our hands of PC-3 cells as a model to investigate the therapeutic potential of MGL inhibitors and related compounds is compromised by their variability of CB1 receptor expression.

  • 2.
    Gouveia, Sandra C.
    et al.
    University of Madeira, Portugal.
    Castilho, Paula C.
    University of Madeira, Portugal.
    Artemisia annua L.: Essential oil and acetone extract composition and antioxidant capacity2013In: Industrial crops and products (Print), ISSN 0926-6690, E-ISSN 1872-633X, Vol. 45, p. 170-181Article in journal (Refereed)
    Abstract [en]

    Aerial parts of Artemisia annua growth in three different locations of Madeira Archipelago were studied. The essential oil composition was established by GC-MS and the main components were mono- and sesquiterpenes; artemisia ketone was not detected. The presence of phenolic compounds in the acetone extracts was investigated by HPLC-DAD-ESI/MSn and a diversified phenolic profile of 40 hydrocinnamic acid derivatives and glycosylated flavonoids was found. A few compounds were reported for the first time in Artemisia annua. The antioxidant capacity of essential oils and extracts were measured by three different in vitro assays. For the essential oils, a very good antioxidant response was found and the extracts also showed a good antioxidant capacity, in particular as antiradical scavengers. (C) 2012 Elsevier B.V. All rights reserved.

  • 3.
    Gouveia-Figueira, Sandra C.
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry. Funchal, Portugal.
    Castilho, Paula C.
    Funchal, Portugal.
    Phenolic screening by HPLC-DAD-ESI/MSn and antioxidant capacity of leaves, flowers and berries of Rubus grandifolius Lowe2015In: Industrial crops and products (Print), ISSN 0926-6690, E-ISSN 1872-633X, Vol. 73, p. 28-40Article in journal (Refereed)
    Abstract [en]

    In Madeira Island (Macaronesia Island), Rubus grandifolius Lowe berries, locally known by amoras, are widely consumed fresh or processed as jam, juice or liquor. Folk medicine describes R. grandifolius Lowe fruits and leaves being used to treat diabetes, as depurative, diuretic and to relieve sore throat. The aim of this study was to investigate phenolic composition and antioxidant capacity of the different edible parts of the plant (berries, leaves and flowers). HPLC-DAD-ESI/MSn was used to establish the phenolic profile. Phenolic monomers such as flavonol O-glycosilated (quercetin and kaempferol), quinic acid and caffeic acid conjugates were characterized using the electrospray source in the negative mode; while positive mode was employed to detect glycosylated anthocyanins (cyanidin, delphinin and petunidin). The berries presented a higher radical scavenger capacity (DPPH and ABTS assays) and reducing properties (FRAP) than the leaves and the flowers. Ethanolic extracts showed highest antioxidant capacity when compared with water based extracts: DPPH values of 147.9 +/- 0.7 mu mol eq Trolox/g DM; ABTS value of 255.8 +/- 1.9 mu mol-eq Trolox/g DM and FRAP value 9455 +/- 29 mmol Fe(II)/mgDM). (C) 2015 Elsevier B.V. All rights reserved.

  • 4.
    Gouveia-Figueira, Sandra
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Nording, Malin L.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Development and Validation of a Sensitive UPLC-ESI-MS/MS Method for the Simultaneous Quantification of 15 Endocannabinoids and Related Compounds in Milk and Other Biofluids2014In: Analytical Chemistry, ISSN 0003-2700, E-ISSN 1520-6882, Vol. 86, no 2, p. 1186-1195Article in journal (Refereed)
    Abstract [en]

    The endocannabinoid (eCB) system has gained an increasing interest over the past decades since the discovery of anandamide and 2-arachidonoyl glycerol (2-AG). These, and structurally related compounds, are associated with a wide variety of physiological processes. For instance, eCB levels in milk have been associated with infants' feeding and sleeping behavior. A method based on ultraperformance liquid chromatography coupled with electrospray ionization tandem mass spectrometry (UPLC-ESI-MS/MS) was developed and validated for the simultaneous quantification of 15 eCBs and related compounds, including both fatty acid amides and glycerols. Linearity (0.9845 < R-2 < 1), limit of detection and quantification (0.52-293 pg on column), inter- and intraday accuracy (>70%) and precision (CV < 15%), stability, and recovery (in milk and plasma) were established in accordance to the U.S. Food and Drug Administration guidelines. The method was successfully applied to bovine and elk milk revealing species-specific eCB profiles, with significant different levels of 2-AG, 2-linoleoyl glycerol, docosahexaenoyl ethanolamide, palmitoyl ethanolamide, and oleoyl ethanolamide. Furthermore, stearoyl ethanolamide and docosatetraenoyl ethanolamide were only detected in elk milk. In summary, our UPLC-ESI-MS/MS method may be used for quantification of eCBs and related compounds in different biofluids and applied to investigations of the role of these emerging compounds in various physiological processes.

  • 5.
    Gouveia-Figueira, Sandra
    et al.
    Umeå University, Faculty of Medicine, Department of Pharmacology and Clinical Neuroscience, Pharmacology. Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Nording, Malin L.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Gaida, Jamie E.
    Forsgren, Sture
    Umeå University, Faculty of Medicine, Department of Integrative Medical Biology (IMB).
    Alfredson, Hakan
    Fowler, Christopher J.
    Umeå University, Faculty of Medicine, Department of Pharmacology and Clinical Neuroscience, Pharmacology.
    Serum Levels of Oxylipins in Achilles Tendinopathy: An Exploratory Study2015In: PLoS ONE, ISSN 1932-6203, E-ISSN 1932-6203, Vol. 10, no 4, article id e0123114Article in journal (Refereed)
    Abstract [en]

    Background: Linoleic acid-derived oxidation products are found in experimental pain models. However, little is known about the levels of such oxylipins in human pain. In consequence, in the present study, we have undertaken a lipidomic profiling of oxylipins in blood serum from patients with Achilles tendinopathy and controls.

    Methodology/Principal findings: A total of 34 oxylipins were analysed in the serum samples. At a significance level of P<0.00147 (<0.05/34), two linoleic acid-derived oxylipins, 13-hydroxy-10E,12Z-octadecadienoic (13-HODE) and 12(13)-dihydroxy-9Z-octadecenoic acid (12,13-DiHOME) were present at significantly higher levels in the Achilles tendinopathy samples. This difference remained significant when the dataset was controlled for age, gender and body-mass index. In contrast, 0/21 of the arachidonic acid- and 0/4 of the dihomo-γ-linolenic acid, eicosapentaenoic acid or docosahenaenoic acid-derived oxylipins were higher in the patient samples at this level of significance. The area under the Receiver-Operator Characteristic (ROC) curve for 12,13-DiHOME was 0.91 (P<0.0001). Levels of four N-acylethanolamines were also analysed and found not to be significantly different between the controls and the patients at the level of P<0.0125 (<0.05/4).

    Conclusions/Significance: It is concluded from this exploratory study that abnormal levels of linoleic acid-derived oxylipins are seen in blood serum from patients with Achilles tendinopathy. Given the ability of two of these, 9- and 13-HODE to activate transient receptor potential vanilloid 1, it is possible that these changes may contribute to the symptoms seen in Achilles tendinopathy.

  • 6.
    Gouveia-Figueira, Sandra
    et al.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Spath, Jana
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Zivkovic, Angela M.
    Nording, Malin L.
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Profiling the Oxylipin and Endocannabinoid Metabolome by UPLC-ESI-MS/MS in Human Plasma to Monitor Postprandial Inflammation2015In: PLoS ONE, ISSN 1932-6203, E-ISSN 1932-6203, Vol. 10, no 7, article id e0132042Article in journal (Refereed)
    Abstract [en]

    Bioactive lipids, including oxylipins, endocannabinoids, and related compounds may function as specific biochemical markers of certain aspects of inflammation. However, the postprandial responsiveness of these compounds is largely unknown; therefore, changes in the circulating oxylipin and endocannabinoid metabolome in response to a challenge meal were investigated at six occasions in a subject who freely modified her usual diet. The dietary change, and especially the challenge meal itself, represented a modification of precursor fatty acid status, with expectedly subtle effects on bioactive lipid levels. To detect even the slightest alteration, highly sensitive ultra-performance liquid chromatography (UPLC) coupled to electrospray ionization (ESI) tandem mass spectrometry (MS/MS) methods for bioactive lipid profiling was employed. A previously validated UPLC-ESI-MS/MS method for profiling the endocannabinoid metabolome was used, while validation of an UPLC-ESI-MS/MS method for oxylipin analysis was performed with acceptable outcomes for a majority of the parameters according to the US Food and Drug Administration guidelines for linearity (0.9938 < R-2 < 0.9996), limit of detection (0.0005-2.1 pg on column), limit of quantification (0.0005-4.2 pg on column), inter-and intraday accuracy (85-115%) and precision (<5%), recovery (40-109%) and stability (40-105%). Forty-seven of fifty-two bioactive lipids were detected in plasma samples at fasting and in the postprandial state (0.5, 1, and 3 hours after the meal). Multivariate analysis showed a significant shift of bioactive lipid profiles in the postprandial state due to inclusion of dairy products in the diet, which was in line with univariate analysis revealing seven compounds (NAGly, 9-HODE, 13-oxo-ODE, 9(10)-EpOME, 12(13)-EpOME, 20-HETE, and 11,12-DHET) that were significantly different between background diets in the postprandial state (but not at fasting). The only change in baseline levels at fasting was displayed by TXB2. Furthermore, postprandial responsiveness was detected for seven compounds (POEA, SEA, 9(10)-DiHOME, 12(13)-DiHOME, 13-oxo-ODE, 9-HODE, and 13-HODE). Hence, the data confirm that the UPLC-ESI-MS/MS method performance was sufficient to detect i) a shift, in the current case most notably in the postprandial bioactive lipid metabolome, caused by changes in diet and ii) responsiveness to a challenge meal for a subset of the oxylipin and endocannabinoid metabolome. To summarize, we have shown proof-of-concept of our UPLC-ESI-MS/MS bioactive lipid protocols for the purpose of monitoring subtle shifts, and thereby useful to address lipid-mediated postprandial inflammation.

  • 7. Llorent-Martinez, Eulogio J.
    et al.
    Spinola, Vitor
    Gouveia, Sandra
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Castilho, Paula C.
    HPLC-ESI-MSn characterization of phenolic compounds, terpenoid saponins, and other minor compounds in Bituminaria bituminosa2015In: Industrial crops and products (Print), ISSN 0926-6690, E-ISSN 1872-633X, Vol. 69, p. 80-90Article in journal (Refereed)
    Abstract [en]

    Bituminaria bituminosa is a wild legume that can endure drastic conditions, including contaminated and degraded soils. It has been traditionally used as feeding for livestock, and different uses in folk medicine are known. The chemical composition of leaves and flowers from B. bituminosa is presented for the first time. The screening of phytochemical compounds was carried out using high-performance liquid chromatography with electrospray ionization mass spectrometric detection (HPLC-ESI-MSn). More than 40 compounds were identified or tentatively characterized. A high percentage of the detected compounds corresponded to glycosylated flavonoids, especially from apigenin, although phenolic acids, lignans, and saponins were also identified.

  • 8. Spinola, Vitor
    et al.
    Llorent-Martinez, Eulogio J.
    Gouveia, Sandra
    Umeå University, Faculty of Science and Technology, Department of Chemistry.
    Castilho, Paula C.
    Myrica faya: A New Source of Antioxidant Phytochemicals2014In: Journal of Agricultural and Food Chemistry, ISSN 0021-8561, E-ISSN 1520-5118, Vol. 62, no 40, p. 9722-9735Article in journal (Refereed)
    Abstract [en]

    Myrica faya is a fruit tree endemic of the Macaronesia (Azores, Madeira, and Canary Island), and its edible fruits are known as "amorinhos" (little loves), bright red to purple berries , used fresh and in jams and liquors. The phenolic composition and antioxidant capacity of leaves and berries from M faya are presented here for the first time. The screening of phytochemical compounds was carried out using high-performance liquid chromatography with online. UV and electrospray ionization mass spectrometric detection (HPLC-DAD-ESI-MS"). There were 55 compounds characterized, mostly galloyl esters of flavonoids and phenolic acids; 26 of the identified compounds (anthocyannis, isoflavonoids, lignans, terpenes, fatty acids, and phenylethanoids) have not been reported in Myrica genus so far. From the data presented here, it can be concluded that faya berries represent a rich source of cyanidin-3-glucoside, flavonoids, vitamin C. In fact, higher antioxidant activity than that of the well-known Myrica rubra berries (Chinese bayberry) has been observed.

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