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Research Paper

UHPLC-ESI-ORBITRAP-MS analysis of the native Mapuche medicinal plant palo negro (Leptocarpha rivularis DC. – Asteraceae) and evaluation of its antioxidant and cholinesterase inhibitory properties

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Pages 936-944 | Received 03 Jan 2018, Accepted 13 Apr 2018, Published online: 07 May 2018

References

  • Martinez R, Kesternich V, Carrasco H, et al. Structure, conformation and biological activity studies on rivularin, a new heliangolide isolated from Leptocarpha rivularis. Bol Soc Chilena Quim 1998;43:7–12.
  • Martinez R, Ayamante IS, Nunezalarcon JA, et al. Leptocarpin and 17,18-dihydroleptocarpin, 2 new heliangolides from Leptocarpha rivularis. Phytochemistry 1979;18:1527–8.
  • Bosio C, Tomasoni G, Martínez R, et al. Cytotoxic and apoptotic effects of leptocarpin, a plant-derived sesquiterpene lactone, on human cancer cell lines. Chem Biol Interact 2015;242:415–21.
  • Uquiche E, Garcés F. Recovery and antioxidant activity of extracts from Leptocarpha rivularis by supercritical carbon dioxide extraction. J Supercrit Fluids 2016;110:257–64.
  • Niemeyer HM. Composition of essential oils from five aromatic species of asteraceae. J Essent Oil Res 2009;21:350–3.
  • Amorati R, Foti MC, Valgimigli L. Antioxidant activity of essential oils. J Agric Food Chem 2013;61:10835–47.
  • Spinola V, Llorent-Martinez EJ, Gouveia S, et al. Myrica faya: a new source of antioxidant phytochemicals. J Agric Food Chem 2014;62:9722–35.
  • Prameela K, Venkatesh K, Immandi SB, et al. Next generation nutraceutical from shrimp waste: the convergence of applications with extraction methods. Food Chem 2017; 237:121–32.
  • Aarli JA, Dua T, Janca A, et al., Neurological disorders. Public health challenges. Geneva: World Health Organization; 2006.
  • Gotz J, Ittner A, Ittner LM. Tau-targeted treatment strategies in Alzheimer's disease. Br J Pharmacol 2012;165:1246–59.
  • Ballard C, Gauthier S, Corbett A, et al. Alzheimer's disease. Lancet 2011; 377:1019–31.
  • Yi L, Liu W, Wang Z, et al. Characterizing Alzheimer's disease through metabolomics and investigating anti-Alzheimer's disease effects of natural products. Ann New York Acad Sci 2017;1398:130–41.
  • Dey A, Bhattacharya R, Mukherjee A, et al. Natural products against Alzheimer's disease: pharmaco-therapeutics and biotechnological interventions. Biotechnol Adv 2017;35:178–216.
  • Bassil N, Grossberg GT. Novel regimens and delivery systems in the pharmacological treatment of Alzheimer's Disease. CNS Drugs 2009;23:293–307.
  • Custódio L, Patarra J, Alberício F, et al. Extracts from Quercus sp. acorns exhibit in vitro neuroprotective features through inhibition of cholinesterase and protection of the human dopaminergic cell line SH-SY5Y from hydrogen peroxide-induced cytotoxicity. Ind Crops Prod 2013;45:114–20.
  • Trung Kien N, Kyung Hoan L, Jaehyuk C, et al. Evaluation of antioxidant, anti-cholinesterase, and anti-inflammatory effects of culinary mushroom Pleurotus pulmonarius. Mycobiology 2016;44:291–301.
  • Melucci D, Locatelli M, Locatelli C, et al. A comparative assessment of biological effects and chemical profile of Italian Asphodeline lutea extracts. Molecules 2018;23:461.
  • Le Pogam P, Schinkovitz A, Legouin B, et al. Matrix-Free UV-laser desorption ionization mass spectrometry as a versatile approach for accelerating dereplication studies on Lichens. Anal Chem 2015;87:10421–8.
  • Musharraf SG, Kanwal N, Thadhani VM, et al. Rapid identification of lichen compounds based on the structure-fragmentation relationship using ESI-MS/MS analysis. Anal Meth 2015;7:6066–76.
  • Cornejo A, Salgado F, Caballero J, et al. Secondary metabolites in Ramalina terebrata detected by UHPLC/ESI/MS/MS and identification of parietin as Tau protein inhibitor. Int J Mol Sci 2016;17:1703.
  • Castro ON, Benites J, Rodilla J, et al. Metabolomic analysis of the Lichen Everniopsis trulla using ultra high performance liquid chromatography-quadrupole-Orbitrap Mass Spectro-metry (UHPLC-Q-OT-MS). Chromatographia 2017;80:967–73.
  • Simirgiotis MJ, Quispe C, Bórquez J, et al. Fast high resolution Orbitrap MS fingerprinting of the resin of Heliotropium taltalense Phil. from the Atacama Desert. Ind Crops Prod 2016;85:159–66.
  • Sepulveda B, Quispe C, Simirgiotis M, et al. Gastroprotective effects of new diterpenoid derivatives from Azorella cuatrecasasii Mathias & Constance obtained using a β-cyclodextrin complex with microbial and chemical transformations. Bioorg Med Chem Lett 2016;26:3220–2.
  • Simirgiotis MJ, Bórquez J, Neves-Vieira M, et al. Fast isolation of cytotoxic compounds from the native Chilean species Gypothamnium pinifolium Phil. collected in the Atacama Desert, northern Chile. Ind Crops Prod 2015;76:69–76.
  • Simirgiotis MJ, Quispe C, Areche C, et al. Phenolic compounds in Chilean Mistletoe (Quintral, Tristerix tetrandus) analyzed by UHPLC-Q/Orbitrap/MS/MS and its antioxidant properties. Molecules 2016;21:245.
  • Simirgiotis MJ, Quispe C, Bórquez J, et al. Fast detection of phenolic compounds in extracts of Easter pears (Pyrus communis) from the Atacama Desert by ultrahigh-performance liquid chromatography and mass spectrometry (UHPLC-Q/Orbitrap/MS/MS). Molecules 2016;21:92–105.
  • Simirgiotis MJ, Ramirez JE, Hirschmann GS, et al. Bioactive coumarins and HPLC-PDA-ESI-ToF-MS metabolic profiling of edible queule fruits (Gomortega keule), an endangered endemic Chilean species. Food Res Int 2013;54:532–43.
  • Brand-Williams W, Cuvelier ME, Berset C. Use of a free radical method to evaluate antioxidant activity. LWT – Food Sci Technol 1995;28:25–30.
  • Kim DO, Lee KW, Lee HJ, et al. Vitamin C equivalent antioxidant capacity (VCEAC) of phenolic phytochemicals. J Agric Food Chem 2002;50:3713–7.
  • Kuskoski EM, Asuero AG, García-Parilla MC, et al. Actividad antioxidante de pigmentos antociánicos. Food Sci Technol 2004;24:691–3.
  • Benzie IFF, Strain JJ. The ferric reducing ability of plasma (FRAP) as a measure of “antioxidant power”: the FRAP assay. Anal Biochem 1996;239:70–6.
  • Simirgiotis MJ, Borquez J, Schmeda-Hirschmann G. Antioxidant capacity, polyphenolic content and tandem HPLC-DAD-ESI/MS profiling of phenolic compounds from the South American berries Luma apiculata and L. chequén. Food Chem 2013;139:289–99.
  • Aktumsek A, Zengin G, Guler GO, et al. Antioxidant potentials and anticholinesterase activities of methanolic and aqueous extracts of three endemic Centaurea L. species. Food Chem Toxicol 2013;55:290–6.
  • Llorent-Martinez EJ, Zengin G, Fernandez-de Cordova ML, et al. Traditionally used Lathyrus species: phytochemical composition, antioxidant activity, enzyme inhibitory properties, cytotoxic effects, and in silico studies of L. czeczottianus and L. nissolia. Front Pharmacol 2017;8:83.
  • Wu H, Huang T, Cao F, et al. Co-production of HMF and gluconic acid from sucrose by chemo-enzymatic method. Chem Eng J 2017;327:228–34.
  • Brito A, Ramirez JE, Areche C, et al. HPLC-UV-MS profiles of phenolic compounds and antioxidant activity of fruits from three citrus species consumed in Northern Chile. Molecules 2014;19:17400–21.
  • Abu Irmaileh BE, Al-Aboudi AMF, Abu Zarga MH, et al. Selective phytotoxic activity of 2,3,11 beta,13-tetrahydroaromaticin and ilicic acid isolated from Inula graveolens. Nat Prod Res 2015;29:893–8.
  • Nam MH, Son WR, Yang SY, et al. Chebulic acid inhibits advanced glycation end products-mediated vascular dysfunction by suppressing ROS via the ERK/Nrf2 pathway. J Funct Foods 2017;36:150–61.
  • Sonmezdag AS, Kelebek H, Selli S. Pistachio oil (Pistacia vera L. cv. Uzun): characterization of key odorants in a representative aromatic extract by GC-MS-olfactometry and phenolic profile by LC-ESI-MS/MS. Food Chem 2018;240:24–31.
  • Kent PW, Brunet PCJ. The occurrence of protocatechuic acid and its 4-O-β-d-glucoside in Blatta and Periplaneta. Tetrahedron 1959;7:252–6.
  • Silva RV, Costa SCC, Branco CRC, et al. In vitro photoprotective activity of the Spondias purpurea L. peel crude extract and its incorporation in a pharmaceutical formulation. Ind Crops Prod 2016;83:509–14.
  • Mollica A, Locatelli M, Macedonio G, et al. Microwave-assisted extraction, HPLC analysis, and inhibitory effects on carbonic anhydrase I, II, VA, and VII isoforms of 14 blueberry Italian cultivars. J Enz Inhib Med Chem 2016;31:1–6.
  • Willems JL, Khamis MM, Mohammed Saeid W, et al. Analysis of a series of chlorogenic acid isomers using differential ion mobility and tandem mass spectrometry. Anal Chim Acta 2016;933:164–74.
  • Clifford MN, Knight S, Kuhnert N. Discriminating between the six isomers of dicaffeoylquinic acid by LC-MS(n). J Agric Food Chem 2005;53:3821–32.
  • Han J, Wang D, Ye L, et al. Rosmarinic acid protects against inflammation and cardiomyocyte apoptosis during myocardial ischemia/reperfusion injury by activating peroxisome proliferator-activated receptor gamma. Front Pharmacol 2017;8.
  • Simirgiotis MJ. Antioxidant capacity and HPLC-DAD-MS profiling of Chilean Peumo (Cryptocarya alba) fruits and comparison with German Peumo (Crataegus monogyna) from Southern Chile. Molecules 2013;18:2061–80.
  • Simirgiotis MJ, Benites J, Areche C, et al. Antioxidant capacities and analysis of phenolic compounds in three endemic Nolana species by HPLC-PDA-ESI-MS. Molecules 2015;20:11490–507.
  • Eshbakova K, Yili A, Aisa H. Phenolic Constituents of Pulicaria gnaphaloides. Chem Nat Comp 2014;50:737–8.
  • Liu D-Y, Shi X-F, Wang D-d, et al. Two new myricetin glycosides from pine needles of Cedrus deodara. Chem Nat Comp 2011;47:704–7.
  • Veitch NC, Grayer RJ. Flavonoids and their glycosides, including anthocyanins. Nat Prod Rep 2008;25:555–611.
  • Jie LIU, REN H, Bin LIU, et al. Diosmetin inhibits cell proliferation and induces apoptosis by regulating autophagy via the mammalian target of rapamycin pathway in hepatocellular carcinoma HepG2 cells. Oncol Lett 2016;12:4385–92.
  • Jiménez-Sánchez C, Lozano-Sánchez J, Rodríguez-Pérez C, et al. Comprehensive, untargeted, and qualitative RP-HPLC-ESI-QTOF/MS2 metabolite profiling of green asparagus (Asparagus officinalis). J Food Comp Anal 2016;46:78–87.
  • Hu WJ, Pan XL, Abbas HMK, et al. Metabolites contributing to Rhizoctonia solani AG-1-IA maturation and sclerotial differentiation revealed by UPLC-QTOF-MS metabolomics. PloS One 2017;12:e0177464.
  • Zengin G, Uysal A, Aktumsek A, et al. Euphorbia denticulata Lam.: a promising source of phyto-pharmaceuticals for the development of novel functional formulations. Biomed Pharmacother 2017;87:27–36.
  • Martin-Arjol I, Bassas M, Bermudo E, et al. Identification of oxylipins with antifungal activity by LC-MS/MS from the supernatant of Pseudomonas 42A2. Chem Phys Lip 2010;163:341–6.
  • Mocan A, Moldovan C, Zengin G, et al. UHPLC-QTOF-MS analysis of bioactive constituents from two Romanian Goji (Lycium barbarum L.) berries cultivars and their antioxidant, enzyme inhibitory, and real-time cytotoxicological evaluation. Food Chem Toxicol 2018;115:414–24.
  • Mocan A, Zengin G, Simirgiotis M, et al. Functional constituents of wild and cultivated Goji (L. barbarum L.) leaves: phytochemical characterization, biological profile, and computational studies. J Enz Inhibit Med Chem 2017;32:153–68.,
  • Seo WD, Kim JY, Ryu HW, et al. Identification and characterisation of coumarins from the roots of Angelica dahurica and their inhibitory effects against cholinesterase. J Funct Foods 2013;5:1421–31.
  • Orhan IE, Gulyurdu F, Kupeli Akkol E, et al. Anticholinesterase, antioxidant, analgesic and anti-inflammatory activity assessment of Xeranthemum annuum L. and isolation of two cyanogenic compounds. Pharm Biol 2016;54:2643–51.
  • Hegazy M-EF, Ibrahim AY, Mohamed TA, et al. Sesquiterpene lactones from Cynara cornigera: acetyl cholinesterase inhibition and in silico ligand docking. Planta Med 2016;82:138–45.
  • Ercetin T, Senol FS, Erdogan Orhan I, et al. Comparative assessment of antioxidant and cholinesterase inhibitory properties of the marigold extracts from Calendula arvensis L. and Calendula officinalis L. Ind Crops Prod 2012;36:203–8.
  • Szwajgier D. Anticholinesterase activity of selected phenolic acids and flavonoids – interaction testing in model solutions. Ann Agric Environ Med 2015;22:690–4.