Phenolic, oxylipin and fatty acid profiles of the Chilean hazelnut (Gevuina avellana): Antioxidant activity and inhibition of pro-inflammatory and metabolic syndrome-associated enzymes Liudis Leidy Pino Ramos, Felipe Jiménez-Aspee, Cristina Theoduloz, Alberto Burgos-Edwards, Raúl Domínguez-Perles, Camille Oger, Thierry Durand, Ángel Gil-Izquierdo, Luis Bustamante, Claudia Mardones, et al. To cite this version: Liudis Leidy Pino Ramos, Felipe Jiménez-Aspee, Cristina Theoduloz, Alberto Burgos-Edwards, Raúl Domínguez-Perles, et al.. Phenolic, oxylipin and fatty acid profiles of the Chilean hazelnut (Gevuina avellana): Antioxidant activity and inhibition of pro-inflammatory and metabolic syndrome-associated enzymes. Food Chemistry, Elsevier, 2019, 298, pp.125026. 10.1016/j.foodchem.2019.125026. hal- 02617123 HAL Id: hal-02617123 https://hal.archives-ouvertes.fr/hal-02617123 Submitted on 3 Jun 2021 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Food Chemistry 298 (2019) 125026 Contents lists available at ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem Phenolic, oxylipin and fatty acid profiles of the Chilean hazelnut (Gevuina T avellana): Antioxidant activity and inhibition of pro-inflammatory and metabolic syndrome-associated enzymes Liudis Leidy Pino Ramosa, Felipe Jiménez-Aspeeb, Cristina Theodulozc, Alberto Burgos-Edwardsa, Raúl Domínguez-Perlesd, Camille Ogere, Thierry Durande, Ángel Gil-Izquierdod, Luis Bustamantef, Claudia Mardonesf, Katherine Márquezg, David Contrerasg, ⁎ Guillermo Schmeda-Hirschmanng, a Laboratorio de Química de Productos Naturales, Instituto de Química de Recursos Naturales, Universidad de Talca, Talca, Chile b Departamento de Ciencias Básicas Biomédicas, Facultad de Ciencias de la Salud, Universidad de Talca, Talca, Chile c Laboratorio de Cultivo Celular, Facultad de Ciencias de la Salud, Universidad de Talca, Talca, Chile d Research Group on Quality, Safety and Bioactivity of Plant Foods, Department of Food Science and Technology, CEBAS (CSIC), University Campus of Espinardo, Edif. 25, 30100 Murcia, Spain e Institut des Biomolécules Max Mousseron, IBMM, UMR 5247, University of Montpellier, CNRS, ENSCM, Montpellier, France f Departamento de Análisis Instrumental, Facultad de Farmacia, Universidad de Concepción, Chile g Biotechnology Centre and Chemical Sciences Faculty, University of Concepcion, Concepcion, Chile ARTICLE INFO ABSTRACT Chemical compounds studied in this article: Roasted cotyledons of the Chilean hazelnut (Gevuina avellana) are appreciated as snacks. The aim of our work α-Linolenic acid (PubChem CID: 5280934) was to assess the fatty acid, oxylipin and phenolic composition using gas chromatography (GC) coupled to mass 5-Hydroxymethyl furfural (PubChem CID: spectrometry (MS), ultra- high performance liquid chromatography (UHPLC) coupled to MS and HPLC coupled 237332) to diode array detector (HPLC-DAD). Additionally, various antioxidant activities were assessed. The inhibition of 7-Hexadecenoic acid (PubChem CID: 445639) α-glucosidase, α-amylase, lipase, cyclooxygenases-1 and -2 (COX-1/COX-2), and lipoxygenase was determined. Arachidonic acid (PubChem CID: 444899) The main fatty acids were oleic and 7-hexadecenoic acids. Eight phytoprostanes and three phytofurans were Hydroxybenzoic acid (PubChem CID: 135) Oleic acid (PubChem CID: 445639) identified and quantified. Hydroxybenzoic and hydroxycinnamic acids were the main phenolic compounds. Oils showed antioxidant activity determined by EPR, and inhibition of COX-1/COX-2. The statistical analysis showed Keywords: that the roasting does not affect the composition of the samples. The occurrence of oxylipins in this speciesis Chilean hazelnut reported for the first time. Chilean hazelnuts can be considered a source of health promoting compounds. Gevuina avellana Phenolics Fatty acids Phytoprostanes Phytofurans Polyunsaturated fatty acids HPLC-MS/MS 1. Introduction including coconut (Cocos nucifera), peanut (Arachis hypogea) and the temperate species hazelnut (Corylus avellana), walnut (Juglans spp.) and Several nuts and seeds are relevant for human consumption almonds (Prunus amygdalis var. dulcis) (Gray, 2005). Nuts are Abbreviations: AA, arachidonic acid; ALA, α-linolenic acid; BHT, butylated hydroxytoluene; COX, cyclooxygenase; DPPH, 2,2-diphenyl-1-picrylhydrazyl radical; EPR, electron paramagnetic resonance; FAME, fatty acid methyl ester; FRAP, ferric reducing antioxidant power; GC-MS, gas chromatography-mass spectrometry; HPLC-MS/MS, high performance liquid chromatography coupled to mass spectrometry LOX, 15-lipoxygenase; MUFA, monounsaturated fatty acids; ORAC, oxygen radical absorbance capacity; PBN, N-t-butyl-α-phenylnitrone; PEE, polyphenol-enriched extract; PhytoFs, phytofurans; PhytoPs, phytoprostanes; PUFAs, poly- unsaturated fatty acids; SFA, saturated fatty acids; TEAC, Trolox equivalent antioxidant capacity; TP, total phenolic content ⁎ Corresponding author. E-mail address: [email protected] (G. Schmeda-Hirschmann). https://doi.org/10.1016/j.foodchem.2019.125026 Received 22 January 2019; Received in revised form 10 June 2019; Accepted 15 June 2019 Available online 15 June 2019 0308-8146/ © 2019 Elsevier Ltd. All rights reserved. L.L. Pino Ramos, et al. Food Chemistry 298 (2019) 125026 consumed either raw or roasted. Roasting adds additional organoleptic not been completely demonstrated so far. properties but can also modify the composition of health-promoting While the fatty acid composition of some G. avellana samples has constituents (Taş and Gökmen, 2017; Chang, Alasalvar, Bolling, & been described, there is no information on the occurrence of oxylipins Shahidi, 2016). The Chilean hazelnut Gevuina avellana Mol. is the and polyphenols, neither the potential health benefits from the different southernmost representative of the Proteaceae family, which includes constituents of the nut. In addition, G. avellana cotyledons are roasted the macadamia nut (Macadamia integrifolia and M. tetraphylla). The before consumption, and this thermal process may affect the content genus Macadamia is native to tropical Australia, and is cultivated in and composition of phytochemicals. In the light of the current knowl- Hawaii, tropical Africa and South America (Uquiche, Jeréz, & Ortíz, edge, our hypothesis is that G. avellana nuts are a source of fatty acids, 2008; Gray, 2005). The common name Chilean hazelnut was given to G. oxylipins and polyphenols with potential health promoting activities, avellana due to the morphological similarity with the European ha- which can be affected by the roasting process. The aim of the present zelnut Corylus avellana L. (Betulaceae). work was to gain a further insight in the fatty acid and phenolic com- In Chile, the gathering of G. avellana nuts can be traced back to pre- position of Chilean hazelnuts, as well as the occurrence of PhytoPs and Hispanic times. Remains of de-husked nuts are still frequently found in PhytoFs in this food matrix. In addition, the antioxidant activity, as well archeological sites. Mösbach (1992) described under the Mapuche as the inhibition towards pro-inflammatory and metabolic syndrome- name “gevuin” the tree Gevuina avellana, considered by the natives as associated enzymes was studied. Raw and roasted material was in- the most relevant fruiting tree in their culture. The nuts are collected in cluded to determine if the roasting process affects the content, com- March-April and are stored for the winter time. The fruits are de-husked position and activity of the samples. and the seeds are roasted before consumption. Roasting is a traditional activity performed by small farmers or gatherers that collect and pro- 2. Materials and methods cess the seeds for commercialization. They are obtained from wild stocks of the tree, either at the western Andean slopes or at the coastal 2.1. Chemicals and reagents range (“cordillera de la Costa”). Besides the consumption of roasted seeds, some by-products can be found in traditional markets. The co- 2,2′-Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium tyledons are grinded after mild or medium roasting to obtain a meal salt (ABTS), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxilic acid that is used for pastry products. If the cotyledons are intensively (Trolox), potassium persulfate, sodium carbonate, Folin-Ciocalteu re- roasted, they can be grinded and used as a coffee substitute. Cotyledon agent, acetic acid, FeCl3x6H2O, acetonitrile (ACN), methanol (MeOH), oil is also used for cosmetic purposes (Flores García, Vergara, Forero- chloroform, linolenic acid, BF3, anhydrous Na2SO4, potassium sodium Doria, Guzmán, & Pérez-Camino, 2018). tartrate and formic acid were purchased from Merck (Darmstadt, Most of the work performed so far on the Chilean hazelnut has been Germany). Sodium chloride, potassium phosphate monobasic, sodium focused on the oil extracted from the seeds (Uquiche et al., 2008) and hydroxide were purchased from Scharlau (Barcelona, Spain). Acarbose, the thermal behavior of the oil (Flores García