Short communication Lipophilization and MS characterization of the main anthocyanins purified from hibiscus flowers Claudia Grajeda-Iglesias a , Erika Salas b,⇑ , Nathalie Barouh c , Bruno Baréa c , Maria Cruz Figueroa-Espinoza a,⇑ a Montpellier SupAgro, UMR 1208 IATE, 2 Place Viala, F-34060 Montpellier, France b Universidad Autónoma de Chihuahua, Facultad de Ciencias Químicas, Circuito Universitario s/n, Campus Universitario N° 2, CP 31125 Chihuahua, Chihuahua, Mexico c CIRAD, UMR 1208 IATE, 2 Place Viala, F-34060 Montpellier, France article info Article history: Received 3 December 2016 Received in revised form 27 February 2017 Accepted 28 February 2017 Available online 1 March 2017 Keywords: Anthocyanins Delphinidin-3-O-sambubioside Cyanidin-3-O-sambubioside Hibiscus sabdariffa Lipophilization abstract Hibiscus sabdariffa flowers represent an interesting source of anthocyanins, one of the most important plant pigments, which are responsible of the intense red color of the calyces, and have potential as nat- ural colorants for food applications. Nevertheless, anthocyanins are highly hydrosoluble and unstable compounds. On this basis, the aim of this work was to increase the lipophilicity of the hibiscus antho- cyanins by lipophilization, in order to obtain amphiphilic colorants, which could be easily incorporated in lipid-rich food matrices. Octanoyl derivatives of delphinidin-3-O-sambubioside and cyanidin-3-O- sambubioside were chemically obtained for the first time, and characterized by means of HPLC-ESI-MS data. Ó 2017 Published by Elsevier Ltd. 1. Introduction Color plays an important role in the appreciation of food qual- ity, influencing food preference and acceptability (Bridle & Timberlake, 1997). Thus, the interest to have natural colorants which can be effectively incorporated in food and related products, has prompted the study of the available sources of these com- pounds, and the research for optimal techniques for their extrac- tion and possible transformation to enhance their use. Since anthocyanins are considered as the most important hydrosoluble pigments from vegetal sources (Bridle & Timberlake, 1997), their potential use as colorants in food and cosmetic prod- ucts is being exhaustedly studied. Nevertheless, anthocyanins are highly unstable compounds, and their color properties depend on factors such as concentration, pH variations, temperature, and the presence of other compounds (phenolic acids, metals) (Brouillard, 1982); moreover, they are poorly soluble in organic solvents (Cruz, Fernandes, Araujo, Mateus, & de Freitas, 2015). As a conse- quence, their incorporation in lipid-rich matrices, such as many food products and formulations, is limited. Thus, with the objective to increase the lipophilicity of this major group of natural colorants, lipophilization was used as an innovative tool to transform polar molecules into more hydrophobic ones. Lipophilization consist on the esterification of a lipophilic moiety (fatty acid or fatty alcohol) on different substrates (phenolic acid, sugar, protein...), resulting in new molecules with modified hydrophilic/lipophilic balance (Villeneuve, 2007). The interest of this reaction is to modify and/ or to enhance the functional properties of the original compound, and to facilitate its incorporation into emulsified or lipid-based media (Figueroa-Espinoza & Villeneuve, 2005). Lipophilization has been successfully applied on different phe- nolic compounds, particularly phenolic acids such as chlorogenic, rosmarinic, caffeic, and protocatechuic acid (Grajeda-Iglesias, Salas et al., 2016; Lecomte, Giraldo, Laguerre, Baréa, & Villeneuve, 2010; López Giraldo et al., 2007; Sørensen et al., 2014), to obtain a series of amphiphilic molecules, known as phenolipids, which, depending on the length of the esterified alkyl chain, showed improved antioxidant properties. Also, the chemical and enzymatic acylation of flavonoids with various fatty acids has been patented (Chebil, Humeau, Falcimaigne, Engasser, & Ghoul, 2006). Further- more, the chemical lipophilization of malvidin-3-O-glucoside (Mv-glc), isolated from Porto red wine, was for the first time reported by Cruz et al. (2015). According to these authors, the stearoyl mono- and diesters of Mv-glc, being more hydrophobes than their precursor, could easily be used in food and cosmetic formulations. To our knowledge, this is the first work that describes the chemical lipophilization of the main anthocyanins isolated from http://dx.doi.org/10.1016/j.foodchem.2017.02.140 0308-8146/Ó 2017 Published by Elsevier Ltd. ⇑ Corresponding authors. E-mail addresses: esalas@uach.mx (E. Salas), maria.figueroa@supagro.fr (M.C. Figueroa-Espinoza). Food Chemistry 230 (2017) 189–194 Contents lists available at ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem