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Dehydration Process Influences the Phenolic Profile, Antioxidant And Industrial Crops & Products 120 (2018) 97–103 Contents lists available at ScienceDirect Industrial Crops & Products journal homepage: www.elsevier.com/locate/indcrop Dehydration process influences the phenolic profile, antioxidant and T antimicrobial properties of Galium aparine L. ⁎ Sylwia Senioa, Carla Pereiraa, Josiana Vaza, Marina Sokovicb, Lillian Barrosa, , ⁎ Isabel C.F.R. Ferreiraa, a Centro de Investigação de Montanha (CIMO), Instituto Politécnico de Bragança, Campus de Santa Apolónia, 5300-253, Bragança, Portugal b University of Belgrade, Department of Plant Physiology, Institute for Biological Research “Siniša Stanković”, Bulevar Despota Stefana 142, 11000, Belgrade, Serbia ARTICLE INFO ABSTRACT Keywords: Galium aparine L. is a very disseminated plant in temperate zones, commonly known as clivers or bedstraw, Galium aparine L. belonging to the Rubiaceae family and it is traditionally used for its medicinal applications. In this study, G. Dehydration process aparine hydromethanolic extracts and infusions were prepared from air-dried and freeze-dried samples in order Phenolic compounds to assess their phenolic profile, antioxidant, antimicrobial, and cytotoxic properties. All the studied extracts Bioactive properties revealed a similar phenolic profile, but the hydromethanolic extract obtained from the freeze-dried sample presented the highest concentration of phenolic compounds, followed by the respective infusion and the air- dried sample hydromethanolic extract. The major compound detected in the extracts was 5-O-caffeoylquinic acid (from 145 to 163 mg/g extract). Regarding the bioactivity, in general, the extracts presenting higher phenolic concentrations also revealed enhanced bioactive properties. The EC50 values obtained in the antioxidant activity assays ranged from 13.5 to 884 μg/mL, with the freeze-dried sample hydromethanolic extract presenting the highest activity (13.5–555 μg/mL). Similar conclusions could be made in terms of antimicrobial properties, with this extract showing the lowest MIC (1.85–15 mg/mL), MBC (3.75–7.5 mg/mL), and MFC (3.75–20 mg/mL) values. None of the extracts revealed cytotoxicity. The results obtained in this study suggested that G. aparine extracts can be a good source of phenolic compounds with antioxidant and antimicrobial properties. 1. Introduction antioxidants to delay oxidation processes in foodstuffs and biological membranes has recently focused much attention (Lindsey et al., 2002; There are 350,000 plant species in the world, among which about Vlase et al., 2014), which has led to an increased antioxidant assess- 80,000 edible and yet, it is estimated that only about 150 species are ment of many medicinal and food plant species (Abbasi et al., 2015). In cultivated, directly for human consumption or as a feed for animals this matter, the traditional knowledge plays an essential role on the (Füleky, 2009). Numerous plant species that could provide excellent identification of plants that may be useful, however, in many instances sources of foodstuff as part of a balanced diet, pharmaceutical products, most of this knowledge survives in the people’s memory and is now in insecticides, food additives such as colorants and flavourings, or even a danger of disappearing (Fabricant and Farnsworth, 2001; Fennell et al., raw ingredient for the preparation of beverages, remain underutilized 2004; Jyotsna and Katewa, 2016). (Haq, 1993). Galium aparine L. (Rubiaceae), commonly known as clivers or bed- It is well-known that polyphenol-rich foods and beverages may in- straw is a common weed in temperate zones on all continents and in crease plasma antioxidant capacity, and plants are considered rich Europe, it occurs from Portugal in the west to Russia in the east, and sources of these secondary metabolites, with a variety of more than from the UK in the north to Italy in the south (CABI, 2018). It is an 8000 such compounds identified from various plant species (Pandey unwanted and troublesome plant species in cereal, rapeseed and sugar and Rizvi, 2009). Moreover, epidemiological data indicates that the beet fields where it is noted for its detrimental impact on the potential long term consumption of diets rich in plant polyphenols offers a pro- yields (Malik and Born, 1988). Traditionally, G. aparine has enjoyed a tection against the development of cancers, diabetes, osteoporosis, large number of medicinal applications for diverse health conditions. cardiovascular and neurodegenerative diseases (Pandey and Rizvi, Briefly, the whole herb (stem, leaf, flower and seed) has been com- 2009; Young and Woodside, 2001). The ability of these natural monly used as cooling diuretic in fevers and for urinary tract infections, ⁎ Corresponding authors. E-mail addresses: [email protected] (L. Barros), [email protected] (I.C.F.R. Ferreira). https://doi.org/10.1016/j.indcrop.2018.04.054 Received 5 February 2018; Received in revised form 14 March 2018; Accepted 19 April 2018 Available online 07 May 2018 0926-6690/ © 2018 Elsevier B.V. All rights reserved. S. Senio et al. Industrial Crops & Products 120 (2018) 97–103 in skin diseases such as eczema or psoriasis, ulcers, chronic sores, as a 2.3. Phenolic compounds blood purifier i.e., to increase lymphatic flow, to reduce swellings, in- fection and inflammation, or to stop bleeding from wounds (Tobyn The phenolic profile was determined by LC-DAD-ESI/MSn (Dionex et al., 2016). Ultimate 3000 UPLC, Thermo Scientific, San Jose, CA, USA). The lyo- Beyond these applications, in Sweden, roasted seeds of G. aparine philized infusions and hydromethanolic extracts were re-dissolved in were used as a coffee substitute (Malik and Born, 1988) and in Turkey, water and methanol/water mixture (80:20, v/v), respectively, at a young shoots of G. aparine are also eaten roasted (Taskin and Bitis, concentration of 5 mg/mL. Double online detection was used using a 2016) and used to coagulate milk, being known as “yogurt herb” DAD (280, 330, and 370 nm as preferred wavelengths) and in a mass (Aslantürk et al., 2017; Deliorman et al., 2001). Although the herb has spectrometer in negative mode, equipped with an ESI source (Linear Ion long history of its use in phytotherapy, and the contemporary time’s Trap LTQ XL mass spectrometer, Thermo Finnigan, San Jose, CA, USA), herbalists continue to use it as a diuretic, the pharmacological evidence as previously described by Bessada et al. (2016). supporting this efficiency is scarce. According to some reports, this The identification of the phenolic compounds was performed using plant is a source of polyphenols (Moubasher et al., 2016; Vlase et al., standard compounds, when available, by comparing their retention 2014), phytosterols (Mocan et al., 2016), alkaloids, anthraquinones, times, UV–vis and mass spectra; and also comparing the obtained in- saponins (Aslantürk et al., 2017), sesquiterpenoids, squalene, aromatic formation with available data reported in the literature, giving a ten- compounds, higher alkanes (and derivatives), fatty acids, chlorophylls, tative identification, when no standards were available. For quantita- carotenoids and iridoids (Deliorman et al., 2001; Goryacha et al., tive analysis, calibration curves (5–100 μg/mL) for each available 2014). phenolic standard (5-O-caffeoylquinic acid ≥ 99%, p-coumaric In order to establish scientific rationale for the use of G. aparine, the acid ≥ 90%, ferulic acid ≥ 90%, and quercetin-3-O-rutinoside ≥ 99% first aim of this study was to investigate the phenolic profile, anti- HPLC purity, Extrasynthèse, Genay, France) were constructed based on oxidant, antimicrobial and cytotoxic properties of hydromethanolic the UV signal. For the identified phenolic compounds for which a extracts and infusions prepared from this plant species. Furthermore, commercial standard was not available, the quantification was per- since medicinal plants are often dried and sold as semi- and processed formed through the calibration curve of the most similar available products, in this study, a freshly harvested botanical material was standard (Table 1). The results were expressed as mg/g of extract. prepared by air-drying and freeze-drying with the objective of ex- amining the effect of the drying method on the phenolic composition 2.4. Antioxidant activity and bioactive properties of G. aparine. For the antioxidant activity assessment, the lyophilized infusions 2. Material and methods and hydromethanolic extracts were re-dissolved in water and me- thanol/water mixture (80:20, v/v), respectively, at a final concentra- 2.1. Samples and samples preparation tion of 10 mg/mL. These stock solutions were further diluted to perform the bellow described assays. Galium aparine L. (Rubiaceae) was collected at various growth stages in order to prepare a homogeneous sample, in June 2017, from the 2.4.1. DPPH radical-scavenging activity assay campus of the Polytechnic Institute of Bragança, Portugal. The collected DPPH radical-scavenging activity was assessed using BioTek plant material was authenticated by Professor of Botany Carlos Aguiar ELX800 microplate Reader (Bio-Tek Instruments, Inc.; Winooski, USA). and a specimen voucher was deposited in the herbarium of the School The reaction mixture in each of the 96 wells consisted of the infusions of Agriculture, Polytechnic Institute of Bragança (Portugal). and hydromethanolic extracts at different concentrations (30 μL) and − The vegetal material (leaves, stems, flowers and seeds) was sub- methanolic solution (270 μL) containing DPPH radicals (6 × 10 5 mol/ jected to two drying methods, i.e., air-drying (one week, at room L). The mixture was left to stand for 60 min in the dark and at room temperature, in the dark) and freeze-drying (lyophilisation; FeeeZone temperature. The absorbance was measured at 515 nm to assess the 4.5, Labconco, Kansas City, MO, USA). The dried samples were reduced reduction of DPPH radicals, which was calculated as a percentage of to fine and homogeneous powder (∼20 mesh) and stored at room DPPH discolouration using the formula: [(A DPPH − A S)/A DPPH] × 100, temperature, protected from direct light, for further analysis. where A S is the absorbance of the solution containing the sample, and A DPPH is the absorbance of the DPPH solution (Rita et al., 2016).
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