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Hydroxytyrosol EJOHG Rengin Reis et al. 10.5005/jp-journals-10018-1278 RESEARCH ARTICLE Hydroxytyrosol: The Phytochemical Responsible for Bioactivity of Traditionally used Olive Pits 1,2Rengin Reis, 1Hande Sipahi, 1Gülşah Zeybekoğlu, 1Nur Çelik, 3Hasan Kırmızıbekmez, 4Neşe Kaklıkkaya, 1Ahmet Aydın 1Department of Toxicology, Yeditepe University, Istanbul, Turkey, 2Department of Toxicology, Karadeniz Technical University, Trabzon, Turkey, 3Department of Pharmacognosy, Yeditepe University, Istanbul, Turkey, 4Department of Microbiology, Karadeniz Technical University, Trabzon, Turkey ABSTRACT The fruits of Olea europaea L. is widely consumed as food, and olive pits are utilized in folk medicine to relieve gastric disturbances. In the present study, the possible anti-inflammatory, analgesic and antioxidant activities of aqueous extracts of black (BP) and green olive (GP) pit prepared at gastric fed state pH were evaluated in vitro. Moreover, the bioactive compound, hydroxytyrosol (HT), was isolated from the extracts for the first time. According to results, GP extract (62.5 to 1000 µg/mL) showed significant anti-inflammatory activity in a dose-dependent manner and HT displayed significant nitrite inhibition at 100 µM with slight analgesic activity. Extracts and HT showed a significant antioxidant activity according to Total Antioxidant Capacity (TOAC), cupric ion reducing antioxidant capacity (CUPRAC), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assays. As a conclusion, a proper formulation containing HT might be a potential remedy to relieve gastric disturbances and olive pits, can be utilized as a valuable industrial tool for the low-cost production of HT. Keywords: Analgesic, Anti-inflammatory, Hydroxytyrosol, Nitric oxide, Olea europaea, Olive pit. How to cite this article: Reis R, Sipahi H, Zeybekoğlu G, Çelik N, Kırmızıbekmez H, Kaklıkkaya N, Aydın A. Hydroxytyrosol: The Factor Responsible for Bioactivity of Traditionally used Olive Pits. Euroasian J Hepatogastroenterol, 2018;8(2):126-132. Source of support: This research is financially supported by the Scien tific and Technological Research Council of Turkey (TUBITAK) (2209/A). Conflict of interest: None INTRODUCTION effects of Mediterranean diet4,6 or as a protector against the development and progression of inflammatory Olive, known as Olea europaea L., is the most popular diseases.6 Over the last decade, ingestion of olive pits member of the Olea genus. Moreover, it is the only species to relieve the symptoms of duodenal ulcer and gastric of the Oleaceae family that is consumed as a food.1 Par- ticularly, olive is found in the Mediterranean region and disturbances has become popular in Turkey following 7 consumed commonly in the Eastern Mediterranean Basin paramedical suggestions. However, ingestion of olive as well as Southeastern Europe, Northern Iran, Western pits may lead to unwanted adverse effects on the gastro- Asia, and Northern Africa.1 Turkey has also an important intestinal system due to the shape and the indigestible 8 potential for olive cultivation because of its geographic structure of the olive pit. According to a case report location and climate.2 According to International Olive from Bulgaria, a patient had totally obstructed his pyloric Council (IOC) report (2015), over the last 25 years, the channel after having swallowed several olive pits to cure 7 growth of olive consumption has been the strongest his peptic ulcer following an ancient Bulgarian belief. In 8 among the non-European Union members, especially in another case report, distal pyloric stenosis perforation Turkey and Morocco.3 Besides its culinary importance, and gastric phytobezoar were observed due to excessive olive is also studied for its therapeutic effects. Indeed, olive pit ingestion. there are many studies investigating the antioxidant, To the best of our knowledge, there is no study that antimicrobial, anti-inflammatory, antidiabetic, laxative, examines the biological activity of olive pits treated at and anticancer properties of the fruit itself4 or its deriva- gastric pH even though ingesting them is a traditional tives such as its leafs,1 or olive oil,5 given its phenolic medical practice in many cultures. This study is the first antioxidant content that has been related to the beneficial to examine the potential effects of olive pits extracts Address reprint request to: Hande Sipahi, Department of Toxicology, Yeditepe University, Istanbul, Turkey. Phone: +90 216 5780000 (3371), e-mail: [email protected], [email protected] 126 EJOHG Hydroxytyrosol: The Phytochemical Responsible for Bioactivity of Traditionally used Olive Pits prepared at gastric fed state pH, which sets a model to enlighten their effect when swallowed. In this study, we aimed to identify the possible anti-inflammatory, analge- sic, antimicrobial, and antioxidant activities of aqueous extracts of black and green olive pits in vitro. Also, the isolation of the main bioactive compound was achieved and the same activity studies were performed for this compound as well. MATERIAL AND METHODS Chemicals, Reagents and Equipment Thin layer chromatography (TLC): SiO2 plates (silica gel 60 F254; Merck) aluminum plates; eluents CH2Cl2-MeOH-H2O (80:20:2), visualization by spraying with 1% vanillin/ Schematic diagram of olive pit extraction and sample o Fig. 1: H2SO4 reagent followed by heating at 105 C for 2 to 3 min. preparation processes. Medium-pressure liquid chromatography (MPLC): Sepa- BP: Black olive pit extract; GP: Green olive pit extract core® Flash Systems X10/ X50 (Büchi),Redi sep columns extraction process, the aqueous extracts were lyophilized (LiChroprep C18, 50 g, Teledyne Isco). Sodium phosphate and kept in -20o C till use. Figure 1 shows the schematic monobasic, copper sulfate and ammonium molybdate diagram of the extraction and sample preparation pro- were from Riedel-de Haën (Germany). Sulfuric acid, cesses. DPPH (2,2-diphenyl-1-picrylhydrazyl), ascorbic acid, LPS (lipopolysaccharide from E.coli 0111:B4), "N-Nitro-L-argi- Isolation and Structure Elucidation of Bioactive nine methyl ester hydrochloride"., sulfanilamide, MTT Compound (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium The crude extract (green olive pit, 100 mg) was applied to and N-(1-naphthyl) ethylenediamine dihydrochloride Medium Pressure Liquid Chromatography (C18-MPLC, were obtained from Sigma Aldrich (USA). Butylated 50 g) eluting with stepwise gradient of MeOH in H2O hydroxytoluene (BHT) was purchased from Doğa Drug (0–30% in steps of 5%) to yield pure hydroxytyrosol (HT, Company (Turkey). Phosphoric acid was from Mettler 3 mg). The structure elucidation was performed by using (Switzerland). Neocuproine was obtained from Santa- 1H NMR (400 MHz) and ESI-MS analysis (Figs 2 and 3). Cruz Biotechnology (USA) and ammonium acetate was from Merck (Germany). Indomethacin and sodium nitrite Cell Culture and Cell Viability were purchased from Fluka Chemika (Germany). For RAW264.7 murine macrophage cells (ATCC, USA) were the cell culture, dulbecco's modified eagle's medium maintained in DMEM, supplemented with 10% FBS (DMEM) from Gibco (England) and fetal bovine serum and 1% streptomycin and penicillin at 37°C in 5% CO2. (FBS), streptomycin and penicillin were used from Gibco Cell viability was examined by using MTT assay. Plated (USA). Prostaglandin E2 Enzyme-linked immunosorbent RAW264.7 cells (106 cells/ mL) were treated with differ- assay (ELISA) Kit was purchased from Abcam (UK). UV- ent concentrations of olive pit extracts (62.5, 125, 250, 500 spectrophotometric plate reader was used from Thermo and 1000 µg/mL) and with the bioactive compound, HT Multiskan Spectrum (Finland). (100µM). After 24 hours incubation process, MTT was Plant Material added to each well at 0.5 mg/mL of concentration and incubated for an additional 2 hours at 37°C. After discard- The fruits of Olea europaea L. (Marmarabirlik) were pur- ing all medium from plates, 100 µl of isopropanol was chased from a local market in Turkey. The representatives added to all wells. Absorbance of the blue formazan was of samples are being kept in our laboratory. determined at 570 nm by a UV-spectrophotometric plate reader (Thermo Multiskan Spectrum, Finland). Viability Preparation of Extracts was defined as the ratio (expressed as a percentage) of 100 g of black olive pits (BP) (135 pits) and green olive absorbance of treated cells to untreated cells and all pits (GP) (113 pits) were extracted separately by using 1 measurements were done in triplicates. L of distilled water which was adjusted to pH 4 with HCl to simulate the fed state of gastric environment at 37o C Evaluation of Anti-inflammatory Activity and then slightly shaken at 300 rpm for 2.5 hours, which Anti-inflammatory activity of olive pit extracts was evalu- is approximate time for gastric emptying.9,10 After the ated by measuring the stable nitric oxide (NO) metabolite, Euroasian Journal of Hepato-Gastroenterology, July-December 2018;8(2):126-132 127 Rengin Reis et al. Fig. 2: 1H-NMR (400 MHz, CD3OD) Spectrum of hydroxytyrosol Fig. 3: ESI-MS Spectrum of hydroxytyrosol. nitrite, with Griess reagent.11 Briefly, RAW264.7 cells were Determination of Total Antioxidant Capacity plated at the density of 106 cell per mL in a 48 well-plate The total antioxidant capacities of samples were per- and incubated for 24 hours at 37°C in 5% CO . Plated 2 formed by applying the slightly modified version of the cells were pre-treated with five different concentrations phosphomolybdenum method described by Celep et al.12 of aqueous extract of olive pit (62.5, 125, 250, 500 and 1000 The assay was based on the reduction of Mo (VI) to Mo µg/mL) for 2 hours and then stimulated with 1 µg/mL of (V) by the antioxidant compounds and the subsequent lipopolysaccharide (LPS) from E. coli 0111:B4, Sigma, USA) formation of a green phosphate/Mo (V) complex at acidic for additional 22 hours. The culture supernatant (50 µL) pH. The reagent solution was consisted of 28 mM sodium was mixed with Griess reagent [1% sulfanilamide and phosphate monobasic, 4 mM ammonium molybdate and 0.1% N-(1-naphthyl)] ethylenediamine dihydrochloride in 0.6 M sulfuric acid.
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