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Isoflavonoids from the Rhizomes of Iris Hungarica and Antibacterial Activity

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Isoflavonoids from the Rhizomes of Iris Hungarica and Antibacterial Activity Isoflavonoids from the rhizomes of Iris hungarica and antibacterial activity of the dry rhizomes extract Isoflavonoides de los rizomas deIris hungarica y actividad antibacteriana del extrac- to de rizomas seco Olga Mykhailenko1, Volodumur Kovalyov2, Sergiy Kovalyov3 , Anastasiia Krechun2 1Department of Botany, National University of Pharmacy, Kharkiv, Ukraine. 2Department of Pharmacognosy, National University of Pharmacy, Kharkiv, Ukraine. 3Department of nutritiology and pharmaceutical bromatology, National University of Pharmacy, Kharkiv, Ukraine Artículo Original ABSTRACT http://dx.doi.org/10.4321/S2340-98942017000100005 Original Article Aim: The aim of the work was isolation and identification of the phenolic compounds from the rhizomes of Iris hungarica. Correspondencia Correspondence Materials and methods: To establish by chemical and spectral methods for the structures of phenolic Olga Mykhailenko compounds, which were isolated from the rhizomes of Iris hungarica Waldst. et Kit. (Iridaceae family). e-mail: [email protected] Compounds were obtained by column chromatography on silica gel and their structures were deter- mined by UV, IR, MS, 1H-NMR spectra methods. Preliminary screening of antibacterial activity was Agradecimientos Acknowledgments determined. The authors would like gratitude to Results: From the ethanolic extract of the rhizomes of I. hungarica, which is widespread in Ukraine, for acting as a Head of the Laboratory of Biochemistry of Microorganisms and the first time two new for this species isoflavones, teсtorigenin and tectoridin and xanthone mangiferin, Nutrient Media of the State Institution together with known isoflavonoids daidzein, genistein, formononetin were isolated. The dry extract “Institute of Microbiology and Immuno- of the rhizomes of I. hungarica at a concentration of 1% has shown the highest inhibitory activity for logy named after I.I. Mechnikov of the Gram-positive bacteria and fungi. National Academy of Medical Sciences of Ukraine,” Cand. Med. Sci. T.P. Osolo- Keywords: isoflavonoids; teсtorigenin; tectoridin; mangiferin; Iris hungarica; antibacterial activity. dchenko for the preliminary screening of antimicrobial activities and a Head of RESUMEN Department of the Ornamental plants, Senior Researcher of the National Objetivo: El objetivo del trabajo es el aislamiento y la identificación de los compuestos fenólicos de los Botanical Garden n.a. M.M. Gryshko of rizomas de Iris hungarica. NAS of Ukraine (Kyiv), Cand. Biol. Sci. Yu.V. Buidin for help in systematical Materiales y métodos: Se utilizaron métodos químicos y espectrales para conocer las estructuras de com- classification of plants. puestos fenólicos que se aislaron de los rizomas de Iris hungarica Waldst. et Kit. (Familia de Iridaceae). Los compuestos se obtuvieron mediante cromatografía en columna sobre gel de sílice y se determinaron Conflicto de interés Competing interest sus estructuras mediante análisis de sus espectros por UV, IR, MS, 1H-RMN. Se determinó el cribado The author have declared that no finan- preliminar de la actividad antibacteriana. cial relationships with any organizations Resultados: Se aislaron por primera vez de los rizomas de Iris hungarica (común en Ucra- that might have an interest in the sub- mitted work; nor any other relationships nia) dos isoflavonas, teсtorigenina y tectoridina (nuevas para esta especie), el xan- or activities that could appear to have tonoide mangiferina y los isoflavonoides daidzeina, genisteina y formononetina. influenced the submitted work. El extracto seco de los rizomas de I. hungarica a una concentración de 1% ha mostrado la actividad inhib- itoria más alta para bacterias y hongos Gram-positivos. Received: 06.03.2017 Accepted: 17.03.2017 Palabras claves: isoflavonoides; teсtorigenina; tectoridina; mangiferina; Iris hungarica; actividad anti- bacteriana. INTRODUCTION Iris hungarica Waldst. et Kit. (syn. Iris aphylla L.) is a perennial rhizomatous plant, growing to 30 cm high with a long rhizome belong to the family Iridaceae and widely distributed in most parts of the world1. Geographical distribution in Europe2,3: Spain, Czech Republic, France, Germany, Hungary, Italy, Poland, Romania, Ukraine4,5. LICENSE 3.0 UNPORTED. Ars Pharm. 2017; 58(1): 39-45 39 Olga Mykhailenko, Volodumur Kovalyov, Sergiy Kovalyov , Anastasiia Krechun Previous phytochemical investigations of the Iris plants MATERIALS AND METHODS have resulted in the isolation of a variety of compounds in- General experimental procedure cluding flavonoids6, isoflavones (irigenin, nigricin, irisflor- entin, iriskumaonin, irilon, iriflogenin, etc.)7 and their gly- ¹Н-NMR spectra (200 MHz) were recorded on a Varіan Mer- 8 9 10 cosides; C-glucosylxanthones , quinones , triterpenoids , cury-VX-200 in DMSO-d6 with TMS as an internal standard. stilbene glycosides11. The rhizomes of irises also contain Low-resolution mass spectra were measured on a GC–MS carbohydrates, fatty oil, organic acids, tannins and essential Varian 1200L (ionizing voltage 70 eV) instrument. UV spec- oil, which is used in perfumery and cosmetics12,13, while the tra were recorded on a Carl Zeіss Specord M-80 in EtOH. leaves are a source of ascorbic acid and vitamins11. IR spectra were recorded on a Tensor 27 UR-20 spectropho- tometer. Column chromatography (CC) was carried out on The dried rhizomes of iris has been used in folk medicine silica gel 75 – 150 mesh. Chromatographic testings were of European countries as a diaphoretic for bronchitis, in carried out on pre-coated thin-layer chromatography (TLC) dental practice – in order to accelerate teething in infants; plates (silica gel 60 F254 Merck, Silufol UV254) and paper Fil- as anti-inflammatory for the treatment of pancreatic and trak. Compounds on the TLC plates were detected by the 8,14 salivary glands, and the vegetative neurosis . The iris es- characteristic fluorescence in UV-light at the wavelength 10,13 sential oil has expectorant properties . The compounds 365 and 254 nm before and after ammonium vapours, 2% 8 isolated from iris species have piscicidal, antineoplastic , alcoholic solution of aluminium chloride as a spraying rea- 15,16 17 antiplasmodial, antituberculosis , antioxidant , antimi- gent. Melting point (°C) was determined on a Kofler block. 18 crobial, anti-tumor effects. The recrystallization of selected substances was carried out in 96% ethanol with addition 2-3 drops of water. The sub- The literature data analysis of the chemical composition stances were dried under vacuum (10-2 mm Hg) over P O of the rhizomes of I.hungarica has shown that the plant is 2 5 at 110 – 115°C for 5 h. almost not studied. Thus, the aim of the work was the iso- lation and identification of phenolic compounds from the Plant Material rhizomes of I. hungarica (Figure 1). The rhizomes of Iris hungarica Walds. et Kit. were collected from M.M. Gryshko National Botanical Garden of the National Academy of Sciences of Ukraine, Kiev, Ukraine, in May of 2015 and were air-dried. The plant material com- plies with the description of the Flora Ukraine4. Voucher specimens have been deposited in the Herbarium of the Pharmacognosy Department and Botany Department, National University of Pharmacy, Kharkiv, Ukraine. Extraction and isolation of compounds Air-dried rhizomes of I. hungarica (1.0 kg) were extracted with ethanol (EtOH) (70%, 5 L) in a percolator for 24 h19,20. The extraction was repeated thrice under the same condi- tions. The aqueous EtOH extracts were combined, filtered, evaporated in a rotary evaporator to 0.5 L of aqueous res- idue, and left for 1 d. The supernatant liquid was separat- ed. The resulting extract was worked up successively with a chloroform (CHCl3), ethyl acetate (EtOAc), and butanol (n-BuOH). The resulting extracts were evaporated in vac- uum. The qualitative composition of CHCl3, EtOAc and BuOH fractions controlled by paper and thin-layer chroma- tography in a solvent system butanol – acetic acid – water (BuOH – HAc – H2O) (4:1:2) (Rf1) and chloroform – metha- nol (CHCl3 – MeOH) (9:1) (Rf2). b For further analysis the acid hydrolysis of sum of the phe- nolic compounds was conducted with 5% H SO (2 ml) for Figure 1. General view (a) of the living plants and raw 2 4 materials (b) of I. hungarica 5 h in the water bath. The solution was neutralized with Na2CO3 and extracted with EtOAc. Analysis of the sub- 40 Ars Pharm. 2017; 58(1): 39-45 Isoflavonoids from the rhizomes of Iris hungarica and antibacterial activity of the dry rhizomes extract stances was carried out by paper (PC) and (TLC) . By the 3726, 3410, 3104 (-ОН), 1651 (С=О), 1615, 1569, 1424, 1503 1 characteristic fluorescence in UV-light, fR value and colour (С=С), 885 (n-substitution in the ring „B“). H-NMR (200 of spots on chromatograms after they were exposed to am- MHz, DMSO-d6) δ, ppm: 10.75 (1H, s, 7-OH), 8.42 (1H, s, monia vapors in comparison with authentic samples and 2-Н), 6.72 (1H, dd, J = 1.7 Hz, 6-Н), 6.47 (1H, d, J = 1.7 Hz, literature data were identified as daidzein, formononetin, 8-H), 7.40 (2H, d, J = 8.5 Hz, H-2′, 6′), 6.83 (2H, d, J = 8.5 Hz, genistein21,22. H-3′, 5′), 9.64 (s, OH-4′), 12.94 (1H, s, OH-5). EtOAc extract was evaporated by heating under vacuum Daidzein (5) C15H10O4, amorphous powder, m.p. 320-322 + to complete stripping of solvent and subjected to CC (80×4 °C. М 254.24 g/mol. MS, m/z: 254 (М ). Rf1 0.88, blue; UV −1 cm) on silica gel and eluted with gradient: CHCl3 and eth- λmax (C2H5OH) nm: 250, 260sh, 302. IR (KBr), ν, cm : 3666, anol-mixtures with increasing ethanol concentration (0- 3171 (-ОН), 1631 (С=О), 1595, 1518, 1188, 1460 (С=С), 887, 100%) to afford 50 fractions. Compound 1 (80 mg) detected 820 (n-substitution in the ring “B”). 1H-NMR (200 MHz, in fractions of chloroform-ethanol (9:1), compound 2 (85 DMSO-d6) δ, ppm: 10.80 (1H, s, 7-OH), 9.60 (s, OH-4′), 8.31 mg) – chloroform-ethanol (8:2) and compound 3 (100 mg) – (1H, s, 2-Н), 8.05 (1H, d, 5-H), 7.14 (1Н, dd, J = 1.7 Hz, 6-Н), chloroform-ethanol (5:1).
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