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Myrcianthes Pungens Leaf Essential Oil BOLETIN LATINOAMERICANO Y DEL CARIBE DE PLANTAS MEDICINALES Y AROMÁTICAS © / ISSN 0717 7917 / www.blacpma.ms-editions.cl Artículo Original / Original Article Antioxidant and antibacterial activity of Myrcianthes pungens leaf essential oil [Actividad antioxidante y antibacteriana del aceite esencial de hoja de Myrcianthes pungens] Renan Almeida de Jesus1, Herika Line Marko de Oliveira1, Wanessa de Campos Bortolucci1, Caio Franco de Araújo Almeida Campo2, Maria Graciela Iecher Faria1, José Eduardo Gonçalves2, Nelson Barros Colauto1, Zilda Cristiani Gazim1 & Giani Andrea Linde1 1Programa de Pós-Graduação em Biotecnologia Aplicada à Agricultura. Universidade Paranaense, Umuarama, PR, Brasil 2Mestrado em Tecnologia Limpas e Instituto Cesumar de Ciência, Tecnologia e Inovação, UniCesumar, Maringá, PR, Brasil Abstract: Myrcianthes pungens (Myrtaceae) is a native tree to Brazil known as guabijú. In our study, we Reviewed by: described the chemical composition of the essential oil from M. pungens dried leaves, the antioxidant Daniela Russo activity by different methods and antibacterial activity against Staphylococcus aureus, Bacillus cereus Basilicata University and Pseudomonas aeruginosa. The chemical identification was done by gas chromatograph coupled to Italy mass spectrometer and antibacterial activity was evaluated by broth microdilution method. The leaf essential oil presented hydrocarbon sesquiterpenes (42.6%) as its main chemical class whose major Claudio Olea compounds were β-caryophyllene (11.7%) and 1,8-cineole (10.1%). The best antioxidant protection was Universidad de Chile from 57.5 to 63.3% of β-carotene. The highest antibacterial activity was against S. aureus (MIC of 78.12 Chile µg/mL). This value was 2.56-fold lower than the positive streptomycin control. M. pungens is a promising source of natural molecules with potential study for the development of pharmacological, cosmetic and food products. Correspondence: Keywords: β-caryophyllene; 1,8-cineole; β-carotene/linoleic acid co-oxidation; Sesquiterpenes; Guabijú; Giani Andrea LINDE Myrtaceae. [email protected] Section Biological activity Received: 13 September 2019 Resumen: Myrcianthes pungens (Myrtaceae) es un árbol nativo de Brasil conocido como guabijú. En Accepted: 19 November 2019 Accepted corrected: 28 April 2020 nuestro estudio, describimos la composición química del aceite esencial de las hojas secas de M. pungens, Published: 30 March 2021 la actividad antioxidante por diferentes métodos y la actividad antibacteriana contra Staphylococcus aureus, Bacillus cereus y Pseudomonas aeruginosa. La identificación química se realizó mediante un cromatógrafo de gases acoplado a un espectrómetro de masas y la actividad antibacteriana se evaluó mediante un método de microdilución en caldo. El aceite esencial de la hoja presentó sesquiterpenos de hidrocarburos (42,6%) como su principal clase química cuyos compuestos principales fueron β- Citation: cariofileno (11,7%) y 1,8-cineol (10,1%). La mayor protección antioxidante fue de 57.5 a 63.3% de β- de Jesus RA, de Oliveira HLM, Bortolucci WC, Campo CFAA, Faria MGI, Gonçalves JE, caroteno. La mayor actividad antibacteriana fue contra S. aureus (MIC de 78.12 µg/mL). Este valor fue Colauto NB, Gazim ZC, Linde GA. 2,56 veces menor que el control positivo de estreptomicina. M. pungens es una fuente prometedora de Antioxidant and antibacterial activity of moléculas naturales con potencial estudio para el desarrollo de productos farmacológicos, cosméticos y Myrcianthes pungens leaf essential oil. alimenticios. Bol Latinoam Caribe Plant Med Aromat 20 (2): 147 - 161 (2021). Palabras clave: β-Cariofileno; 1,8-Cineol; Co-oxidación de β-Caroteno/Ácido linoleico; Sesquiterpenos; https://doi.org/10.37360/blacpma.21.20.2.12 Guabijú; Myrtaceae. 147 de Jesus et al. Biological actyivity of Myrcianthes pungens essential oil INTRODUCTION instead of a single yearly fruit harvest. Thus, this The most utilized synthetic antioxidants such as BHA study aimed to characterize the chemical composition (butyl hydroxyl anisole), BHT (butylated hydroxyl of the essential oil from M. pungens leaves and toluene), and TBHQ (tertiary butyl hydroquinone) evaluate its antioxidant and antibacterial activity for have molecules that are capable of stabilizing free potential applications in the food, pharmaceutical and radicals and preventing the initiation of oxidation cosmetic industries. chains (Yehye et al., 2015). However, they can also exhibit a pro-oxidant behavior at high concentrations, MATERIAL AND METHODS causing molecule reduction and inducing the Biological material oxidative process (Marin et al., 2008; Škrovánková et Myrcianthes pungens can be found at latitude al., 2012). These compounds have also been 24°59'17.2"S and longitude 53°28'00.4"W; its leaves associated to adverse effects such as carcinogenesis were collected in April 2017, from 7h to 9h o’clock and damages to the liver and lungs (Suh et al., 2005). in the morning, in the vegetative phase, and dried in Food and cosmetics consumers have valued products the shade at ambient temperature (~30°C) for 10 without the addition of synthetic preservatives. Food days. The plant was identified and deposited in the spoilage is a serious widely neglected problem, herbarium of Maringá State University under the mainly in grain due to poor harvesting practices, registration HUEM-32695, and registered in the inappropriate drying, handling, packaging, storage, National System for the Management of Genetic and transport conditions. The utilization of synthetic Heritage and Associated Traditional Knowledge antibiotics or chemicals has increased microorganism (SisGen, acronym in Portuguese) under the resistance, mostly against antibiotics and the search registration AA3F7DB. for new antimicrobials is an alternative to reduce synthetic chemicals uses to extend shelf life and Essential oil extraction prevent foodborne pathogens (Anyanwu & Okoye, The essential oil was extracted from leaves that were 2017). Plant essential oils are a source of new dried and ground in a mixer with ultrapure water and molecules and from 1981 to 2010 approximately one submitted to hydrodistillation in a modified third of the drugs approved by FDA (Food and Drug Clevenger for 2 h (Apel et al., 2006). The essential Administration from United States of America) were oil was dehydrated by filtration in anhydrous sodium from plant molecules (Newman & Cragg, 2012). sulfate, stored in an amber flask and kept under Myrcianthes pungens (Berg) C. D. Legrand refrigeration. and its synonyms Acreugenia pungens (Berg) Kausel, The leaf essential oil yield was calculated by Eugenia pungens Berg, Eugenia ybaviyu Parodi, and the essential oil mass divided by the dried leaf mass, Luma pungens (Berg) Herter (Hassler, 2019), multiplied by 100 and expressed in percentage. The popularly known as guabijú and guabirá (in essential oil density was determined at 20°C in 5.0 Portuguese) is geographically distributed in Brazil, µL graduated capillaries (mass/volume). The Paraguay, Bolivia, Uruguay, and Argentina. It is an refraction index was determined by refractometer evergreen tree with up to 25 m height and round (Abbe RL3 model) calibrated with ultrapure water canopy, light reddish and smooth trunk. Its bright (refraction index of 1.3330) at 20°C (Farmacopeia dark green petiolate leaves have pointed end and Brasileira, 2010). rounder base, measuring from 3.5 to 7.6 cm length and from 1.4 to 3.4 cm width. Its fruits are sweet, Identification of chemical compounds round and smooth with 1-cm diameter average, and Sample of 1 µL dichloromethane (HPLC degree) they have dark purplish color when ripe (Marin et al., with essential oil (20 mg/mL) was used for each 2008). M. pungens leaves have essential oil (Zygadlo analysis. The chemical identification carried out by et al., 1997; Apel et al., 2006), but they have been gas chromatograph (Agilent 7890B) coupled to a little studied, differently from fruits which are edible mass spectrometer (GC-MS) (Agilent 5977A MSD) and present antioxidant activity (Andrade et al., and a HP5-MS UI Agilent fused silica capillary 2011), reduce hypercholesterolemia induced by column (30 × 250 × 0.25 µm; Agilent Technologies), cisplatin in rats (Nora et al., 2014), and with initial oven temperature from 80°C (1 min), antichemotactic activity (Andrade et al., 2011). followed by increased to 185°C at 2°C/min and Moreover, the utilization of leaves is more maintained for 1 min, followed by an increase to sustainable and economically viable than fruits due to 275°C at 9°C/min and maintained for 2 min and the possibility of collecting them throughout the year finally increased to 300°C at 25°C/min and Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas/148 de Jesus et al. Biological actyivity of Myrcianthes pungens essential oil maintained for 1 min. Helium was utilized as the time until 120 min. Trolox (6-hydroxy-2,5,7,8- carrier gas at the linear speed of 1 mL/min up to tetramethylchroman-2-carboxylic acid) was utilized 300°C, and pressure release of 56 kPa. The injector as a reference at 100 µg/mL. The results were temperature was 280ºC; the injection volume was 1 expressed in absorbance reduction along the reaction µL; the injection occurred in split mode (2:1). The time. The β-carotene bleaching rate was calculated temperatures of the transfer line, ion source and according to Equation No. 1. quadrupole were 280ºC, 230ºC and 150ºC. The EM detection system was utilized in “scan” mode, at the R = ln (a/b)/t mass/charge rate/load (m/z) of 40-600, with “solvent delay” of 3 min. The compounds were identified by where R = bleaching rate of β-carotene in the comparing the mass spectra found in NIST 11.0 mixture; ln = natural log; a = absorbance in zero libraries and by comparing the retention index (RI) time; b= absorbance in t time (t = 0, 5, 10, ... 120 obtained by a homologous series of n-alkane standard min). (C7-C28) (Adams, 2012). The antioxidant activity was calculated Antioxidant activity according to the percentage of inhibition in relation 2,2-diphenyl-1-picrylhydrazyl (DPPH•) method to the control, using Equation No.
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