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Chemical Composition and Biological Properties of the Leaf Essential Oil of Tagetes Lucida Cav

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Chemical Composition and Biological Properties of the Leaf Essential Oil of Tagetes Lucida Cav See discussions, stats, and author profiles for this publication at: https://www.researchgate.net/publication/241714317 Chemical Composition and Biological Properties of the Leaf Essential Oil of Tagetes lucida Cav. from Cuba Article in Journal of Essential Oil Research · September 2011 DOI: 10.1080/10412905.2011.9700485 CITATIONS READS 20 819 5 authors, including: Erik L Regalado Jorge Pino Merck & Co. Inc. Food Industry Research Institute, Havana 100 PUBLICATIONS 2,288 CITATIONS 344 PUBLICATIONS 5,362 CITATIONS SEE PROFILE SEE PROFILE Judith Mendiola Martínez Pedro Kourí Tropical Medicine Institute 52 PUBLICATIONS 500 CITATIONS SEE PROFILE Some of the authors of this publication are also working on these related projects: Proteinase inhibitor as antimalarials View project Medicinal plants and natural products View project All content following this page was uploaded by Erik L Regalado on 22 May 2014. The user has requested enhancement of the downloaded file. Chemical composition and biological properties of the leaf essential oil of Tagetes lucida Cav. from Cuba Erik L. Regalado and Miguel D. Fernández Center of Marine Bioproducts, Loma y 37, Havana, C.P. 10400, Cuba Jorge A. Pino* Food Industry Research Institute, Carretera al Guatao km 3½, Havana, C.P. 19200, Cuba. E-mail: [email protected] Judith Mendiola Institute of Tropical Medicine “Pedro Kourí”, P.O. Box 601, Havana, Cuba Olga A. Echemendia Institute Finlay. Ave 27 319805, Havana, C.P.11600, Cuba Abstract The leaf essential oil of Tagetes lucida Cav. (Asteraceae) from Cuba has been obtained by hydrodistillation and analyzed by GC-FID and GC–MS. Forty volatile compounds were identified, of which estragole (96.8%) was the major constituent. The antioxidant capacity of this essential oil was measured by two different in vitro assays (DPPH and TBARS) and significant activities were evidenced. The preliminary screening of its antiplasmodial, antibacterial, antifungal and antiviral activities was carried out against Plasmodium berghei, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Candida albicans, Acinetobacter lwoffi, Enterobacter aerogenes and against strains HHV 1 and HHV 2. The results showed a moderate activity against P. berghei and E. coli. Key Word Index Tagetes lucida, Asteraceae, essential oil composition, estragole, antioxidant capacity, antiplasmodial activity, antimicrobial activity, antiviral activity. Important: This is an uncorrected proof. Please, access to the published version: http://www.tandfonline.com/doi/abs/10.1080/10412905.2011.9700485 Introduction caused by helminthes (6). Moreover, a bibliographic Tagetes lucida Cav. (syn. T. florida Sweet, T. survey of plants for malaria in Latin America (2) reported schiedeana Less.), commonly called Pericón, hierbanís, the use of the dried powdered plant or the plant decoction anís, santa María, Mexican mint marigold, Mexican for the treatment of malaria in Mexico. tarragon, Spanish tarragon, or Texas tarragon, is a Essential oils from aromatic and medicinal plants have perennial herb that grows in dry rocky slopes and woods been known to possess important biological properties, native to Central America and South America and notably antibacterial, antifungal and antioxidant activities. naturalized elsewhere in the tropics and subtropics (1, 2). It Their biological potential depends on their chemical is cultivated commercially in Costa Rica as a spice herb; it composition determined by genotype and influenced by contains an essential oil having an anise-like odor, and the environmental and agronomic conditions (7). The chemical fresh aerial parts of this plant are sold in the supermarket composition of T. lucida volatile oil has been the subject of as a substitute of tarragon (3), which has been very used as previous studies. The major constituents of this volatile oil spice and to preserve meat (4). This species has been were determined to be methyl eugenol (80%) and estragole cultured in Cuba in gardens due to the beauty of its foliage, (12%) in México (8); estragole (45%) and methyl eugenol but it is not common its exploitation for medicinal aims. (20%) in Hungary (9); anethole (23.8%), eugenol (24.3%) T. lucida has been referred in Mexican traditional and estragole (33.9%) in Guatemala (10) or estragole (95- medicine for different therapeutic applications. The 97%) in Costa Rica (3). T. lucida extracts have reported to infusion of leaves and flowers is drunk to combat diarrhea, act on bacteria and phytopathogenic fungi (5) and also rheumatism, asthma, and cold (5, 6). The decoction of the possesses antidepressant-like properties in rats (11). aerial parts is employed in the treatment of amoebic Moreover, considering both thiophene concentrations and dysentery, giardiasis, ascaridiasis and other infections biomass yields, T. lucida appeared to be a promising 2 Tagetes lucida Regalado et al. species, with high potential for use as biocidal crops for substances or literature values (13), relative to C8-C32 n- the implementation of pest control practices (12). alkane series in a temperature-programmed run. In spite of the worldwide use of T. lucida in the folk 2,2-Diphenyl-2-picrylhydrazyl (DPPH) Radical medicine, the biological properties of its essential oil based Scavenging Assay: The antioxidant activity of the on experimental models have remained largely unexplored. essential oil was measured in terms of free-radical In this context, the present work describes a detail scavenging ability according to DPPH reported method chemical composition and examines the antiplasmodial, (14) with minor modifications. Basically, a 60-µM antibacterial, antifungal and antiviral activities of the methanolic solution of DPPH (980 µL) [Sigma-Aldrich essential oil isolated from the leaves of Tagetes lucida Co. (St. Louis, MO), prepared daily, was placed in a Cav. from Cuba. spectrophotometer cuvette, and eight concentrations of the essential oil of 0.1, 0.2, 0.4, 0.8, 1.2, 1.6, 2.0 and 3.0 Experimental mg/mL or ascorbic acid (standard) (0.16, 0.26, 0.6, 1.0 and Plant material: Leaves of T. lucida were collected in 1.30 mg/mL) in methanol (v/v) solution (20 µL) were February 2010, in the medicinal plants field of the Food added. The decrease in absorbance at 515 nm was Industry Research Institute in Havana, Cuba. The plant determined in a UV-1201 spectrophotometer, until the was identified by Dr. Pedro Herrera of the Institute of reaction plateau step was reached. Methanol was used to Ecology and Systematic (IES) and a voucher specimen zero the spectrophotometer. EC50 values were determined was deposited at the Herbarium of IES (HAC 44100). from the plotted graph of scavenging activity against Leaves (200 g) were submitted to hydrodistillation in a sample concentrations, which is defined as the total Clevenger-type apparatus for 2 hours. At the end of each antioxidant necessary to decrease the initial DPPH radical distillation the oils were collected, dried with anhydrous concentration by 50%. Triplicate measurements were Na2SO4, measured, and transferred to glass flasks that were carried out, and their scavenging effect was calculated filled to the top and kept at a temperature of −18°C for based on the percentage of DPPH scavenged. further analysis. Analyses were made by duplicate. Yields TBARS (thiobarbituric acid reactive species) assay: were calculated according to the weights of oils and plant The lipid peroxidation assay as TBARS was carried out material before distillation. according to a modified method (15). The reaction mixture Analysis of the essential oils: Oil sample analyses containing, in a final volume of 1.1 mL, 100 mL of were performed on A Konik 4000A instrument (Barcelona, cerebral tissue (whole brain) and 1 mL (0.05M) of Spain) equipped with a HP-5ms fused silica column (25 m KH2PO4/K2HPO4 buffer, pH 7.4 in NaCl (0.9%), and x 0.25 mm i.d., film thickness 0.25 µm), split injection seven concentrations of the essential oil (20, 50, 100, 150, 1:10, and flame ionization detection. Injector and detector 200, 250 and 500 µg/mL) was incubated at 37°C for 1 h. temperatures were at 220º and 250ºC. The oven Then, 1 ml of thiobarbituric acid (0.5%) and 1 mL of temperature was held at 70ºC for 2 min and then raised to acetic acid (20%) were added to the test tubes and were 250ºC at 4ºC/min and held for 10 min. The carrier gas was incubated at 100°C for 60 min. After cooling, absorbance H2 at 1 mL/min. Samples were injected by splitting and the was measured at 532 nm against control and buffer, BHT split ratio was 1:20. The lineal retention indices (RI) were being used as reference compound. All the experiments obtained from GC by logarithmic interpolation between were performed in triplicate, and the results were bracketing a homologous series of n-alkanes used as averaged. The inhibition percentage was determined by standards. Peak areas were measured by electronic comparison of the results between the samples and control. integration using the EZChrom Chromatography Data Antimalarial assay: In-vitro drug susceptibility was System 6.07 program (Scientific Software, Inc., FL). The determined in the standard short-term cultures of relative amount of the individual components was based Plasmodium berghei ANKA blood stages as described on the peak areas. before (16). Briefly, erythrocytes infected with parasites of GC/MS analysis was performed on a Shimadzu 17A P. berghei ring forms/young trophozoites are incubated at (Tokyo, Japan) gas chromatograph coupled to a Shimadzu 2% parasitemia at a final cell concentration of 1% in QP-5000 high performance quadrupole mass selective complete culture medium (RPMI 1640 with 20% Fetal detector was used. The GC was fitted with a HP-5ms fused Calf Serum, Sigma, St. Louis, MO) containing serial silica column (25 m x 0.25 mm i.d., film thickness 0.25 dilutions of essential oil maximal concentration tested, µm). The GC operating conditions were identical with from 200 µg/mL to 12.5 µg/mL, each in duplicate wells of those described above except that He was used as carrier 96-well culture plates.
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