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Chemical Composition of Hexane Extract of Citrus aurantifolia and Anti-Mycobacterium tuberculosis Activity of Some of Its Constituents
Facultad de Ciencias Químicas, Universidad Autónoma de Nuevo León, Av. Universidad S/N, Ciudad Universitaria, San Nicolás de los Garza CP 66451, Nuevo León,Mexico
Facultad de Medicina, Universidad Autónoma de Nuevo León, Madero y Aguirre Pequeño, Mitras Centro, Monterrey CP 64460, Nuevo León, Mexico
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Chamilpa, Cuernavaca CP 62209, Morelos, Mexico
* Author to whom correspondence should be addressed.
Received: 10 August 2012; in revised form: 12 September 2012 / Accepted: 12 September 2012 / Published: 19 September 2012
Abstract: The main aim of this study was to isolate and characterize the active compounds from the hexane extract of the fruit peels of Citrus aurantiifolia, which showed activity against one sensitive and three monoresistant (isoniazid, streptomycin or ethambutol) strains of Mycobacterium tuberculosis H37Rv. The active extract was fractionated by column chromatography, yielding the following major compounds: 5-geranyloxypsoralen (1); 5-geranyloxy-7-methoxycoumarin (2); 5,7-dimethoxycoumarin (3); 5-methoxypsoralen (4); and 5,8-dimethoxypsoralen (5). The structures of these compounds were elucidated by 1D and 2D NMR spectroscopy. In addition, GC-MS analysis of the hexane extract allowed the identification of 44 volatile compounds, being 5,7-dimethoxycoumarin (15.79%), 3-methyl-1,2-cyclopentanedione (8.27%), 1-methoxy-ciclohexene (8.0%), corylone (6.93%), palmitic acid (6.89%), 5,8-dimethoxypsoralen (6.08%), a-terpineol (5.97%), and umbelliferone (4.36%), the major constituents. Four isolated coumarins and 16 commercial compounds identified by GC-MS were tested against M. tuberculosis H37Rv and three multidrug-resistant M. tuberculosis strains using the Microplate Alamar Blue Assay. The constituents that showed activity against all strains were 5 (MICs = 25–50 mg/mL), 1 (MICs = 50–100 mg/mL), palmitic acid (MICs = 25–50 mg/mL), linoleic acid (MICs = 50–100 mg/mL), oleic acid (MICs = 100 mg/mL), 4-hexen-3-one (MICs = 50–100 mg/mL), and citral (MICs = 50–100 mg/mL). Compound 5 and palmitic acid were the most active ones. The antimycobacterial activity of the hexane extract of C. aurantifolia could be attributed to these compounds.
Keywords: Citrus aurantifolia; Mycobacterium tuberculosis; multidrug resistant; coumarins; fatty acids; GC-MS analysis
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Sandoval-Montemayor, N.E.; García, A.; Elizondo-Treviño, E.; Garza-González, E.; Alvarez, L.; del Rayo Camacho-Corona, M. Chemical Composition of Hexane Extract of Citrus aurantifolia and Anti-Mycobacterium tuberculosis Activity of Some of Its Constituents. Molecules 2012, 17, 11173-11184.
Sandoval-Montemayor NE, García A, Elizondo-Treviño E, Garza-González E, Alvarez L, del Rayo Camacho-Corona M. Chemical Composition of Hexane Extract of Citrus aurantifolia and Anti-Mycobacterium tuberculosis Activity of Some of Its Constituents. Molecules. 2012; 17(9):11173-11184.
Sandoval-Montemayor, Nallely E.; García, Abraham; Elizondo-Treviño, Elizabeth; Garza-González, Elvira; Alvarez, Laura; del Rayo Camacho-Corona, María. 2012. "Chemical Composition of Hexane Extract of Citrus aurantifolia and Anti-Mycobacterium tuberculosis Activity of Some of Its Constituents." Molecules 17, no. 9: 11173-11184.