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Antimycobacterial Activity of Constituents from Foeniculum vulgare Var. Dulce Grown in Mexico
Facultad de Ciencias Químicas, Universidad Autónoma de Nuevo León. Av. Universidad s/n, Ciudad Universitaria, San Nicolás de los Garza, Nuevo León, C.P. 66451, Mexico
Facultad de Medicina, Universidad Autónoma de Nuevo León. Madero y Aguirre Pequeño, Mitras Centro, Monterrey, Nuevo León, C.P. 64460, Mexico
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos. Av. Universidad 1001, Col. Chamilpa, Cuernavaca, Morelos, C.P. 62209, Mexico
* Author to whom correspondence should be addressed.
Received: 21 May 2012; in revised form: 19 June 2012 / Accepted: 19 June 2012 / Published: 13 July 2012
Abstract: Bioassay guided fractionation of an antimycobacterial extract of Foeniculum vulgare var dulce (Apiaceae) led to the isolation and characterization of 5-hydroxyfurano-coumarin. The chemical structure of this compound was elucidated by 1H and 13C (1D and 2D) Nuclear Magnetic Resonance (NMR) spectroscopy. In addition, the active fractions were analyzed by GC-MS and seventy eight compounds were identified; the major compounds were 1,3-benzenediol, 1-methoxycyclohexene, o-cymene, sorbic acid, 2-hydroxy-3-methyl-2-cyclopenten-1-one, estragole, limonene-10-ol and 3-methyl-2-cyclopenten-1-one. Twenty compounds identified in the active fractions were tested against one sensitive and three MDR strains of Mycobacterium tuberculosis using the Alamar Blue microassay. Compounds that showed some degree of antimycobacterial activity against all strains tested were the following: linoleic acid (MIC 100 µg/mL), oleic acid (MIC 100 µg/mL), 1,3-benzenediol (MIC 100–200 µg/mL), undecanal (MIC 50–200 µg/mL), and 2,4-undecadienal (MIC 25–50 µg/mL), the last being the most active compound. To our knowledge, this is the first report of the presence of 5-hydroxy-furanocoumarin in F. vulgare.
Keywords: Foeniculum vulgare (F. vulgare); Mycobacterium tuberculosis; multidrug resistant (MDR); 5-hydroxyfuranocoumarin
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Esquivel-Ferriño, P.C.; Favela-Hernández, J.M.J.; Garza-González, E.; Waksman, N.; Ríos, M.Y.; Camacho-Corona, M.R. Antimycobacterial Activity of Constituents from Foeniculum vulgare Var. Dulce Grown in Mexico. Molecules 2012, 17, 8471-8482.
Esquivel-Ferriño PC, Favela-Hernández JMJ, Garza-González E, Waksman N, Ríos MY, Camacho-Corona MR. Antimycobacterial Activity of Constituents from Foeniculum vulgare Var. Dulce Grown in Mexico. Molecules. 2012; 17(7):8471-8482.
Esquivel-Ferriño, Patricia C.; Favela-Hernández, Juan Manuel J.; Garza-González, Elvira; Waksman, Noemí; Ríos, María Yolanda; Camacho-Corona, María del Rayo. 2012. "Antimycobacterial Activity of Constituents from Foeniculum vulgare Var. Dulce Grown in Mexico." Molecules 17, no. 7: 8471-8482.