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Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity
Laboratory of Microbiology, Biomedical Research Center of the South (IMSS), Argentina 1, Col. Centro, 62790 Xochitepec, Morelos, Mexico
Center for Development of Biotic Products(IPN), Carretera Yautepec-Jojutla, Km. 6, Calle Ceprobi 8, Col San Isidro, Apdo. Postal 24, 62731 Yautepec, Morelos, Mexico
Chemical Research Center, University of Morelos (UAEM), Av. Universidad 1001, Col. Chamilpa, 62209 Cuernavaca, Morelos, Mexico
Immunochemistry Laboratory II, Department of Immunology, National School of Sciences Biology (IPN), Prolongación Carpio y Plan de Ayala S/N, 11340, D.F., Mexico
* Author to whom correspondence should be addressed.
Received: 11 May 2012; in revised form: 5 July 2012 / Accepted: 5 July 2012 / Published: 12 July 2012
Abstract: Biotransformation processes have been successfully utilized to obtain products of pharmaceutical, chemical, food, and agricultural interest, which are difficult to obtain by classic chemical methods. The compound with antituberculous activity, 9-methoxy-tariacuripyrone (1), isolated from Aristolochia brevipes, was submitted to biotransformation with the yeast Saccharomyces cerevisiae under culture, yielding 5-amino-9-methoxy-3,4-dihydro-2H-benzo[h]chromen-2-one (2). The structure of 2 was elucidated on the basis of spectroscopic analyses. The results mainly show the reduction of the double bond and the nitro group of compound 1. Metabolite 2 demonstrated an increase in anti-tuberculous activity (MIC = 3.12 µg/mL) against the drug-sensitive Mycobacterium tuberculosis (H37Rv) strain, with respect to that shown by 1.
Keywords: biotransformation; Saccharomyces cerevisiae; 9-methoxytariacuripyrone; antituberculous activity
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Alvarez-Fitz, P.; Alvarez, L.; Marquina, S.; Luna-Herrera, J.; Navarro-García, V.M. Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity. Molecules 2012, 17, 8464-8470.
Alvarez-Fitz P, Alvarez L, Marquina S, Luna-Herrera J, Navarro-García VM. Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity. Molecules. 2012; 17(7):8464-8470.
Alvarez-Fitz, Patricia; Alvarez, Laura; Marquina, Silvia; Luna-Herrera, Julieta; Navarro-García, Víctor Manuel. 2012. "Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity." Molecules 17, no. 7: 8464-8470.