Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity.docVIP

Molecules 2012, 17, 8464-8470; doi:10.3390/moleculeOPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Enzymatic Reduction of 9-Methoxytariacuripyrone by Saccharomyces cerevisiae and Its Antimycobacterial Activity Patricia Alvarez-Fitz 1,2, Laura Alvarez 3, Silvia Marquina 3, Julieta Luna-Herrera 4 and Víctor Manuel Navarro-García 1,* 1 Laboratory of Microbiology, Biomedical Research Center of the South (IMSS), Argentina 1, Col. Centro, 62790 Xochitepec, Morelos, Mexico 2 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 3 Chemical Research Center, University of Morelos (UAEM), Av. Universidad 1001, Col. Chamilpa, 62209 Cuernavaca, Morelos, Mexico 4 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; E-Mail: vicmanchem@; Tel.: +52-777-361-21-94; Fax: +52-777-361-21-55. 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