Enzymatic reduction of 9-methoxytariacuripyrone by Saccharomyces cerevisiae and its antimycobacterial activity.
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).
Laboratory of Microbiology, Biomedical Research Center of the South (IMSS), Argentina 1, Col. Centro, Xochitepec, Morelos, Mexico. .
Patricia
P
Alvarez-Fitz
Laura
L
Alvarez
Silvia
S
Marquina
Julieta
J
Luna-Herrera
Víctor Manuel
VM
Navarro-García
D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D001711:Biotransformation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D010084:Oxidation-Reduction / Q000187:drug effects; D011753:Pyrones / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology*; D012441:Saccharomyces cerevisiae / Q000187:drug effects / Q000201:enzymology*
C092021:9-methoxytariacuripyrone; D000900:Anti-Bacterial Agents; D011753:Pyrones